Cytotoxic epimeric ginsenosides from the flower buds of Panax ginseng

[Display omitted] •Previously undescribed ginsenoside epimers were isolated from flower buds of Panax ginseng.•Their stereoconfiguration were assigned based on spectroscopic analyses and reported data.•Different configuration had a significant impact on the antitumor activity.•Compounds with S-confi...

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Bibliographic Details
Published in:Steroids 2019-03, Vol.143, p.1-5
Main Authors: Li, Ke-Ke, Xu, Fei, Li, Sha-Sha, Cao, Gui-Yun, Gong, Xiao-Jie
Format: Article
Language:English
Subjects:
(R)- or (S)-stereoisomers
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Cell Line, Tumor
Cytotoxic activity
Flowers - chemistry
Ginsenosides
Ginsenosides - chemistry
Ginsenosides - pharmacology
Humans
Hydrolysis
Panax - chemistry
Panax ginseng
Stereoisomerism
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Summary:[Display omitted] •Previously undescribed ginsenoside epimers were isolated from flower buds of Panax ginseng.•Their stereoconfiguration were assigned based on spectroscopic analyses and reported data.•Different configuration had a significant impact on the antitumor activity.•Compounds with S-configuration displayed potential higher antitumor activity. Three pairs of ginsenoside epimers, including three new compounds (2, 3 and 5), were isolated from the flower buds of Panax ginseng. The structures of the isolated compounds were elucidated on the basis of considerable spectroscopic analyses and comparison with the reported data. All six compounds were evaluated for their cytotoxicties against three human cancer cell lines, HL-60, MGC80-3 and Hep-G2. Compounds 1, 3, and 6 with S configurations at C-24 or C-20 showed moderate inhibitory activities with IC50 values of 25.32, 18.76, and 38.64 μM in HL-60 cells, respectively. Our findings showed that different configurations of these isolated ginsenosides had a significant impact on the antitumor activity, and S epimers were higher than R.
ISSN:0039-128X
1878-5867
DOI:10.1016/j.steroids.2018.12.002