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

Org Lett. 2015 Jul 17;17(14):3556-9. doi: 10.1021/acs.orglett.5b01650. Epub 2015 Jun 24.

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-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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fungi / chemistry*
  • Fungi / isolation & purification
  • Hawaii
  • Lactams / chemical synthesis*
  • Lactams / chemistry*
  • Lactams / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plants / chemistry*
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry*
  • Pyrones / isolation & purification
  • Stereoisomerism
  • Thiazines / chemistry*
  • Thiazines / metabolism*

Substances

  • Lactams
  • Pyrones
  • Thiazines
  • paraphaeosphaeride A
  • paraphaeosphaeride B
  • paraphaeosphaeride C