Scutellarin

From Wikipedia, the free encyclopedia

Scutellarin

Other names Breviscapine; Breviscapin; Scutellarein-7-glucuronide; Scutellarein-7beta-D-glucuronide; Scutellarein-7beta-D-glucuronoside; Scutellarein-7-O-beta-D-glucuronide; 7-(β-D-glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Identifiers
CAS number	27740-01-8^Y
PubChem	185617
ChemSpider	161366^N
ChEBI	CHEBI:61278^N
ChEMBL	CHEMBL487805^N
Jmol-3D images	{{#if:O=C3\C=C(/Oc2cc(O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O)c(O)c(O)c23)c4ccc(O)cc4\|Image 1
SMILES O=C3\C=C(/Oc2cc(O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O)c(O)c(O)c23)c4ccc(O)cc4
InChI InChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)10-5-9(23)13-11(31-10)6-12(14(24)15(13)25)32-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-22,24-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1^N Key: DJSISFGPUUYILV-ZFORQUDYSA-N^N InChI=1/C21H18O12/c22-8-3-1-7(2-4-8)10-5-9(23)13-11(31-10)6-12(14(24)15(13)25)32-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-22,24-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1 Key: DJSISFGPUUYILV-ZFORQUDYBK
Properties
Molecular formula	C₂₁H₁₈O₁₂
Molar mass	462.36 g/mol
Hazards
LD₅₀	1314 mg/kg (mouse, intravenous) ^[1]
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

Scutellarin is a flavone, a type of phenolic chemical compound. It can be found in Scutellaria barbata and S. lateriflora. The determination of the structure of scutellarin took Guido Goldschmiedt many years: after the first publication on that topic in 1901, only in 1910 he managed to obtain enough starting material for more detailed studies.

Scutellarin has been shown to induce apoptosis of ovarian and breast tumor cells in vitro.^{[citation needed]}

References

↑ Zhongcaoyao (1983): Chinese Traditional and Herbal Medicine. Bd. 14, S. 33.

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)

Glycosides

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

Artocarpetin A (prenylated artocarpetin)
Artoindonesianin P (prenylated)

Sulfated glycosides

Theograndin I (sulfated glucuronide of isoscutellarein) and II

Polymers

Amentoflavone

Drugs

This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.