Enigmazole C: A Cytotoxic Macrocyclic Lactone and Its Ring-Opened Derivatives from a New Species of Homophymia Sponge

[Image: see text] A new macrolide, enigmazole C (1), and two additional analogues, enigmazoles E (2) and D (3), were obtained from a new species of the Homophymia genus as part of an ongoing discovery program at PharmaMar to study cytotoxic substances from marine sources. The structures were fully c...

Descripción completa

Detalles Bibliográficos
Autores principales: Tarazona, Guillermo, Fernández, Rogelio, Pérez, Marta, Millán, Ramón E., Jiménez, Carlos, Rodríguez, Jaime, Cuevas, Carmen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society and American Society of Pharmacognosy 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9040057/
https://www.ncbi.nlm.nih.gov/pubmed/35234467
http://dx.doi.org/10.1021/acs.jnatprod.1c01179
_version_ 1784694261120237568
author Tarazona, Guillermo
Fernández, Rogelio
Pérez, Marta
Millán, Ramón E.
Jiménez, Carlos
Rodríguez, Jaime
Cuevas, Carmen
author_facet Tarazona, Guillermo
Fernández, Rogelio
Pérez, Marta
Millán, Ramón E.
Jiménez, Carlos
Rodríguez, Jaime
Cuevas, Carmen
author_sort Tarazona, Guillermo
collection PubMed
description [Image: see text] A new macrolide, enigmazole C (1), and two additional analogues, enigmazoles E (2) and D (3), were obtained from a new species of the Homophymia genus as part of an ongoing discovery program at PharmaMar to study cytotoxic substances from marine sources. The structures were fully characterized by cumulative analyses of NMR, IR, and MS spectra, along with density functional theory computational calculations. All three of the new compounds feature an unusual 2,3-dihydro-4H-pyran-4-one moiety, but only enigmazoles C (1) and D (3) showed cytotoxic activity in the micromolar range against A-549 (lung), HT-29 (colon), MDA-MB-231 (breast), and PSN-1 (pancreas) tumor cells.
format Online
Article
Text
id pubmed-9040057
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society and American Society of Pharmacognosy
record_format MEDLINE/PubMed
spelling pubmed-90400572022-04-27 Enigmazole C: A Cytotoxic Macrocyclic Lactone and Its Ring-Opened Derivatives from a New Species of Homophymia Sponge Tarazona, Guillermo Fernández, Rogelio Pérez, Marta Millán, Ramón E. Jiménez, Carlos Rodríguez, Jaime Cuevas, Carmen J Nat Prod [Image: see text] A new macrolide, enigmazole C (1), and two additional analogues, enigmazoles E (2) and D (3), were obtained from a new species of the Homophymia genus as part of an ongoing discovery program at PharmaMar to study cytotoxic substances from marine sources. The structures were fully characterized by cumulative analyses of NMR, IR, and MS spectra, along with density functional theory computational calculations. All three of the new compounds feature an unusual 2,3-dihydro-4H-pyran-4-one moiety, but only enigmazoles C (1) and D (3) showed cytotoxic activity in the micromolar range against A-549 (lung), HT-29 (colon), MDA-MB-231 (breast), and PSN-1 (pancreas) tumor cells. American Chemical Society and American Society of Pharmacognosy 2022-03-02 2022-04-22 /pmc/articles/PMC9040057/ /pubmed/35234467 http://dx.doi.org/10.1021/acs.jnatprod.1c01179 Text en © 2022 The Authors. Published by American Chemical Society and American Society of Pharmacognosy https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Tarazona, Guillermo
Fernández, Rogelio
Pérez, Marta
Millán, Ramón E.
Jiménez, Carlos
Rodríguez, Jaime
Cuevas, Carmen
Enigmazole C: A Cytotoxic Macrocyclic Lactone and Its Ring-Opened Derivatives from a New Species of Homophymia Sponge
title Enigmazole C: A Cytotoxic Macrocyclic Lactone and Its Ring-Opened Derivatives from a New Species of Homophymia Sponge
title_full Enigmazole C: A Cytotoxic Macrocyclic Lactone and Its Ring-Opened Derivatives from a New Species of Homophymia Sponge
title_fullStr Enigmazole C: A Cytotoxic Macrocyclic Lactone and Its Ring-Opened Derivatives from a New Species of Homophymia Sponge
title_full_unstemmed Enigmazole C: A Cytotoxic Macrocyclic Lactone and Its Ring-Opened Derivatives from a New Species of Homophymia Sponge
title_short Enigmazole C: A Cytotoxic Macrocyclic Lactone and Its Ring-Opened Derivatives from a New Species of Homophymia Sponge
title_sort enigmazole c: a cytotoxic macrocyclic lactone and its ring-opened derivatives from a new species of homophymia sponge
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9040057/
https://www.ncbi.nlm.nih.gov/pubmed/35234467
http://dx.doi.org/10.1021/acs.jnatprod.1c01179
work_keys_str_mv AT tarazonaguillermo enigmazolecacytotoxicmacrocycliclactoneanditsringopenedderivativesfromanewspeciesofhomophymiasponge
AT fernandezrogelio enigmazolecacytotoxicmacrocycliclactoneanditsringopenedderivativesfromanewspeciesofhomophymiasponge
AT perezmarta enigmazolecacytotoxicmacrocycliclactoneanditsringopenedderivativesfromanewspeciesofhomophymiasponge
AT millanramone enigmazolecacytotoxicmacrocycliclactoneanditsringopenedderivativesfromanewspeciesofhomophymiasponge
AT jimenezcarlos enigmazolecacytotoxicmacrocycliclactoneanditsringopenedderivativesfromanewspeciesofhomophymiasponge
AT rodriguezjaime enigmazolecacytotoxicmacrocycliclactoneanditsringopenedderivativesfromanewspeciesofhomophymiasponge
AT cuevascarmen enigmazolecacytotoxicmacrocycliclactoneanditsringopenedderivativesfromanewspeciesofhomophymiasponge

Ejemplares similares