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Apigenin

Apigenin (4′,5,7-trihydroxyflavone), found in many plants, is anatural product belonging to theflavone class that is theaglycone of several naturally occurringglycosides. It is a yellow crystalline solid that has been used to dye wool.

Apigenin[1]
Apigenin
Apigenin
Names
IUPAC name
4′,5,7-Trihydroxyflavone
Systematic IUPAC name
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Other names
Apigenine; Chamomile; Apigenol; Spigenin; Versulin; C.I. Natural Yellow 1
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.007.540Edit this at Wikidata
EC Number
  • 208-292-3
KEGG
UNII
  • InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H checkY
    Key: KZNIFHPLKGYRTM-UHFFFAOYSA-N checkY
  • InChI=1/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
    Key: KZNIFHPLKGYRTM-UHFFFAOYAX
  • O=C\1c3c(O/C(=C/1)c2ccc(O)cc2)cc(O)cc3O
Properties
C15H10O5
Molar mass270.240 g·mol−1
AppearanceYellow crystalline solid
Melting point345 to 350 °C (653 to 662 °F; 618 to 623 K)
UV-vis (λmax)267, 296sh, 336 nm in methanol[2]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Sources in nature

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Apigenin is found in many fruits and vegetables, butparsley,celery,celeriac, andchamomile tea are the most common sources.[3] Apigenin is particularly abundant in the flowers of chamomile plants, constituting 68% of totalflavonoids.[4] Dried parsley can contain about 45 mg apigenin/gram of the herb. The apigenin content of fresh parsley is reportedly 215.5 mg/100 grams, which is much higher than the next highest food source, green celery hearts providing 19.1 mg/100 grams.[5]

Pharmacology

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Apigenin competitively binds to the benzodiazepine site onGABAA receptors.[6] There exist conflicting findings regarding how apigenin interacts with this site.[7][8] Apigenin can increase the activity of endogenous antioxidant enzymes such as SOD and CAT, helping to reduce oxidative stress.[9][10]

Biosynthesis

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Apigenin is biosynthetically derived from the generalphenylpropanoid pathway and the flavone synthesis pathway.[11] The phenylpropanoid pathway starts from the aromatic amino acids L-phenylalanine orL-tyrosine, both products of theShikimate pathway.[12] When starting from L-phenylalanine, first the amino acid is non-oxidatively deaminated byphenylalanine ammonia lyase (PAL) to make cinnamate, followed by oxidation at thepara position bycinnamate 4-hydroxylase (C4H) to producep-coumarate. As L-tyrosine is already oxidized at thepara position, it skips this oxidation and is simply deaminated bytyrosine ammonia lyase (TAL) to arrive atp-coumarate.[13] To complete the general phenylpropanoid pathway,4-coumarate CoA ligase (4CL) substitutes coenzyme A (CoA) at the carboxy group ofp-coumarate. Entering the flavone synthesis pathway, the type IIIpolyketide synthase enzymechalcone synthase (CHS) uses consecutive condensations of three equivalents ofmalonyl CoA followed by aromatization to convertp-coumaroyl-CoA tochalcone.[14]Chalcone isomerase (CHI) then isomerizes the product to close the pyrone ring to makenaringenin. Finally, a flavanone synthase (FNS) enzyme oxidizes naringenin to apigenin.[15] Two types of FNS have previously been described; FNS I, a soluble enzyme that uses 2-oxogluturate, Fe2+, and ascorbate as cofactors and FNS II, a membrane bound, NADPH dependent cytochrome p450 monooxygenase.[16]

Glycosides

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

In diet

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Some foods contain relatively high amounts of apigenin:[18]

ProductApigenin
(milligrams per 100 grams)
Parsley, dried4503.5
Parsley, fresh215.5
Celery hearts, green19.1
Rutabagas, raw4

See also

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References

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  1. ^Merck Index, 11th Edition,763.
  2. ^The Systematic Identification of Flavonoids. Mabry et al, 1970, page 81
  3. ^The compound in the Mediterranean diet that makes cancer cells 'mortal' Emily Caldwell, Medical Express, May 20, 2013.
  4. ^Venigalla M, Gyengesi E, Münch G (August 2015)."Curcumin and Apigenin – novel and promising therapeutics against chronic neuroinflammation in Alzheimer's disease".Neural Regeneration Research.10 (8):1181–5.doi:10.4103/1673-5374.162686.PMC 4590215.PMID 26487830.
  5. ^Delage, PhD, Barbara (November 2015)."Flavonoids". Corvallis, Oregon:Linus Pauling Institute, Oregon State University. Retrieved2021-01-26.
  6. ^Viola, H.; Wasowski, C.; Levi de Stein, M.; Wolfman, C.; Silveira, R.; Dajas, F.; Medina, J. H.; Paladini, A. C. (June 1995)."Apigenin, a component of Matricaria recutita flowers, is a central benzodiazepine receptors-ligand with anxiolytic effects".Planta Medica.61 (3):213–216.doi:10.1055/s-2006-958058.ISSN 0032-0943.PMID 7617761.
  7. ^Dekermendjian, K.; Kahnberg, P.; Witt, M. R.; Sterner, O.; Nielsen, M.; Liljefors, T. (1999-10-21)."Structure-activity relationships and molecular modeling analysis of flavonoids binding to the benzodiazepine site of the rat brain GABA(A) receptor complex".Journal of Medicinal Chemistry.42 (21):4343–4350.doi:10.1021/jm991010h.ISSN 0022-2623.PMID 10543878.
  8. ^Avallone, R.; Zanoli, P.; Puia, G.; Kleinschnitz, M.; Schreier, P.; Baraldi, M. (2000-06-01)."Pharmacological profile of apigenin, a flavonoid isolated from Matricaria chamomilla".Biochemical Pharmacology.59 (11):1387–1394.doi:10.1016/s0006-2952(00)00264-1.ISSN 0006-2952.PMID 10751547.
  9. ^Blanca (Aug 7, 2024)."Top 6 Benefits of Apigenin for Health".Stanford Chemicals. RetrievedOct 16, 2024.
  10. ^Singh, Abhinav; Singh, Jagjit (2024). "A comprehensive review of apigenin a dietary flavonoid: biological sources, nutraceutical prospects, chemistry and pharmacological insights and health benefits".Critical Reviews in Food Science and Nutrition:1–37.doi:10.1080/10408398.2024.2390550.PMID 39154213.
  11. ^Forkmann, G. (January 1991)."Flavonoids as Flower Pigments: The Formation of the Natural Spectrum and its Extension by Genetic Engineering".Plant Breeding.106 (1):1–26.doi:10.1111/j.1439-0523.1991.tb00474.x.ISSN 0179-9541.
  12. ^Herrmann KM (January 1995)."The shikimate pathway as an entry to aromatic secondary metabolism".Plant Physiology.107 (1):7–12.doi:10.1104/pp.107.1.7.PMC 161158.PMID 7870841.
  13. ^Lee H, Kim BG, Kim M, Ahn JH (September 2015)."Biosynthesis of Two Flavones, Apigenin and Genkwanin, in Escherichia coli".Journal of Microbiology and Biotechnology.25 (9):1442–8.doi:10.4014/jmb.1503.03011.PMID 25975614.
  14. ^Austin MB, Noel JP (February 2003). "The chalcone synthase superfamily of type III polyketide synthases".Natural Product Reports.20 (1):79–110.CiteSeerX 10.1.1.131.8158.doi:10.1039/b100917f.PMID 12636085.
  15. ^Martens S, Forkmann G, Matern U, Lukacin R (September 2001). "Cloning of parsley flavone synthase I".Phytochemistry.58 (1):43–6.Bibcode:2001PChem..58...43M.doi:10.1016/S0031-9422(01)00191-1.PMID 11524111.
  16. ^Leonard E, Yan Y, Lim KH, Koffas MA (December 2005)."Investigation of two distinct flavone synthases for plant-specific flavone biosynthesis in Saccharomyces cerevisiae".Applied and Environmental Microbiology.71 (12):8241–8.Bibcode:2005ApEnM..71.8241L.doi:10.1128/AEM.71.12.8241-8248.2005.PMC 1317445.PMID 16332809.
  17. ^Meyer H, Bolarinwa A, Wolfram G, Linseisen J (2006)."Bioavailability of apigenin from apiin-rich parsley in humans".Annals of Nutrition & Metabolism.50 (3):167–72.doi:10.1159/000090736.PMID 16407641.S2CID 8223136.
  18. ^USDA Database for the Flavonoid Content of Selected Foods, Release 3 (2011)
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