AI Article Synopsis
Article Abstract
Seven new cadinane sesquiterpenes, (-)-(1R,6S,7S,10R)-1-hydroxycadinan-3-en-5-one (1), (+)-(1R,5S,6R,7S, 10R)-cadinan-3-ene-1,5-diol (2), (+)-(1R,5R,6R,7S,10R)-cadinan-3-ene-1,5-diol (3), (+)-(1R,5S,6R,7S,10R)-cadinan-4(11)-ene-1,5-diol (4), (+)-(1R,5R,6R,7R,10R)-cadinan-4(11)-ene-1,5,12-triol (5), (-)-(1R,4R,5S,6R,7S, 10R)-cadinan-1,4,5-triol (6), and (-)-(1R,6R,7S,10R)-11-oxocadinan-4-en-1-ol (7), together with nine known compounds were isolated from the brown alga Dictyopteris divaricata. The structures of the new natural products, as well as their absolute configuration, were established by means of spectroscopic data including IR, HRMS, 1D and 2D NMR, single-crystal X-ray diffraction, and CD. All compounds were inactive against several human cancer cell lines including lung adenocarcinoma (A549), stomach cancer (BGC-823), breast cancer (MCF-7), hepatoma (Bel7402), and colon cancer (HCT-8) cell lines.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/np040099d | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Artemordosins A-L, cadinane-monoterpene heterodimers and sesquiterpenoids with antihepatoma activity from Artemisia ordosica.
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 PDFA new cadinane-type sesquiterpenoid glucoside from .
Nat 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 PDFSpiro-meroterpenoids, Syzygioblanes D-H, Isolated from Indonesian Medicinal Plant .
J 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 PDFSesquiterpenes from the aerial parts of Artemisia vachanica krasch. ex poljakov and their anti-inflammatory and anti-diabetic activities.
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.
View Article and Find Full Text PDFStructurally diversified sesquiterpenoids from Chloranthus henryi and their neuroprotective activities on HO damaged PC12 cells.
Phytochemistry
January 2025
School of Pharmacy, Jiangxi University of Chinese Medicine, Nanchang, 330004, PR China. Electronic address:
Fifteen undescribed sesquiterpenoid monomers, including six pairs of sesquiterpenoid enantiomers (1a/1b-3a/3b and 5a/5b-7a/7b) and three analogues (4, 8, and 9), together with two known sesquiterpenoid dimers (10 and 11) were isolated from the whole plant of Chloranthus henryi Hemsl. Their structures were characterized by spectroscopic data analysis, ECD calculations, and single crystal X-Ray diffractions. Compounds 1a and 1b were highly aromatic cadinane-type sesquiterpenoids.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!