Swinhoeiamide A, a new highly active calyculin derivative from the marine sponge Theonella swinhoei.
Analysis of the Papua New Guinean sponge Theonella swinhoei afforded a new calyculinamide-related congener for which we propose the name swinhoeiamide A (1). The structure of the new compound was unambiguously established on the basis of NMR spectroscopic ((1)H, (13)C, COSY, HMBC) and mass spectrometric (FABMS) data. Swinhoeiamide A exhibited insecticidal activity toward neonate larvae of the polyphagous pest insect Spodoptera littoralis when incorporated in an artificial diet offered to the larvae in a chronic feeding bioassay (ED(50) 2.11 ppm, LD(50) 2.98 ppm). Furthermore, it was found to be fungicidal against Candida albicans and Aspergillus fumigatus (MIC 1.2 and 1.0 microg/mL, respectively).
Edrada
Ru Angelie
RA
Institut für Pharmazeutische Biologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, Geb. 26.23, Germany.
Ebel
Rainer
R
Supriyono
Agus
A
Wray
Victor
V
Schupp
Peter
P
Steube
Klaus
K
van Soest
Rob
R
Proksch
Peter
P
D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001232:Aspergillus fumigatus / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D005247:Feeding Behavior / Q000187:drug effects; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007814:Larva / Q000187:drug effects; D015394:Molecular Structure; D010755:Organophosphates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010080:Oxazoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010219:Papua New Guinea; D011161:Porifera / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D018411:Spodoptera / Q000187:drug effects; D013172:Spores, Fungal / Q000187:drug effects
D000935:Antifungal Agents; D007306:Insecticides; D010755:Organophosphates; D010080:Oxazoles; C466372:calyculinamide A; C404954:clavosine A; C466371:swinhoeiamide A