Planta Med 2006; 72(8): 767-770
DOI: 10.1055/s-2006-941505
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic Phenanthrenes from the Rhizomes of Tamus communis

Borbála Réthy1 , Adriána Kovács2 , István Zupkó1 , Peter Forgo3 , Andrea Vasas2 , György Falkay1 , Judit Hohmann2
  • 1Department of Pharmacodynamics and Biopharmacy, University of Szeged, Szeged, Hungary
  • 2Department of Pharmacognosy, University of Szeged, Szeged, Hungary
  • 3Department of Organic Chemistry, University of Szeged, Szeged, Hungary
This work is dedicated to Professor Kálmán Szendrei on the occasion of his 70th birthday
Further Information

Publication History

Received: January 6, 2006

Accepted: April 16, 2006

Publication Date:
19 June 2006 (online)

Abstract

From the fresh rhizomes of Tamus communis five phenanthrenes (1 - 5) were isolated under the guidance of cytotoxic assays in HeLa cells. The compounds were obtained from the highly active CHCl3 fraction of the MeOH extract by using multistep chromatographic purifications, including VLC, preparative TLC, HPLC and gel filtration. The compounds were identified by means of EI-mass, UV and NMR spectroscopy as 7-hydroxy-2,3,4-trimethoxyphenanthrene (1), 2,7-dihydroxy-3,4-dimethoxyphenanthrene (nudol) (2), 2,7-dihydroxy-3,4,8-trimethoxyphenanthrene (3), 3,7-dihydroxy-2,4,8-trimethoxyphenanthrene (confusarin) (4), and 3,7-dihydroxy-2,4-dimethoxyphenanthrene (5). Compound 1 is a new natural product, and 2 - 4 were isolated for the first time from T. communis. In the cytotoxic assays, compounds 1 - 3 and 5 significantly inhibited the growth of HeLa cells (IC50 = 0.97 - 20.18 μM). Compound 3, with an IC50 value of 0.97 μM, is of special interest because of its high activity.

References

  • 1 Cirla A, Mann J. Combretastatins: from natural products to drug discovery.  Nat Prod Rep. 2003;  20 558-64
  • 2 Reisch J, Báthory M, Szendrei K, Novák I, Minker E. Weitere Phenanthrene aus dem Rhizom von Tamus communis .  Phytochemistry. 1973;  12 228-9
  • 3 Reisch J, Báthory M, Novák I, Szendrei K. Természetes fenantrén vegyületek szerkezete és szintézise.  Herba Hung. 1970;  9 43-8
  • 4 Reisch J, Báthory M, Novák I, Szendrei K, Minker E. Stickstofffreie Phenathren-Derivate als Pflanzeninhaltsstoffe.  Herba Hung. 1972;  11 61-71
  • 5 Aquino R, Behar I, De Simone F, Pizza C, Senatore F. Phenanthrene derivatives from Tamus communis .  Biochem Syst Ecol. 1985;  13 251-2
  • 6 Aquino R, Behar I, De Simone F, Pizza C. Natural dihydrophenanthrene derivatives from Tamus communis .  J Nat Prod. 1985;  48 811-3
  • 7 Tuchinda P, Udchachon J, Khumtaveeporn K, Taylor W C, Engelhardt L M, White A H. Phenanthrenes of Eulophia nuda .  Phytochemistry. 1988;  27 3267-71
  • 8 Leong Y W, Harrison L J, Powell A D. Phenanthrene and other aromatic constituents of Bulbophyllum vaginatum .  Phytochemistry. 1999;  50 1237-41
  • 9 Bhandari S R, Kapadi A H, Mujumder P L, Joardar M, Shoolery J N. Nudol, a phenanthrene of the orchids Eulophia nuda, Eria carinata and Eria stricta .  Phytochemistry. 1985;  24 801-4
  • 10 Leong Y W, Kang C C, Harrison L J, Powell A D. Phenanthrenes, dihydrophenanthrenes and bibenzyls from the orchid Bulbophyllum vaginatum .  Phytochemistry. 1997;  44 157-65
  • 11 Majumder P L, Kar A. Confusarin and confusaridin, two phenanthrene derivatives of the orchid Eria confusa .  Phytochemistry. 1987;  26 1127-9
  • 12 Majumder P L, Pal S, Majumder S. Dimeric phenanthrenes from the orchid Bulbophyllum reptans .  Phytochemistry. 1999;  50 891-7
  • 13 Estrada S, Rojas A, Mathison Y, Israel A, Mata R. Nitric oxide cGMP mediates the spasmolytic action of 3,4′-dihydroxy-5,5′-dimethoxybibenzyl from Scaphyglottis livida .  Planta Med. 1999;  65 109-14
  • 14 Letcher R M, Wong K M. Structure and synthesis of the phenanthrenes TaIV and TaVIII from Tamus communis . J Chem Soc Perkin Trans 1 1979: 2449-50
  • 15 Lin C M, Singh S B, Chu P S, Dempcy R O, Schmidt J M, Pettit G R. et al . Interactions of tubulin with potent natural and synthetic analogs of the antimitotic agent combretastatin - a structure-activity study.  Mol Pharmacol. 1988;  34 200-8
  • 16 Cushman M, Nagarathnam D, Gopal D, He H M, Lin C M, Hamel E. Synthesis and evaluation of analogs of (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene as potential cytotoxic and antimitotic agents.  J Med Chem. 1992;  35 2293-306
  • 17 Srivastava V, Negi A S, Kumar J K, Gupta M M, Khanuja S PS. Plant-based anticancer molecules: a chemical and biological profile of some important leads.  Bioorg Med Chem. 2005;  13 5892-908
  • 18 Gwaltney SL I I, Imade H M, Barr K J, Li Q, Gehrke L, Credo R B. et al . Novel sulfonate analogues of combretastatin A-4: potent antimitotic agents.  Bioorg Med Chem Lett. 2001;  11 871-4
  • 19 Sun L, Vasilevich N I, Fuselier J A, Hocart S J, Coy D H. Examination of the 1,4-disubstituted azetidinone ring system as a template for combretastatin A-4 conformationally restricted analogue design.  Bioorg Med Chem Lett. 2004;  14 2041-6
  • 20 Pettit G R, Singh S B, Niven M L, Schmidt J M. Cell-growth inhibitory dihydrophenanthrene and phenanthrene constituents of the African tree Combretum caffrum .  Can J Chem. 1988;  66 406-13

Prof. Dr. Judit Hohmann

Department of Pharmacognosy

University of Szeged

Eötvös u. 6

6720 Szeged

Hungary

Phone: +36-62-546-453

Fax: +36-62-545-704

Email: hohmann@pharma.szote.u-szeged.hu