Artemisia plants are well-known for their abundant sesquiterpene compounds, which encompass various structural types and exhibit a range of biological activities. In this study, a systematic investigation of Artemisia atrovirens revealed the presence of germacrane-type sesquiterpenes for the first time. This included the discovery of 10 new compounds and three known analogues, among which were two rare dimeric germacrane-type compounds. Their structures were fully characterized through a comprehensive analysis involving MS, IR, 1D- and 2D-NMR spectroscopic data, single crystal X-ray diffraction, density functional theory (DFT) NMR calculations, and time-dependent DFT electronic circular dichroism (TDDFT ECD) calculations. Furthermore, all isolated compounds were evaluated for their anti-inflammatory activity in LPS-stimulated RAW 264.7 murine macrophages. Compound 10 demonstrated a potent inhibitory effect on NO production, with an IC value of 4.01 ± 0.09 μM. This study highlights the diverse chemical repertoire of Artemisia species and underscores their potential in drug discovery and development.
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http://dx.doi.org/10.1016/j.fitote.2024.106241 | DOI Listing |
Fitoterapia
December 2024
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; China-Serbia "Belt and Road" Joint Laboratory for Natural Products and Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China; School of Life Science and Technology, ShanghaiTech University, Shanghai 201210, China. Electronic address:
Artemisia plants are well-known for their abundant sesquiterpene compounds, which encompass various structural types and exhibit a range of biological activities. In this study, a systematic investigation of Artemisia atrovirens revealed the presence of germacrane-type sesquiterpenes for the first time. This included the discovery of 10 new compounds and three known analogues, among which were two rare dimeric germacrane-type compounds.
View Article and Find Full Text PDFNat Prod Res
October 2024
Institute of Traditional Chinese Medicine and Natural Products, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, China.
A new germacrane-type sesquiterpenoid () and a new alkamide (), as well as six known compounds (-) were isolated from the capitula of cv. Fubaiju. The new structures were elucidated by comprehensive spectroscopic analysis and quantum chemical calculations.
View Article and Find Full Text PDFJ Pharm Biomed Anal
September 2024
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, No. 38, Xueyuan Road, Beijing 100191, PR China. Electronic address:
Germacrone and curdione are germacrane-type sesquiterpenoids that are widely distributed and have extensive pharmacological activities; they are the main constituents of 'Xing-Nao-Jing Injection' (XNJ). Studies on the metabolic features of germacrane-type sesquiterpenoids are limited. In this study, the metabolites of germacrone and curdione were characterized by UHPLC-Q-Exactive Oribitrap mass spectrometry after they were orally administered to rats.
View Article and Find Full Text PDFChin J Nat Med
June 2024
State Key Laboratory of Drug Research & Natural Products Research Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; University of Chinese Academy of Sciences, Beijing 100049, China; Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan 528400, China. Electronic address:
Nine new germacranolides, sylvaticalides A-H (1-9), and three known analogues (10-12) were isolated from the aerial part of Vernonia sylvatica. Their structures were established using comprehensive spectroscopic analysis, including high-resolution electrospray ionization mass spectroscopy (HR-ESI-MS) and 1D and 2D nuclear magnetic resonance (NMR) spectra. Their absolute configurations were determined by X-ray diffraction experiments.
View Article and Find Full Text PDFBioorg Chem
September 2024
Chongqing Key Laboratory of New Drug Screening from Traditional Chinese Medicine, Integrative Science Center of Germplasm Creation in Western China (Chongqing) Science City & Southwest University, SWU-TAAHC Medicinal Plant Joint R&D Centre, College of Pharmaceutical Sciences, Southwest University, Chongqing 400715, PR China; Key Laboratory of Luminescence Analysis and Molecular Sensing, Ministry of Education, College of Pharmaceutical Sciences, Southwest University, Chongqing 400715, PR China. Electronic address:
(±)-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.
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