Cacao polyphenolic substances. 5. The structure of cacao ‘leucocyanidin 1’

Forsyth, W. G. C.; Roberts, J. B.

doi:10.1042/bj0740374

Cited by 55 publications

(15 citation statements)

References 8 publications

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“…For the latter, extraction with ethyl acetate (3 × 10 mL) afforded an organic phase that was concentrated to 10 mL by rotoevaporation, dried with anhydrous sodium sulfate, filtered, and brought to dryness with a nitrogen flow, before dissolving in acetone. Dimethyl sulfate was used as methylation reagent to obtain the corresponding derivatives of hydroxyl‐bearing compounds in this extract, following the procedures proposed by Hergert et al and Forsyth et al .…”

Section: Methodsmentioning

confidence: 99%

Chromatographic and mass spectrometric characterization of essential oils and extracts from Lippia (Verbenaceae) aromatic plants

Stashenko

Martı́nez

Cala

et al. 2013

J of Separation Science

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Analytical methodologies based on GC and HPLC were developed for the separation and quantification of carnosic acid, ursolic acid, caffeic acid, p-coumaric acid, rosmarinic acid, apigenin, luteolin, quercetin, kaempferol, naringenin, and pinocembrin. These methods were used to characterize essential oils and extracts obtained by solvent (methanol) and by supercritical fluid (CO(2)) extraction from stems and leaves of Lippia (Verbenaceae family) aromatic plants (Lippia alba, Lippia origanoides, Lippia micromera, Lippia americana, Lippia graveolens, and Lippia citriodora). Supercritical CO(2) extraction isolated solely pinocembrin and narigenin from three L. origanoides chemotypes. Solvent extracts possessed a more varied composition that additionally included apigenin, quercetin, and luteolin. Solvent extraction afforded higher overall flavonoid yields from all species in comparison with supercritical CO(2) extraction. Pinocembrin was determined in L. origanoides extract at a concentration of 30 mg/g of plant material, which is more than ten times higher than the amount at which polyphenols are regularly found in aromatic plant extracts.

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Section: Methodsmentioning

confidence: 99%

Chromatographic and mass spectrometric characterization of essential oils and extracts from Lippia (Verbenaceae) aromatic plants

Stashenko

Martı́nez

Cala

et al. 2013

J of Separation Science

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“…Cacao beans, the seed of Theobroma cacao, are known to contain various polyphenolic substances (7)(8)(9). It has been reported that cacao liquor, one of the main ingredients of cocoa and chocolate, prepared by fermentation of raw beans, is rich in polyphenols in spite of the processes involved in its manufacture.…”

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confidence: 99%

Cacao liquor polyphenols reduce oxidative stress without maintaining α‐tocopherol levels in rats fed a vitamin E‐deficient diet

Yamagishi

Osakabe

Takizawa

et al. 2001

Lipids

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The effect of crude polyphenols (CLP) from cacao liquor on vitamin E-deficient rats was examined. The CLP fraction contained 49.8% antioxidative polyphenols such as catechins and their oligomers. Supplementation of the vitamin E-deficient diet with CLP for 7 wk did not prevent the decrease in α-tocopherol levels in the liver, kidney, heart, brain, and plasma. The lipid peroxide levels in these tissues increased in the group fed the vitamin E-deficient diet compared with the control group. However, these changes were inhibited in a dose-dependent manner as a result of supplementation of the vitamin E-deficient diet with 0.25, 0.5, or 1.0% CLP. The lipid peroxide levels in plasma increased in the group fed the vitamin E-deficient diet. This change tended to be suppressed as a result of supplementation of the diet with CLP, but the difference was not significant. There was no evidence of absorption and distribution of CLP to the tissues; however, CLP intake resulted in a decrease in oxidative stress without maintaining vitamin E levels in the plasma and the tissues. FIG. 2. Effect of CLP on lipid peroxide levels in various tissues of rats fed the experimental diets. Values are means ± SD. Values not sharing the same letters are significantly different, P < 0.05. For abbreviations see Figure 1.

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“…The first attempt at resolution of racemic flavonoids by Brown and Fuller 17 was centered on the separation of (±)-2,3-trans-3,4-cis-3' ,4',5,7-tetramethoxyflavan-3,4-diol (1). Treatment of the racemic 3,4-diol with 4-boronobenzoic acid led to 4-carboxyphenylborate esters; i.e., (2), which were resolved into the two diastereomeric salts of the borate ester with (-)-ephedrine by repeated crystallization.…”

Section: Resolution Of Racemic Chalcone Epoxides Dihydroflavonols Amentioning

confidence: 99%

Enantioselective Synthesis of Flavonoids

Bezuidenhoudt

Ferreira

1992

Plant Polyphenols

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Enantiopure (scalemic) flavonoid monomers such as permethoxylated chalcone epoxides and dihydroflavonols are available via HPLC resolution of the racemates using a Chiralpack OT( +) column. Depending on the oxygenation pattern, epoxy chalcones can also be prepared in enantiomeric purity up to 96 percent by the utilization of synthetic poly(peptide) or cinchona alkaloid catalyzed epoxidation with hydrogen peroxide, aqueous sodium hypochlorite, or tert-butyl hydroperoxide. Transformation of these oxiranes into dihydroflavonols and ultimately flavan-3,4-diols without 'loss' in optical purity is possible by treatment with hydrogen chloride in absolute methanol, followed by sodium borohydride reduction. Direct catalytic hydrogenation of the epoxides leads to a-hydroxydihydrochalcones of comparable enantiomeric purity that can be used for determination of the absolute configuration of naturally occurring analogues by comparison of CD data.

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Cacao polyphenolic substances. 5. The structure of cacao ‘leucocyanidin 1’

Cited by 55 publications

References 8 publications

Chromatographic and mass spectrometric characterization of essential oils and extracts from Lippia (Verbenaceae) aromatic plants

Chromatographic and mass spectrometric characterization of essential oils and extracts from Lippia (Verbenaceae) aromatic plants

Cacao liquor polyphenols reduce oxidative stress without maintaining α‐tocopherol levels in rats fed a vitamin E‐deficient diet

Enantioselective Synthesis of Flavonoids

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