Kolaflavanone

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.

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

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

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.