STEROIDAL GLYCOSIDES FROM THE BULBS OF LILIUM-DAURICUM

被引:37
作者
MIMAKI, Y [1 ]
ISHIBASHI, N [1 ]
ORI, K [1 ]
SASHIDA, Y [1 ]
机构
[1] TOKYO COLL PHARM,1432-1 HORINOUCHI,HACHIOJI,TOKYO 19203,JAPAN
关键词
LILIUM-DAURICUM; LILIACEAE; BULBS; SPIROSTANOL GLYCOSIDES; TENUIFOLIOL GLYCOSIDE; STEROIDAL GLYCOSIDES;
D O I
10.1016/0031-9422(92)83141-K
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The bulbs of Lilium dauricum yielded 11 compounds, including six new steroidal glycosides. The structures have been determined by spectral analysis and hydrolysis to be (25R,26R)-26-methoxyspirost-5-en-3-beta-ol 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-O-[alpha-L-arabinopyranosyl-(1 --> 3)]-beta-D-glucopyranoside, (25R,26R)-26-methoxyspirost-5-en-3-beta-ol 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-O-[beta-D-glucopyranosyl-(1 --> 4)]-beta-D-glucopyranoside, (25R)-spirost-5-en-3-beta-ol (diosgenin) 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-O-[alpha-L-arabinopyranosyl-(1 --> 3)]-beta-D-glucopyranoside, (25R)-3-beta,17-alpha-dihydroxy-5-alpha-spirostan-6-one 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranoside, (25R)-3-beta,17-alpha-dihydroxy-5-alpha-spirostan-6-one 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-O-[alpha-L-arabinopyranosyl-(1 --> 3)]-beta-D-glucopyranoside and (20R,22R)-3-beta,20,22-trihydroxy-5-alpha-cholestan-6-one (tenuifoliol) 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranoside. The absolute configurations of C-20 and C-22 of tenuifoliol were further confirmed by detailed analysis of the NOE difference spectrum of the corresponding isopropylidene derivative. Several known compounds were also isolated and identified.
引用
收藏
页码:1753 / 1758
页数:6
相关论文
共 16 条
[1]   C-13 NMR SPECTRAL INVESTIGATIONS .10. C-13 NMR-SPECTROSCOPY OF STEROIDAL SAPOGENINS AND STEROIDAL SAPONINS [J].
AGRAWAL, PK ;
JAIN, DC ;
GUPTA, RK ;
THAKUR, RS .
PHYTOCHEMISTRY, 1985, 24 (11) :2479-2496
[2]   CATALOG OF INFRARED ABSORPTION SPECTRA OF STEROIDAL SAPOGENIN ACETATES [J].
EDDY, CR ;
WALL, ME ;
SCOTT, MK .
ANALYTICAL CHEMISTRY, 1953, 25 (02) :266-271
[3]  
HAW SG, 1986, LILIES CHINA, P15
[4]  
Jiang Su New Medical College, 1977, DICT TRADITIONAL CHI, V1, P856
[5]   STUDIES IN STEROID METABOLISM .17. THE INFRARED ABSORPTION SPECTRA OF THE STEROID SAPOGENINS [J].
JONES, RN ;
KATZENELLENBOGEN, E ;
DOBRINER, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (01) :158-166
[6]  
MATSUURA H, 1989, CHEM PHARM BULL, V37, P1390, DOI 10.1248/cpb.37.1390
[7]   LIPID AND STEROIDAL CONSTITUENTS OF LILIUM-AURATUM VAR PLATYPHYLLUM AND LILIUM-TENUIFOLIUM [J].
MIMAKI, Y ;
SASHIDA, Y ;
SHIMOMURA, H .
PHYTOCHEMISTRY, 1989, 28 (12) :3453-3458
[8]   STEROIDAL SAPONINS AND ALKALOIDS FROM THE BULBS OF LILIUM-BROWNII-VAR-COLCHESTERI [J].
MIMAKI, Y ;
SASHIDA, Y .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (11) :3055-3059
[9]   STEROIDAL AND PHENOLIC CONSTITUENTS OF LILIUM-SPECIOSUM [J].
MIMAKI, Y ;
SASHIDA, Y .
PHYTOCHEMISTRY, 1991, 30 (03) :937-940
[10]  
SHIMOMURA H, 1989, Shoyakugaku Zasshi, V43, P64