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Lanostane Triterpenoids with Glucose-Uptake-Stimulatory Activity from Peels of the Cultivated Edible Mushroom Wolfiporia cocos

Author:
Chen, Baosong, Zhang, Jinjin, Han, Junjie, Zhao, Ruilin, Bao, Li, Huang, Ying, Liu, Hongwei
Source:
Journal of agricultural and food chemistry 2019 v.67 no.26 pp. 7348-7364
ISSN:
1520-5118
Subject:
Wolfiporia cocos, adipocytes, animal disease models, chemical bonding, circular dichroism spectroscopy, cytotoxicity, dietary supplements, functional foods, glucose, high fat diet, inhibitory concentration 50, mice, mushrooms, nuclear magnetic resonance spectroscopy, obesity, structure-activity relationships, triterpenoids
Abstract:
A chemical study on the peels of the cultivated edible mushroom Wolfiporia cocos led to the isolation and identification of 47 lanostane triterpenoids including 16 new compounds (1–16). The structures of the new compounds were determined by analysis of the NMR, MS, and electronic circular dichroism (ECD) data. Compounds 1 and 2 represent new members of the family of 4,5-secolanostane triterpenes. Compound 3 is a new aromatic lanostane triterpene with an unusual methyl rearrangement from C-10 to C-6. The absolute configurations of 1 and 8 were assigned by ECD spectra calculation. All compounds were evaluated for cytotoxicity (K562, SW480, and HepG2) and glucose-uptake-stimulating effects. Compounds 23, 25, 29, and 31 showed weak inhibition on the K562 cells with IC₅₀ in the range of 25.7 to 68.2 μM, respectively. Compounds 21, 28, and 30 increased the glucose uptake in 3T3-L1 cells by 25%, 14%, and 50% at 5 μM, respectively. In addition, compounds 14, 23, 29, 35, and 43 showed insulin-sensitizing activity by increasing the insulin-stimulated glucose uptake at 2.5 μM in 3T3-L1 adipocytes. A preliminary structure–activity relationship analysis indicates that the 6/6/6/5 ring skeleton and the double bond between C-8 and C-9 are beneficial for the glucose-uptake-stimulating and insulin-sensitizing activities. Furthermore, the alkaline-insoluble fraction mainly containing compounds 22, 24, 28, and 31 were confirmed to have hypoglycemic and hypolipidemic activity on high-fat-diet-induced obese mice. This work confirms the potential of the peels’ extracts of W. cocos as a functional food or dietary supplements.
Agid:
6492586