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Monacyclinones, New Angucyclinone Metabolites Isolated from Streptomyces sp. M7_15 Associated with the Puerto Rican Sponge Scopalina ruetzleri.

Vicente J, Stewart AK, van Wagoner RM, Elliott E, Bourdelais AJ, Wright JL - Mar Drugs (2015)

Bottom Line: Of these, monacyclinones A-B (4-5) contain the core ring structure of dehydrorabelomycin (2) with the aminodeoxysugar found in frigocyclinone (1).All structures were confirmed through spectral analyses.The strongest bioactivity against rhabdomycosarcoma cancer cells and gram-positive bacteria was exhibited by compound 9, suggesting that the extra aminodeoxysugar subunit is important for biological activity.

View Article: PubMed Central - PubMed

Affiliation: Center for Marine Science, University of North Carolina Wilmington, 5600 Marvin K. Moss Lane Wilmington, NC 28409, USA. jvicente@umces.edu.

ABSTRACT
During an investigation of new actinomycete species from Caribbean sponges for novel bioactive natural products, frigocyclinone (1), dimethyldehydrorabelomycin (3) and six new angucyclinone derivatives were isolated from Streptomyces sp. strain M7_15 associated with the sponge Scopalina ruetzleri. Of these, monacyclinones A-B (4-5) contain the core ring structure of dehydrorabelomycin (2) with the aminodeoxysugar found in frigocyclinone (1). Monacyclinone C (6) is a hydroxylated variant of frigocyclinone (1) and monacyclinone D (7) is a Baeyer Villiger derivative of (6) which also exists as the open chain hydrolysis product monacyclinone E (8). Monacyclinone F (9) contains two unique epoxide rings attached to the angucyclinone moiety and an additional aminodeoxysugar attached through an angular oxygen bond. All structures were confirmed through spectral analyses. Activity against rhabdomycosarcoma cancer cells (SJCRH30) after 48 h of treatment was observed with frigocyclinone (1; EC50 = 5.2 µM), monacyclinone C (6; 160 µM), monacyclinone E (8; 270 µM), and monacyclinone F (9; 0.73 µM). The strongest bioactivity against rhabdomycosarcoma cancer cells and gram-positive bacteria was exhibited by compound 9, suggesting that the extra aminodeoxysugar subunit is important for biological activity.

No MeSH data available.


Related in: MedlinePlus

Neighbor-joining (NJ) tree of sponge and sediment associated actinomycetes based on partial sequence of 1400 base pairs of 16S rRNA genes. The tree was bootstrapped using 1000 replicates with the neighbor-joining algorithm. Scale bar = 0.01 nucleotide substitutions per site. Accession numbers of each sequence are indicated in parenthesis.
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marinedrugs-13-04682-f004: Neighbor-joining (NJ) tree of sponge and sediment associated actinomycetes based on partial sequence of 1400 base pairs of 16S rRNA genes. The tree was bootstrapped using 1000 replicates with the neighbor-joining algorithm. Scale bar = 0.01 nucleotide substitutions per site. Accession numbers of each sequence are indicated in parenthesis.

Mentions: The closest relative to Streptomyces sp. M7_15 searched through GenBank was Streptomyces sp. CNS-669-SD06 with a supporting 98% sequence homology of a partial sequence of the 16S rRNA gene (Figure 4). This suggests the possibility that Streptomyces sp. M7_15 is a new phylotype [23] with the ability to produce new compounds, and in fact six new compounds related to frigocylinone were isolated from the EtOAc extract of the fermentation broth (Figure 2). Since frigocyclinone was previously isolated from a Streptomyces griseus species associated with soils of Antarctica, its partial 16S rRNA sequence was used to compare its genomic information to the 16S rRNA gene of Streptomyces sp. M7_15. Intriguingly, when the neighbor-joining tree was analyzed, these two strains were grouped into two separate clusters, showing a significantly distant relationship to one another (Figure 4). Therefore, it could be assumed that Streptomyces sp. M7_15 is a new actinomycete phylotype that has evolved similar biosynthetic genes to the Antarctic strain of S. griseus or that the presence of the pathways leading to angucyclinone production in one or both strains resulted from horizontal transfer and the two pathways have a common ancestor [24,25,26]. Distinguishing these two possibilities would require sequencing both pathways.


Monacyclinones, New Angucyclinone Metabolites Isolated from Streptomyces sp. M7_15 Associated with the Puerto Rican Sponge Scopalina ruetzleri.

Vicente J, Stewart AK, van Wagoner RM, Elliott E, Bourdelais AJ, Wright JL - Mar Drugs (2015)

Neighbor-joining (NJ) tree of sponge and sediment associated actinomycetes based on partial sequence of 1400 base pairs of 16S rRNA genes. The tree was bootstrapped using 1000 replicates with the neighbor-joining algorithm. Scale bar = 0.01 nucleotide substitutions per site. Accession numbers of each sequence are indicated in parenthesis.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4556999&req=5

marinedrugs-13-04682-f004: Neighbor-joining (NJ) tree of sponge and sediment associated actinomycetes based on partial sequence of 1400 base pairs of 16S rRNA genes. The tree was bootstrapped using 1000 replicates with the neighbor-joining algorithm. Scale bar = 0.01 nucleotide substitutions per site. Accession numbers of each sequence are indicated in parenthesis.
Mentions: The closest relative to Streptomyces sp. M7_15 searched through GenBank was Streptomyces sp. CNS-669-SD06 with a supporting 98% sequence homology of a partial sequence of the 16S rRNA gene (Figure 4). This suggests the possibility that Streptomyces sp. M7_15 is a new phylotype [23] with the ability to produce new compounds, and in fact six new compounds related to frigocylinone were isolated from the EtOAc extract of the fermentation broth (Figure 2). Since frigocyclinone was previously isolated from a Streptomyces griseus species associated with soils of Antarctica, its partial 16S rRNA sequence was used to compare its genomic information to the 16S rRNA gene of Streptomyces sp. M7_15. Intriguingly, when the neighbor-joining tree was analyzed, these two strains were grouped into two separate clusters, showing a significantly distant relationship to one another (Figure 4). Therefore, it could be assumed that Streptomyces sp. M7_15 is a new actinomycete phylotype that has evolved similar biosynthetic genes to the Antarctic strain of S. griseus or that the presence of the pathways leading to angucyclinone production in one or both strains resulted from horizontal transfer and the two pathways have a common ancestor [24,25,26]. Distinguishing these two possibilities would require sequencing both pathways.

Bottom Line: Of these, monacyclinones A-B (4-5) contain the core ring structure of dehydrorabelomycin (2) with the aminodeoxysugar found in frigocyclinone (1).All structures were confirmed through spectral analyses.The strongest bioactivity against rhabdomycosarcoma cancer cells and gram-positive bacteria was exhibited by compound 9, suggesting that the extra aminodeoxysugar subunit is important for biological activity.

View Article: PubMed Central - PubMed

Affiliation: Center for Marine Science, University of North Carolina Wilmington, 5600 Marvin K. Moss Lane Wilmington, NC 28409, USA. jvicente@umces.edu.

ABSTRACT
During an investigation of new actinomycete species from Caribbean sponges for novel bioactive natural products, frigocyclinone (1), dimethyldehydrorabelomycin (3) and six new angucyclinone derivatives were isolated from Streptomyces sp. strain M7_15 associated with the sponge Scopalina ruetzleri. Of these, monacyclinones A-B (4-5) contain the core ring structure of dehydrorabelomycin (2) with the aminodeoxysugar found in frigocyclinone (1). Monacyclinone C (6) is a hydroxylated variant of frigocyclinone (1) and monacyclinone D (7) is a Baeyer Villiger derivative of (6) which also exists as the open chain hydrolysis product monacyclinone E (8). Monacyclinone F (9) contains two unique epoxide rings attached to the angucyclinone moiety and an additional aminodeoxysugar attached through an angular oxygen bond. All structures were confirmed through spectral analyses. Activity against rhabdomycosarcoma cancer cells (SJCRH30) after 48 h of treatment was observed with frigocyclinone (1; EC50 = 5.2 µM), monacyclinone C (6; 160 µM), monacyclinone E (8; 270 µM), and monacyclinone F (9; 0.73 µM). The strongest bioactivity against rhabdomycosarcoma cancer cells and gram-positive bacteria was exhibited by compound 9, suggesting that the extra aminodeoxysugar subunit is important for biological activity.

No MeSH data available.


Related in: MedlinePlus