Back to Search
Start Over
Bioactive Sesquiterpenoids from the Peeled Stems of Syringa pinnatifolia.
- Source :
-
Journal of natural products [J Nat Prod] 2018 Aug 24; Vol. 81 (8), pp. 1711-1720. Date of Electronic Publication: 2018 Jul 19. - Publication Year :
- 2018
-
Abstract
- Fourteen new sesquiterpenoids, alashanoids A-H (1, 2, and 4-9), (+)-2,9-humuladien-6-ol-8-one (3b), and five pairs of enantiomers (1 and 4-7), along with eight known analogues (3a and 10-16) were isolated from the stems of Syringa pinnatifolia. The structures were established using IR, UV, MS, and NMR data. The absolute configurations of the new compounds were resolved by X-ray diffraction, a modification of Mosher's method, and experimental and calculated ECD data analysis. The new sesquiterpenoids represent three skeletons: a rare 2,2,5,9-tetramethylbicyclo[6.3.0]-undecane (1), a humulane-type (2-8), and a caryophyllene-type (9) skeleton. Compounds 6a, 7, and 11 showed protective effects against hypoxia-induced injury to H9c2 cells at a concentration of 40 μM, and 5-7, 11, and 13 inhibited NO production in LPS-induced RAW264.7 macrophage cells with IC <subscript>50</subscript> values ranging from 13.6 to 70.6 μM. These compounds decreased the TNF-α and IL-6 levels in RAW264.7 cells in a concentration-dependent manner at 20-80 μM.
- Subjects :
- Animals
Apoptosis drug effects
Cell Line
Cell Survival drug effects
Humans
Interleukin-6 metabolism
Magnetic Resonance Spectroscopy
Mass Spectrometry
Mice
Molecular Structure
Nitric Oxide biosynthesis
Plant Bark chemistry
RAW 264.7 Cells
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet
Tumor Necrosis Factor-alpha metabolism
X-Ray Diffraction
Plant Stems chemistry
Sesquiterpenes chemistry
Sesquiterpenes pharmacology
Syringa chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6025
- Volume :
- 81
- Issue :
- 8
- Database :
- MEDLINE
- Journal :
- Journal of natural products
- Publication Type :
- Academic Journal
- Accession number :
- 30024153
- Full Text :
- https://doi.org/10.1021/acs.jnatprod.7b01071