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Stilbenoids and cannabinoids from the leaves of Cannabis sativa f. sativa with potential reverse cholesterol transport activity

Abstract

Three new stilbenoids (1-3), and 16 known stilbenoids (4-6) and cannabinoids (7-19) were isolated from the leaves of Hemp (Cannabis sativa L.). The structures of the three new compounds were identified as α,α'-dihydro-3',4,5'-trihydroxy-4'-methoxy-3-isopentenylstibene (HM1), α,α'-dihydro-3,4',5-trihydroxy-4-methoxy-2,6-diisopentenylstibene (HM2), α,α'-dihydro-3',4,5'-trihydroxy-4'-methoxy-2',3-diisopentenylstibene (HM3) by 1D and 2D NMR spectroscopy, LC-MS, and HRESIMS. The known α,α'-dihydro-3,4',5-trihydroxy-4,5'-diisopentenylstibene (5) and combretastatin B-2 (6) were isolated for the first time from C. sativa f. sativa. These isolated compounds exhibited cytotoxic effects on human cancer cells via inhibiting cancer cells proliferation and inducing cell death. Among them, compound 4, 5, 10, 12, 13, 15, and 19 displayed broad-spectrum cytotoxicity, and 1, 7, and 11 displayed selectivity in inhibition efficiency on MCF-7 and A549 cells, which suppressed significantly cancer cells proliferation by inducing cell death. Their effects of compounds 1-3 on improving reverse cholesterol transport (RCT) were evaluated by isotope-tracing and western blotting. Results showed that the three stilbenoids showed cytotoxicity above 1.0 mg/L, especially that of HM3. They could improve [3H]-cholesterol efflux from Raw 264.7 macrophages to high density lipoprotein by enhancing the proteins expression of ABCG1 and SR-B1, and HM1 and HM2 showed significant different compared with fenofibrate at 1.0 mg/L. The three stilbenoids could also significantly improve the protein expressin of ABCA1. Further study in HepG2 cells indicated that they improve the proteins expression of LDLR, SR-B1 and CYP7A1, especially that of HM1 and HM3. However, they showed no significant effect on PCSK9. The above results indicated that these stilbenoids may elevate the transfer of cholesterol to hepatocytes by improving proteins expression of SR-B1 and LDLR, and the synthesis of bile acid by increasing protein expression of CYP7A1. In conclusion, HM1 showed lower cytotoxicity and higher activity on improving RCT-related proteins expression. Our study suggests that It may be explored as a novel lipid-lowering drug and as beneficial ingredient in health functional foods and pharmaceuticals.

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Supplementary files

Publication details

The article was received on 27 Sep 2018, accepted on 31 Oct 2018 and first published on 01 Nov 2018


Article type: Paper
DOI: 10.1039/C8FO01896K
Citation: Food Funct., 2018, Accepted Manuscript
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    Stilbenoids and cannabinoids from the leaves of Cannabis sativa f. sativa with potential reverse cholesterol transport activity

    Q. Liu, T. Guo, P. Hou, F. Li, S. Guo, W. Song, H. Zhang, J. Zhang, N. Bai and C. Ho, Food Funct., 2018, Accepted Manuscript , DOI: 10.1039/C8FO01896K

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