Isorhapontigenin

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]

Isorhapontigenin
Chemical structure of isorhapontigenin.
Names
Preferred IUPAC name
5-[(E)-2-(4-Hydroxy-3-methoxyphenyl)ethen-1-yl]benzene-1,3-diol
Other names
3,4',5-trihydroxy-3'-methoxystilbene
ISO
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.230.279
UNII
  • InChI=1S/C15H14O4/c1-19-15-8-10(4-5-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2+
    Key: ANNNBEZJTNCXHY-NSCUHMNNSA-N
  • InChI=1/C15H14O4/c1-19-15-8-10(4-5-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2+
    Key: ANNNBEZJTNCXHY-NSCUHMNNBY
  • COC1=C(C=CC(=C1)C=CC2=CC(=CC(=C2)O)O)O
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

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
  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.
  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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