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Oyvind M Andersen - One of the best experts on this subject based on the ideXlab platform.
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High concentrations of aromatic acylated anthocyanins found in cauline hairs in Plectranthus ciliatus.
Phytochemistry, 2016Co-Authors: Monica Jordheim, Kate E. Calcott, Kevin S. Gould, Kevin M. Davies, Kathy E. Schwinn, Oyvind M AndersenAbstract:Vegetative shoots of a naturalized population of purple-leaved plectranthus (Plectranthus ciliatus, Lamiaceae) were found to contain four main anthocyanins: Peonidin 3-(6″-caffeoyl-β-glucopyranoside)-5-β-glucopyranoside, Peonidin 3-(6″-caffeoyl-β-glucopyranoside)-5-(6‴-malonyl-β-glucopyranoside), Peonidin 3-(6″-E-p-coumaroyl-β-glucopyranoside)-5-(6‴-malonyl-β-glucopyranoside), and Peonidin 3-(6″-E-p-coumaroyl-β-glucopyranoside)-5-β-glucopyranoside. The first three of these pigments have not been reported previously from any plant. They all follow the typical anthocyanin pattern of Lamiaceae, with universal occurrence of anthocyanidin 3,5-diglucosides and aromatic acylation with p-coumaric and sometimes caffeic acids; however, they differ by being based on Peonidin. The four anthocyanins were present in the leaves (22.2 mg g(-1) DW), and in the xylem and interfascicular parenchyma of the stem. They were exceptionally abundant, among the highest reported for any plant organ, in epidermal hairs on some of the stem internodes (101 mg g(-1) DW). Anthocyanin content in these hairs increased more than three-fold from the youngest to the fourth-youngest internodes. In situ absorbances (λmax ≈ 545 nm) were bathochromic in comparison to absorbances of the isolated anthocyanins in their flavylium form in acidified aqueous solutions (λmax = 525 nm), suggesting that the anthocyanins occur both in quinoidal and flavylium forms in constant proportions in the anthocyanic hair cells. The most distinctive observation with respect to relative proportions of individual anthocyanins was found in de-haired internodes, for which anthocyanin caffeoyl-derivatives decreased, and anthocyanin coumaroyl-derivatives increased, from the youngest to the fourth-youngest internode.
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Anthocyanins of grasses
Biochemical Systematics and Ecology, 2002Co-Authors: Torgils Fossen, Rune Slimestad, Dag Olav Øvstedal, Oyvind M AndersenAbstract:Abstract The anthocyanin content of 23 grass species (Poaceae) belonging to five subfamilies has been determined. Altogether 11 anthocyanins were identified; the 3-(6″-malonylglucosides) and 3-glucosides of cyanidin, Peonidin and delphinidin, the 3-(3″,6″-dimalonylglucoside), 3-(6″-rhamnosylglucoside) and 3-(6″-glucosylglucoside) of cyanidin, in addition to Peonidin 3-(dimalonylglucoside) and delphinidin 3-(6″-rhamnosylglucoside). Anthocyanins acylated with one and/or two malonic acid moieties dominated the anthocyanin profiles of all the species in the subfamilies Pooideae and Panicoideae. On the other hand, the 3-glucoside and 3-rutinoside of cyanidin were the major anthocyanins in Sinarundinaria murielae (subfamily Bambusoideae) and Molinia caerulea (subfamily Arundinoideae), while the 3-glucosides of cyanidin and Peonidin were the principal anthocyanins in rice, Oryza sativum (subfamily Oryzoideae). Pelargonidin derivatives and free anthocyanidins have previously been reported to occur in several Poaceae species, however, not identified in any of the species included in this survey.
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Anthocyanin trisaccharides in blue berries of Vaccinium padifolium
Food Chemistry, 2000Co-Authors: Luis Cabrita, Nils Åge Frøystein, Oyvind M AndersenAbstract:Delphinidin 3-O-a-rhamnoside, malvidin 3-O-(6 00 -O-a-rhamnopyranosyl-b-glucopyranoside) and the 3-O-(6 00 -O-a-rhamnopyranosyl-2 00 -O-b-xylopyranosyl-b-glucopyranosides) of cyanidin, petunidin and Peonidin were isolated by various chromatographic techniques from the edible berries of Vaccinium padifolium. Their complete structures were elucidated mainly by one- and twodimensional nuclear magnetic resonance spectroscopy. Together they account for 7% of the anthocyanin content in this species. No anthocyanidin 3-triglycoside, 3-rutinoside or 3-rhamnoside had previously been found in the genus Vaccinium. The 3-O-(6 00 -O-arhamnopyranosyl-2 00 -O-b-xylopyranosyl-b-glucopyranosides) of petunidin and Peonidin are novel compounds. # 2000 Elsevier
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Anthocyanins in blue berries of Vaccinium padifolium
Phytochemistry, 1999Co-Authors: Luis Cabrita, Oyvind M AndersenAbstract:Abstract Twenty anthocyanins were isolated from the extract of the edible blue berries of Vaccinium padifolium (Uveira) by a combination of chromatographic techniques. Mainly on the basis of nuclear magnetic resonance techniques ( 1 H, COSY, TOCSY, HSQC, HMBC, SEFT) they were identified as the 3- O -β - glucopyranosides, 3- O -β-galactopyranosides, 3- O -β-arabinopyranosides and 3- O -sambubiosides (2″- O -β-xylopyranosyl- O -β-glucopyranosides) of delphinidin, cyanidin, petunidin, malvidin and Peonidin. Anthocyanidin disaccharides have not been identified in the genus Vaccinium previously, and the 3-sambubiosides of Peonidin, petunidin and malvidin are novel compounds.
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Anthocyanins from reproductive structures in Pinaceae
Biochemical Systematics and Ecology, 1992Co-Authors: Oyvind M AndersenAbstract:Abstract Flowers and/or cones of seven species of the family Pinaceae were subjected to qualitative and quantitative examination for anthocyanins. Cyanidin- and Peonidin-3-glucoside were found in the general Pinus, Picea and Larix . Male flowers of Picea abies contained, in addition, small amounts of delphinidin-3-glucosde (2%) and some unknown compounds (2%). Species belonging to Abies contained the 3-monoglucosides of delphinidin, petunidin, cyanidin, malvidin and Peonidin. This is the first identification of methoxylated anthocyanins in the Pinaceae, and no petunidin- or malvidin-derivative has previously been reported to occur outside the Angiospermae.
Isidro Hermosín-gutiérrez - One of the best experts on this subject based on the ideXlab platform.
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Structure elucidation of Peonidin 3,7-o-β-diglucoside isolated from Garnacha Tintorera (Vitis vinifera L.) grapes.
Journal of agricultural and food chemistry, 2010Co-Authors: Noelia Castillo-muñoz, Peter Winterhalter, Fabian Weber, M. Victoria Gomez, Sergio Gómez-alonso, Esteban García-romero, Isidro Hermosín-gutiérrezAbstract:Red wines made from Garnacha Tintorera grapes (also known as Alicante Bouschet and one of the few so-called teinturier Vitis vinifera grape cultivars, because its berry flesh is also red-colored) are usually blended with other red wines as a natural way for enhancing the color intensity of red wines. The phenolic composition of Garnacha Tintorera grapes showed already described interesting features such as the occurrence of unusual anthocyanins (pelargonidin-based anthocyanins and a Peonidin dihexoside) that had not been previously described in V. vinifera cultivars. The isolation and further structure elucidation (GC-MS analysis of sugar moieties, UV−vis, LC-MSn, and 1H and 13C NMR spectroscopic data) have allowed the identification of the aforementioned Peonidin dihexoside as Peonidin 3,7-β-O-diglucoside. This Peonidin derivative, in combination with the previously reported pelargonidin-type anthocyanins, can be suggested as a suitable chemical marker for this singular V. vinifera grape cultivar and the...
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Red-Color Related Phenolic Composition of Garnacha Tintorera (Vitis vinifera L.) Grapes and Red Wines
Journal of agricultural and food chemistry, 2009Co-Authors: Noelia Castillo-muñoz, Sergio Gómez-alonso, Esteban García-romero, M. Fernández-gonzález, Isidro Hermosín-gutiérrezAbstract:Garnacha Tintorera (also known as Alicante Bouschet) is one of the few V. vinifera grape cultivars with red-colored berry flesh. The study of the phenolic composition of both berry flesh and skin of Garnacha Tintorera grapes shows interesting findings. Anthocyanins were asymmetrically distributed within grape flesh and skins. Malvidin derivatives dominated in skin, followed by Peonidin-type anthocyanins; in contrast, the flesh almost exclusively contained Peonidin 3-glucoside. In addition, LC-UV-vis and LC-MS evidence suggest the presence of small amounts of Peonidin 3,5-diglucoside and a second Peonidin dihexoside derivative, and, very likely, the first report of the occurrence of pelargonidin 3-glucoside and its acetyl and p-coumaroyl derivatives in V. vinifera grapes. Flavonols also occurred in the flesh of Garnacha Tintorera grapes, but its flavonol profile showed lower contribution of trisubstituted flavonoid structures (myricetin, laricitrin, and syringetin) when compared to that of skin. The skin of Garnacha Tintorera grapes contained hydroxycinnamic acids in higher amounts than in flesh, caftaric acid being the main derivative found, and coutaric acid accounting for its highest proportion in the skin. The phenolic composition of the whole grape berries reflected the average of the differences described for the two aforementioned berry parts, and subsequently, the red wines made from these grapes had a phenolic composition closer to that shown by the whole berries. The formation of anthocyanin-derived pigments in Garnacha Tintorera red wines makes necessary the use of LC-MS for detecting the minor pelargonidin-based anthocyanins and Peonidin dihexoside, which could be suggested as chemical markers for cultivar authentication of this grape cultivar and its wines.
François Cormier - One of the best experts on this subject based on the ideXlab platform.
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Effects of high ammonium concentrations on growth and anthocyanin formation in grape (Vitis vinifera L.) cell suspension cultured in a production medium
Plant Cell Tissue and Organ Culture, 1991Co-Authors: Chi Bao, François CormierAbstract:Cultivating Vitis vinifera cell suspensions in a production medium which is characterized by high sucrose and low nitrate concentrations (132 mM and 6.25 mM respectively) repressed growth but enhanced the intracellular accumulation of anthocyanins, especially Peonidin 3-glucoside. Increasing the ammonium concentration of the production medium from 2 to 8–16 mM increased growth and decreased the accumulation of anthocyanins and Peonidin 3-glucoside specifically. Instead, Peonidin 3-p-coumaroylglucoside accumulated. At 24 mM ammonium concentration, growth was inhibited and accumulation of Peonidin 3-p-coumaroylglucoside was significant (p
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Accumulation of Peonidin 3-glucoside enhanced by osmotic stress in grape (Vitis vinifera L.) cell suspension
Plant Cell Tissue and Organ Culture, 1991Co-Authors: François CormierAbstract:Cell cultures of grapes, Vitis vinifera L. cv Gamay Fréaux were grown under different conditions of external osmotic potential induced by an increase of sucrose concentration or by the addition of mannitol to the culture medium. Addition of 82 mM mannitol or increasing sucrose concentration to 132 mM had similar effects on repressing growth. Cyanidin 3-glucoside, Peonidin 3-glucoside and Peonidin 3-p-coumaroylglucoside are three main anthocyanins of Vitis cells. Increasing osmotic potential from −0.43 MPa to −0.8 MPa in the medium resulted in a significant intracellular accumulation of anthocyanin especially Peonidin 3-glucoside in the pigmented cells. High osmotic potential appears to stimulate the methylation of anthocyanins. Osmotic potential is an important culture factor and may be useful in the controlling of anthocyanin production and composition.
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Accumulation of Peonidin 3-glucoside enhanced by osmotic stress in grape (Vitis vinifera L.) cell suspension
Plant Cell Tissue and Organ Culture, 1991Co-Authors: Chi Bao, François CormierAbstract:Cell cultures of grapes, Vitis vinifera L. cv Gamay Freaux were grown under different conditions of external osmotic potential induced by an increase of sucrose concentration or by the addition of mannitol to the culture medium. Addition of 82 mM mannitol or increasing sucrose concentration to 132 mM had similar effects on repressing growth. Cyanidin 3-glucoside, Peonidin 3-glucoside and Peonidin 3-p-coumaroylglucoside are three main anthocyanins of Vitis cells. Increasing osmotic potential from −0.43 MPa to −0.8 MPa in the medium resulted in a significant intracellular accumulation of anthocyanin especially Peonidin 3-glucoside in the pigmented cells. High osmotic potential appears to stimulate the methylation of anthocyanins. Osmotic potential is an important culture factor and may be useful in the controlling of anthocyanin production and composition.
Yihshou Hsieh - One of the best experts on this subject based on the ideXlab platform.
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cyanidin 3 glucoside and Peonidin 3 glucoside inhibit tumor cell growth and induce apoptosis in vitro and suppress tumor growth in vivo
Nutrition and Cancer, 2005Co-Authors: Peini Chen, Shuchen Chu, Huiling Chiou, Chuiliang Chiang, Shunfa Yang, Yihshou HsiehAbstract:Abstract: Dietary polyphenols, including anthocyanins, are suggested to be involved in the protective effects of fruits and vegetables against cancer. However, anticancer effects of Peonidin 3-glucoside have not been clearly demonstrated, with only limited studies being available concerning the inhibitory effect of cyanidin 3-glucoside for tumor cell growth. Therefore, in this study, we have isolated and identified the two bioactive compounds, Peonidin 3-glucoside and cyanidin 3-glucoside, from Oryza sativa L. indica, to treat various cancer cells. The results showed that, among analyzed cell lines, HS578T was the most sensitive to Peonidin 3-glucoside and cyanidin 3-glucoside. Treatment with Peonidin 3-glucoside or cyanidin 3-glucoside resulted in a strong inhibitory effect on cell growth via G2/M arrest. Regarding cell cycle–related proteins, Peonidin 3-glucoside treatment resulted in down-regulation of protein levels of cyclin-dependent kinase (CDK)-1, CDK-2, cyclin B1, and cyclin E, whereas cyanidin 3...
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Cyanidin 3-glucoside and Peonidin 3-glucoside inhibit tumor cell growth and induce apoptosis in vitro and suppress tumor growth in vivo.
Nutrition and Cancer, 2005Co-Authors: Peini Chen, Shuchen Chu, Huiling Chiou, Chuiliang Chiang, Shunfa Yang, Yihshou HsiehAbstract:Dietary polyphenols, including anthocyanins, are suggested to be involved in the protective effects of fruits and vegetables against cancer. However, anticancer effects of Peonidin 3-glucoside have not been clearly demonstrated, with only limited studies being available concerning the inhibitory effect of cyanidin 3-glucoside for tumor cell growth. Therefore, in this study, we have isolated and identified the two bioactive compounds, Peonidin 3-glucoside and cyanidin 3-glucoside, from Oryza sativa L. indica, to treat various cancer cells. The results showed that, among analyzed cell lines, HS578T was the most sensitive to Peonidin 3-glucoside and cyanidin 3-glucoside. Treatment with Peonidin 3-glucoside or cyanidin 3-glucoside resulted in a strong inhibitory effect on cell growth via G2/M arrest. Regarding cell cyclerelated proteins, Peonidin 3-glucoside treatment resulted in down-regulation of protein levels of cyclin-dependent kinase (CDK)-1, CDK-2, cyclin B1, and cyclin E, whereas cyanidin 3-glucoside could decrease the protein levels of CDK-1, CDK-2, cyclin B1, and cyclin D1. In addition, cyanidin 3-glucoside or Peonidin 3-glucoside also induced caspase-3 activation, chromatin condensation, and cell death. Furthermore, anthocyanins from O. sativa L. indica were evidenced by their inhibition on the growth of Lewis lung carcinoma cells in vivo.
Peter Winterhalter - One of the best experts on this subject based on the ideXlab platform.
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Structure elucidation of Peonidin 3,7-o-β-diglucoside isolated from Garnacha Tintorera (Vitis vinifera L.) grapes.
Journal of agricultural and food chemistry, 2010Co-Authors: Noelia Castillo-muñoz, Peter Winterhalter, Fabian Weber, M. Victoria Gomez, Sergio Gómez-alonso, Esteban García-romero, Isidro Hermosín-gutiérrezAbstract:Red wines made from Garnacha Tintorera grapes (also known as Alicante Bouschet and one of the few so-called teinturier Vitis vinifera grape cultivars, because its berry flesh is also red-colored) are usually blended with other red wines as a natural way for enhancing the color intensity of red wines. The phenolic composition of Garnacha Tintorera grapes showed already described interesting features such as the occurrence of unusual anthocyanins (pelargonidin-based anthocyanins and a Peonidin dihexoside) that had not been previously described in V. vinifera cultivars. The isolation and further structure elucidation (GC-MS analysis of sugar moieties, UV−vis, LC-MSn, and 1H and 13C NMR spectroscopic data) have allowed the identification of the aforementioned Peonidin dihexoside as Peonidin 3,7-β-O-diglucoside. This Peonidin derivative, in combination with the previously reported pelargonidin-type anthocyanins, can be suggested as a suitable chemical marker for this singular V. vinifera grape cultivar and the...
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preparative isolation of anthocyanins from japanese purple sweet potato ipomoea batatas l varieties by high speed countercurrent chromatography
Journal of Agricultural and Food Chemistry, 2010Co-Authors: Elyana Cuevas Montilla, Silke Hillebrand, Daniela Butschbach, Susanne Baldermann, Naoharu Watanabe, Peter WinterhalterAbstract:Purple-fleshed sweet potatoes (Ipomoea batatas L.) contain a very complex anthocyanin profile due to the presence of several non-, mono-, and diacylated glucosides of cyanidin and Peonidin. In this study, the anthocyanin composition of four Japanese purple sweet potato cultivars (Chiran Murasaki, Tanegashima Murasaki, Naka Murasaki, and Purple Sweet) were investigated by HPLC-DAD and ESI-MSn analyses. The HPLC chromatograms of the different cultivars show a remarkable variation of the two major pigments, cyanidin-3-(6′′-caffeoylsophoroside)-5-glucoside and Peonidin-3-(6′′-caffeoylsophoroside)-5-glucoside, respectively. According to this, they can be categorized into two groups on the basis of the Peonidin/cyanidin ratio: the cultivars Chiran Murasaki and Purple Sweet showed a high content of Peonidin derivatives (Peonidin type), whereas the varieties Tanegashima Murasaki and Naka Murasaki were classified as cyanidin types. By means of high-speed countercurrent chromatography (HSCCC) the nonacylated 3-soph...
