Evidence from stable-isotope labeling that catechol is an intermediate in salicylic acid catabolism in the flowers of Silene latifolia (white campion)

Abstract

Main conclusion A stable isotope-assisted mass spectrometry-based platform was utilized to demonstrate that the plant hormone, salicylic acid, is catabolized to catechol, a widespread secondary plant compound.

Chemistry, biosynthesis and biology of floral volatiles: roles in pollination and other functions

“…21). 86,87 The activities of the two O -methylation steps have been demonstrated, 86,87 and one of the genes identified. 86,88…”

“…19). 80 Since this original report, genes participating in other steps in phenylpropene formation have been identied, such as in Omethylation of caffeoyl-CoA to feruloyl-CoA in petunia, 81 the acetylation of coniferyl alcohol in Prunus mume, 82 and the conversion of coniferyl acetate to eugenol (87) in roses. 83 The formation of benzenoid volatiles requires the shortening of the C 3 side chain of their phenylpropanoid precursors.…”

“…253,254 Finally, Agrius convolvuli responded to various compounds of its Gladiolus longicollis host plant, among them aromatic compounds [e.g. benzaldehyde (88), benzyl acetate ( 90) phenylacetaldehyde (83), eugenol (87)] and nitrogen-bearing compounds [3-methylbutylaldoxime (114), 2-phenylacetonitrile (92), 2-phenylnitroethane ( 93)]. 255 6.2.2 Settling moths.…”

“…Feeding of potential precursors established that this benzenoid is derived from phenylalanine via ( E )-cinnamic acid, benzoic acid and salicylic acid. 86 Decarboxylation results in catechol, 87 which is then O -methylated sequentially to give 1,2-dimethoxybenzene (Fig. 21).…”

“…Compounds eliciting antennal responses were 2-aminobenzaldehyde (166), benzaldehyde(88), decanal(115) and nonanal(126) in Chinese cabbage (Brassica rapa breeds), nonanal(126), methyl salicylate(125), and phenylacetaldehyde(83) in carrot (Daucus carota sativus), and nonanal (126), 169, 83 and 2-phenylethanol (84) in radish (Raphanus raphanistrum sativus) 310. In apple (Malus domestica), antennal responses were elicited by 88, benzyl alcohol (99) (dominated the scent bouquet), (E)-cinnamyl alcohol(154), eugenol(87), methyleugenol(175), and two unknown compounds(Rachersberger et al 2019). 311 About 20 compounds in the ower scent of pear (Pyrus communis) elicited antennal responses in honeybees, among them common [e.g., (E)-b-ocimene (62), 4-oxoisophorone (169)], but also rare [Nisobutylformamide (199), (E)-N-(3-methylbutyl)-1phenylmethanimine (200)] oral scents and even compounds newly identied from nature [(E)-N-(2-methylbutyl)-and (E)-N-(3-methylbutyl)-1-(pyridin-3-yl)methanimine (46 and 47)].…”