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

Organic Letters
Celso AlmeidaGabriele M König

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.

References

Nov 24, 2006·Applied and Environmental Microbiology·Laila P Partida-MartinezChristian Hertweck
Feb 20, 2010·Current Topics in Medicinal Chemistry·José BreaMaría Isabel Loza
Aug 26, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sivatharushan Sivanathan, Jürgen Scherkenbeck

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Citations

Dec 1, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xiaohan WangLigang Zhou
Sep 6, 2017·Organic & Biomolecular Chemistry·Lena BarraJeroen S Dickschat
Oct 11, 2019·Medicinal Research Reviews·Xiaoshu Jing, Kang Jin
Feb 23, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mei-Mei ChengGuo-Qiang Li

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