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Sesquiterpenes from Neurolaena lobata and Their Antiproliferative and Anti-inflammatory Activities

[Image: see text] Five new sesquiterpenes, neurolobatin A (1), neurolobatin B (2), 5β-hydroxy-8β-isovaleroyloxy-9α-hydroxycalyculatolide (3), 3-epi-desacetylisovaleroylheliangine (4), and 3β-acetoxy-8β-isovaleroyloxyreynosin (5), were isolated from the aerial parts of Neurolaena lobata. The structur...

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Autores principales: Lajter, Ildikó, Vasas, Andrea, Béni, Zoltán, Forgo, Peter, Binder, Markus, Bochkov, Valery, Zupkó, István, Krupitza, Georg, Frisch, Richard, Kopp, Brigitte, Hohmann, Judit
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society and American Society of Pharmacognosy 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3971758/
https://www.ncbi.nlm.nih.gov/pubmed/24476550
http://dx.doi.org/10.1021/np400834c
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author Lajter, Ildikó
Vasas, Andrea
Béni, Zoltán
Forgo, Peter
Binder, Markus
Bochkov, Valery
Zupkó, István
Krupitza, Georg
Frisch, Richard
Kopp, Brigitte
Hohmann, Judit
author_facet Lajter, Ildikó
Vasas, Andrea
Béni, Zoltán
Forgo, Peter
Binder, Markus
Bochkov, Valery
Zupkó, István
Krupitza, Georg
Frisch, Richard
Kopp, Brigitte
Hohmann, Judit
author_sort Lajter, Ildikó
collection PubMed
description [Image: see text] Five new sesquiterpenes, neurolobatin A (1), neurolobatin B (2), 5β-hydroxy-8β-isovaleroyloxy-9α-hydroxycalyculatolide (3), 3-epi-desacetylisovaleroylheliangine (4), and 3β-acetoxy-8β-isovaleroyloxyreynosin (5), were isolated from the aerial parts of Neurolaena lobata. The structures were established by means of a combined spectroscopic data analysis, including ESIMS, APCI-MS, and 1D- and 2D-NMR techniques. Neurolobatin A (1) and B (2) are unusual isomeric seco-germacranolide sesquiterpenes with a bicyclic acetal moiety, compounds 3 and 4 are unsaturated epoxy-germacranolide esters, and compound 5 is the first eudesmanolide isolated from the genus Neurolaena. The isolated compounds (1–5) were shown to have noteworthy antiproliferative activities against human tumor cell lines (A2780, A431, HeLa, and MCF7). The anti-inflammatory effects of 1–5, evaluated in vitro using LPS- and TNF-α-induced IL-8 expression inhibitory assays, revealed that all these compounds strongly down-regulated the LPS-induced production of IL-8 protein, with neurolobatin B (2) and 3-epi-desacetylisovaleroylheliangine (4) being the most effective.
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spelling pubmed-39717582014-04-01 Sesquiterpenes from Neurolaena lobata and Their Antiproliferative and Anti-inflammatory Activities Lajter, Ildikó Vasas, Andrea Béni, Zoltán Forgo, Peter Binder, Markus Bochkov, Valery Zupkó, István Krupitza, Georg Frisch, Richard Kopp, Brigitte Hohmann, Judit J Nat Prod [Image: see text] Five new sesquiterpenes, neurolobatin A (1), neurolobatin B (2), 5β-hydroxy-8β-isovaleroyloxy-9α-hydroxycalyculatolide (3), 3-epi-desacetylisovaleroylheliangine (4), and 3β-acetoxy-8β-isovaleroyloxyreynosin (5), were isolated from the aerial parts of Neurolaena lobata. The structures were established by means of a combined spectroscopic data analysis, including ESIMS, APCI-MS, and 1D- and 2D-NMR techniques. Neurolobatin A (1) and B (2) are unusual isomeric seco-germacranolide sesquiterpenes with a bicyclic acetal moiety, compounds 3 and 4 are unsaturated epoxy-germacranolide esters, and compound 5 is the first eudesmanolide isolated from the genus Neurolaena. The isolated compounds (1–5) were shown to have noteworthy antiproliferative activities against human tumor cell lines (A2780, A431, HeLa, and MCF7). The anti-inflammatory effects of 1–5, evaluated in vitro using LPS- and TNF-α-induced IL-8 expression inhibitory assays, revealed that all these compounds strongly down-regulated the LPS-induced production of IL-8 protein, with neurolobatin B (2) and 3-epi-desacetylisovaleroylheliangine (4) being the most effective. American Chemical Society and American Society of Pharmacognosy 2014-01-29 2014-03-28 /pmc/articles/PMC3971758/ /pubmed/24476550 http://dx.doi.org/10.1021/np400834c Text en Copyright © 2014 American Chemical Society and American Society of Pharmacognosy Terms of Use CC-BY (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html)
spellingShingle Lajter, Ildikó
Vasas, Andrea
Béni, Zoltán
Forgo, Peter
Binder, Markus
Bochkov, Valery
Zupkó, István
Krupitza, Georg
Frisch, Richard
Kopp, Brigitte
Hohmann, Judit
Sesquiterpenes from Neurolaena lobata and Their Antiproliferative and Anti-inflammatory Activities
title Sesquiterpenes from Neurolaena lobata and Their Antiproliferative and Anti-inflammatory Activities
title_full Sesquiterpenes from Neurolaena lobata and Their Antiproliferative and Anti-inflammatory Activities
title_fullStr Sesquiterpenes from Neurolaena lobata and Their Antiproliferative and Anti-inflammatory Activities
title_full_unstemmed Sesquiterpenes from Neurolaena lobata and Their Antiproliferative and Anti-inflammatory Activities
title_short Sesquiterpenes from Neurolaena lobata and Their Antiproliferative and Anti-inflammatory Activities
title_sort sesquiterpenes from neurolaena lobata and their antiproliferative and anti-inflammatory activities
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3971758/
https://www.ncbi.nlm.nih.gov/pubmed/24476550
http://dx.doi.org/10.1021/np400834c
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