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Screening of Biologically Active Compound from Edible Plant Sources-IX. Isolation and Identification of Sesquiterpene Lactons Isolated from the Root of Ixeris dentata forma albiflora; Inhibition Effects on ACAT, DGAT and FPTase Activity  

Bang, Myun-Ho (The Graduate School of Biotechnology & Plant Metabolism Research Center)
Jang, Tae-O (The Graduate School of Biotechnology & Plant Metabolism Research Center)
Song, Myoung-Chong (The Graduate School of Biotechnology & Plant Metabolism Research Center)
Kim, Dong-Hyun (The Graduate School of Biotechnology & Plant Metabolism Research Center)
Kwon, Byoung-Mog (Korea Research Institute of Bioscience & Biotechnology)
Kim, Young-Kuk (Korea Research Institute of Bioscience & Biotechnology)
Lee, Hyun-Sun (Korea Research Institute of Bioscience & Biotechnology)
Chung, In-Sik (The Graduate School of Biotechnology & Plant Metabolism Research Center)
Kim, Dae-Keun (Department of Pharmacy, Woosuk University)
Kim, Sung-Hoon (Graduate School of East-West Medical Science, Kyung Hee University)
Park, Mi-Hyun (Erom Life Co. Ltd.)
Baek, Nam-In (The Graduate School of Biotechnology & Plant Metabolism Research Center)
Publication Information
Applied Biological Chemistry / v.47, no.2, 2004 , pp. 251-257 More about this Journal
Abstract
The root of lxeris dentata forma albiflora was extracted with 80% aqueous MeOH and solvent fractionated with EtOAc, n-BuOH and water, successively. From the EtOAc and n-BuOH fractions, four sesquiterpene compounds were isolated through the repeated silica gel and ODS column chromatographies. The chemical structures were determined as zaluzanin C (1), $9{\alpha}-hydroxyguaian-4(l5),10(14),11(13)-triene-6,12-olide$ (2), $3{\beta}-O-{\beta}-D-glucopyranosyl-8{\alpha}-hydroxyguaian-4(15),10(14 )-diene-6,12-olide$ (3), and $3{\beta}-O-{\beta}- D-glucopyranosyl-8{\beta}hydroxyguaian-10(14)-ene-6,12-olide$ (4) through the interpretation of several spectral data including 2D-NMR. Some showed the inhibitory effects on DGAT (Diacylglycerol acyltransferase), ($IC_{50}$ values of 1, 2: 0.13, 0.10 mM), the catalyzing enzymes of the intracellular esterification of diacylglycerol and FPTase (Famesyl-protein transferase), ($IC_{50}$ values of 1, 2: 0.15, 0.18 mM), the farnesylation enzyme for Ras protein charge of cancer promotion.
Keywords
Ixeris dentata forma albiflora; guaianolide; ACAT; DGAT; FPTase;
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1 Soka, T. (1985) In Dictionary of Chinese Drugs (1st ed.) Shanghai Science Technology Shogakukan Press, Tokyo
2 Arai, Y., Kusumoto, Y., Nagao, M., Shiojima, K .and Ageta, H. (1985) Compositae constituents: Aliphatics and triterpenoide isolated from the whole plants of Ixeris debilis and I. dentata. Yakugaku Zasshi 103, 356
3 Fraga, B. M. (1991) In Sesquiterpenoids, Methods in Plant Biochemistry, Vol. 7. Academic Press, London
4 Otrnar, S., Holger, B., Bernhard, V., Edward, S. and Manfred, S. (1995) Sesquiterpene lactone chemistry of Zaluzania grayana from on-line LC-NMR measurements. Phytochemistry 39, 609-612   DOI   ScienceOn
5 Smith, S. J., Cases, S., Jensen, D. R., Chen, H. C., Sande, E., Tow, B., Sanan, R J., Eckel, R H. and Farese, R .V. (2000) Obesity resistance and multiple mechanisms of triglyceride synthesis in mice lacking Dgat. Nat. Genet. 25, 87-90
6 Kohl, N. E., Wilson, F, R., Misser, S. D., Gometz, R P., Gibbs, J. B. and Oliff, A. (1994) Protein famesyl transferase inhibitors block the growth of ras-dependent tumors in nudemice. Proc. Nall. Acad. Sci. USA 91, 9141-9145   DOI   ScienceOn
7 Tomoda, H., Ito, M., Tabata, N., Masuma, R., Yamaguchi, Y. and Omura, S. (1995) Amidepsines, inhibitors of diacylglycerol acy1transferase produced by Humicola sp. FO-2942. J. Antibiot. 48, 937-947   DOI
8 Janice, E. B. and James, C. M. (1995) Famesyl transferase inhibitors: the successes and surprises of a new class of potential cancer chemotherapeutics. Chem. Biol. 2, 789-791
9 Ericson, S. K., Shrewbery, M. A., Brooks, C. and Meyer, D. J. (1980) Rat liver acyl-coenzyme A: cholesterol acyltransferase: its regulation in vivo and some of its properties in vitro. J. Lipid Res. 21, 930-941
10 Seto, M., Miyasa, T. and Fukushima, S. (1986) Sesquiterpene lactones from lxeris dentata Nakai. Chem. Pharm. Bull. 34, 4170-4176   DOI
11 Chang, T. Y and Doolittle, G. M. (1983) In the enzyme Acy1Coenzyme A: cholesterol O-acyltransferase. Vol. XUI, Academic Press, pp. 523-539
12 Catherine, C. Y., Hun, H. Y,. Cadigan, K M. and Chang, T. Y. (1993) Molecular cloning and functional expression of human acy1-CoA: cholesterol acyltransferase cDNA in mutant chinese hamster ovary cells. J. Bioi. Chem. 268, 20747-20755
13 Rosalind, A. and Coleman, A. (1992) Diacylglycerol acy1transferase and monoacylglycerol acyltransferase from liver and intetine. Methods Enzymol. 209, 98-103   DOI
14 Sliskovic, D. R and White, A. D. (1991) Therapeutic potential of ACAT inhibitors as lipid lowering and antiatherosclerotic agents. Trends Pharmacol. Sci. 12, 194-199   DOI   ScienceOn
15 Reiss, Y., Seabra, M. C., Goldstein, J. L. and Brown, M. S. (1990) Purification of ras famesyl: protein transferase. Methods: A Companion to Methods in Enzymology. 3, 242-245
16 Nishimura, K., Miyase, T., Deno, A., Noro, T., Kuroyanagi, M. and Fukushima, S. (1986) Sesquiterpene lactones from Lactuca laciniata. Phytochemistry 35, 61583-1584
17 Warashina, T., Ishino, M., Miyase, T. and Deno, A. (1990) Sesquiterpene glycosides from Ixeris debilis and Ixeris repens. Phytochemistry 29, 3217-3224   DOI   ScienceOn
18 Lowy, D. R and Willumsen, B. M. (1993) Function and regulation of RAS. Ann. Rev. Biochem. 62, 851-891   DOI   ScienceOn
19 Kim, M. K and Lee, M. S. (1988) Volatile flavor components of Ixeris dentata and Amar anthus mangostanus. J. Kor. Agric. Chem. Soc. 31, 394-399
20 Geissman, T. A. (1973) In Recent Advances in Phytochemistry. Vol. 6. Runeckless, V. C. and Mabry. T. J. (eds.), Academic Press, New York
21 Pompliano, D. L., Rands, E., Schaber, M. D., Mosser, S. D., Anthony, N. J. and Gibbs, J. B. (1992) Steady-state kinetic mechanism of ras famesyl-protein transferase. Biochemistry 31, 3800-3807   DOI   ScienceOn