Pinosylvin

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Pinosylvin is a natural compound related to trans-stilbene, with two hydroxyl groups on one of its phenyl rings. It is a white solid that dissolves well in many organic solvents.

Plants make pinosylvin when they are stressed by fungal infections, ozone, or physical damage, and it helps protect wood by acting as a fungicide. It is found in the heartwood of pine family trees (Pinaceae) and has also been found in Gnetum cleistostachyum.

In rats, pinosylvin is rapidly processed by the body (glucuronidation), which leads to poor bioavailability when ingested.

Pinosylvin is produced by the enzyme pinosylvin synthase, which builds it from malonyl-CoA and cinnamoyl-CoA. This route is notable because many plant pathways start from p-coumaric acid rather than cinnamic acid. Other compounds derived from cinnamic acid include anigorufone and curcumin.