Document Detail

Natural occurrence of cancer-preventive geranylgeranoic acid in medicinal herbs.
MedLine Citation:
PMID:  15060084     Owner:  NLM     Status:  MEDLINE    
Geranylgeranoic acid (GGA; all-trans 3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenoic acid) has been shown to induce apoptosis in a human hepatoma-derived cell line, HuH-7. We aimed not only to confirm the apoptogenic properties of GGA and its derivatives, but also to search for natural GGA in medicinal herbs. GGA induced apoptosis in human hepatoma-derived cell lines, HuH-7, PLC/PRF-5, and mouse transformed hepatocyte-derived cell line, MLE-10, in a dose- and time-dependent manner, but failed to induce cell death in human hepatoblastoma-derived HepG-2 and mouse primary hepatocytes in the same condition. Besides GGA, 4,5-didehydro GGA, 14,15-dihydro GGA, and 2,3-dihydro GGA were also active to induce cell death in HuH-7 cells, while 4,5-didehydro-10,11, 14,15-tetrahydro GGA, 4,5,8,9-tetrahydro GGA, farnesoic acid, and geranylgeraniol were inert. By using liquid chromatography/mass spectrometry, we found natural GGA as a negative ion of m/z 303.4 in a Chinese herb, Schisandra chinensis, and Schisandra GGA was identified by derivatization with both mild methylation and catalytic hydrogenation. Some other GGAs hydrogenated in the different degrees, including phytanic acid (perhydro GGA), were also found in S. chinensis. GGA and phytanic acid were detected in 24 out of 25 herbs tested. The present study is the first report of natural GGA in medicinal herbs.
Yoshihiro Shidoji; Hiroko Ogawa
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Publication Detail:
Type:  Journal Article     Date:  2004-04-01
Journal Detail:
Title:  Journal of lipid research     Volume:  45     ISSN:  0022-2275     ISO Abbreviation:  J. Lipid Res.     Publication Date:  2004 Jun 
Date Detail:
Created Date:  2004-05-13     Completed Date:  2005-03-02     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0376606     Medline TA:  J Lipid Res     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1092-103     Citation Subset:  IM    
Laboratory of Cellular Biochemistry, Graduate School of Human Health Sciences, Siebold University of Nagasaki, Nagayo, Nagasaki 851-2195, Japan.
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MeSH Terms
Cell Death / drug effects
Cells, Cultured
Chromatography, Liquid
Diterpenes / analysis,  chemistry*,  pharmacology*
Gas Chromatography-Mass Spectrometry
Liver Neoplasms / drug therapy,  pathology,  prevention & control*
Molecular Structure
Plant Extracts / chemistry
Plants, Medicinal / chemistry*
Reg. No./Substance:
0/Diterpenes; 0/Plant Extracts; 83807-40-3/geranylgeranic acid

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