Structure of hierridin c, synthesis of hierridins b and c, and evidence for prevalent alkylresorcinol biosynthesis in picocyanobacteria

Costa, Margarida Sofia, Sampaio-Dias, Ivo E., Castelo-Branco, Raquel, Scharfenstein, Hugo, Rezende de Castro, Roberta C., Artur M. S. Silva, Schneider, Maria Paula Cruz, Araújo, Maria João, R. Martins, Valentina F. Domingues, F Nogueira, Camões, Vera, Vitor Vasconcelos, Leão, Pedro Nuno

Research output: Contribution to journalArticle

Abstract

Small, single-celled planktonic cyanobacteria are ubiquitous in the world's oceans yet tend not to be perceived as secondary metabolite-rich organisms. Here we report the isolation and structure elucidation of hierridin C, a minor metabolite obtained from the cultured picocyanobacterium Cyanobium sp. LEGE 06113. We describe a simple, straightforward synthetic route to the scarcely produced hierridins that relies on a key regioselective halogenation step. In addition, we show that these compounds originate from a type III PKS pathway and that similar biosynthetic gene clusters are found in a variety of bacterial genomes, most notably those of the globally distributed picocyanobacteria genera Prochlorococcus, Cyanobium and Synechococcus. © 2019 American Chemical Society and American Society of Pharmacognosy.
Original languageEnglish
Pages (from-to)393-402
Number of pages9
JournalJournal Of Natural Products
VolumeVol. 82
Issue numbern.º 2
DOIs
Publication statusPublished - 22 Feb 2019

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Prochlorococcus
Synechococcus
Bacterial Genomes
Halogenation
Biosynthesis
Biosynthetic Pathways
Cyanobacteria
Multigene Family
Metabolites
Oceans and Seas
Genes

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Margarida Sofia, C., Ivo E., S-D., Raquel, C-B., Hugo, S., Roberta C., R. D. C., Silva, A. M. S., ... Pedro Nuno, L. (2019). Structure of hierridin c, synthesis of hierridins b and c, and evidence for prevalent alkylresorcinol biosynthesis in picocyanobacteria. Journal Of Natural Products, Vol. 82(n.º 2), 393-402. https://doi.org/10.1021/acs.jnatprod.8b01038
Margarida Sofia, Costa, ; Ivo E., Sampaio-Dias, ; Raquel, Castelo-Branco, ; Hugo, Scharfenstein, ; Roberta C., Rezende de Castro, ; Silva, Artur M. S. ; Maria Paula Cruz, Schneider, ; Maria João, Araújo, ; Martins, R. ; Domingues, Valentina F. ; Nogueira, F ; Vera, Camões, ; Vasconcelos, Vitor ; Pedro Nuno, Leão, . / Structure of hierridin c, synthesis of hierridins b and c, and evidence for prevalent alkylresorcinol biosynthesis in picocyanobacteria. In: Journal Of Natural Products. 2019 ; Vol. Vol. 82, No. n.º 2. pp. 393-402.
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abstract = "Small, single-celled planktonic cyanobacteria are ubiquitous in the world's oceans yet tend not to be perceived as secondary metabolite-rich organisms. Here we report the isolation and structure elucidation of hierridin C, a minor metabolite obtained from the cultured picocyanobacterium Cyanobium sp. LEGE 06113. We describe a simple, straightforward synthetic route to the scarcely produced hierridins that relies on a key regioselective halogenation step. In addition, we show that these compounds originate from a type III PKS pathway and that similar biosynthetic gene clusters are found in a variety of bacterial genomes, most notably those of the globally distributed picocyanobacteria genera Prochlorococcus, Cyanobium and Synechococcus. {\circledC} 2019 American Chemical Society and American Society of Pharmacognosy.",
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Margarida Sofia, C, Ivo E., S-D, Raquel, C-B, Hugo, S, Roberta C., RDC, Silva, AMS, Maria Paula Cruz, S, Maria João, A, Martins, R, Domingues, VF, Nogueira, F, Vera, C, Vasconcelos, V & Pedro Nuno, L 2019, 'Structure of hierridin c, synthesis of hierridins b and c, and evidence for prevalent alkylresorcinol biosynthesis in picocyanobacteria', Journal Of Natural Products, vol. Vol. 82, no. n.º 2, pp. 393-402. https://doi.org/10.1021/acs.jnatprod.8b01038

Structure of hierridin c, synthesis of hierridins b and c, and evidence for prevalent alkylresorcinol biosynthesis in picocyanobacteria. / Margarida Sofia, Costa, ; Ivo E., Sampaio-Dias, ; Raquel, Castelo-Branco, ; Hugo, Scharfenstein, ; Roberta C., Rezende de Castro, ; Silva, Artur M. S.; Maria Paula Cruz, Schneider, ; Maria João, Araújo, ; Martins, R.; Domingues, Valentina F.; Nogueira, F; Vera, Camões, ; Vasconcelos, Vitor; Pedro Nuno, Leão, .

In: Journal Of Natural Products, Vol. Vol. 82, No. n.º 2, 22.02.2019, p. 393-402.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Structure of hierridin c, synthesis of hierridins b and c, and evidence for prevalent alkylresorcinol biosynthesis in picocyanobacteria

AU - Margarida Sofia, Costa,

AU - Ivo E., Sampaio-Dias,

AU - Raquel, Castelo-Branco,

AU - Hugo, Scharfenstein,

AU - Roberta C., Rezende de Castro,

AU - Silva, Artur M. S.

AU - Maria Paula Cruz, Schneider,

AU - Maria João, Araújo,

AU - Martins, R.

AU - Domingues, Valentina F.

AU - Nogueira, F

AU - Vera, Camões,

AU - Vasconcelos, Vitor

AU - Pedro Nuno, Leão,

PY - 2019/2/22

Y1 - 2019/2/22

N2 - Small, single-celled planktonic cyanobacteria are ubiquitous in the world's oceans yet tend not to be perceived as secondary metabolite-rich organisms. Here we report the isolation and structure elucidation of hierridin C, a minor metabolite obtained from the cultured picocyanobacterium Cyanobium sp. LEGE 06113. We describe a simple, straightforward synthetic route to the scarcely produced hierridins that relies on a key regioselective halogenation step. In addition, we show that these compounds originate from a type III PKS pathway and that similar biosynthetic gene clusters are found in a variety of bacterial genomes, most notably those of the globally distributed picocyanobacteria genera Prochlorococcus, Cyanobium and Synechococcus. © 2019 American Chemical Society and American Society of Pharmacognosy.

AB - Small, single-celled planktonic cyanobacteria are ubiquitous in the world's oceans yet tend not to be perceived as secondary metabolite-rich organisms. Here we report the isolation and structure elucidation of hierridin C, a minor metabolite obtained from the cultured picocyanobacterium Cyanobium sp. LEGE 06113. We describe a simple, straightforward synthetic route to the scarcely produced hierridins that relies on a key regioselective halogenation step. In addition, we show that these compounds originate from a type III PKS pathway and that similar biosynthetic gene clusters are found in a variety of bacterial genomes, most notably those of the globally distributed picocyanobacteria genera Prochlorococcus, Cyanobium and Synechococcus. © 2019 American Chemical Society and American Society of Pharmacognosy.

UR - https://pubs.acs.org/doi/10.1021/acs.jnatprod.8b01038#

U2 - 10.1021/acs.jnatprod.8b01038

DO - 10.1021/acs.jnatprod.8b01038

M3 - Article

VL - Vol. 82

SP - 393

EP - 402

JO - Journal Of Natural Products

JF - Journal Of Natural Products

SN - 0163-3864

IS - n.º 2

ER -