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The Shikimic Acid Pathway pp 163–200Cite as

Hydroxybenzoic Acids and the Enigma of Gallic Acid

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Part of the book series: Recent Advances in Phytochemistry ((RAPT,volume 20))

Abstract

“Esters and/or glycosides of a variety of substituted benzoic acids are found in all higher plants.” Examining the veracity of this statement1 brings one in mind of Oscar Wilde’s aphorism concerning truth — that it is never pure and rarely simple. Certainly C6-C1 phenolic acids occur widely in plants and also microorganisms. Some plant species are particularly rich in these compounds — for example1 the leaves of winter-green (Gaultheria procumbens), extracts of which upon alkaline hydrolysis yield p-hydroxy-benzoic (2) , salicylic (4), protocatechuic (6), 2,3-dihydroxybenzoic ( 5 ), gentisic (9), vanillic ( 7 ) and syringic (8) acids (Fig. 1). Although metabolites containing these functionalities are widely distributed in angiosperms (in the botanical sense), according to the extent literature, their occurrence is nevertheless sporadic and often appears to constitute something of a taxonomic speciality. In this respect the most familiar example is probably the willow family (Salicaceae) in which derivatives of salicylic acid, such as the ω-salicylsalicin metabolites (11–13) isolated from Salix purpurea bark,2 are found. Hydroxybenzoic acids, their analogues, and significantly benzoic acid (1) itself are also consistently located esterified to both terpenoid and alkaloid structures throughout the plant kingdom. The metabolites (Fig. 2, 11–25) typically illustrate the breadth and diversity of this mode of occurrence.3–8 In view of the later biosynthetic discussions particular note should be made of the β-aminophenylalanine ester group in taxol (23).

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  1. Department of Chemistry, The University of Sheffield, Sheffield, S3 7HF, UK

    Edwin Haslam

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  1. University of California, Davis, Davis, California, USA

    Eric E. Conn

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Haslam, E. (1986). Hydroxybenzoic Acids and the Enigma of Gallic Acid. In: Conn, E.E. (eds) The Shikimic Acid Pathway. Recent Advances in Phytochemistry, vol 20. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-8056-6_7

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  • DOI: https://doi.org/10.1007/978-1-4684-8056-6_7

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