Patuletin

Patuletin
Names

IUPAC name 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxychromen-4-one
Other names 6-Methoxyquercetin Quercetagetin 6-methyl ether 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4-benzopyrone
Identifiers
CAS Number	519-96-0^Y=
ChEBI	CHEBI:75164^N
ChEMBL	ChEMBL465155^N
ChemSpider	4444997^N
EC Number	208-280-8
Jmol interactive 3D	Image
PubChem	5281678
InChI InChI=1S/C16H12O8/c1-23-16-9(19)5-10-11(13(16)21)12(20)14(22)15(24-10)6-2-3-7(17)8(18)4-6/h2-5,17-19,21-22H,1H3^N Key: JMIFIYIEXODVTO-UHFFFAOYSA-N^N InChI=1/C16H12O8/c1-23-16-9(19)5-10-11(13(16)21)12(20)14(22)15(24-10)6-2-3-7(17)8(18)4-6/h2-5,17-19,21-22H,1H3 Key: JMIFIYIEXODVTO-UHFFFAOYAR
SMILES COC1=C(C=C2C(=C1O)C(=O)C(=C(O2)C3=CC(=C(C=C3)O)O)O)O
Properties
Chemical formula	C₁₆H₁₂O₈
Molar mass	332.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Patuletin is an O-methylated flavonol. It can be found in the genus Eriocaulon.^[1]

Glycosides

Patuletin glycosides can be found in Ipomopsis aggregata.^[2]

Patuletin-3-O-rutinoside can be isolated from the aerial parts of Echinacea angustifolia.^[3]

Patuletin acetylrhamnosides can be isolated from Kalanchoe brasiliensis.^[4]

References

↑ Bate-Smith, E. C.; Harborne, J. B. (1969). "Quercetagetin and patuletin in Eriocaulon". Phytochemistry 8 (6): 1035. doi:10.1016/S0031-9422(00)86351-7.
↑ Smith, D. M.; Glennie, C. W.; Harborne, J. B. (1971). "Identification of eupalitin, eupatolitin and patuletin glycosides in Ipomopsis aggregata". Phytochemistry 10 (12): 3115. doi:10.1016/S0031-9422(00)97361-8.
↑ Lin, L.; Qiu, S.; Lindenmaier, M.; He, X.; Featherstone, T.; Cordell, G. A. (2002). "Patuletin-3-O-Rutinoside from the Aerial Parts of Echinacea angustifolia". Pharmaceutical Biology 40 (2): 92. doi:10.1076/phbi.40.2.92.5839.
↑ Costa, S. S.; Jossang, A.; Bodo, B.; Souza, M. L. M.; Moraes, V. L. G. (1994). "Patuletin Acetylrhamnosides from Kalanchoe brasiliensis as Inhibitors of Human Lymphocyte Proliferative Activity". Journal of Natural Products 57 (11): 1503–1510. doi:10.1021/np50113a005. PMID 7853000.

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

Rhodionin
Rhodiosin

Glycosides of kaempferol

Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)

Glycosides of myricetin

Betmidin (Myricetin 3-O-arabinoside)
Myricetin 3-O-rutinoside
Myricetin-3-O-neohesperidoside
Myricitrin (Myricetin 3-O-rhamnoside)

Conjugates of quercetin

Sulfates	Quercetin 3-O-sulfate Quercetin 3,3'-bissulfate Quercetin 3,4'-bissulfate

Glycosides	Avicularin (quercetin-3-O-α-L-arabinofuranoside) CTN-986 Guaijaverin (quercetin 3-O-arabinoside) Heliosin (quercetin 3-digalactoside) Hyperoside (quercetin 3-O-galactoside) Isoquercetin (quercetin 3-O-glucoside) Miquelianin (quercetin 3-O-glucuronide) Quercetin 3,4'-diglucoside Quercetin-3-sophorodide Quercitrin (quercetin 3-O-rhamnoside) Rutin (quercetin rutinoside) Reinutrin (quercetin-3-D-xyloside) Spiraeoside (quercetin 4'-O-glucoside) Taxillusin (galloylated 3-O-glucoside of quercetin°

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside

other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)

Derivative flavonols

Aglycones	Noricaritin Dihydronoricaritin

Glycosides	Amurensin Icariin Phelloside Dihydrophelloside Rutin S

Pyranoflavonols

Aglycones	Karanjachromene

Furanoflavonols

Aglycones	Karanjin

Glycosides	Pongamoside A, B and C

Semisynthetic

Glycosides	Hydroxyethylrutosides Monoxerutin Troxerutin

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