Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field

Sangkeun Son, Sung Kyun Ko, Jong Won Kim, Jae Kyoung Lee, Mina Jang, In Ja Ryoo, Gwi Ja Hwang, Min Cheol Kwon, Kee Sun Shin, Yushi Futamura, Young Soo Hong, Hyuncheol Oh, Bo Yeon Kim, Masashi Ueki, Shunji Takahashi, Hiroyuki Osada, Jae Hyuk Jang, Jong Seog Ahn*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

Twelve metabolites, including five highly oxygenated azaphilones, geumsanols A-E, along with seven known analogues were isolated from Penicillium sp. KCB11A109, a fungus derived from a ginseng field. Their structures were assigned by spectroscopic means (NMR and MS), and stereochemistries were determined by extensive spectroscopic analyses (1H-1H coupling constants, NOESY, and HETLOC) and chemical derivatizations (modified Mosher's method and acetonide formation). The isolates were evaluated for their anticancer, antimicrobial, antimalarial activities, and phenotypic effects in zebrafish development. Of these compounds possessing no pyranoquinone core, only geumsanol E exhibited cytotoxic activities and toxic effects on zebrafish embryos, suggesting that a double bond at C-11 and C-12 is important for biological activity.

Original languageEnglish
Pages (from-to)154-164
Number of pages11
JournalPhytochemistry
Volume122
DOIs
Publication statusPublished - 2016 Feb 1
Externally publishedYes

Keywords

  • Azaphilone
  • Geumsanol
  • Penicillium sp.
  • Structure elucidation
  • Trichocomaceae
  • Zebrafish screening

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

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