Identification, properties and genetic control of hydroxycinnamoyl-coenzyme A: Anthocyanidin. 3-rhamnosyl (1 → 6) glucoside, 4‴-hydroxycinnamoyl transfersae isolated from petals of Silene dioica

Kamsteeg, John; Brederode, J. van; Hommels, Cees H.; Nigtevecht, G. van

doi:10.1016/s0015-3796(80)80026-6

Cited by 37 publications

(15 citation statements)

References 13 publications

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“…Some properties of gentian 5-acyltransferase (5AT) are similar to those of 3-aromatic acyltransferases (3AT) previously reported from Silene dioica (Kamsteeg et al, 1980), Matthiola incana and Ajugu reptans (Callebaut et al, 1996). Gentian 5AT is a single polypeptide protein because its molecular mass is estimated to be 49 kDa by gel filtration and 52 kDa by SDSPAGE (Fig.…”

Section: Discussionsupporting

confidence: 70%

“…Gentian 5AT can efficiently use both caffeoyl-CoA and pcoumaroyl-CoA as acyl donors, as could other 3ATs (Kamsteeg et al, 1980;Callebaut et al, 1996). In gentian, the 5AT seems to use caffeoyl-CoA preferentially to pcoumaroyl-CoA in vivo because gentian petals accumulate anthocyanins modified with caffeic acid much more than p-coumaric acid (Figs 1 and 5).…”

Section: Discussionmentioning

confidence: 94%

“…This broad substrate specificity seems to be common in acyltransferases. Silene 3AT can acylate both cyanidin and pelargonidin 3-rhamnosylglucosides (Kamsteeg et al, 1980). Matthiola 3AT can acylate pelargonidin, cyanidin and delphinidin glycosides at similar rates, whereas the flower does not contain delphinidin glycoside .…”

Section: Discussionmentioning

confidence: 95%

“…An anthocyanin acyltransferase catalyzing acylation of the 3-rhamnosyl moiety of anthocyanidin 3-rutinoside was first isolated from Silene dioicu flowers (Kamsteeg et al, 1980). MLrtthioln incanu flowers , Daucus carota cell cultures (Glassgen and Seitz, 1992) and Ajuga reptans cell cultures (Callebaut et al, 1996) have been reported to contain hydroxycinnamoyl-CoA :anthocyanidin 3-glycoside acyltransferases.…”

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confidence: 99%

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Anthocyanin 5‐Aromatic Acyltransferase from Gentiana Triflora

Fujiwara

Tanaka

Fukui

et al. 1997

European Journal of Biochemistry

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Acylation with hydroxycinnamic acids stabilizes anthocyanins and makes their colour bluer (bathochromic shift). We purified to homogeneity one acylation enzyme, hydroxycinnamoyl-CoA :anthocyanidin 3,5-diglucoside 5-0-glucoside-6"'-O-hydroxycinnamoyltransferase, from blue petals of Gentiana triflora. It is a single polypeptide protein of 52 kDa with a PI of 4.6. It catalyzes the transfer of the p-coumaric acid and caffeic acid from their CoA esters to the 5-glucosyl moiety of anthocyanidin 3,5-diglucosides but could not use malonyl-CoA as an acyl donor. Neither anthocyanidin 3-monoglucoside nor anthocyanins aromatically acylated at the 3-glucosyl moiety could be acylated by this enzyme. Aromatic acylation of anthocyanidin 3,5-diglucoside by this enzyme caused a bathochromic shift and increased pigment stability in neutral to weakly basic pH. Other anthocyanins from the petals of G. trijlora were isolated and their structures were determined by fast-atom-bombardment MS and NMR. The biosynthetic pathway of gentiodelphin, a diacylated anthocyanin accumulating in G. triflora petals, is proposed on the basis of these results.

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Section: Discussionsupporting

confidence: 70%

Section: Discussionmentioning

confidence: 94%

Section: Discussionmentioning

confidence: 95%

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confidence: 99%

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Anthocyanin 5‐Aromatic Acyltransferase from Gentiana Triflora

Fujiwara

Tanaka

Fukui

et al. 1997

European Journal of Biochemistry

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“…in the formation of 0-esters with quinic acid (22), shikimic acid (35), lupinine (15, Strack D, Becher A, Brall S, Witte L, unpublished data), tartronic acid (25), isocitric acid (29), various sugar acids (28), 3,4-bishydroxylactic acid (17), and 1 3-hydroxylupanine (Strack D, Becher A, Brall S, Witte L, unpublished data) as well as with flavonoids, flavonol glycosides (20), and anthocyanins (9); (b) via the 1-O-acyl-HCA glucosides, e.g. in the formation of O-esters with malic acid (33), choline (24), 1-0-sinapoylglucose in a 'disproportionation' reaction (4), quinic acid (1 1), tartaric acid (27), and glucaric acid (30) as well as with betacyanins, namely betanin and amaranthin (2).…”

Section: General Cgt Propertiesmentioning

confidence: 99%

Properties and Activity Changes of Chlorogenic Acid:Glucaric Acid Caffeoyltransferase From Tomato (Lycopersicon esculentum)

Strack

Gross²

1990

Plant Physiol.

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A novel acyltransferase from cotyledons of tomato (Lycopersicon esculentum Mill.), which catalyzes the transfer of caffeic acid from chlorogenic acid (5-O-caffeoylquinic acid) to glucanc and galactaric acids, was purified with a 2400-fold enrichment and a 4% recovery. The enzyme showed specific activities (theoretical Vi., per milligram of protein) of 625 nanokatals (caffeoylglucaric acid formation) and 310 nanokatals (caffeoylgalactaric acid formation). On sodium dodecyl sulfate-polyacrylamide gel electrophoresis it gave an apparent Mr of 40,000, identical to the value obtained by gel filtration column chromatography. Highest activity was found at pH 5.7, which was constant over a range of 20 to 120 millimolar K-phosphate. The isoelectric point of the enzyme was at pH 5.75. The reaction temperature optimum was at 380C and the apparent energy of activation was calculated to be 57 kilojoules per mole. The apparent K, values were 0.4 millimolar for glucaric acid, 1.7 millimolar for galactaric acid, and with both acceptors as second substrates 20 millimolar for chlorogenic acid. The relative ratio of the V1,,IKm values for glucaric acid and galactaric acid was found to be 100:12. Substratecompetition experiments support the conclusion that one single enzyme is responsible for both the glucaric and galactaric acid ester formation with marked preference for glucaric acid. It is proposed that the enzyme be called chlorogenic acid:glucaric acid O-caffeoyltransferase (EC 2.3.1.-). The three caffeic aciddependent enzyme activities involved in the formation of the glucaric and galactaric acid esters, the chlorogenic acid:glucaric acid caffeoyltransferase as the key activity as well as the caffeic acid:CoA ligase and the caffeoyl-CoA:quinic acid caffeoyltransferase as the preceding activities, were determined. The time course of changes in these activities were followed during development of the seedling in the cotyledons and growth of the young plant in the first and second leaf. The results from tomato seedlings suggest a sequential appearance of these enzymes.have been investigated with regard to their enzymic synthesis. One reason this biochemical area has been neglected to date might be that since the discovery of the mechanism of the biosynthesis of a caffeic acid (3,4-bishydroxycinnamic acid) ester ofquinic acid, chlorogenic acid (5-0-caffeoylquinic acid; 8), this has been widely accepted as the mechanism for all other known HCA esters. For Stockigt and Zenk showed in 1974 (22) that in tobacco cell cultures the formation of chlorogenic acid proceeds via the caffeoyl-CoA thioester as acyl donor. However, it has been shown that beside this commonly found mechanism, l-O-acyl glucosides, whose formation is catalyzed by UDP-glucose-dependent glucosyltransferases, may also act as HCA donors (1). Moreover, alternative esterifications (transacylations) may also be possible. For example, chlorogenic acid, which is common in Asteraceae, Solanaceae, and Rubiaceae (13) may act as an acyl donor molecule for caffeoyltran...

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Biochemistry and Physiology of Alkaloids and Betalains

Roberts

Strack

2018

Annual Plant Reviews Online

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The sections in this article are Introduction Nicotine and Tropane Alkaloids Pyrrolizidine Alkaloids Benzylisoquinoline Alkaloids Monoterpene Indole Alkaloids Ergot Alkaloids Acridone Alkaloid Biosynthesis Purine Alkaloids Taxol Betalains Conclusions Acknowledgements

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Identification, properties and genetic control of hydroxycinnamoyl-coenzyme A: Anthocyanidin. 3-rhamnosyl (1 → 6) glucoside, 4‴-hydroxycinnamoyl transfersae isolated from petals of Silene dioica

Cited by 37 publications

References 13 publications

Anthocyanin 5‐Aromatic Acyltransferase from Gentiana Triflora

Anthocyanin 5‐Aromatic Acyltransferase from Gentiana Triflora

Properties and Activity Changes of Chlorogenic Acid:Glucaric Acid Caffeoyltransferase From Tomato (Lycopersicon esculentum)

Biochemistry and Physiology of Alkaloids and Betalains

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