Luteolinidin
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Names
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IUPAC name
3′,4′,5,7-Tetrahydroxyflavylium
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Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-1λ4-benzopyran-1-ylium
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Other names
2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromenylium
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Identifiers
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ChemSpider
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UNII
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InChI=1S/C15H10O5/c16-9-6-12(18)10-2-4-14(20-15(10)7-9)8-1-3-11(17)13(19)5-8/h1-7H,(H3-,16,17,18,19)/p+1 N Key: GDNIGMNXEKGFIP-UHFFFAOYSA-O N InChI=1/C15H10O5/c16-9-6-12(18)10-2-4-14(20-15(10)7-9)8-1-3-11(17)13(19)5-8/h1-7H,(H3-,16,17,18,19)/p+1 Key: GDNIGMNXEKGFIP-IKLDFBCSAL
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C1=CC(=C(C=C1C2=[O+]C3=CC(=CC(=C3C=C2)O)O)O)O
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Properties
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C15H11O5+
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Molar mass
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271.24 g/mol
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Luteolinidin is a member of the 3-deoxyanthocyanidins. It is an orange pigment, found e.g. in Sorghum bicolor.[1][2]
Glycosides
Luteolinidin 5-O-β-D-[3-O-β-D-glucopyranosyl-2-O-acetylglucopyranoside] (a 3-deoxyanthocyanidin
laminaribioside) can be found in the fern Parablechnum novae-zelandiae (syn. Blechnum novae-zelandiae).[3]
Antioxidant effect
In a study from 2017, Luteolinidin was found to have in vitro protective effect against LDL oxidation.[4]
See also
References
- ^ Nielsen, Kirsten A.; Gotfredsen, Charlotte H.; Buch-Pedersen, Morten J.; Ammitzbøll, Henriette; Mattsson, Ole; Duus, Jens Ø.; Nicholson, Ralph L. (2004). "Inclusions of flavonoid 3-deoxyanthocyanidins in Sorghum bicolor self-organize into spherical structures". Physiological and Molecular Plant Pathology. 65 (4): 187–196. Bibcode:2004PMPP...65..187N. doi:10.1016/j.pmpp.2005.02.001. S2CID 83721762.
- ^ Dykes, Linda; Rooney, Lloyd W. (2006). "Sorghum and millet phenols and antioxidants". Journal of Cereal Science. 44 (3): 236–251. doi:10.1016/j.jcs.2006.06.007. S2CID 4976794.
- ^ Swinny, Ewald E. (2001). "A novel acetylated 3-deoxyanthocyanidin laminaribioside from the fern Blechnum novae-zelandiae". Zeitschrift für Naturforschung C. 56 (3–4): 177–180. doi:10.1515/znc-2001-3-402. PMID 11371005. S2CID 6016283.
- ^ PMID 28356039
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3-Hydroxyanthocyanidins | |
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3-Deoxyanthocyanidins | |
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O-Methylated anthocyanidins | |
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Anthocyanins (anthocyaninidin glycosides) | Glucosides:
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)
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Acylated anthocyanins | Acetylated anthocyanins |
Cyanidin 3-O-(6-acetyl)glucoside
Delphinidin 3-O-(6-acetyl)glucoside
Malvidin 3-O-(6-acetyl)glucoside
Petunidin 3-O-(6-acetyl)galactoside
Petunidin 3-O-(6-acetyl)glucoside
Peonidin 3-O-(6-acetyl)glucoside
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Coumaroylated anthocyanins (cis- and trans-) | |
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Caffeoylated anthocyanins |
- Malvidin 3-O-(6-p-caffeoyl)glucoside
- Peonidin 3-O-(6-p-caffeoyl)glucoside
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Malonylated anthocyanins |
- Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)
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Acylated anthocyanin diglycosides |
- Cyanidin 3-O-(di-p-coumarylglucoside)-5-glucoside
- Gentiodelphin (delphinidin 3-''O''-glucosyl-5-''O''-(6-''O''-caffeoyl-glucosyl)-3′-''O''-(6-''O''-caffeoyl-glucoside))
- Nasunin (Delphinidin 3-(p-coumaroylrutinoside)-5-glucoside)
- Petanin (petunidin 3-[6-O-(4-O-(E)-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-D-glucopyranoside]-5-O-β-D-glucopyranoside)
- Violdelphin (Delphinidin 3-rutinoside-7-O-(6-O-(4-(6-O-(4-hydroxybenzoyl)-β-D-glucosyl)oxybenzoyl)-β-D-glucoside)
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Flavanol-anthocyanin adducts |
- 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
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Miscellaneous | |
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