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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...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society and American
Society of Pharmacognosy
2014
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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. |
format | Online Article Text |
id | pubmed-3971758 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | American Chemical
Society and American
Society of Pharmacognosy |
record_format | MEDLINE/PubMed |
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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