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Anti-inflammatory phenylpropanoid glycosides from Clerodendron trichotomum leaves

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  • Drug Discovery
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Abstract

The chromatographic separation of MeOH extract from Clerodendron trichotomum Thunberg leaves led to the isolation of three phenylpropanoid compounds. Using spectroscopic methods, the structures of these compounds were determined as β-(3′, 4′-dihydroxyphenyl)ethyl-O-α-L-rhamnopyranosyl (1→3)-β-D-(4-O-caffeoyl)-glucopyranoside, acteoside (verbascoside) (1), β-(3′, 4′-dihydroxyphenyl)ethyl-O-α-L-rhamnopyranosyl (1→3)-β-D-(6-O-caffeoyl)-glucopyranoside, isoacteoside (2), β-(3′, 4′-dihydroxyphenyl) ethyl-O-α-L-rhamnopyranosyl (1→3)-β-D-glucopyranoside, and decaffeoylacteoside (3). We measured the anti-inflammatory activity of these three phenylpropanoid compounds both in vitro (DPPH Reduction Assay, TBARS Assay on Cu 2+-induced oxidized LDL, PGE2 assay) and in vivo (acetic acidinduced vascular permeability in mice and carrageenan-induced hind paw edema in rats). 80% methanol fraction and acteoside had the activity.

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References

  • Andray, C., Wylde, R., Laffite, C., Privat, G., and Winternitz, F., Structure of Verbascoside and Orobanchoside, Caffeic acid sugar esters from Orobanche Rapum-Genistae, Phytochemistry, 21, 1123–1127 (1982).

    Article  Google Scholar 

  • Ahn, D. K., Illustrated Book of Korean Medicinal Herbs 6th edition, Kyo-Hak Publishing Co., Ltd, Seoul, p.323, (2003).

    Google Scholar 

  • Boadi, W. Y., Iyere, P. A., and Adunyah, S. E., Effect of Quercetin and Genistein on cupper- and iron-induced lipid peroxidation in methyl linolenate. J. Appl. Toxcicol., 23, 363–370 (2003).

    Article  CAS  Google Scholar 

  • Chae, S., Kim, J. S., Kang, K. A., Bu, H. D., Lee, Y., Seo, Y. R., Hyun, J. W., and Kang, S. S., Antioxidant activity of isoacteoside from Clerodendron trichotomum. J. Toxicol. Environ Health A, 68, 389–400 (2005).

    Article  PubMed  CAS  Google Scholar 

  • Choi, J. H., Whang, W. K., and Kim, H. J., Studies on the anti-inflammatory effects of Clerodendron trichotomum Thunberg leaves. Arch. Pharm. Res., 27, 189–193 (2004).

    Article  PubMed  CAS  Google Scholar 

  • Goncalves, C., Dinis, T., and Batista, M. T., Antioxidant properties of procyanidins of Uncaria tomentosa bark decoction: a mechanism for anti-inflammatory activity. Phytochemistry, 66, 89–98 (2005).

    Article  PubMed  CAS  Google Scholar 

  • Huang, K. C., The Pharmacology of Chinese Herbs. CRC Press, U.S.A., pp. 71–72, (1993).

    Google Scholar 

  • Hatano, T., Edamatsu, R., Hiramatsu, M., Mori, A., Fujita, Y., Yasuhara, T., Yoshida, T., and Okuda, T., Effects of tannins with co-existing substances. VI. Effects of tannins and related polyphenols on superoxide anion radical, and on 1,1-diphenyl-2-picrylhydrazyl radical. Chem. Pharm. Bull., 37, 2016–2021 (1989)

    CAS  Google Scholar 

  • Inchi, T., Shimizu, T., and Yoshihira, K., Biotechnology in Agriculture and Forestry. Berlin Heidelberg, 37, 108 (1996).

    Google Scholar 

  • Iwadare, S., Shizuri, Y., Sasaki, K., and Hirata, Y., Isolation and structure of trichotomine and trichotomine G1. Tetrahedron, 30, 4105–4111 (1974).

    Article  CAS  Google Scholar 

  • Kato, N., Shibayama, S., Munakata, K., and Katayama, C., Structure of the diterpene clerodendrin A. Journal of the Chemical Society [Section] D: Chemical Communications, 24, 1632–1633 (1971).

    Article  Google Scholar 

  • Kawai, K., Nishida, R., and Fukami, H., Clerodeneron I, a new neoclerodane diterpenoid from Clerodendron trichotomum. Biosci. Biotechnol. Biochem., 63, 1795–1797 (1999).

    Article  CAS  Google Scholar 

  • Kim, T. J., Korean floral resources. Seoul Univ., Korea, (1996).

    Google Scholar 

  • Kim, H. J., Woo, E. R., Shin, C. G., Hwang, D. J., Park, H., and Lee, Y. S., HIV-1 integrase inhibitory phenylpropanoid glycosides from Clerodendron trichotomum. Arch. Pharm. Res., 24, 286–291 (2001).

    Article  PubMed  CAS  Google Scholar 

  • Lee, C. B., An illustrated book of Korean plant. Hyang Mun publishing company, Korea, (1973).

    Google Scholar 

  • Lee, J. Y., Woo, E. R., and Kang, K. W., Inhibition of lipopolysaccharide-inducible nitric oxide synthase expression by acteoside through blocking of AP-1 activation. J. Ethnophamacol., 97, 561–566 (2005).

    Article  CAS  Google Scholar 

  • Lee, W. T., Lineamenta Florae Koreae. 1st edition, Academic Books, Seoul, pp 934–935, (1996).

    Google Scholar 

  • Morita, N., Arisawa, M., Ozawa, H., Chen, C. S., and Kan, W. S., Clerodendroside, a new glycoside from the leaves of Clerodendron trichotomum Thunb. var fargesii Rehd. Yakugaku zasshi, 97, 976–979 (1977).

    PubMed  CAS  Google Scholar 

  • Otsuka, H., Kashima, N., Hayashi, T., Kubo, N., Yamasaki, K., and Padolina, W. G., Premnaodorosides A, B and C, iridoid glucoside diesters of acyclic monoterpenediol from leaves of Premna odorata. Phytochemistry, 31, 3129–3133 (1992).

    Article  CAS  Google Scholar 

  • Park, M. A. and Kim, H. J., Anti-inflammatory constituents isolated from Clerodendron trichotomum Thunberg Leaves (CTL) inhibits pro-inflammatory gene expression in LPS-stimulated RAW 264.7 macrophages by suppressing NF-κB activation. Arch. Pharm. Res., 30, 755–760 (2007).

    Article  PubMed  CAS  Google Scholar 

  • Raguenes-Nicol, C., Russo-Marie, F., Domage, G., Diab, N., Solito, E., Dray, F., Mace, J. G., and Streichenberger, G., Anti-inflammatory mechanism of alminoprofen: action on the phospholipid metabolism pathway. Biochem. Pharmacol., 57, 433–443 (1999).

    Article  PubMed  CAS  Google Scholar 

  • Sakurai, A. and Kato, T., A new glycoside, kusaginin isolated from Clerodendron trichotomum. Bull. Chem. Soc. Jpn., 56, 1573–1574 (1983).

    Article  CAS  Google Scholar 

  • Winter, C. A., Risley, E. A., and Nuss, G. W., Carageenan-induced edema in hind paw of the rat as an assay for anti-inflammatory drugs. Proc. Soc. Exp. Biol. Med., 111, 544–547 (1962).

    PubMed  CAS  Google Scholar 

  • Whittle, B. A., The use of changes in capillary permeability in mice to distinguish between narcotic and nonnarcotic anagesics. Brit. J. Pharmacol., 22, 246–253 (1964).

    PubMed  CAS  Google Scholar 

  • Zimin, L. and Zhongjian, J., Phenylpropanoid and iridoid glycosides from Pedicularis striata, Phytochemistry, 30, 1341–1344 (1990).

    Article  Google Scholar 

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Correspondence to Wan Kyunn Whang.

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Kim, K.H., Kim, S., Jung, M.Y. et al. Anti-inflammatory phenylpropanoid glycosides from Clerodendron trichotomum leaves. Arch. Pharm. Res. 32, 7–13 (2009). https://doi.org/10.1007/s12272-009-1112-6

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  • DOI: https://doi.org/10.1007/s12272-009-1112-6

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