ABSTRACT
A new cytisine-type alkaloid, along with five known alkaloids was obtained from the seeds of Sophora alopecuroides. Their structures were determined to be (-)-N-(2'-hydroxy-3',5'-di-tert-butyl-toluene)-cytisine (1), (-)-lupanine (2), (+)-matrine (3), (+)-sophoramine (4), (+)-lehmannine (5) and (-)-sophocarpine (6). Their structures were established by NMR, ECD and HRESIMS data analyses. Their cytotoxicity effects against five human tumor cell lines were tested by MTT assay. Compound 1 has showed a wide range of cytotoxicity activities against varied tumor cells in vitro.
Subject(s)
Alkaloids , Sophora , Alkaloids/chemistry , Humans , Seeds/chemistry , Sophora/chemistryABSTRACT
Nine new ent-pimarane-type diterpenoids, siegesbeckia A-I (1-9), together with four known analogues ent-3α,15,16,19-tetrahydroxypimar-8(14)-ene (10), 15,16-dihydroxypimar-8(14)-en-3-one (11), 14ß,16-epoxy-7-pimarene-3α,15ß-diol (12) and darutigenol (13), were obtained from the aerial parts of Siegesbeckia glabrescens Makino. The structures of these compounds were elucidated by the interpretation of HRESIMS, 1D NMR and 2D NMR data. Their configurations were determined by ECD analysis and the structure of compound 1 was confirmed by X-ray crystallography. Putative biosynthetic pathways were proposed for 1-13. The anti-inflammatory effects of the compounds were evaluated by testing their inhibition of LPS-induced NO production in BV2 microglial cells. The results revealed that new compounds 2, 6 and 8 exhibited potent inhibitory activities with IC50 values of 33.07, 42.39 and 63.26⯵M, which compared well with the positive control minocycline (IC50 32.84⯵M).
Subject(s)
Abietanes/pharmacology , Anti-Inflammatory Agents/pharmacology , Asteraceae/chemistry , Nitric Oxide/antagonists & inhibitors , Abietanes/chemistry , Abietanes/isolation & purification , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Cell Line , Crystallography, X-Ray , Dose-Response Relationship, Drug , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Mice , Models, Molecular , Molecular Structure , Nitric Oxide/biosynthesis , Structure-Activity RelationshipABSTRACT
Three new isoflavone glucosides, kudonol A-C (1-3), two new ester derivatives of phenylpropanoid, kudolignan A and B (4-5) and five known compounds, (-)-maackiain (6), neoliquiritin (7), methyl 4-coumarate (8), methyl ferulate (9) and (+)-wikstromol (10), were isolated from an extract of dried seeds of the traditional Chinese medicinal plant Sophora alopecuroides L. Their structures were established by NMR and HRESIMS data analyses. The monosaccharide part's configuration of isoflavone glucosides was confirmed by acid hydrolysis and analyzed by a JAsco OR-4090 chiral detector, comparing it to standard substance D-glucose. The cytotoxicity effects against HeLa, Hep3B, MCF-7 and H1299 cells were tested by CCK-8 assay.
Subject(s)
Seeds/chemistry , Sophora/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Humans , Inhibitory Concentration 50 , Plant Extracts/pharmacology , Proton Magnetic Resonance SpectroscopyABSTRACT
A chemical investigation of Cynanchum mongolicum (Maxim.) Kom. identified 8 compounds. On the basis of spectroscopic data, they were determined to be 3 alkaloids and 5 sinapoyl esters, among which were two previously undescribed compounds (1 and 2). The inhibitory effects of the isolated compounds against four human tumor cell lines were evaluated in vitro by MTT assays, which revealed moderate inhibitory effects with IC50 values < 50 mM, in particularly, three antofine analogues have showed significant antitumor activities with IC50 values < 0.1 mM, which was obviously better than the 5-fluorouracil and potential to be used as cancer drugs.
