Two ambuic acid dimers derived from homo- endo Diels-Alder reaction from Pestalotiopsis versicolor

J Asian Nat Prod Res. 2023 Jul-Aug;25(7):641-649. doi: 10.1080/10286020.2022.2132480. Epub 2022 Oct 20.

Abstract

Two new dimers of ambuic acid, pestaloversicoloric acids A (1) and B (2), and a known derivative, 13(S)-hydroxyambuic acid (3), were isolated from the static fermentation product of Pestalotiopsis versicolor. The structural identification was accomplished via analyses on the data of HR-MS, 1 D and 2 D NMR, and ECD. Different from the well-known exo-type dimer, torreyanic acid, compounds 1 and 2 represent the first example of endo-type product derived from the intermolecular Diels-Alder reaction of two molecules of ambuic acid derivative with the identical absolute stereochemistry.

Keywords: Ambuic acid; Diels-Alder reaction; Pestalotiopsis versicolor; endo-product.

MeSH terms

  • Cycloaddition Reaction
  • Cyclohexanones* / chemistry
  • Molecular Structure

Substances

  • ambuic acid
  • Cyclohexanones

Supplementary concepts

  • Pestalotiopsis versicolor