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A New Metabolite with a Unique 4‑Pyranone−γ-Lactam–1,4-Thiazine Moiety from a Hawaiian-Plant Associated Fungus

An endophytic fungus Paraphaeosphaeria neglecta FT462 isolated from the Hawaiian-plant Lycopodiella cernua (L.) Pic. Serm produced one unusual compound (1, paraphaeosphaeride A) with the 4-pyranone−γ-lactam–1,4-thiazine moiety, along with two new compounds (2 and 3, paraphaeosphaerides B and C, resp...

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Bibliographic Details
Published in:Organic letters 2015-07, Vol.17 (14), p.3556-3559
Main Authors: Li, Chun-Shun, Ding, Yuanqing, Yang, Bao-Jun, Miklossy, Gabriella, Yin, Hong-Quan, Walker, Larry A, Turkson, James, Cao, Shugeng
Format: Article
Language:English
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Summary:An endophytic fungus Paraphaeosphaeria neglecta FT462 isolated from the Hawaiian-plant Lycopodiella cernua (L.) Pic. Serm produced one unusual compound (1, paraphaeosphaeride A) with the 4-pyranone−γ-lactam–1,4-thiazine moiety, along with two new compounds (2 and 3, paraphaeosphaerides B and C, respectively) and the known compound (4). Compounds 1–3 were characterized by NMR and MS spectroscopic analysis. The absolute configuration of the 3-position of compound 1 was determined as S by electronic circular dichroism (ECD) calculations. Compound 3 also showed STAT3 inhibition at 10 μM.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01650