Targeted isolation of antiviral cinnamoylphloroglucinol-terpene adducts from Cleistocalyx operculatus by building blocks-based molecular networking approach.

ABSTRACT: The building blocks-based molecular network (BBMN) strategy was applied to the phytochemical investigation of Cleistocalyx operculatus, leading to the targeted isolation of eighteen novel cinnamoylphloroglucinol-terpene adducts (CPTAs) with diverse skeleton types (cleistoperones A-R, 1-18). Their structures including absolute configurations were determined by extensive spectroscopic methods, quantum chemical calculations, and single-crystal X-ray crystallographic experiments. Cleistoperone A (1), consisting of a cinnamoylphloroglucinol motif and two linear monoterpene moieties, represents an unprecedented macrocyclic CPTA, whose densely functionalized tricyclo[15.3.1.0^3,8]heneicosane bridge ring skeleton contains an enolizable β,β'-trike

SUBMITTER: Song J 

PROVIDER: S-EPMC11544174 | biostudies-literature | 2024 Oct

REPOSITORIES: biostudies-literature