5. Conclusion
In this study, we developed a promising antiatherogenic antioxidant, TX-2012 based on isoprenomics. The inhibitory potency of our artepillin C analogues for LDL oxidation depends not only on the lipophilicity and free radical scavenging activity, but also on the topological properties such as linearity and compactness required for LDL interaction.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
6. References
S. Huneck, C. Zdero, and F. Bohlmann, Seco-guaianolides and other constituents from artemisia species, Phytochem. 25, 883 (1986).
H. Aga, T. Shibuya, T. Sugimoto, S. Nakajima, and M. Kurimoto, Isolation and identification of antimicrobial compounds in Brazilian propolis, Biosci. Biotech. Biochem. 58, 945 (1994).
Y. Uto, A. Hirata, T. Fujita, S. Takubo, H. Nagasawa, and H. Hori, First total synthesis of artepillin C established by o,o’-diprenylation of p-halophenols in water, J. Org. Chem. 67(7), 2355–2357 (2002).
M. C. Marcucci, F. Ferreres, C. Garcia-Viguera, V. S. Bankova, S. L. De Castro, A. P. Dantas, P. H. Valente, and N. Paulino, Phenolic compounds from Brazilian propolis with pharmacological activities, J. Ethnopharmacol. 74(2), 105–112 (2001).
T. Kimoto, S. Arai, M. Aga, T. Hanaya, M. Kohguchi, Y. Nomura, and M. Kurimoto, Cell cycle and apoptosis in cancer induced by the artepillin C extracted from Brazilian propolis, Gan To Kagaku Ryoho 23(13), 1855–1859 (1996).
T. Matsuno, S. K. Jung, Y. Matsumoto, M. Saito, and J. Morikawa, Preferential cytotoxicity to tumor cells of 3,5-diprenyl-4-hydroxycinnamic acid (artepillin C) isolated from propolis, Anticancer Res. 17(5A), 3565–3568 (1997).
T. Kimoto, S. Arai, M. Kohguchi, M. Aga, Y. Nomura, M. J. Micallef, M. Kurimoto, and K. Mito, Apoptosis and suppression of tumor growth by artepillin C extracted from Brazilian propolis, Cancer Detect. Prev. 22(6), 506–515 (1998).
K. Hayashi, S. Komura, N. Isaji, N. Ohishi, and Yagi, K, Isolation of antioxidative compounds from Brazilian propolis: 3,4-dihydroxy-5-prenylcinnamic acid, a novel potent antioxidant, Chem. Pharm. Bull. 47, 1521 (1999).
D. Steinberg, Role of oxidized LDL and antioxidant in atherosclerosis, Adv. Exp. Med. Biol. 369, 39–48 (1995).
J._L. Witztum, and D. Steinberg, Role of oxidized low density lipoprotein in atherogenesis, J. Clin. Invest. 88(6), 1785–1792 (1991).
E. Tomlinson, Chromatographic hydrophobic parameters in correlation analysis of structure-activity relationships, J. Chromatogr. 113(1), 1–45 (1975).
M. S. Blois, Antioxidant determinations by the use of a stable free radical, Nature 181, 1199 (1958).
W. A. Pryor, and L. Castel, Chemical methods for the detection of lipid hydroperoxides, Methods Enzymol. 105, 293–299 (1984).
K. Yagi, Simple assay for the level of total lipid peroxides in serum or plasma, Methods Mol. Biol. 108, 101–106 (1998).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2006 Springer Science+Business Media, Inc.
About this paper
Cite this paper
Uto, Y., Ae, S., Hotta, A., Terao, J., Nagasawa, H., Hori, H. (2006). Artepillin C Isoprenomics: Design and Synthesis of Artepillin C Analogues as Antiatherogenic Antioxidants. In: Cicco, G., Bruley, D.F., Ferrari, M., Harrison, D.K. (eds) Oxygen Transport to Tissue XXVII. Advances in Experimental Medicine and Biology, vol 578. Springer, Boston, MA . https://doi.org/10.1007/0-387-29540-2_18
Download citation
DOI: https://doi.org/10.1007/0-387-29540-2_18
Publisher Name: Springer, Boston, MA
Print ISBN: 978-0-387-29543-5
Online ISBN: 978-0-387-29540-4
eBook Packages: Physics and AstronomyPhysics and Astronomy (R0)