Planta Medica, Table of Contents Planta Med 2009; 75(13): 1431-1435DOI: 10.1055/s-0029-1185698 Natural Product Chemistry Original Paper © Georg Thieme Verlag KG Stuttgart · New York Sesquiterpene Lactone 12,8-Eudesmanolides from the Fungus Xylaria ianthinovelutina Pattama Pittayakhajonwut1 , Atit Usuwan1 , Chakapong Intaraudom1 , Sukitaya Veeranondha1 , Prasert Srikitikulchai1 1National Center for Genetic Engineering and Biotechnology (BIOTEC), Thailand Science Park, Klong Luang, Pathumthani, Thailand Recommend Article Abstract Buy Article Abstract The investigation of Xylaria ianthinovelutina (Mont.) led to the isolation of four new 12,8-eudesmanolides (1–4). Their structures were determined by spectroscopy and the relative stereochemistry was assigned based on NOESY and CD spectral data. Compounds 1–4 exhibited biological activity against Plasmodium falciparum K-1 strain, NCI-H187, KB, MCF-7 with IC50 values varying in the range 0.78–19.15 µg/mL. Key words Xylariaceae - Xylaria - Xylaria ianthinovelutina - sesquiterpene lactones - 12,8‐eudesmanolides Full Text References References 1 Deyrup S T, Gloer J B, O'Donnell K, Wicklow D T. Kolokosides A – D: triterpenoid glycosides from a Hawaiian isolate of Xylaria sp. J Nat Prod. 2007; 70 378-382 2 Pittayakhajonwut P, Suvannakad R, Thienhirun S, Prabpai S, Kongsaeree P, Tanticharoen M. An anti-herpes simplex virus-type 1 agent from Xylaria mellisii (BCC 1005). Tetrahedron Lett. 2005; 46 1341-1344 3 Lin Y, Wu X, Feng S, Jiang G, Luo J, Zhou S, Vrijmoed L LP, Jones E BG, Krohn K, Steingröver K, Zsila F. Five unique compounds: xyloketals from mangrove fungus Xylaria sp. from the South China Sea coast. J Org Chem. 2001; 66 6252-6256 4 Changsen C, Franzblau S G, Palittapongarnpim P. Improved green fluorescent protein reporter gene-based microplate screening for antituberculosis compounds by utilizing an acetamidase promoter. Antimicrob Agents Chemother. 2003; 47 3682-3687 5 Desjardins R E, Canfield C J, Haynes J D, Chulay J D. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique. Antimicrob Agents Chemother. 1979; 16 710-718 6 O'Brien J, Wilson I, Orton T, Pognan F. Investigation of the alamar blue (Resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity. Eur J Biochem. 2000; 267 5421-5426 7 Fischer N H, Olivier E J, Fischer H D. Progress in the chemistry of organic natural products. Wien; Springer 1979: 92-94 8 Asakawa Y, Matsuda R, Toyota M, Takemoto T, Connolly J D, Phillips W R. Sesquiterpenoids from Chiloscyphus, Clasmatocolea and Frullania species. Phytochemistry. 1983; 22 961-964 9 Jakupovic J, Schuster A, Bohlmann F, King R M, Lander N S. Sesquiterpene lactones from Gnephosis species. Phytochemistry. 1988; 27 3181-3185 10 Appendino G, Gariboldi P, Nano G M. Isomeric hydroperoxyeudesmanolides from Artemisia umbelliformis. Phytochemistry. 1983; 22 2767-2772 11 Tana R X, Jakupovica J, Bohlmanna F, Jiab Z J, Huneck S. Sesquiterpene lactones and other constituents from Artemisia xerophytica. Phytochemistry. 1991; 30 583-587 12 Rustaiyan A, Habibi Z, Saberi M, Jakupovic J. A nor-guaianolide and a glaucolide-like eudesmanolide from Pulicaria undulata. Phytochemistry. 1991; 30 2405-2406 13 Jakupovic J, Ganzer U, Pritschow P, Lehmann L, Bohlmann F, Kinga R M. Sesquiterpene lactones and other constituents from Ursinia species. Phytochemistry. 1992; 31 863-880 14 Gören N, Ulubelen A, Bozok-Johansson C, Tahtasakal E. Sesquiterpene lactones from Tanacetum densum subsp. amani. Phytochemistry. 1993; 33 1157-1159 15 Gören N, Tahtasakal E. Constituents of Tanacetum densum subsp. eginense. Phytochemistry. 1994; 36 1281-1282 16 Gören N, Woerdenbag H J, Bozok-Johansson C. Cytotoxic and antibacterial activities of sesquiterpene lactones isolated from Tanacetum praeteritum subsp. praeteritum. Planta Med. 1996; 62 419-422 17 Farag S F, El-Emary N A, Masatake N. Eudesmanolides from Wedalia prostrata. Chem Pharm Bull. 1996; 44 661-664 18 Zdero C, Bohlmann F. Eremophilanolides, eudesmanolides, guaianolides and other constituents from Ondetia linearis. Phytochemistry. 1989; 28 1653-1660 19 Asakawa Y, Toyota M, Takemoto T, Suire C. Pungent sesquiterpene lactones of the European liverworts Chiloscyphus polyanthus and Diplophyllum albicans. Phytochemistry. 1979; 18 1007-1009 Dr. Pattama Pittayakhajonwut National Center for Genetic Engineering and Biotechnology (BIOTEC)Thailand Science Park Paholyothin Road Klong Luang 12120 Pathumthani Thailand Phone: + 66 25 64 67 00 ext. 35 59 Fax: + 66 25 64 66 32 Email: pattamap@biotec.or.th Supplementary Material Supplementary Material www.thieme-connect.de/ejournals/toc/plantamedica