1. Anti-inflammatory naphthoquinone-monoterpene adducts and neolignans from Eugenia caryophyllata.
- Author
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Li, Xue-Yi, Jiang, Jun, Shu, Beiyi, Huang, Rui-Li, Yang, Hai-Xia, Chen, Ya-Li, Tang, Wei, Ye, Wen-Cai, Wang, Ying, Huang, Xiao-Jun, and Song, Jian-Guo
- Subjects
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PHYTOTHERAPY , *ANTI-inflammatory agents , *IN vitro studies , *QUINONE , *TERPENES , *PHYTOCHEMICALS , *RESPIRATORY syncytial virus infections , *EDIBLE plants , *ANTIVIRAL agents , *CARBOCYCLIC acids , *LIGNANS , *SPECTRUM analysis , *X-rays , *CRYSTALLOGRAPHY - Abstract
A phytochemical investigation on the buds of edible medicinal plant, Eugenia carvophyllata , led to the discovery of seven new compounds, caryophones A–G (1 – 7), along with two biogenetically-related known ones, 2-methoxy-7-methyl-1,4-naphthalenedione (8) and eugenol (9). Compounds 1 – 3 represent the first examples of C-5–C-1′ connected naphthoquinone-monoterpene adducts with a new carbon skeleton. Compounds 4 – 7 are a class of novel neolignans with unusual linkage patterns, in which the C-9 position of one phenylpropene unit coupled with the aromatic core of another phenylpropene unit. The chemical structures of the new compounds were determined based on extensive spectroscopic analysis, X-ray diffraction crystallography, and quantum-chemical calculation. Among the isolates, compounds (−)- 2 , 3 , 6 , and 9 showed significant in vitro inhibitory activities against respiratory syncytial virus (RSV)-induced nitric oxide (NO) production in RAW264.7 cells. [Display omitted] [ABSTRACT FROM AUTHOR]
- Published
- 2024
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