Chemical investigation of the aerial parts of led to the isolation of eight sesquiterpenoids and ten diterpenoids, including five cadinane sesquiterpenoids (-), three bisabolene sesquiterpenoids (), nine -kaurane diterpenoids (-), and an abietane diterpenoid (). Among them, are new and feature a rare lactone or furan ring derived from C-6 isopropyl group side chain. Compound was isolated from genus for the first time, and was also the first example of abietane-type diterpenoids from this plant. Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HRESIMS, and ECD). All compounds were examined for their inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 macrophage cells, and compound exhibited pronounced inhibition on NO production (IC = 11.04 M), being comparable to the positive control, quercetin (IC = 11.15 M).
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http://dx.doi.org/10.1080/14786419.2019.1586691 | DOI Listing |
Phytochemistry
December 2024
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 PDFNat Prod Res
December 2024
Chemistry of Medicinal Plants Department, National Research Centre, Giza, Egypt.
A new cadinane-type sesquiterpene glucoside, 10-hydroxy, 1(H), 6(H), 7(H), 8(H)-cadinane-4-en-8-O--D-glucoside () as well as, 2 known analogues [sinaicin ()- linichlorinA ()], were isolated from the CHCl:MeOH organic extract of . Chemical structures of all isolated compounds were established depending upon the spectroscopic data including, 1D and 2D NMR and HRMS. Colo-205 (colorectal cancer), HepG2 (hepatocellular carcinoma) and MCF-7 (breast adenocarcinoma) and cancer cell lines were used to test the cytotoxic potential of the isolated compounds (-).
View Article and Find Full Text PDFJ Nat Prod
December 2024
School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa 920-1192, Japan.
Syzygioblanes A-C (-), isolated from the Indonesian traditional herbal medicine (), are meroterpenoids with a spiro ring formed through a [4 + 2] cycloaddition of the flavanone desmethoxymatteucinol with cyclic sesquiterpenoids. Our ongoing phytochemical investigation of resulted in the isolation of five additional spiro-meroterpenoids, syzygioblanes D-H (-), which are hybrids of the same flavanone with eudesmane/cadinane-type sesquiterpenoids. A possible biosynthetic pathway involves enzymatic dearomative hydroxylation of desmethoxymatteucinol followed by [4 + 2] cyclization of the resulting diene with a cyclic sesquiterpene containing an exocyclic methylene to form the unique spiro ring in the syzygioblane molecule.
View Article and Find Full Text PDFChem Biodivers
November 2024
Key Laboratory of Tropical Biological Resources of Ministry of Education, School of Pharmaceutical Sciences, Hainan University, Haikou, Hainan, China.
Phytochemistry
February 2025
State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization and The Key Laboratory of Plants Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, China; University of Chinese Academy of Sciences, Beijing, 100049, China; College of Pharmacy, Xinjiang Medical University, Urumqi 830011, China. Electronic address:
Eleven undescribed sesquiterpenes, vachanins A-K covering types of germacrane, eudesmane, guaiacane, and cadinane, along with fifteen known analogs were isolated from the aerial parts of Artemisia vachanica Krasch. ex Poljakov. Their structures were established on the basis of HRMS and NMR data, and their absolute configurations were successfully determined by single-crystal X-ray diffraction analysis, C-NMR calculations and DP4+ probability analysis, and ECD data in corporation with quantum chemical calculations.
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