Phloroglucinol Derivatives with Unusual Skeletons from Cleistocalyx operculatus and Their in Vitro Antiviral Activity

• DOI: 10.1021/acs.joc.8b01050
• Publication Date: 2018-07-02T13:10:19Z
• Authors: Jun-Cheng Su; Shan Wang; Wen Cheng; Xiao-Jun Huang; Man-Mei Li; Ren-Wang Jiang; Yao-Lan Li; Lei Wang; Wen-Cai Ye; Ying Wang
• Keywords: Phloroglucinol

Four novel phloroglucinol derivatives (1-4) featuring a 2,4-dimethyl-cinnamyl-phloroglucinol moiety, along with their putative biosynthetic precursors 5 and 6, were isolated from the leaves of Cleistocalyx operculatus. Compounds 1 2 are two pairs new enantiomeric dimers possessing an unprecedented polycyclic skeleton highly functionalized dihydropyrano[3,2- d]xanthene tetracyclic core. 3 4 phloroglucinol-terpene adducts (PTAs) carbon skeleton. The structures 1-4 including absolute configurations unambiguously accomplished by combination extensive spectroscopic analyses, X-ray crystallography, quantum chemical ECD calculations. A hypothetical pathway for was also proposed. Compound exhibited promising in vitro antiherpes simplex virus type-1 (HSV-1) effect.