Malonylated flavonol glycosides from the petals of Clitoria ternatea

Kazuma, Kohei; Noda, Naonobu; Suzuki, Masahiko

doi:10.1016/s0031-9422(02)00486-7

Cited by 385 publications

(280 citation statements)

References 14 publications

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“…Triglycosides of volatiles consisting of different sugar combinations have been reported in plants before (Herderich et al, 1992;Bilia et al, 1994;Kijima et al, 1997). Also, malonylation of sugar moieties is a common feature in several plants (Withopf et al, 1997;Kazuma et al, 2003;D'Auria et al, 2007;Kogawa et al, 2007). To our knowledge, however, malonylated triglycosides of volatile compounds have not been described in plants to date.…”

Section: Emission Of Php Volatiles From Tomato Fruit Upon Tissue Disrmentioning

confidence: 93%

A Role for Differential Glycoconjugation in the Emission of Phenylpropanoid Volatiles from Tomato Fruit Discovered Using a Metabolic Data Fusion Approach

Tikunov

Vos²,

González-Paramás³

et al. 2009

Plant Physiology

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A role for differential glycoconjugation in the emission of phenylpropanoid volatiles from ripening tomato fruit (Solanum lycopersicum) upon fruit tissue disruption has been discovered in this study. Application of a multiinstrumental analytical platform for metabolic profiling of fruits from a diverse collection of tomato cultivars revealed that emission of three discriminatory phenylpropanoid volatiles, namely methyl salicylate, guaiacol, and eugenol, took place upon disruption of fruit tissue through cleavage of the corresponding glycoconjugates, identified putatively as hexose-pentosides. However, in certain genotypes, phenylpropanoid volatile emission was arrested due to the corresponding hexose-pentoside precursors having been converted into glycoconjugate species of a higher complexity: dihexose-pentosides and malonyl-dihexose-pentosides. This glycoside conversion was established to occur in tomato fruit during the later phases of fruit ripening and has consequently led to the inability of red fruits of these genotypes to emit key phenylpropanoid volatiles upon fruit tissue disruption. This principle of volatile emission regulation can pave the way to new strategies for controlling tomato fruit flavor and taste.

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Section: Emission Of Php Volatiles From Tomato Fruit Upon Tissue Disrmentioning

confidence: 93%

A Role for Differential Glycoconjugation in the Emission of Phenylpropanoid Volatiles from Tomato Fruit Discovered Using a Metabolic Data Fusion Approach

Tikunov

Vos²,

González-Paramás³

et al. 2009

Plant Physiology

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“…Ternatins are delphinidin 3-O-(6 00 -O-malonyl)--glucoside derivatives that have a 3 0 ,5 0 -di-O--glucoside structure in their B-ring, in which both glucosyl residues are alternately acylated and glucosylated in repetitions by p-coumaroyl and glucosyl groups (Kazuma et al, 2003(Kazuma et al, , 2004. Studies on ternatin biosynthesis in C. ternatea revealed that delphinidin is not directly glucosylated at the 3 0 -or 5 0 -hydroxyl group, but that glucosylation of delphinidin occurs only when it has a 6 00 -Omalonyl--glucoside at the 3-position.…”

Section: Introductionmentioning

confidence: 99%

Crystal structure of UDP-glucose:anthocyanidin 3-O-glucosyltransferase fromClitoria ternatea

Hiromoto

Honjo

Tamada

et al. 2013

J Synchrotron Radiat

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Flowers of the butterfly pea (Clitoria ternatea) accumulate a group of polyacylated anthocyanins, named ternatins, in their petals. The first step in ternatin biosynthesis is the transfer of glucose from UDP‐glucose to anthocyanidins such as delphinidin, a reaction catalyzed in C. ternatea by UDP‐glucose:anthocyanidin 3‐O‐glucosyltransferase (Ct3GT‐A; AB185904). To elucidate the structure–function relationship of Ct3GT‐A, recombinant Ct3GT‐A was expressed in Escherichia coli and its tertiary structure was determined to 1.85 Å resolution by using X‐ray crystallography. The structure of Ct3GT‐A shows a common folding topology, the GT‐B fold, comprised of two Rossmann‐like β/α/β domains and a cleft located between the N‐ and C‐domains containing two cavities that are used as binding sites for the donor (UDP‐Glc) and acceptor substrates. By comparing the structure of Ct3GT‐A with that of the flavonoid glycosyltransferase VvGT1 from red grape (Vitis vinifera) in complex with UDP‐2‐deoxy‐2‐fluoro glucose and kaempferol, locations of the catalytic His‐Asp dyad and the residues involved in recognizing UDP‐2‐deoxy‐2‐fluoro glucose were essentially identical in Ct3GT‐A, but certain residues of VvGT1 involved in binding kaempferol were found to be substituted in Ct3GT‐A. These findings are important for understanding the differentiation of acceptor‐substrate recognition in these two enzymes.

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“…The polar extract of the flowers of both species were subjected to analytical HPLC followed by semi-preparative reverse-phase HPLC to reveal 13 secondary metabolites. Six compounds were isolated from the Illawarra flame tree flower (B. acerifolius): these were quercetin 1 [14] , pelargonidin 3-(6-coumarylglucoside)-5-(6-acetylglucoside) 2 [15] , kaempferol 3-rutinoside 3 [14] , and kaempferol 6 [14] . Compound 4 and 5 were isolated as naringenin 7-O-β-glucuronide and 4,5-dihydroxylavanone 7-O-β-D-glucuronide methyl ester and their NMR spectroscopic data and low-resolution electron impact mass spectrometry were compared (see supporting information).…”

mentioning

confidence: 99%

“…[16] Therefore, we report here for the first time the isolation and characterization of the (2S)-4,5-dihydroxylavanone 7-O-β-D-glucuronide methyl ester. In addition, gallic acid 7 [17] , 2,3,5-trihydroxybenzoic acid 8 [17,18] , avicularin 9 [12] , quercetin 10 [12] , quercetin 3-glucoside 11 [14] , isorhamnetin 3-rutinoside 12 [19] , and malvidin 3-(coumaryl-glucoside)-5-(acetylxyloside) 13 [20] were isolated from Alstonville (T. lepidota) flower. All the isolated secondary metabolites have been previously reported and their spectroscopy data were compared as part of this study but importantly, they were isolated from these species here for the first time.…”

mentioning

confidence: 99%

Flowers in Australia: Phytochemical Studies on the Illawarra Flame Tree and Alstonville

Hendra

Keller

2016

Aust. J. Chem.

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The first reported phytochemical studies on two species of flowers in Australia enabled the identification of six secondary metabolites from Illawarra flame tree flower (Brachychiton acerifolius) and seven secondary metabolites from the flowers of the Alstonville (Tibouchina lepidota). Pelargonidin 3-(6-coumarylglucoside)-5-(6-acetylglucoside) was found to be responsible for the red colour of B. acerifolius, whereas malvidin 3-(coumarylglucoside)-5-(acetylxyloside) was responsible for the purple colour of (T. lepidota) flowers. (2S)-4,5-Dihydroxyflavanone 7-O-β-d-glucuronide methyl ester was isolated for the first time from B. acerifolius, and its absolute configuration was determined by circular dichroism spectroscopy. Some of the traditional uses of B. acerifolius could also be correlated with the known activity of the isolated metabolites. AbstractThe first reported phytochemical studies into two species of flowers in Australia resulted in the identification of six secondary metabolites from Illawarra flame tree flower (Brachychiton acerifolius) and seven from the flowers of the Alstonville (Tibouchina lepidota). Pelargonidin 3-(6-coumarylglucoside)-5-(6-acetyl-glucoside) was found to be responsible for the red colour from B. acerifolius while malvidin 3-(coumarylglucoside)-5-(acetylxyloside) for the purple colour from (T. lepidota) flowers. (2S)-4,5-Dihydroxylavanone 7-O-β-D-glucuronide methyl ester was isolated for the first time from B acerifolius and its absolute configuration was determined by circular dichroism spectroscopy. Some of the traditional uses of B. aerifoius could also be correlated to the known activity of the isolated metabolites.Before European settlement of Australia, the indigenous people used plants and flowers for numerous purposes including as nutrients, medicine, and dyes. [1] Australia has over 30,000 described species of vascular plants which grow in a wide range of climatic types encompassed by the continent allowing a diversity of plants and flowers unlike any other country. [2] However, there is limited information available pertaining to the phytochemical studies of Australian flowers.

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Malonylated flavonol glycosides from the petals of Clitoria ternatea

Cited by 385 publications

References 14 publications

A Role for Differential Glycoconjugation in the Emission of Phenylpropanoid Volatiles from Tomato Fruit Discovered Using a Metabolic Data Fusion Approach

A Role for Differential Glycoconjugation in the Emission of Phenylpropanoid Volatiles from Tomato Fruit Discovered Using a Metabolic Data Fusion Approach

Crystal structure of UDP-glucose:anthocyanidin 3-O-glucosyltransferase fromClitoria ternatea

Flowers in Australia: Phytochemical Studies on the Illawarra Flame Tree and Alstonville

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