Apigenin
| Apigenin[1] | |
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5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one |
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Other names
Apigenine; Chamomile; Apigenol; Spigenin; Versulin; 4',5,7-Trihydroxyflavone; C.I. Natural Yellow 1 |
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| Identifiers | |
| CAS number | 520-36-5  |
| PubChem | 5280443 |
| ChemSpider | 4444100 |
| DrugBank | DB07352 |
| KEGG | C01477 |
| ChEBI | CHEBI:18388 |
| ChEMBL | CHEMBL28 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C15H10O5 |
| Molar mass | 270.24 g mol−1 |
| Exact mass | 270.052823 |
| Appearance | Yellow crystalline solid |
| Melting point |
345–350 °C |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Apigenin (4’,5,7-trihydroxyflavone) is a flavone that is the aglycone of several glycosides. It is a yellow crystalline solid that has been used to dye wool. Apigenin may contribute to the chemopreventive action of vegetables and fruits.[2] It was recently shown that apigenin induces a process called autophagia (a kind of cellular dormancy) that may well explain its chemopreventive properties, but at the same time it induces resistance against chemotherapy.[3] Apigenin is a potent inhibitor of CYP2C9,[4] an enzyme responsible for the metabolism of many pharmaceutical drugs in the body.
Apigenin has been shown to reverse the adverse effects of cyclosporin. Research has been conducted to study the effects of apigenin on reversal of cyclosporin-induced damage, and this was assessed by immunohistochemical estimation of expression of bcl-2, and estimation of apoptosis in histopathological sections.[5] Cyclosporine A enhances the expression of transforming growth factor-β in the rat kidney, which signifies accelerated apoptosis. Therefore, transforming growth factor-β and apoptotic index may be used to assess apigenin and its effect on cyclosporine A-induced renal damage.[6]
Apigenin acts as a monoamine transporter activator, one of the few chemicals demonstrated to possess this property.[7] Apigenin is a ligand for central benzodiazepine receptors that competitively inhibited the binding of flunitrazepam with a Ki of 4μM, exerting anxiolytic and slight sedative effects.[8]
[edit] Glycosides
Glycosides, formed by the derivatization of apigenin with sugars, include:
- Apiin, isolated from parsley and celery
- Apigetrin (apigenin-7-glucoside), found in dandelion coffee
- Vitexin (apigenin-8-C-glucoside)
- Isovitexin (apigenin-6-C-glucoside or homovitexin, saponaretin)
- Rhoifolin (Apigenin 7-O-neohesperidoside)
- Schaftoside
[edit] References
- ^ Merck Index, 11th Edition, 763.
- ^ CV Ferreira, GZ Gusto, AC Sousa, KC Queiroz, WF Zambuzzi, H Aoyama, MP Peppelenbosch (2006). "Natural compounds as a source of protein phosphatase inhibitors; application to the rational design of small-molecule derivatives.". Biochemie 88 (12): 1859–73. doi:10.1016/j.biochi.2006.08.007. PMID 17010496.
- ^ RR Ruela-de-Sousa, GM Fuhler, N Blom, CV Ferreira, H Aoyama, MP Peppelenbosch (2010). "Cytotoxicity of apigenin on leukemia cell lines: implications for prevention and therapy". Cell Death and Disease 1 (e19): 1–11. doi:10.1038/cddis.2009.18. PMC 3032507. PMID 21364620. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3032507.
- ^ Si Dayong, Wang Y, Zhou Y-H, Guo Y, Wang J, Zhou H, Li Z-S, Fawcett JP (March 2009). "Mechanism of CYP2C9 inhibition by flavones and flavonols". Drug Metabolism and Disposition 37 (3): 629–634. doi:10.1124/dmd.108.023416. PMID 19074529. http://p4502c.googlepages.com/dmd2.pdf.
- ^ Srikumar Chakravarthi, Chong Fu Wen, HS Nagaraja (2009). "Apoptosis and expression of bcl-2 in cyclosporin induced renal damage and its reversal by beneficial effects of 4,5,7 - Trihydroxyflavone". Journal of Analytical Bio Science 32 (4): 320–327.
- ^ Chong FW, Srikumar Chakravarthi, HS Nagaraja, PM Thanikachalam, Nagarajah Lee (2009). "Expression of Transforming Growth factor-β and determination of Apoptotic Index in histopathological sections for assessment of the effects of Apigenin (4',5',7'- trihydroxyflavone) on Cyclosporine A induced renal damage". Malaysian Journal of Pathology 31 (1): 35–43. PMID 19694312.
- ^ Zhao, G; Qin, GW; Wang, J; Chu, WJ; Guo, LH (2010). "Functional activation of monoamine transporters by luteolin and apigenin isolated from the fruit of Perilla frutescens (L.) Britt". Neurochemistry international 56 (1): 168–76. doi:10.1016/j.neuint.2009.09.015. PMID 19815045.
- ^ Viola H, Wasowski C, Levi de Stein M, Wolfman C, Silveira R, Dajas F, Medina JH, Paladini AC."Apigenin, a component of Matricaria recutita flowers, is a central benzodiazepine receptors-ligand with anxiolytic effects."
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