Laricitrin: Difference between revisions

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-{{chembox
+{{Chembox
+| Verifiedfields = changed
-| verifiedrevid = 423617613
+| Watchedfields = changed
+| verifiedrevid = 449562314
 | Name = Laricitrin
-| ImageFile = Laricitrin.PNG
+| ImageFile = Laricitrin.svg
-| ImageSize = 200px
 | ImageName = Chemical structure of laricitrin
-| IUPACName =
+| IUPACName = 3,3′,4′,5,7-Pentahydroxy-5′-methoxyflavone
+| SystematicName = 2-(3,4-Dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-4''H''-1-benzopyran-4-one
-| OtherNames = 3'-O-Methylmyricetin<!-- <br> -->
+| OtherNames = 3'-''O''-Methylmyricetin
-|Section1= {{Chembox Identifiers
+|Section1={{Chembox Identifiers
+| CASNo_Ref = {{cascite|correct|??}}
 | CASNo = 53472-37-0
+| UNII_Ref = {{fdacite|correct|FDA}}
-| CASNo_Ref =
-| CASOther =
+| UNII = JQZ2DUC4C9
+| ChEBI_Ref = {{ebicite|changed|EBI}}
+| ChEBI = 31763
+| CASNoOther =
 | PubChem = 5282154
+| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
-| SMILES = Oc1c(O)cc(cc1OC)-c3oc(c2c(=O)c3O)cc(O)cc2O
-| InChI =
+| ChemSpiderID = 4445351
+| SMILES = O=C1c3c(O/C(=C1/O)c2cc(O)c(O)c(OC)c2)cc(O)cc3O
+| InChI = 1/C16H12O8/c1-23-11-3-6(2-9(19)13(11)20)16-15(22)14(21)12-8(18)4-7(17)5-10(12)24-16/h2-5,17-20,22H,1H3
+| InChIKey = CFYMYCCYMJIYAB-UHFFFAOYAK
+| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
+| StdInChI = 1S/C16H12O8/c1-23-11-3-6(2-9(19)13(11)20)16-15(22)14(21)12-8(18)4-7(17)5-10(12)24-16/h2-5,17-20,22H,1H3
+| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
+| StdInChIKey = CFYMYCCYMJIYAB-UHFFFAOYSA-N
+| RTECS =
 | MeSHName =
+| KEGG_Ref = {{keggcite|changed|kegg}}
-}}
+| KEGG = C12633
-|Section2= {{Chembox Properties
+ }}
-| Formula = C<sub>16</sub>H<sub>12</sub>O<sub>8</sub>
+|Section2={{Chembox Properties
-| MolarMass = 332.26 g/mol
+| C=16 | H=12 | O=8
-| ExactMass = 332.053217 u
 | Appearance =
 | Density =
-| MeltingPt = <!-- °C -->
+| MeltingPt =
-| BoilingPt = <!-- °C -->
+| BoilingPt =
 | Solubility =
+ }}
 }}
-}}
-'''Laricitrin''' is a [[O-methylated flavonol]], a type of flavonoid. It is found in [[Red grape variety|red grape]] (absent in white grape)<ref name=Mattivi>[http://pubs.acs.org/doi/abs/10.1021/jf061538c Metabolite Profiling of Grape: Flavonols and Anthocyanins. Fulvio Mattivi, Raffaele Guzzon, Urska Vrhovsek, Marco Stefanini and Riccardo Velasco, J. Agric. Food Chem., 2006, 54 (20), pp 7692–7702]</ref> and in ''[[Vaccinium uliginosum]]'' (bog billberries).<ref>[http://pubs.acs.org/doi/abs/10.1021/jf903033m Anthocyanin and Flavonol Variation in Bog Bilberries (Vaccinium uliginosum L.) in Finland. Anja K. Lätti, Laura Jaakola, Kaisu R. Riihinen and Pirjo S. Kainulainen, J. Agric. Food Chem., 2010, 58 (1), pp 427–433]</ref> It is one of the [[Phenolic compounds in wine|phenolic compounds present in wine]].<ref>[http://cat.inist.fr/?aModele=afficheN&cpsidt=18502213 Flavonol profiles of Vitis vinifera red grapes and their single-cultivar wines. Castillo-Munoz Noelia, Gomez-Alonso Sergio, Garcia-Romero Esteban and Hermosin-Gutierrez Isidro, Journal of agricultural and food chemistry, 2007, vol. 55, no3, pp. 992-1002]</ref>
+'''Laricitrin''' is an [[O-methylated flavonol|''O''-methylated flavonol]], a type of flavonoid. It is found in [[Red grape variety|red grape]] (absent in white grape)<ref name=Mattivi>{{cite journal|doi=10.1021/jf061538c | pmid=17002441 | volume=54 | title=Metabolite profiling of grape: Flavonols and anthocyanins | date=October 2006 | journal=J. Agric. Food Chem. | pages=7692–702 | last1 = Mattivi | first1 = F | last2 = Guzzon | first2 = R | last3 = Vrhovsek | first3 = U | last4 = Stefanini | first4 = M | last5 = Velasco | first5 = R| issue=20 }}</ref> and in ''[[Vaccinium uliginosum]]'' (bog bilberries).<ref>{{cite journal|doi=10.1021/jf903033m | volume=58 | title=Anthocyanin and Flavonol Variation in Bog Bilberries (Vaccinium uliginosumL.) in Finland | year=2010 | journal=Journal of Agricultural and Food Chemistry | pages=427–433 | last1 = Anja | last2 = Jaakola | first2 = Laura | last3 = Riihinen | first3 = Kaisu R. | last4 = Kainulainen | first4 = Pirjo S. | issue=1 | pmid = 20000402}}</ref> It is one of the [[Phenolic compounds in wine|phenolic compounds present in wine]].<ref>{{cite journal | first1 = Noelia | last1 = Castillo-Munoz | first2 = Sergio | last2 = Gomez-Alonso | first3 = Esteban | last3 = Garcia-Romero | first4 = Isidro | last4 = Hermosin-Gutierrez | year = 2007 | title = Flavonol profiles of Vitis vinifera red grapes and their single-cultivar wines | url = http://cat.inist.fr/?aModele=afficheN&cpsidt=18502213 | journal = Journal of Agricultural and Food Chemistry | volume = 55 | issue = 3| pages = 992–1002 | doi=10.1021/jf062800k| pmid = 17263504 }}</ref>
 ==Metabolism==
-Laricitrin is formed from [[myricetin]] by the action of the enzyme [[myricetin O-methyltransferase]].<ref>[http://metacyc.org/META/new-image?type=PATHWAY&object=PWY-5391 Syringetin biosynthetis pathway on metacyc.org]</ref> It is further methylated by <!-- the same enzyme -->[[laricitrin 5'-O-methyltransferase]] into [[syringetin]].
+Laricitrin is formed from [[myricetin]] by the action of the enzyme [[myricetin O-methyltransferase]].<ref>[http://metacyc.org/META/new-image?type=PATHWAY&object=PWY-5391 Syringetin biosynthesis pathway on metacyc.org]</ref> It is further methylated by <!-- the same enzyme -->[[laricitrin 5'-O-methyltransferase]] into [[syringetin]].
-===Glycosides===
+=== Glycosides ===
 * [[Laricitrin 3-O-galactoside]], found in grape<ref name=Mattivi/>
-* [[Laricitrin 3-glucoside]] found in ''[[Larix sibirica]]''<ref>[http://www.springerlink.com/content/t305644523714530/ New flavonol glycosides from the needles of Larix sibirica . N. A. Tyukavkina, S. A. Medvedeva and S. Z. Ivanova, Chemistry of Natural Compounds, Volume 10, Number 2 / march 1974]</ref>
+* [[Laricitrin 3-glucoside]] found in ''[[Larix sibirica]]''<ref>{{cite journal | doi=10.1007/BF00563605 | volume=10 | title=New flavonol glycosides from the needles of Larix sibirica | year=1974 | journal=Chemistry of Natural Compounds | pages=170–172 | last1 = Tyukavkina | first1 = N. A. | last2 = Medvedeva | first2 = S. A. | last3 = Ivanova | first3 = S. Z.| issue=2 }}</ref>
-* [[Laricitrin 3,5’-di-O-β-glucopyranoside]], found in ''[[Medicago littoralis]]''<ref>[http://www1.unifi.it/caryologia/past_volumes/63_1/63_1_12.pdf Flavonoids isolated from ''Medicago littoralis'' Rhode (Fabaceae): their ecological and chemosystematic significance]</ref>
+* [[Laricitrin 3,5’-di-O-β-glucopyranoside]], found in ''[[Medicago littoralis]]''<ref>[http://www1.unifi.it/caryologia/past_volumes/63_1/63_1_12.pdf Flavonoids isolated from ''Medicago littoralis'' Rhode (Fabaceae): their ecological and chemosystematic significance] {{webarchive|url=https://web.archive.org/web/20110722063750/http://www1.unifi.it/caryologia/past_volumes/63_1/63_1_12.pdf |date=2011-07-22 }}</ref>
-==References==
+== References ==
 {{reflist}}
 {{flavonol}}
-[[Category:Flavonols]]
+[[Category:O-methylated flavonols]]
 [[Category:Resorcinols]]
 [[Category:Catechols]]
-[[Category:Phenol ethers]]
-{{Natural-phenol-stub}}