Planta Med 2001; 67(9): 847-852
DOI: 10.1055/s-2001-18847
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

Cytotoxic Mono-Tetrahydrofuran Ring Acetogenins from Leaves of Annona montana

Li-Quan Wang1, 2 , Yan Li1 , Byung-Sun Min1 , Norio Nakamura1 , Guo-Wei Qin2 , Can-Jun Li2 , Masao Hattori1
  • 1 Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Toyama, Japan
  • 2 Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai, China
Further Information

Publication History

November 30, 2000

March 21, 2001

Publication Date:
06 December 2001 (online)

Abstract

Further studies on leaves of Annona montana led to isolation of one iso-acetogenin, montanacin G, three pairs of acetogenins, montanacin H-J and 34-epi-montanacin H-J, together with four known acetogenins, gigantetrocins A and B, annonacin and cis-annonacin. Montanacin G belongs to the iso-acetogenin group with a terminal 2,4-trans-ketolactone unit. Montanacin H-J and 34-epi-montanacin H-J contain the rare γ-hydroxy-γ-methyl-γ-lactone moiety. The cytotoxic activities of these compounds, together with previously reported acetogenins, montanacins B and C, were examined against Meth-A and LLC tumor cell lines in vitro.

References

  • 1 Alali F Q, Liu X X, McLaughlin J L. Annonaceous acetogenins: Recent progress.  Journal of Natural Products. 1999;  62 504-40
  • 2 Mootoo B S, Ali A, Khan A, Reynolds W F, McLean S. Three novel monotetrahydrofuran Annonaceous acetogenins from Annona montana .  Journal of Natural Products. 2000;  63 807-11
  • 3 Jossang A, Dubaele B, Cavé A, Bartoli M H, Beriel H. Deux nouvelles acétogénines monotétrahydrofuraniques cytotoxiques: l’annomonicine et la montanacin.  Tetrahedron Letters. 1990;  13 1861-4
  • 4 Jossang A, Dubaele B, Cavé A, Bartoli M H, Beriel H. Annomontacine: une nouvella acétogénine γ-lactone-monotétrahydrofuranique cytotoxique de l’Annona montana .  Journal of Natural Products. 1991;  54 967-71
  • 5 Wu Y C, Chang F R, Chen K S, Liang S C, Lee M R. Diepoxymontin, a novel acetogenin from Annona montana .  Heterocycles. 1994;  38 1475-8
  • 6 Wang L Q, Nakamura N, Meselhy M R, Hattori M, Zhao W M, Cheng K F. et al . Four mono-tetrahydrofuran ring acetogenins, Monatancins B-E, from leaves of Annona montana .  Chemical and Pharmaceutical Bulletin. 2000;  48 1109-13
  • 7 Geran R I, Greenberg N H, McDonald M M, Schumacher A M, Abbott B J. Protocols for screening chemical agents and natural products against animal tumors and other biological systems.  Cancer Chemotherapy Reports (part 3). 1972;  3 (2) 1-103
  • 8 Skehan P, Streng R, Scudiero D, Monks A, McMahon J, Vistica D ,. et al . New cdorimetric cytotoxicity assay for anticancer-drug screening.  Journal of National Cancer Institute. 1990;  82 1107-13
  • 9 Min B S, Ahn B Z, Bae K H. Synthesis and structure-activity relationship of cytotoxic 5,2′,5′-trihydroxy-7,8-dimethoxyflavonone analogues.  Archives of Pharmacal Research. 1996;  19 543-50
  • 10 Zeng L, Ye Q, Oberlies N, Shi G, Gu Z M, He K. et al . Recent adcances in Annonaceous acetogenins.  Natural Products Reports. 1996;  13 275-306
  • 11 Alali F Q, Zhang Y, Rogers L, McLaughlin J L. Mono-tetrahydrofuran acetogenins from Goniothalamus giganteus .  Phytochemistry. 1998;  49 761-8
  • 12 Zhao G X, Rieser M J, Hui Y .H, Miesbauer L R, Smith D L, McLaughlin J L. Biologically active acetogenins from stem bark of Asimina triloba .  Phytochemistry. 1993;  33 1065-73
  • 13 Hopp D C, Alali F Q, Gu Z M, McLaughlin J L. Mono-THF ring Annonaceous acetogenins from Annona squamosa .  Phytochemistry,. 1998;  47 803-9
  • 14 Scholz G, Tochtermann W. Optisch aktive γ-Lactone aus Cyclooctin und Furan-Synthese von (-)-Muricatacin.  Tetrahedron Letters. 1991;  32 5535-8
  • 15 Duret P, Laurens A, Hocquemiller R, Cortes D, Cavé A. Isoacetogenins, artifacts issued from translactonization from Annonaceous acetogenins.  Heterocycles,. 1994;  39 741-9
  • 16 Jiang Z, Yu D Q. New types of mono-tetrahydrofuran ring acetogenins from Goniothalamus donnaiensis .  Journal of Natural Products. 1997;  60 122-5
  • 17 Chen Y, Chen R R, Jiang Z, Yu D Q. A new epimeric pair of mono-THF Annonaceous acetogenins from Goniothalamus gardneri .  Planta Medica. 1998;  64 242-5
  • 18 Jiang Z, Chen R Y, Chen Y, Yu D Q. Two epimeric pairs of C-4-acetyl Annonaceous acetogenins from Goniothalamus donnaiensis .  Planta Medica. 1998;  64 362-6
  • 19 Zeng L, Wu F E, McLaughlin J L. Annohexocin, a novel mono-THF acetogenins with six hydroxyls, from Annona muricata (Annonaceae).  Bioorganic Medicinal Chemistry Letters. 1995;  5 1865-8
  • 20 Fujimoto Y, Murasaki C, Shimada H, Nishioka S, Kakinuma K, Singh S ,. et al . Annonaceous acetogneins from the seeds of Annona squamosa. Non-adjacent bis-tetrahydrofuranic acetogenins.  Chemical and Pharmaceutical Bulletin. 1994;  42 1175-84
  • 21 Liu X X, Alali F Q, Pilarinou E, McLaughlin J L. Two bioactive mono-tetrahydrofuran acetogenins, annoglacins A and B, from Annona glabra .  Phytochemistry. 1999;  50 815-21
  • 22 Liu X X, Alali F Q, Pilarinou E, McLaughlin J L. Glacins A and B : Two novel bioactive mono-tetrahydrofuran acetogenins from Annona glabra .  Journal of Natural Products. 1998;  61 620-4

Prof. Guo-Wei Qin

Shanghai Institute of Materia Medica

Chinese Academy of Sciences

294 Tai-Yuan Road

Shanghai 200031

People’s republic of China

Email: gwqin@mail.shcnc.ac.cn

Fax: +86-21-64370269

Prof. Masao Hattori

Institute of Natural Medicine

Toyama Medical and Pharmaceutical University

2630 Sugitani

Toyama 930-0194

Japan

Email: Saibo421@ms.toyama-mpu.ac.jp

Fax: +81-76-4345060

    >