Cytotoxic Lignan Esters from Cinnamomum osmophloeum

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

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