Cargando…
In vitro anti-inflammatory, in silico molecular docking and molecular dynamics simulation of oleanane-type triterpenes from aerial parts of Mussaenda recurvata
Bioactive-guided investigation of the aerial parts of Mussaenda recurvata Naiki, Tagane, and Yahara (Rubiaceae) led to the isolation of four triterpenes, including two new triterpenes recurvatanes A and B (1 and 2), along with two known compounds 3β,6β,23-trihydroxyolean-12-en-28-oic acid (3) and 3β...
Autores principales: | , , , , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9923456/ https://www.ncbi.nlm.nih.gov/pubmed/36793303 http://dx.doi.org/10.1039/d2ra06870b |
_version_ | 1784887744215908352 |
---|---|
author | Tri, Mai Dinh Phat, Nguyen Tan Minh, Phan Nhat Chi, Mai Thanh Hao, Bui Xuan Minh An, Tran Nguyen Alam, Mahboob Van Kieu, Nguyen Dang, Van-Son Mai, Tran Thi Ngoc Duong, Thuc-Huy |
author_facet | Tri, Mai Dinh Phat, Nguyen Tan Minh, Phan Nhat Chi, Mai Thanh Hao, Bui Xuan Minh An, Tran Nguyen Alam, Mahboob Van Kieu, Nguyen Dang, Van-Son Mai, Tran Thi Ngoc Duong, Thuc-Huy |
author_sort | Tri, Mai Dinh |
collection | PubMed |
description | Bioactive-guided investigation of the aerial parts of Mussaenda recurvata Naiki, Tagane, and Yahara (Rubiaceae) led to the isolation of four triterpenes, including two new triterpenes recurvatanes A and B (1 and 2), along with two known compounds 3β,6β,23-trihydroxyolean-12-en-28-oic acid (3) and 3β,6β,19α,23-tetrahydroxyolean-12-en-28-oic acid (4). The chemical structures of the compounds were identified from spectroscopic data and by comparison with the literature. A comprehensive review of NMR data of the oleanane-type triterpenes bearing 3-hydroxy and 4-hydroxymethylene groups indicated the characteristic spectroscopic features in this series. Compounds 1–4 were evaluated for the inhibitory NO production in LPS-stimulated RAW264.7 cells. Compounds 2 and 3 showed a moderate reduction of nitrite accumulation with IC(50) values of 55.63 ± 2.52 and 60.08 ± 3.17 μM, respectively. Molecular docking model dedicated to compound 3 or pose 420, which is the best candidate among docking poses of compounds 1–4 interacted well with the crystal structure of enzyme 4WCU: PDB. The best ligand molecule, pose 420 in terms of binding energy obtained from docking studies on molecular dynamics (MD) simulations for 100 ns exhibited non-bonding interactions with the protein and remained stable inside the active site. |
format | Online Article Text |
id | pubmed-9923456 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-99234562023-02-14 In vitro anti-inflammatory, in silico molecular docking and molecular dynamics simulation of oleanane-type triterpenes from aerial parts of Mussaenda recurvata Tri, Mai Dinh Phat, Nguyen Tan Minh, Phan Nhat Chi, Mai Thanh Hao, Bui Xuan Minh An, Tran Nguyen Alam, Mahboob Van Kieu, Nguyen Dang, Van-Son Mai, Tran Thi Ngoc Duong, Thuc-Huy RSC Adv Chemistry Bioactive-guided investigation of the aerial parts of Mussaenda recurvata Naiki, Tagane, and Yahara (Rubiaceae) led to the isolation of four triterpenes, including two new triterpenes recurvatanes A and B (1 and 2), along with two known compounds 3β,6β,23-trihydroxyolean-12-en-28-oic acid (3) and 3β,6β,19α,23-tetrahydroxyolean-12-en-28-oic acid (4). The chemical structures of the compounds were identified from spectroscopic data and by comparison with the literature. A comprehensive review of NMR data of the oleanane-type triterpenes bearing 3-hydroxy and 4-hydroxymethylene groups indicated the characteristic spectroscopic features in this series. Compounds 1–4 were evaluated for the inhibitory NO production in LPS-stimulated RAW264.7 cells. Compounds 2 and 3 showed a moderate reduction of nitrite accumulation with IC(50) values of 55.63 ± 2.52 and 60.08 ± 3.17 μM, respectively. Molecular docking model dedicated to compound 3 or pose 420, which is the best candidate among docking poses of compounds 1–4 interacted well with the crystal structure of enzyme 4WCU: PDB. The best ligand molecule, pose 420 in terms of binding energy obtained from docking studies on molecular dynamics (MD) simulations for 100 ns exhibited non-bonding interactions with the protein and remained stable inside the active site. The Royal Society of Chemistry 2023-02-13 /pmc/articles/PMC9923456/ /pubmed/36793303 http://dx.doi.org/10.1039/d2ra06870b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Tri, Mai Dinh Phat, Nguyen Tan Minh, Phan Nhat Chi, Mai Thanh Hao, Bui Xuan Minh An, Tran Nguyen Alam, Mahboob Van Kieu, Nguyen Dang, Van-Son Mai, Tran Thi Ngoc Duong, Thuc-Huy In vitro anti-inflammatory, in silico molecular docking and molecular dynamics simulation of oleanane-type triterpenes from aerial parts of Mussaenda recurvata |
title |
In vitro anti-inflammatory, in silico molecular docking and molecular dynamics simulation of oleanane-type triterpenes from aerial parts of Mussaenda recurvata |
title_full |
In vitro anti-inflammatory, in silico molecular docking and molecular dynamics simulation of oleanane-type triterpenes from aerial parts of Mussaenda recurvata |
title_fullStr |
In vitro anti-inflammatory, in silico molecular docking and molecular dynamics simulation of oleanane-type triterpenes from aerial parts of Mussaenda recurvata |
title_full_unstemmed |
In vitro anti-inflammatory, in silico molecular docking and molecular dynamics simulation of oleanane-type triterpenes from aerial parts of Mussaenda recurvata |
title_short |
In vitro anti-inflammatory, in silico molecular docking and molecular dynamics simulation of oleanane-type triterpenes from aerial parts of Mussaenda recurvata |
title_sort | in vitro anti-inflammatory, in silico molecular docking and molecular dynamics simulation of oleanane-type triterpenes from aerial parts of mussaenda recurvata |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9923456/ https://www.ncbi.nlm.nih.gov/pubmed/36793303 http://dx.doi.org/10.1039/d2ra06870b |
work_keys_str_mv | AT trimaidinh invitroantiinflammatoryinsilicomoleculardockingandmoleculardynamicssimulationofoleananetypetriterpenesfromaerialpartsofmussaendarecurvata AT phatnguyentan invitroantiinflammatoryinsilicomoleculardockingandmoleculardynamicssimulationofoleananetypetriterpenesfromaerialpartsofmussaendarecurvata AT minhphannhat invitroantiinflammatoryinsilicomoleculardockingandmoleculardynamicssimulationofoleananetypetriterpenesfromaerialpartsofmussaendarecurvata AT chimaithanh invitroantiinflammatoryinsilicomoleculardockingandmoleculardynamicssimulationofoleananetypetriterpenesfromaerialpartsofmussaendarecurvata AT haobuixuan invitroantiinflammatoryinsilicomoleculardockingandmoleculardynamicssimulationofoleananetypetriterpenesfromaerialpartsofmussaendarecurvata AT minhantrannguyen invitroantiinflammatoryinsilicomoleculardockingandmoleculardynamicssimulationofoleananetypetriterpenesfromaerialpartsofmussaendarecurvata AT alammahboob invitroantiinflammatoryinsilicomoleculardockingandmoleculardynamicssimulationofoleananetypetriterpenesfromaerialpartsofmussaendarecurvata AT vankieunguyen invitroantiinflammatoryinsilicomoleculardockingandmoleculardynamicssimulationofoleananetypetriterpenesfromaerialpartsofmussaendarecurvata AT dangvanson invitroantiinflammatoryinsilicomoleculardockingandmoleculardynamicssimulationofoleananetypetriterpenesfromaerialpartsofmussaendarecurvata AT maitranthingoc invitroantiinflammatoryinsilicomoleculardockingandmoleculardynamicssimulationofoleananetypetriterpenesfromaerialpartsofmussaendarecurvata AT duongthuchuy invitroantiinflammatoryinsilicomoleculardockingandmoleculardynamicssimulationofoleananetypetriterpenesfromaerialpartsofmussaendarecurvata |