title: Melophlins C-O, thirteen novel tetramic acids from the marine sponge Melophlus sarassinorum.
abstract: Thirteen new metabolites, melophlins C-O (1-13), were identified from the marine sponge Melophlus sarassinorum. Compounds 1-13 represent tetramic acid derivatives that differ with regard to the nature of their alkyl side chains. The structures of the new compounds were elucidated on the basis of comprehensive spectral analysis (1H, 13C, 1H-1H COSY, HMQC, and HMBC NMR, as well as low- and high-resolution ESIMS and EIMS). The absolute configurations of 1, 8, 10, 11, 12, and 13 were determined by ESI LC/MS analysis of chiral derivatives obtained upon oxidation and hydrolysis of the respective parent compounds. Melophlin C (1) displayed pronounced antibacterial activity against Bacillus subtilisand Staphylococcus aureus, together with antifungal activity against Candida albicans.
authors.affiliation: Institut für Pharmazeutische Biologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, Geb. 26.23, D-40225 Düsseldorf, Germany.
authors.forename: Chang-Yun
authors.initials: CY
authors.lastname: Wang
authors.forename: Bin-Gui
authors.initials: BG
authors.lastname: Wang
authors.forename: Sumali
authors.initials: S
authors.lastname: Wiryowidagdo
authors.forename: Victor
authors.initials: V
authors.lastname: Wray
authors.forename: Rob
authors.initials: R
authors.lastname: van Soest
authors.forename: Klaus G
authors.initials: KG
authors.lastname: Steube
authors.forename: Hua-Shi
authors.initials: HS
authors.lastname: Guan
authors.forename: Peter
authors.initials: P
authors.lastname: Proksch
authors.forename: Rainer
authors.initials: R
authors.lastname: Ebel
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D006141:Guam; D006868:Hydrolysis; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011161:Porifera / Q000737:chemistry*; D011760:Pyrrolidinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D013211:Staphylococcus aureus / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D011760:Pyrrolidinones; C009435:tetramic acid