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J Agric Food Chem. 2017 Jul 26;65(29):5926-5934. doi: 10.1021/acs.jafc.7b01477. Epub 2017 Jul 11.

Further New Gypenosides from Jiaogulan (Gynostemma pentaphyllum).

Author information

1
CAS Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences (CAS) , Lanzhou 730000, People's Republic of China.
2
University of Chinese Academy of Sciences , Beijing 100039, People's Republic of China.
3
College of Chemistry and Chemical Engineering, Lanzhou University , Lanzhou, Gansu 730000, People's Republic of China.

Abstract

Jiaogulan (Gynostemma pentaphyllum) has been widely used as a herbal tea, dietary supplement, and vegetable in Asian countries. In this study, six new gypenosides (1-6) were isolated from the aerial parts of G. pentaphyllum. Their molecular structures were elucidated through spectroscopic analysis and acid hydrolysis. Gypenosides 1 and 2 represented the first example of a dammar-21-O- glucopyranoside without any unsaturated functional group and a dammar-3-O-glucopyranosyl-25-O-glucopyranoside without any cyclization in the side chain, respectively. In addition, gypenosides 5 and 6 exhibited the first example of a 24-hydroperoxy-19-oxo-dammarane triterpenoid and 19-oxo-dammar-21-O-glucopyranoside with a saturated side chain, respectively. Gypenoside 5 was found to possess protein tyrosine phosphatase 1B inhibitory activity, with an IC50 value of 8.2 ± 0.9 μM, and moderate cytotoxicity against human breast cancer cells MCF7, MCF7/ADR, and MDA-MB-231, with IC50 values ranging from 10.5 ± 1.4 to 14.2 ± 2.6 μM. The outcome of the study provided crucial information regarding the structural diversity and health benefits of gypenosides.

KEYWORDS:

Gynostemma pentaphyllum; PTP1B inhibitory activity; cytotoxicity; jiaogulan; new gypenosides

PMID:
28662582
DOI:
10.1021/acs.jafc.7b01477
[Indexed for MEDLINE]

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