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. 2015 Apr 13;13(4):2124-40.
doi: 10.3390/md13042124.

Antifungal compounds from cyanobacteria

Tânia K Shishido  1 , Anu Humisto  2 , Jouni Jokela  3 , Liwei Liu  4 , Matti Wahlsten  5 , Anisha Tamrakar  6 , David P Fewer  7 , Perttu Permi  8 , Ana P D Andreote  9 , Marli F Fiore  10 , Kaarina Sivonen  11
Affiliations

Antifungal compounds from cyanobacteria

Tânia K Shishido et al. Mar Drugs. .

Abstract

Cyanobacteria are photosynthetic prokaryotes found in a range of environments. They are infamous for the production of toxins, as well as bioactive compounds, which exhibit anticancer, antimicrobial and protease inhibition activities. Cyanobacteria produce a broad range of antifungals belonging to structural classes, such as peptides, polyketides and alkaloids. Here, we tested cyanobacteria from a wide variety of environments for antifungal activity. The potent antifungal macrolide scytophycin was detected in Anabaena sp. HAN21/1, Anabaena cf. cylindrica PH133, Nostoc sp. HAN11/1 and Scytonema sp. HAN3/2. To our knowledge, this is the first description of Anabaena strains that produce scytophycins. We detected antifungal glycolipopeptide hassallidin production in Anabaena spp. BIR JV1 and HAN7/1 and in Nostoc spp. 6sf Calc and CENA 219. These strains were isolated from brackish and freshwater samples collected in Brazil, the Czech Republic and Finland. In addition, three cyanobacterial strains, Fischerella sp. CENA 298, Scytonema hofmanni PCC 7110 and Nostoc sp. N107.3, produced unidentified antifungal compounds that warrant further characterization. Interestingly, all of the strains shown to produce antifungal compounds in this study belong to Nostocales or Stigonematales cyanobacterial orders.

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Figures

Figure 1
Figure 1
7-OMe-scytophycin-B (1) isolated from Anabaena sp. HAN21/1 and 7-OMe-scytophycin-B reacted by light (2) after the Paternò–Büchi reaction. Stereochemistry is according to the literature.
Figure 2
Figure 2
Total ion current chromatograms of methanol extracts of Scytonema sp. HAN3/2, Nostoc sp. HAN11/1, Anabaena sp. HAN21/1 and Anabaena cf. cylindrica PH133 showing the elution of scytophycin variants 1–33. Bolded numbers and arrows show the main scytophycin variants.
Figure 3
Figure 3
The general chemical structure of hassallidin. M1–M3 are monosaccharides, R1 is the hydrocarbon chain of the fatty acid chain FA1 and R2–R10 side chains of amino acids Aa2 to Aa10.
Figure 4
Figure 4
Total ion current chromatograms of methanol extracts of Nostoc sp. CENA 219, Nostoc calcicula 6 sf Calc, Anabaena sp. HAN7/1 and Anabaena sp. BIR JV1 showing the elution of hassallidin variants 1–27.
Figure 5
Figure 5
The distribution of cyanobacterial strains producing antifungal compounds. The neighbor-joining phylogenetic tree is based on the 16S rRNA genes sequences constructed with 1000 bootstraps in which the percentages over 50 are indicated in each node. Studied strains are in bold.
See this image and copyright information in PMC

References

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