Skip to main content
Log in

A new triterpene and an antiarrhythmic liriodendrin from Pittosporum brevicalyx

  • Research Articles
  • Drug Discovery and Development
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Aurada, E., Jurenitsch, J., and Kubelka, W., Structure of triterpene sapogenins of Aesculus glabra. Planta Med., 50, 391–394 (1984).

    Article  CAS  PubMed  Google Scholar 

  • Bergeron, C., Marston, A., Antus, S., Gauthier, R., and Hostettmann, K., Flavonoids from Pyrola elliptica. Phytochemistry, 49, 233–236 (1998).

    Article  CAS  Google Scholar 

  • Cheung, B. M. and Kumana, C. R., Calcium channel blockers revisited. Hong Kong Med. J., 8, 300–301 (2002).

    CAS  PubMed  Google Scholar 

  • 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).

    Article  CAS  PubMed  Google Scholar 

  • 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).

    Article  Google Scholar 

  • Deyama, T., Nishibe, S., and Nakazawa, Y., Constituents and pharmacological effects of Eucommia and Siberian ginseng. Acta Pharmacol. Sin., 22, 1057–1070 (2001).

    CAS  PubMed  Google Scholar 

  • 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).

    Article  Google Scholar 

  • 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).

  • 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).

    Article  CAS  Google Scholar 

  • 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).

    Article  CAS  PubMed  Google Scholar 

  • 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 

  • 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 

  • 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).

    CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • 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).

    Article  CAS  PubMed  Google Scholar 

  • Kosuge, K., Mitsunaga, K., Koike, K., and Ohmoto, T., Studies on the constituents of Ailanthus integrifolia. Chem. Pharm. Bull., 42, 1669–1671 (1994).

    CAS  PubMed  Google Scholar 

  • 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).

    CAS  PubMed  Google Scholar 

  • 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).

    Article  CAS  PubMed  Google Scholar 

  • 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).

    Article  Google Scholar 

  • 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).

    CAS  PubMed  Google Scholar 

  • 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).

    Article  Google Scholar 

  • 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).

    Article  CAS  PubMed  Google Scholar 

  • Vermes, B., Seligmann, O., and Wagner, H., Synthesis of biologically active tetrahydrofurofuranlignan (syringin, pinoresinol) mono- and bisglucosides. Phytochemistry, 30, 3087–3089 (1991).

    Article  CAS  Google Scholar 

  • 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).

    Article  CAS  PubMed  Google Scholar 

  • 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 

  • 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).

    CAS  Google Scholar 

  • 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).

    Article  CAS  PubMed  Google Scholar 

  • 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).

    CAS  Google Scholar 

  • 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 

  • 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).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Guo-Lin Zhang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Feng, C., Li, BG., Gao, XP. et al. A new triterpene and an antiarrhythmic liriodendrin from Pittosporum brevicalyx . Arch. Pharm. Res. 33, 1927–1932 (2010). https://doi.org/10.1007/s12272-010-1206-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12272-010-1206-1

Key words

Navigation