Download PDF
Planta Med 2006; 72(2): 169-174
DOI: 10.1055/s-2005-873199
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

New Lignans and Cytotoxic Constituents from Schisandra propinqua

Li-Jia Xu1 , 2 , Feng Huang1 , Si-Bao Chen1 , 2 , 3 , Qiao-Xia Zhang2 , 3 , Liang-Niang Li4 , Shi-Lin Chen1 , 2 , 3 , Pei-Gen Xiao1
  • 1Institute of Medicinal Plant Development, Peking Union Medical College & Chinese Academy of Medical Sciences, Beijing, P. R. China
  • 2State Key Laboratory of Chinese Medicine and Molecular Pharmacology, Shenzhen, P. R. China
  • 3Department of Applied Biology & Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Hong Kong
  • 4Institute of Materia Medica, Peking Union Medical College & Chinese Academy of Medical Sciences, Beijing, P. R. China
Further Information

Publication History

Received: April 5, 2005

Accepted: July 13, 2005

Publication Date:
08 December 2005 (online)

    Permissions and Reprints

Abstract

The CHCl3 extract from the stems of Schisandra propinqua (Wall.) Baill exhibited significant cytotoxic activity against cancer cell lines. Subsequent fractionation procedures led to the isolation of four new dibenzocyclooctadiene lignans, propinquanins A - D, along with two known lignans, schisantherin I and heteroclitin A, and three known triterpenoids, isoschisandrolic acid, schisandrolic acid and schisandronic acid. Their structures, including absolute stereochemistry, were elucidated through analyses of NMR data and CD spectra. The isolated compounds were tested for their cytotoxic activity in several tumor cell lines with the MTT assay. Propinquanin B (2) was significantly cytotoxic (IC50 values < 10μM) in HL-60 and Hep-G2 tumor cell lines. Cell cycle analysis and Hoechst 33 258 staining assay suggested that one possible mechanism of cytotoxic activity by 2 might be related to the induction of apoptosis.

Key words

Schisandra propinqua (Wall.) Baill - Schisandraceae - dibenzocyclooctadiene - lignans - triterpenoids - cytotoxictity

References

  • 1 Chen Y G, Qin G W, Xie Y Y. Dibenzocyclooctadiene lignans from Schisandra propinqua .  Chem J Chin Univ. 2001;  22 1518-20
    PubMedGoogle Scholar
  • 2 Chen Y G, Qin G W, Xie Y Y. Lignans from Schisandra propinqua (Wall.) Hook. f. et Thoms.  Chin J Chin Mater Med. 2001;  24 105-7
    PubMedGoogle Scholar
  • 3 Chen Y G, Qin G W, Xie Y Y. Studies on chemical constituents of Schisandra propinqua (Wall.) Hook. f. et Thoms.  Chin J Chin Mater Med. 2001;  26 694-7
    PubMedGoogle Scholar
  • 4 Li Z Y, Li L, Zhang H B. Studies on the chemical constituents of Zhongjian wuweizi .  Chin Tradit Herb Drugs. 1996;  27 3-4
    PubMedGoogle Scholar
  • 5 Liu J S, Ma Y T, Huang M F. Studies on the constituents of Schisandraceae plants in Shennongjia District. I. Constituents of Schisandra propinqua Hook. F. et Thoms. var. sinensis Oliv.  Acta Chim Sin. 1988;  46 345-8
    PubMedGoogle Scholar
  • 6 Chen Y G, Qin G W, Xie Y Y. A novel triterpenoid lactone, schiprolactone A, from Schisandra propinqua (Wall.) Hook. f. et Thoms.  Chem J Chin Univ. 2001;  19 304-7
    PubMedGoogle Scholar
  • 7 Chen Y G, Qin G W, Cao L, Leng Y, Xie Y Y. Triterpenoid acids from Schisandra propinqua with cytotoxic effect on rat luteal cells and human decidual cells in vitro .  Fitoterapia. 2001;  72 435-7
    CrossrefPubMedGoogle Scholar
  • 8 Liu J S, Huang M F, Tao Y. Anwuweizonic acid and manwuweizic acid, the putative anticancer active principle of Schisandra propinqua .  Can J Chem. 1988;  66 414-5
    CrossrefPubMedGoogle Scholar
  • 9 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.  J Immunol Methods. 1983;  65 55-63
    CrossrefPubMedGoogle Scholar
  • 10 Liu J S, Ma Y T. Studies on the constituents of Schisandraceae plants in Shennongjia District.III. Isolation and structures of schisantherin G, H and I.  Acta Chim Sin. 1988;  46 465-71
    PubMedGoogle Scholar
  • 11 Chen D F, Xu G J, Yang X W, Hattori M, Tezuka Y, Kikuchi T. et al . Dibenzocyclo-octadiene lignans from Kadsura heteroclita .  Phytochemistry. 1992;  31 629-32
    CrossrefPubMedGoogle Scholar
  • 12 Sy L K, Richard M K, Brown G D. Phytochemistry of Illicium dunnianum and the systematic position of the Illiciaceae.  Phytochemistry. 1997;  44 1099-108
    CrossrefPubMedGoogle Scholar
  • 13 Kotaro T, Masako T. Studies on constituents of medicinal plants. XIV. Constituents of Schizandra nigra Max.  Chem Pharm Bull. 1975;  23 537-42
    PubMedGoogle Scholar
  • 14 Chen D F, Zhang S X, Chen K, Zhou B N, Wang P, Cosentino L M. et al . Two new lignans, interiotherins A and B, as anti-HIV principles from Kadsura interior .  J Nat Prod. 1996;  59 1066-8
    CrossrefPubMedGoogle Scholar
  • 15 Chen Y G, Wang P, Lin Z W, Sun H D, Qin G W, Xie Y Y. Dibenzocyclooctadiene lignans from Kadsura angustifolia .  Phytochemistry. 1998;  48 1059-62
    CrossrefPubMedGoogle Scholar
  • 16 Liu J S, Ma Y T. Constituents of Schisandraceae plants in Shennongjia District. II. Isolation and structure of schisantherin F.  Acta Chim Sin. 1988;  46 460-4
    PubMedGoogle Scholar
  • 17 Kuo Y H, Li S Y, Huang R L, Wu M D, Huang H C, Lee K H. Schizarin B, C, D and E, four new lignans from Kadsura matsudai and their antihepatitis activities.  J Nat Prod. 2001;  64 487-90
    CrossrefPubMedGoogle Scholar
  • 18 Ikeya Y, Taguchi H, Yosioka H. The constituents of Schizandra chinensis Baill. I. Isolation and structure determination of five new lignans, gomisin A, B, C, F and G, and the absolute structure of schizandrin.  Chem Pharm Bull. 1979;  27 1383-94
    CrossrefPubMedGoogle Scholar

Prof. Shi-Lin Chen

Department of Applied Biology & Chemical Technology

The Hong Kong Polytechnic University

Hung Hom

Hong Kong

People’s Republic of China

Email: bcslchen@inet.polyu.edu.hk

    www.thieme-connect.de/ejournals/toc/plantamedica
>