New benzoxazine secondary metabolites from an arctic actinomycete

Two new secondary metabolites, arcticoside (1) and C-1027 chromophore-V (2), were isolated along with C-1027 chromophore-III and fijiolides A and B (3-5) from a culture of an Arctic marine actinomycete Streptomyces strain. The chemical structures of 1 and 2 were elucidated through NMR, mass, UV, and...

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Veröffentlicht in:	Marine drugs 2014-04, Vol.12 (5), p.2526-2538
Hauptverfasser:	Moon, Kyuho, Ahn, Chan-Hong, Shin, Yoonho, Won, Tae Hyung, Ko, Keebeom, Lee, Sang Kook, Oh, Ki-Bong, Shin, Jongheon, Nam, Seung-Il, Oh, Dong-Chan
Format:	Artikel
Sprache:	eng
Schlagworte:	Antifungal Agents - pharmacology Antineoplastic Agents - pharmacology Arctic Arctic Regions benzoxazine Benzoxazines - chemistry Benzoxazines - metabolism Benzoxazines - pharmacology C-1027 Candida albicans Candida albicans - drug effects Cell Line, Tumor Cell Proliferation disaccharide fijiolides Hexoses - chemistry Humans isocitrate lyase Marine marine actinomycete secondary metabolite Streptomyces Streptomyces - chemistry
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Zusammenfassung:	Two new secondary metabolites, arcticoside (1) and C-1027 chromophore-V (2), were isolated along with C-1027 chromophore-III and fijiolides A and B (3-5) from a culture of an Arctic marine actinomycete Streptomyces strain. The chemical structures of 1 and 2 were elucidated through NMR, mass, UV, and IR spectroscopy. The hexose moieties in 1 were determined to be d-glucose from a combination of acid hydrolysis, derivatization, and gas chromatographic analyses. Arcticoside (1) and C-1027 chromophore-V (2), which have a benzoxazine ring, inhibited Candida albicans isocitrate lyase. Chromophore-V (2) exhibited significant cytotoxicity against breast carcinoma MDA-MB231 cells and colorectal carcinoma cells (line HCT-116), with IC₅₀ values of 0.9 and 2.7 μM, respectively.
ISSN:	1660-3397 1660-3397
DOI:	10.3390/md12052526