Sunday, August 10, 2008
P109

Malbranpyrroles, Novel Polyketides from Thermophilic Fungus Malbranchea sulfurea— Structure Elucidation by LC-SPE-NMR and LC-MS and Biosynthesis Studies

Yu-Liang Yang, Wan-Yun Liu, and Shih-Hsiung Wu. Institute of Biological Chemistry, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei, Taiwan

In the continuing research on the bioactive components from thermophlic microorganism, the crude extract of Malbranchea sulfurea showed significant cytotoxicity toward various cancer cell lines. One novel polyketide, malbranpyrrole A (1), was isolated from M. sulfurea. We have found that 1 can undergo the cis/trans photoisomerization during the experimental procedure. Thus, the crude extracts with and without UV irradiation were analyzed by using LC-DAD-MS. In addition to 1, we have also found that some components can undergo the cis/trans photoisomerization. In order to investigate the native structures of these photo-sensitive components, the LC-SPE-NMR and LC-MS were applied. Five polyketides structures, malbranpyrroles B-E (2-6), together with 1 were elucidated. Some of them are the halogenated polyketides. The LC-MS fingerprint indicated that the quantity of those halogenated polyketides would be varied in different culture medium. The biosynthetic pathway was proposed by the isotope feeding experiments.