Isorhapontigenin Explained

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]

Notes and References

1. Li . H. . Wang . A. . Huang . Y. . Liu . D. . Wei . C. . Williams . G. . Zhang . C. . Liu . G. . Liu . Y. . 10.1016/j.freeradbiomed.2004.10.020 . Hao . D. . Hui . R. T. . Lin . M. . Liang . C. C. . Isorhapontigenin, a new resveratrol analog, attenuates cardiac hypertrophy via blocking signaling transduction pathways . Free Radical Biology and Medicine . 38 . 2 . 243–257 . 2005 . 15607907.
2. Fang . Y. . Yu . Y. . Hou . Q. . Zheng . X. . Zhang . M. . Zhang . D. . Li . J. . Wu . X. -R. . Huang . C. . 10.1074/jbc.M112.389494 . 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 . 2012 . 22896709. 3471739 . free .
3. Piao . Z. S. . Feng . Y. B. . Wang . L. . Zhang . X. Q. . Lin . M. . 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 . 2010 . 21351490. (article in Chinese)
4. 10.1021/ol015985j . Lee . D. . Cuendet . M. . Vigo . J. S. . Graham . J. G. . Cabieses . F. . Fong . H. H. . Pezzuto . J. M. . Kinghorn . A. D. . A novel cyclooxygenase-inhibitory stilbenolignan from the seeds of Aiphanes aculeata . Organic Letters . 3 . 14 . 2169–2171 . 2001 . 11440571.
5. Huang . K. S. . Zhou . S. . Lin . M. . Wang . Y. H. . An Isorhapontigenin Tetramer and a Novel Stilbene Dimer fromGnetum hainanense . 10.1055/s-2002-34951 . Planta Medica . 68 . 10 . 916–920 . 2002 . 12391556 .
6. Hammerbacher . A. . Ralph . S. G. . Bohlmann . J. . Fenning . T. M. . Gershenzon . J. . Schmidt . A. . 10.1104/pp.111.181420 . 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 . 2011 . 21865488. 3192583 .