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

A short terpene synthase gene was obtained by screening the transcriptome data of Senecio scandens. The phylogenetic tree and sequence alignment putatively identified this gene as a nerolidol synthase gene, named SsNES(GenBank MH518312). Protein homology modeling indicated that SsNES contained a complete conserved domain and folded correctly. SsNES was cloned and successfully expressed in Escherichia coli as soluble protein. The biochemical function of SsNES was characterized by E. coli metabolic engineering, which showed that SsNES catalyzed formation of trans-nerolidol with(E, E)-farnesyl diphosphate as the substrate. Nerolidol was also detected in stems and leaves of S. scandens, indicating that SsNES might act as the nerolidol synthase in plant. RT-PCR analysis indicated that SsNES was mainly expressed in stem, flowers and leaves, and no expression was observed in roots. After the treatment of SA, MeJA or Ala, SsNES was induced significantly at 6 h, indicating involvement in the defense response of S. scandens. The identification of SsNES not only clarified biosynthesis of nerolidol in S. scandens, but also provided diversity of sesquiterpene synthase, as well as theoretical basis for disease and pest defense mediated by the terpene metabolites.
Escherichia coli ; Genes, Plant ; Phylogeny ; Senecio ; enzymology ; Sesquiterpenes ; metabolism

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 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

As a secondary metabolite, sesquiterpenes are not only have important functions in plant defense and signaling, but also play potential roles in basic materials for pharmaceuticals, cosmetic and flavor. As a traditional Chinese herbal medicine, Senecio scandens exhibits effects of anti-inflammatory and immunosuppressive, as well as invigorating the blood and removing extravasated blood. Over 600 sesquiterpenes with diverse structures were isolated from S. scandens and related species in the same genus. To characterize sesquiterpenes synthesis, two FPS genes(SsFPS1 and SsFPS2) were identified in S. scandens through transcriptomic analysis. Bioinformatic analysis showed that both SsFPSs have conserved motifs for FPS function. Both SsFPSs exhibited constitutive gene expression in S. scandens tissues and SsFPS2 accumulated higher transcript in leaves and roots than SsFPS1. Meanwhile consistent with constitutive sesquiterpene accumulation in S.scandens tissues, most of these sesquiterpenes were detected in leaves and roots more than stems and flowers. Recombinant expression through Escherichia coli metabolic engineering, SsFPS1 or SsFPS2 was co-transformed with ZmTPS11(maize β-macrocarpene synthase) into BL21 competent cells. The results showed that the content of β-macrocarpene was increased by co-transformation with SsFPSs. It is demonstrated that SsFPS1 and SsFPS2 catalyzed E,E-FPP formation and provided FPP precursor for downstream sesquiterpene synthases. Characterization of SsFPSs provided the foundation for the exploration of biosynthesis of sesquiterpenoid with diverse structures and potential pharmaceutical values in S.scandens, and provide an important theoretical basis for the development of S. scandens abundant resources.
Cloning, Molecular ; Gene Expression Profiling ; Geranyltranstransferase ; Medicine, Chinese Traditional ; Senecio/genetics* ; Sesquiterpenes

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

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

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