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 C
6H
5CH=CHC
6H
3(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 CO
2
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