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Anti-inflammatory naphthoquinone-monoterpene adducts and neolignans from Eugenia caryophyllata
Xue-Yi Li1, Jun Jiang1, Beiyi Shu1
1State Key Laboratory of Bioactive Molecules and Druggability Assessment, Jinan University, Guangzhou 510632, People's Republic of China; Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Guangdong-Hong Kong-Macau Join Laboratory for Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, People's Republic of China; Center for Bioactive Natural Molecules and Innovative Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, People's Republic of China.
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.
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