From Wikipedia, the free encyclopedia
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 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
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