Determination of Structure and Cytotoxicity of Ten Undescribed Steroidal Glycosides from Allium cristophii x A. macleanii 'Globemaster'

被引:1
作者
Shimazaki, Tamami [1 ]
Iguchi, Tomoki [1 ]
Takahashi, Yuna [1 ]
Yamamoto, Kie [1 ]
Takahashi, Naoki [1 ]
Mimaki, Yoshihiro [1 ]
机构
[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Dept Med Pharmacognosy, 1432-1 Horinouchi, Hachioji, Tokyo 1920392, Japan
基金
日本学术振兴会;
关键词
'Globemaster'; Allium cristophii; Allium macleanii; steroidal glycoside; bulb; HL-60; cell; A549; SBC-3; cytotoxicity; INHIBITORY-ACTIVITY; SAPONINS; BULBS; PHOSPHODIESTERASE; METABOLISM; GIGANTEUM;
D O I
10.3390/molecules28176248
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
'Globemaster' is an ornamental hybrid cultivar whose parent plants are Allium cristophii and A. macleanii. The chemical constituents of 'Globemaster' bulbs have not yet been examined; thus, a systematic phytochemical investigation was undertaken herein. A series of chromatographic separations of the MeOH extract of 'Globemaster' bulbs afforded 27 steroidal glycosides (1-27), which are classified into 23 spirostanol glycosides (1-8 and 11-25), two furostanol glycosides (9 and 26), a pregnane glycoside (10), and a cholestane glycoside (27). The structures of the hitherto undescribed compounds (1-10) were determined from the two-dimensional NMR spectroscopic data and hydrolysis. The cytotoxicity of the isolated compounds (1-27) toward HL-60 human promyelocytic leukemia cells, A549 human adenocarcinoma lung cancer cells, and SBC-3 human small-cell lung cancer cells was evaluated. Compounds 8, 22, 23, 24, and 26 exhibited cytotoxicity toward all cell lines in a dose-dependent manner, with IC50 values in the 1.3-49 mu M range.
引用
收藏
页数:22
相关论文
共 23 条
[1]   Hybrid origin of some ornamentals of Allium subgenus Melanocrommyum verified with GISH and RAPD [J].
Friesen, N ;
Fritsch, R ;
Bachmann, K .
THEORETICAL AND APPLIED GENETICS, 1997, 95 (08) :1229-1238
[2]  
GOROVITS MB, 1973, KHIM PRIRODNYK SOEDI, P747
[3]   STEROIDAL GLYCOSIDES FROM ALLIUM-MACLEANII AND A-SENESCENS, AND THEIR INHIBITORY ACTIVITY ON TUMOR PROMOTER-INDUCED PHOSPHOLIPID-METABOLISM OF HELA-CELLS [J].
INOUE, T ;
MIMAKI, Y ;
SASHIDA, Y ;
NISHINO, A ;
SATOMI, Y ;
NISHINO, H .
PHYTOCHEMISTRY, 1995, 40 (02) :521-525
[4]  
Janeczko Z, 2000, Acta Pol Pharm, V57, P131
[5]   STEROIDAL SAPONINS FROM THE BULBS OF ALLIUM-SCHUBERTII [J].
KAWASHIMA, K ;
MIMAKI, Y ;
SASHIDA, Y .
PHYTOCHEMISTRY, 1993, 32 (05) :1267-1272
[6]   STEROIDAL SAPONINS FROM ALLIUM-GIGANTEUM AND ALLIUM-AFLATUNENSE [J].
KAWASHIMA, K ;
MIMAKI, Y ;
SASHIDA, Y .
PHYTOCHEMISTRY, 1991, 30 (09) :3063-3067
[7]  
KAWASHIMA K, 1991, CHEM PHARM BULL, V39, P2761, DOI 10.1248/cpb.39.2761
[8]   STEROIDAL SAPONINS FROM ALLIUM CHINENSE AND THEIR INHIBITORY ACTIVITIES ON CYCLIC-AMP PHOSPHODIESTERASE AND NA+/K+ ATPASE [J].
KURODA, M ;
MIMAKI, Y ;
KAMEYAMA, A ;
SASHIDA, Y ;
NIKAIDO, T .
PHYTOCHEMISTRY, 1995, 40 (04) :1071-1076
[9]   Karataviosides G-K, five new bisdesmosidic steroidal glycosides from the bulbs of Allium karataviense [J].
Kuroda, Minpei ;
Ori, Kazutomo ;
Takayama, Hiroshi ;
Sakagami, Hiroshi ;
Mimaki, Yoshihiro .
STEROIDS, 2015, 93 :96-104
[10]  
MIMAKI Y, 1994, CHEM PHARM BULL, V42, P710, DOI 10.1248/cpb.42.710