ABSTRACT
Nine new ent-kaurane diterpenoids, named scopariusols L-T (1-9), were isolated from the aerial parts of Isodon scoparius. Their structures were characterized mainly by analyzing the NMR and HR-ESI-MS data, and the absolute configuration of 1 was determined by single-crystal X-ray diffraction. Compound 1 was active against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW-480), and it also inhibited NO production in LPS-stimulated RAW264.7 cells, with an IC value of 0.6 μmol·L.
Subject(s)
Animals , Humans , Mice , Antineoplastic Agents, Phytogenic , Chemistry , Pharmacology , Cell Line, Tumor , Crystallography, X-Ray , Diterpenes, Kaurane , Chemistry , Pharmacology , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal , Chemistry , Pharmacology , HL-60 Cells , Isodon , Chemistry , Lipopolysaccharides , Pharmacology , Macrophages , Molecular Structure , Nitric Oxide , Nuclear Magnetic Resonance, Biomolecular , Plant Components, Aerial , ChemistryABSTRACT
Nine new ent-kaurane diterpenoids, named scopariusols L-T (1-9), were isolated from the aerial parts of Isodon scoparius. Their structures were characterized mainly by analyzing the NMR and HR-ESI-MS data, and the absolute configuration of 1 was determined by single-crystal X-ray diffraction. Compound 1 was active against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW-480), and it also inhibited NO production in LPS-stimulated RAW264.7 cells, with an IC value of 0.6 μmol·L.
Subject(s)
Animals , Humans , Mice , Antineoplastic Agents, Phytogenic , Chemistry , Pharmacology , Cell Line, Tumor , Crystallography, X-Ray , Diterpenes, Kaurane , Chemistry , Pharmacology , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal , Chemistry , Pharmacology , HL-60 Cells , Isodon , Chemistry , Lipopolysaccharides , Pharmacology , Macrophages , Molecular Structure , Nitric Oxide , Nuclear Magnetic Resonance, Biomolecular , Plant Components, Aerial , ChemistryABSTRACT
The present study was designed to determine the chemical constituents of EtOAc extracts of the aerial parts of Isodon wikstroemioides. Compounds 1-8 were isolated and purified by normal-phase silica gel and reversed-phase C18silica gel column chromatography and HPLC. Their structures were elucidated by extensive spectroscopic methods. Most of them were evaluated for their in vitro cytotoxicity against human cancer HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cells and their inhibitory activity against nitric oxide (NO) production in LPS-activated RAW264.7 macrophages. Among the eight 11, 20-epoxy-ent-kauranoids isolated, compounds 1-6 (isowikstroemins H-M) were new diterpenoids. Compounds 1, 3, and 7 exhibited significant cytotoxicity with IC50 values ranging from (0.84 ± 0.02) to (4.09 ± 0.34) μmol · L(-1), while compounds 4 and 5 showed selective cytotoxicity. In addition, compounds 1, 3, 4, and 7 exhibited inhibitory activity against nitric oxide (NO) production in LPS-activated RAW264.7 macrophages. These results provide a basis for future development of these compounds as anti-cancer and anti-inflammatory agents.
Subject(s)
Humans , Anti-Inflammatory Agents , Antineoplastic Agents, Phytogenic , Cell Line, Tumor , Diterpenes, Kaurane , Inhibitory Concentration 50 , Isodon , Chemistry , Lipopolysaccharides , Pharmacology , Macrophages , Metabolism , Neoplasms , Drug Therapy , Nitric Oxide , Phytotherapy , Plant Components, Aerial , Plant ExtractsABSTRACT
The aim of this study was to investigate the biological effect of longikaurin A on multiple myeloma H929 cells. Effects of oridonin and longikaurin A on proliferation of H929 cells were evaluated by CCK-8 assay. Cell morphological features of H929 cells were examined under inverted phase contrast microscope. Apoptosis was determined by Annexin V/PI staining. Expression of caspase-3, caspase-9, and PARP were detected by Western blot. Reactive oxygen species (ROS) level was determined by DCFDA assay. The results showed that longikaurin A (IC(50) 0.85 µmol/L) was more effective than oridonin ((IC(50) 10.66 µmol/L) to inhibit the proliferation of H929 cells. Treatment with longikaurin 2 µmol/L significantly increased the percentage of Annexin V positive cells. Caspase-3 and caspase-9 were activated and PARP, one substrate of caspase-3, was cleaved into 85 kDa fragments. The ROS scavenger N-acetyl-cysteine significantly blocked apoptosis induced by longikaurin A. However, longikaurin A did not increase the ROS level in H929 cells. It is concluded that longikaurin A is more effective than oridonin to induce apoptosis in multiple myeloma H929 cells without increasing the ROS level.
Subject(s)
Humans , Apoptosis , Caspase 3 , Metabolism , Caspase 9 , Metabolism , Cell Line, Tumor , Diterpenes, Kaurane , Pharmacology , Multiple Myeloma , Pathology , Reactive Oxygen Species , MetabolismABSTRACT
This paper reviewed the worldwide research progresses of the genus Laggera both on phytochemical and pharmacological work in the past few decades. The main secondary metabolites of this genus are proved to be sesquitepenoids, flavonoids and phenolic acids. Phamacological investigations revealed that the certain extracts of some Laggera species possess significant bioactivities on anti-inflammation, anti-tumor and anti-viral infection. This review afforded the comprehensive description of the active components as to provide useful references to elucidate their historical clinical application on upper respiratory infection, influenza, parotitis, and recurrent herpes viral infection.
Subject(s)
Animals , Humans , Anti-Inflammatory Agents, Non-Steroidal , Pharmacology , Therapeutic Uses , Antineoplastic Agents, Phytogenic , Pharmacology , Therapeutic Uses , Antiviral Agents , Pharmacology , Therapeutic Uses , Flavonoids , Chemistry , Therapeutic Uses , Influenza, Human , Drug Therapy , Molecular Structure , Parotitis , Drug Therapy , Phytotherapy , Plants, Medicinal , Chemistry , Ranunculaceae , Chemistry , Respiratory Tract Infections , Drug Therapy , Sesquiterpenes , Chemistry , Therapeutic UsesABSTRACT
This paper reviewed updated research progresses of caffeoylquinic acids both in phytochemical and pharmacological aspects. The resources, distribution as well as the chemical structures of monocaffeoylquinic acids, dicaffeoylquinic acids, tricaffeoylquinic acids and multicaffeoylquinic acids are conclusively analyzed. The reviewed pharmacological investigations indicated that the caffeoylquinic acids exhibited significant activities such as anti-oxidation, anti-inflammation, enzyme inhibition, hypatoprotective and anti-PAF effects. The broad distribution and the remarkably pharmacological activities of these natural phenolic acids indicated their potential in the discovery and development of new natural drugs.
Subject(s)
Animals , Humans , Anti-Bacterial Agents , Pharmacology , Anti-Inflammatory Agents, Non-Steroidal , Pharmacology , Antioxidants , Pharmacology , Antiviral Agents , Pharmacology , Chlorogenic Acid , Chemistry , Pharmacology , Enzyme Inhibitors , Pharmacology , Plant Leaves , Chemistry , Plants, Medicinal , Chemistry , Quinic Acid , Chemistry , PharmacologyABSTRACT
<p><b>OBJECTIVE</b>To study the chemical constituents from the rhizome of Impatiens pritzellii var. hupehensis.</p><p><b>METHOD</b>The rhizome were extracted with methanol, isolated and purified by column chromatography on silica gel. All the compounds were identified on the basis of spectral analysis (including IR, MS, NMR) and physico-chemical characters.</p><p><b>RESULT</b>Five compounds were identified as a-spinasterol (I), alpha-spinasteryl-7, 22-dien-3-O-beta-D-glucopyranoside (II), stigmast-7, 22-dien-3-one (III), stearic acid (IV), hentriantane (V).</p><p><b>CONCLUSION</b>Compound I is isolated from this plant for the first time, Compound II, III, IV, V are isolated from genus Balsaminaceae for the first time.</p>
Subject(s)
Impatiens , Chemistry , Plants, Medicinal , Chemistry , Rhizome , Chemistry , Stearic Acids , Chemistry , Stigmasterol , ChemistryABSTRACT
<p><b>OBJECTIVE</b>To isolate and identify compounds from Picria fel-tarrae in order to utilize it better.</p><p><b>METHOD</b>Constituents from Picria fel-tarrae were isolated by several column chromatography and their structures were elucidated on the basis of chemical and spectral analysis.</p><p><b>RESULT</b>Six compounds, N-benzoylphenylalanyl-L-phenylalaninol acetate (1), 1-hydroxy-7-hydroxymethyl-9,10-anthraquinone (2), 9, 16-dioxo-10,12,14-octadeca-trienoic acid (3), 5,7,4'-trihydroxy-flavone (4), beta-sitosterol (5), and daucosterol (6) were obtained from the fraction with relatively low polarity of EtOH extract of Picria fel-tarrae.</p><p><b>CONCLUSION</b>Compounds 1-6 were isolated from picria fel-tarrae Lour for the first time, and the 13C-NMR data of compounds 1-3 are provided firstly in the literature.</p>
Subject(s)
Apigenin , Chemistry , Dipeptides , Chemistry , Molecular Structure , Plants, Medicinal , Chemistry , Scrophulariaceae , Chemistry , Sitosterols , ChemistryABSTRACT
OBJECTIVE: A systematic study of Laggera pterodonta was performed in order to identify its bioactive compounds. METHODS: Solvent partition and column chromatography used to isolate and purify Laggera pterodonta compounds. The isolated compounds were further elucidated by high field NMR spectroscopy. RESULTS: Fifty-two compounds were separated and the structures of 39 compounds were elucidated. Twenty-four compounds have not been previously reported. For example, the structure of compound 19, a previously undetected compound was elucidated as 4gamma, 9alpha,11-triol-enantio-eudesmane using both 1D and 2D NMR spectroscopy. Major secondary metabolites of the Laggera pterodonta included eudesmane-type sesquiterpenes and flavone derivatives. CONCLUSION: A systematic study of a yunnan herbal medicine Laggera pterodonta resvealed several novel compounds that may have clinical significance. Further in vivo animal studies should be performed to assess their bioactive role.