Kobophenol A

Last updated
Kobophenol A
Kobophenol A.png
KobophenolA 3D.PNG
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
3D model (JSmol)
ChemSpider
PubChem CID
  • 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 X mark.svgN
    Key: RAUCCLKIJHMTND-LUPMIFTGSA-N X mark.svgN
  • 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
C56H44O13
Molar mass 924.955 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

  1. 1 2 Sung, Sang Hyun; Kang, So Young; Lee, Ki Yong; Park, Mi Jung; Kim, Jeong Hun; Park, Jong Hee; Kim, Young Chul; Kim, Jinwoong; Kim, Young Choong (2002). "(+)-.ALPHA.-Viniferin, a Stilbene Trimer from Caragana chamlague, Inhibits Acetylcholinesterase". Biological and Pharmaceutical Bulletin. 25 (1): 125–127. doi:10.1248/bpb.25.125. PMID   11824541.
  2. ↑ Shu, Na; Zhou, Hong; Hu, Changqi (2006). "Simultaneous Determination of the Contents of Three Stilbene Oligomers in Caragana sinica Collected in Different Seasons Using an Improved HPLC Method". Biological and Pharmaceutical Bulletin. 29 (4): 608–612. doi:10.1248/bpb.29.608. PMID   16595888.
  3. 1 2 Li, Liya; Henry, Geneive E.; Seeram, Navindra P. (2009). "Identification and Bioactivities of Resveratrol Oligomers and Flavonoids from Carex folliculata Seeds". Journal of Agricultural and Food Chemistry. 57 (16): 7282–7287. Bibcode:2009JAFC...57.7282L. doi:10.1021/jf901716j. PMID   19627089.
  4. ↑ Cheng, Kejun; Liang, Gaolin; Hu, Changqi (2008). "Acid-catalyzed Epimerization of Kobophenol A to Carasinol B". Molecules. 13 (4): 938–942. doi: 10.3390/molecules13040938 . PMID   18463595.
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