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''). Pomiferin was identified and named in 1939 by Melville L. Wolfrom from

Ohio State University The Ohio State University (Ohio State or OSU) is a public university, public Land-grant university, land-grant research university in Columbus, Ohio, United States. A member of the University System of Ohio, it was founded in 1870. It is one ...

. In 1941, Wolfram classified pomiferin as an isoflavone and in 1946 published the complete

structure A structure is an arrangement and organization of interrelated elements in a material object or system, or the object or system so organized. Material structures include man-made objects such as buildings and machines and natural objects such as ...

of pomiferin. In 2003, the crystal structure of pomiferin was reported by J. Marek. In recent research pomiferin has demonstrated efficacy as an antioxidant, cardioprotectant, antimicrobial, antidiabetic,

PDE5 inhibitor A phosphodiesterase type 5 inhibitor (PDE5 inhibitor) is a vasodilating medication, drug that works by blocking the degradative action of cGMP-specific phosphodiesterase type 5 (PDE5) on cyclic GMP in the smooth muscle cells lining the blood vess ...

, and cytotoxicity for several cancer

cell line An immortalised cell line is a population of cells from a multicellular organism that would normally not proliferate indefinitely but, due to mutation, have evaded normal cellular senescence and instead can keep undergoing division. The cells ...

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.

Antioxidant

Pomiferin has shown

antioxidant Antioxidants are Chemical compound, compounds that inhibit Redox, oxidation, a chemical reaction that can produce Radical (chemistry), free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants ...

activity via inhibition of

lipid peroxidation Lipid peroxidation, or lipid oxidation, is a complex chemical process that leads to oxidative degradation of lipids, resulting in the formation of peroxide and hydroperoxide derivatives.{{Cite journal , last1=Ayala , first1=Antonio , last2=Muñoz ...

and the reduction of

free radical A daughter category of ''Ageing'', this category deals only with the biological aspects of ageing. Ageing Biogerontology Biological processes Causes of death Cellular processes Gerontology Life extension Metabolic disorders Metabolism ...

reactive oxygen species In chemistry and biology, reactive oxygen species (ROS) are highly Reactivity (chemistry), reactive chemicals formed from diatomic oxygen (), water, and hydrogen peroxide. Some prominent ROS are hydroperoxide (H2O2), superoxide (O2−), hydroxyl ...

and other unstable molecules. Tsao and Yang (2003) reported that Pomiferin was found to be a strong antioxidant, comparable to the vitamins C and E and the synthetic antioxidant BHT.

Cardioprotectant

Necas and Bartosíková (2007) reported that the chemical had potent cardioprotective effect on rat hearts subjected to

ischemia Ischemia or ischaemia is a restriction in blood supply to any tissue, muscle group, or organ of the body, causing a shortage of oxygen that is needed for cellular metabolism (to keep tissue alive). Ischemia is generally caused by problems ...

and

reperfusion injury Reperfusion injury, sometimes called ischemia-reperfusion injury (IRI) or reoxygenation injury, is the tissue damage caused when blood supply returns to tissue ('' re-'' + ''perfusion'') after a period of ischemia or lack of oxygen (anoxia or hy ...

. The mechanism for this protection may occur through the inhibition of

Antimicrobial

Mahmoud (1981) indicated that pomiferin exhibited

antibacterial An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention ...

activity against ''

E. coli ''Escherichia coli'' ( )Wells, J. C. (2000) Longman Pronunciation Dictionary. Harlow ngland Pearson Education Ltd. is a gram-negative, facultative anaerobic, rod-shaped, coliform bacterium of the genus ''Escherichia'' that is commonly foun ...

'' and '' Salmonella gallinarum'', as well as ''

Mycobacterium smegmatis ''Mycobacterium smegmatis'' is an acid-fast bacterium, bacterial species in the phylum ''Actinomycetota'' and the genus ''Mycobacterium''. It is 3.0 to 5.0 μm long with a bacillus (shape), bacillus shape and can be stained by Ziehl–Neels ...

'' to a lesser extent.

Antidiabetic

Bartosíková and Necas (2007), furthermore, conducted a biochemical examination showing antioxidative and

antidiabetic Drugs used in diabetes treat types of diabetes mellitus by decreasing glucose levels in the blood. With the exception of insulin, most GLP-1 receptor agonists ( liraglutide, exenatide, and others), and pramlintide, all diabetes medications a ...

effects of pomiferin. Moon (2014) presented results of a study that evaluated the antidiabetic effect of osajin and pomiferin from the Osage orange in normal and

streptozotocin Streptozotocin or streptozocin ( INN, USP) (STZ) is a naturally occurring alkylating antineoplastic agent that is particularly toxic to the insulin-producing beta cells of the pancreas in mammals. It is used in medicine for treating certain can ...

-induced diabetic rats. Pomiferin in the streptozotocin-induced diabetic rats resulted in significant

hypoglycemic Hypoglycemia (American English), also spelled hypoglycaemia or hypoglycæmia (British English), sometimes called low blood sugar, is a fall in blood sugar to levels below normal, typically below 70 mg/dL (3.9 mmol/L). Whipple's tria ...

activity for 14 days following, by decreased the serum glucose and

triglyceride A triglyceride (from '' tri-'' and '' glyceride''; also TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates ...

s while increasing serum

insulin Insulin (, from Latin ''insula'', 'island') is a peptide hormone produced by beta cells of the pancreatic islets encoded in humans by the insulin (''INS)'' gene. It is the main Anabolism, anabolic hormone of the body. It regulates the metabol ...

in those rats.

PDE5 inhibitor

Ribaudo (2015) 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 Pulmonary hypertension (PH or PHTN) is a condition of increased blood pressure in the pulmonary artery, arteries of the lungs. Symptoms include dypsnea, shortness of breath, Syncope (medicine), fainting, tiredness, chest pain, pedal edema, swell ...

and

erectile dysfunction Erectile dysfunction (ED), also referred to as impotence, is a form of sexual dysfunction in males characterized by the persistent or recurring inability to achieve or maintain a Human penis, penile erection with sufficient rigidity and durat ...

Anti-cancer activity

Svasti (2005) observed that pomiferin induced

apoptosis Apoptosis (from ) is a form of programmed cell death that occurs in multicellular organisms and in some eukaryotic, single-celled microorganisms such as yeast. Biochemistry, Biochemical events lead to characteristic cell changes (Morphology (biol ...

and differentiation in

cholangiocarcinoma Cholangiocarcinoma, also known as bile duct cancer, is a type of cancer that forms in the bile ducts. Symptoms of cholangiocarcinoma may include abdominal pain, yellowish skin, weight loss, generalized itching, and fever. Light colored stoo ...

cell line HuCCA-1. Son (2007) investigated the growth-inhibitory activity of pomiferin compared to SAHA (suberoylanilide hydroxamic acid). Pomiferin exhibited

cytotoxicity Cytotoxicity is the quality of being toxic to cells. Examples of toxic agents are toxic metals, toxic chemicals, microbe neurotoxins, radiation particles and even specific neurotransmitters when the system is out of balance. Also some types of d ...

effects on six cancer cells lines:

kidney In humans, the kidneys are two reddish-brown bean-shaped blood-filtering organ (anatomy), organs that are a multilobar, multipapillary form of mammalian kidneys, usually without signs of external lobulation. They are located on the left and rig ...

( ACHN),

lung The lungs are the primary Organ (biology), organs of the respiratory system in many animals, including humans. In mammals and most other tetrapods, two lungs are located near the Vertebral column, backbone on either side of the heart. Their ...

( NCI-H23),

prostate The prostate is an male accessory gland, accessory gland of the male reproductive system and a muscle-driven mechanical switch between urination and ejaculation. It is found in all male mammals. It differs between species anatomically, chemica ...

( PC-3),

breast The breasts are two prominences located on the upper ventral region of the torso among humans and other primates. Both sexes develop breasts from the same embryology, embryological tissues. The relative size and development of the breasts is ...

(

MDA-MB-231 Scientists study the behaviour of isolated cells grown in the laboratory for insights into how cells function in the body in health and disease. Experiments using cell culture are used for developing new diagnostic tests and new treatments for dise ...

melanoma Melanoma is the most dangerous type of skin cancer; it develops from the melanin-producing cells known as melanocytes. It typically occurs in the skin, but may rarely occur in the mouth, intestines, or eye (uveal melanoma). In very rare case ...

( LOX-IMVI), and colon ( HCT-15).