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Lanostane Triterpenoids with Glucose-uptake Stimulatory activity from Peels of the cultivated edible mushroom Wolfiporia cocos.

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 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 benefit for the glucose uptake-stimulating and insulin-sensitizing activities. Furthermore, the the 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 functional food or dietary supplements.