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

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posted on 2018-07-02, 04:44 authored by 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
Four novel phloroglucinol derivatives (14) 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 and 2 are two pairs of new enantiomeric phloroglucinol dimers possessing an unprecedented polycyclic skeleton with a highly functionalized dihydropyrano­[3,2-d]­xanthene tetracyclic core. Compounds 3 and 4 are two new phloroglucinol-terpene adducts (PTAs) with a novel carbon skeleton. The structures of 14 including their absolute configurations were unambiguously accomplished by combination of extensive spectroscopic analyses, X-ray crystallography, and quantum chemical ECD calculations. A hypothetical biosynthetic pathway for 14 was also proposed. Compound 1 exhibited a promising in vitro antiherpes simplex virus type-1 (HSV-1) effect.

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