Structurally diverse new eudesmane sesquiterpenoids with anti-inflammatory activity from the fruits of Alpinia oxyphylla.
Alpinia oxyphylla
Anti-inflammatory activity
Eudesmane sesquiterpenoids
Structural elucidation
Journal
Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703
Informations de publication
Date de publication:
05 2023
05 2023
Historique:
received:
21
12
2022
revised:
17
01
2023
accepted:
20
01
2023
medline:
5
4
2023
pubmed:
2
3
2023
entrez:
1
3
2023
Statut:
ppublish
Résumé
The phytochemical investigation of the fruits of Alpinia oxyphylla led to the isolation and identification of 40 structurally diverse sesquiterpenoids, including 17 new eudesmane sesquiterpenoids (1-17) and 23 known analogues (18-40). Among the isolates, 14 and 17 were unusual rearranged eudesmane sesquiterpenoids, featuring rare 5/6-fused and 6/8-fused bicyclic carbon skeleton, respectively; 15 and 16 were the novel 6,7-seco-eudesmane sesquiterpenoids isolated from plant-origin for the first time, 1 and 3-6 were rare nor-eudesmane sesquiterpenoids. Their structures were elucidated by comprehensive spectroscopic data analysis (NMR, HRESIMS, IR, UV), single crystal X-ray diffraction, and quantum chemistry calculations (ECD and
Identifiants
pubmed: 36857933
pii: S0045-2068(23)00091-3
doi: 10.1016/j.bioorg.2023.106431
pii:
doi:
Substances chimiques
Tumor Necrosis Factor-alpha
0
Lipopolysaccharides
0
Cyclooxygenase 2
EC 1.14.99.1
Interleukin-6
0
Anti-Inflammatory Agents
0
eudesmane
473-11-0
Sesquiterpenes, Eudesmane
0
Sesquiterpenes
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
106431Informations de copyright
Copyright © 2023 Elsevier Inc. All rights reserved.
Déclaration de conflit d'intérêts
Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.