In the current study, nine flavonoids were isolated and purified from 75% ethanol extract of Selaginella uncinata (Desv.) Spring by column chromatographic techniques over macroporous resin, polyamide, silica gel, Sephadex LH-20 and pre-HPLC. On the basis of their physico-chemical properties and spectroscopic data analyses, these compounds were elucidated as cirsimarin (1), nepitrin (2), apigenin-6-C-α-L-arabinopyranosyl-8-C-β-D-glucopyranoside (3), apigenin-6-C-β-D-glucopyranosyl-8-C-α-L-arabinopyranoside (4), apigenin-7-O-β-D-glucopyranoside (5), 2,3-dihydroamentoflavone (6), 4'-O-methylamentoflavone (7), 2,3-dihydro-4'-O-methyl-amentoflavone (8), and 2,3,2",3"-tetrahydron-4'-O-methyl-robustaflavone (9). Compounds 1-5 belong to flavonoid glycosides and were isolated from the genus Selaginella for the first time.
Flavonoids ; analysis ; Selaginellaceae ; chemistry

Abstract: A new selaginellin derivative named as selaginellin S (1) was isolated from the whole plants of Selaginella pulvinata (Hook. et Grev.) Maxim. (Selaginellaceae), together with a known one (selaginellin M, 2). Compounds 1 and 2 were separated and purified by silica gel and Sephadex LH-20 column chromatography. Their structures were determined on the basis of extensive spectroscopic analysis including IR, MS, 1D and 2D NMR experiments, as well as ECD calculations. Compound 1 is a key intermidiant in the biosynthesis pathway of selaginellins. Compound 2 is first reported in this plant.
Biphenyl Compounds ; chemistry ; isolation & purification ; Cyclohexanones ; chemistry ; isolation & purification ; Molecular Structure ; Selaginellaceae ; chemistry

OBJECTIVETo establish a HPLC-DAD model for the simultaneous determination of two selaginellins (selaginellin and selaginellin B) and four biflavones (amentoflavone, sequoiaflavone, hinokiflavone and isocryptomerin) contained in 10 batches of Selaginella tamariscina and 12 batches of S. pulvinata produced in different areas.

METHODThe analysis was performed on a Waters Cosmosil C18 column (4.6 mm x 250 mm, 5 microm) eluted with acetonitril-0.1% formic acid as mobile phase in a linear gradient mode. The detection wavelength was set at 280, 337 nm. The flow rate was kept at 1.0 mL x min(-1), and the column temperature was 30 degrees C.

RESULTThe six active constituents showed significant different in content. Amentoflavone in S. tamariscina contains (5. 628-9. 184 mg x g(-1)) is more than that contained in S. pulvinata (0.823-7.131 mg x g(-1)), while selaginellin in S. pulvinata (0.123-0.593 mg x g(-1)) is more than that contained in S. tamariscina (0.067-0.133 mg x g(-1)). All the calibration curves showed good linear correlation coefficients (r > 0.9997) over the wide test ranges.

CONCLUSIONThe developed HPLC-DAD method is simple, sensitive and accurate and has the good repeatability in separation, which is available for the quality control of S. tamariscina and S. pulvinata.

Biflavonoids ; chemistry ; Biphenyl Compounds ; chemistry ; Chromatography, High Pressure Liquid ; methods ; Cyclohexanones ; chemistry ; Flavones ; chemistry ; Flavonoids ; chemistry ; Selaginellaceae ; chemistry

One new cyclopeptide was isolated from the ethyl acetate fraction of the 75% EtOH extract of Selaginella tamariscina by various column chromatography methods(HP-20, polyamide and semi-preparative HPLC). Its structure was identified as selapeptin A(1) by extensive spectroscopic analysis(HR-ESI-MS, 1 D and 2 D NMR). Compound 1 was evaluated for cytotoxic activities by MTT assay. It showed potent cytotoxic activity against B16 F10 with the inhibition rate of 51.57%±4.34% at 40 μmol·L~(-1) while had no impacts on MDA-MB-231 and MDA-MB-468 at 100 μmol·L~(-1).
Chromatography, High Pressure Liquid ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Peptides, Cyclic/pharmacology* ; Selaginellaceae/chemistry*

OBJECTIVETo establish a method to analyze HPLC fingerprint characteristics of 10 plants from Selaginella.

METHODHPLC was applied for establishment of fingerprints, which were used to evaluate and distinguish the different species of Selaginella.

RESULTThe different species from Selaginella showed different HPLC fingerprint characteristic. The samples of the same species but collected in different period, different environment or different locations showed certain difference in fingerprints

CONCLUSION2 important mutual fingerprint peaks were found in the 10 plants of Selaginella species and 5 peaks can be used as "main fingerprint peaks". The dates of these peaks can used for assessment of phylogenetic relation among species and evaluation of quality.

Biflavonoids ; analysis ; China ; Chromatography, High Pressure Liquid ; methods ; Plants, Medicinal ; chemistry ; classification ; Selaginellaceae ; chemistry ; classification ; Species Specificity

AIMTo study the chemical constituents of Selaginella tamariscina (Beauv.) Spring.

METHODSVarious chromatographic techniques were used to separate and purify the chemical constituents. Their physico-chemical properties and spectral data were used to elucidate the structures.

RESULTSFour compounds were isolated from the n-BuOH fraction of the water-extracts. Their structures were identified as 1-hydroxy-2-[2-hydroxy-3-methoxy-5-(1-hydroxyethyl)-phenyl]-3-(4-hydroxy-3,5-dimethoxy)-propane-1-O-beta-D-glucopyranoside (tamariscinoside B, I), adenosine (II), guanosine (III), arbutin (IV).

CONCLUSIONTamariscinoside B (I) is a new compound, while the others were isolated from Selaginella for the first time.

Adenosine ; chemistry ; isolation & purification ; Arbutin ; chemistry ; isolation & purification ; Glucosides ; chemistry ; isolation & purification ; Guanosine ; chemistry ; isolation & purification ; Molecular Conformation ; Molecular Structure ; Plants, Medicinal ; chemistry ; Selaginellaceae ; chemistry

AIM: To investigate the chemical constituents of Selaginella sinensis (Desv.) Spring. METHODS: Chromatographic separations on Diaion HP-20, silica gel, and Sephadex LH-20 were used. The structures of the isolates were elucidated on the basis of spectroscopic analysis, as well as chemical methods. RESULTS: Eight compounds were obtained and their structures were identified as sinensioside A (1), syringaresinol-4- O-β-D-glucopyranoside (2), (+)-medioresinol-4-O-β-D-glucopyranoside (3), pinoresinol-4, 4'-di-O-β-D-glucopyranoside (4), quercetin (5), eucomic acid (6), shikimic acid (7), and 2, 3-dihydroamentoflavone (8). CONCLUSION Compound 1 is a new dihydrobenzofuran sesquilignan glycoside from Selaginella sinensis.
Benzofurans ; chemistry ; isolation & purification ; Furans ; chemistry ; isolation & purification ; Glucosides ; chemistry ; isolation & purification ; Lignans ; chemistry ; isolation & purification ; Molecular Structure ; Plant Extracts ; chemistry ; Plant Stems ; chemistry ; Quercetin ; chemistry ; isolation & purification ; Selaginellaceae ; chemistry

OBJECTIVETo investigate the species, the distribution and the utilization of the medicinal plants from Selaginellaceae in Hubei Province.

METHODThrough field investigations and comparing the collected specimens and literatures, the classification and identification of the species in Hubei Province were studied.

RESULTThe results indicated that 15 species of plants from Selaginellaceae in Hubei, including 14 medicinal and 1 newly recorded species existed. The distribution and use in folk medicine were investigated. And the morphological description of several species was appended.

CONCLUSIONThe results provided a basis for the exploitation and utilization of the medicinal plant resources of Selagingellaceae.

China ; Conservation of Natural Resources ; Drugs, Chinese Herbal ; isolation & purification ; therapeutic use ; Humans ; Medicine, Chinese Traditional ; Phytotherapy ; Plants, Medicinal ; anatomy & histology ; chemistry ; classification ; Selaginellaceae ; anatomy & histology ; chemistry ; classification

AIMTo study the chemical constituents of Selaginella tamariscina (Beauv.) Spring.

METHODSThe compounds were isolated and purified by macroporous adsorption resin, Sephadex LH-20 and silica gel column chromatography and identified on the basis of their physicochemical and spectral data.

RESULTSFour compounds were obtained from the n-BuOH fraction of 70% acetone extracts. Their structures were elucidated as (7S, 8R)-7, 8-dihydro-7-(4-hydroxy-3,5-dimethoxyphenyl)-8-hydroxymethyl-[1'-( 7'-hydroxyethyl)-5' methoxyl] benzofuran-4-O-beta-D-glucopyranoside (tamariscinoside C, I), D-mannitol (II), tyrosine (II), shikimic acid (IV).

CONCLUSIONCompound I is a new compound, compounds II and III were obtained from the genius for the first time, compound IV was yielded from the plant for the first time.

Benzofurans ; chemistry ; isolation & purification ; Mannitol ; chemistry ; isolation & purification ; Molecular Conformation ; Molecular Structure ; Monosaccharides ; chemistry ; isolation & purification ; Plants, Medicinal ; chemistry ; Selaginellaceae ; chemistry ; Shikimic Acid ; chemistry ; isolation & purification ; Tyrosine ; chemistry ; isolation & purification

AIMTo study the chemical constituents of the water-extracts of Selaginella tamariscina (Beauv.) Spring.

METHODSVarious chromatographic techniques were used to separate and purify the constituents. Their physico-chemical properties and spectral data were used to elucidate the structures.

RESULTSNine compounds were isolated and identified as (2R,3S)-dihydro-2- (3',5'-dimethoxy-4'-hydroxyphenyl)-7-methoxy-5-acetyl-benzofuran (1), 3-hydroxy-phenpropionic acid-(2'-methoxy-4'-carboxy-phenol) ester (tamariscina ester A, 2), sygringaresinol (3), 1-(4'-hydroxyl-3'-methoxyphenyl)glycerol (4), ferulic acid (5), caffeic acid (6), vanillic acid (7), syringic acid (8), and umbelliferone (9).

CONCLUSIONCompound 1 and 2 are new compounds, and the others were isolated from Selaginella for the first time.

Benzofurans ; chemistry ; isolation & purification ; Caffeic Acids ; chemistry ; isolation & purification ; Coumaric Acids ; chemistry ; isolation & purification ; Molecular Conformation ; Molecular Structure ; Phenylpropionates ; chemistry ; isolation & purification ; Plants, Medicinal ; chemistry ; Selaginellaceae ; chemistry ; Vanillic Acid ; chemistry ; isolation & purification