Chlorinated Dehydrocurvularins and Alterperylenepoxide A from Alternaria sp. AST0039, a Fungal Endophyte of Astragalus lentiginosus

Bharat P. Bashyal, E. M Kithsiri Wijeratne, Joseph Tillotson, A. Elizabeth Arnold, Eli Chapman, A. A Leslie Gunatilaka

Research output: Research - peer-reviewArticle

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Abstract

Investigation of Alternaria sp. AST0039, an endophytic fungus obtained from the leaf tissue of Astragalus lentiginosus, led to the isolation of (−)-(10E,15S)-4,6-dichloro-10(11)-dehydrocurvularin (1), (−)-(10E,15S)-6-chloro-10(11)-dehydrocurvularin (2), (−)-(10E,15S)-10(11)-dehydrocurvularin (3), and alterperylenepoxide A (4) together with scytalone and α-acetylorcinol. Structures of 1 and 4 were established from their spectroscopic data, and the relative configuration of 4 was determined with the help of nuclear Overhauser effect difference data. All metabolites were evaluated for their cytotoxic activity and ability to induce heat-shock and unfolded protein responses. Compounds 2 and 3 exhibited cytotoxicity to all five cancer cell lines tested and increased the level of the pro-apoptotic transcription factor CHOP, but only 3 induced the heat-shock response and caused a strong unfolded protein response.

LanguageEnglish (US)
Pages427-433
Number of pages7
JournalJournal of Natural Products
Volume80
Issue number2
DOIs
StatePublished - Feb 24 2017

Fingerprint

Endophytes
Alternaria
dehydrocurvularin
curvularin
Unfolded Protein Response
Proteins
Hot Temperature
Transcription Factor CHOP
Heat-Shock Response
Heat-Shock Proteins
Fungi
Cell Line
Neoplasms
scytolone
Cytotoxicity
Metabolites
Cells
Tissue

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

Chlorinated Dehydrocurvularins and Alterperylenepoxide A from Alternaria sp. AST0039, a Fungal Endophyte of Astragalus lentiginosus. / Bashyal, Bharat P.; Wijeratne, E. M Kithsiri; Tillotson, Joseph; Arnold, A. Elizabeth; Chapman, Eli; Gunatilaka, A. A Leslie.

In: Journal of Natural Products, Vol. 80, No. 2, 24.02.2017, p. 427-433.

Research output: Research - peer-reviewArticle

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