Discovery of Cyclic Diarylheptanoids as Inhibitors against Influenza A Virus from the Roots of Casuarina equisetifolia

Xiaoyu Xu; Liurong Chen; Yucai Luo; Ruanling Gao; Yingting Xu; Jie Yang; Zhongyu Zhou; Xiaoyi Wei

doi:10.1021/acs.jnatprod.2c00335

Discovery of Cyclic Diarylheptanoids as Inhibitors against Influenza A Virus from the Roots of Casuarina equisetifolia

J Nat Prod. 2022 Sep 23;85(9):2142-2148. doi: 10.1021/acs.jnatprod.2c00335. Epub 2022 Aug 30.

Authors

Xiaoyu Xu^{1

2}, Liurong Chen³, Yucai Luo^{1

4}, Ruanling Gao¹, Yingting Xu^{1

4}, Jie Yang³, Zhongyu Zhou^{1

4}, Xiaoyi Wei^{1

4}

Affiliations

¹ Key Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement & Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, China.
² Institute of Crop Sciences, Fujian Academy of Agricultural Sciences, Fuzhou 350013, China.
³ Guangdong Provincial Key Laboratory of New Drug Screening, Guangzhou Key laboratory of Drug Research for Emerging Virus Prevention and Treatment, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China.
⁴ University of Chinese Academy of Sciences, Beijing 100049, China.

PMID: 36040315
DOI: 10.1021/acs.jnatprod.2c00335

Abstract

Four new cyclic diarylheptanoids, casuarinols A-C (1-3) and casuarinolide A (4), together with six known ones (5-10), were isolated from the roots of Casuarina equisetifolia. Structures were elucidated by extensive spectroscopic analysis, theoretical conformational, and electronic circular dichroism analyses. Casuarinol C (3) is a novel cyclic diarylheptanoid-aldehyde adduct. Casuarinolide A (4) represents the first structure of a seco-cyclic diarylheptanoid. Compounds 1-9 were evaluated for their anti-influenza A virus (IAV) activity against A/WSN/33 (H1N1). (-)-(M)-11-Oxo-3,12R,17-trihydroxy-9-ene-[7,0]-metacyclophane (5) displayed significant anti-IAV activity with an IC₅₀ value of 8.64 ± 2.49 μM and a CC₅₀ higher than 100 μM.

MeSH terms

Aldehydes / chemistry
Diarylheptanoids* / chemistry
Diarylheptanoids* / isolation & purification
Diarylheptanoids* / pharmacology
Influenza A Virus, H1N1 Subtype* / drug effects
Molecular Structure
Plant Roots* / chemistry

Substances

Aldehydes
Diarylheptanoids