Abnormal metabolites of wheat: Occurrence, isolation and biogenesis of 2-hydroxyputrescine amides

Samborski, D. J.; Rohringer, R.

doi:10.1016/s0031-9422(00)85343-1

Cited by 53 publications

(23 citation statements)

References 13 publications

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“…N. tabacum cv Xanthi nc forms large amounts of mono-and diferuloylputrescine after infection with the tobacco mosaic virus (44). As described previously, p-coumaroyl-2-hydroxyputrescine accumulates in wheat challenged with rust (42). The hordatines in barley increase up to 6-fold 13 days after inoculation with powdery mildew (45).…”

Section: Discussionsupporting

confidence: 70%

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Structural Analyses and Dynamics of Soluble and Cell Wall-bound Phenolics in a Broad Spectrum Resistance to the Powdery Mildew Fungus in Barley

Röpenack¹,

Parr²,

Schulze‐Lefert³

1998

Journal of Biological Chemistry

210

159

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High pressure liquid chromatography profiles of barley leaf epidermal soluble and cell wall-bound phenolics were analyzed in response to challenge with the fungal pathogen Erysiphe graminis f. sp. hordei. Only one soluble phenolic was found to accumulate differentially in a broad spectrum resistance reaction controlled by mlo resistance alleles in comparison to susceptible near isogenic Mlo lines. Structural analysis identified this compound as a novel phenolic conjugate, p-coumaroyl-hydroxyagmatine (p-CHA). p-CHA but not the nonhydroxylated derivative p-coumaroylagmatine exhibited antifungal activity both in vitro and in vivo. The accumulation of p-CHA in epidermal tissue correlated tightly with fungal penetration attempts of attacked host cells. Furthermore, upon penetration, epidermal cell wallbound phenolics became resistant to saponification at sites of attempted fungal ingress (papilla), indicating a change in, or the addition of, different chemical bonding types. The switch in saponification sensitivity occurred at least 2 h earlier in the mlo-incompatible than in the Mlo-compatible interaction. Our results suggest that p-CHA and the speed of papillae compaction play important roles in non-racespecific powdery mildew defense.

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Section: Discussionsupporting

confidence: 70%

“…Labeling studies of a p-CHA-related substance in wheat, p-coumaroyl-2-hydroxyputrescine, suggests that hydroxylation occurs directly at the amino acid level (42). These data support hydroxylation of the arginine for p-CHA formation.…”

Section: Discussionmentioning

confidence: 70%

Structural Analyses and Dynamics of Soluble and Cell Wall-bound Phenolics in a Broad Spectrum Resistance to the Powdery Mildew Fungus in Barley

Röpenack¹,

Parr²,

Schulze‐Lefert³

1998

Journal of Biological Chemistry

210

159

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“…Hydroxycinnamic acids, hydroxycinnamate: CoA ligases to produce hydroxycinnamoyl-CoA including p-coumaroylCoA (Gross, 1981), and condensation products between hydroxycinnamoyl-CoA and polyamines such as pcoumaroyl and feruloylputrescines are commonly found in plants (Martin-Tanguy, 1985), including wheat (Moerschbacher et al, 1986;Maule and Ride, 1983;Samborski and Rohringer, 1970). Arginine and arginine decarboxylase to produce agmatine are also widely distributed in the plant kingdom (Slocum et al, 1984).…”

Section: Discussionmentioning

confidence: 99%

Occurrence of hordatines, the barley antifungal colnpounds, in a wheat-barley chromosome addition line.

et al. 1999

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Hordatines A and B, strong antifungal components in shoots of barley seedlings, were found to occur in a barley chromosome 2H addition line to wheat, but not in a wheat line carrying the long arm of chromosome 2H. These results showed that some genes that encode hordatine biosynthetic enzymes are located on the short arm of chromosome 2H. The total content of the hordatines was about six fold less than that in the parental barley, but was still at a concentration more than 20-fold higher than that required for inhibition of spore germination of pathogenic fungi.

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“…Among cereals, 4-coumaroyltryptamine and feruloyltryptamine have been identified in maize (Zea mays), while avenanthramides (substituted N-cinnamoylanthranilates) have been isolated from oat (Avena sativa) (Collins, 1989). Hydroxycinnamoyl agmatine has been found in powdery mildewinfected barley (Hordeum vulgare) (Smith and Best, 1978), and feruloyl and coumaroyl putrescine accumulate in rust-infected wheat (Triticum aestivum) (Samborsk and Rohringe, 1970). In addition to their occurrence in floral organs, HCAAs accumulate in seeds and sometimes also in roots.…”

Section: Introductionmentioning

confidence: 99%

A Novel Polyamine Acyltransferase Responsible for the Accumulation of Spermidine Conjugates in Arabidopsis Seed

et al. 2009

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Hydroxycinnamic acid amides are a class of secondary metabolites distributed widely in plants. We have identified two sinapoyl spermidine derivatives, N-((4′-O-glycosyl)-sinapoyl),N′-sinapoylspermidine and N,N′-disinapoylspermidine, which comprise the two major polyamine conjugates that accumulate in Arabidopsis thaliana seed. Using metabolic profiling of knockout mutants to elucidate the functions of members of the BAHD acyltransferase family in Arabidopsis, we have also identified two genes encoding spermidine disinapoyl transferase (SDT) and spermidine dicoumaroyl transferase (SCT) activities. At2g23510, which is expressed mainly in seeds, encodes a spermidine sinapoyl CoA acyltransferase (SDT) that is required for the production of disinapoyl spermidine and its glucoside in Arabidopsis seed. The structurally related BAHD enzyme encoded by At2g25150 is expressed specifically in roots and has spermidine coumaroyl CoA acyltransferase (SCT) activity both in vitro and in vivo.

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Abnormal metabolites of wheat: Occurrence, isolation and biogenesis of 2-hydroxyputrescine amides

Cited by 53 publications

References 13 publications

Structural Analyses and Dynamics of Soluble and Cell Wall-bound Phenolics in a Broad Spectrum Resistance to the Powdery Mildew Fungus in Barley

Structural Analyses and Dynamics of Soluble and Cell Wall-bound Phenolics in a Broad Spectrum Resistance to the Powdery Mildew Fungus in Barley

Occurrence of hordatines, the barley antifungal colnpounds, in a wheat-barley chromosome addition line.

A Novel Polyamine Acyltransferase Responsible for the Accumulation of Spermidine Conjugates in Arabidopsis Seed

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