Planta Med 2007; 73(6): 567-571
DOI: 10.1055/s-2007-967195
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Novel Epoxyfuranoid Lignans and Antitubercular Constituents from the Leaves of Beilschmiedia tsangii

Jih-Jung Chen1 , En-Tzu Chou1 , Chien-Fang Peng2 , Ih-Sheng Chen3 , Sheng-Zehn Yang4 , Hung-Yi Huang3
  • 1Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung, Taiwan
  • 2Faculty of Biomedical Laboratory Sciences, College of Health Science, Kaohsiung Medical University, Kaohsiung, Taiwan
  • 3Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan
  • 4Department of Forest Resource, Management and Technology, National Pingtung University of Science and Technology, Pingtung, Taiwan
Weitere Informationen

Publikationsverlauf

Received: January 4, 2007 Revised: March 25, 2007

Accepted: April 10, 2007

Publikationsdatum:
22. Mai 2007 (online)

Abstract

Three new epoxyfuranoid lignans, 4α,5α-epoxybeilschmin A (1), 4α,5α-epoxybeilschmin B (2), and beilschmin D (3), together with nine known compounds have been isolated from the leaves of Beilschmiedia tsangii. The structures of these new compounds were determined through spectral analyses. Among the isolates, beilschmin A (4) and beilschmin B (5) exhibited potent antitubercular activities (MICs = 2.5 and 7.5 μg/mL, respectively) against Mycobacterium tuberculosis 90 - 221 387 in vitro.

References

  • 1 Liao J C. Lauraceae in Flora of Taiwan, Vol. 2, 2nd edition. Taipei; Editorial Committee of the Flora of Taiwan 1996: 433-7.
  • 2 Chen J J, Chou E T, Duh C Y, Yang S Z, Chen I S. New cytotoxic tetrahydrofuran- and dihydrofuran-type lignans from the stem of Beilschmiedia tsangii .  Planta Med. 2006;  72 351-7.
  • 3 Clezy P S, Nichol A W, Gellert E. The structures of laurelliptine, a new aporphine alkaloid, and thalicmidine.  Experientia. 1963;  19 1-2.
  • 4 Kitagawa I, Minagawa K, Zhang R S, Hori K, Doi M, Inoue M. et al . Dehatrine, an antimalarial bisbenzylisoquinoline alkaloid from the Indonesian medicinal plant beilschmiedia madang, isolated as a mixture of two rotational isomers.  Chem Pharm Bull. 1993;  41 997-9.
  • 5 Banfield J E, Black D SC, Collins D J, Hyland B PM, Lee J J, Pranowo S R. Constituents of some species of Beilschmiedia and Endiandra (Lauraceae): New endiandric acid and benzopyran derivatives isolated from B. oligandra .  Aust J Chem. 1994;  47 587-607.
  • 6 Inderlied C B, Nash K A. Antibiotics in laboratory medicine, 4th edition. Baltimore; Williams & Wilkins 1996: 127-75.
  • 7 Tofern B, Jenett-Siems K, Siems K, Jakupovic J, Eich E. Bonaspectins and neobonaspectins, first sesquilignans and sesquineolignans from a convolvulaceous species.  Phytochemistry. 2000;  53 119-28.
  • 8 Chen J J, Lin R W, Duh C Y, Huang H Y, Chen I S. Flavones and cytotoxic constituents from the stem bark of Muntingia calabura .  J Chin Chem Soc. 2004;  51 665-70.
  • 9 Chen J J, Peng C F, Huang H Y, Chen I S. Benzopyrans, biphenyls and xanthones from the root of Garcinia linii and their activity against Mycobacterium tuberculosis .  Planta Med. 2006;  72 473-7.
  • 10 Chen J J, Duh C Y, Chen I S. Cytotoxic chromenes from Myriactis humilis .  Planta Med. 2005;  71 370-2.
  • 11 Skinner W A, Alaupovic P. Oxidation products of vitamin E and its model, 6-hydroxy-2,2,5,7,8-pentamethylchroman. V. Studies of the products of alkaline ferricyanide oxidation.  J Org Chem. 1963;  28 2854-8.
  • 12 Purcell J M, Morris S G, Susi H. Proton magnetic resonance spectra of unsaturated fatty acids.  Anal Chem. 1966;  38 588-92.

Dr. J. J. Chen

Graduate Institute of Pharmaceutical Technology

Tajen University

Pingtung 907

Taiwan

Fax: +886-8-762-5308

eMail: jjchen@mail.tajen.edu.tw

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