Archives of Pharmacal Research

, Volume 33, Issue 12, pp 1927–1932 | Cite as

A new triterpene and an antiarrhythmic liriodendrin from Pittosporum brevicalyx

  • Chun Feng
  • Bo-Gang Li
  • Xiao-Ping Gao
  • Hua-Yi Qi
  • Guo-Lin Zhang
Research Articles Drug Discovery and Development


A new triterpene, 21-O-senecioyl-R1-barrigenol (1) and 13 known compounds were isolated from the ethanol extracts of the leaves and bark of Pittosporum brevicalyx (Oliv.) Gagnep. Their structures were elucidated based on spectral data. The antiarrhythmic action of one furofuran lignan, liriodendrin (2), was tested on a model of CaCl2-induced arrhythmia and compared with the effect of verapamil. The prophylactic administration of liriodendrin (2) was effective in prolonging latency of arrhythmia and reducing the occurrence of ventricular fibrillation from 75% to 25%. The overall mortality rate was significantly reduced by the prophylactic administration of liriodendrin from 87.5% to 25%. The antiarrhythmic effect of liriodendrin (5.0 mg/kg) was similar to that of verapamil (1.05 mg/kg). Thus, liriodendrin may be a potent suppressor of CaCl2-induced arrhythmias.

Key words

Pittosporum brevicalyx Liriodendrin Antiarrhythmic CaCl2-induced arrhythmias 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Aurada, E., Jurenitsch, J., and Kubelka, W., Structure of triterpene sapogenins of Aesculus glabra. Planta Med., 50, 391–394 (1984).CrossRefPubMedGoogle Scholar
  2. Bergeron, C., Marston, A., Antus, S., Gauthier, R., and Hostettmann, K., Flavonoids from Pyrola elliptica. Phytochemistry, 49, 233–236 (1998).CrossRefGoogle Scholar
  3. Cheung, B. M. and Kumana, C. R., Calcium channel blockers revisited. Hong Kong Med. J., 8, 300–301 (2002).PubMedGoogle Scholar
  4. Chollet-Debord, F., Moins, N., Gachon, P., and Duchene-Marullaz, P., Comparison of verapamil and bepridil, two slow channel inhibitors, in protection against calcium-induced arrhythmias. Naunyn Schmiedebergs Arch. Pharmacol., 334, 105–109 (1986).CrossRefPubMedGoogle Scholar
  5. D’Acquarica, I., Di Giovanni, M. C., Gasparrini, F., Misiti, D., D’Arrigo, C., and Fagnano, N., Isolation and structure elucidation of four new triterpenoid estersaponins from fruits of Pittosporum tobira AIT. Tetrahedron, 58, 10127–10136 (2002).CrossRefGoogle Scholar
  6. Deyama, T., Nishibe, S., and Nakazawa, Y., Constituents and pharmacological effects of Eucommia and Siberian ginseng. Acta Pharmacol. Sin., 22, 1057–1070 (2001).PubMedGoogle Scholar
  7. Dickey, E. E., Liriodendrin, a new lignan diglucoside from the inner bark of yellow poplar (Liriodendron tulipifera. L). J. Org. Chem., 23, 179–184 (1958).CrossRefGoogle Scholar
  8. Du, N. S., Ma, C., and Zhang, X., Blood lipid reducing effect of Poacynum hendersonii leaf aqueous extracts and two compounds therein. CHN Patent, 1748723 (2006).Google Scholar
  9. Fujiwara, Y., Hashimoto, K., Manabe, K., and Maoka, T., Structures of tobiraxanthins A1, A2, A3, B, C and D, new carotenoids from the seeds of Pittosporum tobira. Tetrahedron Lett., 43, 4385–4388 (2002).CrossRefGoogle Scholar
  10. Hammami, S., Ben, J. H., Bergaoui, A., Ciavatta, L., Cimino, G., and Mighri, Z., Isolation and structure elucidation of a flavanone, a flavanone glycoside and vomifoliol from Echiochilon fruticosum growing. Molecules, 9, 602–608 (2004).CrossRefPubMedGoogle Scholar
  11. Institute of Botany, Chinese Academy of Science & Institute of Material Medical, Chinese Academy of Medical Science, Flora Reipublicae Popularis sinicae, Vol. 35, Science Press, Beijing, pp. 1, (1992).Google Scholar
  12. Institute of Botany, Chinese Academy of Science & Institute of Material Medical, Chinese Academy of Medical Science, Flora Reipublicae Popularis sinicae, Vol. 35, Science Press, Beijing, pp. 32–33 (1992).Google Scholar
  13. John, A. J., Karunakaran, V. P., George, V., Pradeep, N. S., and Sethuraman, M. G., Constituents and antibacterial activity of the essential oils from the leaves and fruits of Pittosporum viridulum. J. Essent. Oil Res., 19, 591–593 (2007).Google Scholar
  14. Jolad, S. D., Hoffmann, J. J., Cole, J. R., Tempesta, M. S., and Bates, R. B., Cytotoxic agent from Penstemon deustus (Scrophulariaceae): isolation and stereochemistry of liriodendrin, a symmetrically substituted furofuranoid lignan diglucoside. J. Org. Chem., 45, 1327–1329 (1980).CrossRefGoogle Scholar
  15. Jung, H. J., Park, H. J., Kim, R. G., Shin, K. M., Ha, J., and Choi, J. W., In vivo anti-inflammat ory and antinociceptive effects of liriodendrin isolated from the stem bark of Acanthopanax senticosus. Planta Med., 69, 610–616 (2003).CrossRefPubMedGoogle Scholar
  16. Kosuge, K., Mitsunaga, K., Koike, K., and Ohmoto, T., Studies on the constituents of Ailanthus integrifolia. Chem. Pharm. Bull., 42, 1669–1671 (1994).PubMedGoogle Scholar
  17. Malinow, M. R., Battle, F. F., and Malamud, B., Nervous mechanisms in ventricular arrhythmias induced by calcium chloride in rats. Circ. Res., 1, 554–559 (1953).PubMedGoogle Scholar
  18. Olugbade, T. A., Ogunfaini, A., Birlirakis, N., Pais, M., and Martin, M. T., Petersaponins III and IV, Triterpenoid saponins from Petersianthus macrocarpus. J. Nat. Prod., 63, 716–719 (2000).CrossRefPubMedGoogle Scholar
  19. Rothberger, C. J. and Winterberg, H., Über die experimentelle Erzeugung extrasystolischer ventriculäirer Tachykardie durch Accelerantreizung (Ein Beitrag zur Herzwirkung von Barium und Calcium). Pflugers Arch. Ges. Physiol., 142, 461–468 (1911).CrossRefGoogle Scholar
  20. Setnikar, I., Magistretti, M. J., and Tirone, P., Cardiovascular and other pharmacologic activities of three betaphenoxyethylamines with local anesthetic activity. Arzneimittelforschung, 16, 1275–1287 (1966).PubMedGoogle Scholar
  21. Takaoka, D., Kawahara, H., Ochi, S., Hiroi, M., Nozaki, H., and Nakayama M., The structures of sesquiterpene glycosides from Pittosporum tobira Ait. Chem. Lett., 7, 1121–1124 (1986).CrossRefGoogle Scholar
  22. Vasange, M., Liu, B. L., Welch, C. J., Rolfsen, W., and Bohlin, L., The flavonoid constituents (Calaguala) and their effect on the elastase release in human neutrophils. Planta Med., 63, 511–517 (1997).CrossRefPubMedGoogle Scholar
  23. Vermes, B., Seligmann, O., and Wagner, H., Synthesis of biologically active tetrahydrofurofuranlignan (syringin, pinoresinol) mono- and bisglucosides. Phytochemistry, 30, 3087–3089 (1991).CrossRefGoogle Scholar
  24. Walker, M. J., Curtis, M. J., Hearse, D. J., Cambell, R. W., Janse, M. J., and Yellon, D. M., The Lambeth Conventions: guidelines for the study of arrhythmias in ischaemia, infarction and reperfusion. Cardiovasc. Res., 22, 447–455 (1988).CrossRefPubMedGoogle Scholar
  25. Wu, G. D., Qian, Z. Q., and Dai, J., Experimental study on antituberculous activities of Pittosporum brevicalyx (Oliv.) Gagnep. J. Chin. Antituberculosis. Assoc., 29, 41–43 (2007).Google Scholar
  26. Xie, T., Liang, J. Y., Liu, J., Wang, M., Wei, X. L., and Yang, C. H., Chemical Study on Artemisia scoparia. J. China Pharm. Univ., 35, 401–403 (2004).Google Scholar
  27. Yamazaki, T., Shimosaka, S., Sasaki, H., Matsumura, T., Tukiyama, T., and Tokiwa, T., (+)-Syringaresinol-di-O-β-D-glucoside, a phenolic compound from Acanthopanax senticosus Harms, suppresses proinflammatory mediators in SW982 human synovial sarcoma cells by inhibiting activating protein-1 and/or nuclear factor-κB activities. Toxicol. In Vitro, 21, 1530–1537 (2007).CrossRefPubMedGoogle Scholar
  28. Yang, H. T., Chen, Y. S., Xie, J. M., and Zhao, S. N., Chemical constituents of Pittosporum brevicalyx (Oliv) Gagnep. Huaxue Xuebao, 44, 946–950 (1986).Google Scholar
  29. Yoshizawa, F., Deyama, T., Takizawa, N., Usmanghani, K., and Ahmad, M., The constituents of Cistanche tubulosa (Schrenk) hook. f. II. Isolation and structures of a new phenylethanoid glycoside and a new neolignan glycoside. Chem. Pharm. Bull., 38, 1927-1930 (1990).Google Scholar
  30. Zhao, D. L., Shen, D. W., Chi, Y. T., Liu, F., Zou, L. B., and Zhu, H. B., Liriodendrin protects SH-SY5Y cells from dopamine-induced cytotoxicity. J. Chin. Pharm. Sci., 16, 294–299 (2007).Google Scholar

Copyright information

© The Pharmaceutical Society of Korea and Springer Netherlands 2010

Authors and Affiliations

  • Chun Feng
    • 1
    • 2
  • Bo-Gang Li
    • 1
  • Xiao-Ping Gao
    • 3
  • Hua-Yi Qi
    • 1
  • Guo-Lin Zhang
    • 1
  1. 1.Chengdu Institute of BiologyChinese Academy of SciencesChengduChina
  2. 2.Graduate School of Chinese Academy of SciencesBeijingChina
  3. 3.Pharmaceutical Institute of Kang Hong Pharmaceutical GroupChengduChina

Personalised recommendations