Phytochemistry Reviews

, Volume 4, Issue 2–3, pp 111–137 | Cite as

Saponins in Tribulus terrestris – Chemistry and Bioactivity

  • I. KostovaEmail author
  • D. Dinchev


Tribulus terrestris is a valuable herb known for its application in the folk medicine in many parts of the world. Furostanol and spirostanol saponins of tigogenin, neotigogenin, gitogenin, neogitogenin, hecogenin, neohecogenin, diosgenin, chlorogenin, ruscogenin and sarsasapogenin type are frequently found in this plant. Four sulphated saponins of tigogenin and diosgenin type are also isolated. Extracts and steroidal saponins have been found to possess various pharmacological activities. Preparations based on the saponin fraction of T. terrestris are used for treatment of infertility and libido disorders in men and women, as well as for treatment of cardiac diseases. Food supplements containing T. terrestris extracts are on sale in USA and Europe with claim of a general stimulating action.

Key words

biological activity furostanol saponins spirostanol saponins steroidal saponins Tribulus terrestris 

















South Africa




Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Adaikan, PG, Gauthman, K, Prasad, RN, Ng, SC 2000Proerectile pharmacological effects of Tribulus terrestris on the rabit corpus cavernosumAnn. Acad. Med. Singapore292226PubMedGoogle Scholar
  2. Adaikan, PG, Gauthman, K, Prasad, RNV 2001History of herbal medicine with an insight on the pharmacological properties of Tribulus terrestrisThe Aging Male4163169Google Scholar
  3. Adimoelja, A 2000Phytochemicals and the breakthrough of of traditional herb in the management of sexual disfunctionInt. J. Androl.238284CrossRefPubMedGoogle Scholar
  4. Adimoelja, A, Adaikan, PG 1997Protodioscin from herbal plant Tribulus terrestris L. improves the male sexual functions, probably via DHEAInt. J. Impotence Res.9115Google Scholar
  5. Agrawal, PK, Jain, DC, Gupta, RK, Takur, RS 1985Carbon-13 NMR spectroscopy of steroidal sapogenins and steroidal saponinsPhytochemistry2424792496CrossRefGoogle Scholar
  6. Agrawal, PK 2004Spectral assignment and reference data dependence of 1H NMR chemical shifts of geminal protons of glycosyloxy methylene (H2-26) on the orientation of the 27-methyl group of furostane-type steroidal saponinsMagn. Reson. Chem.42990993CrossRefPubMedGoogle Scholar
  7. Ali, NA, Julich, WD, Kusnick, C, Lindequist, U 2001Screening of Yemeni medicinal plants for antibacterial and cytotoxic activitiesJ. Ethnopharmacol.741739CrossRefPubMedGoogle Scholar
  8. Anand, R, Patnaik, GK, Kulshreshtha, DK, Dhawan, BN 1994Activity of certain fractions of Tribulus terrestris fruits against experimentally induced urolithiasis in ratsIndian J. Exp. Biol.32548552PubMedGoogle Scholar
  9. Arcasoy, HB, Erenmemisoglu, A, Tekol, Y, Kurucu, S, Kartal, M 1998Effect of Tribulus terrestris L. saponin mixture on smooth muscle preparations: a preliminary studyBoll. Chim. Farm.137473475PubMedGoogle Scholar
  10. Arsyad, KM 1996Effect of protodioscin on the quantity and quality of sperms from males with moderate idiopathic oligozoospermiaMedica22614618Google Scholar
  11. Bedir, E, Khan, IA 2000New steroidal glycosides from the fruits of Tribulus terrestrisJ. Nat. Prod.6316991701CrossRefPubMedGoogle Scholar
  12. Bedir, E, Khan, IA, Walker, LA 2002Biologically active steroidal glycosides from Tribulus terrestrisPharmazie57491493PubMedGoogle Scholar
  13. Bombardelli E, Morazzoni P, Riva A & Seghizzi R (2003a) PCT Int. Appl. WO 0394, 943 (Cl. A61K35/78), 20 Nov 2003, IT Appl. 2002/MI 990, 10 May 2002.Google Scholar
  14. Bombardelli E, Morazzoni P, Riva A & Seghizzi R (2003b) PCT Int. Appl. WO 0394, 944 (Cl. A61K35/78), 20 Nov 2003, IT Appl. 2002/MI 994, 10 May 2002.Google Scholar
  15. Bourke, CA, Stevens, GR, Carrigan, MJ 1992Locomotor effects in sheep of alkaloids identified in Australian Tribulus terrestrisAust. Vet. J.69163165PubMedGoogle Scholar
  16. Brown, AG, Vukovich, MD, Martini, ER, Kohut, ML, Franke, WD, Jackson, DA, King, DS 2002Endocrine and lipid responses to chronic androstenediol – herbal supplementation in 30 to 58 year old menJ. Am. Coll. Nutr.20520528Google Scholar
  17. Brown, JM, De Kock, WT 1959Chemical and physiological investigation of geeldikkop in sheep in South AfricaSouth African Ind. Chem.13189191 Chem Abstr 1960; 54: 9012bGoogle Scholar
  18. Cai, LE, Jing, FY, Zhang, JG, Pei, FK, Xu, XJ, Lui, SY, Xu, DM 1999Studies on the chemical components of Tribulus terrestrisYaoxue Xuebao34759761Google Scholar
  19. Cai, L, Wu, Y, Zhang, J, Pei, F, Xu, Y, Xie, S, Xu, D 2001Steroidal saponins from Tribulus terrestrisPlanta Med.67196198CrossRefPubMedGoogle Scholar
  20. Chiang, HC, Tseng, TH, Wang, CJ, Chen, CF, Kan, WS 1991Experimental antitumor agents from Solanium indicum LAnticancer Res.1119111917PubMedGoogle Scholar
  21. Chopra, RN, Nayar, SL, Chopra, IC 1956Glossary of Indian␣Medicinal PlantsCouncil of Scientific & Industrial ResearchNew Delhipp. 246247Google Scholar
  22. Chu, S, Qu, W, Pang, X, Sun, B, Huang, X 2003Effect of saponin from Tribulus terrestris on hyperlipidemiaZhong Yao Cai26341344PubMedGoogle Scholar
  23. Conrad, J, Dinchev, D, Klaiber, I, Mika, S, Kostova, I, Kraus, W 2004A novel furostanol saponin from Tribulus terrestris of Bulgarian originFitoterapia75117122CrossRefPubMedGoogle Scholar
  24. Da Silva, BP, Bernardo, RR, Parente, JP 1999A furostanol glycoside from rhizomes of Costus spicatusPhytochemistry51931935PubMedGoogle Scholar
  25. De Combarieu, E., Fuzzati, N, Lovati, M, Mercalli, E 2003Furostanol saponins from Tribulus terrestrisFitoterapia74583591CrossRefPubMedGoogle Scholar
  26. Deepak, M, Dipankar, G, Prashanth, D, Asha, MK, Amit, A, Venkataraman, BV 2002Tribulosin and β-sitosterol-d-glucoside, the anthelmintic principles of Tribulus terrestrisPhytomedicine9753756CrossRefPubMedGoogle Scholar
  27. De Kock, WT, Enslin, PR 1958Chemical investigation of photosensitization diseases of domestic animals. I. Isolation and characterization of steroidal sapogenins from Tribulus terrestrisJ. S. African Chem. Inst.113336. Chem Abstr 1958; 52: 17421hGoogle Scholar
  28. Dinchev D & Kostova I (Suppl., 2005) HPLC screening of Tribulus terrestris from different geographical regions for the presence of protodioscin, prototribestin and rutin. Pharmacia LII: 82.Google Scholar
  29. Drewes, ES, George, J, Khan, F 2003Recent findings on natural products with erectile-dysfunction activityPhytochemistry6210191025CrossRefPubMedGoogle Scholar
  30. Eddy, CR, Monroe, EW, Scott, MK 1953Catalog of infrared absorption spectra of steroidal sapogenin acetatesAnal. Chem.25266271CrossRefGoogle Scholar
  31. Fang, S, Hao, C, Sun, W, Liu, Z, Liu, S 1998Rapid analysis of steroidal saponin mixture using electrospray ionization mass spectrometry combined with sequential tandem mass spectrometryRapid Commun. Mass Spectrom.12589594CrossRefPubMedGoogle Scholar
  32. Fang, S, Hao, C, Liu, Z, Song, F, Liu, S 1999Application of electrospray ionization mass spectrometry combined with sequential tandem mass spectrometry techniques for the profiling of steroidal saponin mixture extracted from Tribulus terrestrisPlanta Med.656873CrossRefGoogle Scholar
  33. Frohne, D 1999Ein neues Dopingmittel?Dtsch. Apoth. Ztg.13947524754Google Scholar
  34. Ganzera, M, Bedir, E, Khan, IA 2001Determination of steroidal saponins in Tribulus terrestris by reversed-phase high-performance liquid chromatography and evaporative light scattering detectionJ. Pharm. Sci.9017521758CrossRefPubMedGoogle Scholar
  35. Gauthaman, K, Adaikan, PG, Prasad, RNV 2002Aphrodisiac properties of Tribulus terrestris extract (protodioscin) in normal and castrated ratsLife Sci.7113851396CrossRefPubMedGoogle Scholar
  36. Gheorghiu, A, Ionescu-Matiu, E 1968aPresence of chlorogenin next to diosgenin and gitogenin in Tribulus terrestrisAnn. Pharm. Fr.26745798Chem Abstr 1969; 71: 36365cGoogle Scholar
  37. Gheorgiu, A, Ionescu-Matiu, E 1968bSteroid saponins. Presence of chlorogenin in Tribulus terrestrisStud. Cerect. Biochem.11269273 Chem Abstr 1969; 70: 35069bGoogle Scholar
  38. Gyulemetova R, Tomova M, Simova M, Pangarova T & Peeva S (1982) Determination of furostanol saponins in the preparation Tribestan®. Pharmazie 37, H.4: 296.Google Scholar
  39. Hu, K, Dong, A, Yao, X, Kobayashi, H, Iwasaki, S 1996Antineoplastic agents: I. Three spirostanol glycosides from rhizomes of Dioscorea collettii var. hypoglaucaPlanta Med.62573575PubMedGoogle Scholar
  40. Hu, K, Yao, X 2002Protodioscin (NSC-698 796): its spectrum of cytotoxicity against sixty human cancer cell lines in an anticancer drug screen panelPlanta Med.68297301PubMedGoogle Scholar
  41. Hu, K, Yao, X 2003The cytotoxicity of methyl protodioscin against human cancer cell lines in vitroCancer Invest.21389393CrossRefPubMedGoogle Scholar
  42. Huang, JW, Jiang, SH, Tan, CH, Zhu, DY 2002Structural elucidation of three new steroid sapogeninsYouji Huaxue22917921Chem Abstr 2003; 138: 268359jGoogle Scholar
  43. Huang, JW, Tan, CH, Jiang, SH, Zhu, DY 2003aTerrestrinins A and B, two new steroid saponins from Tribulus terrestrisJ. Assian Nat. Prod. Res.5285290Google Scholar
  44. Huang, JW, Jiang, SH, Tan, CH, Zhu, DY 2003bSapogenins from Tribulus terrestrisNat. Prod. Res. Develop.15101103Google Scholar
  45. Iskenderov, GB 1970Steroidal sapogenins from Tribulus terrestrisKhim. Prir. Soedin.6488489Google Scholar
  46. Kawasaki, T, Komori, T, Miyahara, K, Nohara, T, Hosokawa, I, Mihashi, K 1974Furostanol bisgglycosides coresponding to dioscin and gracillinChem. Pharm. Bull.2221642175Google Scholar
  47. Kianbakht, S, Jahaniani, F 2003Evaluation of Antibacterial Activity of Tribulus terrestris L. Growing in IranIranian J. Pharmacol. Therapeutics22224Google Scholar
  48. Kintya, PK, Perepelitsa, ED, Chirva, VY, Kretsu, LG 1972Steroid saponins. II. Glycosides of Tribulus terrestrisKhim. Prir. Soedin.8475477Google Scholar
  49. Kostova, I, Dinchev, D, Rentsch, GH, Dimitrov, V, Ivanova, A 2002Two new sulfated furostanol saponins fromTribulus terrestrisZ. Naturforsch.57c3338Google Scholar
  50. Li, JX, Shi, Q, Xiong, QB, Prasain, JK, Tezuka, Y, Hareyama, T, Wang, ZT, Tanaka, K, Namba, T, Kadota, S 1998Tribulasamides A and B, new hepatoprotective lignanamides from fruits of Tribulus terrestris: indication of cytoprotective activity in Murine hepatocyte culturePlanta Med.64628631PubMedGoogle Scholar
  51. Li, M, Qu, W, Wang, Y, Wan, H, Tian, C 2002Hypoglycemic effect of saponin from Tribulus terrestrisZhong Yao Cai.25420422PubMedGoogle Scholar
  52. Lin, ZX, Hoult, JR, Raman, A 1999Sulphorhodamine B assay for measuring proliferation of a pigmented melanocyte cell line and its application to the evaluation of crude drugs used in the treatment of vitiligoJ. Ethnopharmacol.66141150CrossRefPubMedGoogle Scholar
  53. Liu, SY, Cui, M, Liu, ZQ, Song, F, Mo, WJ 2004Structural analysis of saponins from medicinal herbs using electrospray ionisation tandem mass spectrometryJ. Am. Soc. Mass. Spectrom.15133141CrossRefPubMedGoogle Scholar
  54. Mahato, SB, Sahu, NP, Ganguiy, AN, Miyahara, K, Kawasaki, T 1981Steroidal glycosides of Tribulus terrestris LinnJ. Chem. Soc. Perkin I924052410Google Scholar
  55. Mahato, SB, Ganguly, AN, Sahu, NP 1982Steroid saponinsPhytochemistry21959978CrossRefGoogle Scholar
  56. Mangle, MS, Jolly, CI 1998HPTLC studies on Tribulus terrestris L. (Chota Gokru) and Pedalium murex L. (Bada Gokhru)Indian Drugs35189194 Chem Abstr 1998; 129: 92380gGoogle Scholar
  57. Matschenko, HE, Gulemetova, R, Kintya, PK, Shashkov, AS 1990A sulfated glycoside from the preparation “Tribestan”Khim. Prir. Soedin5649652Google Scholar
  58. Milanov S, Maleeva E & Tashkov M (1981) Tribestan effect on the concentration of some hormones in the serum of healthy subjects. (Pharmachim, Bulgaria - Company documentation).Google Scholar
  59. Miles, CO, Willkins, AL, Munday, SC, Flaønen, A, Holland, PT, Smith, BL 1993Identification of insoluble salts of the β-d-glucuronides of episarsasapogenin and epismilagenin in the bile of lambs with alved and examination of Nartecium ossifragum, Tribulus terrestris, and Panicum miliaceum for sapogeninsJ. Agric. Food Chem.41914917CrossRefGoogle Scholar
  60. Mimaki, Y, Takaashi, Y, Kuroda, M, Sashida, Y 1997Steroidal glucosides from leaves of Cordyline strictaPhytochemistry4512291234CrossRefGoogle Scholar
  61. Morrison, SM, Scott, JK 1996aVariations in populations of Tribulus terrestris (Zygophyllaceae). 2. Chromosome numbersAust. J. Bot.44191199Google Scholar
  62. Morrison, SM, Scott, JK 1996bVariations in populations of Tribulus terrestris (Zygophyllaceae) 3 Isozyme analysisAust. J. Bot.44201212Google Scholar
  63. Mulinacci, N, Vignolini, P, Marca, G, Pieraccani, G, Innocenti, M, Vincieri, FF 2003Food supplements of Tribulus terrestris L.: an HPLC-ESI-MS method for an estimation of the saponin contentChromatographia57581592Google Scholar
  64. Obreshkova, D, Pangarova, T, Mitkov, S, Dinchev, D 1998Comparative analytical investigation of Tribulus terrestris preparationFarmatsiya (Sofia)451012Google Scholar
  65. Perepelitsa, ED, Kintya, PK 1975Chemical investigation of steroid glycosides from Tribulus terrestris. IV. Steroid saponinsKhim. Prir. Soedin.2260261Google Scholar
  66. Protich M, Tsvetkov D, Nalbanski B, Stanislavov R &␣Katsarova M (1981) Clinical trial of Tribestan on infertilemales. (Pharmachim, Bulgaria - Scientific-technical report).Google Scholar
  67. Recio, MC, Rios, JL, Villar, A 1989Antimicrobial activity of selected plants employed in the spanish mediterranean area. Part IIPhytother. Res.37780Google Scholar
  68. Ren, YJ, Chen, HS, Yang, GJ, Zhu, H 1994Isolation and identification of a new derivative of cinnamic amide from Tribulus terrestrisActa Pharm. Sin.29204206Google Scholar
  69. Rothman, ES, Wall, ME, Eddy, CR 1952Steroidal sapogenins III. Structure of steroidal saponinsJ. Am. Chem. Soc.7440134016Google Scholar
  70. Saleh, NAM, Ahmed, AA, Abdalla, MF 1982Flavonoid Glycosides of Tribulus pentandrus and Tribulus terrestrisPhytochemistry2119952000CrossRefGoogle Scholar
  71. Sang, S, Lao, A, Wang, H, Chen, Z 1999Two new spirostanol saponins from Allium tuberosumJ. Nat. Prod6210281029CrossRefPubMedGoogle Scholar
  72. Scott, JK, Morrison, SM 1996Variarion in populations of Tribulus terrestris (Zygophyllaceae) I Burr morphologyAust. J. Bot.44175190Google Scholar
  73. Shao, Y, Poobrasert, O, Kennelly, EJ, Chin, CK, Ho, CT, Huang, MT, Garrison, SA, Cordell, GA 1997Steroidal saponins from Asparagus officinalis and their cytotoxic activityPlanta Med.63258262PubMedGoogle Scholar
  74. Sharma, HC, Narula, JL 1977Chemical investigation of flowers of Tribulus terrestrisChem. Era131517Chem Abstr 1978; 88: 19055kGoogle Scholar
  75. Stoyanov, N 1973Our Medicinal PlantsNauka & IzkustvoSofia454455Google Scholar
  76. Sun, B, Qu, W, Bai, Z 2003The inhibitory effect of saponins from Tribulus terrestris on Bcap-37 breast cancer line in␣vitroZhong Yao Cai26104106PubMedGoogle Scholar
  77. Sun, WJ, Gao, J, Tu, GZ, Guo, ZW, Zhang, YM 2002A new steroidal saponin from Tribulus terrestris LinnNat. Prod. Lett.16243247PubMedGoogle Scholar
  78. Tomova, M 1980The furostanol saponinsFarmatsya (Sofia)301620Google Scholar
  79. Tomova, M, Panova, D 1965Steroid sapogenins. Isolation of diosgenin from Tribulus terrestris LFarmatsiya (Sofia)15211214Google Scholar
  80. Tomova M, Panova D, Zarkova S & Dikova V (1966) Bulg. Patent (11) 11450, 30 1/02 A61K/1966.Google Scholar
  81. Tomova, M, Panova, D, Wulfson, NS 1974Steroid saponins and sapogenins IV. Saponins from Tribulus terrestrisPlanta Med.25231237Google Scholar
  82. Tomova, MP, Bocheva, DM, Zaikin, WG, Wulfson, NS 1977Steroid saponins and sapogenins V. Hecogenin from Tribulus terrestris LPlanta Med.32223224Google Scholar
  83. Tomova, MP, Gyulemetova, R 1978aSteroidsaponins and steroidsapogenins. VI. Furostanol bisglycoside from Tribulus terrestris LPlanta Med.34188191Google Scholar
  84. Tomova M & Gyulemetova R (1978b) Bulg. Patent (11) 26221, 2(51) A 1K 35/1978.Google Scholar
  85. Tomova M, Gyulemetova R & Zarkova S (1978) An agent for stimulation of sexual function. Bulg. Patent (11) 27584 A61K35/1978.Google Scholar
  86. Tomova M, Gyulemetova R, Zarkova S, Peeva S, Pangarova T & Simova M (1981) Steroidal saponins from Tribulus terrestris L. with a stimulating action on the sexual functions. First Intern. Conf. Chem. Biotechnol. Biol. Active Nat. Prod., Proceedings, Varna, September 3: 289–291.Google Scholar
  87. Tosun, F, Tanker, M, Coskun, M, Tosun, A 1991Determination of diosgenin in Tribulus terrestris L. growing in Turkey by HPLCPharmacia (Ankara)319096. Chem Abstr 1992; 116:231877wGoogle Scholar
  88. Tutin, TG 1968Rosaceae to UmbelliferaeTutin, TGHeywood, VHBurges, NAMoore, DMValentine, DHWalters, SMWebb, DA eds. Flora EuropaeaCambridge at the University pressCambridge205Vol. 2Google Scholar
  89. Viktorov I, Kaloyanov D, Lilov AI, Zlatanova L & Kasabov V (1982) Clinical investigation on Tribestan in males with disorders in the sexual function. Med. Biol. Inform. (Pharmachim, Bulgaria – Company documentation).Google Scholar
  90. Wall, ME, Eddy, CR, McClennan, ML, Klumpp, ME 1952Detection and estimation of steroidal sapogenins in plant tissueAnal. Chem.2413371341CrossRefGoogle Scholar
  91. Wang, B, Ma, L, Lui, T 1990406 cases of angina pectoris in coronary heart disease treated with saponin of Tribulus terrestrisZhong Xi Yi Jie He Za Zhi108587PubMedGoogle Scholar
  92. Wang, Y, Othani, K, Kasai, R, Yamasaki, K 1996Steroidal saponins from fruits of Tribulus terrestrisPhytochemistry4214171422Google Scholar
  93. Wang, Y, Ohtani, K, Kasai, R, Yamasaki, K 1997Steroidal saponins from fruits of Tribulus terrestrisPhytochemistry45811817Google Scholar
  94. Wilkins, AL, Miles, CO, De Kock, WT, Erasmus, GL, Basson, AT, Kellerman, TS 1996Photosensitivity in South Africa. IX. Structure elucidation of a beta-glucosidase-treated saponin from Tribulus terrestris, and the identification of saponin chemotypes of South African T. terrestrisOnderstepoort J.␣Vet. Res.63327334PubMedGoogle Scholar
  95. Wu, G, Jiang, S, Jiang, F, Zhu, D, Wu, H, Jiang, S 1996Steroidal glycosides from Tribulus terrestrisPhytochemistry4216771681PubMedGoogle Scholar
  96. Wu, TS, Shi, LS, Kuo, SC 1999Alkaloids and other constituents from Tribulus terrestrisPhytochemistry5014111415Google Scholar
  97. Xu, Y, Xie, S, Zhao, H, Han, D, Xu, T, Xu, D 2001Studies of the chemical constituents from Tribulus terrestrisYaoxue Xuebao36750753Google Scholar
  98. Xu, YX, Chen, HS, Liu, WY, Gu, ZB, Liang, HQ 1998Two sapogenins from Tribulus terrestrisPhytochemistry49199201Google Scholar
  99. Xu, YX, Chen, HS, Liang, HQ, Gu, ZB, Liu, WY, Leung, WN, Li, TJ 2000Three new saponins from Tribulus terrestrisPlanta Med.66545550CrossRefPubMedGoogle Scholar
  100. Zafar, R, Lawani, M, Siddiqui, AA 1989Hecogenin and neohecogenin from the root of Tribulus terrestrisIndian Drugs26460. Chem Abstr 1989; 111: 121002wGoogle Scholar
  101. Zafar, R, Aeri, V 1992Constituents of Tribulus terrestris flowersFitoterapia6390Google Scholar

Copyright information

© Springer 2005

Authors and Affiliations

  1. 1.Institute of Organic Chemistry with Center of PhytochemistryBulgarian Academy of SciencesSofiaBulgaria

Personalised recommendations