Evaluation of Antimycobacterial, Antiplasmodial and Cytotoxic Activities of Preussomerins Isolated from the Lichenicolous Fungus Microsphaeropsis sp. BCC 3050

Abstract

A new preussomerin isomer, 3′-O-demethylpreussomerin I, five known preussomerins E - I, and two known deoxypreussomerins, deoxypreussomerin A and bipendensin (palmarumycin C₁₁), were isolated from a lichenicolous fungus Microsphaeropsis sp. BCC 3050. These structures were elucidated by spectroscopic methods, especially 1D- and 2D-NMR. The preussomerins were evaluated for their antimycobacterial and antiplasmodial activities as well as cytotoxicity against KB, BC-1 and vero cell lines.

Key words

Microsphaeropsis sp. - lichenicolous fungi - preussomerins - antiplasmodial activity - antimycobacterial activity

References

• 1 Weber H A, Baenziger N C, Gloer J B. Structures of preussomerin A: an unusual new antifungal metabolite from the coprophilous fungus Preussia isomera .  Journal of the American Chemical Society. 1990;  112 6718-9
• 2 Weber H A, Gloer J B. The Preussomerins: Novel antifungal metabolites from the coprophilous fungus Preussia isomera Cain.  Journal of Organic Chemistry. 1991;  56 4355-60
• 3 Soman A G, Gloer J B. Sporovexins A-C and a new preussomerin analog: antibacterial and antifungal metabolites from the coprophilous fungus Sporormiella vexans .  Journal of Natural Products. 1999;  62 659-61
• 4 Singh S B, Zink D L, Liesch J M, Ball R G, Goetz M A, Bolessa E A. et al . Preussomerins and deoxypreussomerins: Novel inhibitors of ras farnesyl-protein transferase.  Journal of Organic Chemistry. 1994;  59 6296-302
• 5 Polishook J D, Dombrowski A W, Tsou N N, Salituro G M, Curotto J E. Preussomerin D from the endophyte Hormonema dematioides .  Mycologia. 1993;  85 62-4
• 6 Shannon C, Heathcock C H. Total syntheses of (±)-preussomerins G and I.  Organic Letters. 1999;  1 3-5
• 7 Ragot J P, Steeneck C, Alcaraz M -L, Taylor R JK. The synthesis of 1,8-dihydroxynaphthalene-derived natural products: palmarumycin CP₁, palmarumycin CP₂, palmarumycin C₁₁, CJ-12,371, deoxypreussomerin A and novel analogues.  Journal of Chemical Society, Perkin Transactions. 1999;  1 1073-82
• 8 Isaka M, Jaturapat A, Kladwang W, Punya J, Lertwerawat Y, Tanticharoen M. et al . Antiplasmodial compounds from the wood-decayed fungus Xylaria sp. BCC 1067.  Planta Medica. 2000;  66 473-5
• 9 Nilanonta C, Isaka M, Kittakoop P, Palittapongarnpim P, Kamchonwongpaisan S, Pittayakhajonwut D. et al . Antimycobacterial and antiplasmodial cyclodepsipeptides from the insect pathogenic fungus Paecilomyces tenuipes BCC 1614.  Planta Medica. 2000;  66 756-8
• 10 Collins L, Franzblau S G. Microplate Alamar Blue Assay versus BACTEC 460 System for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium .  Antimicrobial Agents and Chemotherapy. 1997;  41 1004-9
• 11 Isaka M, Punya J, Lertwerawat Y, Tanticharoen M, Thebtaranonth Y. Antimalarial activity of macrocyclic trichothecenes isolated from the fungus Myrothecium verrucaria .  Journal of Natural Products. 1999;  62 329-31
• 12 Desjardins R E, Canfield C J, Chulay J D. Quantitative assessment of antimalarial activity in vitro by semiautomated microdilution technique.  Antimicrobial Agents and Chemotherapy. 1979;  16 710-8
• 13 Skehan P, Storeng R, Scudiero D, Monks A, McMahon J D, Vistica D. et al . New colorimetric cytotoxicity assay for anticancer-drug screening.  Journal of National Cancer Institute. 1990;  82 1107-12
• 14 Kouam , Mpondo T N, Lavaud C, Massiot G, Nuzillard J -M, Connolly J D,. et al . Bipendensin, an unusual phenolic acetal from Afzelia bipendensis .  Natural Product Letters. 1993;  3 299-303
• 15 Krohn K, Michel A, Flörke U, Aust H -J, Draeger S, Schulz B. Palmarumycins C₁-C₁₆ from Coniothyrium sp.: isolation, structure elucidation, and biological activity. Justus Liebigs Annalen der Chemie 1994: 1099-108
• 16 Hayashi M, Kim Y P, Hiraoka H, Natori M, Takamatsu S, Kawakubo T. et al . Macrosphelide, a novel inhibitor of cell-cell adhesion molecule. I. Taxonomy, fermentation, isolation and biological activities.  Journal of Antibiotics. 1995;  48 1435-9
• 17 Takamatsu S, Kim Y P, Hayashi M, Hiraoka H, Natori Mkomiyama K. et al . Macrosphelide, a novel inhibitor of cell-cell adhesion molecule. II. Physicochemical properties and structural elucidation.  Journal of Antibiotics. 1996;  49 95-8
• 18 Tony-Lam Y K, Hensens O D, Ransom R, Giacobbe R A, Polishook J, Zink D. L-755,807, a new non-peptide bradykinin inhibitor from an endophytic Microsphaeropsis sp.  Tetrahedron. 1996;  52 1481-6
• 19 Funabashi Y, Horiguchi T, Iinuma S, Tanida S, Harada S. TAN-1496 A, C and E, diketopiperazine antibiotics with inhibitory activity against mammalian DNA topoisomerase I.  Journal of Antibiotics. 1994;  47 1202-18
• 20 Brauers G, Edrada R A, Ebel R, Proksch P, Wray V, Berg A. et al . Anthraquinones and betaenone derivatives from the sponge-associated fungus Microsphaeropsis species: novel inhibitors of protein kinases.  Journal of Natural Products. 2000;  63 739-45
• 21 Höller U, König G M, Wright A D. Three new metabolites from marine-derived fungi of the genera Coniothyrium and Microsphaeropsis.  Journal of Natural Products. 1999;  62 114-8
• 22 Yu C -M, Curtis J M, Wright J LC, Ayer S W, Fathi-Afshar Z R. An unusual fatty acid and its glyceride from the marine fungus Microsphaeropsis olivacea .  Canadian Journal of Chemistry. 1996;  74 730-5