Stilbenoid

File:Resveratrol.svg is a biologically important 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.{{cite journal|author1=V. S. Sobolev |author2=B. W. Horn |author3=T. L. Potter |author4=S. T. Deyrup |author5=J. B. Gloer | title = Production of Stilbenoids and Phenolic Acids by the Peanut Plant at Early Stages of Growth| journal = J. Agric. Food Chem.| year = 2006| volume = 54 | issue = 10| pages = 3505–3511| doi = 10.1021/jf0602673| pmid = 19127717 }}{{Cite journal|last1=Valletta|first1=Alessio|last2=Iozia|first2=Lorenzo Maria|last3=Leonelli|first3=Francesca|date=January 2021|title=Impact of Environmental Factors on Stilbene Biosynthesis|journal=Plants|language=en|volume=10|issue=1|pages=90|doi=10.3390/plants10010090|pmid=33406721|pmc=7823792|doi-access=free}} Most stilbenoids are produced by plants,{{Cite journal|last1=Dubrovina|first1=A. S.|last2=Kiselev|first2=K. V.|date=October 2017|title=Regulation of stilbene biosynthesis in plants|url=http://link.springer.com/10.1007/s00425-017-2730-8|journal=Planta|language=en|volume=246|issue=4|pages=597–623|doi=10.1007/s00425-017-2730-8|pmid=28685295|s2cid=4015467|issn=0032-0935|url-access=subscription}} and the only known exception is the antimicrobial stilbenoid drug tapinarof which is biosynthesized by the Gram-negative bacterium Photorhabdus luminescens.{{Cite journal|last=RICHARDSON|first=WILLIAM H.|date=1988|title=Identification of an anthraquinone pigment and a hydroxystilbene antibiotic from Xenorhabdus luminescens|url= |journal=Applied and Environmental Microbiology|volume=54|issue=6|pages=1602–1605|doi=10.1128/AEM.54.6.1602-1605.1988|pmid=3415225|pmc=202703| bibcode=1988ApEnM..54.1602R |via=0099-2240/88/061602-04$02.00/0}}{{Cite journal|last1=Eleftherianos|first1=Ioannis|last2=Boundy|first2=Sam|last3=Joyce|first3=Susan A.|last4=Aslam|first4=Shazia|last5=Marshall|first5=James W.|last6=Cox|first6=Russell J.|last7=Simpson|first7=Thomas J.|last8=Clarke|first8=David J.|last9=ffrench-Constant|first9=Richard H.|last10=Reynolds|first10=Stuart E.|date=2007-02-13|title=An antibiotic produced by an insect-pathogenic bacterium suppresses host defenses through phenoloxidase inhibition|journal=Proceedings of the National Academy of Sciences|language=en|volume=104|issue=7|pages=2419–2424|doi=10.1073/pnas.0610525104|issn=0027-8424|pmc=1892976|pmid=17284598|bibcode=2007PNAS..104.2419E|doi-access=free}}{{Cite journal|last1=Mori|first1=Takahiro|last2=Awakawa|first2=Takayoshi|last3=Shimomura|first3=Koichiro|last4=Saito|first4=Yuri|last5=Yang|first5=Dengfeng|last6=Morita|first6=Hiroyuki|last7=Abe|first7=Ikuro|date=2016-12-22|title=Structural Insight into the Enzymatic Formation of Bacterial Stilbene|journal=Cell Chemical Biology|language=English|volume=23|issue=12|pages=1468–1479|doi=10.1016/j.chembiol.2016.10.010|issn=2451-9456|pmid=27866911|doi-access=free}}

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. 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.{{cite journal

|vauthors=Jang MS, Cai EN, Udeani GO | title = Cancer chemopreventive activity of resveratrol, a natural product derived from grapes

| journal = Science

| year = 1997

| volume = 275

| issue = 5297

| pages = 218–220

| url =

| doi = 10.1126/science.275.5297.218

| pmid = 8985016 | s2cid = 30850300

}}

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.{{cite journal|vauthors=Joyce SA, Brachmann AO, Glazer I, Lango L, Schwär G, Clarke DJ, Bode HB | title = Bacterial biosynthesis of a multipotent stilbene| journal = Angew Chem Int Ed Engl| year = 2008| volume = 47 | issue = 10| pages = 1942–1945| doi = 10.1002/anie.200705148|pmid=18236486| citeseerx = 10.1.1.603.247}}

Stilbenoids are secondary metabolites present in Cannabis sativa.{{Cite journal|last1=Flores-Sanchez|first1=Isvett Josefina|last2=Verpoorte|first2=Robert|date=2008-10-01|title=Secondary metabolism in cannabis|journal=Phytochemistry Reviews|volume=7|issue=3|pages=615–639|doi=10.1007/s11101-008-9094-4|s2cid=3353788}}

Properties

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

References

Books

{{cite book|last1=Hillis|first1=W.E.|title=Heartwood and Tree Exudates|date=1987|publisher=Springer Berlin Heidelberg|location=Berlin, Heidelberg|isbn=978-3-642-72534-0}}
{{cite journal|last1=YAMADA|first1=Toshihiro|last2=ITO|first2=Shin-ichiro|title=Chemical Defense Responses of Wilt-Resistant Pine Species, Pinus strobus and P. taeda, against Bursaphelenchus xylophilus Infection.|journal=Japanese Journal of Phytopathology|date=1993|volume=59|issue=6|pages=666–672|doi=10.3186/jjphytopath.59.666|doi-access=free}}

Category:Wood extracts