Luteolinidin
Names
IUPAC name
3′,4′,5,7-Tetrahydroxyflavylium
Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-1λ4 -benzopyran-1-ylium
Other names
2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromenylium
Identifiers
ChemSpider
UNII
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
C1=CC(=C(C=C1C2=[O+]C3=CC(=CC(=C3C=C2)O)O)O)O
Properties
C15 H11 O5 +
Molar mass
271.24 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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
3-Hydroxyanthocyanidins 3-Deoxyanthocyanidins O -Methylated anthocyanidinsAnthocyanins (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)
Idaein (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)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
Coumaroylated anthocyanins (cis - and trans -) Caffeoylated anthocyanins
Malvidin 3-O -(6-p -caffeoyl)glucoside
Peonidin 3-O -(6-p -caffeoyl)glucoside
Malonylated anthocyanins
Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)
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)
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
Miscellaneous