Analysis and Isolation of Secondary Metabolites of Bipolaris sorokiniana by Different Chromatography Techniques and the
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ysis and Isolation of Secondary Metabolites of Bipolaris sorokiniana by Different Chromatography Techniques and the Spectrum of Their Biological Activity A. O. Berestetskiya, *, A. A. Dalinovaa, V. R. Dubovika, E. N. Grigoryevaa, D. M. Kochurab, I. V. Senderskiya, S. N. Smirnovc, E. A. Stepanychevaa, and S. M. Turaevad aAll-Russian
Institute of Plant Protection, St. Petersburg, 196608 Russia Research Institute of Hygiene, Occupational Pathology and Human Ecology, St. Petersburg, 188663 Russia c St. Petersburg State University, St. Petersburg, 199034 Russia dInstitute of the Chemistry of Plant Substances, Tashkent, 100170 Uzbekistan *e-mail: [email protected]
b
Received December 30, 2019; revised April 14, 2020; accepted April 22, 2020
Abstract—Secondary metabolites were isolated from cultures of four geographically distant isolates of the cosmopolitan fungus, Bipolaris sorokiniana for intense biological characterization. Analysis of extracts from their liquid and solid cultures with TLC and HPLC-MS showed high similarity of their composition despite on fungal origin. From the extracts of B. sorokiniana 14 metabolites (terpenes, quinones, xanthones etc.) were isolated using column chromatography and preparative HPLC; among them, 12 known substances were identified. Chloromonilinic acid B (CAB) showed the highest level phytotoxic activity on wheat leaves. The most of isolated compounds inhibited growth of Bacillus subtilis, of which methyl-8,3-hydroxy-3-methyl-4-chloroxanthon-1-carboxilate (MMC) demonstrated the strongest activity. Some metabolites of B. sorokiniana (CAB and MMC) were shown to have insecticidal activity against common cereal aphid. All the compounds were cytotoxic (especially, cochlioqionones and fusaroproliferin) when tested on Sf9 cell line. However, no one was acute toxic for infusoria. Evidently, the production of multiple bioactive compounds makes B. sorokiniana a strong competitor in different ecological niches and a dangerous contaminant of grain. Keywords: Bipolaris sorokiniana, chemical ecology, secondary metabolites DOI: 10.1134/S0003683820050051
INTRODUCTION The cosmopolitan fungus, Bipolaris sorokiniana infects various organs of grasses and cereals, and is capable of endophytic, epiphytic and soil growth. This micromycete is a widespread causal agent of root rot and leaf blotch of cereals, which cause significant economic damage. The infection of cereal grains with the phytopathogen decreases their quality and germination and increases mycotoxin accumulation (e.g., sterigmatocystin) [1–4]. The research on biologically active metabolites of B. sorokiniana began in the mid-20th century and continues in the present, making it possible to detect more and more new compounds. They include substances of various biological activity (phytotoxic, antimicrobial, nematicidal, cytotoxic, etc.) and chemical structure (Fig. 1, Table 1). The metabolites of B. sorokiniana probably also have insecticidal properties [5]. Studies on the isolation and characterization of B. sorokiniana metabolites
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