Stilbenoid

Stilbenoids are hydroxylated derivatives of stilbene. They have a C₆–C₂–C₆ structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones.[1] Stilbenoids can be produced by plants and bacteria.

Resveratrol is a biologically important stilbenoid.

Chemistry

Stilbenoids are hydroxylated derivatives of stilbene and have a C₆–C₂–C₆ structure. They belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones.[1] Under UV irradiation, stilbene and its derivatives undergo intramolecular cyclization, called Stilbene photocyclization to form dihydrophenanthrenes. Oligomeric forms are known as oligostilbenoids.

Types

Aglycones

• Piceatannol in the roots of Norway spruces
• Pinosylvin is a fungal toxin protecting wood from fungal infection, found in trees of the pine family
• Pterostilbene in almonds, pine and vaccinium berries
• Resveratrol in grapes

Glycosides

• Astringin in the bark of Norway spruce
• Piceid is a resveratrol derivative in grape juices

Production

Stilbenoids are produced in various plants, for example they are secondary products of heartwood formation in trees that can act as phytoalexins. Another example is resveratrol, an antifungal which is found in grapes and which has been suggested to have health benefits.[2] Ampelopsin A and Ampelopsin B are resveratrol dimers produced in porcelain berry.

A bacterial stilbenoid, (E)-3,5-dihydroxy-4-isopropyl-trans-stilbene, is produced by Photorhabdus which is a bacterial symbiont of insect nematodes called Heterorhabditis.[3]

Stilbenoids are secondary metabolites present in Cannabis sativa.[4]

Properties

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

See also

• Combretastatins, many are stilbenoids
• Dihydrostilbenoids, no double bond on the bridge
• List of antioxidants in food
• List of phytochemicals in food
• Phytochemistry
• Secondary metabolites
• Stilbestrol

References

1. V. S. Sobolev; B. W. Horn; T. L. Potter; S. T. Deyrup; J. B. Gloer (2006). "Production of Stilbenoids and Phenolic Acids by the Peanut Plant at Early Stages of Growth". J. Agric. Food Chem. 54 (10): 3505–3511. doi:10.1021/jf0602673. PMID 19127717.
2. Jang MS, Cai EN, Udeani GO (1997). "Cancer chemopreventive activity of resveratrol, a natural product derived from grapes". Science. 275 (5297): 218–220. doi:10.1126/science.275.5297.218. PMID 8985016.
3. Joyce SA, Brachmann AO, Glazer I, Lango L, Schwär G, Clarke DJ, Bode HB (2008). "Bacterial biosynthesis of a multipotent stilbene". Angew Chem Int Ed Engl. 47 (10): 1942–1945. CiteSeerX 10.1.1.603.247. doi:10.1002/anie.200705148. PMID 18236486.
4. Flores-Sanchez, Isvett Josefina; Verpoorte, Robert (2008-10-01). "Secondary metabolism in cannabis". Phytochemistry Reviews. 7 (3): 615–639. doi:10.1007/s11101-008-9094-4.

Books

• Hillis, W.E. (1987). Heartwood and Tree Exudates. Berlin, Heidelberg: Springer Berlin Heidelberg. ISBN 978-3-642-72534-0.
• YAMADA, Toshihiro; ITO, Shin-ichiro (1993). "Chemical Defense Responses of Wilt-Resistant Pine Species, Pinus strobus and P. taeda, against Bursaphelenchus xylophilus Infection". Japanese Journal of Phytopathology. 59 (6): 666–672. doi:10.3186/jjphytopath.59.666.