Cholestane rhamnosides from the bulbs of Ornithogalum saundersiae

被引：14
作者：
Kuroda, M [1 ]
Mimaki, Y [1 ]
Sashida, Y [1 ]
机构：
[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan
来源：
PHYTOCHEMISTRY | 1999年 / 52卷 / 03期
关键词：
Ornithogalum saundersiae; Liliaceae; bulbs; cholestane rhamnosides; cytostatic activity; HL-60; cells;
D O I：
10.1016/S0031-9422(99)00240-X
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：
Phytochemical examination of the bulbs of Ornithogalum saundersiae yielded six cholestane rhamnosides, two of which had previously been isolated from the same plant material. However, detailed spectroscopic analysis of the aglycone led us to revise the configuration of the C-ll hydroxyl group of the latter two and reassign their structures as; (22S)cholest-5-ene-3 beta,11 alpha,16 beta,22-tetrol 16-O-alpha-L-rhamnopyranoside and (22S)-cholesta-5,24-diene-3 beta, 11 alpha,16 beta,22-tetrol 16-Q-alpha-L-rhamnopyranoside, respectively. The other four are new naturally occurring constituents and their structures were determined to be (22S)-cholest-5-ene-3 beta,11 alpha,16 beta,22-tetrol 16-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside), (22S)-cholest-5-enq-3 beta,11 alpha,16 beta,22-tetrol 16-O-{2-O-acetyl-3-O-(3,4,5-trimetboxybenzyol)-alpha-L-rhamnopyanoside}, (22S)-cholest-5-ene-3 beta, 11 alpha,16 beta,22-tetro 16-O-{2-O-acetyl-3-O-(p-methaxybenzoyl)-alpha-L-rhamnopyranoside}, and (22S)-cholesta-5,24-diene-3 beta,11 alpha,16 beta,22-tetrol 16-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranoside), respectively. The isolated compounds were evaluated for their cytostatic activity against leukemia HL-60 cells. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：445 / 452
页数：8
相关论文
共 15 条
[1]   THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION [J].
HAASNOOT, CAG ;
DELEEUW, FAAM ;
ALTONA, C .
TETRAHEDRON, 1980, 36 (19) :2783-2792
[2]  
KUBO S, 1992, CHEM PHARM BULL, V40, P2469, DOI 10.1248/cpb.40.2469
[3]   ACYLATED CHOLESTANE GLYCOSIDES FROM THE BULBS OF ORNITHOGALUM-SAUNDERSIAE [J].
KUBO, S ;
MIMAKI, Y ;
TERAO, M ;
SASHIDA, Y ;
NIKAIDO, T ;
OHMOTO, T .
PHYTOCHEMISTRY, 1992, 31 (11) :3969-3973
[4]  
KURODA M, 1995, CHEM PHARM BULL, V43, P1257, DOI 10.1248/cpb.43.1257
[5]   Novel cholestane glycosides from the bulbs of Ornithogalum saundersiae and their cytostatic activity on leukemia HL-60 and MOLT-4 cells [J].
Kuroda, M ;
Mimaki, Y ;
Sashida, Y ;
Hirano, T ;
Oka, K ;
Dobashi, A ;
Li, HY ;
Harada, N .
TETRAHEDRON, 1997, 53 (34) :11549-11562
[6]   STRUCTURE OF A NOVEL 22-HOMO-23-NORCHOLESTANE TRISACCHARIDE FROM ORNITHOGALUM-SAUNDERSIAE [J].
KURODA, M ;
MIMAKI, Y ;
SASHIDA, Y ;
NIKAIDO, T ;
OHMOTO, T .
TETRAHEDRON LETTERS, 1993, 34 (38) :6073-6076
[7]  
KURODA M, 1999, PHYTOCHEMISTRY
[8]   Three novel rearranged cholestane glycosides from Ornithogalum saundersiae bulbs and their cytostatic activities on leukemia HL-60 and MOLT-4 cells [J].
Mimaki, Y ;
Kuroda, M ;
Sashida, Y ;
Hirano, T ;
Oka, K ;
Dobashi, A ;
Koshino, H ;
Uzawa, J .
TETRAHEDRON LETTERS, 1996, 37 (08) :1245-1248
[9]   A new cytotoxic cholestane bisdesmoside from Ornithogalum saundersiae bulbs [J].
Mimaki, Y ;
Kuroda, M ;
Kameyama, A ;
Sashida, Y ;
Hirano, T ;
Oka, K ;
Koike, K ;
Nikaido, T .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1996, 60 (06) :1049-1050
[10]   A new rearranged cholestane glycoside from Ornithogalum saundersiae bulbs exhibiting potent cytostatic activities on leukemia HL-60 and MOLT-4 cells [J].
Mimaki, Y ;
Kuroda, M ;
Kameyama, A ;
Sashida, Y ;
Hirano, T ;
Oka, K ;
Dobashi, A .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (22) :2635-2638
12