Chartspiroton, a Tetracyclic Spiro-naphthoquinone Derivative from a Medicinal Plant Endophytic <i>Streptomyces</i>
Huimin Zhao, Aiping Yang, Jian Liu, Sheng Bao, Peng Ren, Yang Hu, Tianjie Yuan, Shurong Hou, Tian Xie, Qichun Zhang, Xiabin Chen, Xiachang Wang, Lihong Hu
Abstract
A novel 6/6/5/6 tetracyclic polyketide named chartspiroton (1) was isolated from a medicinal plant endophytic Streptomyces in Dendrobium officinale. The complete structure assignment with absolute stereochemistry was elucidated through spectroscopic data, computational calculations, and single-crystal X-ray diffraction. Chartspiroton features an unprecedented naphthoquinone derivative spiro-fused with a benzofuran lactone moiety. A plausible polyketide biosynthetic pathway for 1 suggested intriguing oxidative rearrangement steps to form the five-membered lactone ring.
Topics & Concepts
PolyketideChemistryNaphthoquinoneMoietyStereochemistryDerivative (finance)Ring (chemistry)LactoneStreptomycesBenzofuranBiosynthesisOrganic chemistryBiologyGeneticsEconomicsFinancial economicsBacteriaEnzymeBiological and pharmacological studies of plantsPlant and Fungal Species DescriptionsPlant and animal studies