Some C-benzylated flavonoids based on gericudranin A were synthesized and evaluated their cytotoxic activities for the elucidation of structure-activity relationship. 2,4,6-Trihydroxyacetophenone was converted to target molecules in 6 approximately 7 steps via sequential protection, aldol condensation, cyclization, regioselective C-benzylation, and deprotection. The cellular growth inhibition of the synthetic C-benzylated flavonoids was investigated against sixteen human cancer cell lines. Among these compounds, 5b showed the most potent cytotoxicities against several cell lines, especially as potent as adriamycin against SNB19 cell lines with an IC(50) value of 0.7 microM.
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http://dx.doi.org/10.1007/s12272-009-1118-0 | DOI Listing |
Fitoterapia
October 2022
Faculty of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650050, PR China. Electronic address:
Two new C-benzylated chalcones, 2',4'-dihydroxy-3'-(2-hydroxylbenzyl) chalcone (1) and 2',4'-dihydroxy-5'-(2-hydroxybenzyl) chalcone (2), one new and one known mimosin-type homoisoflavonoid, mimosol H (7) and mimosol G (8), together with four known chalcones (3-6) and four known sappanin-type homoisoflavonoids (9-12), were isolated from the twigs and leaves of Caesalpinia digyna. Their structures were characterized by comprehensive spectroscopic analyses (including NMR and HRESIMS). Compounds 1, 2 and 8 exhibited moderate cytotoxicity against SMMC-7721, A-549 and/or MDA-MB-231 cell lines with IC values ranging from 11.
View Article and Find Full Text PDFJ Nat Prod
February 2020
Department of Chemistry and Molecular Biology , University of Gothenburg, SE-412 96 Gothenburg , Sweden.
A new meroisoprenoid (), two heptenolides ( and ), two -benzylated flavonoids ( and ), and 11 known compounds (-) were isolated from leaf, stem bark, and root bark extracts of ssp. by chromatographic separation. The structures of the new metabolites - were established by NMR, IR, and UV spectroscopic and mass spectrometric data analysis.
View Article and Find Full Text PDFMolecules
January 2020
Division of Chinese Materia Medica Development, National Research Institute of Chinese Medicine, Taipei 11221, Taiwan.
In folk medicine, Gagnep. has been used to treat diseases related to inflammation, ulcers, and cancer. There are no reports concerning the chemical components and bioactivities of ; thus, this study aims to explore the phytochemicals, quantify the main compounds, and test the anticancer activity of isolates from Dried rhizomes were extracted with 95% ethanol and, then, partitioned, fractionated, and isolated.
View Article and Find Full Text PDFAnticancer Res
December 2013
Division of Pharmacy Practice and Administration, Division of Medicinal Chemistry and Pharmacognosy, College of Phamacy, The OhioState University, 500 West 12th Avenue, Columbus, OH 43210-1291, U.S.A.
Background/aim: Dichamanetin is a C-benzylated flavanone isolated as a major secondary metabolite from Piper sarmentosum, a plant used as a spice in Southeast Asia. This study aimed to investigate the path through which dichamanetin exerts its antiproliferative effect.
Materials And Methods: The study of several signaling cellular components, namely, reactive oxygen species (ROS) levels, nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) transcription factor, mitochondrial membrane potential, DNA binding, poly ADP-ribose polymerase (PARP1) inhibition and proteasome inhibition was performed using an enzyme-linked immunosorbent (ELISA) assay, cell sorting, and western blot.
Planta Med
January 2013
Laboratory of Natural Products Chemistry, Faculty of Science and Technology, Phuket Rajabhat University, Muang, Phuket, Thailand.
Two new C-benzylated dihydrochalcone derivatives, 4,2',4'-trihydroxy-6'-methoxy-3'(2''-hydroxybenzyl)dihydrochalcone (1) and 2',4'-dihydroxy-4,6'-dimethoxy-3'(2''-hydroxybenzyl)dihydrochalcone (2), along with six known flavonoid derivatives (3-8), a known dihydrochalcone dimer (9), three known aromatic esters (10-12), and one known aromatic amide (13), were isolated from the leaves of Melodorum siamensis. The structures of the compounds were elucidated by spectroscopic analysis, mainly 1D and 2D NMR techniques (1H, 13C, COSY, HMQC, and HMBC), as well as by comparison with literature data. The isolated compounds with a sufficient amount for biological assays were evaluated for their antimalarial, antimycobactirial, and cytotoxic activities.
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