Alkaloids from the Marine Isolate of the Fungus Aspergillus fumigatus

Chemistry of Natural Compounds
2005.0

Abstract

We previously isolated from the marine isolate of the fungus Aspergillus fumigatus KMM 4631 the five diketopiperazine antibiotics cyclotryprostatins A and B, fumitremorgin C, 12, 13-dihydrofumitremorgin C, and verruculogen [1]. Further research on metabolites of this strain afforded 1-5. Cultivation was performed under the previously described conditions [1]. The CHCl3:C2H5OH extract of A. fumigatus was chromatographed over a column of silica gel L (40/100 µm) with elution successively by CHCl3 and CHCl3:C2H5OH (10:1 and 5:1). Fractions eluted by CHCl3:C2H5OH (10:1) were combined, concentrated in vacuum to the minimal volume, and separated by HPLC over columns of Silasorb Si (ethylacetate:hexane, 4:1) and Diasphere-110-C18 (from 50 to 60% CH3OH in water) to afford 1 (4 mg), 2 (18 mg), 3 (3 mg), 4 (3.5 mg), and 5 (4 mg). Spectral data and two-dimensional spectra (DEPT, COSY-45, HSQC, HBMC, and NOESY) of 1 and 2 agree with those in the literature for fumiquinazolines C and D isolated from the marine isolate of A. fumigatus [2]. Spectral data for 3 agree with those in the literature for fumitremorgin B isolated from A. fumigatus parasitic on rice [3, 4]. Mass spectra and PMR spectra of 4 agree with those reported previously for bisdethiobis(methylthio)gliotoxin isolated from the fungi Gliocladium deliquescens [5], A. fumigatus [6], and Penicillium terlikowskii [7]. Mass spectra and PMR spectra of 5 agree with those reported previously in the literature for tryptoquivaline J isolated from the fungus A. fumigatus parasitic on rice [8]. Thus, A. fumigatus KMM 4631 is a new source of alkaloids of various structural types. Bisdethiobis(methylthio)gliotoxin (4) and tryptoquivaline J (5) were isolated from marine isolates of fungi for the first time.

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