Naringenin
Encyclopedia
Naringenin is a flavanone
, a type of flavonoid, that is considered to have a bioactive effect on human health as antioxidant
, free radical scavenger, anti-inflammatory
, carbohydrate
metabolism
promoter, and immune system
modulator. It is the predominant flavanone
in grapefruit
.
in vitro
. Scientists exposed cells to 80 micromoles of naringenin per liter, for 24 hours, and found that the amount of hydroxyl damage to the DNA was reduced by 24% in that very short period of time.
Naringenin found in grapefruit juice has been shown to have an inhibitory effect on the human cytochrome P450 isoform CYP1A2
, which can change pharmacokinetics
in a human (or orthologous
) host of several popular drugs in an adverse manner, even resulting in carcinogens of otherwise harmless substances.
Naringenin has also been shown to reduce hepatitis C
virus production by infected hepatocyte
s (liver cells) in cell culture
. This seem to be secondary to Naringenin ability to inhibit the secretion of very-low-density lipoprotein
by the cells. The antiviral effects of naringenin are currently under clinical investigation.
Naringenin seems to protect LDLR-deficient mice from the obesity effects of a high-fat diet.
Naringenin lowers the plasma and hepatic cholesterol
concentrations by suppressing HMG-CoA reductase and ACAT in rats fed a high-cholesterol diet.
This bioflavonoid is difficult to absorb on oral ingestion. In the best-case scenario, only 15% of ingested naringenin will get absorbed in the human gastrointestinal tract. A full glass of orange juice will supply about enough naringenin to achieve a [blood plasma?] concentration of about 0.5 micromoles per liter.
The naringenin-7-glucoside form seems less bioavailable than the aglycol form.
Grapefruit juice can provide much higher plasma concentrations of naringenin than orange juice. Also found in grapefruit is the related compound Kaempferol
, which has a hydroxyl group next to the ketone group.
Naringenin can be absorbed from cooked tomato paste.
Flavanone
The flavanones are a type of flavonoids. They are generally glycosylated by a disaccharide at position seven to give flavanone glycosides.-List of flavanones:* Butin* Eriodictyol* Hesperetin* Hesperidin* Homoeriodictyol* Isosakuranetin* Naringenin...
, a type of flavonoid, that is considered to have a bioactive effect on human health as antioxidant
Antioxidant
An antioxidant is a molecule capable of inhibiting the oxidation of other molecules. Oxidation is a chemical reaction that transfers electrons or hydrogen from a substance to an oxidizing agent. Oxidation reactions can produce free radicals. In turn, these radicals can start chain reactions. When...
, free radical scavenger, anti-inflammatory
Anti-inflammatory
Anti-inflammatory refers to the property of a substance or treatment that reduces inflammation. Anti-inflammatory drugs make up about half of analgesics, remedying pain by reducing inflammation as opposed to opioids, which affect the central nervous system....
, carbohydrate
Carbohydrate
A carbohydrate is an organic compound with the empirical formula ; that is, consists only of carbon, hydrogen, and oxygen, with a hydrogen:oxygen atom ratio of 2:1 . However, there are exceptions to this. One common example would be deoxyribose, a component of DNA, which has the empirical...
metabolism
Metabolism
Metabolism is the set of chemical reactions that happen in the cells of living organisms to sustain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments. Metabolism is usually divided into two categories...
promoter, and immune system
Immune system
An immune system is a system of biological structures and processes within an organism that protects against disease by identifying and killing pathogens and tumor cells. It detects a wide variety of agents, from viruses to parasitic worms, and needs to distinguish them from the organism's own...
modulator. It is the predominant flavanone
Flavanone
The flavanones are a type of flavonoids. They are generally glycosylated by a disaccharide at position seven to give flavanone glycosides.-List of flavanones:* Butin* Eriodictyol* Hesperetin* Hesperidin* Homoeriodictyol* Isosakuranetin* Naringenin...
in grapefruit
Grapefruit
The grapefruit , is a subtropical citrus tree known for its sour fruit, an 18th-century hybrid first bred in Barbados. When found, it was named the "forbidden fruit"; it has also been misidentified with the pomelo or shaddock , one of the parents of this hybrid, the other being sweet orange The...
.
Biological effects
This substance has also been shown to reduce oxidative damage to DNADNA
Deoxyribonucleic acid is a nucleic acid that contains the genetic instructions used in the development and functioning of all known living organisms . The DNA segments that carry this genetic information are called genes, but other DNA sequences have structural purposes, or are involved in...
in vitro
In vitro
In vitro refers to studies in experimental biology that are conducted using components of an organism that have been isolated from their usual biological context in order to permit a more detailed or more convenient analysis than can be done with whole organisms. Colloquially, these experiments...
. Scientists exposed cells to 80 micromoles of naringenin per liter, for 24 hours, and found that the amount of hydroxyl damage to the DNA was reduced by 24% in that very short period of time.
Naringenin found in grapefruit juice has been shown to have an inhibitory effect on the human cytochrome P450 isoform CYP1A2
CYP1A2
Cytochrome P450 1A2 , a member of the cytochrome P450 mixed-function oxidase system, is involved in the metabolism of xenobiotics in the body...
, which can change pharmacokinetics
Pharmacokinetics
Pharmacokinetics, sometimes abbreviated as PK, is a branch of pharmacology dedicated to the determination of the fate of substances administered externally to a living organism...
in a human (or orthologous
Homology (biology)
Homology forms the basis of organization for comparative biology. In 1843, Richard Owen defined homology as "the same organ in different animals under every variety of form and function". Organs as different as a bat's wing, a seal's flipper, a cat's paw and a human hand have a common underlying...
) host of several popular drugs in an adverse manner, even resulting in carcinogens of otherwise harmless substances.
Naringenin has also been shown to reduce hepatitis C
Hepatitis C
Hepatitis C is an infectious disease primarily affecting the liver, caused by the hepatitis C virus . The infection is often asymptomatic, but chronic infection can lead to scarring of the liver and ultimately to cirrhosis, which is generally apparent after many years...
virus production by infected hepatocyte
Hepatocyte
A hepatocyte is a cell of the main tissue of the liver. Hepatocytes make up 70-80% of the liver's cytoplasmic mass.These cells are involved in:* Protein synthesis* Protein storage* Transformation of carbohydrates...
s (liver cells) in cell culture
Cell culture
Cell culture is the complex process by which cells are grown under controlled conditions. In practice, the term "cell culture" has come to refer to the culturing of cells derived from singlecellular eukaryotes, especially animal cells. However, there are also cultures of plants, fungi and microbes,...
. This seem to be secondary to Naringenin ability to inhibit the secretion of very-low-density lipoprotein
Lipoprotein
A lipoprotein is a biochemical assembly that contains both proteins and lipids water-bound to the proteins. Many enzymes, transporters, structural proteins, antigens, adhesins, and toxins are lipoproteins...
by the cells. The antiviral effects of naringenin are currently under clinical investigation.
Naringenin seems to protect LDLR-deficient mice from the obesity effects of a high-fat diet.
Naringenin lowers the plasma and hepatic cholesterol
Cholesterol
Cholesterol is a complex isoprenoid. Specifically, it is a waxy steroid of fat that is produced in the liver or intestines. It is used to produce hormones and cell membranes and is transported in the blood plasma of all mammals. It is an essential structural component of mammalian cell membranes...
concentrations by suppressing HMG-CoA reductase and ACAT in rats fed a high-cholesterol diet.
Sources and bioavailability
Grapefruit, Oranges, and Tomato (skin).This bioflavonoid is difficult to absorb on oral ingestion. In the best-case scenario, only 15% of ingested naringenin will get absorbed in the human gastrointestinal tract. A full glass of orange juice will supply about enough naringenin to achieve a [blood plasma?] concentration of about 0.5 micromoles per liter.
The naringenin-7-glucoside form seems less bioavailable than the aglycol form.
Grapefruit juice can provide much higher plasma concentrations of naringenin than orange juice. Also found in grapefruit is the related compound Kaempferol
Kaempferol
Kaempferol is a natural flavonol, a type of flavonoid, that has been isolated from tea, broccoli, Delphinium, Witch-hazel, grapefruit,cabbage, kale, beans, endive, leek, tomato, strawberries, grapes, brussels sprouts, apples and other plant sources. Kaempferol is a yellow crystalline solid with a...
, which has a hydroxyl group next to the ketone group.
Naringenin can be absorbed from cooked tomato paste.