Abstract
Chemical investigation of the secondary metabolites of a rare New Zealand deep-sea sponge, Lamellomorpha strongylata, resulted in the isolation of twenty-one indole alkaloids, including two new bisindoles—(Z)-coscinamide D (1), (E)-coscinamide D (2)—and four compounds isolated for the first time as natural products—lamellomorphamides A (3), B (4), C (5) and D (6). In addition, fifteen previously reported natural products were isolated, seven of which are seco analogs of hamacanthin alkaloids. The one sponge produces enantiomerically pure but opposite configurations of compounds that only differ in the number of bromines, suggesting enantiodivergent biosynthesis. In addition, four compounds were isolated as partial racemates, suggesting these compounds are biosynthesized via two independent routes.
Highlights
In our continuing exploration of marine sponges as sources of novel brominated alkaloids [1,2,3], we investigated a New Zealand deep-sea sponge collected from the western continental slope
We report the isolation of four new bisindole alkaloids, as well as seventeen other indole alkaloids, from L. strongylata
Lamellomorphamides A–D (3–4) were isolated for the first time as natural products, they were previously reported as intermediates in the synthesis of 60,600 -didebromo-cis-3,4-dihydrohamacanthin
Summary
In our continuing exploration of marine sponges as sources of novel brominated alkaloids [1,2,3], we investigated a New Zealand deep-sea sponge collected from the western continental slope. There are only two reports of natural products from the genus Lamellomorpha, both from New. Zealand from the same 1995 collection from the Chatham Rise, off the east coast of the South Island. Bioassay-guided separation of the extracts from that collection resulted in the isolation of three distinct classes of cytotoxic polyketides: calyculins (calyculins A, B, E, F, and calyculinamides A and B), swinholide H, and theonellapeptolide IIIe [5,6]. Our collection of the same species yielded no polyketides, rather indole alkaloids. We report the isolation of four new bisindole alkaloids, as well as seventeen other indole alkaloids, from L. strongylata
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