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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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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.

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

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Publication details

The article was received on 27 Jan 2018, accepted on 31 Mar 2018 and first published on 02 Apr 2018


Article type: Research Article
DOI: 10.1039/C8QO00095F
Citation: Org. Chem. Front., 2018, Advance Article
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    Lithocarpins A–D: four tenellone-macrolide conjugated [4 + 2] hetero-adducts from the deep-sea derived fungus Phomopsis lithocarpus FS508

    J. Xu, H. Tan, Y. Chen, S. Li, Z. Huang, H. Guo, H. Li, X. Gao, H. Liu and W. Zhang, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00095F

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