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(±)-Hypernumqulins A-H: Eight pairs of unexpected [2+2] cycloaddition sesquiterpenoid alkaloid with 6/6/6/4/10 ring system from Hypericum monogynum L.
- Source :
-
Bioorganic chemistry [Bioorg Chem] 2024 Sep; Vol. 150, pp. 107564. Date of Electronic Publication: 2024 Jun 14. - Publication Year :
- 2024
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Abstract
- (±)-Hypernumqulins A-H (1-8), eight pairs of enantiomeric quinoline alkaloids fused with an isopentenyl and a germacrane-type sesquiterpenoid, featuring an unprecedented skeleton with 6/6/6/4/10 ring system, were isolated from Hypericum monogynum L. under the guidance of molecular networking strategy. Their structures including absolute configuration were elucidated by NMR spectroscopy analysis, X-ray crystallography and quantum chemical calculation. The proposed [2+2] cycloaddition may play a key biogenic step in building the unexpected skeleton. Most of the isolates exhibited cytotoxicity with IC <subscript>50</subscript> values ranging from 2.82 ± 0.03 to 45.25 ± 1.26 μM against MCF-7, A549 or SGC7901 cells. Furthermore, compounds (±)-1 and (-)-1 could induce apoptosis by upregulating the protein expression level of Bax and downregulating of Bcl-2 in MCF-7 cells. These findings provided the first example of germacrane sesquiterpene quinoline alkaloids, and supported the possibilities for the development of new anti-tumor agents.<br />Competing Interests: 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.<br /> (Copyright © 2024. Published by Elsevier Inc.)
- Subjects :
- Humans
Apoptosis drug effects
Cell Line, Tumor
Cell Proliferation drug effects
Cycloaddition Reaction
Molecular Structure
Stereoisomerism
Structure-Activity Relationship
Quinolines chemistry
Quinolines isolation & purification
Quinolines pharmacology
Alkaloids chemistry
Alkaloids pharmacology
Alkaloids isolation & purification
Antineoplastic Agents, Phytogenic pharmacology
Antineoplastic Agents, Phytogenic chemistry
Antineoplastic Agents, Phytogenic isolation & purification
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Hypericum chemistry
Sesquiterpenes chemistry
Sesquiterpenes pharmacology
Sesquiterpenes isolation & purification
Subjects
Details
- Language :
- English
- ISSN :
- 1090-2120
- Volume :
- 150
- Database :
- MEDLINE
- Journal :
- Bioorganic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 38889550
- Full Text :
- https://doi.org/10.1016/j.bioorg.2024.107564