Sesteralterin and Tricycloalterfurenes A-D: Terpenes with Rarely Occurring Frameworks from the Marine-Alga-Epiphytic Fungus Alternaria alternata k21-1

J Nat Prod. 2017 Sep 22;80(9):2524-2529. doi: 10.1021/acs.jnatprod.7b00478. Epub 2017 Aug 24.

Abstract

A new sesterterpene, sesteralterin (1), four new meroterpenes, tricycloalterfurenes A-D (2-5), and a known meroterpene, TCA-F (6), were obtained from the culture extract of an Alternaria alternata strain (k21-1) isolated from the surface of the marine red alga Lomentaria hakodatensis. The structures and relative/absolute configurations of these compounds were identified by spectroscopic analyses, mainly including 1D/2D NMR, ECD, and mass spectra and quantum chemical calculations. Compound 1 represents the first nitidasane sesterterpene naturally produced by fungi, and 2-5 feature a tetrahydrofuran unit rarely occurring in tricycloalternarenes. Compounds 1-6 were assayed for inhibition of the growth of four marine plankton and one marine alga-pathogenic bacterium.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alternaria / chemistry*
  • Furans / chemistry
  • Furans / isolation & purification*
  • Furans / pharmacology*
  • Heterocyclic Compounds, 3-Ring / chemistry
  • Heterocyclic Compounds, 3-Ring / isolation & purification*
  • Heterocyclic Compounds, 3-Ring / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Marine Biology
  • Molecular Structure
  • Terpenes / chemistry
  • Terpenes / isolation & purification*
  • Terpenes / pharmacology*

Substances

  • Furans
  • Heterocyclic Compounds, 3-Ring
  • Terpenes
  • sesteralterin
  • tricycloalterfurene B