Peniciadametizine A, a dithiodiketopiperazine with a unique spiro[furan-2,7′-pyrazino[1,2-b][1,2]oxazine] skeleton, and a related analogue, peniciadametizine B, from the marine sponge-derived fungus Penicillium adametzioides

Yang Liu, Attila Mándi, Xiao Ming Li, Ling Hong Meng, Tibor Kurtán, Bin Gui Wang

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Peniciadametizine A (1); a new dithiodiketopiperazine derivative possessing a unique spiro[furan-2,7′-pyrazino[1,2-b][1,2]oxazine] skeleton, together with a highly oxygenated new analogue, peniciadametizine B (2); as well as two known compounds, brasiliamide A (3); and viridicatumtoxin (4), were isolated and identified from Penicillium adametzioides AS-53, a fungus obtained from an unidentified marine sponge. The unambiguous assignment of the relative and absolute configuration for the spiro center C-2 of compound 1 was solved by the combination of NMR and ECD measurements with Density-Functional Theory (DFT) conformational analysis and Time-Dependent Density-Functional Theory-Electronic Circular Dichroism (TDDFT-ECD) calculations. The spiro[furan-2,7′-pyrazino[1,2-b][1,2]oxazine] skeleton of 1 has not been reported yet among natural products and the biosynthetic pathway for 1 and 2 was discussed. Compounds 1 and 2 showed inhibitory activity against the pathogenic fungus Alternaria brassicae.

Original languageEnglish
Pages (from-to)3640-3652
Number of pages13
JournalMarine Drugs
Volume13
Issue number6
DOIs
Publication statusPublished - Jun 1 2015

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Keywords

  • Antifungal activity
  • Endophytic fungus
  • Marine sponge
  • Penicillium adametzioides
  • Secondary metabolites

ASJC Scopus subject areas

  • Drug Discovery

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