Cargando…
LC-ToF-ESI-MS Patterns of Hirsutinolide-like Sesquiterpenoids Present in the Elephantopus mollis Kunth Extract and Chemophenetic Significance of Its Chemical Constituents
A total of nine sesquiterpenoid lactones together with phenolic compounds and other terpenes were identified from the crude methanol extract of Elephantopus mollis Kunth. Compounds were isolated using different chromatographic techniques and their structures were determined by NMR and IR spectroscop...
Autores principales: | , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8399899/ https://www.ncbi.nlm.nih.gov/pubmed/34443397 http://dx.doi.org/10.3390/molecules26164810 |
_version_ | 1783745185939718144 |
---|---|
author | Bitchagno, Gabin Thierry M. Koffi, Jean Garba Simo, Ingrid Konga Kagho, Donald Ulrich K. Ngouela, Augustin Silvere Lenta, Bruno Ndjakou Sewald, Norbert |
author_facet | Bitchagno, Gabin Thierry M. Koffi, Jean Garba Simo, Ingrid Konga Kagho, Donald Ulrich K. Ngouela, Augustin Silvere Lenta, Bruno Ndjakou Sewald, Norbert |
author_sort | Bitchagno, Gabin Thierry M. |
collection | PubMed |
description | A total of nine sesquiterpenoid lactones together with phenolic compounds and other terpenes were identified from the crude methanol extract of Elephantopus mollis Kunth. Compounds were isolated using different chromatographic techniques and their structures were determined by NMR and IR spectroscopy as well as mass spectrometry. The structures of some detected compounds were assigned based on LC-ToF-ESI-MS screening of main fractions/subfractions from flash chromatography and comparison with isolated analogues as standards. The findings revealed not only the in-source loss of water as the base peak in hirsutinolides but also the in-source loss of corresponding alcohol when the oxygen at position 1 is alkylated. The present study also draws up a complement of data with respect to hirsutinolide-like sesquiterpene lactones whose LC-MS characteristics are not available in the literature. The chemophenetic significance is also discussed. Some of the isolated compounds were reported for the first time to be found in the species, the genus as well as the plant family. The medium-polar fractions of the crude extract, also containing the larger amount of sesquiterpenoid lactones, exhibited activity both against a cancer cell line and bacterial strains. Isolated lactones were also active against the cancer cell line, while the chlorogenic derivatives also valuable in Elephantopus genus showed potent radical scavenging activity. This is the first report of cytotoxic and antibacterial activities of our samples against the tested strains and cell line. The present study follows the ongoing research project dealing with the characterization of taxa with antibacterial and antiparasitic activities from Cameroonian pharmacopeia. |
format | Online Article Text |
id | pubmed-8399899 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-83998992021-08-29 LC-ToF-ESI-MS Patterns of Hirsutinolide-like Sesquiterpenoids Present in the Elephantopus mollis Kunth Extract and Chemophenetic Significance of Its Chemical Constituents Bitchagno, Gabin Thierry M. Koffi, Jean Garba Simo, Ingrid Konga Kagho, Donald Ulrich K. Ngouela, Augustin Silvere Lenta, Bruno Ndjakou Sewald, Norbert Molecules Article A total of nine sesquiterpenoid lactones together with phenolic compounds and other terpenes were identified from the crude methanol extract of Elephantopus mollis Kunth. Compounds were isolated using different chromatographic techniques and their structures were determined by NMR and IR spectroscopy as well as mass spectrometry. The structures of some detected compounds were assigned based on LC-ToF-ESI-MS screening of main fractions/subfractions from flash chromatography and comparison with isolated analogues as standards. The findings revealed not only the in-source loss of water as the base peak in hirsutinolides but also the in-source loss of corresponding alcohol when the oxygen at position 1 is alkylated. The present study also draws up a complement of data with respect to hirsutinolide-like sesquiterpene lactones whose LC-MS characteristics are not available in the literature. The chemophenetic significance is also discussed. Some of the isolated compounds were reported for the first time to be found in the species, the genus as well as the plant family. The medium-polar fractions of the crude extract, also containing the larger amount of sesquiterpenoid lactones, exhibited activity both against a cancer cell line and bacterial strains. Isolated lactones were also active against the cancer cell line, while the chlorogenic derivatives also valuable in Elephantopus genus showed potent radical scavenging activity. This is the first report of cytotoxic and antibacterial activities of our samples against the tested strains and cell line. The present study follows the ongoing research project dealing with the characterization of taxa with antibacterial and antiparasitic activities from Cameroonian pharmacopeia. MDPI 2021-08-09 /pmc/articles/PMC8399899/ /pubmed/34443397 http://dx.doi.org/10.3390/molecules26164810 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Bitchagno, Gabin Thierry M. Koffi, Jean Garba Simo, Ingrid Konga Kagho, Donald Ulrich K. Ngouela, Augustin Silvere Lenta, Bruno Ndjakou Sewald, Norbert LC-ToF-ESI-MS Patterns of Hirsutinolide-like Sesquiterpenoids Present in the Elephantopus mollis Kunth Extract and Chemophenetic Significance of Its Chemical Constituents |
title | LC-ToF-ESI-MS Patterns of Hirsutinolide-like Sesquiterpenoids Present in the Elephantopus mollis Kunth Extract and Chemophenetic Significance of Its Chemical Constituents |
title_full | LC-ToF-ESI-MS Patterns of Hirsutinolide-like Sesquiterpenoids Present in the Elephantopus mollis Kunth Extract and Chemophenetic Significance of Its Chemical Constituents |
title_fullStr | LC-ToF-ESI-MS Patterns of Hirsutinolide-like Sesquiterpenoids Present in the Elephantopus mollis Kunth Extract and Chemophenetic Significance of Its Chemical Constituents |
title_full_unstemmed | LC-ToF-ESI-MS Patterns of Hirsutinolide-like Sesquiterpenoids Present in the Elephantopus mollis Kunth Extract and Chemophenetic Significance of Its Chemical Constituents |
title_short | LC-ToF-ESI-MS Patterns of Hirsutinolide-like Sesquiterpenoids Present in the Elephantopus mollis Kunth Extract and Chemophenetic Significance of Its Chemical Constituents |
title_sort | lc-tof-esi-ms patterns of hirsutinolide-like sesquiterpenoids present in the elephantopus mollis kunth extract and chemophenetic significance of its chemical constituents |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8399899/ https://www.ncbi.nlm.nih.gov/pubmed/34443397 http://dx.doi.org/10.3390/molecules26164810 |
work_keys_str_mv | AT bitchagnogabinthierrym lctofesimspatternsofhirsutinolidelikesesquiterpenoidspresentintheelephantopusmolliskunthextractandchemopheneticsignificanceofitschemicalconstituents AT koffijeangarba lctofesimspatternsofhirsutinolidelikesesquiterpenoidspresentintheelephantopusmolliskunthextractandchemopheneticsignificanceofitschemicalconstituents AT simoingridkonga lctofesimspatternsofhirsutinolidelikesesquiterpenoidspresentintheelephantopusmolliskunthextractandchemopheneticsignificanceofitschemicalconstituents AT kaghodonaldulrichk lctofesimspatternsofhirsutinolidelikesesquiterpenoidspresentintheelephantopusmolliskunthextractandchemopheneticsignificanceofitschemicalconstituents AT ngouelaaugustinsilvere lctofesimspatternsofhirsutinolidelikesesquiterpenoidspresentintheelephantopusmolliskunthextractandchemopheneticsignificanceofitschemicalconstituents AT lentabrunondjakou lctofesimspatternsofhirsutinolidelikesesquiterpenoidspresentintheelephantopusmolliskunthextractandchemopheneticsignificanceofitschemicalconstituents AT sewaldnorbert lctofesimspatternsofhirsutinolidelikesesquiterpenoidspresentintheelephantopusmolliskunthextractandchemopheneticsignificanceofitschemicalconstituents |