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Endolides A and B, Vasopressin and Serotonin-Receptor Interacting N-Methylated Peptides from the Sponge-Derived Fungus Stachylidium sp.

Author:
Almeida, Celso, Maddah, Fayrouz El, Kehraus, Stefan, Schnakenburg, Gregor, König, Gabriele M.
Source:
Organic letters 2016 v.18 no.3 pp. 528-531
ISSN:
1523-7052
Subject:
Stachylidium, amino acids, chemical reactions, chemical structure, fungi, organic compounds, serotonin receptors, vasopressin, vasopressin receptors
Abstract:
The marine-derived fungus Stachylidium sp. was isolated from the sponge Callyspongia sp. cf. C. flammea. Culture on a biomalt medium supplemented with sea salt led to the isolation of two new, most unusual N-methylated peptides, i.e., the tetrapeptides endolide A and B (1 and 2). Both of these contain the very rare amino acid 3-(3-furyl)-alanine. In radioligand binding assays endolide A (1) showed affinity to the vasopressin receptor 1A with a Kᵢ of 7.04 μM, whereas endolide B (2) exhibited no affinity to the latter receptor, but was selective toward the serotonin receptor 5HT₂b with a Kᵢ of 0.77 μM.
Agid:
5792304