Melophlins C-O, thirteen novel tetramic acids from the marine sponge Melophlus sarassinorum.
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.
Wang
Chang-Yun
CY
Institut für Pharmazeutische Biologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, Geb. 26.23, D-40225 Düsseldorf, Germany.
Wang
Bin-Gui
BG
Wiryowidagdo
Sumali
S
Wray
Victor
V
van Soest
Rob
R
Steube
Klaus G
KG
Guan
Hua-Shi
HS
Proksch
Peter
P
Ebel
Rainer
R
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
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D011760:Pyrrolidinones; C009435:tetramic acid