Pagoamide A, a Cyclic Depsipeptide Isolated from a Cultured Marine Chlorophyte, Derbesia sp., Using MS/MS-Based Molecular Networking

Yueying Li, Hao Bing Yu, Yi Zhang, Tiago Leao, Evgenia Glukhov, Marsha L. Pierce, Chen Zhang, Hyunwoo Kim, Huanru Henry Mao, Fang Fang, Garrison W. Cottrell, Thomas F. Murray, Lena Gerwick, Huashi Guan, William H. Gerwick

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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.

Original languageEnglish (US)
Pages (from-to)617-625
Number of pages9
JournalJournal of Natural Products
Volume83
Issue number3
DOIs
StatePublished - Mar 27 2020

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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    Li, 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., & Gerwick, W. H. (2020). Pagoamide A, a Cyclic Depsipeptide Isolated from a Cultured Marine Chlorophyte, Derbesia sp., Using MS/MS-Based Molecular Networking. Journal of Natural Products, 83(3), 617-625. https://doi.org/10.1021/acs.jnatprod.9b01019