Pomiferin
Pomiferin
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| Names | |
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| IUPAC name
3-(3,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one
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| Other names
Pomiferin
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C25H24O6 | |
| Molar mass | 420.45446 g/mol |
| Density | 1.314g/cm3 |
| Boiling point | 673.5°C at 760 mmHg |
| DMSO, Acetone | |
| Hazards | |
| Flash point | 233.3°C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pomiferin is a prenylated isoflavone that can be found along with osajin in the fruits and female flowers of the osage orange tree (Maclura pomifera). ( the female flowers of this tree contain 0.38% Pomiferin, and the Osage orange fruit contains 13.6% Pomiferin )
Pomiferin was identified, and named in 1939 by Melville. L. Wolfrom (The Ohio State University)[1]. In 1941 Professor Wolfram classified pomiferin as an isoflavone and in 1946 he published the complete structure of Pomiferin[2]. In 2003 The crystal structure of pomiferin (3-(3,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-enyl)-4H,8H-pyrano[2,3-h]chromen-4-one), C25H24O6 was reported by Marek, J.[3]
In recent research Pomiferin has demonstrated efficacy as an antioxidant , cardioprotectant, antimicrobial, antidiabetic , PDE5 inhibitor and cytotoxicity for several cancer cell lines.
Research
The prenylated isoflavonoid , pomiferin, has been the subject of many research studies. One area that is not listed below is the use of pomiferin as an insecticide . Peterson and Fristad (2000) Investigated the folklore that the osage orange fruit repels insects. They tested the repellency of purified pomiferin and osajin using the Maize Weevil and they concluded that the pure pomiferin had little or no effect and that there must be another component of the Osage orange that repells incects[4]
The following research is focused on the uses of pomiferin that have provided positive results or significant biological applications.
Antioxidant
pomiferin, has shown antioxidant activity in the inhibition of lipid peroxidation and the reduction of free radicals, reactive oxygen species (ROS) and other unstable molecules. Tsao and Yang (2003)[5] reported that Pomiferin was found to be a strong antioxidant , comparable to the antioxidant vitamins C and E and the synthetic antioxidant BHT.[6]
Cardioprotectant
Necas and Bartosikova (2007) reported that the flavonoid pomiferin has been shown to have potent cardioprotective effect on rat hearts subjected to ischemia and reperfusion injury The mechanism for this protection may occur through the inhibition of lipid peroxidation.[7]
Antimicrobial
Mahmoud (1981)[8]indicated that pomiferin, exhibited interesting antibacterial activity against E. coli (12.5 μg/ml, ) and Salmonella gallinarum (25 μg/ml ) and to moderately inhibited Mycobacterium smegmatis (6.25 μg/ml )
Antidiabetic
Bartosíková , Necas (2007), conducted a biochemical examination that showed a protective antioxidative and antidiabetic effect of pomiferin.[9]
Moon(2014) presented the results of a study that evaluated the antidiabetic effect of osajin and pomiferin from the Osage orange in normal and streptozotocin-induced diabetic rats. Pomiferin in the streptozotocin-induced diabetic effects showed significant hypoglycemic activity for 14 days significantly decreased the serum glucose, triglyceride while it increased the serum insulin in diabetic rats [10]
PDE5 inhibitor
Anti-cancer activity
Svasti (2005)[11]observed that pomiferin induced apoptosis and differentiation in cholangiocarcinoma cell line HuCCA-1.
References
- ^ Wolfram, Melville (1939). "Isolation of a New Pigment, Pomiferin," (PDF). J. Amer. Chem. Soc. 61: 2832–2836. Retrieved 9 August 2015.
- ^ Wolfram, Melville (1946). ". Complete Structures of Osajin and Pomiferin" (PDF). J. Amer. Chem. Soc. 68: 406–418. Retrieved 9 August 2015.
- ^ "Pomiferin". PubMed. Retrieved 10 August 2015.
- ^ Peterson, Chris (1 December 2000). "Osajin and Pomiferin, Two Isoflavones Purified from Osage Orange Fruits, Tested for Repellency to the Maize Weevil (Coleoptera: Curculionidae)". Environmental Entomology Journal: 1133–1137. doi:10.1603/0046-225X-29.6.1133. Retrieved 15 August 2015.
- ^ Tsao, Rong (2003). "Antioxidant Isoflavones in Osage Orange, Maclura pomifera (Raf.) Schneid". Journal of Agriculture and Food Chemistry. 51 (22): 6445–6451. doi:10.1021/jf0342369.
- ^ Schall, E.D. (1956). "The antioxidants of the osage orange fruit". J. Am Oil Chem. Soc. 33: 80–82. doi:10.1007/BF02612556. Retrieved 15 August 2015.
- ^ J. Nečas, J. (2007). "Protective Effects of Flavonoid Pomiferin on Heart Ischemia-Reperfusion". Acta Vet. Brno. 76 (3): 363–370. doi:10.2754/avb200776030363. Retrieved 16 August 2015.
- ^ Mahmoud, F.Z. "Antimicrobial components from Maclura pomifera fruit". PubMed. Retrieved 19 August 2015.
- ^ Bartosíková, L. "Examination of the antioxidative and antidiabetic effect of pomiferin in alloxan-induced diabetes mellitus in". PubMed. Ceska Slov Farm. 2007. Retrieved 19 August 2015.
- ^ Moon, H. I. "Effect of osajin and pomiferin on antidiabetic effects from normal and streptozotocin-induced diabetic rats". PubMed. Nat Prod Commun. 2014 Dec;9(12):1723-4. Retrieved 19 August 2015.
- ^ Svasti, J. "Proteomic profiling of cholangiocarcinoma cell line treated with pomiferin from Derris malaccensis". PubMed. Proteomics. 2005 Nov;5(17):4504-9. Retrieved 22 August 2015.