A Phytochemical Review on Tribulus terrestris Linn

Madhavi T.^1*, Soosammajohn², Khambhoja S.³, Bincy Raj⁴ and Amit Kumar¹.

¹Nargund college of Pharmacy, Bangalore-560085

²East Point College of Pharmacy, Bangalore-560049.

³Oxford College of Pharmacy, Bangalore-560072

⁴Dayananda Sagar College of Pharmacy, Bangalore-560078.

ABSTRACT:

Tribulus terrestris (Linn) is an herb distributed through India and popularly known as Gokhru belonging to the family Zygophyllaceae. The entire plant but more particularly the fruits are used in medicine. In china, Tribulus terrestris (Linn) is used in number of conditions affecting the liver and kidney as well as the cardiovascular and immune system. It is known in ayurveda for its anti-urolithiatic, diuretic and aphrodisiac properties. Leaves are diuretic, tonic, increase the menstrual flow, and cure gonorrhea. The fruit is diuretic removes gravel from the urine and stones in the bladder. The root is good stomachic and appetizers. Various steroidal saponins, alkaloids, furostanal glycosides, flavanoids have been reported. Thus extensive works on the phytochemical investigations have been done to show importance of Tribulus terrestris (Linn).

KEYWORDS:

INTRODUCTION:

Tribulus is a genus of ascending or prostrate herb, belonging to the family Zygophyllaceae, distributed in the tropics and warm- temperature regions of the world. Three species which are found in India are Tribulus terrestris, Tribulus cistoides and Tribulus alatus¹. Among the Indian species Tribulus terrestris (Linn), which is a trailing plant common in sandy soil throughout India, has been described to be of great medicinal value. It is reputed drug in ayurvedic system. The plant is commonly known in Hindi: chotagokhru, English: calthrops or puncture vine. Tribulus terrestris (Linn) is distributed throughout India up to 11,000 ft in Kashmir, Ceylon, tropical and subtropical areas, all warm regions of both hemisphere.²

Morphology of leaf:

Tribulus terrestris (Linn) leaf is found to be opposite, abruptly pinnate, one of each pair usually smaller than the other, stipules lanceolate, hairy, leaflets 3-6 pairs, 6-12 mm long, oblong, mucronate, base round oblique, petiolules short, pilose. Leaves are diuretic, tonic, increase the menstrual flow, and cure gonorrhea; a decoction is useful as a gargle for mouth trouble, painful gum and reduces inflammation.

Morphology of flowers:

Flowers are auxiliary, solitary, yellow, hairy, pedicles tilliform. Sepals are lanceolate, acute, and hairy. Petals oblong, obloid, claw short, hairy; stamen 10, inserted on the base of the disk, alternately longer and shorter, the latter with a small gland outside, naked ovary sessile, 5-12 lobed and celled; style short; stigmas 5-12; ovules superposed.

Morphology of fruits:

Fruit globose, consisting of 5 hairy woodycocci, each with 2 spines. Seeds are many in each cocus, with transverse partitions between them. They are acidic with disagreeable taste, diuretic removes gravel from the urine and stones in the bladder. They are regarded as cooling, diuretic, tonic and aphrodisiac. In some countries they are reputed tonic and astringent, used for coughs, scabies, anemia and ophthalmic. The root is good stomachic and appetizers.

Ayurvedic properties:³

Rasa : Madhura

Guna : Guru, Snigdha

Virya : Sheeta

Vipaka : Madhura

Doshaghna : Vatapittashamaka.

Analysis of green leaves gave the following values:

Moisture : 79.09

Protein : 7.22

Ether extract : 0.54

Total ash : 4.63

Calcium : 1.55

Phosphorus : 0.08%

Iron : 9.22

Vitamin c : 41.53 mg/100

Extractives:

In water : Minimum 85.0%

In 50% V/V alcohol : Minimum 75.0%

Saponins : Minimum 40.0%

Total ash : Maximum 8.0%

Loss on drying : Maximum 6.0%

Heavy metals : Maximum 40 ppm

Pesticide residue : Nil

Phytochemical investigations:

Saponins:

80%ethanolic extract of fruits of Tribulus terrestris is subjected to column chromatography on silica gel using chloroform, methanol and acetone sequentially. which leads to isolation of terrestrosin (A-K) along with five known steroidal saponins, desgalactotogonin, F-gitonin, desglucolanatigonin, gitonin and tigogenin-3-o-β-D xylopyranosyl (1-2) - ( β – D – xylopyranosyl (1-3) – β – D - glucopyranosyl (1-4) - (α-L-rhamnopyranosyl(1-2)-β-D-galactopyranoside.⁴

Isolation of eight steroidal saponins from the butanolic extract of Tribulus terrestris. Among that three compounds are new .the structures are elucidated as hecogenin 3-O-β-xylopyranosyl (1→3)- β-glucopyranosyl(1→4)- β-galactopyranoside; hecogenin 3-O-β-glucopyranosyl(1→2)- β-glucopyranosyl(1→4)- β-galactopyranoside; 3-O-{-β-xylopyranosyl(1→2)-[ β-xylopyranosyl(1→3)]- β-glucopyranosyl(1→4)- [α-rhamnopyranosyl(1→2) ]- β-galactopyranosyl}-26-O- β-glucopyranosyl-22 methoxy-(3 β,5 α,25R)-furostan-2,26-diol.⁵

Two new steroidal saponins named terrestrinins Aand B along with six known compounds were isolated from the Chinese medicinal herb Tribulus terrestris and their chemical structures were elucidated as terrestrinins A-26-O- β-D-glucopyranosyl-(25S)-furostan-4(5)20(22)-diene-3-12-dione;terrestrinins B-26-O- β-D-glucopyranosyl-(25S)-5α-furostan-3β,22 α,26 triol-3--O- β-D- xylopyranosyl(1→3)-[ β-D- xylopyranosyl(1→2)] β-D-glucopyranosyl(1→4)- [α-L-rhamnopyranosyl(1→2)] β-D-galactopyranoside.⁶

Isolated new saponins (25R,S)- 5α- spirostane-12-one-3 β-ol-3-O- β- xylopyranosyl(1-2), [β-xylopyranosyl-(1-3)]- β- glucopyranosyl (1-4)-[α-rhamnopyranosyl(1-2)]-β-galactopyranoside; 26-O-β glucopyranosyl-5α-furostane-12-one-3 β,22 α, 26 triol-3-O- β- glucopyranosyl (1-2) β-galactopyranoside; 26-O- β- glucopyranosyl-(25S)- 5α-furostane-12-one-3 β,22 α,26triol-3-O-β- glucopyranosyl (1-4)-[α-rhamnopyranosyl (1-2)]-β-D-galactopyranoside.⁷

A new steroidal saponins containing six monosaccharide was obtained from the total plant of Tribulus terrestris and elucidated as 26-O- β-D- glucopyranosyl-22-methoxy-furostane-3-O-β-D-xylopyranosyl-(1-3)-[β-D-xylopyranosyl-(1-2)]-β-D-glucopyranosyl(1-4)-[α-L-rhamnopyranosyl(1-2)]-β-D-galactopyranoside.⁸

Isolated two new steroidal sapogenins (5α-25R)-spirostan-3, 6, 2-trione and 25R- spirostan-4-ene-3, 6, 12-trione, along with five steroidal sapogenins, tigogenin, hecogenin, gitogenin, hecogenone and 25R-spirostan-4-ene-3, 12-dione.⁹

Protodioscin, new saponins (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.¹⁰

Protodioscin and methyl Protodioscin along with two new sulfated saponins have been isolated, they are elucidated as ,sodium salt of 26-O-β – glucopyranosyl-22α-methoxy-(25S)-furost-5-ene-3 β,26-diol-3-O-α-rhamnopyranosyl-(1→2)- β-4-O-sulfo-glucopyranoside. (methyprototribestin); 26-O-β – glucopyranosyl-22α-hydroxy--(25S)-furost-5-ene-3 β,26-diol-3-O-α-rhamnopyranosyl-(1→2)- β-4-O-sulfo-glucopyranoside. (prototribestin).¹¹

Flavanoids:

Flavanoids like kaempferol, kaempferol-3-glucoside, kaempferol-3-rutinoside and tribuloside (kaempferol-3-β-D-(6-p-coumaroyl glucoside) have been isolated from Tribulus terrestris.¹²

Alkaloids:

Alkaloids like tribulusterine, terrestribisamide, harmine, harmaline, Harman and tetrahydroharmine in the plant Tribulus terrestris have been confirmed¹³.

Three new compounds, terrestribisamide, 25R-spirostan-4-ene-3, 12-dione and tribulusterine, together with 10 known compounds, N-P-coumaroyltyramine, terrestriamide, hecogenin, aurantiamide acetate, xanthosine, fatty acid ester, ferulic acid, vanillin, p-hydroxybenzoic acid and β-sitosterol were isolated from Tribulus terrestris¹⁴.

β-sitosterol-D-glucoside, dioscin, two new steroidal glycosides, neohecogenin glucoside and tribulosin have been isolated from ethanolic extract of the aerial parts of Tribulus terrestris on chromatography, along with these compounds neohecogenin-3-O-β-D-glucopyranoside, neotigogenin 3-O-β-D-xylopyranosyl-(1-3) [β-D- xylopyranosyl-(1-3)]- β-D- glucopyranosyl (1-4)-[α-rhamnopyranosyl(1-2)]-β-D-galactopyranoside was isolated and this was confirmed by NMR and mass spectral data’s.¹⁵

Pharmacological investigations:

The antibacterial activity of the plant extract (alcoholic and aqueous extract) against S.aureus and E.coli and reported that the extracts of leaves are effective against both the organisms, whereas the aqueous extract of seeds was only active against S.aureus. But alcoholic as well as aqueous extract of the stem was not showing antibacterial activity.²

Anti-tumor activity:

Anti-tumor activity of the crude drug extract of Tribulus terrestris Linn has been reported. The preliminary examination of the anti-tumor screening was done with sarcoma 180 as cites mice.²

The aqueous fraction induced mild hypotension, showed anti acetylcholine like action on the rat intestine and also synergized this action on the frog rectus. Its diuretic effect was found to be very insignificant.¹⁶

The anthelmentic activity of tribulosin and β-sitosterol-D-glucoside on caenorhaditis elegan.¹⁷

The antihypertensive and vasodilator effects on methanolic and aqueous extracts of Tribulus terrestris in rats.¹⁸

The antifungal activities and action mechanisms of compounds from Tribulus terrestris saponins are known to be antifungal and antibacterial.¹⁹

Tribulus terrestris have been used as an aphrodisiac both in India and Chinese traditional system of medicine. Administration of Tribulus terrestris extract increased sexual behavior and pressure both in normal and rats and effects were probably due to the androgen increasing property of Tribulus terrestris.²⁰

In this investigations chemical and biological studies if Tribulus terrestris Linn have been carried out. the chemical analysis revealed the presence of steroidal saponins, flavanoids, furostanol saponins, alkaloids etc; the pharmacological studies revealed that the Tribulus terrestris Linn have been tested for diuretic, anthelmentic, antifungal, antimicrobial, antitumor ,antihypertensive and vasodilator effects and aphrodisiac activity.

REFERENCES:

1. S K Gupta, R Zafar, and D Pathak. Review of phytochemical and pharmacological aspects of Steroidal saponins from Tribulus terrestris. Indian drugs 1997; 34(8):422-26.

2. Zafar R and Mukesh Lalwani.T. Tribulus terrestris Linn- A review of the current knowledge. Indian drugs.1989; 27(3):148-153.

3. Nandan Kumar Jha, Dr I K Pandey, Anup Kumar Jha. Tribulus terrestris. Phytopharm 2006:3-10.

4. Wang Yan, Kazuhiro Ohtani, Ryoji Kasai and Kazuo Yamasaki. Steroidal saponins from fruits of Tribulus terrestris. Photochemistry 1996; 42(5):1417-22.

5. Xu Yx, Chen H S, Liang H Q, Gu Z B ,Liu W Y, Leung W N, Li T J. Three new saponins from Tribulus terrestris. Planta Med 2000; 66(6):545-50.

6. Huang J W, Tan C H, Jiang S H, Zhu DY. Terrestrinins A and B, two new steroidal saponins from Tribulus terrestris. J Asian Nat Prod. Res 2003; 5(4):285-90.

7. Lifeng Cai, Yijie Wu, Jianguo Zhang, Fengkui Pei, Yajuan Xu, Sheng Xu Xie, Dongming Xu. Steroidal saponins from Tribulus terrestris. Planta Med 2001; 67:196-98.

8. Sun W, Gao J, Tu G, Guo Z, Zhang Y.A new steroidal saponins from Tribulus terrestris. Nat. Prod. Lett 2002; 16(4):243-47.

9. Yi-Xin Xu, Hai –Sheng Chen, Wen-Yong Liu, Zheng-Bing gu and Hua-Qing Lang. Two sapogenins Tribulus terrestris. Phytochemistry 1998; 49(1):199-201

10. De Combarieu E, Fuzzati N, Lovati M, Mercalli E. Furostanol saponins from Tribulus terrestris. Fitoterapia 2003; 74(6):583-91.

11. Kostova I, Dinchev D, Rentsch G H, Dimitrov V, Ivanova A. Two sulfated furostanol saponins from Tribulus terrestris. J. Naturforsch 2002; 57(1-2):33-

12. S P Bhutani, S Chibber and T R Seshadri. Flavanoids of the fruits and leaves of Tribulus terrestris. Phytochemistry 1969; 8:299-303.

13. S K Gupta, R Zafar and D Pathak. Review of phytochemical and pharmacological aspects of Steroidal saponins from Tribulus terrestris. Indian drugs 1997; 34(8):422-26.

14. Tian-Shung Wu, Li- Shian Shi, Shang-Chu-Kuo. Alkaloids and other constituents from Tribulus terrestris. Phytochemistry 1999; 50:1411-15.

15. Shashi B Mahato, Niranjan P Sahu and Amar N Ganguly. Steroidal glycosides of Tribulus terrestris. 1981:2405-10.

16. B C Bose, A Q Saifi, R Vijayvargiya and J N Bhatnagar. Some aspects of chemical and pharmacological studies of Tribulus terrestris. Indian of Med Sci 1963; 17(4):291-93.

17. M Deepak, G Dipankar, D Prashanth, M K Asha, A Amit and B V Venkataraman .Tribulosin and β-Sitosterol-D-Glucoside, anthelmentic principles of Tribulus terrestris. Phytomedicine 2002; 9:753-56.

18. The Oludotun A Phillips, Koyippalli T Mathew, Mabayoje A Oriowo. Antihypertensive and vasodilator effects of Tribulus terrestris. J of Ethno Pharmacology 2006; 104:351-55.

19. Ju Dong Zhang, Zheng Xu, Yong-Bing Cao, Hai-Sheng Chen, Lan Yan. Antifungal activities of Tribulus terrestris. J of Ethno Pharmacology 2006; 103:76-84.

20. K Gauthaman, P G Adaikan. Effect of Tribulus terrestris on nicotinamide adenine dinucleotide phosphate –diaphorase activity and androgen receptors in rat brain. J of Ethno Pharmacology 2005; 96:127-132.

Received on 28.05.2011

Accepted on 29.06.2011

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Research J. Pharmacology and Pharmacodynamics. 3(5): Sept –Oct. 2011, 218-222