JATROPHAM DERIVATIVES AND STEROIDAL SAPONINS FROM THE BULBS OF LILIUM-HANSONII

被引:43
作者
ORI, K
MIMAKI, Y
MITO, K
SASHIDA, Y
NIKAIDO, T
OHMOTO, T
MASUKO, A
机构
[1] TOKYO COLL PHARM,1432-1 HORINOUCHI,HACHIOJI,TOKYO 19203,JAPAN
[2] NIPPON OIL CO LTD,CENT TECH RES LAB,NAKA KU,YOKOHAMA,KANAGAWA 231,JAPAN
[3] TOHO UNIV,FAC PHARMACEUT SCI,FUNABASHI,CHIBA 274,JAPAN
关键词
LILIUM-HANSONII; LILIACEAE; BULBS; JATROPHAM DERIVATIVES; STEROIDAL SAPONINS; X-RAY ANALYSIS; CYCLIC AMP PHOSPHODIESTERASE; INHIBITORY ACTIVITY;
D O I
10.1016/0031-9422(92)83627-B
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
Two new jatropham derivatives and three new steroidal saponins were isolated from the fresh bulbs of Lilium hansonii, along with previously known compounds. The structures of the new compounds were elucidated, on the basis of spectroscopic data and chemical evidence, and by comparing them with those of known compounds, as (-)-5-hydroxy-3-methyl-3-pyrrolin-2-one (jatropham) 5-O-beta-D-glucopyranosyl-(1 --> 3)-beta-D-glucopyranoside, (2S*,4R*)-1-(3-methyl-2-oxo-3-pyrrolinyl)-4-methyl-5-oxo-2-pyrrolidinecarboxylic acid, 26-O-beta-D-glucopyranosyl-(25R)-5-alpha-furostan-3-beta,22-xi-diol 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-O-[beta-D-glucopyranosyl-(1 --> 4)]-beta-D-glucopyranoside, (25R)-5-alpha-spirostan-3-beta,12-alpha-diol 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-O-[beta-D-glucopyranosyl-(1 --> 4)]-beta-D-glucopyranoside and (25R)-spirost-5-en-3-beta,12-alpha-diol 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-O-[beta-D-glucopyranosyl-(1 --> 4)]-beta-D-glucopyranoside, respectively. The stereostructure of jatropham dimer, the plain structure of which was presented previously, was confirmed by X-ray crystallographic analysis. The inhibitory activity on cyclic AMP phosphodiesterase of the steroidal saponins was evaluated.
引用
收藏
页码:2767 / 2775
页数:9
相关论文
共 17 条
[1]  
ABDULLAEV ND, 1987, KHIM PRIR SOEDIN+, P692
[2]   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
[3]  
Breitmaier E., 1987, CARBON 13 NMR SPECTR, P279
[4]  
BRYAN JE, 1989, BULBS, V2, P251
[5]   CONSTITUENTS OF GRAMINEAE .2. NEW PHENOLIC DIGLYCERIDES FROM AEGILOPS-OVATA [J].
COOPER, R ;
GOTTLIEB, HE ;
LAVIE, D .
PHYTOCHEMISTRY, 1978, 17 (09) :1673-1675
[6]   DIMERIC PYRROLINE ALKALOIDS FROM LILIUM-CANDIUM L [J].
HALADOVA, M ;
EISENREICHOVA, E ;
BUCKOVA, A ;
TOMKO, J ;
UHRIN, D ;
UBIK, K .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1991, 56 (02) :436-438
[7]  
HAW SG, 1986, LILIES CHINA, P37
[8]   EFFECTS OF ALPHA-TICOGENIN AND BETA-TIGOGENIN CELLOBIOSIDES ON CHOLESTEROL ABSORPTION [J].
MALINOW, MR ;
GARDNER, JO ;
NELSON, JT ;
MCLAUGHLIN, P ;
UPSON, B ;
AIGNERHELD, R .
STEROIDS, 1986, 48 (3-4) :197-211
[9]  
NIKAIDO T, 1981, CHEM PHARM BULL, V29, P3586
[10]   INHIBITORS OF CYCLIC-AMP PHOSPHODIESTERASE IN MEDICINAL-PLANTS [J].
NIKAIDO, T ;
OHMOTO, T ;
NOGUCHI, H ;
KINOSHITA, T ;
SAITOH, H ;
SANKAWA, U .
PLANTA MEDICA, 1981, 43 (01) :18-23