Carbazole alkaloids from the fruits of Clausena anisum-olens with potential PTP1B and α-glucosidase inhibitory activities.
Alkaloids
/ chemistry
Carbazoles
/ chemistry
Clausena
/ chemistry
Dose-Response Relationship, Drug
Enzyme Inhibitors
/ chemistry
Fruit
/ chemistry
Humans
Molecular Docking Simulation
Molecular Structure
Protein Tyrosine Phosphatase, Non-Receptor Type 1
/ antagonists & inhibitors
Structure-Activity Relationship
alpha-Glucosidases
/ metabolism
Carbazole alkaloids
Clausena anisum-olens
Clausenanisines A–F
PTP1B inhibitory activities
α-glucosidase inhibitory activities
Journal
Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703
Informations de publication
Date de publication:
05 2021
05 2021
Historique:
received:
06
09
2020
revised:
06
11
2020
accepted:
21
02
2021
pubmed:
17
3
2021
medline:
13
10
2021
entrez:
16
3
2021
Statut:
ppublish
Résumé
The phytochemical investigation on the fruits of Clausena anisum-olens led to the isolation of 18 carbazole alkaloids (1-18), containing three new ones, clausenanisines A-C (1-3), and three new naturally occurring carbazole alkaloids, clausenanisines D-F (4-6), as well as 12 known analogues (7-18). The chemical structures of clausenanisines A-F (1-6) were elucidated by extensive spectroscopic methods. Notably, clausenanisine A (1) was a novel carbazole alkaloid with a unique five-membered cyclic ether, while clausenanisine E (5) is an unusual carbazole alkaloid owning an unprecedented naturally occurring carbon skeleton possessing 14 carbon atoms. The known carbazole alkaloids (7-18) were identified by the comparison of their spectral data with those data reported in the literature. All known carbazole alkaloids 7-18 were isolated from C. anisum-olens for the first time. Moreover, all isolated compounds 1-18 were assessed for their protein tyrosine phosphatase 1B (PTP1B) and α-glucosidase inhibitory activities in vitro. Compounds 1-18 exhibited remarkable PTP1B inhibitory activities with IC
Identifiants
pubmed: 33725509
pii: S0045-2068(21)00152-8
doi: 10.1016/j.bioorg.2021.104775
pii:
doi:
Substances chimiques
Alkaloids
0
Carbazoles
0
Enzyme Inhibitors
0
carbazole
0P2197HHHN
PTPN1 protein, human
EC 3.1.3.48
Protein Tyrosine Phosphatase, Non-Receptor Type 1
EC 3.1.3.48
alpha-Glucosidases
EC 3.2.1.20
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
104775Informations de copyright
Copyright © 2021 Elsevier Inc. All rights reserved.