title: Monacyclinones, New Angucyclinone Metabolites Isolated from Streptomyces sp. M7_15 Associated with the Puerto Rican Sponge Scopalina ruetzleri.
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.
authors.affiliation: Center for Marine Science, University of North Carolina Wilmington, 5600 Marvin K. Moss Lane Wilmington, NC 28409, USA. jvicente@umces.edu.|Institute of Marine and Environmental Technology, Center for Environmental Science, University of Maryland, 701 E Pratt St Suite 236, Baltimore, MD 21202, USA. jvicente@umces.edu.
authors.forename: Jan
authors.initials: J
authors.lastname: Vicente
authors.affiliation: Center for Marine Science, University of North Carolina Wilmington, 5600 Marvin K. Moss Lane Wilmington, NC 28409, USA. stewarta@uncw.edu.
authors.forename: Allison K
authors.initials: AK
authors.lastname: Stewart
authors.affiliation: Center for Marine Science, University of North Carolina Wilmington, 5600 Marvin K. Moss Lane Wilmington, NC 28409, USA. r.m.vanwagoner@pham.utah.edu.
authors.forename: Ryan M
authors.initials: RM
authors.lastname: van Wagoner
authors.affiliation: Center for Marine Science, University of North Carolina Wilmington, 5600 Marvin K. Moss Lane Wilmington, NC 28409, USA. elliotte@uncw.edu.
authors.forename: Elizabeth
authors.initials: E
authors.lastname: Elliott
authors.affiliation: Center for Marine Science, University of North Carolina Wilmington, 5600 Marvin K. Moss Lane Wilmington, NC 28409, USA. bourdelaisa@uncw.edu.
authors.forename: Andrea J
authors.initials: AJ
authors.lastname: Bourdelais
authors.affiliation: Center for Marine Science, University of North Carolina Wilmington, 5600 Marvin K. Moss Lane Wilmington, NC 28409, USA. wrightj@uncw.edu.
authors.forename: Jeffrey L C
authors.initials: JL
authors.lastname: Wright
mesh_terms: D000818:Animals; D000880:Anthraquinones / Q000737:chemistry* / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000737:chemistry / Q000494:pharmacology; D017691:Caribbean Region; D045744:Cell Line, Tumor; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006801:Humans; D011161:Porifera / Q000382:microbiology*; D011647:Puerto Rico; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D001688:Biological Products; C510997:angucyclinone; C502980:frigocyclinone
keywords: Streptomyces; angucyclinone; antibiotic; anticancer