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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

Key 1H–1H COSY and HMBC correlations of compounds 4–9.
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marinedrugs-13-04682-f001: Key 1H–1H COSY and HMBC correlations of compounds 4–9.

Mentions: Angucyclinone natural products have been isolated from a variety of actinobacteria since the discovery of tetrangomycin and tetrangulol in the 1960s, and congeners of this increasingly diverse natural product class have exhibited intriguing activity profiles [10,11,18]. Frigocyclinone (1) was the first angucyclinone derivative to have a C-glycosidic linked aminodeoxy sugar moiety (Figure 1). In this study we report six related derivatives, called the monacyclinones, which contain similar features to frigocyclinone including the characteristic C-glycosidic aminodeoxy sugar moiety. Significantly, the wild-type strain also produces monacyclinone D (7) in which the A ring is found as a lactone moiety, which most likely arises by a Baeyer-Villiger reaction. In addition, this compound co-occurs with the open chain hydrolysis product monacyclinone E (8). Monacyclinone F (9) contains two epoxide rings attached to the angucyclinone moiety and an additional aminodeoxysugar unit, but this time attached by an ether linkage (Figure 1). These novel compounds displayed biological activity against human rhabdomyosarcoma cancer cells (SJCRH30) and gram-positive bacteria.


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)

Key 1H–1H COSY and HMBC correlations of compounds 4–9.
© Copyright Policy
Related In: Results  -  Collection

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

marinedrugs-13-04682-f001: Key 1H–1H COSY and HMBC correlations of compounds 4–9.
Mentions: Angucyclinone natural products have been isolated from a variety of actinobacteria since the discovery of tetrangomycin and tetrangulol in the 1960s, and congeners of this increasingly diverse natural product class have exhibited intriguing activity profiles [10,11,18]. Frigocyclinone (1) was the first angucyclinone derivative to have a C-glycosidic linked aminodeoxy sugar moiety (Figure 1). In this study we report six related derivatives, called the monacyclinones, which contain similar features to frigocyclinone including the characteristic C-glycosidic aminodeoxy sugar moiety. Significantly, the wild-type strain also produces monacyclinone D (7) in which the A ring is found as a lactone moiety, which most likely arises by a Baeyer-Villiger reaction. In addition, this compound co-occurs with the open chain hydrolysis product monacyclinone E (8). Monacyclinone F (9) contains two epoxide rings attached to the angucyclinone moiety and an additional aminodeoxysugar unit, but this time attached by an ether linkage (Figure 1). These novel compounds displayed biological activity against human rhabdomyosarcoma cancer cells (SJCRH30) and gram-positive bacteria.

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