The Structure of the Major Anthocyanin in Eggplant

Sakamura, Sadao; Watanabe, Susumu; Obata, Yataro

doi:10.1271/bbb1961.27.663

Cited by 20 publications

(15 citation statements)

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“…Interestingly, the major anthocyanins detected in this study in tomato, namely nasunin and petanin, have both been identified previously in other Solanaceous species. Nasunin (also named violanin) is particularly well characterized eggplant (S. melongena; Kuroda and Wada, ; Sakamura et al ., ), as well as potato (Goto et al ., 1978), pepper (Sadilova et al ., ) and petunia (Schram et al ., ) although it is also present in Iris tingitana (Harborne, ; Nerdal and Andersen, ) and Viola tricolor (Harborne and Baxter, ), whereas petanin is particularly well characterized in petunia (Schram et al ., ), as has been described in potato, Solanum nigrum and Iris (Harborne and Baxter, ). Other anthocyanin derivatives exhibiting 3– O ‐(4′′′–phenylacyl‐rutinoside)‐5– O ‐glucoside decorations have mostly been described in Solanaceous species (petunia species, eggplant, potato and S. nigrum ), but also with additional species of iris, Ipomoea indivisia and Silene dioica (Table ).…”

Section: Resultsmentioning

confidence: 99%

“…We identified considerable alterations in a total of 113 compounds, which included seven anthocyanins and 18 flavonol derivatives. We characterized the major anthocyanins as delphinidin‐3– O‐ [4′′–( trans‐p– coumaroyl)‐α– l ‐rhamnopyranosyl‐(1→6)‐β– d ‐glucopyranoside]‐5– O ‐β– d ‐glucopyranoside (TA1, commonly referred to as nasunin and violanin) and petunidin‐3– O ‐[4′′′–( trans‐p– coumaroyl)‐α– l ‐rhamnopyranosyl‐(1→6)‐β– d ‐glucopyranoside]‐5– O ‐β– d ‐glucopyranoside (TA2, petanin), which have already been characterized in aubergine/eggplant (Kuroda and Wada, ; Sakamura et al ., ) ( Solanum melongena ) and petunia (Schram et al ., ), respectively. Integration of metabolomic and transcriptomic data allowed us to speculate about the genetic and biochemical mechanisms underlying the alterations in these profiles.…”

Section: Introductionmentioning

confidence: 99%

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Ectopic expression of snapdragon transcription factors facilitates the identification of genes encoding enzymes of anthocyanin decoration in tomato

et al. 2015

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SUMMARYGiven the potential health benefits of polyphenolic compounds in the diet, there is a growing interest in the generation of food crops enriched with health-protective flavonoids. We undertook a series of metabolite analyses of tomatoes ectopically expressing the Delila and Rosea1 transcription factor genes from snapdragon (Antirrhinum majus), paying particular attention to changes in phenylpropanoids compared to controls. These analyses revealed multiple changes, including depletion of rutin and naringenin chalcone, and enhanced levels of anthocyanins and phenylacylated flavonol derivatives. We isolated and characterized the chemical structures of the two most abundant anthocyanins, which were shown by NMR spectroscopy to be delphinidin-3-(4 000 -O-trans-p-coumaroyl)-rutinoside-5-O-glucoside and petunidin-3-(4 000 -O-trans-p-coumaroyl)-rutinoside-5-O-glucoside. By performing RNA sequencing on both purple fruit and wild-type fruit, we obtained important information concerning the relative expression of both structural and transcription factor genes. Integrative analysis of the transcript and metabolite datasets provided compelling evidence of the nature of all anthocyanin biosynthetic genes, including those encoding species-specific anthocyanin decoration enzymes. One gene, SlFdAT1 (Solyc12g088170), predicted to encode a flavonoid-3-O-rutinoside-4 000 -phenylacyltransferase, was characterized by assays of recombinant protein and overexpression assays in tobacco. The combined data are discussed in the context of both our current understanding of phenylpropanoid metabolism in Solanaceous species, and evolution of flavonoid decorating enzymes and their transcriptional networks in various plant species.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ectopic expression of snapdragon transcription factors facilitates the identification of genes encoding enzymes of anthocyanin decoration in tomato

et al. 2015

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“…The major antioxidant components of onion and eggplant are 2 types of quercetin glycosides (Tsushida & Suzuki, 1995;Price et al, 1997) and nasunin (Sakamura et al, 1963), respectively. Broccoli contains quercetin glycosides, kaempferol glycosides and 4 types of hydroxycinnamic acid esters as the major antioxidant components (Plumb et al, 1997;Price et al, 1998).…”

Section: Resultsmentioning

confidence: 99%

Radical-Scavenging Activity of Vegetables and the Effect of Coking on Their Activity.

Yamaguchi

Mizobuchi

Kajikawa

et al. 2001

FSTR

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The radical-scavenging activity of vegetables was measured using the 1,1-diphenyl-2-picrylhydrazyl-HPLC method, and the effect of cooking on this activity was determined. The content of ascorbic acid having radical-scavenging activity was highest in burdock among the 18 fresh vegetables tested. In some vegetables, the activity increased in spite of the loss of ascorbic acid content after boiling, while in other vegetables, the activity had decreased after boiling. This decrease may be due to release of the activity from cooked tissue into the cooking water during boiling. Both activity and ascorbic acid content of the vegetables cooked in a microwave were generally higher than in those cooked by boiling.

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“…Nasunin is the one isolated from eggplant (20). It is generally accepted that acylated anthocyanins are relatively more stable than nonacylated anthocyanins (23), and some acylated anthocyanins have been reported to have unique physiological functions (24,25).…”

Section: Introductionmentioning

confidence: 99%

Gastrointestinal Uptake of Nasunin, Acylated Anthocyanin in Eggplant

Ichiyanagi

Terahara

Rahman

et al. 2006

J. Agric. Food Chem.

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We previously showed that nasunin, acylated anthocyanins in eggplant peel, comprises two isomers, cis-nasunin and trans-nasunin. In this study, gastrointestinal absorption of cis- and trans-nasunins was studied in rats. Orally administered nasunins were quickly absorbed in their original acylated forms and maximally appeared in blood plasma after 15 min. When the maximum plasma concentration and area under the plasma concentration curve were normalized by orally administered dose (micromoles per kilogram), there was no significant difference in the uptake efficiency between two isomers and both exhibited a plasma level almost identical to that of delphinidin 3-O-beta-D-glucopyranoside. However, metabolites such as 4'-O-methyl analogues and extended glucuronides which were observed for delphinidin 3-O-beta-D-glucopyranoside and cyanidin 3-O-beta-D-glucopyranoside metabolisms were not detected in urine or blood plasma. Moreover, deacylated and glycolytic products of nasunins such as delphinidin 3-O-beta-D-glucopyranoside or delphinidin (aglycone) were also not detected in blood plasma even after oral administration for 8 h. These results indicated that nasunins were absorbed in their original acylated forms and exhibit a bioavailability almost identical to that of nonacylated anthocyanins.

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The Structure of the Major Anthocyanin in Eggplant

Abstract: The Structure of the Major Anthocyanin in Eggplant Sir: Kuroda and Wadan isolated a major anthocyanin in eggplant, nasunin, and proposed. its structure as delphinidin-3-diglucoside acylated with p-coumaric acid. They also re

Cited by 20 publications

References 7 publications

Ectopic expression of snapdragon transcription factors facilitates the identification of genes encoding enzymes of anthocyanin decoration in tomato

Ectopic expression of snapdragon transcription factors facilitates the identification of genes encoding enzymes of anthocyanin decoration in tomato

Radical-Scavenging Activity of Vegetables and the Effect of Coking on Their Activity.

Gastrointestinal Uptake of Nasunin, Acylated Anthocyanin in Eggplant

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