Study On Chemical Constituents Of Ophiopogon Japonicus

Purpose: This is a study on chemical constituents from the tuber of Ophiopogonjaponicus.Method: Macroporous resin, silica gel, ODS, and preparative HPLC chromatographicmethod were used to isolate steroidal saponin from the traditional Chinese medicineOphiopogon japonicus. By mass spectrometry,13C-NMR,1H-NMR, HMBC, HSQC,and1H-1H-COSY spectroscopy techniques, the structure of these compounds wereelucidated.Result:26compounds were isolated from Ophiopogon japonicus. Except for compounds6and22.24compounds were elucidated,18known compounds and6new compounds were determined.18known compounds were identified as:(25R)-spirost-5-en-3β,17α-dihydroxy-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucoyranoside (Chonglouoside VI,1),(25R)-spirost-5-en-3β,14α,17α-trihydroxy-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside (Saponin V,2),(25R)-spirost-5-en-3β,14α-dihydroxy-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside (25R-Dracaenoside F,3),(25R)-spirost-5-en-3β,17α-dihydroxy-3-O-α-L-rhamnopyranosyl-(1â†'2)-[β-D-xylopyranosyl-(1â†'4)]-β-D-glucopyranoside (4),(25R)-spirost-5-en-3β,14α-dihydroxy-3-O-α-L-rhamnopyranosyl-(1â†'2)-[β-D-xylopyranosyl-(1â†'4)]-β-D-glucopyranoside (Saponin U,5),(25R)-spirost-5-en-3β-hydroxy-3-O-α-L-rhamnopyranosyl-(1â†'2)-[β-D-xylopyranosyl-(1â†'4)]-β-D-glucopyranoside (OphiopojaponinC,7), diosgenin-3-O-α-L-rhamnopyranosyl-(1â†'2)-[β-D-xylopyranosyl-(1â†'4)]-β-D-glucopyranoside (Ophiopogonin D′,8),(25R)-26-O-[β-D-glucopyranosyl-(1â†'2)]-β-D-glucopyranosyl-furost-5-en-3β,22α,26-trihydroxy-3-O-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside (Ophiopogonins H,9),(25R)-26-O-[-D-glucopyranosyl-(1â†'2)]-D-glucopyranosyl-furost-5-en-3β,14α,22α,26-tetrahydroxy-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside (11),(25R)-26-O-[β-D-glucopyranosyl-(1â†'2)]-β-D-glucopyranosyl-furost-5,22-dien-3β,20α,26-trihydroxy-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside (Ophiopogonins I,12),(25R)-26-O-[β-D-glucopyranosyl-(1â†'2)]-β-D-glucopyranosyl-furost-5-en-3β,22α,26-trihydroxy-3-O-α-L-rhamnopy ranosyl-(1â†'2)-[β-D-xylopyranosyl-(1â†'4)]-β-D-glucopyranoside (Ophiopogonin F,14),(25R)-26-O-β-D-glucopyranosyl-furost-5-en-3β,22α,26-trihydroxy-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside (Protobioside,16),(20S,25R)-26-O-β-D-glucopyranosyl-furost-5-en-3β,17α,22α,26-tetrahydroxy-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside (19),(25R)-26-O-β-D-glucopyranosyl-cholest-5-en-3β,26-dihydroxy-16,22-dioxo-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside(21),(25R)-26-O-β-D-glucopyranosyl-furost-5-en-3β,22α,26-trihydroxy-3-O-α-L-rhamnopyranosyl-(1â†'2)-[β-D-xylopyranosyl-(1â†'4)]-β-D-glucopyranoside (Pallidifloside I,23),(25R)-26-O-β-D-glucopyranosyl-furost-5-en-3β,14α,22α,26-tetrahydroxy-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside (24),(25R)-26-O-[β-D-glucopyranosyl-(1â†'2)]-β-D-glucopyranosyl-furost-5-en-3β,14α,17α,22α,26-quiqehydroxy-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside (Ophiopogonin K,25),(25R)-spirost-5-en-1β,3β-dihydroxy-1-O-α-L-rhamnopyranosyl-(1â†'2)-[β-D-xylopyranosyl-(1â†'3)]-β-D-fucopyranoside (Ophiopogonin D,26). Six new compounds were identified as:(25R)-26-O-[β-D-glucopyranosyl-(1â†'6)]-β-D-glucopyranosyl-cholest-5,14-dien-3β,26-dihydroxy-16,22-dioxo-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside (10),(25R)-26-O-[β-D-glucopyranosyl-(1â†'6)]-β-D-glucopyranosyl-cholest-5,14,17-trien-3β,26-dihydroxy-16,22-dioxo-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside (13),(25R)-26-O-β-D-glucopyranosyl-furost-5-en-3β,14α,17α,22α,26-pentahydroxy-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside (15),(25R)-26-O-β-D-glucopyranosyl-3β,26-dihydroxy-cholest-5,14-dien-16,22-dioxo-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside (17),(25R)-26-O-β-D-glucopyranosyl-3β,26-dihydroxy-cholest-5,14,17-trien-16,22-dioxo-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside (18),(20R,25R)-26-O-β-D-glucopyranosyl-3β,26-dihydroxy-cholest-5-en-16,22-dioxo-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside (20).