Stilbenoids are secondary products of heartwood formation in trees that can act as phytoalexins. In chemical terms, they are hydroxylated derivatives of stilbene

Stilbene

-Stilbene, is a diarylethene, i.e., a hydrocarbon consisting of a trans ethene double bond substituted with a phenyl group on both carbon atoms of the double bond. The name stilbene is derived from the Greek word stilbos, which means shining....

. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis

Biosynthesis

Biosynthesis is an enzyme-catalyzed process in cells of living organisms by which substrates are converted to more complex products. The biosynthesis process often consists of several enzymatic steps in which the product of one step is used as substrate in the following step...

 pathway with chalcones. An alternative bacterial stilbenoid ketosynthase-directed pathway exists in bacterial symbionts of nematodes.

An example of a stilbenoid is resveratrol

Resveratrol

Resveratrol is a stilbenoid, a type of natural phenol, and a phytoalexin produced naturally by several plants when under attack by pathogens such as bacteria or fungi....

, which is found in grape

Grape

A grape is a non-climacteric fruit, specifically a berry, that grows on the perennial and deciduous woody vines of the genus Vitis. Grapes can be eaten raw or they can be used for making jam, juice, jelly, vinegar, wine, grape seed extracts, raisins, molasses and grape seed oil. Grapes are also...

s and which has been suggested to have many health benefits.

Phytoalexin properties

They have been suggested by some studies to be responsible for resistance to some tree diseases, such as pine wilt.

Known stilbenoids

Aglycones

• Piceatannol
  Piceatannol
  Piceatannol is a stilbenoid, a type of phenolic compound. It is a metabolite of resveratrol found in red wine.Astringin is a piceatannol glucoside.-Health effects:...
  
  
• Pinosylvin
  Pinosylvin
  Pinosylvin is a pre-infectious stilbenoid toxin , contrary to phytoalexins which are synthesized during infection. It is present in the heartwood of Pinaceae. It is a fungitoxin protecting the wood from fungal infection....
  
  
• Pterostilbene
  Pterostilbene
  Pterostilbene is a stilbenoid chemically related to resveratrol and is found in blueberries and grapes. It belongs to the group of phytoalexins, agents produced by plants to fight infections. Based on animal studies it is thought to exhibit anti-cancer, anti-hypercholesterolemia,...
  
  
• Resveratrol
  Resveratrol
  Resveratrol is a stilbenoid, a type of natural phenol, and a phytoalexin produced naturally by several plants when under attack by pathogens such as bacteria or fungi....
  
  

Oligomeric forms

• Alpha-viniferin
  Alpha-viniferin
  α-Viniferin is a stilbene trimer. It can be isolated from Caragana chamlagu and from Caragana sinicaIt has been shown to inhibit acetylcholinesterase....
  
  
• Ampelopsin A
• Ampelopsin E
• Diptoindonesin C can be isolated from the bark of Shorea pinanga
• Diptoindonesin F can be isolated from the bark of Shorea gibbosa
  Shorea gibbosa
  Shorea gibbosa is a large emergent rainforest tree species in the Dipterocarpaceae family. It is native to Sumatra, Borneo, Peninsular Malaysia and Singapore . The tallest measured specimen is 81,1 metres tall, in the Tawau Hills National Park, in Sabah on the island of Borneo.-Source:* Ashton, P....
  
  
• Epsilon-viniferin
  Epsilon-viniferin
  ε-Viniferin is a naturally occurring polyphenol, belonging to the stilbenoids family. It is found in grapevines, in wines, and in the Oriental medicinal plant Vitis coignetiae.It is a resveratrol dimer.-External links:*...
  
  
• Flexuosol A
• Gnetin H
• Hemsleyanol D
• Hopeaphenol
  Hopeaphenol
  Hopeaphenol is a stilbenoid. It is a resveratrol tetramer isolated from wines.It shows an opposite effect to vitisin A on apoptosis of myocytes isolated from adult rat heart....
  
  
• trans-diptoindonesin B
  Trans-diptoindonesin B
  trans-Diptoindonesin B is an oligomeric stilbenoid.It is a resveratrol trimer. It can be isolated from Dryobalanops oblongifolia....
  
  
• Vaticanol B

Glycosides

• Astringin
  Astringin
  Astringin is a stilbenoid. It is the piceatannol glucoside. It can be found in wine....
  
  
• Piceid
  Piceid
  Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices. It can also be isolated from Polygonum cuspidatum....
  
  

Oligomeric forms glycosides

• Diptoindonesin A
  Diptoindonesin A
  Diptoindonesin A is a C-glucoside of ε-viniferin isolated from Shorea seminis ....