Planta Medica, Table of Contents Planta Med 2007; 73(6): 567-571DOI: 10.1055/s-2007-967195 Natural Product ChemistryOriginal Paper© Georg Thieme Verlag KG Stuttgart · New YorkNovel 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 Recommend Article Abstract Buy Article(opens in new window) 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. Key words Beilschmiedia tsangii - Lauraceae - epoxyfuranoid lignans - 4α,5α-epoxybeilschmin A - 4α,5α-epoxybeilschmin B - beilschmin D - antitubercular activity Full Text References 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 Supplementary Material Supplementary Material www.thieme-connect.de/ejournals/toc/plantamedica
