T-muurolol sesquiterpenes from the marine Streptomyces sp. M491 and revision of the configuration of previously reported amorphanes.
Two new sesquiterpenes, 15-hydroxy-T-muurolol (3d) and 11,15-dihydroxy-T-muurolol (3e), along with the plant cadinenes T-muurolol (3f) and 3alpha-hydroxy-T-muurolol (3g), were isolated from the marine-derived Streptomyces sp. M491. Their absolute configuration was established via NMR spectroscopy and X-ray crystallography of 3-oxo-T-muurolol (3a), which was reisolated from this strain. In addition, the absolute configuration of further sesquiterpenes previously reported from this strain was revised. These products were tested for their cytotoxicity against 37 human tumor cell lines using the MTT method. Only 3d was cytotoxic against a range of human tumor cell lines with a mean IC50 of 6.7 microg/mL.
Ding
Ling
L
Department of Organic and Biomolecular Chemistry, University of Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany.
Pfoh
Roland
R
Rühl
Stephan
S
Qin
Song
S
Laatsch
Hartmut
H
D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008386:Marine Biology; D008968:Molecular Conformation; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D013302:Streptomyces / Q000737:chemistry*
C535095:11,15-dihydroxy-T-muurolol; C535094:15-hydroxy-T-muurolol; D000970:Antineoplastic Agents; D012717:Sesquiterpenes