Chiral resolution, absolute configuration, and bioactivity of a new racemic asarone derivative from the rhizome of Acorus tatarinowii

A new asarone-derived racemate (1) was isolated from the rhizome of Acorus tatarinowii. The structure of 1 was established by comprehensive spectroscopic analyses, and it was successfully resolved by chiral HPLC, demonstrating that it is racemic. The absolute configurations of 1a [(−)-acortatarone A...

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Bibliographic Details
Published in:Fitoterapia 2017-10, Vol.122, p.7-10
Main Authors: Gao, En, Ren, Fei-Fei, Zou, Jian, Yu, Yang, Fan, Hong-Xia, Zhou, Zheng-Qun, Chen, Guo-Dong, He, Rong-Rong, Yao, Xin-Sheng, Gao, Hao
Format: Article
Language:English
Subjects:
Absolute configuration
Acarbose
ACE inhibitors
Acetylcholinesterase
Acetylcholinesterase (AChE) inhibitory assay
Acorus
Acorus tatarinowii
Aromatic compounds
Asarone derivatives
Asarones
Biological activity
Chemical compounds
Configurations
Glucose
Glucosidase
Herbal medicine
High-performance liquid chromatography
Liquid chromatography
Quantum chemistry
Racemate
Spectrum analysis
α-Glucosidase
α-Glucosidase inhibitory assay
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Summary:A new asarone-derived racemate (1) was isolated from the rhizome of Acorus tatarinowii. The structure of 1 was established by comprehensive spectroscopic analyses, and it was successfully resolved by chiral HPLC, demonstrating that it is racemic. The absolute configurations of 1a [(−)-acortatarone A] and 1b [(+)-acortatarone A] were determined using quantum chemical calculations. Compounds 1a and 1b were the first cases of asarone derivatives with the 5,7-dialkyl-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one core. The α-glucosidase inhibitory and acetylcholinesterase (AChE) inhibitory activities of 1 were evaluated, and it exhibited α-glucosidase inhibitory activity with potency close to that of the positive control (acarbose). [Display omitted]
ISSN:0367-326X
1873-6971
DOI:10.1016/j.fitote.2017.08.004