Direct NMR evidence for the equivalent participation ofL-phenylalanine andL-tyrosine in the biosynthesis of the intermolecular Diels–Alder type adducts of prenylchalcone and prenylated 2-arylbenzofuran inMorusalbacell cultures
作者:
Yoshio Hano,
Taro Nomura,
Shinichi Ueda,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1994)
卷期:
Volume 72,
issue 1
页码: 12-14
ISSN:0008-4042
年代: 1994
DOI:10.1139/v94-003
出版商: NRC Research Press
数据来源: NRC
摘要:
L-[3-13C]Phenylalanine andL-[3-13C]tyrosine were administered toMorusalbacell cultures, to produce intermolecular Diels–Alder type adducts of a prenylchalcone and a 2-arylbenzofuran such as chalcomoracin (1) as well as the adducts of two molecules of prenylchalcones such as kuwanon J (2) in high yields. The13C NMR spectra of1and2isolated from the cultures revealed that both amino acids were incorporated intact into chalcomoracin (1) and kuwanon J (2). This is the first example of direct NMR evidence for the almost equivalent incorporation of phenylalanine and tyrosine into the shikimate metabolites. This finding suggests the participation of a biosynthetic route from phenylalanine viatrans-cinnamate top-coumarate and from tyrosine top-coumarate in this plant.
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