Cucurbitane-type triterpenoids from the vines of Momordica charantia and their anti-inflammatory, cytotoxic, and antidiabetic activity

Chia-Ching Liaw; Hung-Tse Huang; Hui-Kang Liu; Yu-Chi Lin; Li-Jie Zhang; Wen-Chi Wei; Chien-Chang Shen; Chia-Lun Wu; Chung-Yi Huang; Yao-Haur Kuo

doi:10.1016/j.phytochem.2021.113026

Cucurbitane-type triterpenoids from the vines of Momordica charantia and their anti-inflammatory, cytotoxic, and antidiabetic activity

Phytochemistry. 2022 Mar:195:113026. doi: 10.1016/j.phytochem.2021.113026. Epub 2021 Dec 7.

Authors

Affiliations

¹ National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, 11201, Taiwan; Department of Biochemical Science and Technology, National Chiayi University, Chiayi, 60004, Taiwan.
² National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, 11201, Taiwan; Department of Biochemical Science & Technology, National Taiwan University, Taipei, 10617, Taiwan.
³ National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, 11201, Taiwan.
⁴ National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, 11201, Taiwan; Department of Marine Biotechnology and Resources, National Sun Ya-sen University, Kaohsiung, 80424, Taiwan.
⁵ National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, 11201, Taiwan; Department of Food Science, National Ilan University, Ilan, 26047, Taiwan.
⁶ Department of Food Science, National Ilan University, Ilan, 26047, Taiwan. Electronic address: cyhuang@niu.edu.tw.
⁷ National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, 11201, Taiwan; Graduate Institute of Integrated Medicine, College of Chinese Medicine, China Medical University, Taichung, 40402, Taiwan. Electronic address: kuoyh@nricm.edu.tw.

PMID: 34890886
DOI: 10.1016/j.phytochem.2021.113026

Abstract

Phytochemical investigation of the ethanol extract from wild Momordica charantia vines has resulted in isolation of seven cucurbitane-type triterpenoids, including six undescribed compounds, kuguaovins H‒M, and the known compound, momordicoside K. The structures of the isolated compounds were elucidated on the basis of spectroscopic analyses, including 1D and 2D NMR, and MS experiments. The chemical structure of momordicoside K was determined for the first time by X-ray crystallographic analysis and its absolute configuration assigned. The cytotoxicity against four human tumor cell lines and anti-inflammatory activities on LPS-stimulated RAW264.7 macrophages were evaluated. Of the isolates, kaguaovin L exhibited potential cytotoxicity against MCF-7, HEp-2, Hep-G2, and WiDr cancer cell lines and showed moderate anti-NO production activity. In addition, kuguaovins H and J also showed the stimulatory effect of GLP-1 secretion on the murine intestinal secretin tumor cell line (STC-1).

Keywords: Anti-inflammatory activity; Cucurbitaceae; Cucurbitane-type triterpenoids; Cytotoxicity; GLP-1 secretion; Kuguaovins; Momordica charantia.

MeSH terms

Animals
Anti-Inflammatory Agents / pharmacology
Glycosides
Hypoglycemic Agents / pharmacology
Mice
Molecular Structure
Momordica charantia*
Triterpenes* / pharmacology

Substances

Anti-Inflammatory Agents
Glycosides
Hypoglycemic Agents
Triterpenes
cucurbitane