| Revision as of 06:17, 7 December 2010 editحسن علي البط (talk | contribs)Extended confirmed users, Pending changes reviewers19,940 edits added Category:Glucuronides using HotCat← Previous edit |
Latest revision as of 12:33, 23 January 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,057 edits Removed proxy/dead URL that duplicated identifier. |
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{{chembox |
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{{Chembox |
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| Name = Scutellarin |
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| verifiedrevid = 401008684 |
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| ImageFile = Scutellarin2.svg |
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| Name = Scutellarin |
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| ImageSize = 260px |
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| Reference = |
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| ImageName = 7-(beta-D-Glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one |
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| ImageFile = Scutellarin2.svg |
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| IUPACName = |
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| ImageSize = 260px |
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| OtherNames= Breviscapine; Breviscapin; ]-7-]; Scutellarein-7beta-D-glucuronide; Scutellarein-7beta-D-glucuronoside; Scutellarein-7-O-beta-D-glucuronide; 7-(β-<small>D</small>-glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4''H''-1-benzopyran-4-one |
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| ImageName = 7-(beta-D-Glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one |
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| Section1 = {{Chembox Identifiers |
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| IUPACName = 4′,5,6-Trihydroxy-4-oxoflav-2-en-7-yl β-<small>D</small>-glucopyranosiduronic acid |
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| CASNo = 27740-01-8 |
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| SystematicName = (2''S'',3''S'',4''S'',5''R'',6''S'')-6-{oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid |
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| SMILES = |
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| OtherNames = Breviscapine; Breviscapin; ]-7-]; Scutellarein-7beta-D-glucuronide; Scutellarein-7beta-D-glucuronoside; Scutellarein-7-O-beta-D-glucuronide; 7-(β-<small>D</small>-glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4''H''-1-benzopyran-4-one |
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| PubChem = 185617 |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 27740-01-8 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 61278 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 487805 |
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| PubChem = 185617 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 16IGP0ML9A |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 161366 |
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| SMILES = O=C3\C=C(/Oc2cc(O1O(C(=O)O)(O)(O)1O)c(O)c(O)c23)c4ccc(O)cc4 |
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| 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 |
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| InChIKey = DJSISFGPUUYILV-ZFORQUDYBK |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = DJSISFGPUUYILV-ZFORQUDYSA-N |
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|Section2={{Chembox Properties |
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| Formula = C<sub>21</sub>H<sub>18</sub>O<sub>12</sub> |
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| MolarMass = 462.36 g/mol |
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| MeltingPt = |
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|Section3={{Chembox Hazards |
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| LD50 = 1314 mg/kg (mouse, intravenous) <ref>Zhongcaoyao (1983): ''Chinese Traditional and Herbal Medicine.'' Bd. 14, S. 33.</ref> |
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'''Scutellarin''' is a ], a type of phenolic chemical compound. It can be found in the Asian "barbed skullcap" '']'' and the north American plant '']'' both of which have been used in traditional medicine. The compound is found only in trace amounts in the "Chinese skullcap" '']'', another plant used in traditional Chinese medicine. |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>21</sub>H<sub>18</sub>O<sub>12</sub> |
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| MolarMass = 462.36 g/mol |
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| ExactMass = 462.079826 |
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| MeltingPt = <!-- °C --> |
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}} |
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| Section3 = {{Chembox Hazards |
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| LD50 = 1314 mg/kg (mouse, intravenous) <ref>Zhongcaoyao (1983): ''Chinese Traditional and Herbal Medicine.'' Bd. 14, S. 33.</ref> |
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'''Scutellarin''' is a chemical compound that can be found in '']'' and '']''. The determination of the structure of scutellarin took ] 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. |
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The determination of the structure of scutellarin took ] 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. |
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Scutellarin has been shown to induce apoptosis of ovarian and breast tumor cells in vitro. |
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Scutellarin has anticancer properties. It has been found to induce ] of ovarian and breast tumor cells '']''. One mechanism of scutellarin's antitumor action is to bind to ] receptor II (TNFR2) in tumor-associated CD4+Foxp3+ regulatory T cells. These tumor "helper" cells show high expression of TNFR2 and are inhibited when it is blocked by scutellarin. <ref>{{cite journal | doi=10.1016/j.biopha.2022.113187 | title=Scutellarin enhances anti-tumor immune responses by reducing TNFR2-expressing CD4+Foxp3+ regulatory T cells | year=2022 | last1=Chen | first1=Shaokui | last2=Li | first2=Ruixin | last3=Chen | first3=Yibo | last4=Chou | first4=Chon-Kit | last5=Zhang | first5=Zhexuan | last6=Yang | first6=Yang | last7=Liao | first7=Ping | last8=Wang | first8=Qingqing | last9=Chen | first9=Xin | journal=Biomedicine & Pharmacotherapy | volume=151 | page=113187 | pmid=35676787 | s2cid=249140642 | doi-access=free }}</ref> |
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==External links== |
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Scutellarin also shows protective effects for nerve cells that are affected by estrogen.<ref>{{Cite journal|last1=Zhu|first1=Judy T. T.|last2=Choi|first2=Roy C. Y.|last3=Chu|first3=Glanice K. Y.|last4=Cheung|first4=Anna W. H.|last5=Gao|first5=Qiu T.|last6=Li|first6=Jun|last7=Jiang|first7=Zhi Y.|last8=Dong|first8=Tina T. X.|last9=Tsim|first9=Karl W. K.|date=2007-03-21|title=Flavonoids possess neuroprotective effects on cultured pheochromocytoma PC12 cells: a comparison of different flavonoids in activating estrogenic effect and in preventing beta-amyloid-induced cell death|journal=Journal of Agricultural and Food Chemistry|volume=55|issue=6|pages=2438–2445|doi=10.1021/jf063299z|issn=0021-8561|pmid=17323972}}</ref> |
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==References== |
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Scutellarin has been shown as a potential treatment for ], which could prevent diabetic blindness. In laboratory studies, scutellarin inhibits hypoxia-induced and moderately high glucose-induced proliferation and ] (VEGF) expression in human retinal endothelial cells; thus, it could be a potential therapy for diabetic retinopathy. However, how scutellarin inhibits VEGF is unknown.<ref>{{Cite journal|last1=Wang|first1=Difei|last2=Wang|first2=Lei|last3=Gu|first3=Jianqiu|last4=Yang|first4=Huijing|last5=Liu|first5=Nanqi|last6=Lin|first6=Yichen|last7=Li|first7=Xiaolin|last8=Shao|first8=Chen|date=September 2014|title=Scutellarin inhibits high glucose-induced and hypoxia-mimetic agent-induced angiogenic effects in human retinal endothelial cells through reactive oxygen species/hypoxia-inducible factor-1α/vascular endothelial growth factor pathway|journal=Journal of Cardiovascular Pharmacology|volume=64|issue=3|pages=218–227|doi=10.1097/FJC.0000000000000109|issn=1533-4023|pmid=25192544|s2cid=9443485}}</ref> |
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Scutellarin has anti-] effects as well. In laboratory studies, a drug-resistant type HIV-1 cell-to-cell infection was inhibited with significant potency. The scutellarin compound was found to inhibit several strains of HIV-1 replication with different potencies, by preventing HIV-1 particle attachment and cell fusion, as well as inhibiting HIV-1 retransmission.<ref>{{Cite journal|last1=Zhang|first1=Gao-Hong|last2=Wang|first2=Qian|last3=Chen|first3=Ji-Jun|last4=Zhang|first4=Xue-Mei|last5=Tam|first5=Siu-Cheung|last6=Zheng|first6=Yong-Tang|date=2005-09-02|title=The anti-HIV-1 effect of scutellarin|journal=Biochemical and Biophysical Research Communications|volume=334|issue=3|pages=812–816|doi=10.1016/j.bbrc.2005.06.166|issn=0006-291X|pmid=16023998}}</ref> |
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== References == |
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{{Polyphenol-stub}} |
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{{Aromatic-stub}} |
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