Lithocarpins A–D: four tenellone-macrolide conjugated [4 + 2] hetero-adducts from the deep-sea derived fungus Phomopsis lithocarpus FS508

Jianlin Xu; Haibo Tan; Yuchan Chen; Saini Li; Zilei Huang; Heng Guo; Haohua Li; Xiaoxia Gao; Hongxin Liu; Weimin Zhang

doi:10.1039/C8QO00095F

Lithocarpins A–D: four tenellone-macrolide conjugated [4 + 2] hetero-adducts from the deep-sea derived fungus Phomopsis lithocarpus FS508†

Jianlin Xu,^ab Haibo Tan,

^c Yuchan Chen,^a Saini Li,^a Zilei Huang,^a Heng Guo,^ab Haohua Li,^a Xiaoxia Gao,^b Hongxin Liu*^a and Weimin Zhang

*^a

Author affiliations

* Corresponding authors

^a State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China
E-mail: [email protected]

^b College of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, China

^c Program for Natural Products Chemical Biology, Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, China

Abstract

Lithocarpins A–D (1–4), the first examples of highly oxygenated tenellone-macrolide conjugated dimers, were isolated from the deep-sea derived fungus Phomopsis lithocarpus FS508. Their structures were elucidated by extensive spectroscopic analyses and X-ray diffraction techniques. Their plausible biogenetic pathways suggested a very intriguing and unusual [4 + 2] cycloaddition with an isobenzofuran as an electron-donating diene. Lithocarpins C and D exhibited a moderate inhibitory effect against three tumor cell lines with IC₅₀ values ranging from 17.0 to 21.6 μM.

Organic Chemistry Frontiers

Lithocarpins A–D: four tenellone-macrolide conjugated [4 + 2] hetero-adducts from the deep-sea derived fungus Phomopsis lithocarpus FS508†

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Lithocarpins A–D: four tenellone-macrolide conjugated [4 + 2] hetero-adducts from the deep-sea derived fungus Phomopsis lithocarpus FS508

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