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Mar. Drugs 2015, 13(8), 4682-4700; doi:10.3390/md13084682

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

1
Center for Marine Science, University of North Carolina Wilmington, 5600 Marvin K. Moss Lane Wilmington, NC 28409, USA
2
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
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)
View Full-Text   |   Download PDF [425 KB, uploaded 29 July 2015]   |  

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 (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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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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