Pinosylvin
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Pinosylvin is an organic compound with the formula C6H5CH=CHC6H3(OH)2. A white solid, it is related to trans-stilbene, but with two hydroxy groups on one of the phenyl substituents. It is very soluble in many organic solvents, such as acetone.[1]
Occurrence
Pinosylvin is produced in plants in response to fungal infections, ozone-induced stress, and physical damage for example.[2] It is a fungitoxin protecting the wood from fungal infection.[3] It is present in the heartwood of Pinaceae[2] and also found in Gnetum cleistostachyum.[4]
Injected in rats, pinosylvin undergoes rapid glucuronidation and a poor bioavailability.[5]
Biosynthesis
Pinosylvin synthase, an enzyme, catalyzes the biosynthesis of pinosylvin from malonyl-CoA and cinnamoyl-CoA:
- 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.[6][7]
References
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