A Diacylated Anthocyanin from Tibouchina urvilleana Flowers

Terahara, Norihiko; Suzuki, Hiroyuki; Toki, Kenjiro; Kuwano, Harumitsu; Saitô, Norio; Honda, Toshio

doi:10.1021/np50093a004

Cited by 17 publications

(21 citation statements)

References 17 publications

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“…One-dimensional 1 H, 13 C compensated attached proton test experiment (CAPT), two-dimensional heteronuclear single quantum coherence ( 1 H- 13 with a cryogenic probe. Sample temperatures were stabilized at 298 K. The deuteriomethyl 13 C signal and the residual 1 H signal of the solvent (CF3COOD/CD3OD; 5:95, v/v) were used as secondary references (δ 49.0 and δ 3.40 from TMS, respectively).…”

Section: Methodsmentioning

confidence: 99%

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Characterization of Hemiacetal Forms of Anthocyanidin 3-O-β-Glycopyranosides

Jordheim

Fossen

Andersen

2006

J. Agric. Food Chem.

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The 3-O-beta-glucopyranosides of delphinidin, petunidin, and malvidin (1-3) and cyanidin 3-O-beta-galactopyranoside (4) dissolved in deuterated methanolic solutions without and with acid (5%, CF3COOD) were identified by homo- and heteronuclear NMR techniques. The hemiacetal forms of all the four anthocyanins were characterized as two epimeric 2-hydroxy-hemiacetals on the basis of assignments of both proton and carbon NMR signals together with chemical shift considerations. This is the first report of 13C NMR assignments of two epimeric anthocyanin hemiacetal forms. No 4-hydroxy-hemiacetal form was detected for any of the pigments. For each anthocyanin dissolved in deuterated methanol, the equilibrium between each of the two epimeric hemiacetals and the corresponding flavylium cation was confirmed by the observed positive exchange cross-peaks in the 2D 1H NOESY spectra. The molar proportions of the flavylium cation and the two hemiacetals of 1-4 in deuterated methanol were very similar for all pigments, even during storage for weeks. The majority of the anthocyanins reported to occur in fruits have the same or similar structures as 1-4. These pigments have been proposed to exist predominantly as hemiacetals in slightly acidic to neutral solvents, which is a relevant pH range in plants and in the human gastrointestinal tract.

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Section: Methodsmentioning

confidence: 99%

“…There exists only limited information about elucidation of anthocyanin hemiacetal structures in the literature (10)(11)(12)(13)(14). Under in-vivo conditions, simple anthocyanins like 1-4 occur on several equilibrium forms, of which some are unstable even during a short time of storage (21).…”

Section: Hemiacetal Forms Of Malvidin 3-o--glucopyranoside (1)mentioning

confidence: 99%

Characterization of Hemiacetal Forms of Anthocyanidin 3-O-β-Glycopyranosides

Jordheim

Fossen

Andersen

2006

J. Agric. Food Chem.

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“…The major pigment found in the flowers of T. urvilleana Cong. was identified as 3- O -[6-O-(E)-p-coumaroyl-β- d -glucopyranosyl]-5- O -(2- O -acetyl-β- d -xylopyranosyl) malvidin ( 19g ) [37]. The contents of acylated anthocyanins in the flowers of Melastomataceae give them economical importance as sources of natural food colorants.…”

Section: Chemical Constituents Of Melastomataceous Plantsmentioning

confidence: 99%

Phenolics and Polyphenolics from Melastomataceae Species

Serna

Martínez

2015

Molecules

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Abstract:The Melastomataceae family, the seventh largest flowering plants, has been studied in several fronts of natural product chemistry, including terpenoids, simple phenolics, flavonoids, quinones, lignans and their glycosides, as well as a vast range of tannins or polyphenols. This review concerns the phenolic and polyphenolic metabolites described in the literature for several genera of this family, the mode of isolation and purification, and the structure elucidation of these new natural products that has been achieved by extensive spectral analyses, including ESI-MS, 1 H-, 13 C-NMR spectra and two-dimensional experiments, COSY, TOCSY, J-resolved, NOESY, HMQC, DEPT, and HMBC, as well as chemical and enzymatic degradations and the chemotaxonomic meaning. Finally, a general biogenetic pathway map for ellagitannins is proposed on the bases of the most plausible free radical C-O oxidative coupling.

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“…[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.…”

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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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A Diacylated Anthocyanin from Tibouchina urvilleana Flowers

Cited by 17 publications

References 17 publications

Characterization of Hemiacetal Forms of Anthocyanidin 3-O-β-Glycopyranosides

Characterization of Hemiacetal Forms of Anthocyanidin 3-O-β-Glycopyranosides

Phenolics and Polyphenolics from Melastomataceae Species

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

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