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seco-Sesquiterpenes and acorane-type sesquiterpenes with antiviral activity from the twigs and leaves of Illicium henryi Diels
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Yong, Jin-Yao, Li, Mi, Li, Wen-Rui, Gao, Rong-Mei, Su, Guo-Zhu, Wang, Hai-Qiang, Yang, Jia, Li, Li, Li, Yu-Huan, Scott, Peter, Wang, Ru-Bing, Wang, Xiao-Jing and Ma, Shuang-Gang (2023) seco-Sesquiterpenes and acorane-type sesquiterpenes with antiviral activity from the twigs and leaves of Illicium henryi Diels. Bioorganic Chemistry, 131 . 106324. doi:10.1016/j.bioorg.2022.106324 ISSN 0045-2068.
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Official URL: https://doi.org/10.1016/j.bioorg.2022.106324
Abstract
Chemical investigation of an alcohol extract from the twigs and leaves of Illicium henryi Diels resulted in the isolation of two new acorane-related seco-sesquiterpenes (1 and 3), two new acorane-related seco-norsesquiterpenes (2 and 4), one new 2-epi-cedrane sesquiterpene (5), eight new acorane-type sesquiterpenes (6-13), and a known major constituent of acorenone B (14). Their structures were established by interpreting extensive spectroscopic data, including HRESIMS, NMR ( H and C NMR, H- H COSY, HSQC, and HMBC), and NOE difference spectra analysis. The absolute configurations of 1, 2, 4-7, 9, 10, and 14 were determined by X-ray crystallography, while chemical transformation methods were performed with compound 14 as the starting material to elegantly solve the absolute configuration issue of compounds 8 and 11-13. Notably, 1 and 2 are seco-sesquiterpenes that are related to acorane and possess an unusual ketal-linked hemiacetal in a 6,8-dioxabicyclo[3.2.1]octan-7-ol scaffold ring system. Plausible biosynthetic pathways for compounds 1-14, which were derived from the acorane skeleton, were proposed. All the isolated compounds (1-14) were evaluated for their antiviral and cytotoxic activities.
Item Type: | Journal Article | |||||||||
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Subjects: | Q Science > QK Botany | |||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | |||||||||
SWORD Depositor: | Library Publications Router | |||||||||
Library of Congress Subject Headings (LCSH): | Illicium , Illicium -- Analysis, Sesquiterpenes , Plant products -- Synthesis, Botanical chemistry | |||||||||
Journal or Publication Title: | Bioorganic Chemistry | |||||||||
Publisher: | Academic Press | |||||||||
ISSN: | 0045-2068 | |||||||||
Official Date: | February 2023 | |||||||||
Dates: |
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Volume: | 131 | |||||||||
Article Number: | 106324 | |||||||||
DOI: | 10.1016/j.bioorg.2022.106324 | |||||||||
Status: | Peer Reviewed | |||||||||
Publication Status: | Published | |||||||||
Access rights to Published version: | Restricted or Subscription Access | |||||||||
Date of first compliant deposit: | 7 February 2023 | |||||||||
Date of first compliant Open Access: | 14 December 2023 | |||||||||
RIOXX Funder/Project Grant: |
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