2′-Hydroxyflavylium: introducing flavanones into the flavylium network of chemical reactions

Petrov, Vesselin; Gomes, Raquel Guttierres; Parola, A. Jorge; Jesus, Alexandre; Laia, César A. T.; Piña, Fernando

doi:10.1016/j.tet.2007.11.007

Cited by 14 publications

(12 citation statements)

References 26 publications

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“…The furano ring prevents the attachment of the sugar in position 3 and the glycosylation occurs in position 2′. Synthetic flavylium compounds bearing a hydroxyl in position 2′ are able to form flavanones from the mono-anionic chalcones [ 47 ]. Another perspective for future studies would be to compare the Davies and Andersen auronidin-2′-neohesperidoside [ 10 ] with the results obtained for riccionidin A, and to identify the role of the sugar.…”

Section: Resultsmentioning

confidence: 99%

Evolution of Flavylium-Based Color Systems in Plants: What Physical Chemistry Can Tell Us

Piña

Alejo-Armijo

Clemente

et al. 2021

IJMS

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Anthocyanins are the basis of the color of angiosperms, 3-deoxyanthocyanins and sphagnorubin play the same role in mosses and ferns, and auronidins are responsible for the color in liverworts. In this study, the color system of cyanidin-3-O-glucoside (kuromanin) as a representative compound of simpler anthocyanins was fully characterized by stopped flow. This type of anthocyanin cannot confer significant color to plants without intra- or intermolecular interactions, complexation with metals or supramolecular structures as in Commelina communis. The anthocyanin’s color system was compared with those of 3-deoxyanthocyanins and riccionidin A, the aglycone of auronidins. The three systems follow the same sequence of chemical reactions, but the respective thermodynamics and kinetics are dramatically different.

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Section: Resultsmentioning

confidence: 99%

Evolution of Flavylium-Based Color Systems in Plants: What Physical Chemistry Can Tell Us

Piña

Alejo-Armijo

Clemente

et al. 2021

IJMS

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“…In Sadilova's () study, the molecular ion m/z 473 was assigned to pelargonidin chalcone glucoside, generating a typical fragment at m/z 289 (= 473‐22(Na + )‐162(glc‐H 2 O), and the signal at m/z 621 yielded the fragmentation in the MS 2 experiment, an m/z 305 ion, corresponding to the chalcone [=621‐22(Na + )‐162(glc‐H 2 O)‐132(xyl‐H 2 O)]. Chalcone has been also identified when flavylium ions in aqueous solutions (Petrov et al, ).…”

Section: Resultsmentioning

confidence: 99%

“…In addition, in another study (Furtado et al, 1993), HPLC and spectrophotometry were used to elucidate the thermal degradation of anthocyanidins, and it was found that the identified phloroglucinaldehyde originated from the A-ring of delphinidin, malvidin, pelargonidin, and cyanidin. Chalcone has been also identified when flavylium ions in aqueous solutions (Petrov et al, 2008).…”

Section: Identification Of Anthocyanidin Degradation Productsmentioning

confidence: 99%

Effects of heat, ultrasound, and microwave processing on the stability and antioxidant activity of delphinidin and petunidin

Wang

Qin

et al. 2019

J Food Biochem

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The effects of conventional heating, ultrasonic, and microwave treatments on the stability and antioxidant activities of anthocyanidin standards (delphinidin and petunidin) were studied. The antioxidant activities of delphinidin and petunidin significantly decreased during the treatments, which suggested that the antioxidant activities of the degradation products were lower than that of anthocyanidin. In addition, the degradation of delphinidin and petunidin followed first‐order reaction kinetics. The kinetic parameters indicated that delphinidin was more stable than petunidin. The microwave treatment led to the fastest degradation, followed by the conventional heating and ultrasonic treatments. Moreover, three types of degradation products of delphinidin were found by HPLC‐Q‐TOF‐MS after all three treatments, and they were phloroglucinaldehyde, delphinidin chalcone, and 3,4,5‐trihydroxybenzoic acid. Petunidin was broken into phloroglucinaldehyde, petunidin chalcone, and 3‐methoxy‐4,5‐ dihydroxybenzoic acid. Practical applications Anthocyanins with great antioxidant activity are widely distributed in plants. The stability of the anthocyanin affects its antioxidant activity and bioavailability. When anthocyanins are degraded, their antioxidant activities change accordingly. Therefore, it is crucial to study the structure, stability, and antioxidant activity of anthocyanins. This paper explores the structures and pyrolysis pathways of delphinidin and petunidin and provides basic data for the utilization and preservation of anthocyanins during food processing and production.

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“…At pH values near neutrality, the cis and the trans-chalcone deprotonate and these deprotonated species isomerize faster, not only because Cc 2 is now the major species at the pseudo-equilibrium but also the isomerization constant k9 i tends to increase. 19,22…”

Section: Resultsmentioning

confidence: 99%

“…This planarity was previously observed in other trans-29-hydroxychalcones, e.g., (E The formation of the flavanone from Ct 2 occurs only in a rather narrow pH window, 8 , pH , 10, as also reported for the compound 29-hydroxyflavylium tetrafluoroborate. 22 For pH . 10, the di-ionized species Ct 22 starts to form and this is the more stable species at higher pH values.…”

Section: Resultsmentioning

confidence: 99%

Kinetic and thermodynamic study of 2′-hydroxy-8-methoxyflavylium. Reaction network interconverting flavylium cation and flavanone

et al. 2013

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Hydroxyflavylium and 29-hydroxyflavanone derivatives can be interconverted by a precise sequence of pH jumps, through the respective intermediate (mono) ionized trans-chalcones. In acidic and neutral media, the well known network of chemical reactions involving flavylium cation, quinoidal base, hemiketal, and cis and trans chalcones is established. In the pH range 8 , pH , 10, the chalcone (Ct) deprotonates and evolves to the formation of a flavanone (F). At higher pH values, the di-ionized transchalcone is the stable species, formed from the flavylium cation. Acidification of the di-ionized transchalcone gives the flavylium cation or the flavanone, via the mono-ionized trans-chalcone, respectively at pH , 1 and pH # 9. In contrast with the chalcones, the flavanone once formed is stable even in acidic media. However, under strongly basic conditions, it leads back to the di-ionized trans-chalcone, the most stable species at more basic pH values, and the reactions leading to Ct 2 , F, Ct 22 , Ct 2 , constitute a one direction cycle for interconversion of these species.

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2′-Hydroxyflavylium: introducing flavanones into the flavylium network of chemical reactions

Cited by 14 publications

References 26 publications

Evolution of Flavylium-Based Color Systems in Plants: What Physical Chemistry Can Tell Us

Evolution of Flavylium-Based Color Systems in Plants: What Physical Chemistry Can Tell Us

Effects of heat, ultrasound, and microwave processing on the stability and antioxidant activity of delphinidin and petunidin

Kinetic and thermodynamic study of 2′-hydroxy-8-methoxyflavylium. Reaction network interconverting flavylium cation and flavanone

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