Isorhapontigenin

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Isorhapontigenin
Chemical structure of isorhapontigenin.
Names
IUPAC name
5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol
Other names
3,4',5-trihydroxy-3'-methoxystilbene
ISO
Identifiers
32507-66-7
ChemSpider 4477172
Jmol-3D images Image
PubChem 5318650
Properties
C15H14O4
Molar mass 258.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Isorhapontigenin is a tetrahydroxylated stilbenoid with a methoxy group. It is an isomer of rhapontigenin and an analog of resveratrol.[1] It is found in the Chinese herb Gnetum cleistostachyum,[2] in Gnetum parvifolium[3] and in the seeds of the palm Aiphanes aculeata.[4]

An isorhapontigenin tetramer, gnetuhainin R, can be isolated from the lianas of Gnetum hainanense.[5]

Isorhapontin, the isorhapontigenin glucoside, can be found in spruce species such as the Norway spruce (Picea abies), the sitka spruce (Picea sitchensis) and the white spruce (Picea glauca).[6]

References[edit]

  1. ^ Li, H.; Wang, A.; Huang, Y.; Liu, D.; Wei, C.; Williams, G.; Zhang, C.; Liu, G.; Liu, Y.; Hao, D.; Hui, R. T.; Lin, M.; Liang, C. C. (2005). "Isorhapontigenin, a new resveratrol analog, attenuates cardiac hypertrophy via blocking signaling transduction pathways". Free Radical Biology and Medicine 38 (2): 243–257. doi:10.1016/j.freeradbiomed.2004.10.020. PMID 15607907.  edit
  2. ^ Fang, Y.; Yu, Y.; Hou, Q.; Zheng, X.; Zhang, M.; Zhang, D.; Li, J.; Wu, X. -R.; Huang, C. (2012). "The Chinese Herb Isolate Isorhapontigenin Induces Apoptosis in Human Cancer Cells by Down-regulating Overexpression of Antiapoptotic Protein XIAP". Journal of Biological Chemistry 287 (42): 35234–35243. doi:10.1074/jbc.M112.389494. PMC 3471739. PMID 22896709. 
  3. ^ Piao, Z. S.; Feng, Y. B.; Wang, L.; Zhang, X. Q.; Lin, M. (2010). "Synthesis and HIV-1 inhibitory activity of natural products isolated from Gnetum parvifolium and their analogues". Yao xue xue bao = Acta pharmaceutica Sinica 45 (12): 1509–1515. PMID 21351490.  (article in Chinese)
  4. ^ Lee, D.; Cuendet, M.; Vigo, J. S.; Graham, J. G.; Cabieses, F.; Fong, H. H.; Pezzuto, J. M.; Kinghorn, A. D. (2001). "A novel cyclooxygenase-inhibitory stilbenolignan from the seeds of Aiphanes aculeata". Organic letters 3 (14): 2169–2171. doi:10.1021/ol015985j. PMID 11440571. 
  5. ^ Huang, K. S.; Zhou, S.; Lin, M.; Wang, Y. H. (2002). "An Isorhapontigenin Tetramer and a Novel Stilbene Dimer fromGnetum hainanense". Planta Medica 68 (10): 916–920. doi:10.1055/s-2002-34951. PMID 12391556. 
  6. ^ Hammerbacher, A.; Ralph, S. G.; Bohlmann, J.; Fenning, T. M.; Gershenzon, J.; Schmidt, A. (2011). "Biosynthesis of the Major Tetrahydroxystilbenes in Spruce, Astringin and Isorhapontin, Proceeds via Resveratrol and is Enhanced by Fungal Infection". Plant Physiology 157 (2): 876–890. doi:10.1104/pp.111.181420. PMC 3192583. PMID 21865488. 
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