Steroidal Saponins In Tribulus Terrestris Fruit

Tribulus terrestris L.is an annual creeping herb growing on roadsides and hills in China. In traditional Chinese medicine,the fruit of T.terrestris,which is known as 'Ci Ji Li',have long been used for the treatment of eye trouble,edema and abdominal distention,emission and morbid leucorrhea as well as vitiligo.In India,it has long been used as medicine against impotency and cardiovascular disease.The current treatment for impotency,"Tribestane"and "Vitanone",as well as treatment for cardiovascular disease."Tribusaponins" and "Xin-nao-shu-tong",are all made of crude saponins from Tribulus terrestris.From the 75%ethanol extract of the fruits of T.terrestris,17 compounds were isolated by means of solvent partition,repeated column chromatography on silica gel,MPLC,HPLC. On basis of physico-chemical properties and spectroscopic analysis,their structures were identified as follows.Steroidal glycosides:(23S,25S)-5α-spirostan-24-one-3β,23-dihydroxy-3-O-{O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside }(1),(24S,25S)-5α-spirostan-3β,24-diol-3-O-{O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-gluco pyranosyl-(1→4)]-β-D-galactopyranoside}(2),hecogenin 3-O-{O-α-L-rhamnopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside}(3),hecogenin3-O-{O-β-D-glucop yranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopy ranoside}(4),(25R)-5α-spirostan-12-one-2α,3β-dihydroxy(manogenin)3-O-{O-β-D-gluco pyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactop yranoside}(5),26-O-β-D-glucopyranosyl-(25R)-5α-furostan-12-one-3β,22a,26-triol-3-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside(6), 26-O-β-D-glucopyranosyl-(25S)- 5α-furosta n-12-one-3β,22a,26-triol-3-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside(7),26-O -β-D-glucopyranosyl-25(R)-5α-furostan- 12-one-3β,22 a,26-triol-3 -O- {O-α-L-rhamnopyranos yl-(1→2)-O-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside}(8),26-O-β-D-glucopyran osyl-25(S)-5α-furostan-2α,3β,22α,26-tetraol-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyran osyl-(1→4)-β-D-galactopyranoside(9),26-O-β-D-glucopyranosyl-25(R)-5α-furostan-2α,3β, 22α,26-tetraol-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-β-D-galactopyran oside(10),26-O-β-D-glucopyranosyl-(25R)-5α-furostan-20(22)-en-2α,3β,26-triol-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside(11), 26-O-β-D- glucopyranosyl-25(S)-5α-furostan-12-one-22-methoxy-3β,26-diol-3-O-{O-α-L-rhamnopyran osyl-(1→2)-O-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside}(12),26-O-β-D-glucopy ranosyl-(25R)-furostan-12-one-3β,22α,26-tril-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopy ranosyl-(1→4)-β-D-galactopyranoside(13),26-O-β-D-glucopyranosyl-(25R)-5α-furostan-20 (22)-en-12-one-3β,26-diol-3-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside(14),26 -O-β-D-glucopyranosyl-25(S)-5α-furostan- 12-one-3β,22α,26-triol-3-O-{O-α-L-rhamnopyran osyl-(1→2)-O-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside}(15).Flavonoid glycosi des:kaempferol-3-O-diglucopyranoside(16),isorhamnetin-3-O-diglucopyranoside(17). Among them,compounds 1-3,6-13 were new compounds;compound 5 was firstly isolated from this genus.