B-norsteroids From Hymenoscyphus Pseudoalbidus

Molecules. 2012 Jun 25;17(7):7769-81. doi: 10.3390/molecules17077769.

Abstract

Two viridin-related B-norsteroids, B-norviridiol lactone (1) and B-norviridin enol (2), both possessing distinct unprecedented carbon skeletons, were isolated from a liquid culture of the ash dieback-causing fungus Hymenoscyphus pseudoalbidus. Compound 2 was found to degrade to a third B-norsteroidal compound, 1β-hydroxy-2α-hydro-asterogynin A (3), which was later detected in the original culture. The proposed structure of 1 is, regarding connectivity, identical to the original erroneous structure for TAEMC161, which was later reassigned as viridiol. Compound 2 showed an unprecedented ¹H-¹³C HMBC correlation through an intramolecular hydrogen bond. The five-membered B-ring of compounds 1-3 was proposed to be formed by a benzilic acid rearrangement. The known compound asterogynin A was found to be formed from 3 by a β-elimination of water. All compounds were characterized by NMR spectroscopy, LC-HRMS and polarimetry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Androstenediols / chemistry
  • Ascomycota / chemistry*
  • Magnetic Resonance Spectroscopy
  • Norsteroids / chemistry
  • Norsteroids / isolation & purification*
  • Sterols / chemistry

Substances

  • Androstenediols
  • Norsteroids
  • Sterols
  • asterogynin A
  • viridiol