Phytochemical analysis of the peeled stems of Syringa pinnatifolia Hemsl. led to the discovery of 13 undescribed lignans, namely helanols A and B (1 and 2) and alashanenols W-G (3-13), as well as four known analogues, of which helanols A and B were lignans with novel skeleton of α-β' linkage. The structures were unambiguously established by extensive spectroscopic analyses, NMR calculations, ECD calculations, and single crystal X-ray crystallography. Five lignans (1, 2, 5, 11 and 13) exhibited a moderate protective effect against HO-induced oxidative injuries in H9c2 cells with the protective rates of 11.3-20.6 % at the concentration of 0.3-20 μM, while the positive control quercetin showed protective rates of 58.7 % at 10 μM. Further mechanism investigation suggested that 1 and 2 exerted the protective effect by regulating the expression of Nrf2/HO-1.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1016/j.bioorg.2024.107732 | DOI Listing |
Chem Biodivers
November 2024
Research Center for Traditional Chinese Medicine Resources and Ethnic Minority Medicine, Jiangxi University of Chinese Medicine, Nanchang, 330004, PR China.
As a part of systematic research, an ongoing phytochemical investigation of the sesquiterpenoid-containing fraction led to the isolation of five new sesquiterpenoids from the peeled stems of Syringa pinnatifolia, including two pairs of enantiomeric humulane-type (±)-alashanoids A and B (1 and 2) and one eremophilane-type alashanoid C (3). These structures were elucidated by the analysis of extensive spectroscopic data, including ESI-MS and 1D and 2D NMR, and the absolute configuration was determined by comparing its experimental and calculated electronic circular dichroism and calculated NMR. These isolates exhibited moderate in vitro cardioprotective effects against oxidative injuries in H9c2 cells.
View Article and Find Full Text PDFBioorg Chem
November 2024
Modern Research Center for Traditional Chinese Medicine, Beijing Research Institute of Chinese Medicine, Beijing University of Chinese Medicine, Beijing 102488, PR China; Research Center for Traditional Chinese Medicine Resources and Ethnic Minority Medicine, Jiangxi University of Chinese Medicine, Nanchang 330004, PR China. Electronic address:
Phytochemical analysis of the peeled stems of Syringa pinnatifolia Hemsl. led to the discovery of 13 undescribed lignans, namely helanols A and B (1 and 2) and alashanenols W-G (3-13), as well as four known analogues, of which helanols A and B were lignans with novel skeleton of α-β' linkage. The structures were unambiguously established by extensive spectroscopic analyses, NMR calculations, ECD calculations, and single crystal X-ray crystallography.
View Article and Find Full Text PDFChem Biodivers
November 2024
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 102448, P. R. China.
Four new norlignans, noralashinols D-F (1a/b-3), and two known analogues (4 and 5) were isolated from the peeled stems of Syringa pinnatifolia Hemsl. The structures were elucidated by analysis of spectroscopic data, such as IR, HR-ESI-MS, 1D and 2D NMR, and ECD. All compounds were evaluated for anti-inflammatory activities against NO production induced by LPS in BV microglia cells.
View Article and Find Full Text PDFPlant Biotechnol J
September 2024
State Key Laboratory for Quality Ensurance and Sustainable Use of Dao-di Herbs, National Resource Center for Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing, China.
Phytochemistry
May 2024
Modern Research Center for Traditional Chinese Medicine, Beijing Research Institute of Chinese Medicine, Beijing University of Chinese Medicine, Beijing, 102488, PR China. Electronic address:
A continued phytochemical investigation guided by H NMR and LC-MS data on the ethanol extract from the peeled stems of Syringa pinnatifolia Hemsl. led to the isolation of 16 undescribed dimeric eremophilane sesquiterpenoids, namely syringenes R-Z (1-9) and A-G (10-16). These structures were elucidated by extensive analysis of spectroscopic data, including HRESIMS, NMR, quantum-mechanics-based computational analysis of NMR chemical shifts, and single-crystal X-ray diffraction analyses, and a concise rule for determination of relative configuration of angular methyl was proposed.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!