(±)-Heterocageflavone, anti-inflammatory isoprenylated flavonoids with a tricyclo[5.3.1.03,8]undecane moiety from Artocarpus heterophyllus

Gang Ren; Li-She Gan; Ling-Zhi Zhu; Hui-Ting Zeng; Fan Xu; Tao Yuan

doi:10.1016/j.bioorg.2022.105742

(±)-Heterocageflavone, anti-inflammatory isoprenylated flavonoids with a tricyclo[5.3.1.0^3,8]undecane moiety from Artocarpus heterophyllus

Bioorg Chem. 2022 Jun:123:105742. doi: 10.1016/j.bioorg.2022.105742. Epub 2022 Mar 22.

Authors

Gang Ren¹, Li-She Gan², Ling-Zhi Zhu³, Hui-Ting Zeng⁴, Fan Xu⁵, Tao Yuan⁶

Affiliations

¹ Research Center of Natural Resources of Chinese Medicinal Materials and Ethnic Medicine, Jiangxi University of Chinese Medicine, Nanchang 330004, China.
² School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020, China; College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China.
³ Research Center of Natural Resources of Chinese Medicinal Materials and Ethnic Medicine, Jiangxi University of Chinese Medicine, Nanchang 330004, China; Jiangxi Academy of Forestry, Nanchang 330032, China.
⁴ College of Life Sciences, Jiangxi Normal University, Nanchang 330022, China.
⁵ College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China.
⁶ College of Life Sciences, Jiangxi Normal University, Nanchang 330022, China. Electronic address: tyuan@jxnu.edu.cn.

PMID: 35378373
DOI: 10.1016/j.bioorg.2022.105742

Abstract

(±)-Heterocageflavone (1), a pair of enantiomeric isoprenylated flavonoids, were isolated from Artocarpus heterophyllus. Compound 1 incorporates an unusual tricyclo[5.3.1.0^3,8]undecane moiety, forming a unique caged polycyclic system. The structures of the pair were determined by spectroscopic analysis, ECD calculations, and single-crystal X-ray diffraction. Compound 1 showed significant inhibitory activity against LPS-induced NO production in RAW264.7 cells with an IC₅₀ value of 49.2 μM.

Keywords: Anti-inflammatory; Artocarpus heterophyllus; Enantiomeric; Isoprenylated flavonoids.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkanes
Anti-Inflammatory Agents / pharmacology
Artocarpus* / chemistry
Flavonoids / chemistry
Flavonoids / pharmacology

Substances

Alkanes
Anti-Inflammatory Agents
Flavonoids
undecane