Pomiferin

Last updated
Pomiferin
Pomiferin.svg
Names
IUPAC name
3′,4′,5-Trihydroxy-6′′,6′′-dimethyl-6-(3-methylbut-2-en-1-yl)-6′′H-pyrano[2′′,3′′:7,8]isoflavone
Systematic IUPAC name
3-(3,4-Dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4H,8H-(benzo[1,2-b:3,4-b′]dipyran)-4-one
Other names
Pomiferin
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=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
    Key: GHCZYXUOYFOXIP-UHFFFAOYSA-N
  • 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
    Key: GHCZYXUOYFOXIP-UHFFFAOYAP
  • CC(=CCc1c(c2c(=O)c(coc2c3c1OC(C=C3)(C)C)c4ccc(c(c4)O)O)O)C
Properties
C25H24O6
Molar mass 420.461 g·mol−1
Density 1.314 g/cm3
Solubility in DMSO, acetoneSoluble
Hazards
Flash point 233.3 °C[ citation needed ]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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). [1]

Contents

Pomiferin was identified and named in 1939 by Melville L. Wolfrom from Ohio State University. [2] In 1941, Wolfram classified pomiferin as an isoflavone and in 1946 published the complete structure of pomiferin. [3] In 2003, the crystal structure of pomiferin was reported by J. Marek. [4]

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. [5]

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) [6] reported that Pomiferin was found to be a strong antioxidant, comparable to the vitamins C and E and the synthetic antioxidant BHT. [7]

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. [8]

Antimicrobial

Mahmoud (1981) [9] 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. [10]

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 decreased the serum glucose and triglycerides while increasing serum insulin in those rats. [11]

PDE5 inhibitor

Ribaudo (2015) [12] 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) [13] observed that pomiferin induced apoptosis and differentiation in cholangiocarcinoma cell line HuCCA-1.

Son (2007) [14] investigated the growth-inhibitory activity of pomiferin compared to SAHA (suberoylanilide hydroxamic acid). Pomiferin exhibited cytotoxicity effects on six cancer cells lines: kidney (ACHN), lung (NCI-H23), prostate (PC-3), breast (MDA-MB-231), melanoma (LOX-IMVI), and colon (HCT-15).

Related Research Articles

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<i>Maclura pomifera</i> Species of plant

Maclura pomifera, commonly known as the Osage orange, is a small deciduous tree or large shrub, native to the south-central United States. It typically grows about 8 to 15 metres (30–50 ft) tall. The distinctive fruit, a multiple fruit, is roughly spherical, bumpy, 8 to 15 centimetres (3–6 in) in diameter, and turns bright yellow-green in the fall. The fruits secrete a sticky white latex when cut or damaged. Despite the name "Osage orange", it is not related to the orange. It is a member of the mulberry family, Moraceae. Due to its latex secretions and woody pulp, the fruit is typically not eaten by humans and rarely by foraging animals. Ecologists Daniel H. Janzen and Paul S. Martin proposed in 1982 that the fruit of this species might be an example of what has come to be called an evolutionary anachronism—that is, a fruit coevolved with a large animal seed dispersal partner that is now extinct. This hypothesis is controversial.

<span class="mw-page-title-main">Flavonoid</span> Class of plant and fungus secondary metabolites

Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.

<span class="mw-page-title-main">Gingerol</span> Chemical compound

Gingerol ([6]-gingerol) is a phenolic phytochemical compound found in fresh ginger that activates heat receptors on the tongue. It is normally found as a pungent yellow oil in the ginger rhizome, but can also form a low-melting crystalline solid. This chemical compound is found in all members of the Zingiberaceae family and is high in concentrations in the grains of paradise as well as an African Ginger species.

<i>Maclura</i> Genus of flowering plants

Maclura is a genus of flowering plants in the mulberry family, Moraceae. It includes the inedible Osage orange, which is used as mosquito repellent and grown throughout the United States as a hedging plant. It is dioecious, with male and female flowers borne on separate plants.

<span class="mw-page-title-main">Genistein</span> Chemical compound

Genistein (C15H10O5) is a naturally occurring compound that structurally belongs to a class of compounds known as isoflavones. It is described as an angiogenesis inhibitor and a phytoestrogen.

<span class="mw-page-title-main">Ursolic acid</span> Pentacyclic chemical compound found in fruits

Ursolic acid, is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme.

<i>Ficus deltoidea</i> Species of Asian plant known as the mistletoe fig

Ficus deltoidea, commonly known as mistletoe fig is a species of flowering plant in the family Moraceae, native to Southeast Asia, and widely naturalized in other parts of the world.

<span class="mw-page-title-main">Fisetin</span> Chemical compound

Fisetin (7,3′,4′-flavon-3-ol) is a plant flavonol from the flavonoid group of polyphenols. It can be found in many plants, where it serves as a yellow/ochre colouring agent. It is also found in many fruits and vegetables, such as strawberries, apples, persimmons, onions and cucumbers. Its chemical formula was first described by Austrian chemist Josef Herzig in 1891.

<span class="mw-page-title-main">Morin (flavonol)</span> Chemical compound

Morin is a yellow chemical compound that can be isolated from Maclura pomifera (Osage orange), Maclura tinctoria (old fustic), and from leaves of Psidium guajava (common guava). In a preclinical in vitro study, morin was found to be a weak inhibitor of fatty acid synthase with an IC50 of 2.33 μM. Morin was also found to inhibit amyloid formation by islet amyloid polypeptide (or amylin) and disaggregate amyloid fibers.

<span class="mw-page-title-main">Dihydromorin</span> Chemical compound

Dihydromorin is a flavanonol, a type of flavonoid. It can be found in plants of the family Moraceae including Morus nigra, in Morus alba, Maclura pomifera, in the jackfruit and in Artocarpus dadah.

<i>Ichnocarpus frutescens</i> Species of flowering plant

Ichnocarpus frutescens is a species of flowering plant in the dogbane family Apocynaceae, known by the English common name black creeper. It is native to much of China, India, Southeast Asia, and northern Australia.

<span class="mw-page-title-main">Syringin</span> Chemical compound

Syringin is a natural chemical compound first isolated from the bark of lilac by Meillet in 1841. It has since been found to be distributed widely throughout many types of plants. It is also called eleutheroside B, and is found in Eleutherococcus senticosus. It is also found in dandelion coffee. Syringin may potentially have antidiabetic effects.

<span class="mw-page-title-main">Jacalin-like lectin domain</span>

In molecular biology, the jacalin-like lectin domain is a mannose-binding lectin domain with a beta-prism fold consisting of three 4-stranded beta-sheets, with an internal pseudo 3-fold symmetry. Some lectins in this group stimulate distinct T- and B-cell functions, such as Jacalin, which binds to the T-antigen and acts as an agglutinin. This domain is found in 1 to 6 copies in lectins. The domain is also found in the salt-stress induced protein from rice and an animal prostatic spermine-binding protein.

<i>Pluchea indica</i> Species of plant

Pluchea indica is a species of flowering plant in the aster family, Asteraceae. Its common names include Indian camphorweed, Indian fleabane, and Indian pluchea. It is native to parts of Asia and Australia, and it is widespread in the Pacific Islands as an introduced and often invasive species.

<span class="mw-page-title-main">Methyl caffeate</span> Chemical compound

Methyl caffeate is an ester of caffeic acid, a naturally occurring phenolic compound. It is an α-glucosidase inhibitor. Its physical form is a powder.

<i>Helicteres isora</i> Species of flowering plant

Helicteres isora, sometimes called the Indian screw tree, is a small tree or large shrub found in southern Asia and northern Oceania. It is usually assigned to the family Malvaceae, but it is sometimes assigned to the family Sterculiaceae. The red flowers are pollinated mainly by sunbirds, butterflies, and Hymenoptera. In the 19th century fibers from the bark were used to make rope and sacks, although nowadays the tree is harvested for the fruits and roots which are used in folk medicine.

<i>Saururus chinensis</i> Species of flowering plant in the family Saururaceae

Saururus chinensis, commonly known as Asian lizard's tail, is an herb that grows in low, damp places to more than 1 meter high, endemic to China, India, Japan, Korea, Philippines, and Vietnam. Its leaves are green, papery, ribbed, densely glandular, and ovate to ovate-lanceolate, and (4-)10-20 × (2-)5-10 cm in size. Each flower spike resembles a lizard's tail.

<span class="mw-page-title-main">Geniposide</span> Chemical compound

Geniposide, the glycoside form of genipin, is a bioactive iridoid glycoside that is found in a wide variety of medicinal herbs, such as Gardenia jasminoides (fruits) . Geniposide shows several pharmacological effects including neuroprotective, antidiabetic, hepatoprotective, anti-inflammatory, analgesic, antidepressant-like, cardioprotective, antioxidant, immune-regulatory, antithrombotic and antitumoral activity. These pharmacology benefits arise through the modulating action of geniposide on several proteins and genes that are associated with inflammatory and oxidative stress processes.

<span class="mw-page-title-main">Sekikaic acid</span> Chemical compound found in some lichens

Sekikaic acid is an organic compound in the structural class of chemicals known as depsides. It is found in some lichens. First isolated from Ramalina sekika, it is a fairly common lichen product in Ramalina and Cladonia, both genera of lichen-forming fungi. The species epithet of the powdery lichen Lepraria sekikaica refers to the presence of this substance—a rarity in genus Lepraria.

References

  1. Orhan, I (2009). "Cholinesterase inhibitory effects of the extracts and compounds of Maclura pomifera (Rafin.) Schneider". Food and Chemical Toxicology. 47 (8): 1747–51. doi:10.1016/j.fct.2009.04.023. PMID   19394400.
  2. Wolfrom, Melville (1939). "Isolation of a New Pigment, Pomiferin" (PDF). J. Am. Chem. Soc. 61 (10): 2832–2836. doi:10.1021/ja01265a079 . Retrieved 9 August 2015.
  3. Wolfrom, Melville (1946). ". Complete Structures of Osajin and Pomiferin" (PDF). J. Am. Chem. Soc. 68 (3): 406–418. doi:10.1021/ja01207a021. PMID   21015734 . Retrieved 9 August 2015.
  4. Marek, J; Veselá, D; Lisková, M; Zemlicka, M (2003). "Pomiferin". Acta Crystallogr C. 59 (Pt 3): o127–8. Bibcode:2003AcCrC..59O.127M. doi:10.1107/s0108270103002300. PMID   12711784.
  5. 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. 29 (6): 1133–1137. doi: 10.1603/0046-225X-29.6.1133 . S2CID   4889925.
  6. Tsao, Rong (2003). "Antioxidant Isoflavones in Osage Orange, Maclura pomifera (Raf.) Schneid". Journal of Agricultural and Food Chemistry. 51 (22): 6445–6451. doi:10.1021/jf0342369. PMID   14558760.
  7. Schall, E.D. (1956). "The antioxidants of the osage orange fruit". J. Am. Oil Chem. Soc. 33 (2): 80–82. doi:10.1007/BF02612556. S2CID   85143867 . Retrieved 15 August 2015.
  8. J. Nečas, J. (2007). "Protective Effects of Flavonoid Pomiferin on Heart Ischemia-Reperfusion". Acta Vet. Brno. 76 (3): 363–370. doi: 10.2754/avb200776030363 .
  9. Mahmoud, F.Z. (1981). "Antimicrobial components from Maclura pomifera fruit". Planta Med. 42 (3): 299–301. doi:10.1055/s-2007-971646. PMID   7280089.
  10. Bartosíková, L (2007). "Examination of the antioxidative and antidiabetic effect of pomiferin in alloxan-induced diabetes mellitus in". Ceska Slov Farm. 56 (3): 135–40. PMID   17867526.
  11. Moon, H. I. (2014). "Effect of osajin and pomiferin on antidiabetic effects from normal and streptozotocin-induced diabetic rats". Nat Prod Commun. 9 (12): 1723–4. PMID   25632468.
  12. Ribaudo, G. (2015). "Semi-synthetic derivatives of natural isoflavones from Maclura pomifera as a novel class of PDE-5A inhibitors". Fitoterapia. 105: 132–138. doi:10.1016/j.fitote.2015.06.020. PMID   26136059.
  13. Svasti, J. (2005). "Proteomic profiling of cholangiocarcinoma cell line treated with pomiferin from Derris malaccensis". Proteomics. 5 (17): 4504–9. doi:10.1002/pmic.200401315. PMID   16220529. S2CID   38899441.
  14. Son, Il Hong. "Pomiferin, histone deacetylase inhibitor isolated from the fruits of Maclura pomifera" (PDF). personal.evangel.edu. Retrieved 22 August 2015.

Further reading