Structures and Antibacterial Activities of Minor Dolabellanes from the Brown Alga Dilophus spiralis

Thirteen new minor diterpenes featuring the dolabellane skeleton (1–13) were isolated from the organic extracts of the brown alga Dilophus spiralis, collected in Elafonissos Island. The structures and relative configurations of the isolated natural products were elucidated on the basis of extensive...

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Published in:European journal of organic chemistry 2012-09, Vol.2012 (27), p.5177-5186
Main Authors: Ioannou, Efstathia, Quesada, Antonio, Rahman, M. Mukhlesur, Gibbons, Simon, Vagias, Constantinos, Roussis, Vassilios
Format: Article
Language:English
Subjects:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological activity
Biological and medical sciences
Chemistry
Dilophus spiralis
Dolabellanes
Exact sciences and technology
General pharmacology
Medical sciences
Natural products
Organic chemistry
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Preparations and properties
Staphylococcus aureus
Structure elucidation
Terpenoids
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Summary:Thirteen new minor diterpenes featuring the dolabellane skeleton (1–13) were isolated from the organic extracts of the brown alga Dilophus spiralis, collected in Elafonissos Island. The structures and relative configurations of the isolated natural products were elucidated on the basis of extensive analyses of their spectroscopic data (NMR, MS, IR). The absolute configuration of 1 was determined by using the modified Mosher's method, whereas the structure of 2 was confirmed by single‐crystal X‐ray diffraction analysis. The antibacterial activities of metabolites 1–9 and 13 were evaluated against six strains of Staphylococcus aureus, including multidrug‐ and methicillin‐resistant variants. Compounds 1 and 4 exhibited noteworthy levels of activity with MIC values in the range of 2–8 μg/mL. Thirteen new minor dolabellane diterpenes (1–13) were isolated from the brown alga Dilophus spiralis. Their structures were established through analyses of their spectroscopic data. Compounds 1 and 4 exhibited comparable to 64‐fold stronger activities than the standard antibiotic norfloxacin against one methicillin‐resistant and two multidrug‐resistant effluxing Staphylococcus aureus strains.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201200533