Carapanosins D—F from the Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production

A novel nor-phragmalin-type limonoid, named carapanosin D (1), and two novel mexicanolide-type limonoids, carapanosins E (2) and F (3), were isolated from the seed oil of andiroba (Carapa guianensis A(ublet)), a traditional medicine in Brazil and Latin American countries. Their structures were unamb...

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Detalles Bibliográficos
Autores principales: Inoue, Takanobu, Ohmori, Shoko, Kikuchi, Takashi, Yamada, Takeshi, Tanaka, Reiko
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6099744/
https://www.ncbi.nlm.nih.gov/pubmed/30029521
http://dx.doi.org/10.3390/molecules23071778
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author Inoue, Takanobu
Ohmori, Shoko
Kikuchi, Takashi
Yamada, Takeshi
Tanaka, Reiko
author_facet Inoue, Takanobu
Ohmori, Shoko
Kikuchi, Takashi
Yamada, Takeshi
Tanaka, Reiko
author_sort Inoue, Takanobu
collection PubMed
description A novel nor-phragmalin-type limonoid, named carapanosin D (1), and two novel mexicanolide-type limonoids, carapanosins E (2) and F (3), were isolated from the seed oil of andiroba (Carapa guianensis A(ublet)), a traditional medicine in Brazil and Latin American countries. Their structures were unambiguously determined on the basis of spectroscopic analyses using one-dimensional (1D) and two-dimensional (2D) NMR techniques and High resolution Fast Atom Bombardment Mass Spectrometry (HRFABMS). Compounds 1–3 were evaluated for their effects on the production of nitric oxide (NO) in Lipopolysaccharide (LPS)-activated mouse peritoneal macrophages. The NO inhibitory assay suggested that compounds 2 and 3 have high potency as inhibitors of macrophage activation.
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spelling pubmed-60997442018-11-13 Carapanosins D—F from the Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production Inoue, Takanobu Ohmori, Shoko Kikuchi, Takashi Yamada, Takeshi Tanaka, Reiko Molecules Article A novel nor-phragmalin-type limonoid, named carapanosin D (1), and two novel mexicanolide-type limonoids, carapanosins E (2) and F (3), were isolated from the seed oil of andiroba (Carapa guianensis A(ublet)), a traditional medicine in Brazil and Latin American countries. Their structures were unambiguously determined on the basis of spectroscopic analyses using one-dimensional (1D) and two-dimensional (2D) NMR techniques and High resolution Fast Atom Bombardment Mass Spectrometry (HRFABMS). Compounds 1–3 were evaluated for their effects on the production of nitric oxide (NO) in Lipopolysaccharide (LPS)-activated mouse peritoneal macrophages. The NO inhibitory assay suggested that compounds 2 and 3 have high potency as inhibitors of macrophage activation. MDPI 2018-07-19 /pmc/articles/PMC6099744/ /pubmed/30029521 http://dx.doi.org/10.3390/molecules23071778 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Inoue, Takanobu
Ohmori, Shoko
Kikuchi, Takashi
Yamada, Takeshi
Tanaka, Reiko
Carapanosins D—F from the Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production
title Carapanosins D—F from the Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production
title_full Carapanosins D—F from the Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production
title_fullStr Carapanosins D—F from the Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production
title_full_unstemmed Carapanosins D—F from the Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production
title_short Carapanosins D—F from the Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production
title_sort carapanosins d—f from the seeds of andiroba (carapa guianensis, meliaceae) and their effects on lps-activated no production
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6099744/
https://www.ncbi.nlm.nih.gov/pubmed/30029521
http://dx.doi.org/10.3390/molecules23071778
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