Varioxepine a, a 3H-oxepine-containing alkaloid with a new oxa-cage from the marine algal-derived endophytic fungus Paecilomyces variotii

Peng Zhang, Attila Mandi, Xiao Ming Li, Feng Yu Du, Jia Ning Wang, Xin Li, T. Kurtán, Bin Gui Wang

Research output: Contribution to journalArticle

53 Citations (Scopus)

Abstract

A new 3H-oxepine-containing alkaloid, varioxepine A (1), characterized by a structurally unprecedented condensed 3, 6, 8-trioxabicyclo[3.2.1]octane motif, was isolated from the marine algal-derived endophytic fungus Paecilomyces variotii. Due to the low proton/carbon ratio, the unambiguous assignment of the planar structure and relative configuration was precluded by NMR experiments and solved by single crystal X-ray analysis. The absolute configuration was established by DFT conformational analysis and TDDFT-ECD calculations. Compound 1 inhibited plant pathogenic fungus Fusarium graminearum.

Original languageEnglish
Pages (from-to)4834-4837
Number of pages4
JournalOrganic Letters
Volume16
Issue number18
DOIs
Publication statusPublished - Sep 19 2014

Fingerprint

Oxepins
Paecilomyces
alkaloids
fungi
Fungi
Alkaloids
planar structures
X ray analysis
Fusarium
octanes
configurations
Discrete Fourier transforms
Protons
Carbon
Nuclear magnetic resonance
X-Rays
Single crystals
nuclear magnetic resonance
protons
carbon

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Varioxepine a, a 3H-oxepine-containing alkaloid with a new oxa-cage from the marine algal-derived endophytic fungus Paecilomyces variotii. / Zhang, Peng; Mandi, Attila; Li, Xiao Ming; Du, Feng Yu; Wang, Jia Ning; Li, Xin; Kurtán, T.; Wang, Bin Gui.

In: Organic Letters, Vol. 16, No. 18, 19.09.2014, p. 4834-4837.

Research output: Contribution to journalArticle

Zhang, Peng ; Mandi, Attila ; Li, Xiao Ming ; Du, Feng Yu ; Wang, Jia Ning ; Li, Xin ; Kurtán, T. ; Wang, Bin Gui. / Varioxepine a, a 3H-oxepine-containing alkaloid with a new oxa-cage from the marine algal-derived endophytic fungus Paecilomyces variotii. In: Organic Letters. 2014 ; Vol. 16, No. 18. pp. 4834-4837.
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