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ARS Home » Southeast Area » Oxford, Mississippi » Natural Products Utilization Research » Research » Publications at this Location » Publication #330980
Research Project: Discovery and Development of Natural Products for Pharmaceutical and Agrochemical Applications II

Location: Natural Products Utilization Research

Title: A New Metabolite with a unique 4-pyranone-ylactam-1,4-thiazine moiety from a Hawaiian-plant associated fungus

Author
item LI, CHUN-SHUN - University Of Hawaii
item DING, YUANQING - University Of Mississippi
item YANG, BAO-JUN - University Of Hawaii
item MIKLOSSY, GABRIELLA - University Of Hawaii
item YIN, HONG-QUAN - University Of Mississippi
item WALKER, LARRY - University Of Mississippi
item TURKSON, JAMES - University Of Hawaii
item CAO, SHUGENG - University Of Hawaii

Submitted to: Organic Letters
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 6/24/2015
Publication Date: 6/24/2015
Citation: Li, C., Ding, Y., Yang, B., Miklossy, G., Yin, H., Walker, L.A., Turkson, J., Cao, S. 2015. A New Metabolite with a unique 4-pyranone-ylactam-1,4-thiazine moiety from a Hawaiian-plant associated fungus. Organic Letters. 17(14):3556-9. doi:10.1021/acs.orglett.5b01650.

Interpretive Summary: One unusual compound along with two new compounds and a known compound were isolated from an endophytic fungus Paraphaeosphaeria neglecta FT462 obtained from the Hawaiian-plant Lycopodiellacernua (L.) Pic. Serm. Their structures were characterized by NMR and MS spectroscopic analysis. The absolute configuration of the unusual compound was determined by electronic circular dichroism (ECD). Paraphaeosphaeride C showed STAT3 inhibition.

Technical Abstract: 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-'-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.