Pinosylvin is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula C₆H₅CH=CHC₆H₃(OH)₂. A white solid, it is related to

trans-stilbene (''E'')-Stilbene, commonly known as ''trans''-stilbene, is an organic compound represented by the condensed structural formula CHCH=CHCH. Classified as a diarylethene, it features a central ethylene moiety with one phenyl group substituent on ...

, but with two

hydroxy group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

s on one of the phenyl substituents. It is very soluble in many organic solvents, such as

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...

Occurrence

Pinosylvin is produced in plants in response to fungal infections,

ozone Ozone (), or trioxygen, is an inorganic molecule with the chemical formula . It is a pale blue gas with a distinctively pungent smell. It is an allotrope of oxygen that is much less stable than the diatomic allotrope , breaking down in the lo ...

-induced stress, and physical damage for example. It is a fungitoxin protecting the wood from fungal infection. It is present in the heartwood of '' Pinaceae'' and also found 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 ...

''. Injected in rats, pinosylvin undergoes 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.

Biosynthesis

Pinosylvin synthase In enzymology, a pinosylvin synthase () is an enzyme that catalyzes the chemical reaction :3 malonyl-CoA + cinnamoyl-CoA \rightleftharpoons 4 CoA + pinosylvin + 4 CO2 Thus, the two substrates of this enzyme are malonyl-CoA and cinnamoyl-CoA, ...

, an

enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products. A ...

, catalyzes the biosynthesis of pinosylvin from

malonyl-CoA Malonyl-CoA is a coenzyme A derivative of malonic acid. Functions It plays a key role in chain elongation in fatty acid biosynthesis and polyketide biosynthesis. Fatty acid biosynthesis Malonyl-CoA provides 2-carbon units to fatty acids and commi ...

and

cinnamoyl-CoA Cinnamoyl-Coenzyme A is an intermediate in the phenylpropanoids metabolic pathway. Enzymes using Cinnamoyl-Coenzyme A * Cinnamoyl-CoA reductase, an enzyme that catalyzes the chemical reaction cinnamaldehyde + CoA + NADP+ → cinnamoyl-CoA + NADP ...

: :3 malonyl-S-CoA + cinnamoyl-S-CoA → 4 CoA-SH + pinosylvin + 4 CO₂ This biosynthesis is noteworthy because plant biosyntheses employing cinnamic acid as a starting point are rare compared to the more common use of ''p''-coumaric acid. Two other compounds produced from cinnamic acid are anigorufone and curcumin.

References

{{Stilbenes Stilbenoids