The Biosynthetic Pathway of Major Avenanthramides in Oat

Li, Zhiyong; Chen, Yi; Meesapyodsuk, Dauenpen; Qiu, Xiao

doi:10.3390/metabo9080163

Cited by 22 publications

(33 citation statements)

References 38 publications

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“…5). Additional gene duplication occurred in oat, leading to six putative HHT isoforms, including the characterized AsHHT1 and AsHHT4 (Li et al, 2019). The expression of DcHCBT and AsHHTs are mainly induced after pathogen infection in accordance with the phytoalexin function of avenanthramides (Yang et al, 1997(Yang et al, , 2004.…”

Section: Clusters Dchcbt and Ashht1mentioning

confidence: 99%

Phenolamides in plants: an update on their function, regulation, and origin of their biosynthetic enzymes

Roumani

Besseau

Gagneul

et al. 2020

Journal of Experimental Botany

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Phenolamides represent a family of specialized metabolites, consisting of the association of hydroxycinnamic acid derivatives with aliphatic or aromatic amines. Since the discovery of the first phenolamide in the late 1940s, decades of phytochemical analyses have revealed a high structural diversity for this family and a wide distribution in the plant kingdom. The occurrence of structurally diverse phenolamides in almost all plant organs has led to early hypotheses on their involvement in floral initiation and fertility, as well as plant defense against biotic and abiotic stress. In the present work, we critically review the literature ascribing functional hypotheses to phenolamides and recent evidence on the control of their biosynthesis in response to biotic stress. We additionally provide a phylogenetic analysis of the numerous N-hydroxycinnamoyltransferases involved in the synthesis of phenolamides and discuss the potential role of other enzyme families in their diversification. The data presented suggest multiple evolutionary events that contributed to the extension of the taxonomic distribution and diversity of phenolamides.

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Section: Clusters Dchcbt and Ashht1mentioning

confidence: 99%

Phenolamides in plants: an update on their function, regulation, and origin of their biosynthetic enzymes

Roumani

Besseau

Gagneul

et al. 2020

Journal of Experimental Botany

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“…Anthranilate also plays an important role in the synthesis of avenanthramides (Ava), which are oat phytoalexins that are produced in response to pathogen infection. Ava have been found to form dimers and are incorporated into plant cell walls for reinforcement; thus, they function in both the chemical and physical defence of oat against pathogens [ 48 , 49 ].…”

Section: Discussionmentioning

confidence: 99%

Metabolomics for Biomarker Discovery: Key Signatory Metabolic Profiles for the Identification and Discrimination of Oat Cultivars

et al. 2021

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The first step in crop introduction—or breeding programmes—requires cultivar identification and characterisation. Rapid identification methods would therefore greatly improve registration, breeding, seed, trade and inspection processes. Metabolomics has proven to be indispensable in interrogating cellular biochemistry and phenotyping. Furthermore, metabolic fingerprints are chemical maps that can provide detailed insights into the molecular composition of a biological system under consideration. Here, metabolomics was applied to unravel differential metabolic profiles of various oat (Avena sativa) cultivars (Magnifico, Dunnart, Pallinup, Overberg and SWK001) and to identify signatory biomarkers for cultivar identification. The respective cultivars were grown under controlled conditions up to the 3-week maturity stage, and leaves and roots were harvested for each cultivar. Metabolites were extracted using 80% methanol, and extracts were analysed on an ultra-high performance liquid chromatography (UHPLC) system coupled to a quadrupole time-of-flight (qTOF) high-definition mass spectrometer analytical platform. The generated data were processed and analysed using multivariate statistical methods. Principal component analysis (PCA) models were computed for both leaf and root data, with PCA score plots indicating cultivar-related clustering of the samples and pointing to underlying differential metabolic profiles of these cultivars. Further multivariate analyses were performed to profile differential signatory markers, which included carboxylic acids, amino acids, fatty acids, phenolic compounds (hydroxycinnamic and hydroxybenzoic acids, and associated derivatives) and flavonoids, among the respective cultivars. Based on the key signatory metabolic markers, the cultivars were successfully distinguished from one another in profiles derived from both leaves and roots. The study demonstrates that metabolomics can be used as a rapid phenotyping tool for cultivar differentiation.

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“…Moreover, avenanthramides exhibit strong antioxidant properties with up to 30-fold greater activity than other phenolic compounds produced in oats [ 16 , 17 , 18 ]. To date, more than 25 different types of avenanthramides have been identified in oats [ 19 , 20 , 21 ]. Avenanthramides are a group of alkaloids that comprise an anthranilic acid derivative linked to a hydroxycinnamic acid derivative by an amide bond [ 5 , 19 , 22 ].…”

Section: Introductionmentioning

confidence: 99%

“…The phenylpropanoid pathway provides precursors for many secondary metabolites in plants, including lignins, anthocyanins, and flavonoids [ 26 ]. Avenanthramides are synthesized through a condensation process involving hydroxyanthranilic acid and hydroxycinnamoyl-CoA, which is catalyzed by the key enzyme hydroxycinnamoyl-CoA:hydroxyanthranilate N-hydroxycinnamoyl transferase (HHT) [ 7 , 8 , 21 ]. To date, six HHT and one caffeoyl-CoA O -methyltransferase ( CCoAOMT ) cDNAs have been isolated from oats [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

“…To date, six HHT and one caffeoyl-CoA O -methyltransferase ( CCoAOMT ) cDNAs have been isolated from oats [ 8 ]. The encoded isoforms of AsHHT1–3 (~95 to 98%) and AsHHT4–6 (~95%) share high amino acid sequence identity, whereas isoforms of AsHHT4–6 exhibit somewhat low amino acid sequence identity (~82%) with AsHTT1–3 [ 21 ]. A previous study reported that expression of AsHHT1 and CCoAOMT is concomitantly induced along with phytoalexin accumulation by a vitorin elicitor in Pc-2 / Vb oat lines [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

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Synergistic Effect of Methyl Jasmonate and Abscisic Acid Co-Treatment on Avenanthramide Production in Germinating Oats

Kim

Jeong

et al. 2021

IJMS

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The oat (Avena sativa L.) is a grain of the Poaceae grass family and contains many powerful anti-oxidants, including avenanthramides as phenolic alkaloids with anti-inflammatory, anti-oxidant, anti-itch, anti-irritant, and anti-atherogenic activities. Here, the treatment of germinating oats with methyl jasmonate (MeJA) or abscisic acid (ABA) resulted in 2.5-fold (582.9 mg/kg FW) and 2.8-fold (642.9 mg/kg FW) increase in avenanthramide content, respectively, relative to untreated controls (232.6 mg/kg FW). Moreover, MeJA and ABA co-treatment synergistically increased avenanthramide production in germinating oats to 1505 mg/kg FW. Individual or combined MeJA and ABA treatment increased the expression of genes encoding key catalytic enzymes in the avenanthramide-biosynthesis pathway, including hydroxycinnamoyl-CoA:hydrocyanthranilate N-hydroxycinnamoyl transferase (HHT). Further analyses showed that six AsHHT genes were effectively upregulated by MeJA or ABA treatment, especially AsHHT4 for MeJA and AsHHT5 for ABA, thereby enhancing the production of all three avenanthramides in germinating oats. Specifically, AsHHT5 exhibited the highest expression following MeJA and ABA co-treatment, indicating that AsHHT5 played a more crucial role in avenanthramide biosynthesis in response to MeJA and ABA co-treatment of germinating oats. These findings suggest that elicitor-mediated metabolite farming using MeJA and ABA could be a valuable method for avenanthramide production in germinating oats.

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The Biosynthetic Pathway of Major Avenanthramides in Oat

Cited by 22 publications

References 38 publications

Phenolamides in plants: an update on their function, regulation, and origin of their biosynthetic enzymes

Phenolamides in plants: an update on their function, regulation, and origin of their biosynthetic enzymes

Metabolomics for Biomarker Discovery: Key Signatory Metabolic Profiles for the Identification and Discrimination of Oat Cultivars

Synergistic Effect of Methyl Jasmonate and Abscisic Acid Co-Treatment on Avenanthramide Production in Germinating Oats

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