David P. Fewer

University of Helsinki

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Kaarina Sivonen

University of Helsinki

Jouni Jokela

University of Helsinki

Matti Wahlsten

University of Helsinki

Perttu Permi

University of Helsinki

Leo Rouhiainen

University of Helsinki

Niina Leikoski

Radiation and Nuclear Safety Authority

Tânia Keiko Shishido

University of Helsinki

Hao Wang

Huazhong Agricultural University

Liwei Liu

Ningbo University

Marli Fátima Fiore

Universidade de São Paulo

Cooperative Institutions

University of Helsinki

111

University of California, San Diego

Biocenter Finland

Scripps Institution of Oceanography

Czech Academy of Sciences, Institute of Microbiology

University of Tübingen

Centre National de la Recherche Scientifique

Wageningen University & Research

Universidade de São Paulo

German Center for Infection Research

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Sphaerocyclamide, a prenylated cyanobactin from the cyanobacterium Sphaerospermopsis sp. LEGE 00249

Scientific Reports (2018)

Joana Martins Niina Leikoski Matti Wahlsten Joana Azevedo Jorge Antunes

Cyanobactins are a family of linear and cyclic peptides produced through the post-translational modification of short precursor peptides. A mass spectrometry-based screening of potential cyanobactin producers led to the discovery of a new prenylated member of this family of compounds, sphaerocyclamide (1), from Sphaerospermopsis sp. LEGE 00249. The sphaerocyclamide biosynthetic gene cluster (sph) encoding the novel macrocyclic prenylated cyanobactin, was sequenced. Heterologous expression of the sph gene cluster in Escherichia coli confirmed the connection between genomic and mass spectrometric data. Unambiguous establishment of the orientation and site of prenylation required the full structural elucidation of 1 using Nuclear Magnetic Resonance (NMR), which demonstrated that a forward prenylation occurred on the tyrosine residue. Compound 1 was tested in pharmacologically or ecologically relevant biological assays and revealed moderate antimicrobial activity towards the fouling bacterium Halomonas aquamarina CECT 5000.

Heterologous expression

Gene cluster

10.1038/s41598-018-32618-5

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Citations (37)

Erratum to The Diversity and Evolution of Rhizobia

Microbiology monographs (2008)

Aneta Dresler-Nurmi David P. Fewer Leena Räsänen Kristina Lindström

10.1007/7171_2008_117

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Anacyclamide D8P, a prenylated cyanobactin from a Sphaerospermopsis sp. cyanobacterium

Joana Martins Niina Leikoski Matti Wahlsten Joana Azevedo Jorge Antunes

Cyanobactins are a family of linear and cyclic peptides produced through the post-translational modification of short precursor peptides. Anacyclamides are macrocyclic cyanobactins with a highly diverse sequence that are common in the genus Anabaena . A mass spectrometry-based screening of potential cyanobactin producers led to the discovery of a new prenylated member of this family of compounds, anacyclamide D8P ( 1 ), from Sphaerospermopsis sp. LEGE 00249. The anacyclamide biosynthetic gene cluster ( acy ) encoding the novel macrocyclic prenylated cyanobactin, was sequenced. Heterologous expression of the acy gene cluster in Escherichia coli established the connection between genomic and mass spectrometric data. Unambiguous establishment of the type and site of prenylation required the full structural elucidation of 1 using Nuclear Magnetic Resonance (NMR), which demonstrated that a forward prenylation occurred on the tyrosine residue. Compound 1 was tested in pharmacologically or ecologically relevant biological assays and revealed moderate antimicrobial activity towards the fouling bacterium Halomonas aquamarina CECT 5000.

Heterologous expression

Halomonas

Gene cluster

10.26434/chemrxiv.5346739.v1

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Citations (1)

Antifungal Compounds from Cyanobacteria

Marine Drugs (2015)

Tânia Keiko Shishido Anu Humisto Jouni Jokela Liwei Liu Matti Wahlsten

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.

Nostoc

10.3390/md13042124

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Biosynthesis of the Bis-Prenylated Alkaloids Muscoride A and B

ACS Chemical Biology (2019)

Antti Mattila Rose-Marie Andsten Mikael Jumppanen Michele Assante Jouni Jokela

Prenylation is a common step in the biosynthesis of many natural products and plays an important role in increasing their structural diversity and enhancing biological activity. Muscoride A is a linear peptide alkaloid that contain two contiguous oxazoles and unusual prenyl groups that protect the amino- and carboxy-termini. Here we identified the 12.7 kb muscoride (mus) biosynthetic gene clusters from Nostoc spp. PCC 7906 and UHCC 0398. The mus biosynthetic gene clusters encode enzymes for the heterocyclization, oxidation, and prenylation of the MusE precursor protein. The mus biosynthetic gene clusters encode two copies of the cyanobactin prenyltransferase, MusF1 and MusF2. The predicted tetrapeptide substrate of MusF1 and MusF2 was synthesized through a novel tandem cyclization route in only eight steps. Biochemical assays demonstrated that MusF1 acts on the carboxy-terminus while MusF2 acts on the amino-terminus of the tetrapeptide substrate. We show that the MusF2 enzyme catalyzes the reverse or forward prenylation of amino-termini from Nostoc spp. PCC 7906 and UHCC 0398, respectively. This finding expands the regiospecific chemical functionality of cyanobactin prenyltransferases and the chemical diversity of the cyanobactin family of natural products to include bis-prenylated polyoxazole linear peptides.

Prenyltransferase

Tetrapeptide

Nonribosomal peptide

10.1021/acschembio.9b00620

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Discovery of Rare and Highly Toxic Microcystins from Lichen-Associated Cyanobacterium Nostoc sp. Strain IO-102-I

Applied and Environmental Microbiology (2004)

Ilona Oksanen Jouni Jokela David P. Fewer Matti Wahlsten Jouko Rikkinen

ABSTRACT The production of hepatotoxic cyclic heptapeptides, microcystins, is almost exclusively reported from planktonic cyanobacteria. Here we show that a terrestrial cyanobacterium Nostoc sp. strain IO-102-I isolated from a lichen association produces six different microcystins. Microcystins were identified with liquid chromatography-UV mass spectrometry by their retention times, UV spectra, mass fragmentation, and comparison to microcystins from the aquatic Nostoc sp. strain 152. The dominant microcystin produced by Nostoc sp. strain IO-102-I was the highly toxic [ADMAdda 5 ]microcystin-LR, which accounted for ca. 80% of the total microcystins. We assigned a structure of [DMAdda 5 ]microcystin-LR and [ d -Asp 3 ,ADMAdda 5 ]microcystin-LR and a partial structure of three new [ADMAdda 5 ]-XR type of microcystin variants. Interestingly, Nostoc spp. strains IO-102-I and 152 synthesized only the rare ADMAdda and DMAdda subfamilies of microcystin variants. Phylogenetic analyses demonstrated congruence between genes involved directly in microcystin biosynthesis and the 16S rRNA and rpoC1 genes of Nostoc sp. strain IO-102-I. Nostoc sp. strain 152 and the Nostoc sp. strain IO-102-I are distantly related, revealing a sporadic distribution of toxin production in the genus Nostoc. Nostoc sp. strain IO-102-I is closely related to Nostoc punctiforme PCC 73102 and other symbiotic Nostoc strains and most likely belongs to this species. Together, this suggests that other terrestrial and aquatic strains of the genus Nostoc may have retained the genes necessary for microcystin biosynthesis.

Nostoc

Strain (injury)

10.1128/aem.70.10.5756-5763.2004

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Citations (150)

Direct Evidence of Microbial Sunscreen Production by Scum‐Forming Cyanobacteria in the Baltic Sea

Environmental Microbiology Reports (2025)

Inkeri Vuori Greta Gaiani Sıla Arsın Endrews Delbaje Julia Järn

ABSTRACT Mycosporine‐like amino acids are water‐soluble secondary metabolites that protect photosynthetic microorganisms from ultraviolet radiation. Here, we present direct evidence for the production of these compounds in surface scums of cyanobacteria along the Baltic Sea coast. We collected 59 environmental samples from the southern coast of Finland during the summers of 2021 and 2022 and analysed them using high‐resolution liquid chromatography‐mass spectrometry. Our results revealed the presence of microbial sunscreens in nearly all surface scum samples. Mycosporine‐like amino acids are synthesised through the coordinated action of four biosynthetic enzymes encoded in a compact biosynthetic pathway. Bioinformatics analysis of the mysB biosynthetic gene from a surface scum indicated that the cyanobacteria responsible for production belonged to the Anabaena / Dolichospermum / Aphanizomenon species complex. We mapped the distribution of biosynthetic enzymes onto a phylogenomic tree, utilising 120 bacterial single‐copy conserved genes from 101 draft or complete genomes within the species complex. This analysis showed that 48% of identified species possess the ability to produce these compounds, with biosynthetic pathways being most common in Dolichospermum and Aphanizomenon strains. We detected the production of porphyra‐334 and shinorine, two widely reported family members, in Dolichospermum strains isolated from the Gulf of Finland's surface layer. The estimated content of porphyra‐334 in Dolichospermum sp. UHCC 0684 was 7.4 mg per gram dry weight. Our results suggest that bloom‐forming cyanobacteria could be a potential source of these compounds for cosmetic and biotechnological applications and may play a significant role in cyanobacterial bloom formation.

Baltic sea

10.1111/1758-2229.70056

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Citations (0)

UV-protective secondary metabolites from cyanobacteria

Elsevier eBooks (2022)

Teresa P. Martins Sıla Arsın David P. Fewer Pedro N. Leão

Heterologous

10.1016/b978-0-12-821491-6.00005-3

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Citations (5)

Horizontal Gene Transfer and Recombination Shape Mesorhizobial Populations in the Gene Center of the Host Plants Astragalus Luteolus and Astragalus Ernestii in Sichuan, China