{{medref|date=August 2024}} {{Chembox | ImageFile = Pomiferin.svg | ImageSize = 200px | ImageAlt = Pomiferin | IUPACName = 3′,4′,5-Trihydroxy-6′′,6′′-dimethyl-6-(3-methylbut-2-en-1-yl)-6′′''H''-pyrano[2′′,3′′:7,8]isoflavone | SystematicName = 3-(3,4-Dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4''H'',8''H''-(benzo[1,2-''b'':3,4-''b''′]dipyran)-4-one | OtherNames = Pomiferin | Section1 = {{Chembox Identifiers | CASNo = 572-03-2 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 74YIS40APM | PubChem = CID: 4871
| ChemSpiderID = 4705 | SMILES = CC(=CCc1c(c2c(=O)c(coc2c3c1OC(C=C3)(C)C)c4ccc(c(c4)O)O)O)C | InChI = 1/C25H24O6/c1-13(2)5-7-15-21(28)20-22(29)17(14-6-8-18(26)19(27)11-14)12-30-24(20)16-9-10-25(3,4)31-23(15)16/h5-6,8-12,26-28H,7H2,1-4H3 | InChIKey = GHCZYXUOYFOXIP-UHFFFAOYAP | StdInChI = 1S/C25H24O6/c1-13(2)5-7-15-21(28)20-22(29)17(14-6-8-18(26)19(27)11-14)12-30-24(20)16-9-10-25(3,4)31-23(15)16/h5-6,8-12,26-28H,7H2,1-4H3 | StdInChIKey = GHCZYXUOYFOXIP-UHFFFAOYSA-N
}} | Section2 = {{Chembox Properties | C = 25 | H = 24 | O = 6 | Appearance = | Density = 1.314 g/cm<sup>3</sup> | MeltingPt = | BoilingPt = | SolubleOther = Soluble | Solvent = DMSO, acetone }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = 233.3 °C{{cn|date=August 2024}} | AutoignitionPt = }} }}
'''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'').<ref name="Food Chem Toxicol. 2009 Aug;47(8):1747-51">{{cite journal|last1=Orhan|first1=I|title=Cholinesterase inhibitory effects of the extracts and compounds of Maclura pomifera (Rafin.) Schneider |journal=Food and Chemical Toxicology|volume=47|issue=8|pages=1747–51|pmid=19394400|year=2009|doi=10.1016/j.fct.2009.04.023}}</ref>
Pomiferin was identified and named in 1939 by Melville L. Wolfrom from Ohio State University.<ref>{{cite journal|last1=Wolfrom|first1=Melville|title=Isolation of a New Pigment, Pomiferin|journal=J. Am. Chem. Soc.|date=1939|volume=61|issue=10|pages=2832–2836|url=http://www.nasonline.org/publications/biographical-memoirs/memoir-pdfs/wolfrom-melville-l.pdf|access-date=9 August 2015|doi=10.1021/ja01265a079}}</ref> In 1941, Wolfram classified pomiferin as an isoflavone and in 1946 published the complete structure of pomiferin.<ref name="Journal of the American Chemical Society">{{cite journal|last1=Wolfrom|first1=Melville|title=. Complete Structures of Osajin and Pomiferin|journal=J. Am. Chem. Soc.|date=1946|volume=68|issue=3|pages=406–418|url=http://www.nasonline.org/publications/biographical-memoirs/memoir-pdfs/wolfrom-melville-l.pdf|access-date=9 August 2015|doi=10.1021/ja01207a021|pmid=21015734}}</ref> In 2003, the crystal structure of pomiferin was reported by J. Marek.<ref>{{cite journal|title= Pomiferin| pmid=12711784 | volume=59 | issue=Pt 3 | journal=Acta Crystallogr C| pages=o127–8 | last1 = Marek | first1 = J | last2 = Veselá | first2 = D | last3 = Lisková | first3 = M | last4 = Zemlicka | first4 = M | doi=10.1107/s0108270103002300| year=2003 | bibcode=2003AcCrC..59O.127M }}</ref>
In recent research pomiferin has demonstrated efficacy as an antioxidant, cardioprotectant, antimicrobial, antidiabetic, PDE5 inhibitor, and cytotoxicity for several cancer cell lines.
==Research==
===Repellent=== Peterson and Fristad (2000) investigated folklore beliefs stating that osage orange fruit repelled insects. They concluded that pure pomiferin had little or no effect and that there must be another component of the Osage orange that repels insects.<ref name="Oxford University press">{{cite journal|last1=Peterson|first1=Chris|title=Osajin and Pomiferin, Two Isoflavones Purified from Osage Orange Fruits, Tested for Repellency to the Maize Weevil (Coleoptera: Curculionidae)|journal=Environmental Entomology|date=1 December 2000|pages=1133–1137|doi=10.1603/0046-225X-29.6.1133|volume=29|issue=6|s2cid=4889925 |url=https://lib.dr.iastate.edu/ent_pubs/328 |doi-access=free}}</ref>
===Antioxidant=== Pomiferin has shown antioxidant activity via inhibition of lipid peroxidation and the reduction of free radicals, reactive oxygen species and other unstable molecules. Tsao and Yang (2003)<ref name="ACS Publications">{{cite journal|last1=Tsao|first1=Rong|title=Antioxidant Isoflavones in Osage Orange, Maclura pomifera (Raf.) Schneid|journal=Journal of Agricultural and Food Chemistry|date=2003|volume=51|issue=22|pages=6445–6451|doi=10.1021/jf0342369|pmid=14558760|bibcode=2003JAFC...51.6445T }}</ref> reported that Pomiferin was found to be a strong antioxidant, comparable to the vitamins C and E and the synthetic antioxidant BHT.<ref name=ReserchGate>{{cite journal|last1=Schall|first1=E.D.|title=The antioxidants of the osage orange fruit|journal=J. Am. Oil Chem. Soc.|date=1956|volume=33|issue=2|pages=80–82|doi=10.1007/BF02612556|s2cid=85143867 |url=https://www.researchgate.net/publication/225498247|access-date=15 August 2015}}</ref>
===Cardioprotectant=== Necas and Bartosíková (2007) reported that the chemical had 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.<ref name="Journal of the University of Veterinary and Pharmaceutical Sciences in Brno, Czech Republic">{{cite journal|last1=J. Nečas|first1=J.|title=Protective Effects of Flavonoid Pomiferin on Heart Ischemia-Reperfusion|journal=Acta Vet. Brno|date=2007|volume=76|issue=3|pages=363–370|doi=10.2754/avb200776030363|doi-access=free}}</ref>
===Antimicrobial=== Mahmoud (1981)<ref name="Planta Med. 1981 Jul;42(3):299-301.">{{cite journal|last1=Mahmoud|first1=F.Z.|title=Antimicrobial components from Maclura pomifera fruit |pmid=7280089|volume=42|issue=3|journal=Planta Med|pages=299–301|doi=10.1055/s-2007-971646|year=1981|bibcode=1981PlMed..42..299M }}</ref> indicated that pomiferin exhibited antibacterial activity against ''E. coli'' and ''Salmonella gallinarum'', as well as ''Mycobacterium smegmatis'' to a lesser extent.
===Antidiabetic=== Bartosíková and Necas (2007), furthermore, conducted a biochemical examination showing antioxidative and antidiabetic effects of pomiferin.<ref name="Ceska Slov Farm. 2007 Jun;56(3):135-40.">{{cite journal|last1=Bartosíková|first1=L|title=Examination of the antioxidative and antidiabetic effect of pomiferin in alloxan-induced diabetes mellitus in|journal=Ceska Slov Farm |year=2007 |pmid=17867526|volume=56|issue=3|pages=135–40}}</ref>
Moon (2014) presented 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 rats resulted in significant hypoglycemic activity for 14 days following, by decreasing the serum glucose and triglycerides while increasing serum insulin in those rats.<ref name="Nat Prod Commun">{{cite journal|last1=Moon|first1=H. I.|title=Effect of osajin and pomiferin on antidiabetic effects from normal and streptozotocin-induced diabetic rats |journal=Nat Prod Commun |pmid=25632468|volume=9|issue=12|pages=1723–4|year=2014}}</ref>
===PDE5 inhibitor=== Ribaudo (2015)<ref name=PubMed>{{cite journal|last1=Ribaudo|first1=G.|title=Semi-synthetic derivatives of natural isoflavones from Maclura pomifera as a novel class of PDE-5A inhibitors |journal=Fitoterapia|date=2015|volume=105|pages=132–138|doi=10.1016/j.fitote.2015.06.020|pmid=26136059}}</ref> proposed pomiferin and osajin as potential lead compounds for the development, starting from natural scaffolds, of a new class of PDE-5A inhibitors with vasorelaxant properties to treat pulmonary hypertension and erectile dysfunction.
===Anti-cancer activity=== Svasti (2005)<ref name="Proteomics. 2005 Nov;5(17):4504-9.">{{cite journal|last1=Svasti|first1=J.|title=Proteomic profiling of cholangiocarcinoma cell line treated with pomiferin from Derris malaccensis |journal=Proteomics |pmid=16220529|doi=10.1002/pmic.200401315|volume=5|issue=17|pages=4504–9|year=2005|s2cid=38899441 }}</ref> observed that pomiferin induced apoptosis and differentiation in cholangiocarcinoma cell line HuCCA-1, albeit at the therapeutically unrealistic dose of 0.9 μg/mL.
== References == {{Reflist}}
==Further reading== *{{cite journal | last1 = Son | first1 = Il Hong |display-authors=etal | year = 2007 | title = Pomiferin, histone deacetylase inhibitor isolated from the fruits of Maclura pomifera | journal = Bioorganic & Medicinal Chemistry Letters | volume = 17 | issue = 17| pages = 4753–4755 | doi=10.1016/j.bmcl.2007.06.060| pmid = 17662606 }} *{{cite journal | last1 = Svasti | first1 = Jisnuson |display-authors=etal | year = 2005 | title = Proteomic profiling of cholangiocarcinoma cell line treated with pomiferin from Derris malaccensis | journal = Proteomics | volume = 5 | issue = 17| pages = 4504–4509 | doi=10.1002/pmic.200401315 | pmid=16220529| s2cid = 38899441 }} *{{cite journal | last1 = Veselá | first1 = Dagmar |display-authors=etal | year = 2004 | title = Antioxidative and EROD activities of osajin and pomiferin | journal = Fitoterapia | volume = 75 | issue = 2| pages = 209–211 | doi=10.1016/j.fitote.2003.12.005| pmid = 15030927 }} *{{cite journal | last1 = Marek | first1 = Jaromir |display-authors=etal | year = 2003 | title = Pomiferin | doi = 10.1107/S0108270103002300 | pmid = 12711784 | journal = Acta Crystallographica Section C | volume = 59 | issue = 3| pages = 127–128 | bibcode = 2003AcCrC..59O.127M }}
Category:Isoflavones