Oat phenolics: avenanthramides, novel substituted N-cinnamoylanthranilate alkaloids from oat groats and hulls

Collins, F. William

doi:10.1021/jf00085a015

Cited by 258 publications

(227 citation statements)

References 11 publications

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“…The induction of avenanthram ides can be reproduced by tre atm e n t w ith elicitors such as Nacetylchitooligosaccharides (B ordin et al, 1991), victorin C (M ayam a et al, 1986), heavy m etal ions (Fink et al, 1990), and the calcium ionophore A23187 . In addition, the oc currence of avenanthram ides in oat grains and hulls as constitutive com ponents has been found (Collins, 1986;Collins, 1989;Collins et a l, 1991). In the present study, we quantitatively analyzed the avenanthram ide com position in seeds and com pared the results with those in previous re ports of elicitor-treated leaves (Ish ih ara et al, 1998).…”

Section: Discussionmentioning

confidence: 99%

“…A venanthram ides A (1), B (2) and D (4) were synthesized according to the m eth o d of Collins (1989). The synthesis of aven an th ram id es C (3), G (5), L (6 ) and o th e r related am ides has been previously rep o rted (Ishih ara et al, 1998;Miyagawa et al, 1996;M iyagaw a et al, 1995).…”

Section: Chemicalsmentioning

confidence: 99%

“…O n the o th er hand, th e hydroxycinnam ic acid am ides have also been know n to occur at specific stages of grow th in the G ram in eae family. A venan thram ides occur in oat g roats and hulls as constitu tive com ponents (Collins, 1986;Collins, 1989; Col- et al, 1991). p -C oum aroylagm atine accum ulates in barley shoots and ro o ts im m edi ately after germ ination to g eth er w ith the coupled dimers, hordatines A and B (Sm ith and Best, 1978).…”

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confidence: 99%

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Occurrence of Avenanthramides and Hydroxycinnamoyl-CoA:hydroxyanthranilate N-hydroxycinnamoyltransferase Activity in Oat Seeds

Matsukawa

Isobe

Ishihara

et al. 2000

Zeitschrift Für Naturforschung C

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O at phytoalexins, avenanthram ides, occur as constitutive com ponents in seeds. The am ounts of each av en an th ram id e w ere analyzed. The com position of av en an th ram id es in dry seeds was d ifferent from th at in elicitor-treated leaves. In seeds, av en an th ram id e C was most ab u n d an t w ith an am o u n t tw o tim es larger than th at of aven an th ram id e A o r B. O n the o th er h and , av en an th ram id e A was the m ajor com ponent in elicitor-treated leaves. The total am ount of av en an th ram id es in seeds increased 2.5 tim es during im bibition for 48 h although the com position did n o t change. The hydroxycinnam oyl-C oA :hydroxyanthranilate /V-hydroxycinnam oyltransferase (H H T, E C 2.3.1.-) activity, which is responsible for th e final co n d en sation step in th e av en an th ram id e biosynthesis, was detected in dry seeds. T he activity was localized in e n d o sp erm and scutellum , and slightly increased during 48-h im bibition. The enzym e was partially purified by anion exchange chrom atography from b o th dry seeds and elicitor-treated leaves. TTie activity was separated into two peaks by chrom atography, indicat ing th at H H T consists of at least tw o isoforms. The substrate specificities o f H H T isoform s from seeds w ere differen t from each other.

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Section: Discussionmentioning

confidence: 99%

Section: Chemicalsmentioning

confidence: 99%

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confidence: 99%

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Occurrence of Avenanthramides and Hydroxycinnamoyl-CoA:hydroxyanthranilate N-hydroxycinnamoyltransferase Activity in Oat Seeds

Matsukawa

Isobe

Ishihara

et al. 2000

Zeitschrift Für Naturforschung C

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“…AVAs (anthranilic acid amides) are a group of naturally occurring phenolic amides in oats. Oats contain a unique group of approximately 40 different types of AVAs that consist of an anthranilic acid derivatives and hydroxycinnamic acid derivatives (Collins 1989;Bratt et al 2003;Dokuyucu et al 2003;Peterson & Dımberg 2008;Wıse 2011). AVAs are low molecular weight soluble phenolic compounds. Among cereals, only oats contain AVAs (Kováčová & Malinová 2007;Moglia et al 2010;Shi et al 2014).…”

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confidence: 99%

“…Among cereals, only oats contain AVAs (Kováčová & Malinová 2007;Moglia et al 2010;Shi et al 2014). These compounds are antipathogens (phytoalexins), which are produced by the plant in response to the exposure to pathogens such as fungus (Collins & Mullin 1988;Collins 1989;Okazaki et al 2004). The three most abundant AVAs in oats are AVA-A, AVA-B, and AVA-C, which contain hydroxyanthranilic acid and a kind of hydroxycinnamic acids like p-coumaric, caffeic, or ferulic acids, respectively (Peterson et al 2002;Okazaki et al 2004;Gani et al 2012).…”

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Phenolic amides (avenanthramides) in oats - a review

Boz¹

2015

Czech J. Food Sci.

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Boz H. (2015): Phenolic amides (avenanthramides) in oats -a review. Czech J. Food Sci., 33: 399-404.Whole grain cereals such as oats are important sources of phenolic compounds. Oats contain phenolic amides, also named avenanthramides (AVAs), which have beneficial health properties because of their antioxidant, anti-inflammatory, and antiproliferative effects. The most common avenanthramides are esters of 5-hydroxyanthranilic acid with p-coumaric (AVA-A), ferulic (AVA-B), or caffeic (AVA-C) acids. The studies related to the stability of AVAs showed that AVA-B is sensitive to alkaline and neutral conditions and this sensitivity increases with higher temperatures. However, has been reported that AVA-A and AVA -C are more stable under the same conditions (alkaline and neutral conditions), and in addition that AVAs content of oats is increasing significantly with the germination process. AVAs help in preventing free radicals from damaging LDL cholesterol while AVAs-enriched extract of oats combined with vitamin C synergistically inhibited LDL oxidation in vitro. Both animal studies and human clinical trials confirmed that oats antioxidants have the potential of reducing cardiovascular risks by lowering serum cholesterol and inhibiting LDL oxidation and peroxidation. Therefore, the consumption of oats and products thereof is extremely important in reducing the risk of cardiovascular diseases.

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Chlorogenic acids and other cinnamates - nature, occurrence and dietary burden

Clifford

1999

J. Sci. Food Agric.

1,135

388

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This review defines the range of forms in which cinnamates (p‐coumarates, caffeates, ferulates and sinapates) occur in foods and beverages subdividing them into (i) the classic chlorogenic acids and close allies, (ii) other esters, amides and glycosides, and (iii) transformation products formed during processing. Cinnamate derivatives which would not release cinnamic acid by hydrolysis are excluded. The quantitative data are reviewed concisely and attention is drawn to certain shortcomings, in particular a complete absence of data for certain commodities (breakfast cereals, baked goods, tomato products and nuts) and minimal data for pulses, legumes and processed or cooked foods. In addition, more data are required for the edible portion of modern varieties. By extrapolating from such data as are available the important source(s) (i) of individual cinnamates (regardless of the conjugate type) and (ii) of each major class of conjugate, have been identified as follows: (i) Cinnamates: caffeic acid: coffee beverage, blueberries, apples, ciders; p‐coumaric acid: spinach, sugar beet fibre, cereal brans; ferulic acid: coffee beverage, citrus juices, sugar beet fibre, cereal brans; sinapic acid: broccoli, kale, other leafy brassicas, citrus juices. (ii) Conjugates: caffeoylquinic acids: coffee beverage, blueberries, apples, ciders; p‐coumaroylquinic acids: sweet cherries; feruloylquinic acids: coffee beverage; tartaric conjugates: spinach, lettuce, grapes and wines; malic conjugates: lettuce, spinach, possibly legumes; rosmarinic acid: culinary herbs, mixed herbs, possibly stuffings; cell wall conjugates: spinach, sugar beet fibre, cereal brans. It seems likely that the UK population will fall into several categories depending on (i) their consumption of coffee, (ii) their consumption of bran, and (iii) their consumption of citrus. Those who drink several cups of coffee per day augmented by bran and citrus might easily ingest 500–800 mg cinnamates (or even 1 g for the greatest coffee ingest consumption) whereas those who eschew all these and take little fresh fruit or vegetables might struggle to consume 25 mg. © 1999 Society of Chemical Industry

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Oat phenolics: avenanthramides, novel substituted N-cinnamoylanthranilate alkaloids from oat groats and hulls

Cited by 258 publications

References 11 publications

Occurrence of Avenanthramides and Hydroxycinnamoyl-CoA:hydroxyanthranilate N-hydroxycinnamoyltransferase Activity in Oat Seeds

Occurrence of Avenanthramides and Hydroxycinnamoyl-CoA:hydroxyanthranilate N-hydroxycinnamoyltransferase Activity in Oat Seeds

Phenolic amides (avenanthramides) in oats - a review

Chlorogenic acids and other cinnamates - nature, occurrence and dietary burden

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