Planta Medica, Table of Contents Planta Med 2010; 76(6): 613-619DOI: 10.1055/s-0029-1240634 Natural Product Chemistry Original Papers © Georg Thieme Verlag KG Stuttgart · New York Cytotoxic Lignan Esters from Cinnamomum osmophloeum Tai-Hung Chen1 , Yu-Hao Huang1 , Jhih-Jhang Lin1 , Bing-Chung Liau1 , Sheng-Yang Wang2 , Yang-Chang Wu3 , Ting-Ting Jong1* 1Department of Chemistry, National Chung-Hsing University, Taichung, Taiwan 2Department of Forestry, National Chung-Hsing University, Taichung, Taiwan 3Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan Recommend Article Abstract Buy Article Abstract The bark and roots of Cinnamomum osmophloeum are widely used in Taiwan as spice substitutes for C. cassia. We have isolated three novel lignan esters, one dibenzylbutane-type ligan ester [9,9′-di-O-feruloyl-(+)-5,5′-dimethoxy secoisolariciresinol (3)] and two cyclolignan esters [(7′S,8′R,8R) ‐lyoniresinol-9-O-(E)-feruloyl ester (5) and (7′S,8′R,8R)-lyoniresinol-9,9′-di-O-(E)‐feruloyl ester (6)], and several known lignans from the heartwood and roots of C. osmophloeum. We identified these compounds using 1D and 2D NMR spectroscopy and mass spectrometry. Cytotoxicity assays of these novel lignan esters revealed that compound 6 has strong activities against human liver cancer (HepG2 and Hep3B) and oral cancer (Ca9-22) cells, with IC50 values of 7.87, 4.31, and 2.51 µg/mL, respectively. Key words Cinnamomum osmophloeum - Lauraceae - 9,9′‐di‐O‐feruloyl‐(+)‐5,5′‐dimethoxy secoisolariciresinol - (7′S,8′R,8R)‐lyoniresinol‐9‐O‐(E)‐feruloyl ester - (7′S,8′R,8R)‐lyoniresinol‐9,9′‐di‐O‐(E)‐feruloyl ester Full Text References References 1 Lin Z P. The specific topic publication of Cinnamomum osmophloeum. Taipei; Taiwan Forestry Research Institute 1992 2 Liu J Y. Antibacterial, antifungal, mosquito larvicidal and antimite activities of leaf essential oils from six chemotypes of Cinnamomum osmophloeum [dissertation]. Taipei; National Taiwan University 2005 3 Chan S T, Chen P F, Chang S C. Antibacterial activity of leaf essential oils and their constituents from Cinnamomum osmophloeum. J. Ethnopharmacol. 2001; 77 123-127 4 Chang S T, Cheng S S. Antitermitic activity of leaf essential oils and components from Cinnamomum osmophloeum. J Agric Food Chem. 2002; 50 1389-1392 5 Chen P F, Chan S T, Wu H H. Application of leaf essential oils and their constituents from Cinnamomum osmophloeum on the manufacture of antimite paper. Q J Chin Forest. 2002; 35 397-403 6 Fang S H, Rao Y K, Tzeng Y M. Inhibitory effects of flavonol glycosides from Cinnamomum osmophloeum on inflammatory mediators in LPS/IFN-γ-activated murine macrophages. Bioorg Med Chem. 2005; 13 2381-2388 7 Alley M C, Scudiero D A, Monks A, Hursey M L, Ciezerwinski M J, Fine D L. Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay. Cancer Res. 1988; 48 589-601 8 Achenbach H, Waibel R, Aeldae-Mensah I. Lignans and other constituents from Carissa edulis. Phytochemistry. 1983; 22 749-753 9 Inoshiri S, Sasaki M, Kohda H, Ohtsuka H, Yamasaki K. Aromatic glycosides from Berchemia racemosa. Phytochemistry. 1987; 26 2811-2814 10 Fuchino H, Satoh T, Tanaka N. Chemical evaluation of Betula species in Japan. I. Constituents of Betula ermanii. Chem Pharm Bull. 1995; 43 1937-1942 11 Hanawa F, Shiro M, Hayashi Y. Heartwood constituents of Betula maximowicziana. Phytochemistry. 1997; 45 589-595 12 Miyamura M, Nohara T, Tomimatsu T, Nishioka I. Seven aromatic compounds from bark of Cinnamomum cassia. Phytochemistry. 1983; 22 215-218 13 Ahmed A A, Mahmoud A A, Ali E T, Tzakou O, Couladis M, Mabry T J, Gati T, Toth G. Two highly oxygenated eudesmanes and 10 lignans from Achillea holosericea. Phytochemistry. 2002; 59 851-856 14 Lee C K, Chang M H. The chemical constituents from the heartwood of Eucalyptus citriodora. J Chin Chem Soc. 2000; 47 555-560 15 Lo W L, Wu Y C, Heieh T J, Kuo S H, Lin H C, Chen C Y. Chemical constituents from the stems of Michelia compressa. Chin Pharm J. 2004; 56 69-75 16 Miyazawa M, Kasahara H, Kameoka H. Biotransformation of (+)-magnolin and (+)-yangabin in rat. Phytochemistry. 1993; 32 1421-1424 17 Smite E, Pan H, Lundgren L N. Lignan glycosides from inner bark of Betula pendula. Phytochemistry. 1995; 40 341-343 18 Yoshinari K, Sashida Y, Shimomura H. Two new lignan xylosides from the barks of Prunus ssiori and Prunus padus. Chem Pharm Bull. 1989; 37 3301-3303 19 Ouyang M A, Wein Y S, Su R K, Kuo Y H. Rhusemialins A–C, new cyclolignan ester from the roots of Rhus javanica var. roxburghiana. Chem Pharm Bull. 2007; 55 804-807 Prof. Ting-Ting Jong Department of ChemistryNational Chung Hsing University 250 Kuo-Kuang Road 402 Taichung Taiwan, R. O. C. Phone: + 88 64 22 84 04 11 ext. 701 Email: ttjong@mail.nchu.edu.tw Supplementary Material Supplementary Material www.thieme-connect.de/ejournals/toc/plantamedica
