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Open AccessArticle

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

Center for Marine Science, University of North Carolina Wilmington, 5600 Marvin K. Moss Lane Wilmington, NC 28409, USA
Institute of Marine and Environmental Technology, Center for Environmental Science, University of Maryland, 701 E Pratt St Suite 236, Baltimore, MD 21202, USA
Author to whom correspondence should be addressed.
Academic Editor: Valeria Costantino
Mar. Drugs 2015, 13(8), 4682-4700;
Received: 24 April 2015 / Revised: 29 June 2015 / Accepted: 2 July 2015 / Published: 29 July 2015
(This article belongs to the Special Issue Marine Secondary Metabolites)
PDF [425 KB, uploaded 29 July 2015]


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 (45) 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. View Full-Text
Keywords: angucyclinone; Streptomyces; antibiotic; anticancer angucyclinone; Streptomyces; antibiotic; anticancer

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Vicente, J.; Stewart, A.K.; Van Wagoner, R.M.; Elliott, E.; Bourdelais, A.J.; Wright, J.L.C. Monacyclinones, New Angucyclinone Metabolites Isolated from Streptomyces sp. M7_15 Associated with the Puerto Rican Sponge Scopalina ruetzleri. Mar. Drugs 2015, 13, 4682-4700.

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