Advances in Traditional Medicine

Kyung Hee Oriental Medicine Research Center (경희대학교 융합한의과학연구소)
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Effects of dihydrocubebin, a lignan isolated from Indonesian plant Piper cubeba, on the histamine release from rat mast cells

  • Nugroho, Agung Endro (Department of Pharmacology, Informational Biomedicine, Ehime University Graduate School of Medicine) ;
  • Wahyono, Wahyono (Department of Pharmaceutical Biology, Faculty of Pharmacy, Gadjah Mada University) ;
  • Wahyuono, Subagus (Department of Pharmaceutical Biology, Faculty of Pharmacy, Gadjah Mada University) ;
  • Maeyama, Kazutaka (Department of Pharmacology, Informational Biomedicine, Ehime University Graduate School of Medicine)
  • Received : 2009.02.25
  • Accepted : 2010.09.07
  • Published : 2010.09.30
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Abstract

The fruits of Piper cubeba L. are used traditionally to treat respiratory disorders in Indonesia. In order to determine the compounds responsible for this activity, the fruits were extracted with nhexane followed by ethanol to give n-hexane and ethanol extracts. Based on tracheospasmolytic assay on these two extracts, the n-hexane extract was more active to inhibit trachea contraction than that of ethanol extract. Upon bioassay guided isolation of the n-hexane extract, a tracheospasmolytic active compound was isolated and identified as dihydrocubebin [(3,4),(3',4')-bis-methylenedioxy-9,9'dihydroxylignan] $(\underline{1})$. Compound $\underline{1}$ was tested further for its ability to inhibit histamine released from mast cells, using rat basophilic leukemia (RBL-2H3) cell line and rat peritoneal mast cells RPMCs) as models; and $DNP_{24}$-BSA, thapsigargin, ionomycin, compound 48/80 and PMA were used as inducers for histamine released from mast cell. The test result showed that $\underline{1}$ inhibited histamine release from RBL-2H3 cells induced by $DNP_{24}$-BSA, thapsigargin and ionomycin. In addition, $\underline{1}$ suppressed histamine release from RPMC induced by either thapsigargin or ionomycin. However, $\underline{1}$ did not inhibit histamine release from RPMC induced by either compound 48/80 or combination PMA-sub optimum dose of ionomycin. Therefore, it was concluded that the inhibitory effects of $\underline{1}$ on the histamine released from mast cells may involve mechanisms related to intracellular $Ca^{2+}$ signaling events or downstream processes of intracellular $Ca^{2+}$ signaling in mast cells.

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References

  1. Barnes PJ. (1999) Therapeutic strategies for allergic diseases. Nature 402, B31-38.
  2. Barsumian EL, Isersky C, Petrino MG, Siraganian RP. (1981) IgE-induced histamine release from rat basophilic leukemia cell lines. Eur. J. Immunol. 11, 317-323. https://doi.org/10.1002/eji.1830110410
  3. Bergstrand H, Lundquist B, Karabelas K, Michelsen P. (1992) Modulation of human basophil histamine release by protein kinase C inhibitors differs with secretagogue and with inhibitor. J. Pharmacol. Exp. Ther. 260, 1028-1037.
  4. Bottcher I, Ulrich M, Hirayama N, Ovary Z. (1980) Production of monoclonal mouse IgE antibodies with DNP specificity by hybrid cell lines. Int. Arch. Allergy. Appl. Immunol. 61, 248-250. https://doi.org/10.1159/000232441
  5. Brown JM, Wilson TM, Metcalfe DD. (2008) The mast cell and allergic diseases: role in pathogenesis and implications for therapy. Clin. Exp. Allergy. 38, 4-18.
  6. Busse WW, Reed CE. (1993) Asthma : Definition and pathogenesis, In : Middleton, E., Jr., Reed CE, Ellis EF, Adkinson NF Jr., Yunginger JW, Busse WW. (Eds.). Allergy, Principles and Practice, vol. I, 4th Ed., Mosby, Inc., St. Louis, Missouri, p. 1173.
  7. Chakravarty N. (1990) The role of protein kinase C in the histamine secretion from mast cell. Acta Physiol. Scand. 139, 319-333. https://doi.org/10.1111/j.1748-1716.1990.tb08930.x
  8. Heiman AS, Crews FT. (1985) Characterization of the effects of phorbol esters on rat mast cell secretion. J. Immunol. 134, 548-555.
  9. Hirata N, Naruto S, Inaba K, Itoh K, Tokunaga M, Iinuma M, Matsuda H. (2008) Histamine release inhibitory activity of Piper nigrum leaf. Biol. Pharm. Bull. 31, 1973-1976. https://doi.org/10.1248/bpb.31.1973
  10. Holt PG, Macaubas C, Stumbles PA, Sly PD. (1999) The role of allergy in the development of asthma. Nature 402, B12-17.
  11. Huang Y, Putney JW Jr. (1998) Relationship between intracellular calcium store depletion and calcium release-activated calcium current in a mast cell line (RBL-1). J. Biol. Chem. 273, 1954-1959.
  12. Ikawati Z, Wahyuono S, Maeyama K. (2001) Screening of several Indonesian medicinal plants for their inhibitory effect on histamine release from RBL-2H3 cells. J. Ethnopharmacol. 75, 249-256. https://doi.org/10.1016/S0378-8741(01)00201-X
  13. Katakami Y, Kaibuchi K, Sawamura M, Takai Y, Nishizuka Y. (1984) Synergistic action of protein kinase C and calcium for histamine release from rat peritoneal mast cells. Biochem. Biophys. Res. Commun. 121, 573-578. https://doi.org/10.1016/0006-291X(84)90220-1
  14. Liu WC, Slusarchyk DS, Astle G, Trejo WH, Brown WE, Meyers E. (1978) Ionomycin, a new polyether antibiotic. J. Antibiot. (Tokyo) 31, 815-819. https://doi.org/10.7164/antibiotics.31.815
  15. Liu FT, Bohn JW, Ferry EL, Yamamoto H, Molinaro CA, Sherman LA, Klinman NR, Katz DH. (1980) Monoclonal dinitrophenyl-specific murine IgE antibody: preparation, isolation, and characterization. J. Immunol. 124, 2728-2737.
  16. Metcalfe DD, Baram D, Mekori YA. (1997) Mast cells. Physiol. Rev. 77, 1033-1064. https://doi.org/10.1152/physrev.1997.77.4.1033
  17. Mousli M, Bronner C, Landry Y, Bockaert J, Rouot B. (1990) Direct activation of GTP-binding regulatory proteins (G-proteins) by substance P and compound 48/80. FEBS Lett. 259, 260-262. https://doi.org/10.1016/0014-5793(90)80023-C
  18. Nayampali SS, Satoskar RS. (1980) Evaluation of antiallergenic activity of Piper longum using rat-lung perfusion technique, in Proc. 13th Annual Conf. Indian Pharmacol. Soc., Regional Res., September 30th – October 2nd, Lab. Jammu-Tawi India.
  19. Okano Y, Takagi H, Nakashima S, Tohmatsu T, Nozawa Y. (1985) Inhibitory action of phorbol myristate acetate on histamine secretion and polyphosphoinositide turnover induced by compound 48/80 in mast cells. Biochem. Biophys. Res. Commun. 132, 110-117. https://doi.org/10.1016/0006-291X(85)90995-7
  20. Okano Y, Yamada K, Takagi H, Nozawa Y. (1986) Biphasic effect of phorbol myristate acetate on histamine secretion induced by compound 48/80 in rat peritoneal mast cells. Biochem. Biophys. Res. Commun. 137, 1112-1118. https://doi.org/10.1016/0006-291X(86)90340-2
  21. Palomaki VA, Laitinen JT. (2006) The basic secretagogue compound 48/80 activates G proteins indirectly via stimulation of phospholipase D-lysophosphatidic acid receptor axis and 5-HT1A receptors in rat brain sections. Br. J. Pharmacol. 147, 596-606. https://doi.org/10.1038/sj.bjp.0706671
  22. Patkar SA, Rasmussen U, Diamant B. (1979) On the mechanism of histamine release induced by thapsigargin from Thapsia garganica L. Agents Actions 9, 53-57. https://doi.org/10.1007/BF02024109
  23. Prabhu BR, Mulchandani NB. (1985) Lignans from Piper cubeba. Phytochemistry 24, 329-331. https://doi.org/10.1016/S0031-9422(00)83546-3
  24. Shin TY. (2004) Stachys riederi inhibits mast cellmediated acute and chronic allergic reactions. Immunopharmacol Immunotoxicol. 26, 621-630. https://doi.org/10.1081/IPH-200042365
  25. Thastrup O, Cullen PJ, Drobak BK, Hanley MR, Dawson AP. (1990) Thapsigargin, a tumor promoter, discharges intracellular $Ca^{2+}$ stores by specific inhibition of the endoplasmic reticulum $Ca^{2+}$-ATPase. Proc. Natl. Acad. Sci. U S A 87, 2466-2470. https://doi.org/10.1073/pnas.87.7.2466
  26. Wahyono S. (2005) Isolation and Structure Elucidation of Tracheospasmolytic Compounds from Piper cubeba L.f Fruits., Dissertation, Gadjah Mada University, Indonesia.
  27. Wahyuono S, Mulyono, Wahyono, Mursyidi A. (1999) Tracheospasmolytic activity of Piper cubeba L.f. fructus. Indian J. Pharm. 10, 48-56.
  28. Westley JW, Liu CM, Evans RH, Blount JF. (1979) Conglobatin, a novel macrolide dilactone from Streptomyces conglobatus ATCC 31005. J. Antibiot. (Tokyo) 32, 874-877. https://doi.org/10.7164/antibiotics.32.874
  29. Wirotesangthong M, Inagaki N, Tanaka H, Thanakijcharoenpath W, Nagai H. (2008) Inhibitory effects of Piper betle on production of allergic mediators by bone marrow-derived mast cells and lung epithelial cells. Int. Immunopharmacol. 8, 453-457. https://doi.org/10.1016/j.intimp.2007.11.005
  30. Yamatodani A, Fukuda H, wada H, Iwaeda T, Watanabe T. (1985) High-performance liquid chromatographic determination of plasma and brain histamine without previous purification of biological samples: cation-exchange chromatography coupled with post-column derivatization fluorometry. J. Chromatogr. 344, 115-123. https://doi.org/10.1016/S0378-4347(00)82012-5
  31. Yen A, Barrett KE, Gigli I. (1992) Protoporphyrin and long-wave ultraviolet light modulate metabolic events in rat peritoneal mast cells. J. Invest. Dermatol. 98, 488-493. https://doi.org/10.1111/1523-1747.ep12499864