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Inhibitory Constituents against Cyclooxygenases fromAralia cordata Thunb

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Abstract

Seven diterpenes, four polyacetylenes, a lipid glycerol, and two sterols were isolated from the methylene chloride fraction of the root ofAralia cordata. Their chemical structures were determined as (-)-pimara-8(14),15-dien-19-oic acid (2), pimaric acid (3), (-)-kaur-16-en-19-oic acid (4), 17-hydroxy-ent-kaur-15-en-19-oic acid (9), 7α-hydroxy-(-)-pimara-8(14),15-dien-19-oic acid (10), 16α, 17-dihydroxy-(-)-kauran-19-oic acid (11), 16-hydroxy-17-isovaleroyloxy-ent-kauran-19-oic acid (12), falcarindiol (5), dehydrofalcarindiol (6), dehydrofalcarindiol-8-acetate (7), falcarindiol-8-acetate (8), alpha-mono palmitin (13), stigmasterol (1), and daucosterol (14) by the spectral evidences. These compounds were tested with COX-1 and COX-2 inhibition assays. This study found that compounds2, 4, 5, 6, 7, 8, and10 inhibited COX-1 dependent conversion of the exogenous arachidonic acid to PGE2 in a dose-dependent manner with IC50 values of 134.2 μM, 121.6 μM, 170 μM, 50.4 μM, 11.7 μM, 99.6 μM, and 69.6 μM, respectively. But, most of these compounds weakly inhibited COX-2 dependent PGE2 generation. Among them, only compound 4 showed relatively significant inhibitory activity (IC50: 127.6 μM).

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References

  • Andreas, C. and Thomas, H., Structural and sensory characterization of compounds contributing to the bitter off-taste of carrots (Daucus carota L.) and carrot puree.J. Agric. Food Chem., 51, 3865–3873 (2003).

    Article  CAS  Google Scholar 

  • Bernart, W. M., Cardellina, H. J., Balaschak, S. M., Alexander, R. M., Shoemaker, H. R., and Boyd, R. M., Cytotoxic falcarinol oxylipins fromDendropanax arboreus.J. Nat. Prod., 59, 748–753 (1996).

    Article  PubMed  CAS  Google Scholar 

  • Chang, F. R., Yang, P. Y., Lin, J. Y., Lee, K. H., and Wu, Y. C., Bioactive kaurane diterpenoids fromAnnona glabra.J. Nat. Prod., 61, 437–439 (1998).

    Article  PubMed  CAS  Google Scholar 

  • Emery, P., COX-1, COX-2: So what?Scand.J. Rheumatol., 28, 6–9 (1999).

    CAS  Google Scholar 

  • Han, B. H., Han, Y. N., Han, L. A., Park, M. H., and Lee, E. O., Studies on the anti-inflammatory activity ofAralia continentalis (I).Arch. Pharm. Res., 6, 17–23 (1983).

    Article  CAS  Google Scholar 

  • Hung, C. Y. and Yen, G. C., Extraction and identification of anti-oxidative components of Hsian-tsao (Mesona procumbens Hemsl.).Lebensm.-Wiss. u.-Technol., 34, 306–311 (2001).

    Article  CAS  Google Scholar 

  • Kim, J. S. and Kang, S. S., Saponins from the aerial parts ofAralia continentalis.Natural Products Sciences, 4, 45–50 (1998).

    CAS  Google Scholar 

  • Kwon, H. C. and Lee, K. R., Phytochemical constituents ofArtemisia japonica ssp. littoricola.Arch. Pharm. Res., 24, 194–197 (2001).

    Article  PubMed  CAS  Google Scholar 

  • Matsuo, A., Uto, S., Nakayama, M., Hayashi, S., Yamasaki, K., Kasai, R., and Tanaka, O., (-)-Thermarol. A new ent-pimarane-class diterpene diol fromJungermannia thermerum (liverwort).Tetrahedron Letters, 28, 2451–2454 (1976).

    Article  Google Scholar 

  • Mihashi, S., Yanagisawa, I., Tanaka, O., and Shibata, S., Further study on the diterpenes ofAralia spp.Tetrahedron Lett., 21, 1683–1686 (1969).

    Article  PubMed  CAS  Google Scholar 

  • Okuyama, E., Nishimura, S., and Yamazaki, M., Analgesic principles fromAralia cordata Thunb.Chem. Pharm. Bull., 39, 405–407 (1991).

    PubMed  CAS  Google Scholar 

  • Okuyama, E., Nishimura, S., Ohmori, S., Ozaki, Y., Satake, M., and Yamazaki, M., Analgesic components ofNotopterygium incisum Ting.Chem. Pharm. Bull., 41, 926–929 (1993).

    PubMed  CAS  Google Scholar 

  • Park, S. Y. and Kim, J. W., Cytotoxic polyacetylenes fromAralia cordata.Yakhak Hoeji, 39, 681–688 (1995).

    CAS  Google Scholar 

  • Rahman, A. and Ahmad, V. Q.,13C-NMR of natural products.Plenum Press, 2, 258 (1992).

    Google Scholar 

  • Sang, S. M., Kikuzaki, H., Lapsley, K., Rosen, R. T., Nakatani, N., and Ho, C. T., Sphingolipid and other constituents from almond nuts (Prunus amygdalucs Batsch).J. Agric. Food Chem., 50, 4709–4712 (2002).

    Article  PubMed  CAS  Google Scholar 

  • Shibata, S., Mihashi, S., and Tanaka, O., The occurrence of (-) pimarane-type diterpene inAralia cordata Thunb.Tetrahedron Lett., 51, 5241–5243 (1967).

    Article  Google Scholar 

  • Silva, E. A., Takashi, J. A., Boaventura, M. A. D., Oliveira, A. B., The biotransformation of ent-kaur-16-en-19-oic acid byRhizopus stolonifer.Phytochemistry, 52, 397–400 (1999).

    Article  PubMed  CAS  Google Scholar 

  • Tanaka, O., Mihashi, S., Yanagisawa, I., Niaido, T., and Shibata, S., Diterpenes ofAralia cordata: Oxidative transformation of 4-axial aldehyde of some diterpenes and a note to the naturally occurring 4-hydroxy-18 (or 19) norditerpenes.Tetrahedron, 28, 4523–4537 (1972).

    Article  CAS  Google Scholar 

  • Yahara, S., Ishida, M., Yamazaki, K., Tanaka, O., and Mihashi, S., Minor diterpenes ofAralía cordata Thunb: 17-hydroxy-ent-kaur-15-en-19-oic acid and grandifloric acid.Chem. Pharm. Bull., 22, 1629–1631 (1974).

    PubMed  CAS  Google Scholar 

  • Ylva, N., Therese, R., Premila, P., Helena, D., and Lars, B., Development of a Radiochemical Cyclooxygenase-1 and 2in vitro assay for identification of natural products as inhibitor of prostaglandin biosynthesis.J. Nat. Prod., 61, 2–7 (1998).

    Article  Google Scholar 

  • Zhang, Y. M., Yang, J. S., and Xu, X. D., A new kaurane derivative fromAralia fargesii.Chinese Chemical Letters, 10, 673–674 (1999).

    CAS  Google Scholar 

  • Zheng, G., Lu, W., and Cai, J., Stereoselective total synthesis of (3R, 8S)-falcarindiol, a common polyacetylene compound fromUmbellifers.J. Nat. Prod., 62, 626–628 (1999).

    Article  PubMed  CAS  Google Scholar 

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Correspondence to KiHwan Bae.

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Dang, N.H., Zhang, X., Zheng, M. et al. Inhibitory Constituents against Cyclooxygenases fromAralia cordata Thunb. Arch Pharm Res 28, 28–33 (2005). https://doi.org/10.1007/BF02975131

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