Sesquiterpene Lactone 12,8-Eudesmanolides from the Fungus Xylaria ianthinovelutina

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

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