(2-Nitroethyl)benzene: a major flower scent from the Japanese loquat Eriobotrya japonica [Rosales: Rosaceae]

Abstract

(2-Nitroethyl)benzene was identified as a major component of the flower scent of the Japanese loquat Eriobotrya japonica [Rosales: Rosaceae], together with p-methoxybenzaldehyde and methyl p-methoxybenzoate. The corresponding volatiles from chopped leaves did not contain these three compounds. This is the first time that 1-nitro-2-phenyl-ethane has been demonstrated to be a natural product among Japanese plants, although two Japanese millipedes are known to possess the same aromatics.

Generation of (2-Nitroethyl)benzene and related benzenoids from L-Phenylalanine; flower scents of the Japanese Loquat Eriobotrya japonica [Rosales: Rosaceae]

“…In the recent biosynthetic study of the flower volatiles from the Japanese loquat Eriobotrya japonica, however, the presence of 13 has been lost [12] together with seven benzenoids (1, 5, 7, 8, 11, 15 and 16), with unknown reason. On the other hand, zingerone and phenethyl benzoate have not been detected in our results [1].…”

“…The adsorbed flower volatiles, after eluted with hexane, were analyzed by a gas chromatography coupled with a mass spectrometry (GC/ MS) analysis. The following 15 aromatic compounds (benzenoids) have been recovered; styrene (1), benzaldehyde (2), 2-phenylacetaldehyde (4), methyl benzoate (5), 2-phenylethanol (6), 2-phenylacetonitrile (7), 1,4dimethoxybenzene (8), (Z)-2-phenylacetaldoxime (9), 4-methoxybenzaldehyde (10), (E)-2-phenylacetaldoxime (11), 4-methoxybenzyl alcohol (12), (2-nitroethyl)benzene (13), methyl 4-methoxybenzoate (14), methyl cinnamate (15) and ethyl 4-methoxybenzoate (16), along with five terpenoids, as reported [1]. Among them, (2nitroethyl)benzene (13,32.7%), 4-methoxybenzaldehyde (10,27.3%) and methyl 4-methoxybenzoate (14, 24.6%) has been the major components.…”

“…Among them, (2nitroethyl)benzene (13,32.7%), 4-methoxybenzaldehyde (10,27.3%) and methyl 4-methoxybenzoate (14, 24.6%) has been the major components. Presence of 13 as a flower scent is the first finding in Japanese plants [1], while 13 has been known as the essential oil component from Brazilian and African plants [2][3][4]. Natural distribution of NO 2 -containing molecule seems to be not common, but it has actually been distributed widely as a minor component in many flower scents from orchids and others [5][6][7][8][9].…”

Aromatic amino acid decarboxylase is involved in volatile phenylacetaldehyde production in loquat (<i>Eriobotrya japonica</i>) flowers

“…It has been reported that loquat flowers produce volatile benzenoids, including phenylacetaldehyde, phenethyl alcohol, and 2-phenethyl benzoate (Koeduka et al 2016b), whereas loquat leaf volatiles are mostly composed of C6 compounds such as (Z)-3-hexenyl acetate and (Z)-3-hexenyl butanoate (Kuwahara et al 2014). The levels of the EjAADC1 transcript were higher in loquat flowers than in leaves and increased throughout flower development.…”

“…We previously reported that phenylacetaldehyde, phenylethyl alcohol, and 2-phenethyl benzoate are characteristic scent components of loquat (Eriobotrya japonica) flowers (Koeduka et al 2016a(Koeduka et al , 2016bKuwahara et al 2014). However, the gene responsible for biosynthesis of volatile phenylacetaldehyde in loquat has not been identified to date.…”