A phytochemical investigation guided by H NMR and LC-MS data on the ethanol extract of Syringa pinnatifolia stems led to the isolation of 11 new dimeric eremophilane sesquiterpenoids, namely, syringenes A-K (1-11) and one known analog (12, syringene L). These structures were elucidated by extensive analysis of spectroscopic data, single-crystal X-ray diffraction, and computational methods. Biological assays revealed that 1-12 exhibited different degrees of anti-inflammatory effects, and 5 and 6 showed significant cytotoxicity against human hepatoma HepG2 cells with IC values of 12.3 and 12.9 μM, respectively. Furthermore, flow cytometry assays and western blot analysis revealed that 5 and 6 promoted the apoptosis of HepG2 cells by activating ERK. Finally, the molecular docking analysis implied that the carbonyl and hydroxy groups at the C-11/C-6' of 5 and 6 had a good binding affinity with ERK.
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http://dx.doi.org/10.1016/j.bioorg.2022.105879 | DOI Listing |
Phytochemistry
April 2025
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China; University of Chinese Academy of Sciences, Beijing, 100049, China. Electronic address:
Two unprecedented sesquiterpene and monoterpene heterodimers and ten previously undescribed sesquiterpenoids, artemordosins A-L (1-12), as well as ten known sesquiterpenoids (13-22), were obtained from Artemisia ordosica. Their structures were elucidated based on comprehensive analyses of NMR, IR, HRESIMS, GIAO NMR calculations with DP4+ probability analysis, and ECD calculations. Notably, artemordosins A and B (1 and 2) were the first examples of cadinane-monoterpene dimers, and artemordosin A (1) was a cadinane-myrceane heterodimer with a 6/6/6/6 ring system formed by [4 + 2] cycloaddition, while artemordosin B (2) was a 4,5-seco-cadinane-artemisane dimer connected through a C-5-O-C-4' linkage.
View Article and Find Full Text PDFPhytochemistry
March 2025
College of Plant Protection, Hunan Agricultural University, Changsha, 410128, China. Electronic address:
Two heterocyclic sesquiterpenoid oligomers (1, 2) and four previously undescribed seco-pseudoguaianolide derivatives (3-6) were isolated from the inflorescence of Ambrosia artemisiifolia. Ambrosiadimer A (1) is an unprecedented dimer featuring a hexahydropyrrolizine core scaffold and two pseudoguaianolide units. Ambrosiatrimer A (2) is a trimer formed from three pseudoguaianolide units via a pyrrolidine ring.
View Article and Find Full Text PDFChin J Nat Med
November 2024
State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; Yunnan Characteristic Plant Extraction Laboratory, Kunming 650106, China. Electronic address:
Bioorg Chem
December 2024
Istituto di Scienze e Tecnologie Chimiche ''Giulio Natta'' - SCITEC, Consiglio Nazionale delle Ricerche, Via Mario Bianco 9, 20131 Milano, Italy. Electronic address:
Leishmaniasis and malaria are two debilitating protozoan diseases affecting millions globally, particularly in tropical and subtropical regions. Current therapeutic options face significant challenges due to emerging drug-resistant strains, necessitating the discovery of novel antiprotozoal agents. This study explores, for the first time, the antiprotozoal potential of calamenenes and their dimers, naturally occurring sesquiterpenes found in essential oils, through a novel chemo-enzymatic synthesis approach.
View Article and Find Full Text PDFJ Environ Sci (China)
April 2025
State Key Laboratory of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China; Hefei National Laboratory, Hefei 230088, China. Electronic address:
Elucidating the mutual effects between the different volatile organic compounds (VOCs) is crucial for comprehending the formation mechanism of atmospheric secondary organic aerosols (SOA). Here, the mixed VOCs experiments of isoprene and Δ-carene/β-caryophyllene were carried out in the presence of O using an indoor smog chamber. The suppression effect of isoprene was recognized by the scanning mobility particle sizer spectrometer, online vacuum ultraviolet free electron laser (VUV-FEL) photoionization aerosol mass spectrometry, and quantum chemical calculations.
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