Apigenin

Apigenin^[1]
Nama
	Nama IUPAC 4′,5,7-Trihidroksiflavon
	Nama IUPAC (sistematis) 5,7-Dihidroksi-2-(4-hidroksifenil)-4H-1-benzopiran-4-ona
	Nama lain Kamomil; Apigenol; Spigenin; Versulin; C.I. Natural Yellow 1
Penanda
Nomor CAS	520-36-5 ;
Model 3D (JSmol)	Gambar interaktif;
3DMet	{{{3DMet}}}
ChEBI	CHEBI:18388 ;
ChEMBL	ChEMBL28 ;
ChemSpider	4444100 ;
DrugBank	DB07352 ;
Nomor EC
IUPHAR/BPS	4136;
KEGG	C01477 ;
PubChem CID	5280443;
Nomor RTECS	{{{value}}}
UNII	7V515PI7F6 ;
CompTox Dashboard (EPA)	DTXSID6022391 ;
	InChI 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 Key: KZNIFHPLKGYRTM-UHFFFAOYSA-N ; 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;
	SMILES O=C\1c3c(O/C(=C/1)c2ccc(O)cc2)cc(O)cc3O;
Sifat
Rumus kimia	C15H10O5
Massa molar	270,24 g·mol−1
Penampilan	Padatan kristal berwarna kuning
Titik lebur	345–350 °C (653–662 °F; 618–623 K)
λmaks	267, 296sh, 336 nm pada metanol
	Kecuali dinyatakan lain, data di atas berlaku pada suhu dan tekanan standar (25 °C [77 °F], 100 kPa).
	verifikasi (apa ini ?)
	Referensi

Apigenin (4′,5,7-trihidroksiflavon), yang ditemukan di banyak tanaman, adalah produk alami yang termasuk dalam golongan flavon yang merupakan aglikon dari beberapa glikosida yang terdapat di alam. Produk ini berupa padatan kristal berwarna kuning yang telah digunakan untuk mewarnai wol.

Sumber di alam

Apigenin ditemukan dalam banyak buah-buahan dan sayuran; tetapi peterseli, seledri, dan teh kamomil adalah sumber yang paling umum.^[3] Apigenin sangat melimpah di bunga tanaman kamomil, yang merupakan 68% dari total flavonoid.^[4] Peterseli kering dapat mengandung sekitar 45 mg apigenin/gram herba, dan bunga kamomil kering sekitar 3–5 mg/gram.^[5] Kandungan apigenin peterseli segar dilaporkan 215,5 mg/100 gram, yang jauh lebih tinggi dari sumber makanan tertinggi berikutnya, yakni jantung seledri hijau yang menyediakan 19,1 mg/100 gram apigenin.^[6]

Farmakologi

Apigenin secara kompetitif mengikat situs benzodiazepin pada reseptor GABA_A.^[7] Ada temuan yang bertentangan mengenai bagaimana apigenin berinteraksi dengan situs ini.^[8]^[9] Apigenin dapat meningkatkan aktivitas enzim antioksidan endogen seperti SOD dan CAT, membantu mengurangi stres oksidatif.^[10]^[11]

Biosintesis

Glikosida

Dalam makanan

Referensi

^ 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.
^ 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.
^ Shankar E, Goel A, Gupta K, Gupta S (2017). "Plant flavone apigenin: An emerging anticancer agent". Current Pharmacology Reports. 3 (6): 423–446. doi:10.1007/s40495-017-0113-2. PMC 5791748  . PMID 29399439.
^ Delage, PhD, Barbara (November 2015). "Flavonoids". Corvallis, Oregon: Linus Pauling Institute, Oregon State University. Diakses tanggal 2021-01-26.
^ 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.
^ 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.
^ 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.
^ Blanca (Aug 7, 2024). "Top 6 Benefits of Apigenin for Health". Stanford Chemicals. Diakses tanggal Oct 16, 2024.
^ 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 Periksa nilai |pmid= (bantuan).

[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.

[pmid26487830-4] 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.

[pmid29399439-5] Shankar E, Goel A, Gupta K, Gupta S (2017). "Plant flavone apigenin: An emerging anticancer agent". Current Pharmacology Reports. 3 (6): 423–446. doi:10.1007/s40495-017-0113-2. PMC 5791748  . PMID 29399439.

[lpi-flav-6] Delage, PhD, Barbara (November 2015). "Flavonoids". Corvallis, Oregon: Linus Pauling Institute, Oregon State University. Diakses tanggal 2021-01-26.

[7] 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.

[8] 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.

[9] 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.

[10] Blanca (Aug 7, 2024). "Top 6 Benefits of Apigenin for Health". Stanford Chemicals. Diakses tanggal Oct 16, 2024.

[11] 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 Periksa nilai |pmid= (bantuan).

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