A new eremophilane derivative, 4,5,11-trimethyl-9( 10), 7 ( 11) -eremophiladien-8-keto-12-carboxylic acid-beta-D-glucopyranoside( which named dianthuside A) 1 and four known compounds, 5,7,4'-trihydroxy-flavonone-3-0-beta-D-glucoside (2), quercetin-3-0-beta-D-glucoside(3) ,hyperin(4) and rutin(5) have been isolated from the aerial part of Senecio dianthus. Their structures were elucidated by physicochemical properties and spectroscopic data analysis. Compounds 2, 4 and 5 were isolated from this plant for the first time.
Dianthus ; chemistry ; Glucosides ; analysis ; chemistry ; Rutin ; analysis ; chemistry ; Senecio ; chemistry

OBJECTIVETo investigate the chemical constituents from the whole plants of Senecio chrysanthemoides.

METHODThe chemical constituents were isolated and purified by chromatographic techniques over silica gel, Sephadex LH-20, preparative TLC and preparative HPLC. Structures of the compounds were identified by NMR and MS spectroscopic methods.

RESULTTwenty five compounds were obtained and their structures were elucidated as seneciphyline (1), senecionine (2) , 1,2-dihydrocacalohastine (3) , eu-desm-4( 15)-ene-1beta,6alpha-diol (4), 7,11,15-trimethyl- 3methylidenehexadecane-1,2-diol (5), faradiol 3-O-palmitate (6),maniladiol 3-O-palmitate (7), faradiol (8), maniladiol (9), beta-amyrin (10), alpha-amyrin (11), betulin (12), loranthol (13), (+)-syringaresinol (14) , 1-hydroxy-4-oxo-cyclohexane-1-acetate (15), 2, 6-dimethoxy-p-benzoquinone (16), stigmasta-5, 22-dien-3beta-hydroxy-7-one (17) , stigmasta-5, 22-dien-7-one (18) , stigmasta-4-en-3-one (19), stigmasta-4,22-dien-3-one (20), beta-sitosterol (21), stigmasterol (22), daucosterol (23), glycerol 1-hendecanoate (24), and methyl hendecanoate (25).

CONCLUSIONCompounds 5-9,13, 17-20 and 24 were obtained from the genus Senecio for the first time.

Acetates ; chemistry ; Chemical Fractionation ; Plant Extracts ; analysis ; isolation & purification ; Senecio ; chemistry

OBJECTIVETo investigate the chemical constituents from the whole plants of Senecio chrysanthemoides.

METHODConstituents were isolated by using a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and ODS C18, as well as reversed-phase HPLC. Structures of the isolates were identified by spectroscopic and chemical methods.

RESULTEighteen glycosides were obtained from a H2O-soluble portion of an ethanolic extract of the whole plants of Senecio chrysanthemoides and their structures were elucidated as 5'-methoxyligusinenoside B (1), hyuganoside III b (2), citrusin A (3), alaschanioside A (4), citrusin B (5), dehydrodieoniferyl alcohol 4, gamma'-di-O-beta-D-glucopyranoside (6), osmanthuside G (7), syringin (8), dehydrosyringin (9), 2-(4-hydroxy-3,5-dimethoxyphenyl) ethanol 4-O-beta-D-glucopyranoside (10), 2-phenylethyl beta-gentiobioside (11), phenethyl beta-D-glucopyranoside (12), nikoenoside (13), benzyl beta-D-glucopyranoyl (1 --> 6 ) -beta-D-glucopyranoside (14), 3,5-dimethoxy-4-hydroxybenzyl alcohol 4-O-beta-D-glucopyranoside (15), icariside B2 (16), sonchuionoside C (17), and 1-[(beta-D-glucopyranosyloxy) methyl] -5,6-dihydropyrrolizin-7-one (18).

CONCLUSIONCompound 1 was a new lignan glycoside, and the remaining compounds were obtained from this plant for the first time.

Chromatography ; methods ; Glycosides ; chemistry ; isolation & purification ; Lignans ; chemistry ; isolation & purification ; Plant Extracts ; chemistry ; Plants, Medicinal ; chemistry ; Senecio ; chemistry

OBJECTIVETo study the pyrrolizidine alkaloids of Senecio cannabifolius var. integrilifolius.

METHODVarious chromatographic methods were used for the isolation and purification of chemical constitutents of the plant and their structures were elucidated on the basis of spectral analysis.

RESULTFour compounds were determinated as jacobine(1), jacoline(2), jaconine(3), senecicannabine(4).

CONCLUSIONAll compounds were isolated from this plant for the first time.

Drugs, Chinese Herbal ; analysis ; isolation & purification ; Pyrrolizidine Alkaloids ; analysis ; isolation & purification ; Senecio ; chemistry

OBJECTIVETo develop an HPLC method for fingerprint study of both Senecio scandens and S. scandens.

METHODFingerprints of the two Senecio herbs were compared. And the concentrations of main peaks in them were semi-quantified as chlorogenic acid or hyperoside. Chromatography was performed on a Shiseido Capcell Pak MG II C18 (4.6 mm x 250 mm, 5 microm) column using a gradient elution of acetonitrile-water containing 0.2% acetic acid. And detection wavelength was 360 nm.

RESULTSignificant difference was found in the fingerprint of the two herbs. Eleven peaks were picked out for the evaluation of S. scandens and S. scandens, respectively. They were identified to be either organic acid compounds or flavones by HPLC-UV and LC-ESI-MS analysis. And semi-quantification of them showed the concentrations of organic acid compounds and flavones in S. scandens were 2.29- and 15.56- folds of those in S. scandens, respectively.

CONCLUSIONThe developed HPLC method is suitable for the fingerprint study for both of S. scandens and S. scandens. It is robust and producible enough to be used for the quality evaluation on S. scandens.

Chlorogenic Acid ; analysis ; Chromatography, High Pressure Liquid ; methods ; Quercetin ; analogs & derivatives ; analysis ; Senecio ; chemistry

OBJECTIVETo develop an UPLC-MS method for the simultaneously quantitation of adonifoline and senecinine in Senecio herbs.

METHODUPLC-Micro 2000 was used for quantification in SIR mode under ESI+. Monocrotaline was used as the internal standard. Chromatography was performed on a Shiseido Capcell Pak MG (2.0 mm x 50 mm, 3 microm) column at 30 degrees C using an gradient elution of acetonitrile-0.5% formic acid in water at the flow rate of 0.3 mL x min(-1). The injection volume was 2 microL.

RESULTGood linearity was obtained for quantitation of adonifoline over the range of 1.02-816.00 microg x L(-1) (r = 0.998 0). And recoveries at different concentration levels were between 95.73% and 103.0% with RSDs no more than 2.5%. For quantification of senecionine, the linear range was between 1.08-860.56 microg x L(-1) (r = 0.997 6). And recoveries at different concentration levels were between 95.67% and 101.5% with RSDs no more than 2.3%. Good reproducibility and precision were also achieved.

CONCLUSIONThe new developed UPLC method is sensitive, accurate and reliable enough for the quantitation of adonifoline and senecionine in Senecio herbs thus can be used for the limit detection of pyrrolizidne alkaloids in S. scandens. It can also be used for the identification of fake drugs of S. scandens such as S. vulgaris. The developed method was served for the quality evaluation of Herba Senecionis Scandentis.

Chromatography, Liquid ; methods ; Lactones ; analysis ; Mass Spectrometry ; methods ; Pyrrolizidine Alkaloids ; analysis ; Senecio ; chemistry

OBJECTIVETo isolate the constituents of Senecio scandens and determine their structures.

METHODComponds were isolated and purified by silica gel column chromatography and the structures were identified by spectroscopic methods.

RESULTNine compounds were isolated as lupenone (1) , oleanane (2) , beta-sitosterol (3) , daucosterol (4) , adonifoline (5) , phydroxy benzeneacetic acid (6) , 2-(1,4-dihydroxy-cyclohexanyl) -acetic acid (7), hyperoside (8), linarin (9).

CONCLUSIONThese compounds were obtained from S. scandens for the first time except 4 and 6.

Glycosides ; chemistry ; isolation & purification ; Plant Extracts ; chemistry ; isolation & purification ; Plants, Medicinal ; chemistry ; Quercetin ; analogs & derivatives ; chemistry ; isolation & purification ; Senecio ; chemistry ; Triterpenes ; chemistry ; isolation & purification

The purpose of this study is to evaluate the embryotoxicity of alkaloids in Senecionis Scandentis Hebra on in vitro cultured mouse embryos. Mouse whole embryo culture (WEC) was applied in this study. Post-implantation (8.5 d) mouse embryos were isolated from their mothers, and cultured in medium of immediately centrifuged serum (ICS) with different concentrations of seneciphylline (target concentrations were 100, 50, 25 and 12.5 μg x mL(-1)) or senkirkine (target concentrations were 50, 25 and 12.5 μg x mL(-1)) for 48 h. After culturing completed, the development and organic morphodifferentiation of the cultured embryos were evaluated microscopically. Treatment with seneciphylline and senkirkine had adverse effects on the development and organic morphodifferentiation of embryos. The effect also had clear dose-response. Alkaloidals in Senecionis Scandentis Hebra had embryotoxicity on cultured embryos, which indicated that pregnant people exposed to Senecionis Scandentis Hebra may get potential risk on fetus.
Animals ; Embryo Culture Techniques ; Embryo, Mammalian ; drug effects ; Female ; Mice ; Pregnancy ; Pyrrolizidine Alkaloids ; toxicity ; Senecio ; chemistry ; Teratogens ; toxicity

Pyrrolizidine alkaloids(PAs) are a kind of natural toxins, which can cause severe hepatotoxicity, pulmonary toxicity, genotoxicity, neurotoxicity, embryotoxicity and even death. Therefore, international organizations and countries such as World Health Organization have paid great attention to herbal medicines and preparations containing PAs. PAs are widely distributed in Chinese herb medicines and contained in hundreds of traditional Chinese medicine preparations. The content of adonifoline, the main PAs in Senecionis Scandentis Herba, shall be less than 0.004% in herbal medicines as described in Chinese pharmacopeia. However, there is no guidance in preparations which contain Senecionis Scandentis Herba. In this study, 14 preparations were analyzed by an UPLC-MS method. Among them, 8 preparations were found to contain adonifoline much higher than the content limits of such countries as Germany, Netherlands and New Zealand. And the highest contents of adonifoline were found in Qianbai Biyan Tablets and Qianbai Biyan Capsules, which are officially recorded in Chinese Pharmacopeia. The contents of adonifoline varied in different batches of the same preparations. The highest content was 156.10 μg·g~(-1) Qianbai Biyan Tablets, whose daily intake of adonifoline was up to 1 030.26 μg according to the recommended dosage of the preparation. Our results showed the potential risk of these preparations, and the content limit of adonifoline shall be inspected Chinese medicine preparations containing Senecionis Scandentis Herba.
Chromatography, Liquid ; Drugs, Chinese Herbal/standards* ; Lactones/analysis* ; Medicine, Chinese Traditional ; Pyrrolizidine Alkaloids/analysis* ; Senecio/chemistry* ; Tandem Mass Spectrometry

OBJECTIVETo investigate activity-guided isolation and identification of anti-Staphylococcus aures components from Senecio tenuifolius Burm. F. (S. tenuifolius).

METHODSHexane, chloroform, ethyl acetate, methanol and aqueous extracts of S. tenuifolius were prepared by soxilation for antimicrobial activity against one registered Staphylococcus aureus (S. aureus) (ATCC No: 25923) and two clinical isolates, methicillin resistant and methicillin sensitive S. aureus. NCCL standard methods were followed for antibacterial activity. GC-MS was performed to identify the chemical composition of bio active fraction.

RESULTSAmong all solvent extracts, methanol extract significantly reduced the growth of S. aureus (ATCC No: 25923), methicillin resistant and methicillin sensitive S. aureus with the best zone of inhibition at 16.23, 14.06 and 15.23 mm and minimum inhibition concentration (MIC) values at 426.16, 683.22 and 512.12 µg/mL, respectively. In order to detect the active component in methanol extract, it was further purified by column chromatography, which yielded four fractions (St1, St2, St3, and St4). Among these four fractions, St3 was effective against the tested strains of S. aures, with the best zone of inhibition at 15.09, 13.25 and 14.12 mm and with best MIC values at 88.16, 128.11 and 116.12 µg/mL, respectively. Effective fraction partially purified from S. tenuifolius (St3) yielded MIC's that were at least 20 fold less when compared to crude extract. GC-MS analysis of St3 revealed the presence of 3-[methyl-6,7-dihydro benzofuran-4 (5H)-one], 1,2-benzenedicarboxylic acid, hydroquinone, methyl ester and 3 unknown compounds.

CONCLUSIONSThe study provides scientific evidence for traditional and folklore medicinal use of S. tenuifolius in skin infections treatment.

Anti-Bacterial Agents ; pharmacology ; Gas Chromatography-Mass Spectrometry ; India ; Microbial Sensitivity Tests ; Plant Extracts ; pharmacology ; Plant Leaves ; chemistry ; Senecio ; chemistry ; Staphylococcus aureus ; drug effects