Isorhapontigenin

Last updated
Isorhapontigenin
Isorhapontigenin.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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).

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]

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Isorhapontin Chemical compound

Isorhapontin is a stilbenoid. It is the glucoside of isorhapontigenin. It can be found in mycorrhizal and non-mycorrhizal roots of Norway spruces, in the bark of Picea sitchensis or in white spruce.

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Li Jiayang Chinese agronomist, Vice Minister of Agriculture (born 1956)

Li Jiayang is a Chinese agronomist and geneticist. He is Vice Minister of Agriculture in China and President of the Chinese Academy of Agricultural Sciences (CAAS). He is also Professor and Principal investigator at the Institute of Genetics and Development at the Chinese Academy of Sciences (CAS).

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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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