Research update of Tribulus Terrestris.

  seminal trace...Tribulus Terrestris Extract.Saponins 40%45%70%90%UV.Protodioscin 20%.40%M.F.C51H84O22.CAS No:55056-80-9...

 

   Phytochemical info of Tribulus Terrestris:

 Product Name:
 Synonym:
 Definition: Tribulus Terrestris extract are majorly composed of
 Chemical information disclosed as following table:


  Tribulus Terrestris, also known as Puncture Vine and Goathead, has been used as a general tonic and as an herbal remedy for impotence. In recent years, Tribulus has developed a following among body builders and exercise enthusiasts. It is believed that Tribulus Terrestris increases testosterone. This is accomplished by raising the amount of LH (luteinizing hormone), which is produced by the pituitary gland. LH plays a significant role in regulating testosterone production. Tribulus has been used in some cultures to increase libido, especially in men, and to treat sexual dysfunction. It has also been used as a tonic to increase energy levels. Tribulus Terrestris can be used in combination with Yohimbe Bark as an enhancer of male performance, both sexually and athletically. Tribulus Terrestris is has also been used as a liver tonic. Tribulus Terrestris is especially effective for maintaining testosterone in individuals who are dieting or engaged in regular, strenuous exercise.
 
 This species is a perennial herb with a diffuse or prostrate habit, the young stems are hairy and become glabrous with age, growing to 30-100 cm (1-3 feet) long. The leaves are alternate, some opposite, even-pinnate, with 6 to 8 pairs of leaflets with very short or missing petiole. The solitary axillary flowers are bright yellow. The 5 persistant yellow sepals are about 10 mm long, the 5 yellow petals are 20 mm long. The fruits are 12-16 mm in diameter, made of 5 carpids each bearing two stout prickles. Those prickles make the plant quite unpleasant as they will stick in any bare feet passing by and are quite painful.
 It grows in full sun, in dry areas, on sandy or stony soils. It may grow so as to create rather vast areas of nice yellow flower beds. The plant also has various medicinal propertys; as it contains a lot of nitrate and potassium chloride it has diuretic powers. It is used against urinary infections and throat or mouth inflammations. The leaves are used in Senegal to rub rheumatisms, the fruits are supposedly galactologue, aphrodisiac and effective to stimulate the appetite. But the plant may also have some harmful effects, leading to liver and eyes lesions, its use must be cautious.


   Research update of Tribulus Terrestris.

   Application of Electrospray Ionization Mass Spectrometry Combined with Sequential Tandem Mass Spectrometry Techniques for the Profiling of Steroidal Saponin Mixture Extracted from Tribulus terrestris.:Planta Med. 1999 Feb;65(1):68-73.Fang S, Hao C, Liu Z, Song F, Liu S. Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, People's Republic of Chin.[PMID: 17260238]

 Using electrospray ionization mass spectrometry combined with sequential tandem mass spectrometry (ESI-MS (n)), the steroidal saponin mixture extracted from TRIBULUS TERRESTRIS was studied. The structures of five known steroidal saponins and two unknown steroidal saponins in the saponin mixture were investigated by sequential tandem mass spectrometry experiments. All of the steroidal saponins displayed similar fragmentation behavior in ESI-MS (n), and the characteristic cross ring cleavage pattern could be used as a fingerprint for the identification of steroidal saponins. The methodology has been established as a powerful tool for the profiling of mixtures, especially of crude plant extracts, and the structural elucidation of compounds.

   Effect of Tribulus terrestris extract on melanocyte-stimulating hormone expression in mouse hair follicles.:Nan Fang Yi Ke Da Xue Xue Bao. 2006 Dec;26(12):1777-9.Yang L, Lu JW, An J, Jiang X.Department of Traditional Chinese Medicine, Southern Medical University, Guangzhou 510515, China. yangliutcm@ 21cn.com[PMID: 17259119]

 OBJECTIVE: To observe the effect of Tribulus terrestris extract on melanocyte stimulating hormone (MSH) expression in C57BL/6J mouse hair follicles, and investigate the role of Tribulus terrestris extract in activation, proliferation, epidermal migration of dormant hair follicle melanocytes. METHODS: The aqueous extract of Tribulus terrestris was administered orally in specific pathogen-free C57BL/6J mouse at the daily dose equivalent to 1 g/1 kg in adult human, and the expression and distribution of MSH in the mouse hair follicles was observed with immunohistochemistry. RESULTS: The positivity rate of MSH expression in the hair follicle melanocytes was 75% in mice treated with the extract, significantly higher than the rate of only 18.75% in the control group (P<0.01). CONCLUSION: The aqueous extract of Tribulus terrestris can significantly increase MSH expression in the hair follicle melanocytes by activating tyrosinase activity and promoting melanocyte proliferation, melanine synthesis, and epidermal migration of dormant melanocytes.

   Saponins from Tribulus terrestris L are less toxic for normal human fibroblasts than for many cancer lines: influence on apoptosis and proliferation.:Exp Biol Med (Maywood). 2007 Jan;232(1):126-33.Neychev VK, Nikolova E, Zhelev N, Mitev VI.Department of Chemistry and Biochemistry, Medical University, Sofia 1431, Bulgaria. neychev@dir.bg.[PMID: 17202593]

 The objective of the study was to explore the influence of saponins derived from Tribulus terrestris L. (TT) on normal human skin fibroblasts and to compare it with their anticancer properties. In this study, [3H]thymidine incorporation and MTT to assess cell proliferation and viability, respectively, and immunoblotting and HPLC analysis to explore intracellular signal transduction pathways have been used. We found that TT caused a dose-dependent decrease in [3H]thymidine incorporation into the DNA of treated fibroblast compared to the untreated controls. Viability of treated cells remained within the control levels with treatment of up to 5 micro g TT/ml medium. It was significantly depressed with incubation in > or =6 micro g TT/ml medium with an IC50 of 12.6 micro g TT/ml of cultivating media. ERK1/2 was significantly dephosphorylated at 5 mins of incubation with TT until the 48th hour, when phosphorylation slightly recovered, but was still below the control levels. In contrast, p38 and JNK phosphorylation was positively influenced, with peaks at 1 hr and 24 hrs of incubation respectively. Phosphorylation/dephosphorylation events of SAPK/MAPK clearly correlated with Mkp-1 induction. Procaspase 3 was activated after 5 mins of incubation and coincided with a rapid actin cleavage. There was a significant decrease of putrescine concentration and a concomitant increase of spermidine and spermine at 2 mins of treatment. According to our results, TT is less toxic for normal human skin fibroblasts in comparison to many cancer lines investigated in previous studies. The molecular mechanism of this cytotoxicity involves up- and downregulation of polyamines' homeostasis, suppression of proliferation, and induction of apoptosis. Further research in this field using animal models would help to explore and interpret the potential properties of TT as an anticancer supplement.

   The protective effect of Tribulus terrestris in diabetes.:Ann N Y Acad Sci. 2006 Nov;1084:391-401.Amin A, Lotfy M, Shafiullah M, Adeghate E.Biology Department, United Arab Emirates University, PO Box: 17551, Al-Ain, Abu-Dhabi, United Arab Emirates. a.amin@uaeu.ac.ae.[PMID: 17151317]

 Tribulus terrestris L (TT) is used in the Arabic folk medicine to treat various diseases. The aim of this article was to investigate the protective effects of TT in diabetes mellitus (DM). Diabetes is known to increase reactive oxygen species (ROS) level that subsequently contributes to the pathogenesis of diabetes. Rats were divided into six groups and treated with either saline, glibenclamide (Glib), or TT for 30 days. Rats in group 1 were given saline after the onset of streptozotocin (STZ)-induced diabetes; the second diabetic group was administered Glib (10 mg/kg body weight). The third diabetic group was treated with the TT extract (2 g/kg body weight), while the first, second, and third nondiabetic groups were treated with saline solution, Glib, and TT extract, respectively. At the end of the experiment, serum and liver samples were collected for biochemical and morphological analysis. Levels of serum alanine aminotransferase (ALT) and creatinine were estimated. In addition, levels of malondialdehyde (MDA) and reduced glutathione (GSH) were assayed in the liver. The tested TT extract significantly decreased the levels of ALT and creatinine in the serum (P < 0.05) in diabetic groups and lowered the MDA level in liver (P < 0.05) in diabetic and (P < 0.01) nondiabetic groups. On the other hand, levels of reduced GSH in liver were significantly increased (P < 0.01) in diabetic rats treated with TT. Histopathological examination revealed significant recovery of liver in herb-treated rats. This investigation suggests that the protective effect of TT for STZ-induced diabetic rats may be mediated by inhibiting oxidative stress.

   Inhibitory effects of saponins from Tribulus terrestris on alpha-glucosidase in small intestines of rats.:Zhongguo Zhong Yao Za Zhi. 2006 Jun;31(11):910-3.Zhang SJ, Qu WJ, Zhong SY.School of Life Science, East China Normal University, Shanghai 200062, China.[PMID: 17048632]

 OBJECTIVE: To determine the effects of saponins from Tribulus terrestris (STT) on small intestinal a-glucosidase and postprandial blood glucose levels in rats. METHOD: The inhibitory effects of STT on a-glucosidase extracted from small intestines in rats were carried out in vitro. The blood glucose levels were measured after 60 min when sucrose (2 g x kg(-1)) or glucose (2 g x kg(-1)) was administered orally with STT (100 mg x kg(-1)). After treated with STT (100 mg x kg(-1)) for 14 d, the activities of a-glucosidase were determined daily, as well as the postprandial blood glucose levels after oraly administered sucrose (2 g x kg(-1)). RESULT: STT at concentrations of 0.1, 1 and 10 mg x mL(-1) reduced significantly the activities of alpha-glucosidase with inhibitory rates of (20.83 +/- 1.66)%, (43.73 +/- 2.39)% and (52.62 +/- 2.69)%, respectively. In facts STT (100 mg x kg(-1)) considerably decreased the blood glucose levels which was 52.61% of that of the control in rats co-administered orally with sucrose (2 g x kg(-1)). However, it showed no such effect on the rats co-administered orally with glucose (2 g x kg(-1)). After orally administered of STT for 14 d, the activity of alpha-glucosidase was significantly reduced (P < 0.05) to (58.17 +/- 3.24)% of that those in control. Meanwhile, The rats were oral administered with sucrose, the increase of postprandial blood glucose levels were (69.50 +/- 4.28)% of that in control 60 min later ( P < 0.05). CONCLUSION: It was through inhibiting the activity of a-glucosidase in small intestines that STT significantly retarded the increase in postprandial blood glucose levels in rats.


   Recovery of phosphatase and transaminase activity of mercury intoxicated Mus musculus (Linn.) liver tissue by Tribulus terrestris (Linn.) (Zygophyllaceae) extract.:Trop Biomed. 2006 Jun;23(1):45-51.Jagadeesan G, Kavitha AV.Department of Zoology, Faculty of Science, Annamalai University, Annamalainagar - 608 002.[PMID: 17041551]

 The efficacy of the methanolic fraction (MF) of Tribulus terrestris fruit extract on mercury intoxicated mice, Mus musculus has been studied. At a median-lethal dose of mercuric chloride (12.9 mg/kg body wt.) administration an enhanced level of glutamate oxaloacete transaminase (GOT), glutamate pyruvate transminase (GPT) and simultaneously decreased level of acid phosphatase (ACP) and alkaline phosphatase (ALT) activities were noticed in the liver. Due to the mercury toxicity the liver cells are damaged to cause the alterations in their enzymes. During the recovery period, all the enzymological parameters are restored to reach near normal level. The result suggested that the oral administration of MF of T. terrestris fruit extract has (6 mg/kg body wt.) provided protection against the mercuric chloride induced hepatic damage in the mice, M. musculus.

   FT-IR Study of the influence of Tribulus terrestris on Mercury intoxicated mice, Mus musculus liver.:Trop Biomed. 2005 Jun;22(1):15-22.Jagadeesan G, Kavitha AV, Subashini J.Toxicological Division, Department of Zoology, Annamalai University, Annamalainagar-608 002, Tamilnadu, India.[PMID: 16880750]

 FT-IR spectra of liver tissue isolated from mice, Mus musculus, have been recorded in the region of 4000 - 400 cm-1 for normal, mercury treated and recovery phase. In this study, the total protein content was found to be decreased in the liver tissues after treatment with median-lethal dose of mercuric chloride. The marked fall in the level of bio-chemical constituent in the tissue due to metal exposure indicates the rapid initiation of the breakdown of the bio-chemical constituents to meet the energy demand during toxic stress. During the recovery phase, the decreased levels of bio-chemical constituents are restored to near normal level. Methanol fractions of Tribulus terrestris fruit extract was administrated on mercury intoxicated mice for 15 days. After the administration, the mercury-intoxicated animals slowly recovered from the adverse effect of mercury poisoning with the help of plant bio-formulations. The results are discussed in detail.

   Effect of SA1, a herbal formulation, on sexual behavior and penile erection.:Biol Pharm Bull. 2006 Jul;29(7):1383-6.Park SW, Lee CH, Shin DH, Bang NS, Lee SM.College of Pharmacy, Sungkyunkwan University, Suwon, South Korea.[PMID: 16819173]

 SA1 is a mixture of 9 Oriental herbs (Korean red ginseng, fermented soybean, Tribulus terrestris, Fructus Rubi, Fructus Lycii, Semen Cuscutae, Dioscorea Rhizome, Fructus Corni and Fructus Crataegi) that are widely used as energizers and vitalizers in the indigenous system of medicine and have been alleged to improve the sexual functions in men. This study evaluated SA1 using both in vitro and in vivo experiments on laboratory animals in order to determine its effect on the sexual behavior and penile erection. The male rats used to examine the copulatory behavior were administered either the vehicle or SA1 (30, 100, 300, 600 mg/kg) orally for 2 weeks. The intracavernous pressure and systemic blood pressure were recorded in anesthetized rats. The responses to acetylcholine and SA1 of rabbit corpus cavernosum strips were also examined. There was an overall increase in the copulatory behavior parameters in the SA1-treated rats, which was reflected by a decrease in the mount and intromission latencies and an increase in the ejaculation latency and mount frequency. SA1 significantly increased the ratio of the intracavernous pressure to mean arterial pressure. In vitro, SA1 significantly enhanced the relaxation responses to acetylcholine. These results suggest that SA1 improves the sexual activity and erectile function.

   Steroidal saponins from the aerial parts of Tribulus alatus Del.:Phytochemistry. 2006 May;67(10):1011-8. Epub 2006 May 2.Temraz A, El Gindi OD, Kadry HA, De Tommasi N, Braca A. Dipartimento di Chimica Bioorganica e Biofarmacia, Universita di Pisa, Via Bonanno 33, 56126 Pisa, Italy.[PMID: 16631216]

 Six steroidal glycosides (1-6) were isolated from the aerial parts of Tribulus alatus Del. (Zygophyllaceae), together with one known cholestane, one spirostane, and six flavonol glycosides. Among them, 1 and 2 possess a furostane-type aglycone, 3 and 6 a cholestane structure, and 4 and 5 a spirostane skeleton. Their structural elucidation was accomplished by extensive spectroscopic methods including 1D ((1)H, (13)C, (13)C DEPT, TOCSY, ROESY) and 2D NMR experiments (DQF-COSY, HSQC, HMBC) as well as ESI-MS analysis.

   Abnormal turning behaviour, GABAergic inhibition and the degeneration of astrocytes in ovine Tribulus terrestris motor neuron disease.:Aust Vet J. 2006 Jan-Feb;84(1-2):53-8.Bourke CA.Orange Agricultural Institute, Forest Road, Orange, New South Wales 2800.[PMID: 16498837]

 OBJECTIVE: To observe the clinical signs of sheep affected by Tribulus terrestris motor neuron disease, to ascertain their response to striatal dopamine reducing drugs, and to examine their brains and spinal cords for microscopic changes. PROCEDURES: Twenty-eight sheep displaying well developed clinical signs of the disorder were observed. Twenty-two of these and 22 normal sheep were then randomly allocated to three groups and treated with diazepam, chlorpromazine, or xylazine. The time that it took an animal to return to a standing position following drug administration was recorded. The brain and complete spinal cord were removed from each of the other six affected sheep and fixed in formalin. Brains were sectioned throughout at 5 mm intervals and spinal cords at 10 mm intervals. All tissues were paraffin embedded and examined by light microscopy. A few samples were examined by electron microscopy. RESULTS: Clinical signs included postural asymmetry with a right:left body-side dominance within the group of 50:50, unequal flaccid paresis in the pelvic limbs, extensor muscle atrophy and adduction of the weaker pelvic limb, and concurrent abduction of the stronger. Forward motion followed either a fixed left or right hand curved trajectory, the sheep no longer being able to choose which. Twelve animals intermittently displayed rotational behaviour that involved loss of postural balance without locomotor activation. The administration of diazepam, chlorpromazine, or xylazine caused limb paresis and sedation, with affected sheep being slower than normal sheep by factors of 8, 3 and 2 respectively, to return to a standing position. There were scattered areas of mild Wallerian degeneration throughout the spinal cord, and in both the brain and the cord there were small numbers of degenerate astrocytes containing novel cytoplasmic pigment granules. CONCLUSIONS: Affected sheep had a dysfunction in the control of directional change and this provides a new insight into the normal mechanism for 'turning' in quadrupeds. Directional change requires a functional asymmetry or lateralisation within the upper motor neuron to accommodate a difference in the rate of forward progression of each body side and, simultaneously, a lateral shift of the centre of gravity. The sensitivity of affected sheep to diazepam is consistent with a pre-existing elevation in GABAergic neuronal inhibition, probably as a result of a reduction in glutamatergic neuronal excitation. The cytoplasmic pigment found in degenerate astrocytes was novel and its presence in the brain nuclei known to contribute to turning behaviour could have aetiological significance. The motor output of the basal ganglia in Tribulus neurotoxicity appeared to be excessively inhibitory to the pelvic limb extensor muscles and was asymmetric, causing fixation of the turning posture but not locomotor activation. An intoxication of specific purine sensitive, glutamate releasing astrocytes, located in nuclei controlling turning, was suspected.


   Bioactivity studies of the individual ingredients of the Dashamularishta.:Pak J Pharm Sci. 2004 Jan;17(1):9-17.Jabbar S, Khan MT, Choudhuri MS, Sil BK.Pharmacology Research Lab, Faculty of Pharmaceutical Sciences, University of Science and Technology Chittagong, Foy's Lake, Chittagong, Bangladesh.[PMID: 16414581]

 The bioactivity studies of the individual ingredients of Dashamularishta--a classical Ayurvedic preparation were done with the aqueous extracts of the individual ingredients. The Aegle marmelos Correa. exhibited severe toxicity to the brine shrimp (BST) nauplii, wheat rootlet growth (WRG) inhibition bioassay and lettuce seed germination (LSG) bioassay. It exhibited no inhibition to the growth of PPR and Reo virus in vero cell line. The Oroxylum indicum exhibited moderate toxicity to the BST and WRG, but it is not toxic to the LSG. It exhibited no inhibition to the growth of PPR and Reo virus. The Stereospermum suaveolens exhibited severe toxicity to the BST and LSG, but it is not toxic to the WRG. It exhibited total inhibition to the growth of Reo virus, but it has not effect on the PPR virus. The Premna integrifolia showed severe toxicity to the BST, but it was not toxic to the WRG and LSG. It exhibited no inhibition to the growth of PPR and Reo virus. The Gmelina arborea exhibited severe toxicity to the BST and WRG, but it is not toxic to the LSG. It exhibited no inhibition to the growth of PPR and Reo virus. The Solanum xanthocarpum showed mild toxicity to the BST, WRG and LSG. It exhibited 75% inhibition to the growth of Reo virus. The Solanum indicum showed no toxicity to the BST, WRG and LSG. It exhibited 75% inhibition to the growth of PPR virus. The Desmodium gangeticum showed no toxicity to the BST, but moderate toxicity to the WRG and LSG. It exhibited total inhibition to the growth of PPR virus. The Uraria lagopoides showed no toxicity to the BST, WRG and LSG. It exhibited total inhibition to the growth of Reo virus. The Tribulus terrestris showed no toxicity to the BST, but showed moderate toxicity to the WRG and LSG. It exhibited 75% inhibition to the growth of both PPR and Reo virus.

   In vitro and in vivo antifungal activities of the eight steroid saponins from Tribulus terrestris L. with potent activity against fluconazole-resistant fungal pathogens.:Biol Pharm Bull. 2005 Dec;28(12):2211-5.Zhang JD, Cao YB, Xu Z, Sun HH, An MM, Yan L, Chen HS, Gao PH, Wang Y, Jia XM, Jiang YY.Department of Pharmacology, College of Pharmacy, Second Military Medical University, Shanghai, PR China.[PMID: 16327151]

 Antifungal activity of natural products is being studied widely. Saponins are known to be antifungal and antibacterial. We have isolated eight steroid saponins from Tribulus terrestris L., namely TTS-8, TTS-9, TTS-10, TTS-11, TTS-12, TTS-13, TTS-14 and TTS-15. TTS-12 and TTS-15 were identified as tigogenin-3-O-beta-D-xylopyranosyl(1-->2)-[beta-D-xylopyranosyl(1-->3)]-beta-D-glucopyranosyl(1-->4)-[alpha-L-rhamnopyranosyl(1-->2)]-beta-D-galactopyranoside and tigogenin-3-O-beta-D-glucopyranosyl(1-->2)-[beta-D-xylopyranosyl(1-->3)]-beta-D-glucopyranosyl(1-->4)-beta-D-galactopyranoside, respectively. The in vitro antifungal activities of the eight saponins against six fluconazole-resistant yeasts, Candida albicans, Candida glabrata, Candida parapsilosis, Candida tropicalis, Candida krusei, and Cryptococcus neoformans were studied using microbroth dilution assay. The results showed that TTS-12 and TTS-15 were very effective against several pathogenic candidal species and C. neoformans in vitro. It is noteworthy that TTS-12 and TTS-15 were very active against fluconazole-resistant C. albicans (MIC(80)=4.4, 9.4 microg/ml), C. neoformans (MIC(80)=10.7, 18.7 microg/ml) and inherently resistant C. krusei (MIC(80)=8.8, 18.4 microg/ml). So in vivo activity of TTS-12 in a vaginal infection model with fluconazole-resistant C. albicans was studied in particular. Our studies revealed TTS-12 also showed in vivo activities against fluconazole-resistant yeasts. In conclusion, steroid saponins TTS-12 and TTS-15 from Tribulus terrestris L. have significant in vitro antifungal activity against fluconazole-resistant fungi, especially TTS-12 also showed in vivo activity against fluconazole-resistant C. albicans.

   Antihypertensive and vasodilator effects of methanolic and aqueous extracts of Tribulus terrestris in rats.:J Ethnopharmacol. 2006 Apr 6;104(3):351-5. Epub 2005 Nov 9.Phillips OA, Mathew KT, Oriowo MA.Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Kuwait University, P.O. Box 24923, 13110 Safat, Kuwait.[PMID: 16289603]

 The effects of methanolic and aqueous extracts of Tribulus terrestris on rat blood pressure (BP) and the perfused mesenteric vascular bed were investigated. The extracts dose-dependently reduced BP in spontaneously hypertensive rats (SHRs) with the aqueous fraction being more potent than the methanolic fraction at all doses tested. In vitro, the methanolic but not aqueous extract produced a dose-dependent increase in perfusion pressure of the mesenteric vascular bed. When perfusion pressure was raised with phenylephrine (10(-5) M), the aqueous extract produced a dose-dependent reduction in perfusion pressure at all doses. A low dose of the methanolic extract produced a vasoconstrictor effect while higher doses produced dose-dependent reduction in perfusion pressure. L-NAME (10(-4) M) significantly reduced but did not abolish vasodilation induced by the extracts. Vasodilator responses to aqueous and methanolic fractions were significantly reduced in preparations where perfusion pressure was raised with KCl (60 mM). A combination of KCl and L-NAME abolished the vasodilator responses induced by the extracts. It was concluded that methanolic and aqueous extracts of Tribulus terrestris possess significant antihypertensive activity in spontaneously hypertensive rats. The antihypertensive effects appeared to result from a direct arterial smooth muscle relaxation possibly involving nitric oxide release and membrane hyperpolarization.

   Cytotoxic furostanol saponins and a megastigmane glucoside from tribulus parvispinus.:J Nat Prod. 2005 Oct;68(10):1549-53.Perrone A, Plaza A, Bloise E, Nigro P, Hamed AI, Belisario MA, Pizza C, Piacente S.Dipartimento di Scienze Farmaceutiche, Universita degli Studi di Salerno, Via Ponte Don Melillo, 84084 Fisciano, Salerno, Italy.[PMID: 16252924]

 Two new furostanol saponins, (25R)-26-O-beta-D-glucopyranosyl-5alpha-furostan-2alpha,3beta,22alpha,26-tetraol 3-O-{beta-D-galactopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside} (1) and (25R)-26-O-beta-D-glucopyranosyl-5alpha-furostan-3beta,22alpha,26-triol 3-O-{beta-D-galactopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside} (2), and their O-methyl derivatives (3 and 4), and a new megastigmane glucoside, (6S,7E,9xi)-6,9,10-trihydroxy-4,7-megastigmadien-3-one 10-O-beta-D-glucopyranoside (6), along with one known spirostanol saponin, gitonin (5), and four known megastigmane glucosides were isolated from the aerial parts of Tribulus parvispinus. Their structures were established by detailed spectroscopic analysis. The cytotoxic activities of 1-6 against U937, MCF7, and HepG2 cells were evaluated. Compounds 2 (IC(50) 0.5 microM) and 5 (IC(50) 0.1 microM) showed the highest activity against U937 cells.

   Antifungal activities and action mechanisms of compounds from Tribulus terrestris L.:J Ethnopharmacol. 2006 Jan 3;103(1):76-84. Epub 2005 Oct 5.Zhang JD, Xu Z, Cao YB, Chen HS, Yan L, An MM, Gao PH, Wang Y, Jia XM, Jiang YY.Department of Pharmacology, College of Pharmacy, Second Military Medical University, Shanghai, PR China.[PMID: 16169173]

 Antifungal activity of natural products is being studied widely. Saponins are known to be antifungal and antibacterial. We used bioassay-guided fractionation to have isolated eight steroid saponins from Tribulus terrestris L., which were identified as hecogenin-3-O-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside (TTS-8), tigogenin-3-O-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside (TTS-9), hecogenin-3-O-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside (TTS-10), hecogenin-3-O-beta-D-xylopyranosyl (1-->3)-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside (TTS-11), tigogenin-3-O-beta-D-xylopyranosyl (1-->2)-[beta-D-xylopyranosyl (1-->3)]-beta-D-glucopyranosyl (1-->4)-[alpha-L-rhamnopyranosyl (1-->2)]-beta-D-galactopyranoside (TTS-12), 3-O-[beta-D-xylopyranosyl (1-->2)-[beta-D-xylopyranosyl (1-->3)]-beta-D-glucopyranosyl (1-->4)-[alpha-L-rhamnopyranosyl (1-->2)]-beta-D-galactopyranosyl]-26-O-beta-D-glucopyranosyl-22-methoxy-(3beta,5alpha,25R)-furostan-3,26-diol (TTS-13), hecogenin-3-O-beta-D-glucopyranosyl (1-->2)-[beta-D-xylopyranosyl (1-->3)]-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside (TTS-14), tigogenin-3-O-beta-D-glucopyranosyl (1-->2)-[beta-D-xylopyranosyl (1-->3)]-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside (TTS-15). The in vitro antifungal activities of the eight saponins against five yeasts, Candida albicans, Candida glabrata, Candida parapsilosis, Candida tropicalis and Cryptococcus neoformans were studied using microbroth dilution assay. In vivo activity of TTS-12 in a Candida albicans vaginal infection model was studied in particular. The results showed that TTS-12 and TTS-15 were very effective against several pathogenic candidal species and Cryptococcus neoformans in vitro. It is noteworthy that TTS-12 and TTS-15 were very active against Candida albicans (MIC(80) = 10 and 2.3 microg/mL) and Cryptococcus neoformans (MIC(80) = 1.7 and 6.7 microg/mL). Phase contrast microscopy showed that TTS-12 inhibited hyphal formation, an important virulence factor of Candida albicans, and transmission electron microscopy showed that TTS-12 destroyed the cell membrane of Candida albicans. In conclusion, TTS-12 has significant in vitro and in vivo antifungal activity, weakening the virulence of Candida albicans and killing fungi through destroying the cell membrane.


   Effects of Tribuli saponins on left ventricular remodeling after acute myocardial infarction in rats with hyperlipidemia.:Chin J Integr Med. 2005 Jun;11(2):142-6.[PMID: 16150203]

 OBJECTIVE: To observe the effect of Tribuli saponins (TS) on left ventricular remodeling after acute myocardial infarction (AMI) in rats with hyperlipemia. METHODS: A composite model of myocardial infarction and hyperlipemia was established and treated with TS to observe its effect on cardiac structure and function by echocardiography. RESULTS: (1) Cardiac function: As compared with the model group, the fractional shortening (FS) and ejection fraction (EF) got increased, and the left ventricular end diastolic volume (LVEDV) and systolic volume (LVESV) got lower in the groups treated with high dose TS and simvastatin (P < 0.05 or P < 0.01), but difference between the two treated groups was insignificant. (2) Cardiac structure: As compared with the model group, the left ventricular dimension end diastole (LVDd) and systole (LVDs) in the groups treated with high dose TS and simvastatin got lower (P < 0.05 or P < 0.01). No treatment showed any effect on the thickness of ventricular wall. (3)Ventricular weight index: Both high dose TS and simvastatin could decrease the left ventricular weight index (LVWI) (P < 0.05). CONCLUSION: TS could attenuate the left ventricular remodeling after acute myocardial infarction to certain extent, and improve cardiac function in the early phase after AMI, thus playing an important role in controlling morbidity and mortality of cardiac events and long-term prognosis.

   The aphrodisiac herb Tribulus terrestris does not influence the androgen production in young men.:J Ethnopharmacol. 2005 Oct 3;101(1-3):319-23.Neychev VK, Mitev VI.Department of Chemistry and Biochemistry, Medical University, 2 Zdrave str., Sofia-1431, Bulgaria. neychev@dir.bg.[PMID: 15994038]

 OBJECTIVE: The aim of the current study is to investigate the influence of Tribulus terrestris extract on androgen metabolism in young males. DESIGN AND METHODS: Twenty-one healthy young 20-36 years old men with body weight ranging from 60 to 125 kg were randomly separated into three groups-two experimental (each n=7) and a control (placebo) one (n=7). The experimental groups were named TT1 and TT2 and the subjects were assigned to consume 20 and 10 mg/kg body weight per day of Tribulus terrestris extract, respectively, separated into three daily intakes for 4 weeks. Testosterone, androstenedione and luteinizing hormone levels in the serum were measured 24 h before supplementation (clear probe), and at 24, 72, 240, 408 and 576 h from the beginning of the supplementation. RESULTS: There was no significant difference between Tribulus terrestris supplemented groups and controls in the serum testosterone (TT1 (mean+/-S.D.: 15.75+/-1.75 nmol/l); TT2 (mean+/-S.D.: 16.32+/-1.57 nmol/l); controls (mean+/-S.D.: 17.74+/-1.09 nmol/l) (p>0.05)), androstenedione (TT1 (mean+/-S.D.: 1.927+/-0.126 ng/ml); TT2 (mean+/-S.D.: 2.026+/-0.256 ng/ml); controls (mean+/-S.D.: 1.952+/-0.236 ng/ml) (p>0.05)) or luteinizing hormone (TT1 (mean+/-S.D.: 4.662+/-0.274U/l); TT2 (mean+/-S.D.: 4.103+/-0.869U/l); controls (mean+/-S.D.: 4.170+/-0.406U/l) (p>0.05)) levels. All results were within the normal range. The findings in the current study anticipate that Tribulus terrestris steroid saponins possess neither direct nor indirect androgen-increasing properties. The study will be extended in the clarifying the probable mode of action of Tribulus terrestris steroid saponins.

   Effect of Tribulus terrestris on nicotinamide adenine dinucleotide phosphate-diaphorase activity and androgen receptors in rat brain.:J Ethnopharmacol. 2005 Jan 4;96(1-2):127-32.Gauthaman K, Adaikan PG.Department of Obstetrics and Gynaecology, National University Hospital, National University of Singapore, 5 Lower Kent Ridge Road, Singapore 119074, Singapore.[PMID: 15588660]

 Tribulus terrestris L. (Zygophyllaceae) have been used as an aphrodisiac both in the Indian and Chinese traditional systems of medicine. Administration of Tribulus terrestris extract (TT) increased sexual behaviour and intracavernous pressure both in normal and castrated rats and these effects were probably due to the androgen increasing property of TT. The objective of the present study is to evaluate the effect of TT on nicotinamide adenine dinucleotide phosphate-diaphorase (NADPH-d) activity and androgen receptor (AR) immunoreactivity in rat brain. Twenty-four adult male Sprague-Dawley rats were divided into two groups of twelve each. Group I was treated with distilled water and Group II was treated with TT at the dose of 5mg/kg body weight orally, once daily for 8 weeks. Following treatment transcardiac perfusion was done with Ringer lactate, 4% paraformaldehyde and 30% sucrose. The brain tissue was removed and sections of the paraventricular (PVN) area of hypothalamus were taken for NADPH-d and AR immunostaining. There was an increase in both NADPH-d (67%) and AR immunoreactivity (58%) in TT treated group and these results were statistically significant compared to the control. Chronic treatment of TT in rats increases the NADPH-d positive neurons and AR immunoreactivity in the PVN region. Androgens are known to increase both AR and NADPH-d positive neurons either directly or by its conversion to oestrogen. The mechanism for the observed increase in AR and NADPH-d positive neurons in the present study is probably due to the androgen increasing property of TT. The findings from the present study add further support to the aphrodisiac claims of TT.

   A novel furostanol saponin from Tribulus terrestris of Bulgarian origin.:Fitoterapia. 2004 Mar;75(2):117-22.Conrad J, Dinchev D, Klaiber I, Mika S, Kostova I, Kraus W.Department of Chemistry, University of Hohenheim, 70593 Stuttgart, Germany.[PMID: 15030914]

 The phytochemical investigation of the aerial parts of Tribulus terrestris of Bulgarian origin has resulted in the isolation of the novel furostanol saponin 1, named tribol, together with the known spirostanol saponins 2 and 3 and sitosterol glucoside. The structure of tribol was determined as (25R)-furost-5(6)-ene-3beta,16,26-triol-3-O-alpha-rhamnopyranosyl-(1-->2)-[alpha-rhamnopyranosyl-(1-->4)]-beta-glucopyranoside (1) by spectral analysis, including extensive 1D and 2D-NMR experiments.

   Terrestrinins A and B, two new steroid saponins from Tribulus terrestris.:J Asian Nat Prod Res. 2003 Dec;5(4):285-90.Huang JW, Tan CH, Jiang SH, Zhu DY.State Key Laboratory of Drug Research, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, 294 Taiyuan Road, Shanghai 200031, People's Republic of China.[PMID: 14604238]

 Two new steroid saponins, named terrestrinins A (1) and B (2), along with six known compounds were isolated from the Chinese medicine herb Tribulus terrestris, and their chemical structures were elucidated as 26-O-beta-D-glucopyranosyl-(25S)-furostan-4(5),20(22)-diene-3,12-dione (1) and 26-O-beta-D-glucopyranosyl-(25S)-5alpha-furostane-3beta,22alpha,26-triol-3-O-beta-D-xylopyranosyl(1 --> 3)-[(beta-D-xylopyranosyl(1 --> 2)]-beta-D-glucopyranosyl(1 --> 4)-[alpha-L-rhamnopyranosyl(1 --> 2)]-beta-D-galactopyranoside (2) on the basis of spectroscopic techniques.


   Ingestion of a dietary supplement containing dehydroepiandrosterone (DHEA) and androstenedione has minimal effect on immune function in middle-aged men.:J Am Coll Nutr. 2003 Oct;22(5):363-71.Kohut ML, Thompson JR, Campbell J, Brown GA, Vukovich MD, Jackson DA, King DS.Department of Health and Human Performance, Iowa State University, Ames, Iowa 50011, USA. mkohut@iastate.edu.[PMID: 14559928]

 OBJECTIVE: This study investigated the effects of four weeks of intake of a supplement containing dehydroepiandrosterone (DHEA), androstenedione and herbal extracts on immune function in middle-aged men. DESIGN: Subjects consumed either an oral placebo or an oral supplement for four weeks. The supplement contained a total daily dose of 150 mg DHEA, 300 mg androstenedione, 750 mg Tribulus terrestris, 625 mg chrysin, 300 mg indole-3-carbinol and 540 mg saw palmetto. MEASUREMENTS: Peripheral blood mononuclear cells were used to assess phytohemagglutinin(PHA)-induced lymphocyte proliferation and cytokine production. The cytokines measured were interleukin (IL)-2, IL-4, IL-10, IL-1beta, and interferon (IFN)-gamma. Serum free testosterone, androstenedione, estradiol, dihydrotestosterone (DHT) were also measured. RESULTS: The supplement significantly increased serum levels of androstenedione, free testosterone, estradiol and DHT during week 1 to week 4. Supplement intake did not affect LPS or ConA proliferation and had minimal effect on PHA-induced proliferation. LPS-induced production of IL-1beta, and PHA-induced IL-2, IL-4, IL-10, or IFN-gamma production was not altered by the supplement. The addition of the same supplement, DHEA or androstenedione alone to lymphocyte cultures in vitro did not alter lymphocyte proliferation, IL-2, IL-10, or IFN-gamma, but did increase IL-4. In addition, serum HDL-C concentration significantly declined. CONCLUSION: These findings suggest that, although chronic intake of a complex dietary supplement containing DHEA, androstenedione and herbal extracts increases serum androgen levels, it has minimal effect on immune function in middle-aged men.

   Effect of saponin from Tribulus terrestris on hyperlipidemia.:Zhong Yao Cai. 2003 May;26(5):341-4.Chu S, Qu W, Pang X, Sun B, Huang X.School of Life Science, East China Normal University, Shanghai 200062.[PMID: 14535016]

 The preventive and therapeutic effects of saponin from Tribulus terrestris L. on diet-induced hyperlipidemia in mice have been studied. It showed that in preventive experiment the saponin could significantly low the levels of serum TC (P < 0.05), LDL-c (P < 0.01) and liver TC (P < 0.05), TG (P < 0.05), and increase the activities of superoxide-dismutase (SOD) in liver. The therapeutic experiment showed that the saponin could significantly reduce the contents of serum TC (P < 0.05) and liver TC (P < 0.01).

   Study of antihypertensive mechanism of Tribulus terrestris in 2K1C hypertensive rats: role of tissue ACE activity.:Life Sci. 2003 Oct 24;73(23):2963-71.Sharifi AM, Darabi R, Akbarloo N.Department of Pharmacology, Razi Institute for Drug Research and Cellular and Molecular Research Center, School of Medicine, Iran University of Medical Sciences, PO Box 14155-6183 Tehran, Iran. sharifal@yahoo.com.[PMID: 14519445]

 Tribulus terrestris is a natural herb used for treating many diseases including hypertension. According to previous reports, aqueous extract of tribulus fruits may have some antihypertensive effect with an unknown mechanism. The present study investigated the antihypertensive mechanism of tribulus in 2K1C hypertensive rats by measurement of circulatory and local ACE activity in aorta, heart, kidney and lung. Four groups of rats were selected; control, sham, operated or hypertensive and tribulus treated hypertensive group. Hypertension was induced using silver clip on renal artery by surgery. Four weeks after surgery, a single daily dose of 10 mg/kg of lyophilized aqueous extract of tribulus fruit were given orally to 2K1C rats for four weeks. ACE activity was determined by high performance liquid chromatography (HPLC). Blood pressure was measured by the tail-cuff method. The systolic blood pressure (SBP) was significantly increased in 2K1C rats compared to control rats. The SBP of tribulus fed hypertensive rats was significantly decreased compared to hypertensive rats. The ACE activity in all tissues of 2K1C rats including: aorta, heart, kidney, lung as well as serum were significantly increased compared to normal rats. The ACE activity in all tissues of tribulus fed hypertensive rats was significantly lower than that of hypertensive rats, which was more pronounced in kidney. These results indicated that there is a negative correlation between consumption of tribulus and ACE activity in serum and different tissues in 2K1C rats.

   A review of plant-derived and herbal approaches to the treatment of sexual dysfunctions.:J Sex Marital Ther. 2003 May-Jun;29(3):185-205.Rowland DL, Tai W.Department of Psychology, Valparaiso University, Valparaiso, Indiana 46383, USA. david.rowland@valpo.edu.[PMID: 12851124]

 Despite the increasing availability of effective conventional medical treatments, plant-derived and herbal remedies continue to provide a popular alternative for men and women seeking to improve their sex life. Nevertheless, the efficacy of most herbal agents in treating sexual problems remains uncertain. Therapists and consumers alike would benefit from an increased understanding of commonly used herbal agents on the market, their purported or supported effects, and their potential side effects. To this end, we cataloged the major prosexual herbal agents currently sold in several representative health food stores. We also specify the sexual problem purportedly ameliorated by each herbal agent. Finally, we evaluate eight herbal agents commonly promoted for the treatment of sexual problems. This evaluation includes a review of the research supporting the use, efficacy, dose, adverse effects, contraindications, and possible mechanism of action of each. We conclude by commenting on the quality of current research, pointing out gaps in our knowledge, and noting the need for rigorous research and product control to adequately address questions regarding the efficacy of these agents.

   Sexual effects of puncturevine (Tribulus terrestris) extract (protodioscin): an evaluation using a rat model.:J Altern Complement Med. 2003 Apr;9(2):257-65.Gauthaman K, Ganesan AP, Prasad RN.Department of Obstetrics and Gynaecology, National University Hospital, National University of Singapore, Singapore.[PMID: 12804079]

 OBJECTIVE: Apart from its claims for improvement of sexual functions in men, the puncturevine plant (Tribulus terrestris: TT) has long been considered as an energizer and vitalizer in the indigenous system of medicine. Sexual behavior and intracavernous pressure (ICP) measurements were taken in rats to scientifically validate the claim of TT [containing protodioscin (PTN)] as an aphrodisiac. MATERIALS AND METHODS: Forty sexually mature male Sprague-Dawley rats were randomly divided into four groups of 10 each. Group I served as a control group and groups II, III, and IV were treated with three different doses of TT extract (2.5, 5 and 10 mg/kg body weight, respectively), orally, once daily for 8 weeks. Weight was recorded and the rats from all four groups were subjected to sexual behavior studies with primed females and various parameters namely mount and intromission frequencies (MF and IF, respectively), mount, intromission and ejaculation latencies (ML, IL, and EL, respectively) as well as postejaculatory interval (PEI) were recorded. In addition, blood pressure and ICP were recorded for all rats at the end of study. RESULTS: Increases in body weight (by 9, 23, and 18% for groups II, III & IV) and ICP (by 43% and 26% for groups III and IV) were statistically significant compared to the control group. Increases in MF (by 27% and 24%) and IF (by 19% and 22%) for the groups III and IV were statistically significant. Decreases in ML (by 16%, 23%, and 22% for groups II, III, and IV) and PEI (by 20% for group III) were statistically significant compared to the control. CONCLUSIONS: The weight gain and improvement in sexual behavior parameters observed in rats could be secondary to the androgen increasing property of TT (PTN) that was observed in our earlier study on primates. The increase in ICP which confirms the proerectile aphrodisiac property of TT could possibly be the result of an increase in androgen and subsequent release of nitric oxide from the nerve endings innervating the corpus cavernosum.


   Tribulus terrestris: preliminary study of its diuretic and contractile effects and comparison with Zea mays.:J Ethnopharmacol. 2003 Apr;85(2-3):257-60.Al-Ali M, Wahbi S, Twaij H, Al-Badr A.Department of Urology, St. Bartholomew's, The Royal London & Homerton University Hospitals, 224B East End Road, East Finchley, N2 8AX, London, UK. alalimun@hotmail.com.[PMID: 12639749]

 OBJECTIVES: Tribulus terrestris L. (Zygophyllaceae) which is called Al-Gutub (in Iraqi dialect) or Quti;ba (in classical Arabic medicine), and Zea mays were both used alone or in combination by Iraqi herbalists to propel urinary stones. We studied the aqueous extract of the leaves and fruits of T. terrestris and the hair of Z. mays, to determine their diuretic activity and the contractile effect of T. terrestris. METHODS: The aqueous extract was filtered and the solvent was evaporated to produce a dry crude extract. The dry extract was then dissolved in physiological saline to make the required concentrations. Wistar male rats were used for the diuresis test and strips of isolated Guinea pig ileum were used for the contractility test. RESULTS: The aqueous extract of T. terrestris, in oral dose of 5g/kg elicited a positive diuresis, which was slightly more than that of furosemide. Z. mays aqueous extract did not result in significant diuresis when given alone in oral dose of 5g/kg, while combination of Z. mays and T. terrestris extracts produced the same extent of diuresis as that produced by T. terrestris alone. Na(+), K(+) and Cl(+) concentrations in the urine had also much increased. In addition to its diuretic activity T. terrestris had evoked a contractile activity on Guinea pig ileum. CONCLUSION: T. terrestris has long been used empirically to propel urinary stones. The diuretic and contractile effects of T. terrestris indicate that it has the potential of propelling urinary stones and merits further pharmacological studies.

   Hypoglycemic effect of saponin from Tribulus terrestris.:Zhong Yao Cai. 2002 Jun;25(6):420-2.Li M, Qu W, Wang Y, Wan H, Tian C.School of Life Science, East China Normal University, Shanghai 200062.[PMID: 12583337]

 OBJECTIVE: To study the hypoglycemic effect of saponin from Tribulus terrestris L. METHOD: Alloxan was used to establish the diabetic model in mice. Phenformin Hydrochlride Tables was used as the positive control. The level of glucose, triglyceride, cholesterol and SOD in serum were determined. RESULTS: The level of serum glucose could be significantly reduced by saponin from Tribulus terrestris, which was the rate of 26.25% and 40.67% in normal mice and diabetic mice in respectively. The level of serum triglyceride could be reduced 23.35%. The saporin could also decrease the content of serum cholesterol. Serum SOD activity of the mice was increased by the saponin. CONCLUSION: Saponin from Tribulue terrestris could significantly reduce the level of serum glucose.

   Biologically active steroidal glycosides from Tribulus terrestris.:Pharmazie. 2002 Jul;57(7):491-3.Bedir E, Khan IA, Walker LA.National Center for Natural Products Research, University of Mississippi, USA.[PMID: 12168535]

 The steroidal saponin constituents obtained from Tribulus terrestris were tested for their antimicrobial and cytotoxic effects. The spirostanol-based steroidal saponins 1-3 exhibited remarkable activity against fungal organisms (Candida albicans and Cryptococcus neoformans) and cancer cell lines [human malignant melanoma (SK-MEL), human oral epidermoid carcinoma (KB), human breast ductal carcinoma (BT-549), and human ovary carcinoma (SK-OV-3)], while none of the compounds possessing the furostanol framework 4-7 showed activity. The most active spirostanol glycoside, compound 3 exhibited a broad range of anticancer activity against cell lines, SK-MEL, KB, BT-549 and SK-OV-3 at IC50s of 6.0, 7.0, 6.0 and 8.2 micrograms/ml, respectively, while compounds 1 and 2 showed selective cytotoxicity against SK-MEL at 6.7 and 9.1 micrograms/ml, respectively. The minimum inhibitory concentrations (MIC) in antifungal bioassay for compounds 1-3 varied from 1.5 to 6.2 micrograms/ml, which prompted to conclude certain structural features are required for these bioactivities.

   Determination of steroidal saponins in Tribulus terrestris by reversed-phase high-performance liquid chromatography and evaporative light scattering detection.:J Pharm Sci. 2001 Nov;90(11):1752-8.Ganzera M, Bedir E, Khan IA. National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, University, Mississippi 38677, USA.[PMID: 11745732]

 This paper describes the first analytical method suitable for the determination of steroidal saponins in Tribulus terrestris. A separation by high performance liquid chromatography (HPLC) was achieved by using a reversed-phase (RP-18) column, evaporative light scattering (ELS) detection, and a water/acetonitrile gradient as the mobile phase. The marker compound, protodioscin, was detected at a concentration as low as 10.0 microg/mL. Several different samples of plant material were successfully analyzed, and depending on origin and plant part used for extraction, significant differences in the composition of the saponins were observed. The analysis of market products showed considerable variations of 0.17 to 6.49% in the protodioscin content.

   Effects of androstenedione-herbal supplementation on serum sex hormone concentrations in 30- to 59-year-old men.:Int J Vitam Nutr Res. 2001 Sep;71(5):293-301.Brown GA, Vukovich MD, Martini ER, Kohut ML, Franke WD, Jackson DA, King DS.Exercise Biochemistry Laboratory, Department of Health and Human Performance, Iowa State University, Ames, IA, USA.[PMID: 11725694]

 The effectiveness of a nutritional supplement designed to enhance serum testosterone concentrations and prevent the formation of dihydrotestosterone and estrogens from the ingested androgens was investigated in healthy 30- to 59-year old men. Subjects were randomly assigned to consume DION (300 mg androstenedione, 150 mg dehydroepiandrosterone, 540 mg saw palmetto, 300 mg indole-3-carbinol, 625 mg chrysin, and 750 mg Tribulus terrestris per day; n = 28) or placebo (n = 27) for 28 days. Serum free testosterone, total testosterone, androstenedione, dihydrotestosterone, estradiol, prostate-specific antigen (PSA), and lipid concentrations were measured before and throughout the 4-week supplementation period. Serum concentrations of total testosterone and PSA were unchanged by supplementation. DION increased (p < 0.05) serum androstenedione (342%), free testosterone (38%), dihydrotestosterone (71%), and estradiol (103%) concentrations. Serum HDL-C concentrations were reduced by 5.0 mg/dL in DION (p < 0.05). Increases in serum free testosterone (r2 = 0.01), androstenedione (r2 = 0.01), dihydrotestosterone (r2 = 0.03), or estradiol (r2 = 0.07) concentrations in DION were not related to age. While the ingestion of androstenedione combined with herbal products increased serum free testosterone concentrations in older men, these herbal products did not prevent the conversion of ingested androstenedione to estradiol and dihydrotestosterone.


   Three new saponins from Tribulus terrestris.:Planta Med. 2000 Aug;66(6):545-50.Xu YX, Chen HS, Liang HQ, Gu ZB, Liu WY, Leung WN, Li TJ.Department of Phytochemistry, College of Pharmacy, Second Military Medical University, Shanghai, People's Republic of China.[PMID: 10985082]

 Three new steroidal saponins 1-3, together with five known steroidal saponins, L-mannitol and an inorganic salt were isolated from Tribulus terrestris L. (Zygophyllaceae). The structures of the new steroidal saponins were elucidated as hecogenin 3-O-beta-xylopyranosyl(1-->3)-beta-glucopyranosyl(1-->4)-beta-galactopyr anoside (1), hecogenin 3-O-beta-glucopyranosyl(1-->2)-beta-glucopyranosyl(1-->4)- beta-galactopyranoside (2) and 3-O-[beta-xylopyranosyl(1-->2)-[beta-xylopyranosyl(1-->3)]-beta- glucopyranosyl(1-->4)-[alpha-rhamnopyranosyl(1-->2)]-beta-galactopyranos yl]- 26-O-beta-glucopyranosyl-22-methoxy-(3 beta,5 alpha,25R)-furostan-3,26-diol (3). Structure elucidation was accomplished by 1D and 2D NMR spectra (13C-1H COSY, HMQC, HMBC, 1H-1H COSY, TOCSY, and NOESY), mass spectrometry (FABMS, ESIMS) and chemical methods.

   Phytochemicals and the breakthrough of traditional herbs in the management of sexual dysfunctions.:Int J Androl. 2000;23 Suppl 2:82-4.Adimoelja A.School of medicine 'Hang Tuah' University, Teaching and Naval Hospital,Surabaya, Indonesia.[PMID: 10849504]

 Traditional herbs have been a revolutionary breakthrough in the management of erectile dysfunction and have become known world-wide as an 'instant' treatment. The modern view of the management of erectile dysfunction subscribes to a single etiology, i.e. the mechanism of erection. A large number of pharmacological agents are orally consumed and vasoactive agents inserted intraurethrally or injected intrapenially to regain good erection. Modern phytochemicals have developed from traditional herbs. Phytochemicals focus their mechanism of healing action to the root cause, i.e. the inability to control the proper function of the whole body system. Hence phytochemicals manage erectile dysfunction in the frame of sexual dysfunction as a whole entity. Protodioscin is a phytochemical agent derived from Tribulus terrestris L plant, which has been clinically proven to improve sexual desire and enhance erection via the conversion of protodioscine to DHEA (De-Hydro-Epi-Androsterone). Preliminary observations suggest that Tribulus terrestris L grown on different soils does not consistently produce the active component Protodioscin. Further photochemical studies of many other herbal plants are needed to explain the inconsistent results found with other herbal plants, such as in diversities of Ginseng, Eurycoma longifolia, Pimpinella pruacen, Muara puama, Ginkgo biloba, Yohimbe etc.

   Proerectile pharmacological effects of Tribulus terrestris extract on the rabbit corpus cavernosum.:Ann Acad Med Singapore. 2000 Jan;29(1):22-6.Adaikan PG, Gauthaman K, Prasad RN, Ng SC.Department of Obstetrics & Gynaecology, National University Hospital, National University of Singapore, Singapore. obgadaik@nus.edu.sg.[PMID: 10748960]

 INTRODUCTION: The objective of the present study was to investigate the effect of oral treatment of Tribulus terrestris (TT) extract on the isolated corpus cavernosal tissue of New Zealand white (NZW) rabbits and to determine the mechanism by which protodioscin (PTN), a constituent of the TT, exerts its pharmacological effects. MATERIALS AND METHODS: Twenty-four NZW rabbits were randomly assigned to 4 experimental groups of 6 each. Group I served as control. Groups II to IV were treated with the extract at different dose levels, i.e. 2.5 mg/kg, 5 mg/kg and 10 mg/kg body weight, respectively. The TT extract was administered orally, once daily, for a period of 8 weeks. The rabbits were then sacrificed and their penile tissue isolated to evaluate the responses to both contracting and relaxing pharmacological agents and electrical field stimulation (EFS). RESULTS: PTN on its own had no effect on the isolated corpus cavernosal strips. The relaxant responses to EFS, acetylcholine and nitroglycerin in noradrenaline precontracted tissues from treated groups showed an increase in relaxation of a concentration dependent nature compared to that of the tissues from control group. However, the contractile, anti-erectile response of corpus cavernosal tissue to noradrenaline and histamine showed no significant change between the treatment and the control groups. CONCLUSIONS: The relaxant responses to acetylcholine, nitroglycerin and EFS by more than 10%, 24% and 10% respectively compared to their control values and the lack of such effect on the contractile response to noradrenaline and histamine indicate that PTN has a proerectile activity. The enhanced relaxant effect observed is probably due to increase in the release of nitric oxide from the endothelium and nitrergic nerve endings, which may account for its claims as an aphrodisiac. However, further study is needed to clarify the precise mechanism of its action.

   Steroidal glycosides from Tribulus terrestris.:Phytochemistry. 1996 Aug;42(6):1677-81.Wu G, Jiang S, Jiang F, Zhu D, Wu H, Jiang S.Department of Phytochemistry, Shanghai Institute of Materia Medica, P.R. China.[PMID: 8783840]

 In addition to hecogenin 3-O-beta-D-glucopyranosyl(1--> 4)-beta-D-galactopyranoside, two new steroidal saponins were isolated from the aerial parts of Tribulus terrestris L. On the basis of chemical and spectroscopic evidence, especially 2D NMR spectroscopic techniques, the structures of the new saponins were established as 26-O-beta-D-glucopyranosyl-3-O-[-beta-D-xylopyranosyl(1--> 3)--beta-D-galactopyranosyl(1-->2)--beta-D-glucopyranosyl (1--> 4)-beta-D-glucopyranosyl]-5 alpha-furost-20(22)-en-12-one-3 beta,26-diol and 26-O-beta-D-glucopyranosyl-3-O-[{beta-D-xylopyranosyl (1-->3)--beta-D-galactopyranosyl(1-->2)--beta-D-glucopyranosyl(1 -->4)-beta-D-glucopyranosyl]-5 alpha-furostan-12-one-3 beta,22,26-triol.

   Studies on water soluble polysaccharides isolated from Tribulus terrestris L--purification and preliminary structural determination of heteropolysaccharide H.:Yao Xue Xue Bao. 1991;26(8):578-83.Huang XL, Zhang YS, Liang ZY.Department of Biology, Northeast Normal University, Changchun.[PMID: 1805519]

 Crude polysaccharides extracted from the stem and leaf of Tribulus terristris L after the removal of crude saponins are a mixture of heteropolysaccharides composed of Ara, Rha, Xyl, GalA, Gal, Glc and Man in molar ratios of 6.0:2.1:1:3.6:3.4:7.7:2.9. A homogeneous polysaccharide H obtained by gradation and purification contains Ara, Rha, Xyl, GalA. Gal and Glc. in molar ratios of 1.6:2.4:0.1:3.5:1.3:1. Its molecular weight was found to be 1 x 10(5). By means of pectinase and beta-D-galactosidase enzymolysis, periodate oxidation, Smith degradation, partial hydrolysis with acid, methylation, GC and GC-MS, the H contains alpha-D-GalA (1-4) and L-Rha (1-2) probably linked alternately as main chain with some L-Rha (1-2) side chains.


   406 cases of angina pectoris in coronary heart disease treated with saponin of Tribulus terrestris.:Zhong Xi Yi Jie He Za Zhi. 1990 Feb;10(2):85-7, 68.Wang B, Ma L, Liu T.Research Unit of Cardiovascular Disease, Jilin Medical College.[PMID: 2364467]

 Coronary heart disease (CHD) was treated with saponin of Tribulus terrestris. According to 406 cases of clinical observation and a cross test (67 cases treated with Yufen Ningxin Pian as control), the results showed that the total efficacious rate of remission angina pectoris was 82.3%. It was higher than the control group with a total effective rate of 67.2% (P less than 0.05). The total effective rate of ECG improvement (52.7%) was even higher than that of the control group (35.8%). It is shown that saponin of Tribulus terrestris has the action of dilating coronary artery and improving coronary circulation, and thus has better effects on improving ECG of myocardial ischemia. If taken for a long time, it has no adverse reaction on blood system and hepatic and renal functions. Neither does it have side effects. It is one of the ideal medicines to treat angina pectoris.

   A novel nigrostriatal dopaminergic disorder in sheep affected by Tribulus terrestris staggers.:Res Vet Sci. 1987 Nov;43(3):347-50.Bourke CA.New South Wales Department of Agriculture, Agricultural Research and Veterinary Centre, Australia.[PMID: 3444981]

 An investigation was carried out into the pathogenesis of a unique locomotory disorder of sheep. Thirty sheep which had exhibited clinical signs for more than 15 months were examined for the presence of muscle atrophy, limb paresis, and spontaneous rotational behaviour. A single large dose of levodopa was administered to 12 normal and 12 affected sheep, and the drug-related effects of sedation and excitation were monitored continuously for three hours. The striatum was removed from eight normal and eight affected sheep and assayed for dopamine (DA) and 3,4-dihydroxyphenylacetic acid (DOPAC). The findings of asymmetrical atrophy of pelvic limb extensor muscles, asymmetrical paresis of the limbs, a left:right dominance ratio of 50:50, spontaneous rotational behaviour, decreased response to levodopa loading, and decreased levels of DA (19 per cent reduction) and DOPAC (30 per cent reduction) in the striatum of affected sheep, were interpreted as indicative of a primary nigrostriatal dopaminergic disorder. It is suggested that a striatal presynaptic receptor malfunction has occurred.


   Protodioscin for Hair loss treatment::

 The active ingredient of the herb Tribulus terrestris L., protodioscin has been proven by many clinical studies to help regulate the body's androgen levels and may help in preventing hair loss due to the overproduction of the androgen DHT.

   Structural identification of methyl protodioscin metabolites in rats' urine and their antiproliferative activities against human tumor cell lines.:

 Methyl protodioscin (MPD), a furostanol saponin, is a preclinical drug shown potent antiproliferative activities against most cell lines from leukemia and solid tumors. The metabolites of MPD in rats' urine after single oral doses of 80 mg/kg were investigated in this research. Ten metabolites were isolated and purified by liquid-liquid extraction, open-column chromatography, medium-pressure liquid chromatography, and preparative high-performance liquid chromatography. The structural identification of the metabolites was carried out by high resolution mass spectra, NMR spectroscopic methods including (1)H NMR, (13)C NMR and 2D NMR, as well as chemical ways. The 10 metabolites were elucidated to be dioscin (M-1), pregna-5,16-dien-3beta-ol-20-one-O-alpha-l-rhamnopyranosyl-(1-->2)-[alpha-l-rhamnopyranosyl-(1-->4)]-beta-d-glucopyranoside (M-2), diosgenin (M-3), protobioside (M-4), methyl protobioside (M-5), 26-O-beta-d-glucopyrannosyl(25R)-furan-5-ene-3beta, 22alpha, 26-trihydroxy-3-O-alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranoside(M-6),26-O-beta-d-glucopyranosyl(25R)-furan-5-ene-3beta,26-dihydroxy-22-methoxy-3-O-alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranoside (M-7), prosapogenin A of dioscin (M-8), prosapogenin B of dioscin (M-9), and diosgenin-3-O-beta-d-glucopyranoside (M-10), respectively. M-1 was the main urinary metabolite of MPD in rats. Some metabolites showed potent antiproliferative activities against HepG2, NCI-H460, MCF-7 and HeLa cell lines in vitro.

   Facile conversion of spirostan saponin into furostan saponin: synthesis of methyl protodioscin and its 26-thio-analogue.:

 A facile approach for the conversion of a spirostan saponin into its furostan counterpart, as illustrated by the transformation of dioscin to methyl protodioscin (and its 26-thio-analogue), has been developed.

   Microbial metabolism of methyl protodioscin by Aspergillus niger culture-A new androstenedione producing way from steroid.:

 Methyl protodioscin, a natural furostanol biglycoside steroid, was a preclinical anticancer drug, which showed potent activity against most cell lines from leukemia and solid tumors in the National Cancer Institute's (NCI) human cancer panel. Metabolism of methyl protodioscin by Aspergillus niger was investigated. Seven metabolites were isolated and identified. Two main metabolites were pregnane glycosides and four were furostanol glycosides, together with the aglycone. It was found that steroidal saponin skeleton could be converted to pregnenolone skeleton only using microbial methods, which must have chemical procedures in the reported literatures. The proposed biosynthetic pathways of the microbial conversion products of methyl protodioscin were drawn. The found enriched the reaction types of microbial bioconversion and provided a new producing way of androstenedione from steroid. Most metabolites showed strong cytotoxic activities against HepG2, NCI-H460, HeLa, and MCF-7 cell lines.
 

   Methyl protodioscin induces G2/M cell cycle arrest and apoptosis in HepG2 liver cancer cells.:

 Methyl protodioscin (NSC-698790) is one of the main bioactive components in the traditional Chinese medicine Dioscorea collettii var. hypoglauca (Dioscoreaceae). In this study, we investigated the anti-proliferative effect of methyl protodioscin on the HepG2 cells and the mechanism of the induced cytotoxicity. Treatment of methyl protodioscin resulted in G2/M arrest and apoptosis in HepG2 cells. These effects were attributed to down-regulation of Cyclin B1 and the signaling pathways leading to up-regulation of Bax and down-regulation of BCL2, suggesting that methyl protodioscin may be a novel anti-mitotic agent.


   A new steroidal saponin from Dioscorea cayenensis.:

 The new 26-O-beta-D-glucopyranosyl-3beta,26-dihydroxy-20,22-seco-25(R)-furost-5-en-20,22-dione-3-O-alpha-L-rhamnopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside (1), along with the known methyl protodioscin (2), asperoside (3) and prosapogenin A of dioscin (4) were isolated from the rhizomes of Dioscorea cayenensis LAM.-HOLL (Dioscoreaceae). Their structures were established mainly on the basis of 600 MHz 2D-NMR spectral data. 4 exhibited antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata and C. tropicalis (MICs of 20.8, 6.25, 25 microg/ml, respectively), whereas saponins 1-3 were inactive.

   Steroidal saponins from Dioscorea panthaica and their cytotoxic activity.:

 A new steroidal saponin, dioscoreside E (1), and a known compound, protodioscin (2), were isolated from an ethanol extract of the rhizomes of Dioscorea panthaica. The structure of 1 was established as 3-O-[bis-alpha-L-rhamnopyranosyl-(1 --> 2 and 1 --> 4)-beta-D-glucopyranosyl]-26-O-beta-D-glucopyranosyl-20(R)-methoxy-25(R)-furosta-5,22(23)-diene-3beta,26-diol, on the basis of spectral and chemical evidence. Compounds 1 and 2 showed cytotoxic activity against a panel of tumor cell lines.

   Quantification of protodioscin and rutin in asparagus shoots by LC/MS and HPLC methods.:

 A liquid chromatography/mass spectrometry (LC/MS) method with selected ion monitoring was developed and validated to analyze the contents of protodioscin and rutin in asparagus. The distribution of rutin and protodioscin within the shoots was found to vary by location, with the tissue closest to the rhizome found to be a rich source of protodioscin, at an average level of 0.025% tissue fresh weight in the three tested lines, while the upper youngest shoot tissue contained the highest amount of rutin at levels of 0.03-0.06% tissue fresh weight. The lower portions of the asparagus shoots that are discarded during grading and processing should instead be considered a promising source of a new value-added nutraceutical product.

   Protodioscin (NSC-698 796): its spectrum of cytotoxicity against sixty human cancer cell lines in an anticancer drug screen panel.:

 Protodioscin (NSC-698 796) is a furostanol saponin isolated from the rhizome of Dioscorea collettii var. hypoglauca (Dioscoreaceae), a Chinese herbal remedy for the treatment of cervical carcinoma, carcinoma of urinary bladder and renal tumor for centuries. To systematically evaluate its potential anticancer activity, protodioscin was tested for cytotoxicity in vitro against 60 human cancer cell lines in the NCI's (National Cancer Institute, USA) anticancer drug screen. As a result, protodioscin was cytotoxic against most cell lines from leukemia and solid tumors in the NCI's human cancer panel, especially selectively against one leukemia line (MOLT-4), one NSCLC line (A549/ATCC), two colon cancer lines (HCT-116 and SW-620), one CNS cancer line (SNB-75), one melanoma line (LOX IMVI), and one renal cancer line (786 - 0) with GI50 < or = 2.0 microM. In the general view of mean graphs, leukemia, colon cancer and prostate cancer are the most sensitive subpanels, while ovarian cancer is the least sensitive subpanel. Based on an analysis of COMPARE computer program with protodioscin as a seed compound, no compounds in the NCI's anticancer drug screen database have cytotoxicity patterns (mean graphs) similar to those of protodioscin, indicating that a potential novel mechanism of anticancer action is involved.

   Determination of steroidal saponins in Tribulus terrestris by reversed-phase high-performance liquid chromatography and evaporative light scattering detection.:

 This paper describes the first analytical method suitable for the determination of steroidal saponins in Tribulus terrestris. A separation by high performance liquid chromatography (HPLC) was achieved by using a reversed-phase (RP-18) column, evaporative light scattering (ELS) detection, and a water/acetonitrile gradient as the mobile phase. The marker compound, protodioscin, was detected at a concentration as low as 10.0 microg/mL. Several different samples of plant material were successfully analyzed, and depending on origin and plant part used for extraction, significant differences in the composition of the saponins were observed. The analysis of market products showed considerable variations of 0.17 to 6.49% in the protodioscin content.


   Aphrodisiac properties of Tribulus Terrestris extract (Protodioscin) in normal and castrated rats.:Gauthaman K , Adaikan PG , Prasad RN.Source:Life Sci, 71(12): 1385-96 2002

 Tribulus terrestris (TT) has long been used in the traditional Chinese and Indian systems of medicine for the treatment of various ailments and is popularly claimed to improve sexual functions in man. Sexual behaviour and intracavernous pressure (ICP) were studied in both normal and castrated rats to further understand the role of TT containing protodioscin (PTN) as an aphrodisiac. Adult Sprague-Dawley rats were divided into five groups of 8 each that included distilled water treated (normal and castrated), testosterone treated (normal and castrated, 10 mg/kg body weight, subcutaneously, bi-weekly) and TT treated (castrated, 5 mg/kg body weight, orally once daily). Decreases in body weight, prostate weight and ICP were observed among the castrated groups of rats compared to the intact group. There was an overall reduction in the sexual behaviour parameters in the castrated groups of rats as reflected by decrease in mount and intromission frequencies (MF and IF) and increase in mount, intromission, ejaculation latencies (ML, IL, EL) as well as post-ejaculatory interval (PEI). Compared to the castrated control, treatment of castrated rats (with either testosterone or TT extract) showed increase in prostate weight and ICP that were statistically significant. There was also a mild to moderate improvement of the sexual behaviour parameters as evidenced by increase in MF and IF; decrease in ML, IL and PEI. These results were statistically significant. It is concluded that TT extract appears to possess aphrodisiac activity probably due to androgen increasing property of TT (observed in our earlier study on primates).

   Proerectile pharmacological effects of Tribulus terrestris extract on the rabbit corpus cavernosum.:Adaikan PG , Gauthaman K , Prasad RN , Ng SC.Source:Ann Acad Med Singapore, 29(1): 22-6 2000

 INTRODUCTION: The objective of the present study was to investigate the effect of oral treatment of Tribulus terrestris (TT) extract on the isolated corpus cavernosal tissue of New Zealand white (NZW) rabbits and to determine the mechanism by which protodioscin (PTN), a constituent of the TT, exerts its pharmacological effects. MATERIALS AND METHODS: Twenty-four NZW rabbits were randomly assigned to 4 experimental groups of 6 each. Group I served as control. Groups II to IV were treated with the extract at different dose levels, i.e. 2.5 mg/kg, 5 mg/kg and 10 mg/kg body weight, respectively. The TT extract was administered orally, once daily, for a period of 8 weeks. The rabbits were then sacrificed and their penile tissue isolated to evaluate the responses to both contracting and relaxing pharmacological agents and electrical field stimulation (EFS). RESULTS: PTN on its own had no effect on the isolated corpus cavernosal strips. The relaxant responses to EFS, acetylcholine and nitroglycerin in noradrenaline precontracted tissues from treated groups showed an increase in relaxation of a concentration dependent nature compared to that of the tissues from control group. However, the contractile, anti-erectile response of corpus cavernosal tissue to noradrenaline and histamine showed no significant change between the treatment and the control groups. CONCLUSIONS: The relaxant responses to acetylcholine, nitroglycerin and EFS by more than 10%, 24% and 10% respectively compared to their control values and the lack of such effect on the contractile response to noradrenaline and histamine indicate that PTN has a proerectile activity. The enhanced relaxant effect observed is probably due to increase in the release of nitric oxide from the endothelium and nitrergic nerve endings, which may account for its claims as an aphrodisiac. However, further study is needed to clarify the precise mechanism of its action.

   Phytochemicals and the breakthrough of traditional herbs in the management of sexual dysfunctions.:Adimoelja A.Source:Int J Androl, 23 Suppl 2(): 82-4 2000

 Traditional herbs have been a revolutionary breakthrough in the management of erectile dysfunction and have become known world-wide as an 'instant' treatment. The modern view of the management of erectile dysfunction subscribes to a single etiology, i.e. the mechanism of erection. A large number of pharmacological agents are orally consumed and vasoactive agents inserted intraurethrally or injected intrapenially to regain good erection. Modern phytochemicals have developed from traditional herbs. Phytochemicals focus their mechanism of healing action to the root cause, i.e. the inability to control the proper function of the whole body system. Hence phytochemicals manage erectile dysfunction in the frame of sexual dysfunction as a whole entity. Protodioscin is a phytochemical agent derived from Tribulus terrestris L plant, which has been clinically proven to improve sexual desire and enhance erection via the conversion of protodioscine to DHEA (De-Hydro-Epi-Androsterone). Preliminary observations suggest that Tribulus terrestris L grown on different soils does not consistently produce the active component Protodioscin. Further photochemical studies of many other herbal plants are needed to explain the inconsistent results found with other herbal plants, such as in diversities of Ginseng, Eurycoma longifolia, Pimpinella pruacen, Muara puama, Ginkgo biloba, Yohimbe etc.

   Protodioscin (NSC-698 796): its spectrum of cytotoxicity against sixty human cancer cell lines in an anticancer drug screen panel.:Hu K , Yao X.Source:Planta Med, 68(4): 297-301 2002

 Protodioscin (NSC-698 796) is a furostanol saponin isolated from the rhizome of Dioscorea collettii var. hypoglauca (Dioscoreaceae), a Chinese herbal remedy for the treatment of cervical carcinoma, carcinoma of urinary bladder and renal tumor for centuries. To systematically evaluate its potential anticancer activity, protodioscin was tested for cytotoxicity in vitro against 60 human cancer cell lines in the NCI's (National Cancer Institute, USA) anticancer drug screen. As a result, protodioscin was cytotoxic against most cell lines from leukemia and solid tumors in the NCI's human cancer panel, especially selectively against one leukemia line (MOLT-4), one NSCLC line (A549/ATCC), two colon cancer lines (HCT-116 and SW-620), one CNS cancer line (SNB-75), one melanoma line (LOX IMVI), and one renal cancer line (786 - 0) with GI50 < or = 2.0 microM. In the general view of mean graphs, leukemia, colon cancer and prostate cancer are the most sensitive subpanels, while ovarian cancer is the least sensitive subpanel. Based on an analysis of COMPARE computer program with protodioscin as a seed compound, no compounds in the NCI's anticancer drug screen database have cytotoxicity patterns (mean graphs) similar to those of protodioscin, indicating that a potential novel mechanism of anticancer action is involved.

   Determination of steroidal saponins in Tribulus terrestris by reversed-phase high-performance liquid chromatography and evaporative light scattering detection.:Ganzera M , Bedir E , Khan IA.Source:J Pharm Sci, 90(11): 1752-8 2001

 This paper describes the first analytical method suitable for the determination of steroidal saponins in Tribulus terrestris. A separation by high performance liquid chromatography (HPLC) was achieved by using a reversed-phase (RP-18) column, evaporative light scattering (ELS) detection, and a water/acetonitrile gradient as the mobile phase. The marker compound, protodioscin, was detected at a concentration as low as 10.0 microg/mL. Several different samples of plant material were successfully analyzed, and depending on origin and plant part used for extraction, significant differences in the composition of the saponins were observed. The analysis of market products showed considerable variations of 0.17 to 6.49% in the protodioscin content.


   Two new sulfated furostanol saponins from Tribulus terrestris.:Kostova I , Dinchev D , Rentsch GH , Dimitrov V , Ivanova A;Source:Z Naturforsch [C], 57(1-2): 33-8 0

 The known furostanol saponins methylprotodioscin and protodioscin and two new sulfated saponins, sodium salt of 26-O-beta-glucopyranosyl-22alpha-methoxy-(25R)-furost-5-ene-3beta,26-diol-3-O-alpha-rhamnopyranosyl-(1-->2)-beta-4-O-sulfo-glucopyranoside (methylprototribestin) and sodium salt of 26-O-beta-glucopyranosyl-22alpha-hydroxy-(25R)-furost-5-ene-3beta,26-diol-3-O-alpha-rhamnopyranosyl-(1-->2)-beta-4-O-sulfo-glucopyranoside (prototribestin) have been isolated from the aerial parts of Tribulus terrestris L. growing in Bulgaria. The structures of the new compounds were elucidated on the basis of 1D and 2D (DQF-COSY, TOCSY, HSQC-TOCSY, HSQC, HMBC, ROESY) NMR data, ESI mass spectra and chemical transformation.

   Phytochemicals and the breakthrough of traditional herbs in the management of sexual dysfunctions.:Adimoelja A,Source:Int J Androl, 23 Suppl 2(): 82-4 2000

 Traditional herbs have been a revolutionary breakthrough in the management of erectile dysfunction and have become known world-wide as an 'instant' treatment. The modern view of the management of erectile dysfunction subscribes to a single etiology, i.e. the mechanism of erection. A large number of pharmacological agents are orally consumed and vasoactive agents inserted intraurethrally or injected intrapenially to regain good erection. Modern phytochemicals have developed from traditional herbs. Phytochemicals focus their mechanism of healing action to the root cause, i.e. the inability to control the proper function of the whole body system. Hence phytochemicals manage erectile dysfunction in the frame of sexual dysfunction as a whole entity. Protodioscin is a phytochemical agent derived from Tribulus terrestris L plant, which has been clinically proven to improve sexual desire and enhance erection via the conversion of protodioscine to DHEA (De-Hydro-Epi-Androsterone). Preliminary observations suggest that Tribulus terrestris L grown on different soils does not consistently produce the active component Protodioscin. Further photochemical studies of many other herbal plants are needed to explain the inconsistent results found with other herbal plants, such as in diversities of Ginseng, Eurycoma longifolia, Pimpinella pruacen, Muara puama, Ginkgo biloba, Yohimbe etc.

   Quantification of protodioscin and rutin in asparagus shoots by LC/MS and HPLC methods.:

 J Agric Food Chem. 2003; 51(21):6132-6 (ISSN: 0021-8561).Wang M; Tadmor Y; Wu QL; Chin CK; Garrison SA; Simon JE.New Use Agriculture and Natural Plant Products Program and Department of Plant Biology and Pathology, Cook College, Rutgers University, and New Jersey Agricultural Experiment Station, New Brunswick, New Jersey 08901, USA. mwang@aesop.rutgers.edu

 A liquid chromatography/mass spectrometry (LC/MS) method with selected ion monitoring was developed and validated to analyze the contents of protodioscin and rutin in asparagus. The distribution of rutin and protodioscin within the shoots was found to vary by location, with the tissue closest to the rhizome found to be a rich source of protodioscin, at an average level of 0.025% tissue fresh weight in the three tested lines, while the upper youngest shoot tissue contained the highest amount of rutin at levels of 0.03-0.06% tissue fresh weight. The lower portions of the asparagus shoots that are discarded during grading and processing should instead be considered a promising source of a new value-added nutraceutical product.

   Protodioscin isolated from fenugreek (Trigonella foenumgraecum L.) induces cell death and morphological change indicative of apoptosis in leukemic cell line H-60, but not in gastric cancer cell line KATO III.:Int J Mol Med. 2003; 11(1):23-6 (ISSN: 1107-3756)

 Protodioscin (PD) was purified from fenugreek (Trigonella foenumgraecum L.) and identified by Mass, and 1H- and 13C-NMR. The effects of PD on cell viability in human leukemia HL-60 and human stomach cancer KATO III cells were investigated. PD displayed strong growth inhibitory effect against HL-60 cells, but weak growth inhibitory effect on KATO III cells. Morphological change showing apoptotic bodies was observed in the HL-60 cells treated with PD, but not in KATO III cells treated with PD. Flow cytometric analysis showed that the hypodiploid nuclei of HL-60 cells were increased to 75.2, 96.3, and 100% after a 3-day treatment with 2.5, 5, and 10 microM PD, respectively. The fragmentation by PD of DNA to oligonucleosomal-sized fragments, that is a characteristic of apoptosis, was observed to be both concentration- and time-dependent in the HL-60 cells. These findings suggest that growth inhibition by PD of HL-60 cells results from the induction of apoptosis by this compound in HL-60 cells.

   Sexual effects of puncturevine (Tribulus terrestris) extract (protodioscin): an evaluation using a rat model.:

 J Altern Complement Med. 2003; 9(2):257-65 (ISSN: 1075-5535).Gauthaman K; Ganesan AP; Prasad RN.Department of Obstetrics and Gynaecology, National University Hospital, National University of Singapore, Singapore.

 OBJECTIVE: Apart from its claims for improvement of sexual functions in men, the puncturevine plant (Tribulus terrestris: TT) has long been considered as an energizer and vitalizer in the indigenous system of medicine. Sexual behavior and intracavernous pressure (ICP) measurements were taken in rats to scientifically validate the claim of TT [containing protodioscin (PTN)] as an aphrodisiac. MATERIALS AND METHODS: Forty sexually mature male Sprague-Dawley rats were randomly divided into four groups of 10 each. Group I served as a control group and groups II, III, and IV were treated with three different doses of TT extract (2.5, 5 and 10 mg/kg body weight, respectively), orally, once daily for 8 weeks. Weight was recorded and the rats from all four groups were subjected to sexual behavior studies with primed females and various parameters namely mount and intromission frequencies (MF and IF, respectively), mount, intromission and ejaculation latencies (ML, IL, and EL, respectively) as well as postejaculatory interval (PEI) were recorded. In addition, blood pressure and ICP were recorded for all rats at the end of study. RESULTS: Increases in body weight (by 9, 23, and 18% for groups II, III & IV) and ICP (by 43% and 26% for groups III and IV) were statistically significant compared to the control group. Increases in MF (by 27% and 24%) and IF (by 19% and 22%) for the groups III and IV were statistically significant. Decreases in ML (by 16%, 23%, and 22% for groups II, III, and IV) and PEI (by 20% for group III) were statistically significant compared to the control. CONCLUSIONS: The weight gain and improvement in sexual behavior parameters observed in rats could be secondary to the androgen increasing property of TT (PTN) that was observed in our earlier study on primates. The increase in ICP which confirms the proerectile aphrodisiac property of TT could possibly be the result of an increase in androgen and subsequent release of nitric oxide from the nerve endings innervating the corpus cavernosum.


   Protodioscin (NSC-698 796): its spectrum of cytotoxicity against sixty human cancer cell lines in an anticancer drug screen panel.:

 Planta Med. 2002; 68(4):297-301 (ISSN: 0032-0943).Hu K; Yao X.Department of Pharmaceutical Sciences, School of Pharmacy, State University of New York at Buffalo, Buffalo, New York 14260, USA. kehu@ascu.buffalo.edu

 Protodioscin (NSC-698 796) is a furostanol saponin isolated from the rhizome of Dioscorea collettii var. hypoglauca (Dioscoreaceae), a Chinese herbal remedy for the treatment of cervical carcinoma, carcinoma of urinary bladder and renal tumor for centuries. To systematically evaluate its potential anticancer activity, protodioscin was tested for cytotoxicity in vitro against 60 human cancer cell lines in the NCI's (National Cancer Institute, USA) anticancer drug screen. As a result, protodioscin was cytotoxic against most cell lines from leukemia and solid tumors in the NCI's human cancer panel, especially selectively against one leukemia line (MOLT-4), one NSCLC line (A549/ATCC), two colon cancer lines (HCT-116 and SW-620), one CNS cancer line (SNB-75), one melanoma line (LOX IMVI), and one renal cancer line (786 - 0) with GI50 < or = 2.0 microM. In the general view of mean graphs, leukemia, colon cancer and prostate cancer are the most sensitive subpanels, while ovarian cancer is the least sensitive subpanel. Based on an analysis of COMPARE computer program with protodioscin as a seed compound, no compounds in the NCI's anticancer drug screen database have cytotoxicity patterns (mean graphs) similar to those of protodioscin, indicating that a potential novel mechanism of anticancer action is involved.

   Aphrodisiac properties of Tribulus Terrestris extract (Protodioscin) in normal and castrated rats.:

 Life Sci. 2002; 71(12):1385-96 (ISSN: 0024-3205).Gauthaman K; Adaikan PG; Prasad RN.Department of Obstetrics and Gynaecology, National University Hospital, National University of Singapore, Singapore 119704, Singapore.

 Tribulus terrestris (TT) has long been used in the traditional Chinese and Indian systems of medicine for the treatment of various ailments and is popularly claimed to improve sexual functions in man. Sexual behaviour and intracavernous pressure (ICP) were studied in both normal and castrated rats to further understand the role of TT containing protodioscin (PTN) as an aphrodisiac. Adult Sprague-Dawley rats were divided into five groups of 8 each that included distilled water treated (normal and castrated), testosterone treated (normal and castrated, 10 mg/kg body weight, subcutaneously, bi-weekly) and TT treated (castrated, 5 mg/kg body weight, orally once daily). Decreases in body weight, prostate weight and ICP were observed among the castrated groups of rats compared to the intact group. There was an overall reduction in the sexual behaviour parameters in the castrated groups of rats as reflected by decrease in mount and intromission frequencies (MF and IF) and increase in mount, intromission, ejaculation latencies (ML, IL, EL) as well as post-ejaculatory interval (PEI). Compared to the castrated control, treatment of castrated rats (with either testosterone or TT extract) showed increase in prostate weight and ICP that were statistically significant. There was also a mild to moderate improvement of the sexual behaviour parameters as evidenced by increase in MF and IF; decrease in ML, IL and PEI. These results were statistically significant. It is concluded that TT extract appears to possess aphrodisiac activity probably due to androgen increasing property of TT (observed in our earlier study on primates).

   Study on chemical constituents in total saponin from Trigonella foenum-graecum.:

 Zhongguo Zhong Yao Za Zhi. 2005; 30(18):1428-30 (ISSN: 1001-5302).Yang WX; Huang HY; Wang YJ; Jia ZY; Li LL.Changji Medical School, Changji 831100, China. ywxyt@163.com

 OBJECTIVE: To study the chemical constituents in the total saponin from Trigonellf foenum-graecum. METHOD: The compounds were isolated by column chromatography on macroporous resin and silica gel and elucidated by physical and chemical evidences and spectroscopic analysis. RESULT: Two compounds were obtained and identifiedas methyl-protodioscin and methyl-protodeltonin. CONCLUSION: Methyl-protodioscin and methyl-protodeltonin were isolated from this plant for the first time.

   A new steroidal saponin from Dioscorea cayenensis.:

 Chem Pharm Bull. 2004; 52(11):1353-5 (ISSN: 0009-2363).Sautour M; Mitaine-Offer AC; Miyamoto T; Dongmo A; Lacaille-Dubois MA.Laboratoire de Pharmacognosie, Unit?? UMIB, EA 3660, Facult?? de Pharmacie, Universit?? de Bourgogne, 7 Boulevard Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France.

 The new 26-O-beta-D-glucopyranosyl-3beta,26-dihydroxy-20,22-seco-25(R)-furost-5-en-20,22-dione-3-O-alpha-L-rhamnopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside (1), along with the known methyl protodioscin (2), asperoside (3) and prosapogenin A of dioscin (4) were isolated from the rhizomes of Dioscorea cayenensis LAM.-HOLL (Dioscoreaceae). Their structures were established mainly on the basis of 600 MHz 2D-NMR spectral data. 4 exhibited antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata and C. tropicalis (MICs of 20.8, 6.25, 25 microg/ml, respectively), whereas saponins 1-3 were inactive.

   Steroidal saponins from Dioscorea panthaica and their cytotoxic activity.:

 Pharmazie. 2004; 59(4):294-6 (ISSN: 0031-7144).Dong M; Feng XZ; Wang BX; Ikejima T; Wu LJ.Department of Cell Biology, Neurobiology, and Anatomy, University of Cincinnati, Ohio, USA.

 A new steroidal saponin, dioscoreside E (1), and a known compound, protodioscin (2), were isolated from an ethanol extract of the rhizomes of Dioscorea panthaica. The structure of 1 was established as 3-O-[bis-alpha-L-rhamnopyranosyl-(1 --> 2 and 1 --> 4)-beta-D-glucopyranosyl]-26-O-beta-D-glucopyranosyl-20(R)-methoxy-25(R)-furosta-5,22(23)-diene-3beta,26-diol, on the basis of spectral and chemical evidence. Compounds 1 and 2 showed cytotoxic activity against a panel of tumor cell lines.


   Furostanol saponins from Tribulus terrestris.:

 Fitoterapia. 2003; 74(6):583-91 (ISSN: 0367-326X).De Combarieu E; Fuzzati N; Lovati M; Mercalli E.Research and Development Laboratories, Indena SpA, Via Don Minzoni 6, Settala (MI) 20090, Italy.

 An HPLC-ELSD-ESI-MS method has been developed for the analysis of the steroidal saponins in the aerial parts of Tribulus terrestris. Protodioscin, a new saponin (5,6-dihydroprotodioscin, neoprotodioscin) and their respective sulfates were detected. The structure of the new compound was elucidated on the basis of NMR and ESI-MS spectral analysis.

   Isolation and identification of steroidal saponins in Taiwanese yam cultivar (Dioscorea pseudojaponica Yamamoto).:

 J Agric Food Chem. 2003; 51(22):6438-44 (ISSN: 0021-8561).Yang DJ; Lu TJ; Hwang LS.Graduate Institute of Food Science and Technology, National Taiwan University, 59 Lane 144, Keelung Road, Sec. 4, Taipei, Taiwan 106, Republic of China.

 A new furostanol pentaoligoside and spirostanol tetraoligoside were isolated for the first time from yam tubers (Dioscorea pseudojaponica Yamamoto) from Taiwan, together with four known yam saponins, methyl protodioscin, methyl protogracillin, dioscin, and gracillin. Their structures were characterized as 26-O-beta-D-glucopyranosyl-22alpha-methoxyl-(25R)-furost-5-en-3beta,26-diol, 3-O-alpha-L-rhamnopyranosyl-(1-->2)-O-([alpha-L-rhamnopyranosyl-(1-->4)]-O-[alpha-L-rhamnopyranosyl-(1-->4)])-beta-D-glucopyranoside, and (25R)-spirost-5-en-3beta-ol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-O-([alpha-L-rhamnopyranosyl-(1-->4)]-O-[alpha-L-rhamnopyranosyl-(1-->4)])-beta-D-glucopyranoside. The structural identification was performed using LC-MS and 1H and 13C NMR. The methanol extract of yam tubers was fractionated by XAD-2 column chromatography using a methanol/water gradient elution system to yield furostanol and spirostanol glycoside fractions. Preparative high-performance liquid chromatography, employing a C18 column and a mobile phase of methanol/water (69:31, v/v), was used to separate each furostanol glycoside, whereas a mobile phase of methanol/water (79:21, v/v) was used to resolve the individual spirostanol glycosides. The conversions from steroid saponins to diosgenin after acid hydrolysis were around 68 and 90% for furostanol and spirostanol glycosides, respectively.

   Determination of steroidal saponins in Tribulus terrestris by reversed-phase high-performance liquid chromatography and evaporative light scattering detection.:

 J Pharm Sci. 2001; 90(11):1752-8 (ISSN: 0022-3549).Ganzera M; Bedir E; Khan IA.National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, University, Mississippi 38677, USA.

 This paper describes the first analytical method suitable for the determination of steroidal saponins in Tribulus terrestris. A separation by high performance liquid chromatography (HPLC) was achieved by using a reversed-phase (RP-18) column, evaporative light scattering (ELS) detection, and a water/acetonitrile gradient as the mobile phase. The marker compound, protodioscin, was detected at a concentration as low as 10.0 microg/mL. Several different samples of plant material were successfully analyzed, and depending on origin and plant part used for extraction, significant differences in the composition of the saponins were observed. The analysis of market products showed considerable variations of 0.17 to 6.49% in the protodioscin content.

   Phytochemicals and the breakthrough of traditional herbs in the management of sexual dysfunctions.:

 Int J Androl. 2000; 23 Suppl 2:82-4 (ISSN: 0105-6263).Adimoelja A.School of medicine 'Hang Tuah' University, Teaching and Naval Hospital,Surabaya, Indonesia.

 Traditional herbs have been a revolutionary breakthrough in the management of erectile dysfunction and have become known world-wide as an 'instant' treatment. The modern view of the management of erectile dysfunction subscribes to a single etiology, i.e. the mechanism of erection. A large number of pharmacological agents are orally consumed and vasoactive agents inserted intraurethrally or injected intrapenially to regain good erection. Modern phytochemicals have developed from traditional herbs. Phytochemicals focus their mechanism of healing action to the root cause, i.e. the inability to control the proper function of the whole body system. Hence phytochemicals manage erectile dysfunction in the frame of sexual dysfunction as a whole entity. Protodioscin is a phytochemical agent derived from Tribulus terrestris L plant, which has been clinically proven to improve sexual desire and enhance erection via the conversion of protodioscine to DHEA (De-Hydro-Epi-Androsterone). Preliminary observations suggest that Tribulus terrestris L grown on different soils does not consistently produce the active component Protodioscin. Further photochemical studies of many other herbal plants are needed to explain the inconsistent results found with other herbal plants, such as in diversities of Ginseng, Eurycoma longifolia, Pimpinella pruacen, Muara puama, Ginkgo biloba, Yohimbe etc.

   Steroidal saponins from Asparagus officinalis and their cytotoxic activity.:

 Planta Med. 1997; 63(3):258-62 (ISSN: 0032-0943).Shao Y; Poobrasert O; Kennelly EJ; Chin CK; Ho CT; Huang MT; Garrison SA; Cordell GA.Department of Plant Science, Cook College, Rutgers, State University of New Jersey, New Brunswick 08903, USA.

 Two oligofurostanosides were isolated from the seeds of Asparagus officinalis L and their structures characterized as 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-(alpha-L-rhamnopyranosyl- (1-->4))-beta-D-glucopyranosyl]-26-O-[beta-D-glucopyranosyl]-(25R) -22 alpha-methoxyfurost-5-ene-3 beta,26-diol(methyl protodioscin) and its corresponding 22 alpha-hydroxy analogue (protodioscin). The structural identification was performed using detailed analysis of 1H- and 13C-NMR spectra including two-dimensional NMR spectroscopy (COSY, HMQC, NOESY and HMBC), and chemical conversions. These two compounds have been shown to inhibit the growth of human leukemia HL-60 cells in culture and macromolecular synthesis in a dose-dependent manner. The inhibitory effect on DNA synthesis was found to be irreversible.


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  Scientific References:

  1.Tribulus terrestris and Saponins?
  2.Research update of Tribulus Terrestris.