Online analysis of xestodecalactones A-C, novel bioactive metabolites from the fungus Penicillium cf. montanense and their subsequent isolation from the sponge Xestospongia exigua.
Fungal isolates of Penicillium cf. montanense were obtained from the marine sponge Xestospongia exiguacollected from the Bali Sea, Indonesia. Culture filtrates of the fungi yielded three novel decalactone metabolites, xestodecalactones A, B, and C (1, 2a, and 2b), consisting of 10-membered macrolides with a fused 1,3-dihydroxybenzene ring. Online HPLC-NMR, ESI-MS/MS, and -CD spectra were acquired, and the structures of the new compounds were established and confirmed on the basis of offline NMR spectroscopic ((1)H, (13)C, COSY, ROESY, (1)H-detected direct and long-range (13)C-(1)H correlations) and mass spectrometric (EIMS) data. Quantum chemical calculations of the CD spectra proved to be difficult because of the conformational flexibility of the xestodecalactones. These compounds, of which 2a and 2b, due to the additional stereocenter at C-9, are diastereomeric compounds, are structurally related to a number of biologically active metabolites found in terrestrial fungal strains. Compound 2a was found to be active against the yeast Candida albicans.
Edrada
Ru Angelie
RA
Institut für Pharmazeutische Biologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1 Geb 26.23, D-40225 Düsseldorf, Germany.
Heubes
Markus
M
Brauers
Gernot
G
Wray
Victor
V
Berg
Albrecht
A
Grafe
Udo
U
Wohlfarth
Michael
M
Muhlbacher
Jorg
J
Schaumann
Karsten
K
Sudarsono
Sudarsono
S
Bringmann
Gerhard
G
Proksch
Peter
P
D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D004578:Electron Spin Resonance Spectroscopy; D007214:Indonesia; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008968:Molecular Conformation; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry*; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism
D000935:Antifungal Agents; D007783:Lactones; C471496:xestodecalactone A; C471497:xestodecalactone B; C471498:xestodecalactone C