Abstract
A new eudesmanolide, 1β,3β-dihydroxy-eudesman-11(13)-en-6α,12-olide (1) was isolated and identified from Taraxacum mongolicum, together with two known compounds, 1β,3β-dihydroxyeudesman-6α,12-olide (2) and loliolide (3). The structure of 1 was established by analysis of its physical and spectroscopic data. 1 was found to have an inhibitory activity on nitric oxide production with an IC50 of 38.9 μM in activated RAW 264.7 cells.
Similar content being viewed by others
References
Ahmad, V. U., Yasmeen, S., Ali, Z., Khan, M. A., Choudhary, M. I., Akhtar, F., Miana, G. A., and Zahid, M., Taraxacin, a new guaianolide from Taraxacum wallichii. J. Nat. Prod., 63, 1010–1011 (2000).
Bredt, D. S. and Snyder, S. H., Nitric oxide: A physiologic messenger molecule. Annu. Rev. Biochem., 63, 175–195 (1994).
Chabrier, P. E., Demerlé-Pallardy, C., and Auguet, M., Nitric oxide synthases: Targets for therapeutic strategies in neurological diseases. Cell. Mol. Life Sci., 55, 1029–1035 (1999).
Garcia, Y., Garcia-Granados, A., Martinez, A., Parra, A., and Rivas, F., Microbial transformations of 6α- and 6β-eudesmanolides by Rhizopus nigricans cultures. J. Nat. Prod., 58, 1498–1507 (1995).
Green, L. C., Wagner, D. A., Glogowski, J., Skipper, P. L., Wishnok, J. S., and Tannenbaum, S. R., Analysis of nitrate, nitrite, and [15N] nitrate in biological fluids. Anal. Biochem., 126, 131–138 (1982).
Griffith, O. W. and Stuehr, D. J., Nitric oxide synthases: Properties and catalytic mechanism. Annu. Rev. Physiol., 57, 707–736 (1995).
Gross, S. S. and Wolin, M. S., Nitric oxide: Pathophysiological mechanisms. Annu. Rev. Physiol., 57, 737–769 (1995).
Hobbs, A. J., Higgs, A., and Moncada, S., Inhibition of nitric oxide synthase as a potential therapeutic target. Annu. Rev. Pharmacol. Toxicol., 39, 191–220 (1999).
Hu, C. and Kitts, D. D., Luteolin and luteolin-7-O-glucoside from dandelion flower suppress iNOS and COX-2 in RAW264.7 cells. Mol. Cell. Biochem., 265, 107–113 (2004).
Park, B. M., Hong, S. S., Lee, C., Lee, M. S., Kang, S. J., Shin, Y. S., Jung, J. K., Hong, J. T., Kim, Y., Lee, M. K., and Hwang, B. Y., Naphthoquinones from Catalpa ovata and their inhibitory effects on the production of nitrix oxide. Arch. Pharm. Res., 33, 381–385 (2010).
Kim, W. G., Song, N. K., and Yoo, I. D., Trienomycin G, a new inhibitor of nitric oxide production in microglia cells from Streptomyces sp. 91614. J. Antibiot., 55, 204–207 (2002).
Kimura, J. and Maki, N., New loliolide derivatives from the brown alga Undaria pinnatifida. J. Nat. Prod., 65, 57–58 (2002).
Kisiel, W. and Barszcz, B., Further sesquiterpenoids and phenolics from Taraxacum officinale. Fitoterapia, 71, 269–273 (2000).
Kisiel, W. and Michalska, K., Sesquiterpenoids and phenolics from Taraxacum hondoense. Fitoterapia, 76, 520–524 (2005).
Leu, Y. L., Wang, Y. L., Huang, S. C., and Shi, L. S., Chemical constituents from roots of Taraxacum formosanum. Chem. Pharm. Bull., 53, 853–855 (2005).
Marletta, M. A., Nitric oxide synthase: Aspects concerning structure and catalysis. Cell, 78, 927–930 (1994).
Michalska, K. and Kisiel, W., Sesquiterpene lactones from Taraxacum obovatum. Planta Med., 69, 181–183 (2003).
Nathan, C. and Xie, Q. W., Nitric oxide synthases: Roles, tolls, and controls. Cell, 78, 915–918 (1994).
Salerno, L., Sorrenti, V., Di Giacomo, C., Romeo, G., and Siracusa, M. A., Progress in the development of selective nitric oxide synthase inhibitors. Curr. Pharm. Des., 8, 177–200 (2002).
Seo, S.-W., Koo, H.-N., An, H. J., Kwon, K. B., Lim, B. C., Seo, E. A., Ryu, D. G., Moon, G., Kim, H. Y., Kim, H. M., and Hong, S. H., Taraxacum officinale protects against cholecystokinin-induced acute pancreatitis in rats. World J. Gastroenterol., 11, 597–599 (2005).
Shi, S., Zhou, H., Zhang, Y., Zhao, Y., Huang, K., and Liu, S., A high-speed counter-current chromatography-HPLCDAD method for preparative isolation and purification of two polymethoxylated flavones from Taraxacum mongolicum. J. Chromatogr. Sci., 47, 349–353 (2009).
Takasaki, M., Konoshima, T., Tokuda, H., Aari, Y., Shiojima, K., and Ageta, H., Anti-carcinogenic activity of Taraxacum plant. I. Biol. Pharm. Bull., 22, 602–605 (1999).
Wei, S., Zhou, Q., and Mathews, S., A newly found cadmium accumulator-Taraxacum mongolicum. J. Hazard. Mater., 159, 544–547 (2008).
Zhu, M., Wong, P. Y., and Li, R. C., Effects of Taraxacum mongolicum on the bioavailability and disposition of ciprofloxacin in rats. J. Pharm. Sci., 88, 632–634 (1999).
Zidorn, C., Ellmerer-Müller, E. P., and Stuppner, H., Eudesmanolides and inositol derivatives from Taraxacum linearis-quameum. Phytochemistry, 51, 991–994 (1999).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kim, YH., Choo, SJ., Ryoo, IJ. et al. Eudesmanolides from Taraxacum mongolicum and their inhibitory effects on the production of nitric oxide. Arch. Pharm. Res. 34, 37–41 (2011). https://doi.org/10.1007/s12272-011-0104-5
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-011-0104-5