Orientin

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Orientin

IUPAC name 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4, 5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
Other names Lutexin, Luteolin-8-C-glucoside
Identifiers
CAS number	28608-75-5^Y
PubChem	5281675
	ChEBI	CHEBI:7781^N
ChEMBL	CHEMBL239559^N
Jmol-3D images	Image 1
SMILES C1(=C2C(=C(C=C1O)O)C(=O)C=C(O2)C3=CC=C(O)C(=C3)O)C4OC(CO)C(C(C4O)O)O
Properties
Molecular formula	C₂₁H₂₀O₁₁
Molar mass	448.38 g/mol
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Orientin is a flavone, a chemical flavonoid-like compound. It is the 8-C glucoside of luteolin.

Natural occurrences

Orientin is also reported in the passion flower,^[2] the Açaí palm and in millets.^[3]

↑ Isolation and purification of four flavone C-glycosides from antioxidant of bamboo leaves by macroporous resin column chromatography and preparative high-performance liquid chromatography. Yu Zhang, Jingjing Jiao, Chengmei Liu, Xiaoqin Wu and Ying Zhang, Food Chemistry, 1 April 2008,, Volume 107, Issue 3, Pages 1326–1336, doi:10.1016/j.foodchem.2007.09.037
↑ Separation by capillary electrophoresis of C-glycosylflavonoids in Passiflora sp. extracts. E. R. Pastene, G. Bocaz, I. Peric, M. Montes, V. Silva and E. Riffo, Bol. Soc. Chil. Quím., v.45 n.3 Concepción set. 2000, doi:10.4067/S0366-16442000000300017
↑ Sorghum and millet phenols and antioxydants, Linda Dykes, Lloyd W. Rooney, in Journal of Cereal Science, 2006, 44, pages 236-251, doi:10.1016/j.jcs.2006.06.007

Flavones and their conjugates

Aglycones

Monohydroxyflavone	6-Hydroxyflavone

Dihydroxyflavones	Chrysin (5,7-dihydroxyflavone) 4',7-Dihydroxyflavone

Trihydroxyflavones	Apigenin (5,7,4'-trihydroxyflavone) Baicalein (5,6,7-trihydroxyflavone) Norwogonin (5,7,8-Trihydroxyflavone)

Tetrahydroxyflavones	Isoscutellarein (5,7,8,4'-Tetrahydroxyflavone or 8-Hydroxyapigenin) Luteolin (3',4',5,7-Tetrahydroxyflavone) Norartocarpetin (2',4',5,7-Tetrahydroxyflavone) Scutellarein (5,6,7,4'-Tetrahydroxyflavone)

Pentahydroxyflavones	6-Hydroxyluteolin Hypolaetin (8-Hydroxyluteolin) Tricetin (5,7,3',4',5'-Pentahydroxyflavone)

O-methylated flavones	Acacetin (Apigenin 4'-methyl ether) Artocarpetin (Norartocarpetin 7-methyl ether) Chrysoeriol (Luteolin 3'-methyl ether) Cirsilineol (4',5-Dihydroxy-3',6,7-trimethoxyflavone) Cirsiliol (3',4',5-trihydoxy-6,7-dimethoxyflavone) Cirsimaritin (Scutellarein 6,7-dimethyl ether) Diosmetin (Luteolin 4'-methyl ether) Eupatilin (5,7-Dihydroxy-3',4',6-trimethoxyflavone) Genkwanin (Apigenin 7-methyl ether) Nepetin (Luteolin 6-methyl ether) Nobiletin (3',4',5,6,7,8-Hexamethoxyflavone) Oroxylin A (Baicalein 6-methyl ether) Pratol (7-Hydroxy-4-methoxyflavone) Salvigenin (5-Hydroxy-6,7,4'-trimethoxyflavone) Sinensetin (3',4',5,6,7-Pentamethoxyflavone) Tangeritin (4',5,6,7,8-Pentamethoxyflavone) Techtochrysin (Chrysin 7-methyl ether) Tricin (Tricetin 3',5'-dimethyl ether) Wogonin (Norwogonin 8-methyl ether) Zapotin (2,6,5,6-tetramethoxyflavone)

of apigenin	Apiin (Apigenin-7-O-apioglucoside) Apigetrin (Apigenin 7-O-glucoside) Isovitexin (Apigenin 6-C-glucoside) Rhoifolin (Apigenin 7-O-neohesperidoside) Saponarin (Isovitexin-7-O-glucoside) Schaftoside (Apigenin 6-C-glucoside 8-C-arabinoside) Vicenin-2 (Apigenin 6,8-di-C-glucoside) Vitexin (Apigenin-8-C-glucoside)

of baicalein	Baicalin (Baicalein 7-O-glucuronide) Tetuin (Baicalein 6-O-glucoside)

of hypolaetin	Hypolaetin 8-glucoside Hypolaetin 8-glucuronide

of luteolin	Cynaroside (Luteolin 7-O-glucoside) Isoorientin (Luteolin 6-C-glucoside) Orientin (Luteolin 8-C-glucoside) Veronicastroside (Luteolin 7-O-neohesperidoside) Luteolin-7-O-glucuronide

Giraldiin A (4',5,5',7-Tetrahydroxy-3-methoxy-3'-O-α-L-arabinopyranosyloxyflavone) and B (5,5',7'-Trihydroxy-2',3-dimethoxy-4'-O-β-D-glucopyranosyloxyflavone)
Nepitrin (Nepetin 7-O-glucoside)
Oroxindin (Wogonin 7-O-glucuronide)
Scutellarin (Scutellarein 7-O-glucuronide)

Acetylated

Sulfated glycosides

Theograndin I (sulfated glucuronide of isoscutellarein) and II

Polymers

Drugs

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