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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...

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Autores principales: 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
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
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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.
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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
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