From Wikipedia, the free encyclopedia
Kobophenol A
Names
Preferred IUPAC name
(2S ,2′R ,3S ,3′R )-3′-(3,5-Dihydroxyphenyl)-4-[(2S ,3S ,4R ,5S )-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]-2,2′-bis(4-hydroxyphenyl)-2,2′,3,3′-tetrahydro[3,4′-bi-1-benzofuran]-6,6′-diol
Other names
kob A
Identifiers
ChemSpider
InChI=1S/C56H44O13/c57-33-9-1-27(2-10-33)53-47(31-17-37(61)21-38(62)18-31)49-43(23-41(65)25-45(49)67-53)52-50-44(24-42(66)26-46(50)68-55(52)29-5-13-35(59)14-6-29)51-48(32-19-39(63)22-40(64)20-32)54(28-3-11-34(58)12-4-28)69-56(51)30-7-15-36(60)16-8-30/h1-26,47-48,51-66H/t47-,48+,51-,52+,53+,54-,55-,56-/m1/s1
N Key: RAUCCLKIJHMTND-LUPMIFTGSA-N
N InChI=1/C56H44O13/c57-33-9-1-27(2-10-33)53-47(31-17-37(61)21-38(62)18-31)49-43(23-41(65)25-45(49)67-53)52-50-44(24-42(66)26-46(50)68-55(52)29-5-13-35(59)14-6-29)51-48(32-19-39(63)22-40(64)20-32)54(28-3-11-34(58)12-4-28)69-56(51)30-7-15-36(60)16-8-30/h1-26,47-48,51-66H/t47-,48+,51-,52+,53+,54-,55-,56-/m1/s1
Key: RAUCCLKIJHMTND-LUPMIFTGBD
Oc1ccc(cc1)[C@@H]4Oc2cc(O)cc(c2[C@H]4c3cc(O)cc(O)c3)[C@H]6c7c(O[C@@H]6c5ccc(O)cc5)cc(O)cc7[C@H]%10[C@H](O[C@H](c8ccc(O)cc8)[C@H]%10c9cc(O)cc(O)c9)c%11ccc(O)cc%11
Properties
C56 H44 O13
Molar mass
924.94 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Kobophenol A is a stilbenoid. It is a
tetramer of
resveratrol . It can be isolated from
Caragana chamlagu ,
[1] from
Caragana sinica
[2] and from
Carex folliculata seeds.
[3]
The molecule shows a 2,3,4,5-tetraaryltetrahydrofuran skeleton.
[3]
It has been shown to inhibit
acetylcholinesterase .
[1]
Acid-catalyzed
epimerization of kobophenol A to
carasinol B can be performed in vitro.
[4]
References
^
a
b
(+)-α-Viniferin, a Stilbene Trimer from Caragana chamlague, Inhibits Acetylcholinesterase. Sang Hyun Sung, So Young Kang, Ki Yong Lee, Mi Jung Park, Jeong Hun Kim, Jong Hee Park, Young Chul Kim, Jinwoong Kim and Young Choong Kim, Biological & Pharmaceutical Bulletin, Vol. 25, 2002 [
permanent dead link ]
^
Simultaneous determination of the contents of three stilbene oligomers in Caragana sinica collected in different seasons using an improved HPLC method. Shu Na; Zhou Hong; Hu Changqi, Biological & pharmaceutical bulletin, 2006, vol. 29, no4, pp. 608-612
^
a
b Identification and bioactivities of resveratrol oligomers and flavonoids from Carex folliculata seeds. Li L, Henry GE and Seeram NP, J Agric Food Chem., 26 August 2009, volume 57, issue 16, pages 7282-7287,
doi :
10.1021/jf901716j
^
Acid-catalyzed Epimerization of Kobophenol A to Carasinol B. Kejun Cheng, Gaolin Liang and Changqi Hu, Molecules 2008, 13(4), 938-942
Dimers Trimers Tetramers: Higher polymers (five units or more) Oligomeric forms of resveratrol
Dimers Trimers Tetramers Pentamers Hexamers Higher polymers
Glycosides or conjugates