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New Dimeric Compounds of Avenanthramide Phytoalexin in Oats

New Dimeric Compounds of Avenanthramide Phytoalexin in Oats

Yozo Okazaki, Akihiro Ishizuka, Atsushi Ishihara, Takaaki Nishioka, Hajime Iwamura

J Org Chem. 2007 May 11;72(10):3830-9.

PMID: 17432911

Abstract:

Avenanthramide B is an oat phytoalexin produced in response to pathogen attack and elicitation. We found the formation of new dimers (1-5) of avenanthramide B in elicited oat leaves. The dimers were synthesized by a reaction of peroxidase and avenanthramide B in the presence of hydrogen peroxide. The structures of 1-5 were determined by spectroscopic analyses, chemical derivatization, and 15N labeling. Compound 1 was a dehydrodimer of avenanthramide B with a bisbutane lactam skeleton, while 2-4 were monohydrated dehydrodimers with butane lactam structures. Compound 5 was also a monohydrated dehydrodimer but with a tetrahydrofuran structure. All the compounds were classified into lignanamides that were formed by an 8'-8' coupling reaction between two avenanthramide B units.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
CS38392	Avenanthramide B			Price

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