Mollecarbamates, Molleureas, and Molledihydroisoquinolone, o-Carboxyphenethylamide Metabolites of the Ascidian Didemnum molle Collected in Madagascar

Michal Issac, Maurice Aknin, Anne Gauvin-Bialecki, Christopher D. Pond, Louis R. Barrows, Yoel Kashman, Shmuel Carmeli

Research output: Contribution to journalArticlepeer-review

Abstract

The extract of a sample of the tunicate Didemnum molle (MAY13-117) collected in Mayotte afforded eight new metabolites, mollecarbamates A-D (1-4) and molleureas B-E (5-8), along with the two known natural products, N,N′-diphenylethyl urea (10) and molleurea A (11). Another sample of D. molle (MAD11-BA065) collected in Baie des Assassins, Madagascar, afforded molledihydroisoquinolone (9). Mollecarbamates 1-4 are a family of compounds that possess repeating o-carboxyphenethylamide units and a carbamate moiety, while the molleureas 5-8 contain tetra-and penta-repeating carboxyphenethylamide units and a urea bridge in different positions. Molledihydroisoquinolone (9) is a cyclic form of o-carboxyphenethylamide. We propose that these unique natural products are most probably produced by an unprecedented biosynthetic pathway that contains a yet unknown chorismate mutase variant. The structures of the compounds were elucidated by interpretation of the data from 1D and 2D NMR, HRESIMS, and MS/MS analyses of the positive ESIMS experiments. Compounds 1-8 were tested against pathogenic bacteria and in a cytoprotective HIV cell based assay but did not show any significant effects in these assays.

Original languageEnglish
Pages (from-to)1844-1852
Number of pages9
JournalJournal of Natural Products
Volume80
Issue number6
DOIs
StatePublished - 23 Jun 2017

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