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Molecules. 2018 Feb 2;23(2). pii: E315. doi: 10.3390/molecules23020315.

Nine New Gingerols from the Rhizoma of Zingiber officinale and Their Cytotoxic Activities.

Author information

1
School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, China. lzzdyq1992@163.com.
2
School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, China. wangyz@hactcm.edu.cn.
3
Collaborative Innovation Center for Respiratory Disease Diagnosis, Treatment and New Drug Research and Development of Henan Province, Henan University of Chinese Medicine, Zhengzhou 450046, China. wangyz@hactcm.edu.cn.
4
School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, China. gaoxiaomei6266@126.com.
5
School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, China. qingyixin@163.com.
6
School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, China. 13598851831@139.com.
7
School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, China. yxcheng@szu.edu.cn.
8
Guangdong Key Laboratory for Genome Stability & Disease Prevention, School of Pharmaceutical Sciences, School of Medicine, Shenzhen University Health Science Center, Shenzhen 518060, China. yxcheng@szu.edu.cn.
9
School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, China. jli_henantcm2017@163.com.

Abstract

Nine new gingerols, including three 6-oxo-shogaol derivatives [(Z)-6-oxo-[6]-shogaol (1), (Z)-6-oxo-[8]-shogaol (2), (Z)-6-oxo-[10]-shogaol (3)], one 6-oxoparadol derivative [6-oxo-[6]-paradol (4)], one isoshogaol derivative [(E)-[4]-isoshogaol (5)], and four paradoldiene derivatives [(4E,6Z)-[4]-paradoldiene (8), (4E,6E)-[6]-paradoldiene (9), (4E,6E)-[8]-paradoldiene (10), (4E,6Z)-[8]-paradoldiene (11)], together with eight known analogues, were isolated from the rhizoma of Zingiber officinale. Their structures were elucidated on the basis of spectroscopic data. It was noted that the isolation of 6-oxo-shogaol derivatives represents the first report of gingerols containing one 1,4-enedione motif. Their structures were elucidated on the basis of spectroscopic and HRESIMS data. All the new compounds were evaluated for their cytotoxic activities against human cancer cells (MCF-7, HepG-2, KYSE-150).

KEYWORDS:

Zingiber officinale; cytotoxic activity; gingerols

PMID:
29393873
PMCID:
PMC6017651
DOI:
10.3390/molecules23020315
[Indexed for MEDLINE]
Free PMC Article

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