Characterization of Hemiacetal Forms of Anthocyanidin 3-<i>O</i>-β-Glycopyranosides

Jordheim, Monica; Fossen, Torgils; Andersen, Øyvind M.

doi:10.1021/jf0619636

Cited by 25 publications

(30 citation statements)

References 21 publications

(44 reference statements)

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“…The latter would then be cleaved to yield the chalcone, which due to its thermolability instantly degrades into a phenolic acid and aldehyde, respectively. These data appear to be most useful, because few data are available on anthocyanin chalcones [34][35][36][37], especially on their determination by HPLC [26,38].…”

Section: Discussionmentioning

confidence: 99%

Thermal degradation of anthocyanins and its impact on color andin vitroantioxidant capacity

Sadilova

Carle

Stintzing

2007

Molecular Nutrition Food Res

333

216

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The aim of the current study was to thoroughly investigate the structural changes of anthocyanins at pH 3.5 in purified fractions from black carrot, elderberry and strawberry heated over 6 h at 95 degrees C. Degradation products were monitored by HPLC-DAD-MS(3 )to elucidate the prevailing degradation pathways. In addition, alterations of color and antioxidant properties observed upon heating were scrutinized. Most interestingly, the degradation pathways at pH 3.5 were found to differ from those at pH 1. Among others, chalcone glycosides were detected at 320 nm in heat-treated elderberry and strawberry pigment isolates, and opening of the pyrylium ring initiated anthocyanin degradation. In the case of acylated anthocyanins, acyl-glycoside moieties were split off from the flavylium backbone, first. Finally, for all pigment isolates, phenolic acids and phloroglucinaldehyde were the terminal degradation products as remainders of the B- and A-ring, respectively. Maximum and minimum antioxidant stabilizing capacities were found in black carrot and strawberry, respectively, which was explained by the high degree of acylation in the former. After heating, decline of trolox equivalent antioxidant capacity (TEAC) was observed in all samples, which was attributed to both anthocyanins and their colorless degradation products following thermal exposure. As deduced from the ratio of TEAC value and anthocyanin content, the loss of anthocyanin bioactivity could not be compensated by the antioxidant capacity of newly formed colorless phenolics upon heating.

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Section: Discussionmentioning

confidence: 99%

Thermal degradation of anthocyanins and its impact on color andin vitroantioxidant capacity

Sadilova

Carle

Stintzing

2007

Molecular Nutrition Food Res

333

216

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“…Phenols can be broadly classified as simple phenols having a C6-C1 or C6-C3 structure and a single aromatic ring containing one or more hydroxyl groups; and polyphenols, which contain multiple phenol rings and are defined by a C6-C3-C6 structure bearing hydroxyl and non-hydroxyl substitutions [3]. In wines, polyphenols are responsible for color [4][5][6], tactile sensations such as astringency [7,8], and taste sensations such as bitterness [9][10][11]. In addition to sensory effects on astringency, taste, and aroma modulation [12], flavonoids also play a critical role in the chemical stability of the wine during aging as these molecules intervene in metal-catalyzed oxidation reactions [13,14].…”

Section: Introductionmentioning

confidence: 99%

Agronomical and Chemical Effects of the Timing of Cluster Thinning on Pinot Noir (Clone 115) Grapes and Wines

2018

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Abstract:A two-year study was performed to evaluate the effects of the timing of cluster thinning on Pinot noir grapes and wines in the central coast of California. Vines were thinned to one cluster per shoot at three selected time-points during the growing season, and fruit was harvested and made into wine. No consistent effect of cluster thinning was found in wine phenolic profile or color across a cool (2016) and a warm (2017) growing season. The growing season had a more significant effect than the cluster thinning treatment for most parameters measured. There was no detectable overall sensory difference between the non-thinned control wines and any of the thinned treatment wines. Based on current results, Pinot noir vineyards on the central coast of California can support crop loads that result in Ravaz Index values from 3 to 6 without concern for impacting ripening potential or negatively affecting fruit composition.

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“…This formed a biose identical to rutinose [2] that was bonded to C 3 of the aglycon. The chemical shifts of the aromatic protons did not correlate with those for the flavylium cation because the isolated anthocyan glycoside was the hemiacetal form [5]. The PMR data given above did agree fully with those.…”

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confidence: 81%

“…The site of attachment of the sugar was determined by oxidative destruction of the glycoside [4,6]. This formed a biose identical to rutinose [2] that was bonded to C 3 of the aglycon.PMR spectrum (600 MHz, CD 3 OD, δ, ppm, J/Hz): 6.48 (1H, d, J = 0.8, H-4), 6.01 (1H, d, J = 2.1, H-6), 5.99 (1H, dd, J = 2.12, H-8), 7.09 (1H, d, J = 2.12, H-2′), 6.82 (1H, d, J = 8.0, H-5′), 6.98 (1H, dd, J = 2.14, 8.4, H-6′), 4.99 (1H, m, Glc H-1), 4.32 (1H, d, J = 1.68, Rha H-1), 1.32 (3H, d, J = 6.3, Rha CH 3 ).The chemical shifts of the aromatic protons did not correlate with those for the flavylium cation because the isolated anthocyan glycoside was the hemiacetal form [5]. The PMR data given above did agree fully with those.…”

mentioning

confidence: 99%

Anthocyan glycoside from Hedera colchica

Alaniya¹,

Kavtaradze²,

Skhirtladze³

2008

Chem Nat Compd

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Hedera colchica is an evergreen vine [1]. Observations carried out by us on separate specimens of H. colchica showed that the color changes depending on the vegetative phase. Thus, the stems and leaves acquire a green color during active vegetation whereas they become reddish during winter. We collected samples of the plant in Tbilisi (Georgia) in January and July 2007 in order to explain the essence of this phenomenon.The flavonol glycoside rutin has been previously isolated from H. colchica [2]. Rutin was not observed in the aqueous alcohol extract of a sample collected in January. It was found that the rutin content varies depending on the season. Rutin accumulated most (0.57%) in summer. In January, its content decreases to only traces whereas the anthocyan content changes in the opposite direction. Anthocyan pigment was completely absent in the summer sample whereas its content in the January sample reached 0.52%.Aerial parts of the plant collected in January were extracted by the method proposed for isolating anthocyan pigments [3]. The extraction was performed using methanol containing conc. HCl (0.1%) at room temperature in the dark. The resulting extract was purified by adsorption chromatography over cellulose sorbent and using reversed-phase HPLC (Agilent HP 1100, Palo Alto, USA) with a UV detector and fixed wavelength of 520 nm. We used an XTerra column (300 × 7.8 mm) packed with Silica gel RP-18 adsorbent (5 μm). The mobile phase flow rate was 2 mL/min. Samples (5 mg) (the fraction containing anthocyan pigment produced by chromatography over cellulose) were dissolved in methanol (100 μL) and injected into the chromatograph. The mobile phase was binary solutions of CH 3 CN and H 2 O containing trifluoroacetic acid (0.1%, from 10:90 to 60:40). The duration was 60 min; retention time of anthocyan, 15.63 min.A pure compound that in daylight on PC gave a pink spot; in UV light, a bright pinkish-red fluorescence; and in ammonia vapor and upon spraying with aqueous NaOH solution (1%), a bright blue color, was produced. IR spectrum (KBr, ν, cm −1 ): 3300-3400 (OH), 1655 (C=O), 1615-1430 (Ar). UV spectrum (MeOH containing HCl, 0.01%, λ max , nm): 520.Addition of methanolic AlCl 3 (5%) caused a bathochromic shift of 30 nm, which is typical of anthocyans containing free hydroxyls in the 3′-and 4′-positions [4].Acid hydrolysis gave D-glucose, L-rhamnose, and the aglycon with mp >300°C (dec.). UV spectrum (MeOH, 0.01% HCl, λ max , nm): 535; +AlCl 3 , 565. This indicated the presence of an o-dihydroxy group in the side chain. Alkaline cleavage of the algycon formed phloroglucinol and protocatechoic acid. Chromatography by PC using n-BuOH:HCl (2 N) (1:1, upper phase) and CH 3 CO 2 H:HCl:H 2 O (5:1:5), R f 0.68 and 0.35, corresponded to cyanidin [4].Stepwise acid hydrolysis of the glycoside by Hcl (4%) in methanol for 25-30 min gave an intermediate and L-rhamnose. The site of attachment of the sugar was determined by oxidative destruction of the glycoside [4,6]. This formed a biose identical to rutinose [2] that was ...

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

Cited by 25 publications

References 21 publications

Thermal degradation of anthocyanins and its impact on color andin vitroantioxidant capacity

Thermal degradation of anthocyanins and its impact on color andin vitroantioxidant capacity

Agronomical and Chemical Effects of the Timing of Cluster Thinning on Pinot Noir (Clone 115) Grapes and Wines

Anthocyan glycoside from Hedera colchica

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