New chlorogenin hexasaccharide isolated from Agave fourcroydes with cytotoxic and cell cycle inhibitory activities

被引:45
作者
Ohtsuki, T
Koyano, T
Kowithayakorn, T
Sakai, S
Kawahara, N
Goda, Y
Yamaguchi, N
Ishibashi, M
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
[2] Temko Corp, Nakano Ku, Tokyo 1640012, Japan
[3] Khon Kaen Univ, Fac Agr, Dept Hort, Khon Kaen 40002, Thailand
[4] Natl Inst Hlth Sci, Div Pharmacognosy Phytochem & Narcot, Setagaya Ku, Tokyo 1588501, Japan
关键词
Agavaceae; Agave fourcroydes; steroidal saponin; cytotoxicity; cell cycle;
D O I
10.1016/j.bmc.2004.05.004
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
A new chlorogenin hexasaccharide (1) was isolated from leaves of Agave fourcroydes (Agavaceae). The structure of the new saponin was elucidated as chlorogenin 3-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)-{beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->2)}-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside] (1) by spectroscopic analysis and the result of acidic hydrolysis. The new saponin (1) as well as known hexasaccharides (3 and 5) isolated here showed cytotoxicity against HeLa cells, and I exhibited a cell cycle inhibitory effect at the G2/M stage at the concentration of 7.5 and 10 mug/mL. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3841 / 3845
页数:5
相关论文
共 18 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]  
BOCK K, 1973, TETRAHEDRON LETT, P1037
[3]   Asexual genetic variability in Agave fourcroydes [J].
Infante, D ;
González, G ;
Peraza-Echeverría, L ;
Keb-Llanes, M .
PLANT SCIENCE, 2003, 164 (02) :223-230
[4]  
Itabashi M, 2000, CARBOHYD RES, V323, P57
[5]   Spirostanol and furostanol glycosides from the fresh tubers of Polianthes tuberosa [J].
Jin, JM ;
Zhang, YJ ;
Yang, CR .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (01) :5-9
[6]  
Kawamoto S, 2003, CHEM PHARM BULL, V51, P737, DOI 10.1248/cpb.51.737
[7]   Steroidal glycosides from the bulbs of Camassia leichtlinii and their cytotoxic activities [J].
Kuroda, M ;
Mimaki, Y ;
Hasegawa, F ;
Yokosuka, A ;
Sashida, Y ;
Sakagami, H .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (06) :726-731
[8]   LABORATORY DETERMINATION OF CHEMOTHERAPEUTIC DRUG-RESISTANCE IN TUMOR-CELLS FROM PATIENTS WITH LEUKEMIA, USING A FLUOROMETRIC MICROCULTURE CYTOTOXICITY ASSAY (FMCA) [J].
LARSSON, R ;
KRISTENSEN, J ;
SANDBERG, C ;
NYGREN, P .
INTERNATIONAL JOURNAL OF CANCER, 1992, 50 (02) :177-185
[9]  
MIMAKI Y, 1992, CHEM PHARM BULL, V40, P148
[10]   STEROIDAL SAPONINS FROM THE BULBS OF CAMASSIA-CUSICKII [J].
MIMAKI, Y ;
SASHIDA, Y ;
KAWASHIMA, K .
PHYTOCHEMISTRY, 1991, 30 (11) :3721-3727