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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

Monacyclinone derivatives isolated from Streptomyces sp. M7_15 including previously described frigocyclinone and dehydrorabelomycin.
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marinedrugs-13-04682-f002: Monacyclinone derivatives isolated from Streptomyces sp. M7_15 including previously described frigocyclinone and dehydrorabelomycin.

Mentions: Monacyclinone A (4, 4.3 mg) was isolated as a yellow powder and was calculated to have a molecular formula of C27H28NO5 ([M + H]+ observed: m/z 446.1974, calculated: m/z 446.1967, Δm = 1.6 ppm) as determined by HRESIMS, and corresponding to an additional double bond equivalent compared with 1 (Figure 2), and a possible loss of H2O. The UV spectrum of compound 4 in pyridine exhibited maximum absorbance at 280, 315, and 422 nm. Analysis of the 1H and 13C NMR spectral data for 4 (Table 1) showed many similarities with the chemical shift values corresponding to the frigocyclinone sugar moiety, which was attached to the aromatic nucleus at C-9 based on an HMBC correlation between H-1′ and C-9 (Figure 1 and Table S3). Resonances for the two pairs of aromatic protons on the B ring (H-5 δH 8.19 d, J = 8 Hz; H-6 δH 8.40 d, J = 8 Hz) and the D ring (H-10 δH 8.03 d, J = 8 Hz; H-11 δH 7.91 d, J = 8 Hz) were consistent with those observed in the 1H spectrum of 1 (Table 1, Figure 2). The chemical shifts of the A ring aromatic protons (H-2 δH 7.33 s; H-4 δH 7.28 s) were consistent with those of dehydrorabelomycin (2). The assignment of the relative configuration at carbons C-1′, C-4′, C-5′ was based on intense ROESY cross peaks between protons H-1′ (δH 5.26ax), H-3′ at (δH 1.98ax), and H-6′ at (δH 1.52ax) which positions these protons on the same side of the angucyclinone moiety (Table S3; Figure 3). Additionally, ROESY cross peaks between proton H-2′ax (δH 1.44) and H-4′ax at (δH 2.82) indicated diaxial interactions on the opposite face of the sugar ring (Figure 3).


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)

Monacyclinone derivatives isolated from Streptomyces sp. M7_15 including previously described frigocyclinone and dehydrorabelomycin.
© Copyright Policy
Related In: Results  -  Collection

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

marinedrugs-13-04682-f002: Monacyclinone derivatives isolated from Streptomyces sp. M7_15 including previously described frigocyclinone and dehydrorabelomycin.
Mentions: Monacyclinone A (4, 4.3 mg) was isolated as a yellow powder and was calculated to have a molecular formula of C27H28NO5 ([M + H]+ observed: m/z 446.1974, calculated: m/z 446.1967, Δm = 1.6 ppm) as determined by HRESIMS, and corresponding to an additional double bond equivalent compared with 1 (Figure 2), and a possible loss of H2O. The UV spectrum of compound 4 in pyridine exhibited maximum absorbance at 280, 315, and 422 nm. Analysis of the 1H and 13C NMR spectral data for 4 (Table 1) showed many similarities with the chemical shift values corresponding to the frigocyclinone sugar moiety, which was attached to the aromatic nucleus at C-9 based on an HMBC correlation between H-1′ and C-9 (Figure 1 and Table S3). Resonances for the two pairs of aromatic protons on the B ring (H-5 δH 8.19 d, J = 8 Hz; H-6 δH 8.40 d, J = 8 Hz) and the D ring (H-10 δH 8.03 d, J = 8 Hz; H-11 δH 7.91 d, J = 8 Hz) were consistent with those observed in the 1H spectrum of 1 (Table 1, Figure 2). The chemical shifts of the A ring aromatic protons (H-2 δH 7.33 s; H-4 δH 7.28 s) were consistent with those of dehydrorabelomycin (2). The assignment of the relative configuration at carbons C-1′, C-4′, C-5′ was based on intense ROESY cross peaks between protons H-1′ (δH 5.26ax), H-3′ at (δH 1.98ax), and H-6′ at (δH 1.52ax) which positions these protons on the same side of the angucyclinone moiety (Table S3; Figure 3). Additionally, ROESY cross peaks between proton H-2′ax (δH 1.44) and H-4′ax at (δH 2.82) indicated diaxial interactions on the opposite face of the sugar ring (Figure 3).

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