Xanthone derivatives from the leaves of Garcinia oligantha.
Antineoplastic Agents, Phytogenic
/ chemistry
Caspase 3
/ metabolism
Cell Death
/ drug effects
Cell Line, Tumor
Cell Proliferation
/ drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Enzyme Inhibitors
/ chemistry
Garcinia
/ chemistry
Humans
Molecular Structure
Plant Leaves
/ chemistry
Structure-Activity Relationship
Xanthones
/ chemistry
Cell death
Garcinia oligantha
Mitochondrial apoptosis pathway
Quiescent prostate cancer cells
Xanthones
Journal
European journal of medicinal chemistry
ISSN: 1768-3254
Titre abrégé: Eur J Med Chem
Pays: France
ID NLM: 0420510
Informations de publication
Date de publication:
01 Nov 2019
01 Nov 2019
Historique:
received:
10
07
2019
accepted:
11
07
2019
pubmed:
4
8
2019
medline:
31
12
2019
entrez:
4
8
2019
Statut:
ppublish
Résumé
Nine new and unique xanthone derivatives, including one novel hybrid monoterpene-tetrahydroxanthone (1), three dihydro-xanthone derivatives (2-4), and five skeleton-rearranged xanthone derivatives (5-9), were obtained from a 95% EtOH extract of Garcinia oligantha leaves by a LC-MS-guided fractionation procedure. The structures of the new compounds were elucidated by analysis of their 1D and 2D NMR and MS data. The relative configurations of 2 and 8 were determined via X-ray crystallographic data analysis, while the absolute configurations of 1-2, 5-9 were assigned based on a comparison of calculated and experimental ECD and/or OR data. In SRB, PI-exclusion and Hoechst staining assays, 6 showed strong cytotoxic activities which could dose-dependently induce Taxol-insensitive quiescent LNCaP cell death. Additionally, a preliminary mechanism investigation using immunoblotting and Caspase-3 activity assay, indicated that 6 induced quiescent LNCaP cell death potentially through caspase-dependent mitochondrial apoptosis pathway.
Identifiants
pubmed: 31376561
pii: S0223-5234(19)30660-9
doi: 10.1016/j.ejmech.2019.07.039
pii:
doi:
Substances chimiques
Antineoplastic Agents, Phytogenic
0
Enzyme Inhibitors
0
Xanthones
0
Caspase 3
EC 3.4.22.-
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
111536Informations de copyright
Copyright © 2019 Elsevier Masson SAS. All rights reserved.