Accumulation of feruloyltyramine and p-coumaroyltyramine in tomato leaves in response to wounding

Pearce, Gregory; Marchand, Patrice A.; Griswold, Jennifer; Lewis, Norman; Ryan, Clarence A.

doi:10.1016/s0031-9422(97)00620-1

Cited by 104 publications

(72 citation statements)

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“…Wound site-localized biosynthesis and accumulation of FT has also been observed in wounded tissue of tomato leaves (Pearce et al, 1998). Localized biosynthesis of PCAAT has been associated with the induction of THT activity that was shown to be typically restricted to the outermost cell layers of woundhealing potato tuber discs .…”

Section: Tydc As a Rate-limitingmentioning

confidence: 95%

“…The biosynthesis of PCAAT is elicited by wounding (Pearce et al, 1998;Ishihara et al, 2000) or pathogen inoculation (Keller et al, 1996;Muhlenbeck et al, 1996;Schmidt et al, 1998;Newman et al, 2001) in many species (Martin-Tanguy et al, 1996), especially in solanaceous plants (Clarke, 1982;Keller et al, 1996;Muhlenbeck et al, 1996). PCAAT can be further integrated into cell walls via a peroxidase-mediated process (Negrel and Lherminier, 1987;Keller et al, 1996) that yields monoor dicovalent ether bonds between cinnamoyl or tyramine moieties of PCAAT and the plant phenolic cell wall matrix (Lapierre et al, 1996).…”

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confidence: 99%

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Wound-Inducible Biosynthesis of Phytoalexin Hydroxycinnamic Acid Amides of Tyramine in Tryptophan and Tyrosine Decarboxylase Transgenic Tobacco Lines

Guillet

Luca

2005

Plant Physiology

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The wound-activated biosynthesis of phytoalexin hydroxycinnamic acid amides of tyramine was compared in untransformed and transgenic tobacco (Nicotiana tabacum) lines that express tryptophan decarboxylase (TDC), tyrosine decarboxylase (TYDC), or both activities. Transgenic in vitro-grown tobacco lines expressing TDC activity accumulated high levels of tryptamine but not hydroxycinnamic amides of tryptamine. In contrast, transgenic tobacco lines expressing TYDC accumulated tyramine as well as p-coumaroyltyramine and feruloyltyramine. The MeOH-soluble and cell wall fractions showed higher concentrations of wound-inducible p-coumaroyltyramine and feruloyltyramine, especially at and around wound sites, in TYDC and TDC 3 TYDC tobacco lines compared to wild-type or TDC lines. All the enzymes involved in the biosynthesis of hydroxycinnamic acid amides of tyramine were found to be similarly wound inducible in all tobacco genotypes investigated. These results provide experimental evidence that, under some circumstances, TYDC activity can exert a rate-limiting control over the carbon flux allocated to the biosynthesis of hydroxycinnamic acid amides of tyramine.The importance of tyramine during suberization of wounded potato (Solanum tuberosum) tubers is well established. Borg-Olivier and Monties (1993) used alkaline hydrolysis to fractionate and characterize the MeOH-extractable components of wound periderm in healing potato tuber discs. Fourteen days postwounding, their results established that tyramine accounts for 23% of total phenylpropanoids and Tyr-derived metabolites occurring in the MeOH-extractable free residue, whereas tyramine was undetected in the control nonwounded potato tuber discs. The presence of tyramine in suberizing potato periderm has also been corroborated by in situ noninvasive solid-state 13 C-NMR spectroscopy that allows the characterization of the polyaromatic domain of suberin in its native state within the plant cell wall matrix (Bernards et al., 1995;Bernards and Lewis, 1998).Phytoalexin hydroxycinnamic acid amides of tyramine (PCAAT), which are formed by the conjugation of tyramine with cinnamoyl-CoA thioesters (Negrel and Javelle, 1997), represent a major class of tyraminederived metabolites. The biosynthesis of PCAAT is elicited by wounding (Pearce et al., 1998;Ishihara et al., 2000) or pathogen inoculation (Keller et al., 1996;Muhlenbeck et al., 1996;Schmidt et al., 1998;Newman et al., 2001) in many species (Martin-Tanguy et al., 1996), especially in solanaceous plants (Clarke, 1982;Keller et al., 1996;Muhlenbeck et al., 1996). PCAAT can be further integrated into cell walls via a peroxidase-mediated process (Negrel and Lherminier, 1987;Keller et al., 1996) that yields monoor dicovalent ether bonds between cinnamoyl or tyramine moieties of PCAAT and the plant phenolic cell wall matrix (Lapierre et al., 1996). Although some PCAAT possess cytotoxic properties (Yamamoto et al., 1991;Park and Schoene, 2002), it is generally speculated that their major function in plants is to reinforce cell wa...

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Section: Tydc As a Rate-limitingmentioning

confidence: 95%

mentioning

confidence: 99%

Wound-Inducible Biosynthesis of Phytoalexin Hydroxycinnamic Acid Amides of Tyramine in Tryptophan and Tyrosine Decarboxylase Transgenic Tobacco Lines

Guillet

Luca

2005

Plant Physiology

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“…Our results showing that the tobacco hypersensitive-response cDNA HSR201 encodes BEBT suggest that tobacco leaves may also synthesize benzylbenzoate or a related compound under stress. Other esters that are known to be synthesized in damaged leaves include -coumaroyland feruloyltyramine in tomato (Lycopersicon esculentum; Pearce et al, 1998) and 5-caffeoylquinic (chlorogenic) acid and its derivatives in lettuce (Lactuca sativa; TomasBarberan et al, 1997). It is worth noting that RNA-blot analysis indicated that the BEBTrelated gene BEAT, which encodes an enzyme that catalyzes the formation of benzyl acetate, is not generally expressed in C. breweri leaves (Dudareva et al, 1998a) nor is it induced upon damage (N. Dudareva and E. Pichersky, unpublished data).…”

Section: Acyltransferase Activities In Wounded Leavesmentioning

confidence: 99%

Characterization of an Acyltransferase Capable of Synthesizing Benzylbenzoate and Other Volatile Esters in Flowers and Damaged Leaves of Clarkia breweri

2002

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A cDNA encoding a protein with 456 amino acids whose sequence shows considerable similarity to plant acyltransferases was identified among 750 Clarkia breweri flower expressed sequence tags. The cDNA was expressed in Escherichia coli, and the protein produced was shown to encode the enzyme benzoyl-coenzyme A (CoA):benzyl alcohol benzoyl transferase (BEBT). BEBT catalyzes the formation of benzylbenzoate, a minor constituent of the C. breweri floral aroma, but it also has activity with a number of other alcohols and acyl CoAs. The BEBTgene is expressed in different parts of the flowers with maximal RNA transcript levels in the stigma, and no expression was observed in the leaves under normal conditions. However, BEBT expression was induced in damaged leaves, reaching a maximum 6 h after damage occurred. We also show here that a closely related tobacco (Nicotiana tabacum) gene previously shown to be induced in leaves after being challenged by phytopathogenic bacteria also has BEBT activity, whereas the most similar protein to BEBT in the Arabidopsis proteome does not use benzoyl CoA as a substrate and instead can use acetyl CoA to catalyze the formation of cis-3-hexen-1-yl acetate, a green-leaf volatile.

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“…The problem is most prevalent in woody plant tissues (like cacao), as they have high levels of phenols associated with secondary thickening and lignification and, in other cases, with the production of secondary metabolites. The oxidation of phenolic compounds could be associated with factors such as wound response, sterilization process and specific components of the tissue culture media (e.g., metal cations), among others (Pearce et al, 1998;Benson, 2000;Lattanzio et al, 2006).…”

Section: Discussionmentioning

confidence: 99%

Polyphenols Distribution and Reserve Substances Analysis in Cocoa Somatic Embryogenesis

et al. 2016

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In order to understand the causes of lack of regeneration in cacao somatic embryos, two cacao varieties with different responses to regeneration potential were described based on their capacity to store different compounds. It is well known that seed reserves play a central role in the regenerative capability of somatic embryos; thus, we followed histochemical changes and reserve fluctuations of proteins, polysaccharides and polyphenols during somatic embryogenesis (SE) in the two cacao varieties. The study showed that, in somatic embryos of the regenerating variety, polyphenols were localized mainly in the periphery of the embryo (epidermal cells) and proteins were the main storage substance in the embryo expression medium, while the non-regenerating variety had a high presence of polysaccharides with random distribution of polyphenols at the end of the embryo induction step.Keywords: antioxidants, histology, reserve accumulation, recalcitrance, somatic embryogenesis. RESUMENDos variedades de cacao con diferentes respuestas a la regeneración fueron descritas en función de su capacidad para almacenar diferentes compuestos, con el fin de aproximarse al entendimiento de las causas de la falta de regeneración en embriones somáticos de cacao. Es bien sabido que las reservas de semillas desempeñan un papel central en la capacidad de regeneración de embriones somáticos; por tanto, se realizó un seguimiento de cambios histoquímicos y fluctuaciones de reserva de proteínas, polisacáridos y polifenoles durante la embriogénesis somática (SE) en dos variedades de cacao. El estudio mostró que, en los embriones somáticos de la variedad regenerante, los polifenoles se localizaron principalmente en la periferia del embrión (células de la epidermis) y las proteínas fueron el componente principal de almacenamiento en el medio de expresión de embriones, mientras que la variedad no regenerante tenía una alta presencia de polisacáridos y una distribución aleatoria de los polifenoles en el final de la etapa de inducción de embriones. Palabras clave: acumulación de reservas, antioxidantes, embriogénesis somática, histología, recalcitrancia.

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Accumulation of feruloyltyramine and p-coumaroyltyramine in tomato leaves in response to wounding

Cited by 104 publications

References 25 publications

Wound-Inducible Biosynthesis of Phytoalexin Hydroxycinnamic Acid Amides of Tyramine in Tryptophan and Tyrosine Decarboxylase Transgenic Tobacco Lines

Wound-Inducible Biosynthesis of Phytoalexin Hydroxycinnamic Acid Amides of Tyramine in Tryptophan and Tyrosine Decarboxylase Transgenic Tobacco Lines

Characterization of an Acyltransferase Capable of Synthesizing Benzylbenzoate and Other Volatile Esters in Flowers and Damaged Leaves of Clarkia breweri

Polyphenols Distribution and Reserve Substances Analysis in Cocoa Somatic Embryogenesis

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