Sceliphrolactam, a polyene macrocyclic lactam from a wasp-associated Streptomyces sp.
A previously unreported 26-membered polyene macrocyclic lactam, sceliphrolactam, was isolated from an actinomycete, Streptomyces sp., associated with the mud dauber, Sceliphron caementarium. Sceliphrolactam's structure was determined by 1D- and 2D-NMR, MS, UV, and IR spectral analysis. Sceliphrolactam displays antifungal activity against amphotericin B-resistant Candida albicans (MIC = 4 μg/mL, 8.3 μM).
Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, Boston, Massachusetts 02115, USA.
Dong-Chan
DC
Oh
Michael
M
Poulsen
Cameron R
CR
Currie
Jon
J
Clardy
D000666:Amphotericin B / Q000494:pharmacology; D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D047029:Lactams, Macrocyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D019906:Nuclear Magnetic Resonance, Biomolecular; D011090:Polyenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013302:Streptomyces / Q000737:chemistry*; D014863:Wasps / Q000382:microbiology*
D000935:Antifungal Agents; D047029:Lactams, Macrocyclic; D011090:Polyenes; C556704:sceliphrolactam; D000666:Amphotericin B
Chem Biodivers. 2004 Apr;1(4):640-5
17191875
J Antibiot (Tokyo). 2005 Jan;58(1):1-26
15813176
Proc Natl Acad Sci U S A. 2010 Jun 29;107(26):11692-7
20547882
PLoS One. 2011 Feb 22;6(2):e16763
21364940
Nat Chem Biol. 2009 Jun;5(6):391-3
19330011
Nat Chem Biol. 2010 Apr;6(4):261-3
20190763
Science. 2008 Oct 3;322(5898):63
18832638
Org Lett. 2009 Feb 5;11(3):633-6
19125624
Curr Biol. 2005 Mar 8;15(5):475-9
15753044
Proc Natl Acad Sci U S A. 2009 Mar 24;106(12):4742-6
19270078
Proc Natl Acad Sci U S A. 2007 Jun 19;104(25):10376-81
17563368