Planta Med 2009; 75(15): 1597-1601
DOI: 10.1055/s-0029-1185837
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

cis-Clerodane Diterpenoids from the Liverwort Gottschelia schizopleura and their Cytotoxic Activity

Chun-Mei Liu1 , Rui-Liang Zhu2 , Run-Hui Liu1 , Hui-Liang Li1 , Lei Shan1 , Xi-Ke Xu1 , Wei-Dong Zhang1
  • 1Department of Natural Product Chemistry, School of Pharmacy, Second Military Medical University, Shanghai, P. R. China
  • 2School of Life Science, East China Normal University, Shanghai, P. R. China
Further Information

Publication History

received Dec. 30, 2008 revised May 12, 2009

accepted May 28, 2009

Publication Date:
03 July 2009 (online)

Abstract

Two new and three previously known cis-clerodane diterpenoids were isolated from the wild liverwort Gottschelia schizopleura (Jungermanniales, Jungermanniaceae). Their structures were established on the basis of spectroscopic analysis, especially 1D and 2D NMR data. The cytotoxic activities of compounds 15 were evaluated against liver hepatoblastoma (HEP‐G2), lung carcinoma (A549), breast ductal carcinoma (MDA‐MB‐435), and colon adenocarcinoma (LOVO) cell lines. Compound 1 showed moderate inhibition against MDA‐MB‐435 and LOVO cells.

References

  • 1 Asakawa Y. Chemical constituents of the bryophytes. Herz W, Kirby WB, Moore RE, Steglich W, Tamm CH Progress in the chemistry of organic natural products, Vol. 65. Vienna; Springer 1995: 1-618
  • 2 Scher J M, Burgess E J, Lorimer S D, Perry N B. A cytotoxic sesquiterpene and unprecedented sesquiterpenebisbibenzyl compounds from the liverwort Schistochila glaucescens.  Tetrahedron. 2002;  58 7875-7882
  • 3 Asakawa Y. Biologically active substances from bryophytes. Chopra RN, Bhatla SC Bryophytes development: physiology and biochemistry. Boca Raton; CRC Press 1990: 259-287
  • 4 Nagashima F, Suzuki M, Takaoka S, Asakawa Y. Sesqui- and diterpenoids from the Japanese liverwort Jungermannia infusca. .  J Nat Prod. 2001;  64 1309-1317
  • 5 Long D G, Váňa J. The genus Gottschelia Grolle (Jungermanniopsida, Lophoziaceae) in China, with a description of G. grollei, sp. nov.  J Bryology. 2007;  29 165-168
  • 6 Grolle R, Schill D B, Long D G. Notes on Gottschelia (Jungermanniales, Lophoziaceae), with a description of G. patoniae, a new species from the East Himalaya.  J Bryology. 2003;  25 3-6
  • 7 Li Y C, Fung K P, Kwok T T, Lee C Y, Suen Y K, Kong S K. Mitochondrial targeting drug lonidamine triggered apoptosis in doxorubicin-resistant HepG2 cells.  Life Sci. 2002;  72 2729-2740
  • 8 Imamura P M, Costa M. Synthesis of 16,18-dihydroxycleroda-3, 13Z-dien-16,15-olide, (+)-16-hydroxycleroda-3, 13Z-dien-16,15-olide, and (−)-hydroxyhalima-5(10), 13-dien-16,15-olide from (+)-hardwickiic acid.  J Nat Prod. 2000;  63 1623-1625
  • 9 Kernan M R, Faulkner D J. Regioselective oxidation of 3-alkylfurans to 3-alkyl-4-hydroxybutenolides.  J Org Chem. 1988;  53 2773-2776
  • 10 Akhila A, Rani K, Thakur R S. Biosynthesis of the clerodane furano-diterpene lactone skeleton in Tinospora cordifolia.  Phytochemistry. 1991;  30 2573-2576
  • 11 Eguchi T, Dekishima Y, Hamano Y, Dairi T, Seto H, Kakinuma K. A new approach for the investigation of isoprenoid biosynthesis featuring pathway switching, deuterium hyperlabeling, and H NMR spectroscopy. The reaction mechanism of a novel Streptomyces diterpene cyclase.  J Org Chem. 2003;  68 5433-5438
  • 12 Anderson A B, McCrindle R, Nakamura E. Diterpenoids of Solidago Arguta Ait. The stereochemistry of cis-clerodanes.  Chem Commun. 1974;  453-454
  • 13 McCrindle R, Nakamura E, Anderson A B. Constituents of SoWago species. Part VII. Constitution and stereochemistry of the cis-clerodanes from Solidago arguta Ait. and of related diterpenoids.  J Chem Soc [Perkin I]. 1976;  1590-1597
  • 14 Billet D, Durgeat M, Heitz S, Brouard J P, Ahond A. Constituants d'Evodia floribunda Baker. II – 1ère Partie. L'acide floridiolique, nouveau diterpene de type clerodane.  Tetrahedron Lett. 1976;  2773-2776
  • 15 Zdero C, Bohlmann F, King R M. Diterpenes and norditerpenes from the Aristeguetia group.  Phytochemistry. 1991;  30 2991-3000
  • 16 Geis W, Buschauer B, Becker H. cis-Clerodandes from axenic cultures of the liverwort Scapania nemorea.  Phytochemistry. 1999;  51 643-649
  • 17 Chaichantipyuth C, Petsom A, Taweechotipatr P, Muangsin N, Chaichit N, Puthong S, Roengsumran S, Kawahata M, Watanabe T, Ishikawa T. New labdane-type diterpenoids from Croton oblongifolius and their cytotoxic activity.  Heterocycles. 2005;  65 809-822

Prof. Wei-Dong Zhang

Department of Natural Product Chemistry
School of Pharmacy
Second Military Medical University

325 Guohe Road

Shanghai 200433

People's Republic of China

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