Chrysanthemin

Chrysanthemin
Nombre IUPAC
	(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol chloride
General
Otros nombres	Chrysontenina; Glucocyanidina; Asterina; Chrysanthemina; Purple corn color; Kuromanina chloride; Cianidina 3-glucósida; Cyanidol 3-glucoside; Cyanidine 3-glucoside; Cyanidin 3-O-glucoside; cyanidin-3-O-beta-D-glucoside; Cyanidin 3-monoglucoside
Fórmula molecular	C21H21O11+, Cl-; C21H21ClO11
Identificadores
Número CAS	7084-24-4
ChemSpider	170681
PubChem	197081
UNII	8X15R84UEM
KEGG	C08604
	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
	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
Propiedades físicas
Masa molar	484.83 g/mol (chloride); 449.38 g/mol g/mol
	Valores en el SI y en condiciones estándar; (25 ℃ y 1 atm), salvo que se indique lo contrario.
	[editar datos en Wikidata]

Chrysanthemin es una antocianina. Es el 3-glucósido de cianidina.

Producción natural

Chrysanthemin se puede encontrar en la planta (Hibiscus sabdariffa, Malvaceae), diferentes angiospermas japoneses,^[2] Rhaponticum (Asteraceae),^[3] Los frutos de (Viburnum dentatum, Caprifoliaceae) aparecen de color azul. Uno de los principales pigmentos es cyanidin 3-glucósido, pero la mezcla total es muy compleja.^[4]

En los alimentos

Chrysanthemin se ha detectado en el orujo de la grosella negra, y en el saúco europeo,^[5] en las frambuesas rojas, en Prunus domestica,^[6] en el melocotón,^[7] lichi y açaí.^[8] Es la principal antocianina en Zea mays.^[9]

Biosíntesis

La biosíntesis de cianidina 3-O-glucósido en Escherichia coli se demostró por medio de la ingeniería genética metabólica.^[10]

En Arabidopsis thaliana, una glicosiltransferasa, UGT79B1, está implicada en la ruta biosintética de la antocianina. La proteína UGT79B1 convierte cianidina 3-O-glucósido de cyanidin 3-O-xylosyl(1→2)glucósido.^[11]

Referencias

↑ Número CAS
↑ "A survey of anthocyanins in sprouting leaves of some Japanese angiosperms studies on anthocyanins, LXV". Kunijiro Yoshitama, Makiko Ozaku, Michiko Hujii and Kôzô Hayashi, Journal of plant research, Volume 85, Number 4, pages 303–306, doi 10.1007/BF02490176
↑ "Chrysanthemin and cyanin in species of the genus Rhaponticum. V. V. Vereskovskii and I. I. Chekalinskaya, Chemistry of natural compounds, Volume 14, Number 4, pages 450–451, doi 10.1007/BF00565267
↑ "Food colorants: Anthocyanins". F. J. Francis and Pericles C. Markakis, Critical Reviews in Food Science and Nutrition, 1989, Volume 28, Issue 4, pages 273–314, doi 10.1080/10408398909527503
↑ Foods in which the polyphenol Cyanidin 3-O-glucoside is found, http://www.phenol-explorer.eu/contents/polyphenol/9
↑ The chemical constituents of victoria plums: Chrysanthemin, acid and pectin contents. D. Dickinson and Joy H. Gawler, Journal of the Science of Food and Agriculture, Volume 7, Issue 11, November 1956, pp. 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 (marzo de 2004). «Phytochemical composition and pigment stability of Açai (Euterpe oleracea Mart.)». J. Agric. Food Chem. 52 (6): 1539-45. PMID 15030208. doi:10.1021/jf035189n.
↑ Anthocyanins isolated from purple corn (Zea mays L.). Hiromitsu Aoki, Noriko Kuze and Yoshiaki Kato (article Archivado el 29 de octubre de 2013 en 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. PMC 1169036. PMID 16000769. doi:10.1128/AEM.71.7.3617-3623.2005.
↑ "Two glycosyltransferases involved in anthocyanin modiﬁcation delineated by transcriptome independent component analysis in Arabidopsis thaliana". Keiko Yonekura-Sakakibara, Atsushi Fukushima, Ryo Nakabayashi1, Kousuke Hanada, Fumio Matsuda, Satoko Sugawara, Eri Inoue, Takashi Kuromori, Takuya Ito, Kazuo Shinozaki, Bunyapa Wangwattana and Mami Yamazaki, The Plant Journal, 2012, volume 69, pages 154–167, doi 10.1111/j.1365-313X.2011.04779.x

Enlaces externos

Esta obra contiene una traducción derivada de «Chrysanthemin» de Wikipedia en inglés, publicada por sus editores bajo la Licencia de documentación libre de GNU y la Licencia Creative Commons Atribución-CompartirIgual 4.0 Internacional.

Datos: Q5114535

[1] Número CAS

[2] "A survey of anthocyanins in sprouting leaves of some Japanese angiosperms studies on anthocyanins, LXV". Kunijiro Yoshitama, Makiko Ozaku, Michiko Hujii and Kôzô Hayashi, Journal of plant research, Volume 85, Number 4, pages 303–306, doi 10.1007/BF02490176

[3] "Chrysanthemin and cyanin in species of the genus Rhaponticum. V. V. Vereskovskii and I. I. Chekalinskaya, Chemistry of natural compounds, Volume 14, Number 4, pages 450–451, doi 10.1007/BF00565267

[4] "Food colorants: Anthocyanins". F. J. Francis and Pericles C. Markakis, Critical Reviews in Food Science and Nutrition, 1989, Volume 28, Issue 4, pages 273–314, doi 10.1080/10408398909527503

[5] Foods in which the polyphenol Cyanidin 3-O-glucoside is found, http://www.phenol-explorer.eu/contents/polyphenol/9

[6] The chemical constituents of victoria plums: Chrysanthemin, acid and pectin contents. D. Dickinson and Joy H. Gawler, Journal of the Science of Food and Agriculture, Volume 7, Issue 11, November 1956, pp. 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 (marzo de 2004). «Phytochemical composition and pigment stability of Açai (Euterpe oleracea Mart.)». J. Agric. Food Chem. 52 (6): 1539-45. PMID 15030208. doi:10.1021/jf035189n.

[9] Anthocyanins isolated from purple corn (Zea mays L.). Hiromitsu Aoki, Noriko Kuze and Yoshiaki Kato (article Archivado el 29 de octubre de 2013 en Wayback Machine.)

[10] 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. PMC 1169036. PMID 16000769. doi:10.1128/AEM.71.7.3617-3623.2005.

[11] "Two glycosyltransferases involved in anthocyanin modiﬁcation delineated by transcriptome independent component analysis in Arabidopsis thaliana". Keiko Yonekura-Sakakibara, Atsushi Fukushima, Ryo Nakabayashi1, Kousuke Hanada, Fumio Matsuda, Satoko Sugawara, Eri Inoue, Takashi Kuromori, Takuya Ito, Kazuo Shinozaki, Bunyapa Wangwattana and Mami Yamazaki, The Plant Journal, 2012, volume 69, pages 154–167, doi 10.1111/j.1365-313X.2011.04779.x

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