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Biosci Biotechnol Biochem

Title:		Generation of (2-Nitroethyl)benzene and related benzenoids from L-Phenylalanine; flower scents of the Japanese Loquat Eriobotrya japonica [Rosales: Rosaceae]
Author(s):		Kuwahara Y; Asano Y;
Address:		"a Asano Active Enzyme Molecular Project, JST, ERATO , Imizu, Toyama , Japan. b Biotechnology Research Center and Department of Biotechnology , Toyama Prefectural University , Imizu, Toyama , Japan"
Journal Title:		Biosci Biotechnol Biochem
Year:		2018
Volume:		20180725
Issue:		11
Page Number:		1855 - 1866
DOI:		10.1080/09168451.2018.1498319
ISSN/ISBN:		1347-6947 (Electronic) 0916-8451 (Linking)
Abstract:		"(2-Nitroethyl)benzene, methyl 4-methoxybenzoate and 4-methoxybenzaldehyde have been known as major scent components in flowers of the Japanese loquat Eriobotrya japonica [Rosales: rosaceae], together with 13 related benzenoids, including Z- and E-2-phenylacetaldoxime and benzyl alcohol. The scents air-trapped from a flowering panicle during 24 h incubation with d(8)-L-phenylalanine were composed of 15 deuterium labeled compounds d(6)-styrene, d(5)-benzaldehyde, d(7)-2-phenylacetaldehyde, methyl d(5)-benzoate, d(7 -)2-phenylethanol, d(7)-2-phenylacetonitrile, d(4)-1,4-dimethoxybenzene, d(7)-Z-2-phenylacetaldoxime, d(4)-4-methoxybenzaldehyde, d(7)-E-2-phenylacetaldoxime, d(4)-4-methoxybenzyl alcohol, d(7)-(2-nitroethyl)benzene, methyl d(4)-4-methoxybenzoate, methyl d(6)-cinnamate and ethyl d(4)-4-methoxybenzoate. On the other hand, hexane extracts of the flower petal incubate with a mixture of d(5)-Z- and d(5)-E-2-phenylacetaldoxime after 24 h indicated generation of six d(5)-labeld components d(5)-benzaldehyde, d(5)-benzyl alcohol, d(5)-2-phenylacetaldehyde, methyl d(5)-benzoate, d(5)-2-phenylethanol, and d(5)-(2-nitroethyl)benzene. By comparing those results, (2-nitroethyl)benzene was concluded as a product directly generated from a mixture of Z- and E-2-phenylacetaldoxime together with six minor benzenoids, while two major compounds (4-methoxybenzaldehyde and methyl 4-methoxybenzoate) together with three minors from L-phenylalanine, presumably via L-tyrosine. The other two minor components were derived from L-phenylalanine"
Keywords:		Benzene Derivatives/*metabolism Eriobotrya/chemistry/*metabolism Flowers/*metabolism Gas Chromatography-Mass Spectrometry *Odorants Phenylalanine/*metabolism Plant Shoots/chemistry/metabolism Volatile Organic Compounds/chemistry/*metabolism (2-nitroethyl);
Notes:		"MedlineKuwahara, Yasumasa Asano, Yasuhisa eng England 2018/07/26 Biosci Biotechnol Biochem. 2018 Nov; 82(11):1855-1866. doi: 10.1080/09168451.2018.1498319. Epub 2018 Jul 25"