ABSTRACT
The bulbs of Lilium brownii var. viridulum (LB) are commonly used as both traditional Chinese medicines and popular functional food for many centuries in China. Previous studies reported that the extract of lily bulbs exhibited anti-inflammatory activity both in vivo and in vitro, but its active components and associated molecular mechanisms remain elusive. In the present study, using bioassay-guided isolation method, two phenylpropenoid acylglycerols, 1-O-feruloyl-2-O-p-coumaroylglycerol (1) and 1,3-O-diferuloylglycerol (2), were obtained and identified from the chloroform fraction of LB. Both compounds 1 and 2 significantly decreased the production of nitrite oxide (NO) in lipopolysaccharide (LPS)-stimulated mouse macrophage RAW264.7 cells in a dose-dependent manner with half maximal inhibitory concentration (IC50) values of 9.12 ± 0.72 µM and 12.01 ± 1.07 µM, respectively. They also inhibited the production of prostaglandin E2 (PGE2) and several other pro-inflammatory cytokines, such as interleukin-1ß (IL-1ß), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α). Furthermore, compounds 1 and 2 downregulated the protein levels of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). They also inhibited the nuclear translocation of nuclear factor-κB (NF-κB) p65 subunit and suppressed mitogen-activated protein kinases (MAPKs) pathway. Taken these data together, compounds 1 and 2 exhibited anti-inflammatory activities through acting on the NF-κB and MAPKs pathway. This research provides the first evidence on the major bioactive constituents and related molecular mechanisms of LB as an anti-inflammatory agent. Our findings also advanced the understanding of LB as a traditional herbal medicine for the prevention and treatment of inflammation.
Subject(s)
Anti-Inflammatory Agents/isolation & purification , Lilium/chemistry , NF-kappa B/metabolism , Plant Extracts/isolation & purification , Plant Roots/chemistry , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Dose-Response Relationship, Drug , Gene Expression Regulation/drug effects , Lipopolysaccharides/pharmacology , MAP Kinase Signaling System/drug effects , Mice , Nitric Oxide/metabolism , Plant Extracts/chemistry , Plant Extracts/pharmacology , RAW 264.7 CellsABSTRACT
During an ongoing exploration of potential anti-inflammatory agents from medicinal plants, eight new arylalkenyl α,ß-unsaturated δ-lactones, cryptoconcatones A-H (1-8), and two unusual arylalkenyl α,ß-unsaturated γ-lactones, cryptoconcatones I and J (9 and 10), were identified from the leaves and twigs of Cryptocarya concinna. The structures of these compounds were established based on spectroscopic data (MS, 1D/2D NMR), and their absolute configurations were determined with Riguera's method, the modified Mosher's method, chemical derivatization, and the Snatzke chirality rule. Compounds 4-6 and 8-10 showed inhibitory activity toward nitric oxide (NO) production in lipopolysaccharide-induced RAW 264.7 macrophages, particularly compounds 4 and 8-10, with IC50 values of 3.2, 4.2, 3.4, and 7.5 µM, respectively.
Subject(s)
Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents/pharmacology , Cryptocarya/chemistry , Drugs, Chinese Herbal/isolation & purification , Drugs, Chinese Herbal/pharmacology , Lactones/isolation & purification , Lactones/pharmacology , Animals , Anti-Inflammatory Agents/chemistry , Drugs, Chinese Herbal/chemistry , Lactones/chemistry , Lipopolysaccharides/pharmacology , Macrophages/drug effects , Mice , Molecular Structure , Nitric Oxide/antagonists & inhibitors , Nitric Oxide/biosynthesis , Nuclear Magnetic Resonance, Biomolecular , Plant Components, Aerial/chemistry , StereoisomerismABSTRACT
Relying on characteristic double UV absorptions (210 and 270 nm), sixteen phragmalins with three types of enolic acyl substituents at C-15 were isolated directly from EtOH extracts of the seeds of Chukrasia tabularis A. Juss. Eight of these compounds possessed a C-15-acetyl phragmalin skeleton, and the basic carbon skeleton and absolute configuration of one of these was determined by NMR and X-ray diffraction analysis, while the structures of the other phragmalins were determined via NMR, HR-MS, and CD spectra. Additionally, all of the isolates were tested for inhibition against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophages and cytotoxicity in SMMC-7721, MCF-7 and U2OS tumor cells.
Subject(s)
Limonins/chemistry , Meliaceae/chemistry , Animals , Cell Line/drug effects , Circular Dichroism , Crystallography, X-Ray , Drug Evaluation, Preclinical/methods , Humans , Limonins/pharmacology , Lipopolysaccharides/pharmacology , MCF-7 Cells/drug effects , Macrophages/drug effects , Macrophages/metabolism , Magnetic Resonance Spectroscopy , Mice , Molecular Structure , Nitric Oxide/metabolism , Spectrophotometry, UltravioletABSTRACT
Nine new tirucallane-type triterpenoids, ficutirucins A-I (1-9), were isolated from the fruit of Ficus carica. Their structures were established on the basis of spectroscopic data and chemical methods. All isolates were evaluated for their cytotoxic activities against three human cancer cell lines, MCF-7, HepG-2, and U2OS. Compounds 1-3, 6, 7, and 9 exhibited moderate cytotoxic activities with IC50 values of 11.67-45.61 µM against one or more of the three cancer cell lines.
Subject(s)
Cytotoxins/isolation & purification , Ficus , Fruit , Plant Extracts/isolation & purification , Triterpenes/isolation & purification , Cytotoxins/chemistry , Cytotoxins/pharmacology , Hep G2 Cells , Humans , MCF-7 Cells , Plant Extracts/chemistry , Plant Extracts/pharmacology , Triterpenes/chemistry , Triterpenes/pharmacologyABSTRACT
Six new polycyclic polyprenylated acylphloroglucinols, attenuatumiones A-F (1-6), together with twelve known analogs (7-18) were isolated from the whole plant of Hypericum attenuatum. Their structures were elucidated by spectroscopic methods, and the absolute configuration of C-13 in attenuatumione C (3) was deduced via the circular dichroism datum of the in situ formed [Rh2(OCOCF3)4] complexes. All isolates were evaluated for the cytotoxic activities on three human cancer cell lines. Compound 3 showed moderate cytotoxic activities with IC50 values of 10.12 and 10.56 µM against SMMC7721 and U2OS, respectively.