title: Two novel amphomycin analogues from Streptomyces canus strain FIM-0916.
abstract: Three lipopeptides, the known compound amphomycin, together with two novel compounds named aspartocin D (1) and aspartocin E (2) were obtained from the fermentation broth extraction of Streptomyces canus strain FIM0916 by using various column chromatography techniques. Their structures were elucidated by using spectroscopic methods, mainly by an extensive NMR analysis. It was demonstrated that compounds 1 and 2 are novel analogues of amphomycin, whose structures are similar to aspartocins. Compounds 1 and 2 share the same cyclic decapeptide core of cyclo (Dab2-Pip3-MeAsp4-Asp5-Gly6-Asp7-Gly8-Dab9-Val10-Pro11-), differing only in the side-chain moiety corresponding to Asp1-△3-isohendecenoic acid and Asp1-△3-isododecenoic acid, for aspartocin D and aspartocin E. In bioassays, compounds 1 and 2 exhibited antimicrobial activities against Gram-positive bacteria in the presence of Ca(2+) (1.25 mM); particularly, the activities were enhanced with higher concentrations of calcium.
authors.affiliation: a Department of Pharmaceutical Microbiology, Fujian Institute of Microbiology , Fuzhou 350007 , P.R. China.
authors.forename: Huang-Jian
authors.initials: HJ
authors.lastname: Yang
authors.forename: Xiao-Zhen
authors.initials: XZ
authors.lastname: Huang
authors.forename: Zhu-Lan
authors.initials: ZL
authors.lastname: Zhang
authors.forename: Chuan-Xi
authors.initials: CX
authors.lastname: Wang
authors.forename: Jian
authors.initials: J
authors.lastname: Zhou
authors.forename: Kai
authors.initials: K
authors.lastname: Huang
authors.forename: Jing-Ming
authors.initials: JM
authors.lastname: Zhou
authors.forename: Wei
authors.initials: W
authors.lastname: Zheng
mesh_terms: D000595:Amino Acid Sequence; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002118:Calcium / Q000737:chemistry; D006094:Gram-Positive Bacteria / Q000187:drug effects; D055666:Lipopeptides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D000900:Anti-Bacterial Agents; D055666:Lipopeptides; D010456:Peptides, Cyclic; C000592585:aspartocin D; C000592586:aspartocin E; C004423:amphomycin; D002118:Calcium
keywords: NMR spectroscopy; amphomycins; aspartocins; lipopeptide antibiotics; structure elucidation