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Chemical Compound Review

Arctigenen     (3R,4S)-4-[(3,4- dimethoxyphenyl)methyl]-3...

Synonyms: Arctigenin, Tocris-1777, CHEMBL435734, SureCN381820, A1854_SIGMA, ...
 
 
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Disease relevance of Arctigenin

 

High impact information on Arctigenin

  • Six 2,3-dibenzylbutyrolactone-type lignans were biologically evaluated, and two of them, arctigenin and matairesinol, showed potent activity to suppress NO production in vitro in LPS-activated macrophages of SD rat [5].
  • Arctigenin from Fructus Arctii is a novel suppressor of heat shock response in mammalian cells [3].
  • Nordihydroguaiaretic acid (NDGA), commonly used for the inhibition of lipoxygenase isoenzymes, showed the strongest growth inhibition with an IC50 of 1.9+/-0.5 microg followed by epiashantin (IC50=9.8+/-4.5 microM) and arctigenin (IC50=16.5+/-8.5 microM) [6].
  • Both lignans were stable in rat gastric juice and arctiin was rapidly transformed to arctigenin in rat large intestinal flora, followed by conversion to the major metabolite, 2-(3",4"-dihydroxybenzyl)-3-(3',4'-dimethoxybenzyl)-butyrolactone [7].
  • Consequently, the lignans, arctiin (ARC) and arctigenin (ARC-G), were obtained from the aerial part of Saussurea medusaas active constituents [8].
 

Biological context of Arctigenin

 

Anatomical context of Arctigenin

  • The results suggested that arctigenin may regulate immune responses in activated macrophages and lymphocytes including TNF-alpha and NO production and lymphocyte proliferation [12].
  • From these results, it can be concluded that arctigenin, traxillagenin, and 4'-demethyltraxillagenin may protect hepatocytes from CCl(4) injury by maintaining the GSH level [13].
 

Associations of Arctigenin with other chemical compounds

 

Gene context of Arctigenin

References

  1. Identification of arctigenin as an antitumor agent having the ability to eliminate the tolerance of cancer cells to nutrient starvation. Awale, S., Lu, J., Kalauni, S.K., Kurashima, Y., Tezuka, Y., Kadota, S., Esumi, H. Cancer Res. (2006) [Pubmed]
  2. Arctigenin protects cultured cortical neurons from glutamate-induced neurodegeneration by binding to kainate receptor. Jang, Y.P., Kim, S.R., Choi, Y.H., Kim, J., Kim, S.G., Markelonis, G.J., Oh, T.H., Kim, Y.C. J. Neurosci. Res. (2002) [Pubmed]
  3. Arctigenin from Fructus Arctii is a novel suppressor of heat shock response in mammalian cells. Ishihara, K., Yamagishi, N., Saito, Y., Takasaki, M., Konoshima, T., Hatayama, T. Cell Stress Chaperones (2006) [Pubmed]
  4. Natural flavonoids and lignans are potent cytostatic agents against human leukemic HL-60 cells. Hirano, T., Gotoh, M., Oka, K. Life Sci. (1994) [Pubmed]
  5. Lignans from Saussurea conica and their NO production suppressing activity. Fan, C.Q., Zhu, X.Z., Zhan, Z.J., Ji, X.Q., Li, H., Yue, J.M. Planta Med. (2006) [Pubmed]
  6. Naturally occurring lignans efficiently induce apoptosis in colorectal tumor cells. Hausott, B., Greger, H., Marian, B. J. Cancer Res. Clin. Oncol. (2003) [Pubmed]
  7. Structural transformation of lignan compounds in rat gastrointestinal tract. Nose, M., Fujimoto, T., Takeda, T., Nishibe, S., Ogihara, Y. Planta Med. (1992) [Pubmed]
  8. Anti-tumor-promoting activity of lignans from the aerial part of Saussurea medusa. Takasaki, M., Konoshima, T., Komatsu, K., Tokuda, H., Nishino, H. Cancer Lett. (2000) [Pubmed]
  9. Studies on differentiation inducers. VI. Lignan derivatives from Arctium fructus. (2). Umehara, K., Nakamura, M., Miyase, T., Kuroyanagi, M., Ueno, A. Chem. Pharm. Bull. (1996) [Pubmed]
  10. Potent inhibition of lipopolysaccharide-inducible nitric oxide synthase expression by dibenzylbutyrolactone lignans through inhibition of I-kappaBalpha phosphorylation and of p65 nuclear translocation in macrophages. Cho, M.K., Park, J.W., Jang, Y.P., Kim, Y.C., Kim, S.G. Int. Immunopharmacol. (2002) [Pubmed]
  11. Arctigenin, a phenylpropanoid dibenzylbutyrolactone lignan, inhibits MAP kinases and AP-1 activation via potent MKK inhibition: the role in TNF-alpha inhibition. Cho, M.K., Jang, Y.P., Kim, Y.C., Kim, S.G. Int. Immunopharmacol. (2004) [Pubmed]
  12. Immunomodulatory effect of arctigenin, a lignan compound, on tumour necrosis factor-alpha and nitric oxide production, and lymphocyte proliferation. Cho, J.Y., Kim, A.R., Yoo, E.S., Baik, K.U., Park, M.H. J. Pharm. Pharmacol. (1999) [Pubmed]
  13. Hepatoprotective dibenzylbutyrolactone lignans of Torreya nucifera against CCl4-induced toxicity in primary cultured rat hepatocytes. Kim, S.H., Jang, Y.P., Sung, S.H., Kim, C.J., Kim, J.W., Kim, Y.C. Biol. Pharm. Bull. (2003) [Pubmed]
 
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