Conversion in Plants of Benzoic Acid to Salicylic Acid and its βd-Glucoside

Klämbt, Hans-Dieter

doi:10.1038/196491a0

Cited by 67 publications

(39 citation statements)

References 8 publications

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“…4A). Similarly, if SA is derived from BA, as some reports have indicated (Klämbt, 1962;León et al, 1993;Yalpani et al, 1993;Meuwly et al, 1995;Silverman et al, 1995;Coquoz et al, 1998;Ribnicky et al, 1998), an increase in the percentage of labeled volatile molecules would be expected in similar experiments involving SA-d6 feeding in the presence versus absence of AIP. Indeed, while SA-d6 feeding alone resulted in 50%, 60%, and 80% of guaiacol, veratrole, and MeSA molecules showing the 4-D mass shift, respectively, in the presence of AIP, the label was incorporated into more than 90% of these volatile compounds (Fig.…”

Section: Evidence That Veratrole Is Derived From the Phenylpropanoid mentioning

confidence: 99%

“…8). While long suspected (Klämbt, 1962;Yalpani et al, 1993;Meuwly et al, 1995;Silverman et al, 1995;Coquoz et al, 1998;Ribnicky et al, 1998), it has recently been convincingly demonstrated in petunia (Petunia hybrida) and Arabidopsis (Arabidopsis thaliana) that BA is made by b-oxidation of Cin (Van Moerkercke et al, 2009;Colquhoun et al, 2012;Klempien et al, 2012, Lee et al, 2012Qualley et al, 2012). The synthesis of SA is not as clearly resolved.…”

Section: Veratrole Emission During the Day/night Cyclementioning

confidence: 99%

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Veratrole Biosynthesis in White Campion

Akhtar

Pichersky

2013

Plant Physiology

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White campion (Silene latifolia) is a dioecious plant that emits 1,2-dimethoxybenzene (veratrole), a potent pollinator attractant to the nocturnal moth Hadena bicruris. Little is known about veratrole biosynthesis, although methylation of 2-methoxyphenol (guaiacol), another volatile emitted from white campion flowers, has been proposed. Here, we explore the biosynthetic route to veratrole. Feeding white campion flowers with [ 13 C 9 ]L-phenylalanine increased guaiacol and veratrole emission, and a significant portion of these volatile molecules contained the stable isotope. When white campion flowers were treated with the phenylalanine ammonia lyase inhibitor 2-aminoindan-2-phosphonic acid, guaiacol and veratrole levels were reduced by 50% and 63%, respectively. Feeding with benzoic acid (BA) or salicylic acid (SA) increased veratrole emission 2-fold, while [ 2 H 5 ]BA and [ 2 H 6 ]SA feeding indicated that the benzene ring of both guaiacol and veratrole is derived from BA via SA. We further report guaiacol O-methyltransferase (GOMT) activity in the flowers of white campion. The enzyme was purified to apparent homogeneity, and the peptide sequence matched that encoded by a recently identified complementary DNA (SlGOMT1) from a white campion flower expressed sequence tag database. Screening of a small population of North American white campion plants for floral volatile emission revealed that not all plants emitted veratrole or possessed GOMT activity, and SlGOMT1 expression was only observed in veratrole emitters. Collectively these data suggest that veratrole is derived by the methylation of guaiacol, which itself originates from phenylalanine via BA and SA, and therefore implies a novel branch point of the general phenylpropanoid pathway.

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Section: Evidence That Veratrole Is Derived From the Phenylpropanoid mentioning

confidence: 99%

Section: Veratrole Emission During the Day/night Cyclementioning

confidence: 99%

Veratrole Biosynthesis in White Campion

Akhtar

Pichersky

2013

Plant Physiology

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“…Early feeding studies with radio-labelled Phe, t-CA, or benzoic acid (BA) suggested that SA is synthesized from Phe via t-CA, which is then converted to SA via two possible intermediates: ortho-coumaric acid (Route 2a) or BA (Routes 2b&c), depending on the plant species (Klämbt, 1962;El-Basyouni et al, 1964;Chadha and Brown, 1974). In the 1990s, the discovery that SA plays a critical role in signaling defense responses and thermogenesis brought renewed interest in elucidating the SA biosynthetic pathway (Malamy and Klessig, 1992;Raskin, 1992;Dempsey et al, 1999).…”

Section: The Pal Pathway To Samentioning

confidence: 99%

Salicylic Acid Biosynthesis and Metabolism

Dempsey

Vlot

Wildermuth

et al. 2011

The Arabidopsis Book

617

549

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Salicylic acid (SA) has been shown to regulate various aspects of growth and development; it also serves as a critical signal for activating disease resistance in Arabidopsis thaliana and other plant species. This review surveys the mechanisms involved in the biosynthesis and metabolism of this critical plant hormone. While a complete biosynthetic route has yet to be established, stressed Arabidopsis appear to synthesize SA primarily via an isochorismate-utilizing pathway in the chloroplast. A distinct pathway utilizing phenylalanine as the substrate also may contribute to SA accumulation, although to a much lesser extent. Once synthesized, free SA levels can be regulated by a variety of chemical modifications. Many of these modifications inactivate SA; however, some confer novel properties that may aid in long distance SA transport or the activation of stress responses complementary to those induced by free SA. In addition, a number of factors that directly or indirectly regulate the expression of SA biosynthetic genes or that influence the rate of SA catabolism have been identified. An integrated model, encompassing current knowledge of SA metabolism in Arabidopsis, as well as the influence other plant hormones exert on SA metabolism, is presented.

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“…In leaf segments of Pvimula acaulis and Gaultheria procumbens (Chadha and Brown, 1974), and in tomato seedlings infected with Agrobacterium (El-Basyouni et al, 1964) (Zenk and Miiller, 1964), in Gaulthevia pvocumbens tissue (Ellis and Amrhein, 1971), and in uninfected tomato seedlings (Chadha and Brown, 1974). In addition, the direct conversion of [14C]BA to ['4C]SA has been reported in etiolated hypocotyls of Helianthus annuus, in Solanum tuberosum tubers, in Pisum sativum internodes (Klambt, 1962), and in rice (Silverman et al, 1995). Recently, cell cultures of tobacco have been shown to incorporate both [I4C]CA and [I4C1BA into [I4C1SA (Yalpani et al, 1993).…”

mentioning

confidence: 99%