Skip to main content
SpringerLink
Log in

Polyacetylenes from the roots of cultivated-wild ginseng and their cytotoxicity in vitro

  • Articles
  • Drug Discovery
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

Column chromatographic separation of the roots of cultivated-wild ginseng (Jangnoisam) led to the isolation of seven polyacetylenes (1–7). Their structures were determined by spectroscopic methods to be panaxynol (1), ginsenoyne-A (2), panaxydol (3), 10-methoxy heptadeca-1-ene-4, 6-dyne-3, 9-diol (4) (3R, 9R, 10R)-panaxytriol (5), panaxyne (6), and ginsenoyne-C (7). These compounds were isolated from this source for the first time. The compounds were tested for their cytotoxic activity against four human cancer cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) in vitro using the SRB method. Panaxydol (3) and panaxyne (6) showed significant and selective cytotoxicity against SK-OV-3 with ED50 values 2.93 and 1.40 μM, respectively.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Ahn, B. Z. and Kim, S. I., Relation between structure and cytotoxic activity of panaxydol analogs against L1210 cells. Arch. Pharm. (Weinheim, Germany), 321, 61–63 (1988).

    Article  CAS  Google Scholar 

  • Ahn, G. I., Park, C, H., Lee, E. O., Lee, H. J., Lee, J. H., Kim, K. H., Rhee, Y. H., Jang, Y. S., Kim, S. T., and Kim, S. H., Apoptotic effect of ethanol extracts of ojungbangamtang and acidic polysaccharide of Korea red ginseng in a MCF7/adR multidrug-resistance breast cancer cells. Yakhak Hoechi, 50, 272–277 (2006).

    CAS  Google Scholar 

  • Baek, N. I., Kim, D. S., Lee, Y. H., Park, J. D., Lee, Ch. B., and Kim I. S., Cytotoxicities of ginseng saponins and their degradation products against some cancer cell lines., Arch. Pharm. Res., 8, 164–168 (1995).

    Google Scholar 

  • Choi, Y. E., Kim, Y. S., Yi, M. J., Park, W. G., Yi, J. S., Chun, S. R., Han, S. S., and Lee, S. J., Physiological and chemical characteristics of field-and mountain-cultivated ginseng roots. J. Plant. Biol., 50, 198–205 (2007).

    Article  CAS  Google Scholar 

  • Fujimoto, Y., Satoh, M., Takeuchi, N., and Kirisawa, M., Cytotoxic acetylene from Panax quinquefolium. Chem. Pharm. Bull., 39, 521–523 (1991).

    PubMed  CAS  Google Scholar 

  • Fujimoto, Y., Wang, H., Satoh, M., and Takeuchi, N., Polyacetylenes from Panax quinquefolium. Phytochemistry, 35, 1255–1257 (1994).

    Article  CAS  Google Scholar 

  • Hirakura, K., Morita, M., Nakajima, K., Ikeya, Y., and Mitsuhashi, H., Polyacetylenes from the roots of Panax ginseng. Phytochemistry, 30, 3327–3333 (1991).

    Article  CAS  Google Scholar 

  • Hirakura, K., Morita, M., Nakajima, K., Ikeya, Y., and Mitsuhashi, H., The constituents of Panax ginseng. Part 3.Three acetylenic compounds from roots of Panax ginseng. Phytochemistry, 31, 899–903 (1992).

    CAS  Google Scholar 

  • Hirakura, K., Morita, M., Niitsu, K., Ikeya, Y., and Maruno, M., The constituents of Panax ginseng. Part 4. Linoleoylated polyacetylenes from the root of Panax ginseng. Phytochemistry, 35, 963–967 (1994).

    Article  CAS  Google Scholar 

  • Kang, K. S., Yokozawa, T., Yamabe, N., Kim, H. Y., and Park, J. H., ESR study on the structure and hydroxyl radical-scavenging activity relationships of ginsenosides isolated from Panax ginseng C. A. Meyer. Bio. Pharm. Bull., 30, 917–921 (2007).

    Article  Google Scholar 

  • Kim, S. I., Kang, K. S., Kim, H. Y., and Ahn, B. Z., Panaxyne, a new cytotoxic polyyne from Panax ginseng root against L1210 cell. Saengyak Hakhoechi, 20, 71–75 (1989).

    CAS  Google Scholar 

  • Kim, J. H. and Kim, J. K., Antioxidant activity and functional component analysis of Korean mountain Ginseng’s different sections. Han’guk Sikp’um Yongyang Kwahak Hoechi, 35, 1315–1321 (2006).

    CAS  Google Scholar 

  • Kitagawa, I., Taniyama, T., Yoshikawa, M., Ikennishi, Y., and Nakagawa, Y., Chemical studies on crude drug processing. VI. Chemical structures of malonyl-ginsenosides Rb1, Rb2, Rc, and Rd isolated from the root of Panax ginseng C. A. Meyer. Chem.Pharm.Bull., 37, 2961–2970 (1989).

    CAS  Google Scholar 

  • Lee, S. W., Kim, K., Rho, M. Ch., Chung, M. Y., Kim, Y. H., Lee, S. K., Lee, H. S., and Kim, Y. K., New polyacetylenes, DGAT inhibitors from the roots of Panax ginseng. Planta Medica, 70, 197–200 (2004).

    Article  PubMed  CAS  Google Scholar 

  • Lee, W. M., Kim, S. D., Kim, K. S., Song, Y. B., Kwak, Y. S., Cho, J. Y., Park, H. J., Oh, J. W., and Rhee, M. H., Proto-panaxadiol modulates LPS-induced inflammatory activity in murine macrophage RAW264.7 cells. J. Ginseng Res., 30, 181–187 (2006).

    Article  CAS  Google Scholar 

  • Mayer, S. F., Steinreiber, A., Orru, R. V. A., and Faber, K., Chemoenzymatic Asymmetric Total Syntheses of Antitumor Agents (3R,9R,10R)-and (3S,9R,10R)-Panaxytriol and (R)-and (S)-Falcarinol from Panax ginseng Using an Enantioconvergent Enzyme-Triggered Cascade Reaction. J. Org. Chem., 67, 9115–9121 (2002).

    Article  PubMed  CAS  Google Scholar 

  • Matsunaga, H., Katano, M., Yamamoto, H., Fujito, H., and Takata, K., Cytotoxic activity of poly-acetylene compounds in Panax ginseng C. A. Meyer. Chem. Pharm. Bull., 38, 3480–3482 (1990).

    PubMed  CAS  Google Scholar 

  • Park, J. D., Recent studies on the chemical constituents of Korean ginseng (Panax ginseng C. A. Meyer). J. Ginseng Res., 20, 389–415 (1996).

    CAS  Google Scholar 

  • Ryu, J. H., Jang, S. R., Lee, S. Y., Lee, H. J., and Han, Y. N., Inhibitors of nitric oxide synthesis from ginseng in activated macrophages. J. Ginseng Res., 22, 181–187 (1998).

    CAS  Google Scholar 

  • Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J.T., Bokesch, H., Kenney, S., and Boyd, M. R., New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 82, 1107–1112 (1990).

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Natural Products Laboratory, College of Pharmacy, Sungkyunkwan University, 300 Chonchon-dong, Jangan-ku, Suwon, 440-746, Korea

    Min Cheol Yang & Kang Ro Lee

  2. Faculty of Life Science and Technology, Sungkyunkwan University, Seoul, Korea

    Dong Sang Seo

  3. Korea Research Institute of Chemical Technology, Teajeon, 305-600, Korea

    Sang Un Choi

  4. Department of Food Science and Nutrition, Soonchunhyang University, Asan, 336-745, Korea

    Young Hyun Park

Authors
  1. Min Cheol Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Dong Sang Seo
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Sang Un Choi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Young Hyun Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Kang Ro Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Kang Ro Lee.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yang, M.C., Seo, D.S., Choi, S.U. et al. Polyacetylenes from the roots of cultivated-wild ginseng and their cytotoxicity in vitro . Arch. Pharm. Res. 31, 154–159 (2008). https://doi.org/10.1007/s12272-001-1134-1

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12272-001-1134-1

Key words

Search

Navigation