Apigenin
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IUPAC name
4′,5,7-Trihydroxyflavone
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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
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard
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100.007.540 |
IUPHAR/BPS |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C15H10O5 | |
Molar mass | 270.240 g·mol−1 |
Appearance | Yellow crystalline solid |
Melting point | 345 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 their standard state (at 25 °C [77 °F], 100 kPa).
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Apigenin (4′,5,7-trihydroxyflavone), found in many plants, is a
Sources in nature
Apigenin is found in many fruits and vegetables, but parsley, celery, celeriac, and chamomile tea are the most common sources.[3] Apigenin is particularly abundant in the flowers of chamomile plants, constituting 68% of total flavonoids.[4] Dried parsley can contain about 45 mg apigenin/gram of the herb, and dried chamomile flower about 3–5 mg/gram.[5] 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.[6]
Pharmacology
Apigenin competitively binds to the benzodiazepine site on GABAA receptors.[7] There exist conflicting findings regarding how apigenin interacts with this site.[8][9]
Biosynthesis
Apigenin is biosynthetically derived from the general phenylpropanoid pathway and the flavone synthesis pathway.[10] The phenylpropanoid pathway starts from the aromatic amino acids L-phenylalanine or L-tyrosine, both products of the Shikimate pathway.[11] When starting from L-phenylalanine, first the amino acid is non-oxidatively deaminated by phenylalanine ammonia lyase (PAL) to make cinnamate, followed by oxidation at the para position by cinnamate 4-hydroxylase (C4H) to produce p-coumarate. As L-tyrosine is already oxidized at the para position, it skips this oxidation and is simply deaminated by tyrosine ammonia lyase (TAL) to arrive at p-coumarate.[12] To complete the general phenylpropanoid pathway, 4-coumarate CoA ligase (4CL) substitutes coenzyme A (CoA) at the carboxy group of p-coumarate. Entering the flavone synthesis pathway, the type III polyketide synthase enzyme chalcone synthase (CHS) uses consecutive condensations of three equivalents of malonyl CoA followed by aromatization to convert p-coumaroyl-CoA to chalcone.[13] Chalcone isomerase (CHI) then isomerizes the product to close the pyrone ring to make naringenin. Finally, a flavanone synthase (FNS) enzyme oxidizes naringenin to apigenin.[14] 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.[15]
Glycosides
The naturally occurring glycosides formed by the combination of apigenin with sugars include:
- Apiin (apigenin 7-O-apioglucoside), isolated from parsley[16] and celery
- Apigetrin (apigenin 7-glucoside), found in dandelion coffee
- Vitexin (apigenin 8-C-glucoside)
- Isovitexin (apigenin 6-C-glucoside)
- neohesperidoside)
- arabinoside)
In diet
Some foods contain relatively high amounts of apigenin:[17]
Product | Apigenin (milligrams per 100 grams) |
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Chamomile | 300-500 |
Parsley | 215.5 |
Celery hearts, green | 19.1 |
Rutabagas, raw | 4 |
See also
References
- ^ Merck Index, 11th Edition, 763.
- ^ The Systematic Identification of Flavonoids. Mabry et al, 1970, page 81
- ^ The compound in the Mediterranean diet that makes cancer cells 'mortal' Emily Caldwell, Medical Express, May 20, 2013.
- PMID 26487830.
- PMID 29399439.
- ^ Delage, PhD, Barbara (November 2015). "Flavonoids". Corvallis, Oregon: Linus Pauling Institute, Oregon State University. Retrieved 2021-01-26.
- PMID 7617761.
- PMID 10543878.
- PMID 10751547.
- ISSN 0179-9541.
- PMID 7870841.
- PMID 25975614.
- PMID 12636085.
- PMID 11524111.
- PMID 16332809.
- S2CID 8223136.
- ^ USDA Database for the Flavonoid Content of Selected Foods, Release 3 (2011)