A novel symmetrical pyrano-3-deoxyanthocyanidin from a Sorghum species

Khalil, Ali Talha; Baltenweck, Raymonde; Ocampo-Torres, R.; Albrecht, Pierre

doi:10.1016/j.phytol.2010.02.003

Cited by 33 publications

(27 citation statements)

References 13 publications

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“…3,4,10 In contrast to previous reports, 24 pyrano-3-deoxyanthocyanidins were not identified in unfermented sorghum. We employed pure cultivar sorghum grains that were milled just prior to fermentation, thus minimizing the potential of chemical, microbial, or enzymatic conversions prior to extraction.…”

Section: ■ Discussioncontrasting

confidence: 95%

“…22,23 The remaining compounds, 6,8,10,13,14,15, and 20, could not be identified with external standards or published mass spectra, although the molecular mass of compound 13 matched the mass of pyrano-3-apigeninidin 4-vinylphenol. 24 Deoxyanthocyanidin adducts were identified exclusively in sorghum sourdoughs. The relative quantitation of deoxyanthocyanidins in sorghum sourdoughs based on the peak height at 480 nm revealed that the pattern of deoxyanthocyanidins remained essentially unchanged in chemically acidified dough.…”

Section: Conversion Of 3-deoxyanthocyanidins In Sorghummentioning

confidence: 98%

“…24 The structure and peak assignments of compound 13 are also shown in Table 3. Under IUPAC naming conventions, compound 8 is 6-(1-(4-hydroxyphenyl)ethyl)-apigeninidin chloride and compound 13 is 8-hydroxy-2(4′-hydroxyphenyl)-5(4″-hydroxyphenyl)pyrano[4,3,2-de]1-benzopyrylium chloride.…”

Section: Conversion Of 3-deoxyanthocyanidins In Sorghummentioning

confidence: 99%

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Novel Pyrano and Vinylphenol Adducts of Deoxyanthocyanidins in Sorghum Sourdough

Bai

Findlay

Maldonado

et al. 2014

J. Agric. Food Chem.

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This study determined the fate of deoxyanthocyanidins in sorghum sourdoughs. Sourdoughs prepared from the red sorghum variety Town were fermented with the caffeic acid-decarboxylating strains Lactobacillus plantarum FUA3171 and the decarboxylase negative L. casei FUA3166. Deoxyanthocyanidins were analyzed by liquid chromatography-tandem mass spectrometry (LC-MS/MS). Apigeninidin and methoxyapigeninidin were the major deoxyanthocyanidins prior to fermentation. During fermentation, novel deoxyanthocyanidins were formed. Purification by preparative LC, followed by NMR analysis and high-resolution MS identified two of the compounds as 6-deoxyanthocyanidin-vinylphenol and pyrano-3-deoxyanthocyanidin. To identify pathways for their formation, sorghum was fermented with single strains, L. plantarum or L. casei. 6-Deoxyanthocyanidin-vinylphenol and pyrano-3-deoxyanthocyanidin were formed only during fermentation with L. plantarum FUA3171, indicating a role of vinylphenol in their formation. Chemical synthesis confirmed that 6-deoxyanthocyanidin-vinylphenol and pyrano-3-deoxyanthocyanidin are formed from apigeninidin with vinylphenol but not with p-coumaric acid as reactants. In conclusion, the products of microbial decarboxylation of hydroxycinnamic acids convert apigeninidin and methoxyapigeninidin to pyrano-3-deoxyanthocyanidins and vinylphenol adducts.

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Section: ■ Discussioncontrasting

confidence: 95%

Section: Conversion Of 3-deoxyanthocyanidins In Sorghummentioning

confidence: 98%

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Novel Pyrano and Vinylphenol Adducts of Deoxyanthocyanidins in Sorghum Sourdough

Bai

Findlay

Maldonado

et al. 2014

J. Agric. Food Chem.

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“…Their derivatives including the methoxylated form (7‐methoxy‐apigeninidin, 7‐methoxy‐luteolinidin, and 5‐methoxy‐luteolinidin), glycosides (apigeninidin 5‐glucoside and luteolinidin 5‐glucoside), and methoxylated glycosides (7‐methoxy‐apigeninidin 5‐glucoside, 7‐methoxy‐luteolinidin 5‐glucoside, and 5‐methoxy‐luteolinidin 7‐glucoside) have also been reported and in relatively moderate or small quantities (Dykes et al., ; Dykes et al., ; Petti et al., ; Wu & Prior, ). Moreover, other novel derivatives such as dimeric 3‐deoxyanthocyanidins (for example, apigeninidin‐flavene dimer) and pyranic 3‐deoxyanthocyanidins (an additional ring connected to the C‐4 and C‐5 position) have also been reported and demonstrated promising color stability (Bai et al., ; Geera, Ojwang, & Awika, ; Khalil, Baltenweck‐Guyot, Ocampo‐Torres, & Albrecht, ).…”

Section: Sorghum Grain Bioactive Phenolic Compoundsmentioning

confidence: 99%

Sorghum Grain: From Genotype, Nutrition, and Phenolic Profile to Its Health Benefits and Food Applications

Xiong

Zhang

Warner

et al. 2019

Comp Rev Food Sci Food Safe

216

127

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Globally, sorghum is one of the most important but least utilized staple crops. Sorghum grain is a rich source of nutrients and health‐beneficial phenolic compounds. The phenolic profile of sorghum is exceptionally unique and more abundant and diverse than other common cereal grains. The phenolic compounds in sorghum are mainly composed of phenolic acids, 3‐deoxyanthocyanidins, and condensed tannins. Studies have shown that sorghum phenolic compounds have potent antioxidant activity in vitro, and consumption of sorghum whole grain may improve gut health and reduce the risks of chronic diseases. Recently, sorghum grain has been used to develop functional foods and beverages, and as an ingredient incorporated into other foods. Moreover, the phenolic compounds, 3‐deoxyanthocyanidins, and condensed tannins can be isolated and used as promising natural multifunctional additives in broad food applications. The objective of this review is to provide a comprehensive understanding of nutrition and phenolic compounds derived from sorghum and their related health effects, and demonstrate the potential for incorporation of sorghum in food systems as a functional component and food additive to improve food quality, safety, and health functions.

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“…Pyrano‐3‐deoxyanthocyanidin has an additional fourth pyranic ring that enhances electron delocalization of the system which makes it more stable against pH variations and bleaching by SO 2 than its homologous 3‐deoxyanthocyanidins and anthocyanins (Sousa et al., ). A symmetrical pyrano‐3‐deoxyanthocyanidin, that is, pyrano‐apigeninidin 4‐vinylphenol, was also recently isolated from red sorghum (Khalil et al., ).…”

Section: Chemical Synthesismentioning

confidence: 99%

3‐Deoxyanthocyanidin Colorant: Nature, Health, Synthesis, and Food Applications

Xiong

Zhang

Warner

et al. 2019

Comp Rev Food Sci Food Safe

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3‐Deoxyanthocyanidins are a rare type of anthocyanins that are present in mosses, ferns, and some flowering plants. They are water‐soluble pigments and impart orange‐red and blue‐violet color to plants and play a role as phytoalexins against microbial infection and environmental stress. In contrast to anthocyanins, the lack of a hydroxyl group at the C‐3 position confers unique chemical and biochemical properties. They are potent natural antioxidants with a number of potential health benefits including cancer prevention. 3‐Deoxyanthocyanidin pigments have attracted much attention in the food industry as natural food colorants, mainly due to their higher stability during processing and handling conditions compared with anthocyanins. They are also photochromic compounds capable of causing a change in “perceived” color, when exposed to UV light, which can be used to design novel foods and beverages. Due to their interesting properties and potential industrial applications, great efforts have been made to synthesize these compounds. For biosynthesis, researchers have discovered the 3‐deoxyanthocyanidin biosynthetic pathway and their biosynthetic genes. For chemical synthesis, advances have been made to synthesize the compounds in a simpler and more efficient way as well as looking for its novel derivative with enhanced coloration properties. This review summarizes the developments in the research on 3‐deoxyanthocyanidin as a colorant, from natural sources to chemical syntheses and from health benefits to applications and future prospects, providing comprehensive insights into this group of interesting compounds.

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A novel symmetrical pyrano-3-deoxyanthocyanidin from a Sorghum species

Cited by 33 publications

References 13 publications

Novel Pyrano and Vinylphenol Adducts of Deoxyanthocyanidins in Sorghum Sourdough

Novel Pyrano and Vinylphenol Adducts of Deoxyanthocyanidins in Sorghum Sourdough

Sorghum Grain: From Genotype, Nutrition, and Phenolic Profile to Its Health Benefits and Food Applications

3‐Deoxyanthocyanidin Colorant: Nature, Health, Synthesis, and Food Applications

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