Euthyroideones, Novel Brominated Quinone Methides from the Bryozoan Euthyroides episcopalis

The Journal of Organic Chemistry
1998.0

Abstract

Although comparatively little research has been undertaken into bryozoan secondary metabolites as compared with those of other marine invertebrates, bryozoans have proven to be an excellent source of novel and/or biologically active compounds, with the majority of isolated metabolites being alkaloids. In a continuing survey of the chemical composition of New Zealand marine bryozoans, an extract of Euthyroides episcopalis was investigated. Three novel alkaloids, euthyroideones A-C (1-3), were isolated via MeOH/CH₂Cl₂ extraction, reversed-phase flash column chromatography, gel permeation chromatography, and HPLC. The structures were elucidated using HREIMS, NMR (HMQC, HMBC), and X-ray crystallography (for euthyroideone A), revealing a pyrido[4,3-h]-1,4-benzothiazine skeleton for euthyroideone A, a double bond between C2 and C3 for euthyroideone B, and a 7,8-dehydro structure for euthyroideone C. Biological assays (P388 murine leukemia, antiviral/cytotoxicity) showed no significant activity for most compounds, except euthyroideone B, which exhibited weak cytotoxicity to BSC-1 cells.

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