Chemistry: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 antihelminthic and antimicrobial stilbenoid, 2-isopropyl-5-[(E)-2-phenylvinyl]benzene-1,3-diol, 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
- 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.[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
- 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
- ↑ 1.0 1.1 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.
- ↑ 2.0 2.1 2.2 Valletta, Alessio; Iozia, Lorenzo Maria; Leonelli, Francesca (January 2021). "Impact of Environmental Factors on Stilbene Biosynthesis" (in en). Plants 10 (1): 90. doi:10.3390/plants10010090. PMID 33406721.
- ↑ 3.0 3.1 Dubrovina, A. S.; Kiselev, K. V. (October 2017). "Regulation of stilbene biosynthesis in plants" (in en). Planta 246 (4): 597–623. doi:10.1007/s00425-017-2730-8. ISSN 0032-0935. PMID 28685295. http://link.springer.com/10.1007/s00425-017-2730-8.
- ↑ RICHARDSON, WILLIAM H. (1988). "Identification of an anthraquinone pigment and a hydroxystilbene antibiotic from Xenorhabdus luminescens". Applied and Environmental Microbiology 54 (6): 1602–1605. doi:10.1128/AEM.54.6.1602-1605.1988. PMID 3415225. Bibcode: 1988ApEnM..54.1602R.
- ↑ Eleftherianos, Ioannis; Boundy, Sam; Joyce, Susan A.; Aslam, Shazia; Marshall, James W.; Cox, Russell J.; Simpson, Thomas J.; Clarke, David J. et al. (2007-02-13). "An antibiotic produced by an insect-pathogenic bacterium suppresses host defenses through phenoloxidase inhibition" (in en). Proceedings of the National Academy of Sciences 104 (7): 2419–2424. doi:10.1073/pnas.0610525104. ISSN 0027-8424. PMID 17284598. Bibcode: 2007PNAS..104.2419E.
- ↑ 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" (in English). Cell Chemical Biology 23 (12): 1468–1479. doi:10.1016/j.chembiol.2016.10.010. ISSN 2451-9456. PMID 27866911.
- ↑ "Cancer chemopreventive activity of resveratrol, a natural product derived from grapes". Science 275 (5297): 218–220. 1997. doi:10.1126/science.275.5297.218. PMID 8985016.
- ↑ "Bacterial biosynthesis of a multipotent stilbene". Angew Chem Int Ed Engl 47 (10): 1942–1945. 2008. 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.
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.
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