Hassallidins, antifungal glycolipopeptides, are widespread among cyanobacteria and are the end-product of a nonribosomal pathway

Vestola, Johanna; Shishido, Tânia Keiko; Jokela, Jouni; Fewer, David P.; Aitio, Olli; Permi, Perttu; Wahlsten, Matti; Wang, Hao; Rouhiainen, Leo; Sivonen, Kaarina

doi:10.1073/pnas.1320913111

Cited by 102 publications

(128 citation statements)

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“…Discussion Synergistic Antifungal Activity. Cyanobacteria are known to produce lipopeptides with antifungal activity, such as nostofungicidine (18), laxaphycins (19)(20)(21), lobocyclamides (22), and hassallidins (14,23,24). In this study, we show that anabaenolysins have a weak antifungal activity (Fig.…”

Section: Significancementioning

confidence: 51%

“…Lipopeptides are commonly produced by cyanobacteria and present a broad range of bioactivity, including different types of cytotoxicity, growth, and enzyme inhibition of various organisms (fungi, bacteria, plants, protozoa, microalgae, and viruses) (9). A large number of lipopeptides have been described from cyanobacteria, such as barbamide (10), jamaicamide (11), curacin A (12), lyngbyatoxin (13) hassallidin (14), and puwainaphycins (15). Many lipopeptides are synthesized by large multifunctional enzymes known as polyketide synthases (PKSs) and nonribosomal peptide synthetases (NRPSs) (10)(11)(12)(13).…”

mentioning

confidence: 99%

“…PKS modules directly synthesize the lipophilic part of the curacin A (12), whereas the activation of the fatty acid chain incorporated in jamaicamide involves an acyl-acyl carrier protein synthetase (JamA) (10). In the hassallidin gene cluster, produced by Anabaena sp., the involvement of an acyl-protein synthetase and ligase (HasG), an acyl carrier protein (HasH), and a 3-oxoacyl (acyl-carrier-protein) reductase (HasL) are predicted to be involved in the fatty acid synthesis and incorporation in this nonribosomal glycolipopeptide (14), whereas the synthesis of the hybrid puwainaphycins in Cylindrospermum alatosporum involves a fatty-acyl ligase (FAAL) (15).…”

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confidence: 99%

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Antifungal activity improved by coproduction of cyclodextrins and anabaenolysins in Cyanobacteria

Shishido

Jokela

Kolehmainen

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

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Cyclodextrins are cyclic oligosaccharides widely used in the pharmaceutical industry to improve drug delivery and to increase the solubility of hydrophobic compounds. Anabaenolysins are lipopeptides produced by cyanobacteria with potent lytic activity in cholesterolcontaining membranes. Here, we identified the 23-to 24-kb gene clusters responsible for the production of the lipopeptide anabaenolysin. The hybrid nonribosomal peptide synthetase and polyketide synthase biosynthetic gene cluster is encoded in the genomes of three anabaenolysin-producing strains of Anabaena. We detected previously unidentified strains producing known anabaenolysins A and B and discovered the production of new variants of anabaenolysins C and D. Bioassays demonstrated that anabaenolysins have weak antifungal activity against Candida albicans. Surprisingly, addition of the hydrophilic fraction of the whole-cell extracts increased the antifungal activity of the hydrophobic anabaenolysins. The fraction contained compounds identified by NMR as α-, β-, and γ-cyclodextrins, which undergo acetylation. Cyclodextrins have been used for decades to improve the solubility and bioavailability of many drugs including antifungal compounds. This study shows a natural example of cyclodextrins improving the solubility and efficacy of an antifungal compound in an ancient lineage of photosynthetic bacteria.natural products | bioactive compounds | hydroxyamino fatty acid | NRPS | PKS

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Section: Significancementioning

confidence: 51%

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confidence: 99%

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confidence: 99%

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Antifungal activity improved by coproduction of cyclodextrins and anabaenolysins in Cyanobacteria

Shishido

Jokela

Kolehmainen

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

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“…strain 90 (here Anabaena 90) was isolated in 1987 from a toxic cyanobacterial bloom in Lake Vesijärvi, Finland (20). The strain produces many nonribosomally and ribosomally synthesized bioactive compounds, including hepatotoxic microcystin (20)(21)(22)(23)(24)(25)(26)(27). The genome of Anabaena 90 contains two pstABCS operons and genes for several enzymes recognized as phosphonate transporters and phosphatases, leading us to the hypothesis that the strain may be capable of using various phosphorus sources (27).…”

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confidence: 99%

Transcriptomic and Proteomic Profiling of Anabaena sp. Strain 90 under Inorganic Phosphorus Stress

Teikari

Österholm

Kopf

et al. 2015

Appl Environ Microbiol

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cInorganic phosphorus (P i ) is one of the main growth-limiting factors of diazotrophic cyanobacteria. Due to human activity, the availability of P i has increased in water bodies, resulting in eutrophication and the formation of massive cyanobacterial blooms. In this study, we examined the molecular responses of the cyanobacterium Anabaena sp. strain 90 to phosphorus deprivation, aiming at the identification of candidate genes to monitor the P i status in cyanobacteria. Furthermore, this study increased the basic understanding of how phosphorus affects diazotrophic and bloom-forming cyanobacteria as a major growth-limiting factor. Based on RNA sequencing data, we identified 246 differentially expressed genes after phosphorus starvation and 823 differentially expressed genes after prolonged P i limitation, most of them related to central metabolism and cellular growth. The transcripts of the genes related to phosphorus transport and assimilation (pho regulon) were most upregulated during phosphorus depletion. One of the most increased transcripts encodes a giant protein of 1,869 amino acid residues, which contains, among others, a phytase-like domain. Our findings predict its crucial role in phosphorus starvation, but future studies are still needed. Using twodimensional difference in gel electrophoresis (2D-DIGE) and liquid chromatography-tandem mass spectrometry (LC-MS/MS), we found 43 proteins that were differentially expressed after prolonged phosphorus stress. However, correlation analysis unraveled an association only to some extent between the transcriptomic and proteomic abundances. Based on the present results, we suggest that the method used for monitoring the P i status in cyanobacterial bloom should contain wider combinations of pho regulon genes (e.g., PstABCS transport systems) in addition to the commonly used alkaline phosphatase gene alone. N itrogen and phosphorus loading into aquatic ecosystems is a global problem causing enhanced primary production of photoautotrophic organisms (1-3). Among them, cyanobacteria are major beneficiaries of turbid and eutrophic water. They employ numerous ecophysiological strategies such as the capability for using various nutrient sources, gas vacuoles, photoprotective pigments, and UV-absorbing compounds, which enable them to survive and grow under eutrophic conditions and may lead to the formation of harmful and toxic blooms (1, 4). The theory that nutrient loading is a crucial factor causing harmful cyanobacterial blooms is supported by numerous field and laboratory studies showing that toxin production and growth rate both increase under nutrient-replete conditions (2, 5-8).The diazotrophic Anabaena is one of the most common bloomforming cyanobacterial genera in freshwater and brackish-water ecosystems, alongside Microcystis and Nodularia, respectively (4, 9), and some strains are capable of producing the following toxins: microcystins, anatoxin-a, anatoxin-a(S), and saxitoxins (4, 10). The ecology of these cyanobacteria thus deserves more attention. The abil...

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“…is believed to contribute to the defense against chytrid fungi (SØnstebØ and Rohrlack, 2011;Rohrlack et al, 2013). In cyanobacteria, the antifungal hassallidin is synthesized by NRPSs and tailoring enzymes (Vestola et al, 2014). Interestingly, a single hassallidin gene cluster encoded in the biosynthetic pathway for more than 40 chemical variants of hassallidin in Anabaena sp.…”

Section: S M El-moghazy Et Almentioning

confidence: 99%

Fungicidal effect of some promising agents in controlling maize late wilt disease and their potentials in developing yield productivity

Shalaby

Mehesen

Elbagory

2017

EBSS

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ANTIFUNGAL activities of cyanobacterial filtrate, compost tea, H 2 O 2 , garlic oil, barnyardgrass root exudates and Premis fungicide were tested against Cephalosporium maydis, the pathogenic fungus of late wilt disease of maize plants. In vitro and two field trials were carried out during 2015 and 2016 growing seasons under disease nursery conditions. In vitro, cyanobacterial filtrate and 30% premis fungicide were the superior treatments, by them linear growth of C. maydis were prevented totally and fulfillment inhibitions (100 %) were resultedwith lowest IC 50 values. Cyanobacterial filtrate and 3% H 2 O 2 were more effective in developing grain germination. Disease incidence showed better efficacy due to use 30 % Premis fungicide followed by 3 % H 2 O 2 with massive disease reductions reached 83.21 and 75.37 %, respectively during 2015 season. Effectiveness of the 3 % H 2 O 2 dose was extended to the 2016 season with 5.11 % disease incidence and 73.39 % disease reduction. For grain productivity, remarkable enhancements in the weights of both 10 ears and 1000 grains due to all treatments compared to control were recorded in both seasons. Due to their antifungal activities, qualitative analysis of Cyanobacterial filtrate and barnyardgrass root exudates was assayed on Gas chromatography mass-spectrum (GC-MS). Malonic acid, 2,3-Butandiol, Hexestrol, 12-Crown-4-ether and cis-Vaccenic acid were the major compounds extracted from the cultured blue-green algae. Whereas, Nadolol, Quinine, α-Methylionol, Phyllocladene, alcohols, acids, phenols and 2,6-dihydroxy benzoic acid were the most abundant antimicrobial agents in the barnyardgrass root exudates.

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Hassallidins, antifungal glycolipopeptides, are widespread among cyanobacteria and are the end-product of a nonribosomal pathway

Cited by 102 publications

References 56 publications

Antifungal activity improved by coproduction of cyclodextrins and anabaenolysins in Cyanobacteria

Antifungal activity improved by coproduction of cyclodextrins and anabaenolysins in Cyanobacteria

Transcriptomic and Proteomic Profiling of Anabaena sp. Strain 90 under Inorganic Phosphorus Stress

Fungicidal effect of some promising agents in controlling maize late wilt disease and their potentials in developing yield productivity

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