LAUSR

In continuation of research on biologically active compounds from extracts of marine isolates of fungi and micromycetes [1, 2], extracts of nine Far-Eastern strains of the marine fungus Penicillium antarcticum were investigated (Table 1). Strains of the fungus were cultivated for 14 d on malt-agar [3] and rice medium [4] that were prepared with seawater. Mycelia together with the medium were extracted with EtOAc. The culture extracts were concentrated at reduced pressure. The resulting dry solids were dissolved in EtOH (10%) and extracted sequentially with hexane, EtOAc, and BuOH. The hexane fractions were concentrated at reduced pressure and analyzed using GC-MS. Compounds were identified by comparing their mass spectra with those of standard compounds using the NIST98 database. Table 2 presents the results. Hexane fractions of all cultures contained linear paraffinic hydrocarbons, linear hydrocarbons with a terminal double bond, and their isomers. Strain 1 on malt-agar produced mainly olefinic hydrocarbons with a terminal double bond such as C16, C18, C20, C22, C24, C25, and C26 in addition to C22-diene-1,4; on rice medium, also linear paraffins C16 (6.79%), C17 (7.92%), and C18. Strain 2 produced olefinic hydrocarbons with a terminal double bond such as i-C18 (2.86%), C24, and C27 (9.48%) in addition to linear paraffins C23 (8.6%), C24, C26, and C27 (25–21%). The hexane fraction of the culture of 3 contained 11 paraffins (C19–C29) and eicosene (8.76%). Culture of 7 gave linear alkanes C20–C29 and i-heptacosane (5.24%). Strain 4 on malt-agar medium produced mainly linear paraffins C12 (19.7%) and C19–C29; on rice medium, C16, C18, C22, C25 with a terminal double bond and C22-diene-1,4. The hexane fraction of culture 5 on malt-agar medium contained only linear hydrocarbons C20–C30 and C32; on rice medium, hydrocarbons were absent. The other cultures produced linear paraffins and olefinic hydrocarbons with a terminal double bond for C12–C30. Strains 8 and 9 produced triacontane (11.15 and 5.03%, respectively). Strains 1, 2, 5, and 6 produced squalene as follows. 1 (on both media), 8.55 and 14.52%, respectively; 2 and 6 (on rice medium), 34.17 and 48.63%, respectively; 5 (on malt-agar medium), 4.03% (% of total mass of hexane fraction). EtOAc fractions of each culture were chromatographed over a column of silica gel using a hexane–EtOAc gradient (100:0 90:10). Free fatty acids and phthalates eluted with the 95:5 fraction. The obtained sums were analyzed by GC-MS as methyl esters (methylated by diazomethane in Et2O) and pyrrolidides [5]. Derivatives were identified by comparing their mass spectra with those of standard compounds using the NIST98 database. Table 3 presents the results. Most cultures produced fatty acids 16:0, 18:2, 18:1, and 18:0. Cultures of 5, 6, 7, and 9 (malt-agar medium) and 4 (rice medium) did not produce 18:2(9,12) acid. Several strains produced small quantities of other acids, e.g., 1, 19:2(9,12) (1.9%, rice medium); 5 and 6, 14:0 (2.15 and 1.57%, respectively, malt-agar medium); 6 and 1, 15:0 (1.15 and 0.86%, respectively, malt-agar medium). Extracts of cultures contained phthalates (5–28% of the fatty-acid fraction weight). The total phthalate contents in extracts of cultures grown on rice medium were less than in those grown on malt-agar medium. Phthalates were not detected in extracts of cultures of 3 and 4 grown on rice medium.