(±)-hypermonanones A-G, seven pairs of monoterpenoid polyprenylated acylphloroglucinol enantiomers from Hypericum monanthemum.
Fitoterapia
; 176: 105985, 2024 Jul.
Article
in En
| MEDLINE
| ID: mdl-38705541
ABSTRACT
Seven pairs of undescribed monoterpenoid polyprenylated acylphloroglucinol enantiomers [(±)-hypermonanones A-G (1-7)], together with three known analogues, were identified from the whole plant of Hypericum monanthemum Hook. The structures of these compounds were determined by analyses of their UV, HRESIMS, 1D/2D NMR spectroscopic data, and NMR calculations. The absolute configurations of these compounds were assigned by ECD calculations after chiral HPLC separation. Diverse monoterpene moieties were fused at C-3/C-4 of the dearomatized acylphloroglucinol core, which led to 3,4-dihydro-2H-pyran-integrated angular or linear type 6/6/6 tricyclic skeletons in 1-7. Compounds (-)-2 and (+)-2 exhibited significant NO inhibitory activity against LPS induced RAW264.7 cells with the IC50 values of 7.07 ± 1.02 µM and 11.39 ± 0.24 µM, respectively.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Phloroglucinol
/
Hypericum
/
Monoterpenes
/
Phytochemicals
Limits:
Animals
Country/Region as subject:
Asia
Language:
En
Journal:
Fitoterapia
Year:
2024
Document type:
Article