Pelargonidin Glycosides Research Articles

3-Hydroxy-4′-methoxyflavone from Millettia zechiana

3-Hydroxy-4′-methoxyflavone was identified for the first time from flowers of Millettia zechiana and its structure established from its chemical characteristics and from its synthesis. In addition known glycosides of kaempferol, quercetin, malvidin, cyanidin and pelargonidin were found.

The genetic controlled hydroxylation pattern of the anthocyanin b-ring in Silene dioica is not determined at the p-coumaric acid stage

The basic C-15 skeleton of flavonoids is formed by the head-to-tail condensation of three malonyl-CoA units to one molecule of hydroxycinnamoyl-CoA. The A-ring and part of the heterocyclic ring are derived from the acetate units, the B-ring from the hydroxycinnamoyl ester. The basic C-15 flavonoid is then further modified to yield the various flavonoid classes. In this biosynthetic pathway, the hydroxylation pattern of the B-ring can either be determined at the C-9 level, by starting with the appropriate hydroxycinnamoyl-CoA ester, or at the C-15 level, by hydroxylation of one of the C-15 intermediates. In Silene dioica the hydroxylation pattern of the B-ring of the anthocyanidin molecule, and of the acyl group bound to the terminal sugar at the 3-position, is controlled by gene P, whereas the binding of the acyl group is governed by gene Ac. The hydroxylation pattern of the acyl group, however, corresponds with that of the B-ring of the anthocyanidin molecule. Thus in p/p Ac/Ac plants, in which only pelargonidin glycosides are found, the acyl group is p-coumaric acid. In P/P Ac/Ac plants the anthocyanidin is cyanidin, and the acyl group is caffeic acid. This suggests that homozygous recessive p/p plants are unable to synthesize caffeic acid, which is used both as a precursor in the biosynthesis of the anthocyanidin molecule and for acylation. In this paper, we have investigated whether gene P is involved in the conversion of p-coumaric to caffeic acid.

QUANTITATIVE EVALUATION OF Rubus FRUIT ANTHOCYANIN PIGMENTS

ABSTRACTThe distribution of individual anthocyanin pigments in the fruits of 43 Rubus clones was determined by TLC and densitometry. Quantitative estimates of anthocyanin pigments were based on absorbance at 533 nm. The fruit of all red and black raspberries and blackberries contained cyanidin 3‐glucoside. Some blackberries also contained cyanidin 3‐rutinoside. Cyanidin 3‐rutinoside and cyanidin 3‐glucosylrutinoside were also present in most red raspberries. Cyanidin 3‐sophoroside was present only in red raspberry and red raspberry hybrids while cyandin 3‐sambubioside and cyanidin 3‐xylosylrutinoside were found only in black raspberries. R. crataegifolius, R. morifolius, R. illecebrosus and R. parviflorus each contained pelargonidin glycosides as major pigments. Black raspberry had the highest anthocyanin content, over 200 mg/100g of fruit, and red raspberry had the lowest, less than 60 mg/100g. Blackberry was generally intermediate in anthocyanin content between red and black raspberries.

Fruit Anthocyanin Pigments of Red Raspberry Cultivars 1

Abstract The distribution of cyanidin and pelargonidin fruit anthocyanins is presented for 37 red raspberry (Rubus idaeus L.) cultivars and selections. Nine cultivars contained 2 major fruit pigments, cyanidin 3-glucoside (Cy 3-G1) and cyanidin 3-sophoroside (Cy 3-Sop); 27 cultivars contained in addition 2 other major pigments, cyanidin 3-rutinoside (Cy 3-Ru) and cyanidin 3-glucosylrutinoside (Cy 3-G1Ru); and 1 selection ‘SHRI 6626/41’ contained in addition to the 4 pigments, cyanidin 3-sambubioside (Cy 3-Sam) and cyanidin 3-xylosylrutinoside (Cy 3-XylRu). Related pelargonidin glycosides were detected most cultivars and cyanidin 3, 5-diglucoside (Cy 3, 5-diG1) was detected in 13 cultivars.

Anthocyanins of Cornus alternifolia, L. and C. alba, L.1

Abstract The anthocyanins of dogwood are quite heterogenous. Our earlier investigations on cornelian cherry, Cornus mas L. (1, 2) indicated that the anthocyanins were pelargonidin-3-galactoside, pelargonidin-3-robinobioside, cyanidin-3-galactoside, delphinidin-3-robinobioside and delphinidin-3-galactoside. Although the same cyanidin and pelargonidin glycosides were found in bunchberry (3), C. canadensis, in addition to the glucosides and rutinosides of pelargonidin and cyanidin, galactosides and glucosides were prevalent in other dogwood species (4). Pelargonidin and delphinidin glycosides were present either as minor or trace pigments. The robinoside of delphinidin has not been detected in any of these species. This communication reports the anthocyanins present in the berries and petioles of blue dogwood, C. alternifolia, and the red bark of Siberian dogwood, C. alba.

Evolution des flavonoides au cours de la croissance des bractees de Poinsettia

The changes in flavonoids were studies during the growth of Poinsettia bracts. Pelargonidin glycosides appeared after cyanidin glycosides; the 3-rutinoside after the 3-monoglucoside. The 3-mono-glucosides were predominant at all times. The bracts contained kaempferol and quercetin, both as aglycones and glycosides. There was no direct relationship between the pathways of flavonol and anthocyanin biosynthesis, but two separate pathways corresponding to the 4′-monohydroxylated- and 3′,4′-dihydroxylated-, flavonoids. Flavanonols and isoflavones were detected but not characterized.

Anthocyanin pattern in the genera Ilex and Euonymus

Three kinds of anthocyanin were found in the skins of fruits of seventeen plants belonging to the genera Ilex and Euonymus. They were identified as pelargonidin 3-xylosylglucoside, cyanidin 3-xylosylglucoside and cyanidin 3-monoglucoside on the basis of paper chromatographic analysis. Cyanidin 3-xylosylglucoside was commonly found in the genus Ilex which could be divided into two tribes, one containing only cyanidin glycosides, while the other contains glycosides of both pelargonidin and cyanidin. In species of the closely allied genus, Euonymus, cyanidin 3-monoglucoside was detected as the predominant pigment. In addition a detectable amount of cyanidin 3-xylosylglucoside was also present in the fruits of Euonymus japonicus and its varieties.

Flavonoid Pigments in Mimulus cardinalis and Its Related Species. I. Anthocyanins

Chromatographic and spectrophotometric techniques were used to identify the anthocyanin pigments present in Mimulus cardinalis and its related species of section Erythranthe of the genus Mimulus (Scrophulariaceae). On the basis of rigorous tests, the flowers of M. cardinalis were found to contain pelargonidin-3-glucoside, pelargonidin-3-rhamnoglucoside, the caffeoyl ester of pelargonidin-3-glucoside, cyanidin-3-glucoside, cyanidin-3-rhamnoglucoside, and the caffeoyl ester of cyanidin-3-glucoside. Qualitatively all members of the group contain these six anthocyanins except M. lewisii. All of its populations lack the pelargonidin glycosides and some lack, in addition, the cyanidin-3-rhamnoglucoside. The striking differences in flower color and intensity appear to be due to quantitative differences not here analyzed.

FLAVONOID PIGMENTS IN MIMULUS CARDINALIS AND ITS RELATED SPECIES. I. ANTHOCYANINS

Chromatographic and spectrophotometric techniques were used to identify the anthocyanin pigments present in Mimulus cardinalis and its related species of section Erythranthe of the genus Mimulus (Scrophulariaceae). On the basis of rigorous tests, the flowers of M. cardinalis were found to contain pelargonidin‐3‐glucoside, pelargonidin‐3‐rhamnoglucoside, the caffeoyl ester of pelargonidin‐3‐glucoside, cyanidin‐3‐glucoside, cyanidin‐3‐rhamnoglucoside, and the caffeoyl ester of cyanidin‐3‐glucoside. Qualitatively all members of the group contain these six anthocyanins except M. lewisii. All of its populations lack the pelargonidin glycosides and some lack, in addition, the cyanidin‐3‐rhamnoglucoside. The striking differences in flower color and intensity appear to be due to quantitative differences not here analyzed.

The inheritance of flower colour pigments I. the genusAntirrhinum

1. The. pigments of varieties, hybrids and seven species ofAntirrhinum have, been studied by paper chromatography. 2. The presence of glycosides of cyanidin, pelargonidin, apigenin and luteolin, described by earlier workers, is confirmed by this method. In addition, glycosides of aureusidin, a benzalcomriaranone, have been found, together with an unidentified aglycone (pigment 4); a second unidentified pigment is only found inA. orontium. 3. WithinA. majus single genes affect (1) the ability to produce any pigment at all (Y) (2) the ability to produce anthocyanin (R) and (3) the type of anthocyanin (B). Homo-logues of these genes occur in the speciesA. molle, A. meonanthum, A. linkianum, andA. ramosissimum. 4. The geneB produces cyanidin, and this gene or one closely linked to it is necessary for the production of the unidentified pigment 4. In the absence ofB, pelargonidin is formed, accompanied by two glycosides of apigenin. A third apigenin glycoside is found in all genotypes exceptyy. A major gene,L, is probably necessary for the production of luteolin. 5. The geneI, which determines the quantity and distribution of the yellow pigment, aureusidin, shows reversal of dominance in different groups of interspecific hybrids. This reversal may be due to a gene complex which modifies the production of anthocyanin and anthoxanthin. 6. A tentative scheme of pigment synthesis is outlined. This is based on the assumption that the genes affect precursors of the pigments rather than the pigments themselves and that the final products are the result of interaction and competition between these precursors.

Relation of leuco-anthocyanins to anthocyanin synthesis.

AMONG the herbaceous plants which Bate-Smith and Lerner1 have recently found to contain leuco-anthocyanins were Impatiens noli-tangere and I. parviflora of the Balsaminaceae. We have been investigating the genetic control of anthocyanin pigmentation in Impatiens balsamina, which has been reported previously to produce glycosides of pelargonidin, peonidin and malvidin2. In the course of these studies we have obtained evidence that the leuco-anthocyanins may serve as precursors for the anthocyanin pigments. In view of current interest in the leuco-anthocyanins, this aspect of the work is presented here.