Neopetromin, a Cyclic Tripeptide with a C-N Cross-Link, from the Marine Sponge Neopetrosia sp., That Causes Vacuole Fragmentation in Tobacco BY-2 Cells

  • J Nat Prod. 2024 Mar 19. doi: 10.1021/acs.jnatprod.4c00158.
Yuki Hitora  1 ,  Ahmed H El-Desoky  2 ,  Yusaku Sadahiro  1 ,  Ai Sejiyama  1 ,  Amiri Kinoshita  3 ,  Yuji Ise  4 ,  Esther D Angkouw  5 ,  Remy E P Mangindaan  5 ,  Takumi Higaki  3  6 ,  Sachiko Tsukamoto  1
Affiliations
  • 1. Department of Natural Medicines, Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan.
  • 2. Pharmaceutical and Drug Industries Research Institute, Pharmacognosy Department, National Research Centre, 33 El-Bohouth Street, Dokki, Giza 12622, Egypt.
  • 3. Faculty of Science, Kumamoto University, Kurokami, Chuo-ku, Kumamoto 860-8555 Japan.
  • 4. Kuroshio Biological Research Foundation, 560 Nishidomari, Otsuki, Hata, Kochi 788-0333, Japan.
  • 5. Faculty of Fisheries and Marine Science, Sam Ratulangi University, Kampus Bahu, Manado 95115, Indonesia.
  • 6. International Research Organization for Advanced Science and Technology, Kumamoto University, Kurokami, Chuo-ku, Kumamoto 860-8555 Japan.
PMID: 38503712 DOI: 10.1021/acs.jnatprod.4c00158
Abstract

HPLC-MS analysis revealed the presence of an unreported peptide in the extract of the marine Sponge Neopetrosia sp. Its structure was determined as a tripeptide, named neopetromin (1), composed of two tyrosine and one tryptophan residues with a heteroaromatic C-N cross-link between side chains. The absolute configuration of Amino acids was determined using Marfey's method after ozonolysis and hydrolysis of 1. Compound 1 promoted vacuole fragmentation in an actin-independent manner in tobacco BY-2 cells.

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