Novel caprolactones from a marine streptomycete.
Two new caprolactones, (R)-10-methyl-6-undecanolide (1) and (6R,10S)-10-methyl-6-dodecanolide (2), were identified in the lipid extract of a marine streptomycete (isolate B6007). Their structures were proposed on the basis of GC-MS experiments and proved by synthesis. The absolute configuration of the compounds was established by comparison of the natural and synthetic stereoisomers using chiral gas chromatography. These caprolactones show a moderate phytotoxicity and a promising activity against cancer cells with concomitant low general cytotoxicity.
Stritzke
Katja
K
Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106 Braunschweig, Germany.
Schulz
Stefan
S
Laatsch
Hartmut
H
Helmke
Elisabeth
E
Beil
Winfried
W
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D008401:Gas Chromatography-Mass Spectrometry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008386:Marine Biology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010219:Papua New Guinea; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
C484823:(6R,10S)-10-methyl-6-dodecanolide; C484822:(R)-10-methyl-6-undecanolide; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D007783:Lactones