{{Short description|Class of chemical compounds}} [[File:Resveratrol.svg|thumb|right|Resveratrol is a biologically important stilbenoid.]] '''Stilbenoids''' are hydroxylated derivatives of stilbene. They have a C<sub>6</sub>–C<sub>2</sub>–C<sub>6</sub> structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones.<ref name="Sobolev_2006">{{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 }}</ref><ref name=":0">{{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}}</ref> Most stilbenoids are produced by plants,<ref name=":0" /><ref name=":1">{{Cite journal|last1=Dubrovina|first1=A. S.|last2=Kiselev|first2=K. V.|date=October 2017|title=Regulation of stilbene biosynthesis in plants|url=https://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}}</ref> and the only known exception is the antimicrobial stilbenoid drug tapinarof which is biosynthesized by the Gram-negative bacterium ''Photorhabdus luminescens.''<ref>{{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}}</ref><ref>{{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}}</ref><ref>{{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}}</ref>
== Chemistry == Stilbenoids are hydroxylated derivatives of stilbene and have a C<sub>6</sub>–C<sub>2</sub>–C<sub>6</sub> structure. They belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones.<ref name="Sobolev_2006"/><ref name=":0" /><ref name=":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.<ref>{{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 }} </ref> 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''.<ref>{{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}}</ref>
Stilbenoids are secondary metabolites present in Cannabis sativa.<ref>{{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}}</ref>
== 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 == {{Reflist}}
== 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}}
{{Stilbenes}}{{Stilbenoids}}{{Phenylpropanoids}}
Category:Stilbenoids Category:Wood extracts