1. Biosynthesis and Metabolism of Hydroxyphenylacetic Acids in Higher Plants.
- Author
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Kindl, H.
- Subjects
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ACETIC acid , *BIOSYNTHESIS , *METABOLISM , *ASTILBE , *SAXIFRAGACEAE , *SHIKIMIC acid - Abstract
1. 2-Hydroxyphenylacetic acid, a natural phenolic product found in the genus Astilbe, derives from the shikimic acid pathway via phenylpyruvic acid. The existence of two routes for the biosynthesis of 2-hydroxyphenylacetic acid could be demonstrated: a) A direct transformation of phenylpyruvic acid into 2-hydroxyphenylacetic acid involving a migration of the side chain. More than 95% of the tritium activity of 2-hydroxyphenylacetic acid was localized in position 5 when L-[4-³H]phenylalanine was fed. This complex oxidation is analogous to the known conversion of 4-hydroxyphenylpyruvic acid to homogentisic acid. b) A hydroxylation of [4-³H]phenylacetic acid to [4-³H]2-hydroxyphenylacetic acid was observed in vivo, and was also found to take place in vitro utilizing the system peroxidase- endiol-O2. 2. 2,3-Dihydroxyphenylacetic acid and 2-hydroxy-3-methoxyphenylacetic acid could be established as natural products occurring in higher plants. Their chemical synthesis is described. By feeding experiments the following metabolic pathway is suggested: 2-hydroxyphenylacetic acid → 2,3-dihydroxyphenylacetic acid → 2-hydroxy-3-methoxyphenylacetic acid. 3,4-Dihydroxyphenylacetic acid and 3-methoxy-4-hydioxyphenylacetic acid have been detected in extracts from various species of Astilbe and identified by paper chromatography. These two acids are metabolic products of 4-hydroxyphenylacetic acid. 3. Experiments with [U-14C]shikimic acid and DL-[α-14C]phenylalanine seem to indicate that the regulation of the biosynthesis of 2-hydroxyphenylacetic acid and 4-hydroxyphenylacetic acid takes place on the level of prephemc acid. 4. Preliminary results were obtained consistent with the hypothesis that in Astilbe chinensis the 2,3-dihydroxyphenylacetic acid, 3,4-dihydroxyphenylacetic acid and 2,5-dihydroryphenyl-acetic acid are further metabolized and can be degraded by ring cleavage. [ABSTRACT FROM AUTHOR]
- Published
- 1969
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