Lithocarpins A–D: four tenellone-macrolide conjugated [4 + 2] hetero-adducts from the deep-sea derived fungus Phomopsis lithocarpus FS508. Issue 11 (17th April 2018)

• Record Type: Journal Article
• Authors: Xu, Jianlin; Tan, Haibo; Chen, Yuchan; Li, Saini; Huang, Zilei; Guo, Heng; Li, Haohua; Gao, Xiaoxia; Liu, Hongxin; Zhang, Weimin
• Is Part Of: Organic chemistry frontiers. Volume 5:Issue 11(2018)
• Page Start: 1792
• Page End: 1797
• Publication Date: 2018-04-17
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c8qo00095f
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Lithocarpins A–D, four novel tenellone-macrolide conjugated dimers containing a fascinating 9, 14-epoxynaphtho[2, 3- e ]oxecin-3(2 H )-one skeleton. 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.