Planta Med 2004; 70(3): 197-200
DOI: 10.1055/s-2004-815534
Original Paper
Pharmacology
© Georg Thieme Verlag Stuttgart · New York

New Polyacetylenes, DGAT Inhibitors from the Roots of Panax ginseng

Seung Woong Lee1 , Koanhoi Kim1 , Mun-Chual Rho1 , Mi Yeon Chung1 , Young Ho Kim2 , Sangku Lee1 , Hyun Sun Lee1 , Young Kook Kim1
  • 1Laboratory of Lipid Metabolism, Korea Research Institute of Bioscience and Biotechnology, Taejon, Korea
  • 2College of Pharmacy, Chungnam National University, Taejon, Korea
This research was supported by grants from Plant Diversity Research Center of 21st Century Frontier Research Program and KRIBB Research Initiative Program funded by the Ministry of Science and Technology of the Korean government
Further Information

Publication History

Received: August 15, 2003

Accepted: November 22, 2003

Publication Date:
23 March 2004 (online)

Abstract

The petroleum ether extract of Panax ginseng showed a significant inhibition of the diacylglycerol acyltransferase (DGAT) enzyme from rat liver microsomes. Bioactivity-guided fractionation led to the isolation of two new polyacetylenic compounds, (9R,10S)-epoxyheptadecan-4,6-diyn-3-one (1) and 1-methoxy-(9R,10S)-epoxyheptadecan-4,6-diyn-3-one (2). Their chemical structures were elucidated on the basis of spectroscopic evidence and asymmetric synthesis. IC50 values of 9 μg/mL (1) and 32 μg/mL (2) were obtained.

References

  • 1 Lehner R, Kuksis A. Biosynthesis of triacylglycerols.  Prog Lipid Res. 1996;  35 169-201
  • 2 Cases S, Smith S, Zheng Y, Myers H, Lear S R, Sande E. et al . Identification of gene encoding an acyl CoA:diacylglycerol acyltransferase, a key enzyme in triacyglycerol synthesis.  Proc Natl Acad Sci USA. 1998;  95 13 018-23
  • 3 Smith S J, Cases S, Jensen D R, Chen H C, Sande E, Tow B. et al . Obesity resistance and multiple mechanisms of triglyceride synthesis in mice lacking DGAT.  Nat Genet. 2000;  25 87-90
  • 4 Jung B S, Shin M K. Encyclopedia of illustrated Korean natural drugs, Araliaceae. In: Kwon SB, editor Seoul; Young Lim Sa. 1998: pp. 439-43
  • 5 Hirakura K, Morita M, Nakajima K, Ikeya Y, Mitsuhashi H. Polyacetylenes from the roots of Panax ginseng .  Phytochemistry. 1991;  30 3327-33
  • 6 Poplawski J, Wrobel J T, Glinka T. Panaxydol, a new polyacetylenic epoxide from Panax ginseng roots.  Phytochemistry. 1980;  19 1539-41
  • 7 Saita T, Matsunaga H, Yamamoto H, Nagumo F, Fujito H, Mori M. et al . A highly sensitive enzyme-linked immunosorbent assay (ELISA) for antitumor polyacetylenic alcohol, panaxytriol.  Biol Pharm Bull. 1994;  17 798-802
  • 8 Fujimoto Y, Satoh M. Acetylenes from the callus of Panax ginseng .  Phytochemistry. 1987;  26 2850-2
  • 9 Matsunaga H, Katano M, Yamamoto H, Fujito H, Mori M, Takata K. Cytotoxic activity of polyacetylene compounds in Panax ginseng C. A. Meyer.  Chem Pharm Bull. 1990;  38 3480-2
  • 10 Wang C N, Shiao Y J, Kuo Y H, Chen C C, Lin Y L. Inducible nitric oxide synthase inhibitors from Saposhnikovia divaricata and Panax quinquefolium .  Planta Med. 2000;  66 644-7
  • 11 Kwon B M, Nam J Y, Lee S H, Jeong T S. Isolation of cholesteryl ester transfer protein inhibitors from Panax ginseng roots.  Chem Pharm Bull. 1996;  44 444-5
  • 12 Coleman R A. Diacylglycerol acyltransferase and monoacylglycerol acyltransferase from liver and intestine.  Methods Enzymol. 1992;  209 98-103
  • 13 Ko J S, Rho M C, Chung M Y, Song H Y, Kang J S, Kim K H. et al . Quinolone alkaloids, diacylglycerol acyltransferase inhibitors from the fruits of Evodia rutaecarpa .  Planta Med. 2002;  68 1131-3
  • 14 Bohlmann F, Burkhardt T, Zdero C. Naturally Occurring Acetylenes. London; Academic Press 1973: p. 4

Hyun Sun Lee, Ph. D.

Laboratory of Lipid Metabolism

Korea Research Institute of Bioscience and Biotechnology

P.O. Box 115

Yusong

Taejon 305 - 333

Korea

Phone: +82-42-860-4314

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Email: leehs@kribb.re.kr