Kolaflavanone

Kolaflavanone
Identifiers
	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;
CAS Number	68705-66-8 97560-11-7;
PubChem CID	155169;
ChemSpider	136697;
UNII	VY4E467596;
KEGG	C09761;
ChEBI	CHEBI:28521;
ChEMBL	ChEMBL4794351;
CompTox Dashboard (EPA)	DTXSID80243039 ;
Chemical and physical data
Formula	C31H24O12
Molar mass	588.521 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	InChI InChI=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; Key:GJWXCPDVDRIBKP-CNTBMXMRSA-N;

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.^[1]

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.^[2]^[3]^[4] In vitro studies indicate that kolaflavanone may protect neuronal cell lines from toxic insults induced by the herbicide atrazine, a known endocrine-disrupting chemical.^[5]^[6] Kolaflavanone has further been reported to exert antidiabetic effects in experimental models.^[7]

Extraction methods for biflavonoids from Garcinia kola nuts, including kolaflavanone, have been described in patent literature.^[8]

References

^ Farombi EO, Abolaji AO, Farombi TH, Oropo AS, Owoje OA, Awunah MT (February 2018). "Garcinia kola seed biflavonoid fraction (Kolaviron), increases longevity and attenuates rotenone-induced toxicity in Drosophila melanogaster". Pesticide Biochemistry and Physiology. 145: 39–45. Bibcode:2018PBioP.145...39F. doi:10.1016/j.pestbp.2018.01.002. PMID 29482730.
^ Adaramoye OA, Arisekola M (June 2013). "Kolaviron, a biflavonoid complex from Garcinia kola seeds, ameliorates ethanol-induced reproductive toxicity in male wistar rats". Nigerian Journal of Physiological Sciences. 28 (1): 9–15. PMID 23955400.
^ Adedara IA, Farombi EO (May 2012). "Chemoprotection of ethylene glycol monoethyl ether-induced reproductive toxicity in male rats by kolaviron, isolated biflavonoid from Garcinia kola seed". Human & Experimental Toxicology. 31 (5): 506–517. Bibcode:2012HETox..31..506A. doi:10.1177/0960327111424301. PMID 22027498.
^ Adaramoye OA, Adedara IA, Farombi EO (May 2012). "Possible ameliorative effects of kolaviron against reproductive toxicity in sub-lethally whole body gamma-irradiated rats". Experimental and Toxicologic Pathology. 64 (4): 379–385. Bibcode:2012EToxP..64..379A. doi:10.1016/j.etp.2010.10.002. PMID 21036568.
^ Abarikwu SO, Farombi EO, Pant AB (June 2011). "Biflavanone-kolaviron protects human dopaminergic SH-SY5Y cells against atrazine induced toxic insult". Toxicology in Vitro. 25 (4): 848–858. Bibcode:2011ToxVi..25..848A. doi:10.1016/j.tiv.2011.02.005. PMID 21333729.
^ Abarikwu SO, Farombi EO, Kashyap MP, Pant AB (September 2011). "Kolaviron protects apoptotic cell death in PC12 cells exposed to atrazine". Free Radical Research. 45 (9): 1061–1073. doi:10.3109/10715762.2011.593177. PMID 21726175.
^ Adaramoye OA (December 2012). "Antidiabetic effect of kolaviron, a biflavonoid complex isolated from Garcinia kola seeds, in Wistar rats". African Health Sciences. 12 (4): 498–506. doi:10.4314/ahs.v12i4.16. PMC 3598292. PMID 23515095.
^ J Torcol & D Dessolin, U.S. patent 3,818,110.

[1] Farombi EO, Abolaji AO, Farombi TH, Oropo AS, Owoje OA, Awunah MT (February 2018). "Garcinia kola seed biflavonoid fraction (Kolaviron), increases longevity and attenuates rotenone-induced toxicity in Drosophila melanogaster". Pesticide Biochemistry and Physiology. 145: 39–45. Bibcode:2018PBioP.145...39F. doi:10.1016/j.pestbp.2018.01.002. PMID 29482730.

[2] Adaramoye OA, Arisekola M (June 2013). "Kolaviron, a biflavonoid complex from Garcinia kola seeds, ameliorates ethanol-induced reproductive toxicity in male wistar rats". Nigerian Journal of Physiological Sciences. 28 (1): 9–15. PMID 23955400.

[3] Adedara IA, Farombi EO (May 2012). "Chemoprotection of ethylene glycol monoethyl ether-induced reproductive toxicity in male rats by kolaviron, isolated biflavonoid from Garcinia kola seed". Human & Experimental Toxicology. 31 (5): 506–517. Bibcode:2012HETox..31..506A. doi:10.1177/0960327111424301. PMID 22027498.

[4] Adaramoye OA, Adedara IA, Farombi EO (May 2012). "Possible ameliorative effects of kolaviron against reproductive toxicity in sub-lethally whole body gamma-irradiated rats". Experimental and Toxicologic Pathology. 64 (4): 379–385. Bibcode:2012EToxP..64..379A. doi:10.1016/j.etp.2010.10.002. PMID 21036568.

[5] Abarikwu SO, Farombi EO, Pant AB (June 2011). "Biflavanone-kolaviron protects human dopaminergic SH-SY5Y cells against atrazine induced toxic insult". Toxicology in Vitro. 25 (4): 848–858. Bibcode:2011ToxVi..25..848A. doi:10.1016/j.tiv.2011.02.005. PMID 21333729.

[6] Abarikwu SO, Farombi EO, Kashyap MP, Pant AB (September 2011). "Kolaviron protects apoptotic cell death in PC12 cells exposed to atrazine". Free Radical Research. 45 (9): 1061–1073. doi:10.3109/10715762.2011.593177. PMID 21726175.

[7] Adaramoye OA (December 2012). "Antidiabetic effect of kolaviron, a biflavonoid complex isolated from Garcinia kola seeds, in Wistar rats". African Health Sciences. 12 (4): 498–506. doi:10.4314/ahs.v12i4.16. PMC 3598292. PMID 23515095.

[8] J Torcol & D Dessolin, U.S. patent 3,818,110.

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Kolaflavanone

References

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