PMID: 11908961Mar 23, 2002Paper

Cyclotheonamide E4 and E5, new potent tryptase inhibitors from an Ircinia species of sponge

Journal of Natural Products
Yasunobu MurakamiHiromi Fukamachi

Abstract

Tryptase is a protease released from mast cells and is believed to contribute to the inflammatory process in allergic diseases including asthma. In the course of screening to find tryptase inhibitors, we isolated two new tryptase inhibitors, cyclotheonamide E4 (3) and E5 (4), from a marine sponge of the genus Ircinia. The structures of these molecules were determined by interpretation of 1H and 13C NMR spectra, and they were shown to be closely related to the previously reported cyclotheonamides E (1), E2, and E3 (2). These molecules contain two unusual amino acids, vinylogous tyrosine and alpha-ketohomoarginine, which are involved in strong activities against serine proteases. Cyclotheonamide E4 showed potent inhibitory activity against human tryptase (IC50 5.1 nM). Therefore, cyclotheonamide E4 may be useful as a therapeutic agent in the treatment of allergic diseases including asthma.

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Citations

Mar 18, 2003·Bioorganic & Medicinal Chemistry Letters·George R Pettit, Rui Tan
Jul 28, 2005·Natural Product Reports·Roberto G S Berlinck, Miriam H Kossuga
Feb 3, 2009·Chemical & Pharmaceutical Bulletin·Rajiv DahiyaRajul Gupta
Feb 18, 2016·Chemical Reviews·Carmela De RisiVinicio Zanirato
Apr 28, 2006·The FEBS Journal·Jenny Hallgren, Gunnar Pejler
Jul 29, 2008·Angewandte Chemie·Stéphane P RocheDavid J Aitken
Jul 23, 2009·Chemistry & Biodiversity·Pt Kartikay Pandey
Jan 16, 2010·ChemMedChem·Norbert Schaschke, Christian P Sommerhoff
Sep 16, 2005·Molecular Carcinogenesis·Hye Joung ChoiNam Deuk Kim
Nov 8, 2013·Organic & Biomolecular Chemistry·Anne K SchoonenBen L Feringa
Aug 1, 2020·Marine Drugs·Rogelio FernándezMasteria Yunovilsa Putra
Jan 3, 2021·International Journal of Biological Macromolecules·Noora BarzkarReza Nahavandi
Sep 30, 2017·Journal of the American Chemical Society·Mamen Rodríguez-FernándezSyuzanna R Harutyunyan
Mar 17, 2007·Journal of Natural Products·Yoichi Nakao, Nobuhiro Fusetani
May 10, 2006·Biochemistry·Mary E McGrathBradley A Katz

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