Class of chemical compounds
Resveratrol 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 .[1] [2] Most stilbenoids are produced by plants,[2] [3] and the only known exception is the antimicrobial stilbenoid drug tapinarof which is biosynthesized by the Gram-negative bacterium Photorhabdus luminescens .[4] [5] [6]
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] [2] [3] Under UV irradiation, stilbene and its derivatives undergo intramolecular cyclization, called stilbene photocyclization to form dihydrophenanthrenes . Oligomeric forms are known as oligostilbenoids .
Types
Aglycones
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.[7] 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 .[8]
Stilbenoids are secondary metabolites present in Cannabis sativa .[9]
Properties
Phytoalexins have been suggested by some studies to be responsible for resistance to some tree diseases, such as pine wilt .
See also
References
^ a b 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 .
^ a b c Valletta, Alessio; Iozia, Lorenzo Maria; Leonelli, Francesca (January 2021). "Impact of Environmental Factors on Stilbene Biosynthesis" . Plants . 10 (1): 90. doi :10.3390/plants10010090 . PMC 7823792 . PMID 33406721 .
^ a b Dubrovina, A. S.; Kiselev, K. V. (October 2017). "Regulation of stilbene biosynthesis in plants" . Planta . 246 (4): 597–623. doi :10.1007/s00425-017-2730-8 . ISSN 0032-0935 . PMID 28685295 . S2CID 4015467 .
^ RICHARDSON, WILLIAM H. (1988). "Identification of an anthraquinone pigment and a hydroxystilbene antibiotic from Xenorhabdus luminescens" . Applied and Environmental Microbiology . 54 (6): 1602–1605. Bibcode :1988ApEnM..54.1602R . doi :10.1128/AEM.54.6.1602-1605.1988 . PMC 202703 . PMID 3415225 – via 0099-2240/88/061602-04$02.00/0.
^ Eleftherianos, Ioannis; Boundy, Sam; Joyce, Susan A.; Aslam, Shazia; Marshall, James W.; Cox, Russell J.; Simpson, Thomas J.; Clarke, David J.; ffrench-Constant, Richard H.; Reynolds, Stuart E. (2007-02-13). "An antibiotic produced by an insect-pathogenic bacterium suppresses host defenses through phenoloxidase inhibition" . Proceedings of the National Academy of Sciences . 104 (7): 2419–2424. Bibcode :2007PNAS..104.2419E . doi :10.1073/pnas.0610525104 . ISSN 0027-8424 . PMC 1892976 . PMID 17284598 .
^ Mori, Takahiro; Awakawa, Takayoshi; Shimomura, Koichiro; Saito, Yuri; Yang, Dengfeng; Morita, Hiroyuki; Abe, Ikuro (2016-12-22). "Structural Insight into the Enzymatic Formation of Bacterial Stilbene" . Cell Chemical Biology . 23 (12): 1468–1479. doi :10.1016/j.chembiol.2016.10.010 . ISSN 2451-9456 . PMID 27866911 .
^ 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 . S2CID 30850300 .
^ 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 .
^ 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 . S2CID 3353788 .
Books
Dihydroxylated Trihydroxylated Tetrahydroxylated O-methylated
carboxylated other acylations Glycosides
of resveratrol of rhapontigenin
Oligomeric forms
Type of
stilbenoids (molecules with a C6-C2-C6 backbone)
Types