期刊
ORGANIC CHEMISTRY FRONTIERS
卷 8, 期 22, 页码 6196-6202出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo01066b
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资金
- National Natural Science Foundation of China [32070391, 82003605, 31700043]
- Central Public-Interest Scientific Institution Basal Research Fund [Y2021XK25]
Janthinoid A and andrastone I are two meroterpenoids isolated from an endophytic fungus, showing significant in vivo anti-tumor activities against NSCLC cells. The structure of Janthinoid A is a novel type of meroterpenoid, synthesized through a unique biosynthetic pathway.
Janthinoid A (1), an unprecedented C-22 meroterpenoid featuring a highly modified bridged 4a,1-(epoxymethano)phenanthrene scaffold incorporating eight continuous quaternary carbons, along with its biosynthetic-related C-25 analogue andrastone I (2), were isolated from the endophytic fungus Penicillium janthinellum TE-43. Their structures were unambiguously established by comprehensive analyses of spectroscopic data, quantum chemical calculations, and X-ray diffraction. The tri-nor-meroterpenoid skeleton of 1 was produced by a unique biosynthetic pathway, involving the ring cleavage and continuous carbon degradations of the aromatic polyketide precursor, which is distinct from the commonly-observed meroterpenoids both structurally and biogenetically, representing a new type of meroterpenoid. Both compounds showed significant in vivo anti-tumor activities against NSCLC cells A549.
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