1. (±)-hypermonanones A-G, seven pairs of monoterpenoid polyprenylated acylphloroglucinol enantiomers from Hypericum monanthemum.
- Author
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Cao TJ, Ying P, Zheng Q, Wu YJ, Wang XL, Nan MM, Fu CL, Huang WM, Kong LY, and Xu WJ
- Subjects
- Mice, Molecular Structure, RAW 264.7 Cells, Animals, Nitric Oxide metabolism, Stereoisomerism, China, Hypericum chemistry, Monoterpenes isolation & purification, Monoterpenes pharmacology, Phloroglucinol isolation & purification, Phloroglucinol pharmacology, Phloroglucinol chemistry, Phytochemicals pharmacology, Phytochemicals isolation & purification
- 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 IC
50 values of 7.07 ± 1.02 μM and 11.39 ± 0.24 μM, respectively., Competing Interests: Declaration of competing interest All authors declare that they have no conflict of interest., (Copyright © 2024 Elsevier B.V. All rights reserved.)- Published
- 2024
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