Piceatannol is the organic compound with the formula . Classified as a

stilbenoid Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C2–C6 structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones. Most stilbenoids are prod ...

and a

phenol Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it req ...

, it is a white solid, although samples often are yellow owing to impurities.

Natural occurrences

Piceatannol and its

glucoside A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes. The name was o ...

astringin Astringin is a stilbenoid, the 3-β-D-glucoside of piceatannol. It can be found in the bark of ''Picea sitchensis'' or ''Picea abies'' (Norway spruce). It is also present in ''Vitis vinifera'' cells cultures and in wine. See also *Phenolic co ...

, are found in mycorrhizal and non-mycorrhizal roots of Norway spruces (''Picea abies''). It can also be found in the seeds of the palm ''

Aiphanes horrida ''Aiphanes horrida'' is a Arecaceae, palm native to northern South America and Trinidad and Tobago. ''Aiphanes horrida'' is a solitary, spine (botany), spiny tree. In the wild it grows 3–10 metres tall (9–30 feet) tall with a stem diameter ...

'' and in ''

Gnetum cleistostachyum ''Gnetum cleistostachyum'' is a liana species in the ''Sessiles'' subsection of the genus ''Gnetum'' described from South East Yunnan. The name is still invalid and efloras states it is advisable to postpone validating it until more complete c ...

''. The chemical structure of piceatannol was established by Cunningham et al. as being an

analog Analog or analogue may refer to: Computing and electronics * Analog signal, in which information is encoded in a continuous variable ** Analog device, an apparatus that operates on analog signals *** Analog electronics, circuits which use analog ...

resveratrol Resveratrol (3,5,4′-trihydroxy-''trans''-stilbene) is a stilbenoid, a type of natural phenol, and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi. Sources ...

In food

Piceatannol is a metabolite of resveratrol found in

red wine Red wine is a type of wine made from dark-colored grape varieties. The color of the wine can range from intense violet, typical of young wines, through to brick red for mature wines and brown for older red wines. The juice from most purple grap ...

, grapes, passion fruit, white tea, and

Japanese knotweed ''Reynoutria japonica'', synonyms ''Fallopia japonica'' and ''Polygonum cuspidatum'', is a species of herbaceous perennial plant in the knotweed and buckwheat family Polygonaceae. Common names include Japanese knotweed and Asian knotweed. It is ...

Astringin Astringin is a stilbenoid, the 3-β-D-glucoside of piceatannol. It can be found in the bark of ''Picea sitchensis'' or ''Picea abies'' (Norway spruce). It is also present in ''Vitis vinifera'' cells cultures and in wine. See also *Phenolic co ...

, a piceatannol glucoside, is also found in red wine. The formation of piceatannol from resveratrol is catalyzed by

cytochrome P450 Cytochromes P450 (CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that functions as monooxygenases. In mammals, these proteins oxidize steroids, fatty acids, and xenobiotics, and are ...

Biochemical study

A 1989 ''

in vitro ''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in biology an ...

'' study found that piceatannol blocked LMP2A, a viral protein-

tyrosine kinase A tyrosine kinase is an enzyme that can transfer a phosphate group from ATP to the tyrosine residues of specific proteins inside a cell. It functions as an "on" or "off" switch in many cellular functions. Tyrosine kinases belong to a larger cla ...

implicated in

leukemia Leukemia ( also spelled leukaemia and pronounced ) is a group of blood cancers that usually begin in the bone marrow and result in high numbers of abnormal blood cells. These blood cells are not fully developed and are called ''blasts'' or ' ...

non-Hodgkin's lymphoma Non-Hodgkin lymphoma (NHL), also known as non-Hodgkin's lymphoma, is a group of blood cancers that includes all types of lymphomas except Hodgkin lymphomas. Symptoms include lymphadenopathy, enlarged lymph nodes, fever, night sweats, weight los ...

and other diseases associated with

Epstein–Barr virus The Epstein–Barr virus (EBV), formally called ''Human gammaherpesvirus 4'', is one of the nine known human herpesvirus types in the herpes family, and is one of the most common viruses in humans. EBV is a double-stranded DNA virus. It is b ...

. In 2003, this prompted research interest in piceatannol and its effect on these diseases. Injected in rats, piceatannol shows a rapid

glucuronidation Glucuronidation is often involved in drug metabolism of substances such as drugs, pollutants, bilirubin, androgens, estrogens, mineralocorticoids, glucocorticoids, fatty acid derivatives, retinoids, and bile acids. These linkages involve glycosid ...

and a poor

bioavailability In pharmacology, bioavailability is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation. By definition, when a medication is administered intravenously, its bioavailability is 100%. H ...

, according to a 2006 study. Piceatannol affect

gene expression Gene expression is the process by which information from a gene is used in the synthesis of a functional gene product that enables it to produce end products, protein or non-coding RNA, and ultimately affect a phenotype, as the final effect. The ...

s, gene functions and

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

action, resulting in the delay or complete inhibition of

adipogenesis Adipogenesis is the formation of adipocytes (fat cells) from stem cells. It involves 2 phases, determination, and terminal differentiation. Determination is mesenchymal stem cells committing to the adipocyte precursor cells, also known as preadipocy ...

Natural occurrences

In food

Biochemical study

See also

References

Further reading