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Revision as of 13:23, 12 November 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey.← Previous edit Latest revision as of 07:01, 7 April 2024 edit undoBenbest (talk | contribs)Extended confirmed users, Pending changes reviewers10,829 edits add citation 
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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 396125754 | verifiedrevid = 440125119
| name = Chrysanthemin | Name = Chrysanthemin
| ImageFile = Cyanidin 3-O-glucoside.svg | ImageFile = Chrysanthemin_chloride.svg
| ImageSize = 300px | ImageSize = 300px
| IUPACName = <nowiki>(2S,3R,4S,5S,6R)-2-oxy-6-(hydroxymethyl)oxane-3,4,5-triol chloride</nowiki> | IUPACName = <nowiki>(2S,3R,4S,5S,6R)-2-oxy-6-(hydroxymethyl)oxane-3,4,5-triol chloride</nowiki>
| OtherNames = Chrysontenin<br>Glucocyanidin<br>Asterin<br>Chrysanthemin<br>Purple corn color<br>Kuromanin chloride<br>Cyanidin 3-glucoside<br>Cyanidol 3-glucoside<br>Cyanidine 3-glucoside<br>Cyanidin 3-O-glucoside<br>cyanidin-3-O-beta-D-glucoside<br>Cyanidin 3-monoglucoside | OtherNames = Chrysontenin<br>Glucocyanidin<br>Asterin<br>Chrysanthemin<br>Purple corn color<br>Kuromanin<br>Kuromanin chloride<br>Cyanidin 3-glucoside<br>Cyanidol 3-glucoside<br>Cyanidine 3-glucoside<br>Cyanidin 3-O-glucoside<br>cyanidin-3-O-beta-D-glucoside<br>Cyanidin 3-monoglucoside<br>C3G
| Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
⚫ | ChemSpiderID = 170681
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 170681
| 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 | 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
| InChIKey = YTMNONATNXDQJF-UBNZBFALBB | InChIKey = YTMNONATNXDQJF-UBNZBFALBB
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YTMNONATNXDQJF-UBNZBFALSA-N | StdInChIKey = YTMNONATNXDQJF-UBNZBFALSA-N
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 7084-24-4 | CASNo = 7084-24-4
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 197081
| UNII = 8X15R84UEM
⚫ | SMILES = .O(c1c(c2c(c1)c(O)cc(O)c2)c3ccc(O)c(O)c3)4O((O)(O)4O)CO
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C08604
⚫ | PubChem = 197081
⚫ | SMILES = .O(c1c(c2c(c1)c(O)cc(O)c2)c3ccc(O)c(O)c3)4O((O)(O)4O)CO
}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>21</sub>H<sub>21</sub>O<sub>11</sub><sup>+</sup>, Cl<sup>-</sup><br>C<sub>21</sub>H<sub>21</sub>ClO<sub>11</sub> | Formula = C<sub>21</sub>H<sub>21</sub>O<sub>11</sub><sup>+</sup>, Cl<sup>−</sup><br>C<sub>21</sub>H<sub>21</sub>ClO<sub>11</sub>
| MolarMass = 484.83 g/mol (chloride)<br>449.38 g/mol | MolarMass = 484.83 g/mol (chloride)<br>449.38 g/mol
| Appearance =
| ExactMass = 484.077239 (chloride)<br>449.108387
| Appearance = | Density =
| Density = | MeltingPt =
| MeltingPt = | BoilingPt =
| BoilingPt = | Solubility =
| Solubility =
}} }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}
]
'''Chrysanthemin''' is an ]. It is the 3-] of ]. It has been detected in ] pomace, ], Japanaese ],<ref>http://www.springerlink.com/content/p16q653041217g00/</ref> '']'',<ref>http://www.springerlink.com/content/nv56926774865781/</ref> ],<ref>http://www3.interscience.wiley.com/journal/113319245/abstract?CRETRY=1&SRETRY=0</ref> and ].<ref>{{cite journal |author=Del Pozo-Insfran D, Brenes CH, Talcott ST |title=Phytochemical composition and pigment stability of Açai (Euterpe oleracea Mart.) |journal=J. Agric. Food Chem. |volume=52 |issue=6 |pages=1539–45 |year=2004 |month=March |pmid=15030208 |doi=10.1021/jf035189n |url=}}</ref> The biosynthesis of cyanidin 3-O-glucoside in '']'' was demonstrated by mean of metabolic genetic engineering.<ref>{{cite journal |author=Yan Y, Chemler J, Huang L, Martens S, Koffas MA |title=Metabolic engineering of anthocyanin biosynthesis in Escherichia coli |journal=Appl. Environ. Microbiol. |volume=71 |issue=7 |pages=3617–23 |year=2005 |pmid=16000769 |doi=10.1128/AEM.71.7.3617-3623.2005}}</ref>
'''Chrysanthemin''' is an ]. It is the 3-] of ] ('''kuromanin''').<ref name="PubChem">{{cite web | title = Cyanidin 3-glucoside| work = ] | publisher = ] | url = https://pubchem.ncbi.nlm.nih.gov/compound/Cyanidin-3-glucoside | accessdate = 2024-04-07 }}</ref>


== Natural occurrences ==
⚫ ==References==
Chrysanthemin can be found in the ] (''Hibiscus sabdariffa'', Malvaceae), different Japanese ]s,<ref>{{cite journal | doi = 10.1007/BF02490176 | volume=85 | title=A survey of anthocyanins in sprouting leaves of some Japanese angiosperms studies on anthocyanins, LXV | year=1972 | journal=The Botanical Magazine Tokyo | pages=303–306 | last1 = Yoshitama | first1 = Kunijiro| issue=4 | s2cid=46453668 }}</ref> '']'' (Asteraceae),<ref>{{cite journal | doi = 10.1007/BF00565267 | volume=14 | title=Chrysanthemin and cyanin in species of the genusRhaponticum | year=1978 | journal=Chemistry of Natural Compounds | pages=450–451 | last1 = Vereskovskii | first1 = VV| issue=4 | s2cid=4817423 }}</ref> The fruits of the smooth arrowwood ('']'', Caprifoliaceae) appear blue. One of the major pigments is cyanidin 3-glucoside, but the total mixture is very complex.<ref>{{cite journal | doi = 10.1080/10408398909527503 | volume=28 | title=Food colorants: Anthocyanins | year=1989 | journal=Critical Reviews in Food Science and Nutrition | pages=273–314 | last1 = Francis | first1 = FJ | issue=4 | pmid=2690857}}</ref>

=== In food ===
Chrysanthemin has been detected in ] pomace, in ],<ref>Foods in which the polyphenol Cyanidin 3-O-glucoside is found, http://www.phenol-explorer.eu/contents/polyphenol/9</ref> in ], in ] ],<ref>{{cite journal|last1=Choung|first1=Myoung-Gun|last2=Baek|first2=In-Youl|last3=Kang|first3=Sung-Taeg|last4=Han|first4=Won-Young|last5=Doo-Chull|first5=Shin|last6=Moon|first6=Huhn-Pal|last7=Kang|first7=Kwang-Hee|title=Isolation and Determination of Anthocyanins in Seed Coats of Black Soybean (Glycine max (L.) Merr.)|journal=Journal of Agricultural and Food Chemistry|date=2001|volume=49|issue=12|pages=5848–5851|doi=10.1021/jf010550w|pmid=11743773}}</ref> in ],<ref>{{cite journal | doi = 10.1002/jsfa.2740071103 | volume=7 | title=The chemical constituents of victoria plums: Chrysanthemin, acid and pectin contents | year=1956 | journal=Journal of the Science of Food and Agriculture | pages=699–705 | last1 = Dickinson | first1 = D| issue=11 }}</ref> in ],<ref>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 ()</ref> ] and ].<ref>{{cite journal |vauthors=Del Pozo-Insfran D, Brenes CH, Talcott ST |title=Phytochemical composition and pigment stability of Açai (''Euterpe oleracea'' Mart.) |journal=J. Agric. Food Chem. |volume=52 |issue=6 |pages=1539–45 |date=March 2004 |pmid=15030208 |doi=10.1021/jf035189n }}</ref> It is found in ]s<ref>{{cite journal | pmid = 18646002 | doi=10.1002/mnfr.200700377 | volume=52 | title=Influence of glucose on cyanidin 3-glucoside absorption in rats | year=2008 | journal=Mol Nutr Food Res | pages=959–64 | last1 = Felgines | first1 = C | last2 = Texier | first2 = O | last3 = Besson | first3 = C | last4 = Vitaglione | first4 = P | last5 = Lamaison | first5 = JL | last6 = Fogliano | first6 = V | last7 = Scalbert | first7 = A | last8 = Vanella | first8 = L | last9 = Galvano | first9 = F| issue=8 }}</ref> and black rice.<ref>{{Cite journal|last1=Um|first1=Min Young|last2=Ahn|first2=Jiyun|last3=Ha|first3=Tae Youl|date=2013-09-01|title=Hypolipidaemic effects of cyanidin 3-glucoside rich extract from black rice through regulating hepatic lipogenic enzyme activities|journal=Journal of the Science of Food and Agriculture|volume=93|issue=12|pages=3126–3128|doi=10.1002/jsfa.6070|issn=1097-0010|pmid=23471845|doi-access=free}}</ref>

It is the major anthocyanin in ] (''Zea mays''). Purple corn is approved in Japan and listed in the "]" as ''purple corn color''.<ref>Anthocyanins isolated from purple corn (''Zea mays'' L.). Hiromitsu Aoki, Noriko Kuze and Yoshiaki Kato ( {{Webarchive|url=https://web.archive.org/web/20131029210237/http://www.ffcr.or.jp/zaidan/ffcrhome.nsf/7bd44c20b0dc562649256502001b65e9/c6698773361b42b249256ba60018e581/$FILE/anthocyanin-FFIJ199.pdf |date=2013-10-29 }})</ref>

== Biosynthesis ==
The biosynthesis of cyanidin 3-O-glucoside in '']'' was demonstrated by means of genetic engineering.<ref>{{cite journal |vauthors=Yan Y, Chemler J, Huang L, Martens S, Koffas MA |title=Metabolic engineering of anthocyanin biosynthesis in ''Escherichia coli'' |journal=Appl. Environ. Microbiol. |volume=71 |issue=7 |pages=3617–23 |year=2005 |pmid=16000769 |doi=10.1128/AEM.71.7.3617-3623.2005 |pmc=1169036|bibcode=2005ApEnM..71.3617Y }}</ref>

In '']'', a ], UGT79B1, is involved in the anthocyanin biosynthetic pathway. UGT79B1 protein converts cyanidin 3-O-glucoside to cyanidin 3-O-xylosyl(1→2)glucoside.<ref>{{cite journal | last1 = Yonekura-Sakakibara | first1 = Keiko | last2 = Fukushima | first2 = Atsushi | last3 = Nakabayashi | first3 = Ryo | last4 = Hanada | first4 = Kousuke | last5 = Matsuda | first5 = Fumio | last6 = Sugawara | first6 = Satoko | last7 = Inoue | first7 = Eri | last8 = Kuromori | first8 = Takashi | last9 = Ito | first9 = Takuya | last10 = Shinozaki | first10 = Kazuo | last11 = Wangwattana | first11 = Bunyapa | last12 = Yamazaki | first12 = Mami | year = 2012 | title = Two glycosyltransferases involved in anthocyanin modi?cation delineated by transcriptome independent component analysis in ''Arabidopsis thaliana'' | journal = The Plant Journal | volume = 69 | issue = 1| pages = 154–167 | doi = 10.1111/j.1365-313X.2011.04779.x | pmid = 21899608 | pmc=3507004}}</ref>

⚫ == References ==
{{Reflist}} {{Reflist}}


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