Chrysanthemin

Chrysanthemin is an anthocyanin. It is the 3-glucoside of cyanidin.

Chrysanthemin

Names
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
Identifiers
CAS Number	7084-24-4
3D model (JSmol)	Interactive image
ChemSpider	170681
ECHA InfoCard	100.027.622
PubChem CID	197081
UNII	8X15R84UEM
InChI InChI=1S/C21H20O11.ClH/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8;/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26);1H/t16-,17-,18+,19-,21-;/m1./s1 Key: YTMNONATNXDQJF-UBNZBFALSA-N InChI=1/C21H20O11.ClH/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8;/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26);1H/t16-,17-,18+,19-,21-;/m1./s1 Key: YTMNONATNXDQJF-UBNZBFALBB
SMILES [Cl-].O(c1c([o+]c2c(c1)c(O)cc(O)c2)c3ccc(O)c(O)c3)[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)CO
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).
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Infobox references

UV visible spectrum of cyanidin 3-O-glucoside

Natural occurrences

Chrysanthemin can be found in the roselle plant (Hibiscus sabdariffa, Malvaceae), different Japanese angiosperms,[1] Rhaponticum (Asteraceae),[2] 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.[3]

In food

Chrysanthemin has been detected in blackcurrant pomace, in European elderberry,[4] in red raspberries, in soybean seed coats,[5] in Victoria plum,[6] in peach,[7] lychee and açaí.[8] It is found in red oranges[9] and black rice.[10]

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.[11]

Biosynthesis

The biosynthesis of cyanidin 3-O-glucoside in Escherichia coli was demonstrated by means of genetic engineering.[12]

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.[13]

References

1. Yoshitama, Kunijiro (1972). "A survey of anthocyanins in sprouting leaves of some Japanese angiosperms studies on anthocyanins, LXV". The Botanical Magazine Tokyo. 85: 303–306. doi:10.1007/BF02490176.
2. Vereskovskii, V. V. (1978). "Chrysanthemin and cyanin in species of the genusRhaponticum". Chemistry of Natural Compounds. 14: 450–451. doi:10.1007/BF00565267.
3. Francis, F.J. (1989). "Food colorants: Anthocyanins". Critical Reviews in Food Science and Nutrition. 28: 273–314. doi:10.1080/10408398909527503. PMID 2690857.
4. Foods in which the polyphenol Cyanidin 3-O-glucoside is found, http://www.phenol-explorer.eu/contents/polyphenol/9
5. 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.
6. Dickinson, D. (1956). "The chemical constituents of victoria plums: Chrysanthemin, acid and pectin contents". Journal of the Science of Food and Agriculture. 7: 699–705. doi:10.1002/jsfa.2740071103.
7. 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)
8. 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.
9. 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: 959–64. doi:10.1002/mnfr.200700377. PMID 18646002.
10. 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.
11. Anthocyanins isolated from purple corn (Zea mays L.). Hiromitsu Aoki, Noriko Kuze and Yoshiaki Kato (article Archived 2013-10-29 at the Wayback Machine)
12. 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. doi:10.1128/AEM.71.7.3617-3623.2005. PMC 1169036. PMID 16000769.
13. 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.