Oximes （R1R2C=NOH） are nitrogen-containing chemical constituents that are formed in species representing all kingdoms of life. In plants, oximes are positioned at important metabolic bifurcation points between gener...Oximes （R1R2C=NOH） are nitrogen-containing chemical constituents that are formed in species representing all kingdoms of life. In plants, oximes are positioned at important metabolic bifurcation points between general and specialized metabolism. The majority of plant oximes are amino acid-derived metabolites formed by the action of a cytochrome P450 from the CYP79 family. Auxin, cyanogenic glucosides, glucosinolates, and a number of other bioactive specialized metabolites including volatiles are produced from oximes. Oximes with the E configuration have high biological activity compared with Z-oximes. Oximes or their derivatives have been demonstrated or proposed to play roles in growth regulation, plant defense, pollinator attraction, and plant communication with the surrounding environment. In addition, oxime-derived products may serve as quenchers of reactive oxygen species and storage compounds for reduced nitrogen that may be released on demand by the activation of endogenous turnover pathways. As highly bioactive molecules, chemically synthesized oximes have found versatile uses in many sectors of society, especially in the agro- and medical sectors. This review provides an update on the structural diversity, occurrence, and biosynthesis of oximes in plants and discusses their role as key players in plant general and specialized metabolism.展开更多
Four cyano-containing compounds, (1E,4,5,6)-4,5,6-trihydroxy-2-cyclohexen-1-ylideneacetonitrile (1), lithospermoside (2), 4-hydroxy-2--D-glucopyranosyl oxyphenylacetonitrile (3) and 4-[-D-apiofuranosyl-(16)- O--D-gluc...Four cyano-containing compounds, (1E,4,5,6)-4,5,6-trihydroxy-2-cyclohexen-1-ylideneacetonitrile (1), lithospermoside (2), 4-hydroxy-2--D-glucopyranosyl oxyphenylacetonitrile (3) and 4-[-D-apiofuranosyl-(16)- O--D-glucopyranosyl oxy]phenylacetonitrile (4), and a nitro-containing one, 4-[-D-xylopyranosyl-(16)-O--D- glucopyranosyloxy]-1-(2-nitroethyl)benzene (5), as well as eleven other types of compounds, were isolated from the roots of Semiaquilegia adoxoides. Their structures were elucidated mainly by spectroscopic methods. Among them, 1 and 4 are new isolated compounds. The cyano- and nitro-containing compounds are very rare in plants and their isolation from one traditional Chinese medicine is really interesting.展开更多
文摘Oximes （R1R2C=NOH） are nitrogen-containing chemical constituents that are formed in species representing all kingdoms of life. In plants, oximes are positioned at important metabolic bifurcation points between general and specialized metabolism. The majority of plant oximes are amino acid-derived metabolites formed by the action of a cytochrome P450 from the CYP79 family. Auxin, cyanogenic glucosides, glucosinolates, and a number of other bioactive specialized metabolites including volatiles are produced from oximes. Oximes with the E configuration have high biological activity compared with Z-oximes. Oximes or their derivatives have been demonstrated or proposed to play roles in growth regulation, plant defense, pollinator attraction, and plant communication with the surrounding environment. In addition, oxime-derived products may serve as quenchers of reactive oxygen species and storage compounds for reduced nitrogen that may be released on demand by the activation of endogenous turnover pathways. As highly bioactive molecules, chemically synthesized oximes have found versatile uses in many sectors of society, especially in the agro- and medical sectors. This review provides an update on the structural diversity, occurrence, and biosynthesis of oximes in plants and discusses their role as key players in plant general and specialized metabolism.
基金Project supported by the National Natural Science Foundation of China (No. 30025044) and the Foundation from the Ministry of Science and Tech-nology of China (No. 2002CB512807).
文摘Four cyano-containing compounds, (1E,4,5,6)-4,5,6-trihydroxy-2-cyclohexen-1-ylideneacetonitrile (1), lithospermoside (2), 4-hydroxy-2--D-glucopyranosyl oxyphenylacetonitrile (3) and 4-[-D-apiofuranosyl-(16)- O--D-glucopyranosyl oxy]phenylacetonitrile (4), and a nitro-containing one, 4-[-D-xylopyranosyl-(16)-O--D- glucopyranosyloxy]-1-(2-nitroethyl)benzene (5), as well as eleven other types of compounds, were isolated from the roots of Semiaquilegia adoxoides. Their structures were elucidated mainly by spectroscopic methods. Among them, 1 and 4 are new isolated compounds. The cyano- and nitro-containing compounds are very rare in plants and their isolation from one traditional Chinese medicine is really interesting.
