View source for Kolaflavanone

{{Short description|Kola nut flavanone}}

{{Infobox drug
| drug_name = Kolaflavanone
| image = Kolaflavanone.svg
| width = 
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<!-- Identifiers -->
| CAS_number = 68705-66-8
| CAS_supplemental = 97560-11-7
| PubChem = 155169
| IUPHAR_ligand = 
| DrugBank = 
| ChemSpiderID = 136697
| UNII = VY4E467596
| KEGG = C09761
| ChEBI = 28521
| ChEMBL = 4794351
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<!--Chemical data-->
| IUPAC_name = (2R,3R)-8-[(2S,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-3,5,7-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
| C=31 | H=24 | O=12
| SMILES = COC1=C(C=C(C=C1)[C@@H]2[C@H](C(=O)C3=C(C=C(C(=C3O2)[C@@H]4[C@H](OC5=CC(=CC(=C5C4=O)O)O)C6=CC=C(C=C6)O)O)O)O)O COC1=C(C=C(C=C1)[C@@H]2[C@H](C(=O)C3=C(C=C(C(=C3O2)[C@@H]4[C@H](OC5=CC(=CC(=C5C4=O)O)O)C6=CC=C(C=C6)O)O)O)O)O
| StdInChI = 1S/C31H24O12/c1-41-20-7-4-13(8-16(20)34)30-28(40)27(39)24-19(37)11-18(36)23(31(24)43-30)25-26(38)22-17(35)9-15(33)10-21(22)42-29(25)12-2-5-14(32)6-3-12/h2-11,25,28-30,32-37,40H,1H3/t25-,28-,29+,30+/m0/s1
| StdInChIKey = GJWXCPDVDRIBKP-CNTBMXMRSA-N
}}

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'''Kolaflavanone''' is a [[biflavonoid]] isolated from the nuts of ''[[Garcinia kola]]''. It has been reported to exhibit [[antioxidant]], [[neuroprotective]], [[antidiabetic]], and [[reproductive protective]] effects in experimental models.  

It shows antioxidant activity, including protection against [[gamma-radiation]] in animal models. Studies in ''[[Drosophila melanogaster]]'' suggest potential [[anti-Parkinson]] effects as well as increased longevity.<ref>{{cite journal | vauthors = Farombi EO, Abolaji AO, Farombi TH, Oropo AS, Owoje OA, Awunah MT | title = Garcinia kola seed biflavonoid fraction (Kolaviron), increases longevity and attenuates rotenone-induced toxicity in Drosophila melanogaster | journal = Pesticide Biochemistry and Physiology | volume = 145 | pages = 39–45 | date = February 2018 | pmid = 29482730 | doi = 10.1016/j.pestbp.2018.01.002 | bibcode = 2018PBioP.145...39F }}</ref>

Kolaflavanone (as part of the biflavonoid fraction kolaviron) has also been investigated for protective effects against reproductive toxicity. Findings from animal studies suggest amelioration of chemically or radiation-induced reproductive damage, although [[vitamin E]] has shown similar protective effects.<ref>{{cite journal | vauthors = Adaramoye OA, Arisekola M | title = Kolaviron, a biflavonoid complex from Garcinia kola seeds, ameliorates ethanol-induced reproductive toxicity in male wistar rats | journal = Nigerian Journal of Physiological Sciences | volume = 28 | issue = 1 | pages = 9–15 | date = June 2013 | pmid = 23955400 }}</ref><ref>{{cite journal | vauthors = Adedara IA, Farombi EO | title = Chemoprotection of ethylene glycol monoethyl ether-induced reproductive toxicity in male rats by kolaviron, isolated biflavonoid from Garcinia kola seed | journal = Human & Experimental Toxicology | volume = 31 | issue = 5 | pages = 506–517 | date = May 2012 | pmid = 22027498 | doi = 10.1177/0960327111424301 | bibcode = 2012HETox..31..506A }}</ref><ref>{{cite journal | vauthors = Adaramoye OA, Adedara IA, Farombi EO | title = Possible ameliorative effects of kolaviron against reproductive toxicity in sub-lethally whole body gamma-irradiated rats | journal = Experimental and Toxicologic Pathology | volume = 64 | issue = 4 | pages = 379–385 | date = May 2012 | pmid = 21036568 | doi = 10.1016/j.etp.2010.10.002 | bibcode = 2012EToxP..64..379A }}</ref>  In vitro studies indicate that kolaflavanone may protect neuronal cell lines from toxic insults induced by the herbicide atrazine, a known [[endocrine disruptor chemical|endocrine-disrupting chemical]].<ref>{{cite journal | vauthors = Abarikwu SO, Farombi EO, Pant AB | title = Biflavanone-kolaviron protects human dopaminergic SH-SY5Y cells against atrazine induced toxic insult | journal = Toxicology in Vitro | volume = 25 | issue = 4 | pages = 848–858 | date = June 2011 | pmid = 21333729 | doi = 10.1016/j.tiv.2011.02.005 | bibcode = 2011ToxVi..25..848A }}</ref><ref>{{cite journal | vauthors = Abarikwu SO, Farombi EO, Kashyap MP, Pant AB | title = Kolaviron protects apoptotic cell death in PC12 cells exposed to atrazine | journal = Free Radical Research | volume = 45 | issue = 9 | pages = 1061–1073 | date = September 2011 | pmid = 21726175 | doi = 10.3109/10715762.2011.593177 }}</ref>  Kolaflavanone has further been reported to exert antidiabetic effects in experimental models.<ref>{{cite journal | vauthors = Adaramoye OA | title = Antidiabetic effect of kolaviron, a biflavonoid complex isolated from Garcinia kola seeds, in Wistar rats | journal = African Health Sciences | volume = 12 | issue = 4 | pages = 498–506 | date = December 2012 | pmid = 23515095 | doi = 10.4314/ahs.v12i4.16 | pmc = 3598292 }}</ref>

Extraction methods for biflavonoids from ''Garcinia kola'' nuts, including kolaflavanone, have been described in patent literature.<ref>J Torcol & D Dessolin, {{US patent|3818110}}.</ref>

== References ==
{{reflist}}

{{Flavonoids}}
{{Flavanone}}

[[Category:Flavanones|Flavanones]]
[[Category:Polyols]]
[[Category:Methoxy compounds]]