Structures and biosynthesis of aflastatins: Novel inhibitors of aflatoxin production by Aspergillus parasiticus

Makoto Ono, Shohei Sakuda, Hiroyuki Ikeda, Kazuo Furihata, Jiro Nakayama, Akinori Suzuki, Akira Isogai

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Two novel inhibitors of aflatoxin production by Aspergillus parasiticus were isolated from the mycelial extracts of Streptomyces sp. MRI142 and termed aflastatin A and B. The structures of aflastatin A (1) and B (5) were elucidated by NMR and chemical degradation experiments. These compounds have a novel skeleton of a tetramic acid derivative with a highly oxygenated long alkyl chain. The incorporation experiments using 13C-labeled acetates, propionate, glucose and glycolate suggested that most of the C2 and C3 units involved in the alkyl chain moiety of aflastatin A were biosynthesized from acetic and propionic acids, but five C2 units in the alkyl chain originated from glycolic acid.

Original languageEnglish
Pages (from-to)1019-1028
Number of pages10
JournalJournal of Antibiotics
Volume51
Issue number11
DOIs
Publication statusPublished - Jan 1 1998
Externally publishedYes

Fingerprint

glycolic acid
Aflatoxins
Aspergillus
Propionates
Streptomyces
Skeleton
Acetic Acid
Acetates
Glucose
aflastatin A
aflastatin B

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Drug Discovery

Cite this

Structures and biosynthesis of aflastatins : Novel inhibitors of aflatoxin production by Aspergillus parasiticus. / Ono, Makoto; Sakuda, Shohei; Ikeda, Hiroyuki; Furihata, Kazuo; Nakayama, Jiro; Suzuki, Akinori; Isogai, Akira.

In: Journal of Antibiotics, Vol. 51, No. 11, 01.01.1998, p. 1019-1028.

Research output: Contribution to journalArticle

Ono, Makoto ; Sakuda, Shohei ; Ikeda, Hiroyuki ; Furihata, Kazuo ; Nakayama, Jiro ; Suzuki, Akinori ; Isogai, Akira. / Structures and biosynthesis of aflastatins : Novel inhibitors of aflatoxin production by Aspergillus parasiticus. In: Journal of Antibiotics. 1998 ; Vol. 51, No. 11. pp. 1019-1028.
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