New Cytotoxic Tetrahydrofuran- and Dihydrofuran-Type Lignans from the Stem of Beilschmiedia tsangii

Abstract

Five new compounds including two tetrahydrofuran-type lignans, beilschmin A and beilschmin B, a dihydrofuran-type lignan, beilschmin C, and two 1-phenylbutyl benzoates, tsangin A and tsangin B, together with thirteen known compounds have been isolated from the stem of Beilschmiedia tsangii. The structures of these new compounds were determined through spectral analyses. Among the isolates, beilschmin A (1), beilschmin B (2), beilschmin C (3), tsangin A (4), tsangin B (5), 2,6,11-trimethyldodeca-2,6,10-triene (14), α-tocopherylquinone (17), and α-tocospiro B (18) were cytotoxic (IC₅₀ values < 4 μg/mL) in P-388 and/or HT-29 cell lines in vitro.

Key words

Beilschmiedia tsangii - Lauraceae - tetrahydrofuran-type lignans - beilschmin A - beilschmin B - dihydrofuran-type lignan - beilschmin C - 1-phenylbutyl benzoates - tsangin A - tsangin B - cytotoxicity

References

• 1 Liao J C. Lauraceae in Flora of Taiwan. 2nd edn Taipei; Editorial Committee of the Flora of Taiwan 1996 Vol 2: pp 433-7
• 2 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
• 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 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.  J Immunol Meth. 1983;  65 55-63
• 6 Hada S, Hattori M, Tezuka Y, Kikuchi T, Namba T. New neolignans and lignans from the aril of Myristica fragrans .  Phytochemistry. 1988;  27 563-8
• 7 Martins R CC, Latorre L R, Sartorelli P, Kato M J. Phenylpropanoids and tetrahydrofuran lignans from Piper solmsianum .  Phytochemistry. 2000;  55 843-6
• 8 Prasad A K, Tyagi O D, Wengel J, Boll P M, Olsen C E, Bisht K S. et al . Neolignans and a lignan from Piper clarkii .  Phytochemistry. 1995;  39 655-8
• 9 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
• 10 Chen J J, Huang Y C, Chen Y C, Huang Y T, Wang S W, Peng C Y. et al . Cytotoxic amides from Piper sintenense .  Planta Med. 2002;  68 980-5
• 11 Chen J J, Chang Y L, Teng C M, Chen I S. Anti-platelet aggregation alkaloids and lignans from Hernandia nymphaeifolia .  Planta Med. 2000;  66 251-6
• 12 Chen J J, Huang H Y, Duh C Y, Chen I S. Cytotoxic constituents from the stem bark of Zanthoxylum pistaciiflorum .  J Chin Chem Soc. 2004;  51 659-63
• 13 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
• 14 Kobayashi M, Krishna M M, Ishida K, Anjaneyulu V. Marine sterols. XXII. Occurrence of 3-oxo-4,6,8(14)-triunsaturated steroids in the sponge Dysidea herbacea .  Chem Pharm Bull. 1992;  40 72-4
• 15 Mahmood U, Kaul V K, Singh B. Sesquiterpene and long chain ester from Tanacetum longifolium .  Phytochemistry. 2002;  61 913-7
• 16 Chen J J, Duh C Y, Chen I S. Cytotoxic chromenes from Myriactis humilis .  Planta Med. 2005;  71 370-2
• 17 Fujimoto H, Satoh Y, Yamazaki M. Four new immunosuppressive components, kobiin and kobifuranones A, B, and C, from an ascomycete, Gelasinospora kobi .  Chem Pharm Bull. 1998;  46 211-6
• 18 Chiang Y M, Kuo Y H. Two novel α-tocopheroids from the aerial roots of Ficus microcarpa .  Tetrahedron Lett. 2003;  44 5125-8