2018 Springer Science+Business Media, LLC
Chemistry of Natural Compounds, Vol. 54, No. 3, May, 2018
B R I E F C O M M U N I C A T I O N S
NONPOLAR COMPOUNDS AND FREE FATTY ACIDS
FROM SEVERAL ISOLATES OF MARINE
FUNGUS Penicillium antarcticum
G. K. Oleinikova,* N. N. Kirichuk, and Sh. Sh. Afiyatullov
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  and rice medium  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
(100:0o90:10). 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 Et
O) and pyrrolidides . 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,
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.
G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch, Russian Academy of Sciences, 159
Prosp. 100 Let Vladivostoku, Vladivostok, 690022, Russian Federation, fax: (4232) 31 40 50, e-mail: email@example.com.
Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2018, pp. 453–455. Original article submitted
December 27, 2017.