Archives of Pharmacal Research

, Volume 31, Issue 5, pp 666–670 | Cite as

A new pancreatic lipase inhibitor isolated from the roots of Actinidia arguta

  • Dae Sik Jang
  • Ga Young Lee
  • Junghyun Kim
  • Yun Mi Lee
  • Jong Min Kim
  • Young Sook Kim
  • Jin Sook Kim
Articles Drug Efficacy and Safety

Abstract

A new coumaroyl triterpene, 3-O-trans-p-coumaroyl actinidic acid (1), as well as five known triterpenes, ursolic acid (2), 23-hydroxyursolic acid (3), corosolic acid (4), asiatic acid (5) and betulinic acid (6) were isolated from an EtOAc-soluble extract of the roots of Actinidia arguta. The structure of compound 1 was elucidated from interpretation of the spectroscopic data, particularly by extensive 1D and 2D NMR studies. All the isolates (1–6) were evaluated in vitro for their inhibitory activities on pancreatic lipase (PL). Of the isolates, the new compound 1 possessed the highest inhibitory activity on PL, with an IC50 of 14.95 μM, followed by ursolic acid (2, IC50 = 15.83 μM). The other four triterpenes (3–6) also showed significant PL inhibitory activity, with IC50 values ranging from 20.42 to 76.45 μM.

Key words

Actinidia arguta Actinidiaceae 3-O-trans-p-Coumaroyl actinidic acid Triterpene Pancreatic lipase Obesity 

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References

  1. Aquino, R., De Simone, F., Vincieri, F. F., Pizza, C., and Gacs-Baitz, E., New polyhydroxylated triterpenes from Uncaria tomentosa. J. Nat. Prod., 53, 559–564 (1990).PubMedCrossRefGoogle Scholar
  2. Aguirre, M. C., Delporte, C., Backhouse, N., Erazo, S., Letelier, M. E., Cassels, B. K., Silva, X., Alegría, S., and Negrete, R., Topical anti-inflammatory activity of 2α-hydroxy pentacyclic triteroene acids from the leaves of Ugni molinae. Bioorg. Med. Chem., 14, 5673–5677 (2006).PubMedCrossRefGoogle Scholar
  3. Ballinger, A. and Peikin, S. I. R., Orlistat: Its current status as an anti-obesity drug. Eur. J. Pharm. Sci., 440, 109–117 (2002).CrossRefGoogle Scholar
  4. Birari, R. B. and Bhutani, K. K., Pancreatic lipase inhibitors from natural sources: unexplored potential. Drug Discov. Today, 12, 879–889 (2007).PubMedCrossRefGoogle Scholar
  5. Borgstrom, B., Exocrine Pancreas, Pathology and Diseases. Raven Press, New York, pp. 361–401, (1981).Google Scholar
  6. Budzikiewicz, H., Wilson, J. M., and Djerassi, C., Mass spectrometry in structural and stereochemical problems. XXXII. Pentacyclic triterpenes. J. Am. Chem. Soc., 85, 3688–3699 (1963).CrossRefGoogle Scholar
  7. Chung, M. Y., Rho, M. C., Lee, S. W., Park, H. R., Kim, K., Lee, I. A., Kim, D. H., Jeune, K. H., Lee, H. S., and Kim, Y. K., Inhibition of diacylglycerol acyltransferase by betulinic acid from Alnus hirsuta. Planta Med., 72, 267–269 (2006).PubMedCrossRefGoogle Scholar
  8. Drent, M. L. and van der Veen, E. A., Lipase inhibition: a novel concept in the treatment of obesity. Int. J. Obes., 17, 241–244 (1993).Google Scholar
  9. Ferguson, R., Actinidia arguta — the hardy kiwifruit. New Zealand Kiwifruit, 81, 23–24 (1991).Google Scholar
  10. Gargouri, Y., Ransac, S., and Verger, R., Covalent inhibition of digestive lipases: an in vitro study. Biochim. Biophys. Acta, 1344, 6–37 (1997).PubMedGoogle Scholar
  11. Jang, D. S., Kim, J. M., Lee, G. Y., Kim, J.-H., and Kim, J. S., Ursane-type triterpenoids from the aerial parts of Potentilla discolor. Agric. Chem. Biotechnol., 49, 48–50 (2006).Google Scholar
  12. Jayaprakasam, B., Olson, L. K., Schutzki, R. E., Tai, M.-H., and Nair, M. G., Amelioration of obesity and glucose intolerance in high-fat-fed C57BL/6 mice by anthocyanins and ursolic acid in cornelian cherry (Cornus mas). J. Agric. Food Chem., 54, 243–248 (2006).PubMedCrossRefGoogle Scholar
  13. Kim, J.-G. and Xiao, P.-G., Traditional Drugs of the East Color Edition. Young-Rim Publishing Co., Seoul, p. 207, (1995).Google Scholar
  14. Kim, J. H., Kim, H. J., Park, H. W., Youn, S. H., Choi, D. Y., and Shin, C. S., Development of inhibitors against lipase and alpha-glucosidase from derivatives of monascus pigment. FEMS Microbiol. Lett., 276, 93–98 (2007).PubMedCrossRefGoogle Scholar
  15. Lahlou, E. H., Hirai, N., Kamo, T., Tsuda, M., and Ohigashi, H., Actinidic acid, a new triterpene phytoalexin from unripe kiwi fruit. Biosci. Biotechnol. Biochem., 65, 480–483 (2001).PubMedCrossRefGoogle Scholar
  16. Lim, H.-W., Kang, S.-J., Park, M., Yoon, J. H., Han, B.-H., Choi, S.-E., and Lee, M.-W., Anti-oxidative and nitric oxide production inhibitory activities of Phenolic compounds from the fruits of Actinidia arguta. Nat. Prod. Sci., 12, 221–225 (2006).Google Scholar
  17. Nakai, M., Fukui, Y., Asami, S., Toyoda-Ono, Y., Iwashita, T., Shibata, H., Mitsunaga, T., Hashimoto, F., and Kiso, Y., Inhibitory effects of oolong tea polyphenols on pancreatic lipase in vitro. J. Agric. Food Chem., 53, 4593–4598 (2005).PubMedCrossRefGoogle Scholar
  18. Ruiz, C., Falcocchio, S., Xoxi, E., Villo, L., Nicolosi, G., Pastor, F. I. J., Diaz, P., and Saso, L., Inhibition of Candida rugosa lipase by saponins, flavonoids and alkaloids. J. Mol. Catal. B-Enzym., 40, 138–143 (2006).CrossRefGoogle Scholar
  19. Sashida, Y., Ogawa, K., Mori, N., and Yamanouchi, T., Triterpenoids from the fruit galls of Actinidia polygama. Phytochemistry, 31, 2801–2904 (1992).CrossRefGoogle Scholar
  20. Webby, R. F. and Markham, K. R., Flavonol 3-O-triglycosides from Actinidia species. Phytochemistry, 29, 289–292 (1990).CrossRefGoogle Scholar
  21. Whang, J. I., Moon, H. I., and Zee, O. P., Phytochemical constituents of Actinidia arguta. Kor. J. Pharmacogn., 31, 357–363 (2000).Google Scholar
  22. Yanovski, S. J. and Yanovski, J. A., Obesity. New Engl. J. Med., 346, 591–602 (2002).PubMedCrossRefGoogle Scholar
  23. Yoshikawa, Y., Shimoda, H., Nishida, N., Takada, M., and Matsuda, H., Salacia reticulata and its polyphenolic constituents with lipase inhibitory and lipolytic activities have mild antiobesity effects in rats. J. Nutr., 132, 1819–1824 (2002).PubMedGoogle Scholar

Copyright information

© The Pharmaceutical Society of Korea 2008

Authors and Affiliations

  • Dae Sik Jang
    • 1
  • Ga Young Lee
    • 1
  • Junghyun Kim
    • 1
  • Yun Mi Lee
    • 1
  • Jong Min Kim
    • 1
  • Young Sook Kim
    • 1
  • Jin Sook Kim
    • 1
  1. 1.Department of Herbal Pharmaceutical DevelopmentKorea Institute of Oriental MedicineDaejeonKorea

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