5,7,4'-trihydroxyflavone

Apigenin[1]
Identifiers
CAS number 520-36-5 YesY
PubChem 5280443
ChemSpider 4444100 YesY
DrugBank DB07352
KEGG C01477 YesY
ChEBI CHEBI:18388 YesY
Jmol-3D images Image 1
Properties
Molecular formula C15H10O5
Molar mass 270.24 g mol−1
Appearance Yellow crystalline solid
Melting point

345–350 °C

λmax 267, 296sh, 336 nm in methanol[2]
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Apigenin (4’,5,7-trihydroxyflavone), found in many plants, is a natural product belonging to the flavone class that is the aglycone of several naturally occurring glycosides. It is a yellow crystalline solid that has been used to dye wool.

Pharmacological study

It was recently shown that apigenin induces autophagy (a kind of cellular waste-recycling system) in leukemia cells, which may support a possible chemopreventive role, but that induction of autophagy simultaneously induces resistance against the chemotherapy drug vincristine.[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 prevent renal damage caused by cyclosporin in rats, associated with reduced expression of the cell death mediator bcl-2 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]

In vitro studies have shown that apigenin may be toxic to red blood cells.[9]

Apigenin may also stimulate adult neurogenesis, with at least one study claiming that apigenin "stimulate[s] adult neurogenesis in vivo and in vitro, by promoting neuronal differentiation" and may be useful "for stimulating adult neurogenesis and for the treatment of neurological diseases, disorders and injuries, by stimulating the generation of neuronal cells in the adult brain." While potentially promising, the study used rats and its effects have yet to be demonstrated in humans. [10]

Sources in nature

Apigenin is found in many fruits and vegetables, but parsley, celery and chamomile tea are the most common sources.[11]

Glycosides

The naturally occurring glycosides formed by the combination of apigenin with sugars include:

References

This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and USA.gov, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for USA.gov and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
 
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
 
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.