Identification of Chlorogenic Acid as a Resistance Factor for Thrips in Chrysanthemum

Leiss, Kirsten A.; Maltese, Federica; Choi, Young Hae; Verpoorte, Robert; Klinkhamer, Peter G. L.

doi:10.1104/pp.109.138131

Cited by 260 publications

(237 citation statements)

References 61 publications

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“…Given a continuous supply with chlorogenate and glucarate, the presence of the SlCGT in the apoplastic space of leaves should lead to the extracellular accumulation of caffeoylglucarate. Whether caffeoylglucarate alone or in combination with chlorogenate acts as the bioactive agent in defense reactions against herbivores (5,54,55), bacteria and fungi (56 -58), or against viruses (59) remains elusive. Biological activity of these caffeate esters has been related to their assumed prooxidant effects through quinone formation.…”

Section: Discussionmentioning

confidence: 99%

Identification and Localization of a Lipase-like Acyltransferase in Phenylpropanoid Metabolism of Tomato (Solanum lycopersicum)

Teutschbein

Gross

Nimtz

et al. 2010

Journal of Biological Chemistry

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We have isolated an enzyme classified as chlorogenate: glucarate caffeoyltransferase (CGT) from seedlings of tomato (Solanum lycopersicum) that catalyzes the formation of caffeoylglucarate and caffeoylgalactarate using chlorogenate (5-O-caffeoylquinate) as acyl donor. Peptide sequences obtained by trypsin digestion and spectrometric sequencing were used to isolate the SlCGT cDNA encoding a protein of 380 amino acids with a putative targeting signal of 24 amino acids indicating an entry of the SlCGT into the secretory pathway. Immunogold electron microscopy revealed the localization of the enzyme in the apoplastic space of tomato leaves. Southern blot analysis of genomic cDNA suggests that SlCGT is encoded by a single-copy gene. The SlCGT cDNA was functionally expressed in Nicotiana benthamiana leaves and proved to confer chlorogenate-dependent caffeoyltransferase activity in the presence of glucarate. Sequence comparison of the deduced amino acid sequence identified the protein unexpectedly as a GDSL lipase-like protein, representing a new member of the SGNH protein superfamily. Lipases of this family employ a catalytic triad of Ser-Asp-His with Ser as nucleophile of the GDSL motif. Site-directed mutagenesis of each residue of the assumed respective SlCGT catalytic triad, however, indicated that the catalytic triad of the GDSL lipase is not essential for SlCGT enzymatic activity. SlCGT is therefore the first example of a GDSL lipase-like protein that lost hydrolytic activity and has acquired a completely new function in plant metabolism, functioning in secondary metabolism as acyltransferase in synthesis of hydroxycinnamate esters by employing amino acid residues different from the lipase catalytic triad.Plant metabolism is characterized by the formation of a vast number of secondary compounds, brought about by gene families coding for enzymes that modify various phenolic, terpenoid, alkaloid, or polyketide skeletons by oxidation and reduction as well as by methylation, glycosylation, prenylation, and acylation. Most of the phenolic structures in plants are synthesized via the shikimate/hydroxycinnamate pathway, which feeds into different types of hydroxycinnamate (HCA) 4 sidechain reactions (1). Among them are extensions with formation of additional ring systems (e.g. flavonoids or stilbenes), degradation (e.g. hydroxybenzoates), reduction (e.g. hydroxycinnamyl alcohols feeding into lignin biosynthesis), oxidation and lactonization (e.g. coumarins), and conjugation with a wide range of different primary and secondary compounds to form esters or amides. Syntheses of HCA conjugates are catalyzed by hydroxycinnamoyltransferases that play a decisive role in catalyzing the formation of complex patterns of HCA esters (2). Such a pattern, for example, was recently identified from Brassica napus seeds and exhibited a mixture of sinapate esters containing choline, malate, mono-and disaccharides, as well as flavonoid glycosides and an unusual cyclic spermidine amide (3).Tomato (Solanum lycopersicum) leaves accumulate caf...

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Section: Discussionmentioning

confidence: 99%

Identification and Localization of a Lipase-like Acyltransferase in Phenylpropanoid Metabolism of Tomato (Solanum lycopersicum)

Teutschbein

Gross

Nimtz

et al. 2010

Journal of Biological Chemistry

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“…Spodoptera frugiperda versus Manduca sexta oral secretions), which may influence the level of polyphenol oxidase (PPO) induction in the treated leaves, as chlorogenic acid is the preferred substrate of this enzyme (Li and Steffens, 2002; but see Keinänen et al, 2001). Chlorogenic acid and feruloyl quinic acid can be important resistance factors against thrips (Leiss et al, 2009). In our experiments, chlorogenic acid was induced by UV-B both in wild-type and as-lox lines (Fig.…”

Section: Flavonoids and Chlorogenic Acidmentioning

confidence: 99%

Jasmonate-Dependent and -Independent Pathways Mediate Specific Effects of Solar Ultraviolet B Radiation on Leaf Phenolics and Antiherbivore Defense

et al. 2009

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Ultraviolet B (UV-B) radiation, a very small fraction of the daylight spectrum, elicits changes in plant secondary metabolism that have large effects on plant-insect interactions. The signal transduction pathways that mediate these specific effects of solar UV-B are not known. We examined the role of jasmonate signaling by measuring responses to UV-B in wild-type and transgenic jasmonate-deficient Nicotiana attenuata plants in which a lipoxygenase gene (NaLOX3) was silenced (as-lox). In wildtype plants, UV-B failed to elicit the accumulation of jasmonic acid (JA) or the bioactive JA-isoleucine conjugate but amplified the response of jasmonate-inducible genes, such as trypsin proteinase inhibitor (TPI), to wounding and methyl jasmonate, and increased the accumulation of several phenylpropanoid derivatives. Some of these phenolic responses (accumulation of caffeoyl-polyamine conjugates) were completely lacking in as-lox plants, whereas others (accumulation of rutin and chlorogenic acid) were similar in both genotypes. In open field conditions, as-lox plants received more insect damage than wild-type plants, as expected, but the dramatic increase in resistance to herbivory elicited by UV-B exposure, which was highly significant in wild-type plants, did not occur in as-lox plants. We conclude that solar UV-B (1) uses jasmonate-dependent and -independent pathways in the elicitation of phenolic compounds, and (2) increases sensitivity to jasmonates, leading to enhanced expression of wound-response genes (TPI). The lack of UV-B-induced antiherbivore protection in as-lox plants suggests that jasmonate signaling plays a central role in the mechanisms by which solar UV-B increases resistance to insect herbivores in the field.Peak fluence rates of solar UV-B radiation at mid latitudes rarely exceed 2 mmol m 22 s 21 , which represents less than 0.5% of the total quantum flux density between 285 and 700 nm. This small fraction of solar radiation has multiple effects on plants, but none of these effects, except direct DNA damage by UV-B quanta (Britt, 2004

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“…The assignments of NMR signals were made based on the previous reports (Choi et al 2006;Leiss et al 2009) and the database of metabolites spectra from the Natural Products Laboratory, Leiden University, The Netherlands. In principal, a 1 H-NMR spectrum is divided into three regions, i.e.…”

Section: Metabolite Analysismentioning

confidence: 99%

Induction, characterization, and NMR-based metabolic profiling of adventitious root cultures from leaf explants of Gynura procumbens

Saiman

Mustafa

Schulte³

et al. 2012

Plant Cell Tiss Organ Cult

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Gynura procumbens is a medicinal plant used in South East Asia to treat various ailments such as rash, hemorrhoids, inflammation, and diabetes. In order to develop a large-scale culture system for G. procumbens biomass containing bioactive compounds, adventitious root cultures were initiated from leaf explants. Murashige and Skoog (MS) media containing different compositions of indole-3-butyric acid (IBA), 1-naphthalene-acetic acid (NAA), and combinations of both plant growth regulators (PGRs) were evaluated for root induction. A combination of 3 mg/l NAA ? 1 mg/l IBA gave the highest root induction (48%) as compared to other PGRs treatments after 9 weeks of incubation period. Subsequently, the adventitious roots were established in liquid culture containing MS medium and the combination of 3 mg/l NAA ? 1 mg/l IBA. A study on the medium strength, sucrose concentration, pH, and light versus dark was conducted to optimize the in vitro culture conditions. The results showed that differences in MS medium strength from half to double strength, and light or dark condition did not significantly affect the biomass production, while the initial medium pH of 5.5 and 2% w/v sucrose concentration were most suitable for the root culture growth. Nuclear magnetic resonance (NMR) spectroscopy was performed to characterize the metabolite content in the root cultures of G. procumbens. Among the elucidated metabolites were some phenylpropanoids identified as caffeic acid, chlorogenic acid, and 3,5-di-O-caffeoylquinic acid which might be the bioactive compounds associated to the folk use of this plant.

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Identification of Chlorogenic Acid as a Resistance Factor for Thrips in Chrysanthemum

Cited by 260 publications

References 61 publications

Identification and Localization of a Lipase-like Acyltransferase in Phenylpropanoid Metabolism of Tomato (Solanum lycopersicum)

Identification and Localization of a Lipase-like Acyltransferase in Phenylpropanoid Metabolism of Tomato (Solanum lycopersicum)

Jasmonate-Dependent and -Independent Pathways Mediate Specific Effects of Solar Ultraviolet B Radiation on Leaf Phenolics and Antiherbivore Defense

Induction, characterization, and NMR-based metabolic profiling of adventitious root cultures from leaf explants of Gynura procumbens

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