Impact of location, type, and number of glycosidic substitutions on the color expression of o-dihydroxylated anthocyanidins

Sigurdson, Gregory T.; Robbins, Rebecca J.; Collins, Thomas M.; Giusti, M. Mónica

doi:10.1016/j.foodchem.2018.06.079

Cited by 24 publications

(10 citation statements)

References 17 publications

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“…About 90% of pigments in American elderberry were cyanidin-3,5-diglycosylated (Figure 1). This glycosidic pattern is characterized by a larger l vis-max than cyanidin-3-glycosides at all pH, therefore is capable of expressing blue hues at alkaline pH [26]. Common fruit-based anthocyanin sources like European elderberry and chokeberry lack this glycosidic pattern and do not express blue hues at any pH.…”

Section: Discussionmentioning

confidence: 97%

“…This would be ascribed to its rather small fruit size [24], and tart, tangy or bitter sensory attributes brought by its abundant polyphenols contained [25]. Most anthocyanins have negligible color expression at pH ~4.5 as they transited into the colorless hemiketal form, especially for 3,5-glycosides derivatives [26]. American elderberry was abundant in 3,5-diglycosides (~90%) with a fruit pH ~4.5 (Table 1, Figure 2).…”

Section: Discussionmentioning

confidence: 99%

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Accumulation of Anthocyanins and Other Phytochemicals in American Elderberry Cultivars during Fruit Ripening and its Impact on Color Expression

Zhou

Gao

Giusti

2020

Plants

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American elderberry (Sambucus canadensis) is a plant native to North America with anthocyanin-rich fruits. Our objective was to investigate the effects of cultivar and ripeness on the phytochemical characteristics of its fruits and the corresponding color performance. Cultivars ‘Adams’, ‘Johns’, ‘Nova’, ‘Wyldewood’, and ‘York’ were examined for their °Brix, pH, anthocyanin (pH-differential method), and phenolic content (Folin-Ciocalteau method). Extract composition were analyzed by uHPLC-PDA-MS/MS. Color and spectra were determined using a plate reader. All characteristics evaluated were significantly affected by ripeness and cultivar, except for °Brix and total phenolic content, which did not vary significantly among cultivars. Most anthocyanins (63–72%) were acylated with p-coumaric acid, with cyanidin-3-(trans)-coumaroylsambubioside-5-glucoside the most predominant. The proportion of acylated anthocyanins was the only characteristic evaluated that decreased during ripening (from 80 to 70%). Extract from fully-ripened fruits exhibited red (lvis-max ~520 nm) and blue hues (lvis-max ~600 nm) at acidic and alkaline pH, respectively. Extracts from half-ripe fruit rendered yellowish tones and overall dull color. C-18 semi-purified extracts displayed higher color saturation (smaller L* and larger C*ab) than crude extracts. The vibrant and broad color expression of fully-ripened fruit extract, especially after C-18 purification, suggests this North American native plant as a promising natural colorant source.

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Section: Discussionmentioning

confidence: 97%

Section: Discussionmentioning

confidence: 99%

Accumulation of Anthocyanins and Other Phytochemicals in American Elderberry Cultivars during Fruit Ripening and its Impact on Color Expression

Zhou

Gao

Giusti

2020

Plants

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“…This may be closely related to self-association or/and an intramolecular co-pigmentation 34 . In addition, glycosylation, including mono-, di-, and tri-saccharides, generally improved the stability and water solubility of the pigment 35 ; with more stable diglycosides than their corresponding monoglycosides 36 ; at the same time, location, number, and size of glycosidic substitutions played important roles on the anthocyanins color expression 37 . These also explained why the content of rutinoside (diglycoside) in the lilac petals was much higher than those of glucoside (monoglycoside) and pigments without sugar groups.…”

Section: Discussionmentioning

confidence: 98%

Lilac (Syringa oblata) genome provides insights into its evolution and molecular mechanism of petal color change

Shi

et al. 2022

Commun Biol

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Color change during flower opening is common; however, little is understood on the biochemical and molecular basis related. Lilac (Syringa oblata), a well-known woody ornamental plant with obvious petal color changes, is an ideal model. Here, we presented chromosome-scale genome assembly for lilac, resolved the flavonoids metabolism, and identified key genes and potential regulatory networks related to petal color change. The genome assembly is 1.05 Gb anchored onto 23 chromosomes, with a BUSCO score of 96.6%. Whole-genome duplication (WGD) event shared within Oleaceae was revealed. Metabolome quantification identified delphinidin-3-O-rutinoside (Dp3Ru) and cyanidin-3-O-rutinoside (Cy3Ru) as the major pigments; gene co-expression networks indicated WRKY an essential regulation factor at the early flowering stage, ERF more important in the color transition period (from violet to light nearly white), while the MBW complex participated in the entire process. Our results provide a foundation for functional study and molecular breeding in lilac.

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“…Isoflavones are mainly found in the leguminous family of plants. Anthocyanidins in plants mainly exist in glycosidic forms, which are commonly referred to as anthocyanins [ 9 ] and are largely distributed in strawberries, blueberries, and cherries. Some polyphenols have N-containing functional substituents, such as capsaicinoids in chili peppers and avenanthramides in oats, which belong to polyphenolic amides.…”

Section: Dietary Polyphenols and Their Sourcesmentioning

confidence: 99%

Dietary Polyphenol, Gut Microbiota, and Health Benefits

2022

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Polyphenols, which are probably the most important secondary metabolites produced by plants, have attracted tremendous attention due to their health-promoting effects, including their antioxidant, anti-inflammatory, antibacterial, anti-adipogenic, and neuro-protective activities, as well as health properties. However, due to their complicated structures and high molecular weights, a large proportion of dietary polyphenols remain unabsorbed along the gastrointestinal tract, while in the large intestine they are biotransformed into bioactive, low-molecular-weight phenolic metabolites through the residing gut microbiota. Dietary polyphenols can modulate the composition of intestinal microbes, and in turn, gut microbes catabolize polyphenols to release bioactive metabolites. To better investigate the health benefits of dietary polyphenols, this review provides a summary of their modulation through in vitro and in vivo evidence (animal models and humans), as well as their possible actions through intestinal barrier function and gut microbes. This review aims to provide a basis for better understanding the relationship between dietary polyphenols, gut microbiota, and host health.

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Impact of location, type, and number of glycosidic substitutions on the color expression of o-dihydroxylated anthocyanidins

Cited by 24 publications

References 17 publications

Accumulation of Anthocyanins and Other Phytochemicals in American Elderberry Cultivars during Fruit Ripening and its Impact on Color Expression

Accumulation of Anthocyanins and Other Phytochemicals in American Elderberry Cultivars during Fruit Ripening and its Impact on Color Expression

Lilac (Syringa oblata) genome provides insights into its evolution and molecular mechanism of petal color change

Dietary Polyphenol, Gut Microbiota, and Health Benefits

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