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

被引:0
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
来源
MOLECULES | 2023年 / 28卷 / 17期
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
  • [11] Mimaki Y, 1999, CHEM PHARM BULL, V47, P738, DOI 10.1248/cpb.47.738
  • [12] A new furostanol saponin with six sugars from the bulbs of Allium sphaerosephalon structural elucidation by modern NMR techniques
    Mimaki, Y
    Satou, T
    Kuroda, M
    Kameyama, A
    Sashida, Y
    Li, HY
    Harada, N
    [J]. CHEMISTRY LETTERS, 1996, (06) : 431 - 432
  • [13] Steroidal saponins from the underground parts of Chlorophytum comosum and their inhibitory activity on tumour promoter-induced phospholipids metabolism of HeLa cells
    Mimaki, Y
    Kanmoto, T
    Sashida, Y
    Nishino, A
    Satomi, Y
    Nishino, H
    [J]. PHYTOCHEMISTRY, 1996, 41 (05) : 1405 - 1410
  • [14] Steroidal glycosides from the bulbs of Allium jesdianum
    Mimaki, Y
    Kuroda, M
    Fukasawa, T
    Sashida, Y
    [J]. JOURNAL OF NATURAL PRODUCTS, 1999, 62 (01): : 194 - 197
  • [15] STEROIDAL GLYCOSIDES FROM ALLIUM-ALBOPILOSUM AND A-OSTROWSKIANUM
    MIMAKI, Y
    KAWASHIMA, K
    KANMOTO, T
    SASHIDA, Y
    [J]. PHYTOCHEMISTRY, 1993, 34 (03) : 799 - 805
  • [16] Mimaki Yoshihiro, 1999, Natural Medicines, V53, P88
  • [17] Mimaki Yoshihiro, 1996, Natural Medicines, V50, P308
  • [18] Mimaki Yoshihiro, 1999, Natural Medicines, V53, P134
  • [19] MORITA T, 1988, CHEM PHARM BULL, V36, P3480
  • [20] Small-cell lung cancer
    Rudin, Charles M.
    Brambilla, Elisabeth
    Faivre-Finn, Corinne
    Sage, Julien
    [J]. NATURE REVIEWS DISEASE PRIMERS, 2021, 7 (01)