3 years ago

Bioactive Asarone-Derived Phenylpropanoids from the Rhizome of Acorus tatarinowii Schott

Bioactive Asarone-Derived Phenylpropanoids from the Rhizome of Acorus tatarinowii Schott
Rong-Rong He, Jian Zou, Yang Yu, Xiao-Lin Feng, En Gao, Hao Gao, Zheng-Qun Zhou, Guo-Dong Chen, Xin-Sheng Yao
Eight new (1a/1b, 2a, 3a, 4a/4b, and 5a/5b) and seven known (2b, 3b, and 610) asarone-derived phenylpropanoids, a known asarone-derived lignan (12), and four known lignan analogues (11 and 1315) were isolated from the rhizome of Acorus tatarinowii Schott. The structures were elucidated via comprehensive spectroscopic analyses, modified Mosher’s method, and quantum chemical calculations. Compounds 18 were present as enantiomers, and 15 were successfully resolved via chiral-phase HPLC. Compounds 1a/1b were the first cases of asarone-derived phenylpropanoids with an isopropyl C-3 side-chain tethered to a benzene core from nature. Hypoglycemic, antioxidant, and AChE inhibitory activities of 115 were assessed by the α-glucosidase inhibitory, ORAC, DPPH radical scavenging, and AChE inhibitory assays, respectively. All compounds except 3a showed α-glucosidase inhibitory activity. Compound 3b has the highest α-glucosidase inhibitory effect with an IC50 of 80.6 μM (positive drug acarbose IC50 of 442.4 μM). In the antioxidant assays, compounds 1315 exhibited ORAC and DPPH radical scavenging activities. The results of the AChE inhibitory assay indicated that all compounds exhibited weak AChE inhibitory activities.

Publisher URL: http://dx.doi.org/10.1021/acs.jnatprod.7b00457

DOI: 10.1021/acs.jnatprod.7b00457

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