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Pagoamide A, a cyclic depsipeptide isolated from a cultured marine chlorophyte, Derbesia sp., using MS/MS-based molecular networking

TitlePagoamide A, a cyclic depsipeptide isolated from a cultured marine chlorophyte, Derbesia sp., using MS/MS-based molecular networking
Publication TypeJournal Article
Year of Publication2020
AuthorsLi Y.Y, Yu H.B, Zhang Y., Leao T., Glukhov E., Pierce M.L, Zhang C., Kim H, Mao H.H, Fang F., Cottrell G.W, Murray T.F, Gerwick L, Guan H.S, Gerwick WH
Volume83
Pagination617-625
Date Published2020/03
Type of ArticleArticle
ISBN Number0163-3864
Accession NumberWOS:000526306000008
Keywordsamino-acid-analysis; analogs; cyclodepsipeptides; kahalalide-f; marfeys reagent; mass-spectrometry; mollusk elysia-rufescens; natural-products; new-guinea collection; peptide; Pharmacology & Pharmacy; Plant Sciences
Abstract

A thiazole-containing cyclic depsipeptide with 11 amino acid residues, named pagoamide A (1), was isolated from laboratory cultures of a marine Chlorophyte, Derbesia sp. This green algal sample was collected from America Samoa, and pagoamide A was isolated using guidance by MS/MS-based molecular networking. Cultures were grown in a light- and temperature-controlled environment and harvested after several months of growth. The planar structure of pagoamide A (1) was characterized by detailed 1D and 2D NMR experiments along with MS and UV analysis. The absolute configurations of its amino acid residues were determined by advanced Marfey's analysis following chemical hydrolysis and hydrazinolysis reactions. Two of the residues in pagoamide A (1), phenylalanine and serine, each occurred twice in the molecule, once in the D- and once in the L-configuration. The biosynthetic origin of pagoamide A (1) was considered in light of other natural products investigations with coenocytic green algae.

DOI10.1021/acs.jnatprod.9b01019
Student Publication: 
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