Chrysanthemin
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IUPAC name (2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol chloride | |
Other names Chrysontenin Glucocyanidin Asterin Chrysanthemin Purple corn color Kuromanin Kuromanin chloride Cyanidin 3-glucoside Cyanidol 3-glucoside Cyanidine 3-glucoside Cyanidin 3-O-glucoside cyanidin-3-O-beta-D-glucoside Cyanidin 3-monoglucoside C3G | |
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ChemSpider |
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ECHA InfoCard | 100.027.622 |
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InChI
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Properties | |
Chemical formula | C21H21O11+, Cl− C21H21ClO11 |
Molar mass | 484.83 g/mol (chloride) 449.38 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references |
Chrysanthemin is an anthocyanin. It is the 3-glucoside of cyanidin (kuromanin).[1]
Natural occurrences
Chrysanthemin can be found in the roselle plant (Hibiscus sabdariffa, Malvaceae), different Japanese angiosperms,[2] Rhaponticum (Asteraceae),[3] The fruits of the smooth arrowwood (Viburnum dentatum, Caprifoliaceae) appear blue. One of the major pigments is cyanidin 3-glucoside, but the total mixture is very complex.[4]
In food
Chrysanthemin has been detected in blackcurrant pomace, in European elderberry,[5] in red raspberries, in soybean seed coats,[6] in Victoria plum,[7] in peach,[8] lychee and açaí.[9] It is found in red oranges[10] and black rice.[11]
It is the major anthocyanin in purple corn (Zea mays). Purple corn is approved in Japan and listed in the "Existing Food Additive List" as purple corn color.[12]
Biosynthesis
The biosynthesis of cyanidin 3-O-glucoside in Escherichia coli was demonstrated by means of genetic engineering.[13]
In Arabidopsis thaliana, a glycosyltransferase, UGT79B1, is involved in the anthocyanin biosynthetic pathway. UGT79B1 protein converts cyanidin 3-O-glucoside to cyanidin 3-O-xylosyl(1→2)glucoside.[14]
References
- ^ "Cyanidin 3-glucoside". PubChem. United States National Library of Medicine. Retrieved 2024-04-07.
- ^ Yoshitama, Kunijiro (1972). "A survey of anthocyanins in sprouting leaves of some Japanese angiosperms studies on anthocyanins, LXV". The Botanical Magazine Tokyo. 85 (4): 303–306. doi:10.1007/BF02490176. S2CID 46453668.
- ^ Vereskovskii, VV (1978). "Chrysanthemin and cyanin in species of the genusRhaponticum". Chemistry of Natural Compounds. 14 (4): 450–451. doi:10.1007/BF00565267. S2CID 4817423.
- ^ Francis, FJ (1989). "Food colorants: Anthocyanins". Critical Reviews in Food Science and Nutrition. 28 (4): 273–314. doi:10.1080/10408398909527503. PMID 2690857.
- ^ Foods in which the polyphenol Cyanidin 3-O-glucoside is found, http://www.phenol-explorer.eu/contents/polyphenol/9
- ^ Choung, Myoung-Gun; Baek, In-Youl; Kang, Sung-Taeg; Han, Won-Young; Doo-Chull, Shin; Moon, Huhn-Pal; Kang, Kwang-Hee (2001). "Isolation and Determination of Anthocyanins in Seed Coats of Black Soybean (Glycine max (L.) Merr.)". Journal of Agricultural and Food Chemistry. 49 (12): 5848–5851. doi:10.1021/jf010550w. PMID 11743773.
- ^ Dickinson, D (1956). "The chemical constituents of victoria plums: Chrysanthemin, acid and pectin contents". Journal of the Science of Food and Agriculture. 7 (11): 699–705. doi:10.1002/jsfa.2740071103.
- ^ Postharvest sensory and phenolic characterization of 'Elegant Lady and 'Carson' peaches. Rodrigo Infante, Loreto Contador, Pía Rubio, Danilo Aros and Álvaro Peña-Neira, Chilean Journal of Agricultural Research, 71(3), July–September 2011, pages 445–451 (article)
- ^ Del Pozo-Insfran D, Brenes CH, Talcott ST (March 2004). "Phytochemical composition and pigment stability of Açai (Euterpe oleracea Mart.)". J. Agric. Food Chem. 52 (6): 1539–45. doi:10.1021/jf035189n. PMID 15030208.
- ^ Felgines, C; Texier, O; Besson, C; Vitaglione, P; Lamaison, JL; Fogliano, V; Scalbert, A; Vanella, L; Galvano, F (2008). "Influence of glucose on cyanidin 3-glucoside absorption in rats". Mol Nutr Food Res. 52 (8): 959–64. doi:10.1002/mnfr.200700377. PMID 18646002.
- ^ Um, Min Young; Ahn, Jiyun; Ha, Tae Youl (2013-09-01). "Hypolipidaemic effects of cyanidin 3-glucoside rich extract from black rice through regulating hepatic lipogenic enzyme activities". Journal of the Science of Food and Agriculture. 93 (12): 3126–3128. doi:10.1002/jsfa.6070. ISSN 1097-0010. PMID 23471845.
- ^ Anthocyanins isolated from purple corn (Zea mays L.). Hiromitsu Aoki, Noriko Kuze and Yoshiaki Kato (article Archived 2013-10-29 at the Wayback Machine)
- ^ Yan Y, Chemler J, Huang L, Martens S, Koffas MA (2005). "Metabolic engineering of anthocyanin biosynthesis in Escherichia coli". Appl. Environ. Microbiol. 71 (7): 3617–23. Bibcode:2005ApEnM..71.3617Y. doi:10.1128/AEM.71.7.3617-3623.2005. PMC 1169036. PMID 16000769.
- ^ Yonekura-Sakakibara, Keiko; Fukushima, Atsushi; Nakabayashi, Ryo; Hanada, Kousuke; Matsuda, Fumio; Sugawara, Satoko; Inoue, Eri; Kuromori, Takashi; Ito, Takuya; Shinozaki, Kazuo; Wangwattana, Bunyapa; Yamazaki, Mami (2012). "Two glycosyltransferases involved in anthocyanin modi?cation delineated by transcriptome independent component analysis in Arabidopsis thaliana". The Plant Journal. 69 (1): 154–167. doi:10.1111/j.1365-313X.2011.04779.x. PMC 3507004. PMID 21899608.
- v
- t
- e
- 5-Desoxy-peonidin
- Aurantinidin
- Cyanidin
- 6-Hydroxycyanidin
- Delphinidin
- Fisetinidin
- Guibourtinidin
- Pelargonidin
- Robinetinidin
- 5-Desoxy-malvidin
- Capensinidin
- Europinidin
- Hirsutidin
- Kaempferidinidin
- Malvidin
- Peonidin
- Petunidin
- Pulchellidin
- Rosinidin
(anthocyaninidin glycosides)
- Callistephin (Pelargonidin 3-O-glucoside)
- Chrysanthemin (Cyanidin 3-O-glucoside)
- Myrtillin (Delphinidin 3-O-glucoside)
- Oenin (Malvidin 3-O-glucoside)
- Peonidin 3-O-glucoside
- Petunidin 3-O-glucoside
- Pulchellidin 3-glucoside
Diglucosides:
- Cyanin (Cyanidin 3,5-O-diglucoside)
- Delphin (Delphinidin 3,5-O-diglucoside)
- Malvin (Malvidin 3,5-diglucoside)
- Pelargonin (Pelargonidin 3,5-O-diglucoside)
- Peonin (Peonidin 3,5-O-diglucoside)
- Petunin (Petunidin 3,5-O-diglucoside)
Others glycosides:
- Antirrhinin (Cyanidin 3-O-rutinoside)
- Ideain (Cyanidin 3-O-galactoside)
- Delphinidin 3-O-rhamnoside
- Petunidin 3-O-arabinoside
- Petunidin 3-O-galactoside
- Petunidin 3-O-rhamnoside
- Petunidin 3-O-rutinoside
- Primulin (Malvidin 3-O-galactoside)
- Pulchellidin 3-rhamnoside
- Tulipanin (Delphinidin 3-O-rutinoside)
Acetylated anthocyanins | |
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Coumaroylated anthocyanins (cis- and trans-) |
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Caffeoylated anthocyanins |
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Malonylated anthocyanins |
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Acylated anthocyanin diglycosides |
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- Malvidin glucoside-ethyl-catechin
- Catechin(4α→8)pelargonidin 3-O-β-glucopyranoside
- Epicatechin(4α→8)pelargonidin 3-O-β-glucopyranoside
- Afzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
- Epiafzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
- Metalloanthocyanins (commelinin)
- Cyanosalvianin
- Protocyanin
- Protodelphin)
- Pyranoanthocyanins
- Copigmentation
- Anthocyanone A (degradation product of oenin)
- Malvone (oxidation product of malvin)