OBJECTIVETo study the chemical constituents from the roots of Rehmannia glutinosa.

METHODThe compounds were isolated by various chromatographic methods and identified by spectroscopic analysis.

RESULTTwelve compounds were isolated and their structures were identified as 5-hydroxymethyl-pyrrole-2-carbaldehyde (1), 5-hydroxymethyl furfural (2), tyrosol (3), 5,6-dihydroxy-beta-ionone (4), 6-O-E-feruloyl ajugol (5), acteoside (6), leucosceptoside A (7), martynoside (8), isomartynoside (9), purpureaside C (10), jionoside A1 (11), and jionoside B1 (12).

CONCLUSIONCompounds 1, 3 and 9 were isolated from the genus Rehmannia for the first time.

Glycosides ; analysis ; Rehmannia ; chemistry

OBJECTIVETo study the chemical constituents from n-BuOH fraction of the stems of Periploca forrestii.

METHODThe compounds were separated and purified by various chromatographic techniques and recrystallisation. The physico-chemical properties and spectral data were applied to identify structure of these compounds.

RESULTSix glycosides were isolated and identified as emodin-8-O-beta-D-glucopyranoside (1), physcion-8-O-beta-D-glucopyranoside (2), kaempferol-3-O-beta-D-galactopyranoside (3), kaempferol-3-O-alpha-L-arabinopyranoside (4), quercetin-3-O-beta-D-glucopyranoside (5), quercetin-3-O-alpha-L-arabinopyranoside (6).

CONCLUSIONThese six compounds were obtained for the first time from this plant.

Glycosides ; chemistry ; isolation & purification ; Periploca ; chemistry

OBJECTIVETo isolate and identify the active xanthone glycosides in Halenia elliptica.

METHODThe compounds were isolated by column chromatography, semi-preparative high performance liquid chromatography and related techniques. Their structures were elucidated through spectroscopic analysis (NMR and MS).

RESULTSix xanthone glycosides were isolated and identified as: 2,3,5-trimethoxy-1-O-primeverosyloxyxanthone (1), 2, 3, 4, 5-tetramethoxy-1-O-primeverosyloxyxanthone (2), 2, 3, 5, 7-tetramethoxy-1-O-primeverosyloxyxanthone (3), 2, 3, 7-trimethoxy-1-O-primeverosyloxyxanthone (4), 2, 3, 4, 7-tetramethoxy-1-O-primeverosyloxyxanthone (5), and 2, 3, 4, 5, 7-pentamethoxy-1-O-primeverosyloxyxanthone (6).

CONCLUSIONCompounds 4-6 were isolated from this plant for the first time.

Drugs, Chinese Herbal ; chemistry ; Gentianaceae ; chemistry ; Glycosides ; chemistry ; Xanthones ; chemistry

This study aims to identify the chemical constituents from Callicarpa kwangtungensis and determine their activities. MCI, ODS, and Sephadex LH-20 chromatography and semi-preparative HPLC were employed to separate the chemical constituents. A total of 15 compounds were separated, and their structures were identified on the basis of spectroscopic analysis and comparison with the data in relevant literature. Specifically, the 15 compounds were 3-O-α-L-rhamnopyranosyl-6-O-β-D-apiofuranosyl-4-O-E-caffeoyl-D-glucopyranoside(1), 3,6-O-α-L-dirhamnopyranosyl-4-O-E-caffeoyl-D-glucopyranoside(2), β-OH-forsythoside B(3), β-OH-poliumoside(4),(+)-lyoniresinol-3α-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside(5),(+)-lyoniresinol-3α-O-β-D-glucopyranoside(6),(-)-lyoniresinol-3α-O-β-D-glucopyranoside(7), kelampayoside A(8), descaffeoylpoliumoside(9), acteoside(10), alyssonoside(11), poliumoside(12), isacteoside(13), acetyl forsythoside B(14), and forsythoside B(15). Compounds 1 and 2 were novel, and the NMR data of compounds 3 and 4 were reported here for the first time. Furthermore, the hemostatic activities of the extract and abundant ingredients(compounds 12 and 15) of C. kwangtungensis were determined with Yunnan Baiyao as the positive control and normal saline as the negative control. The extract and compounds 12 and 15 significantly shortened the tail tip bleeding time in mice.
Animals ; Mice ; Callicarpa ; Hemostatics ; China ; Glycosides/chemistry*

Most bacterial cell surface glycans are structurally unique, and have been considered as ideal target molecules for the developments of detection and diagnosis techniques, as well as vaccines. Chemical synthesis has been a promising approach to prepare well-defined oligosaccharides, facilitating the structure-activity relationship exploration and biomedical applications of bacterial glycans. L-Galactosaminuronic acid is a rare sugar that has been only found in cell surface glycans of gram-negative bacteria. Here, an orthogonally protected L-galactosaminuronic acid building block was designed and chemically synthesized. A synthetic strategy based on glycal addition and TEMPO/BAIB-mediated C6 oxidation served well for the transformation of commercial L-galactose to the corresponding L-galactosaminuronic acid. Notably, the C6 oxidation of the allyl glycoside was more efficient than that of the selenoglycoside. In addition, a balance between the formation of allyl glycoside and the recovery of selenoglycoside was essential to improve efficiency of the NIS/TfOH-catalyzed allylation. This synthetically useful L-galactosaminuronic acid building block will provide a basis for the syntheses of complex bacterial glycans.
Carbohydrates ; Glycosides ; Oligosaccharides ; Oxidation-Reduction ; Polysaccharides/chemistry*

The poor solubility of insoluble components of traditional Chinese medicine(TCM) is an important factor restricting the development of its preparations. Natural polysaccharides of TCM can be used as functional components to increase the solubility of insoluble components. Epimedium flavonoid secondary glycoside components(EFSGC) have been shown to have positive effects on the prevention and treatment of osteoporosis, but they exhibit poor solubility. Therefore, the strategy of solubilizing EFSGC with TCM polysaccharides was adopted, and its effect on the permeability and stability of EFSGC was evaluated in this study. Based on the equilibrium solubility experiment of EFSGC, it was found that Panax notoginseng crude polysaccharide(PNCP) had the best solubilization effect on EFSGC among the ten kinds of TCM polysaccharides, which increased the solubility of EFSGC from 0.8 mg·mL~(-1) to 13.3 mg·mL~(-1). It should be noted that after the solubilization of EFSGC by preparation technology, the effects on permeability and stability should be considered. Therefore, this study also investigated these two properties. The results showed that PNCP increased the effective transmittance of EFSGC from 50.5% to 71.1%, which could increase the permeability of EFSGC significantly. At the same time, it could improve the stability of EFSGC in the simulated gastric juice environment. In order to explain the solubilization mechanism of PNCP on EGSGC, critical micelle concentration, particle size, potential, differential scanning calorimetry, and infrared spectroscopy were analyzed. It was preliminarily inferred that the mechanism was as follows: PNCP and EFSGC could self-assemble into aggregates for solubilization by intermolecular hydrogen bonding interaction in water. In summary, PNCP can not only improve the solubility of EFSGC but also improve its permeability and stability. This study lays the foundation for the application of TCM polysaccharides as a functional component to solubilize insoluble components.
Medicine, Chinese Traditional ; Flavonoids/chemistry* ; Glycosides ; Epimedium/chemistry* ; Solubility ; Cardiac Glycosides ; Polysaccharides/chemistry*

OBJECTIVETo investigate the extraction method of polyglycosides from Tripterygium wilfordii.

METHODThe extraction method of pressurized liquid extraction was employed and chromogenic colorimetric technique were used for quantitative analysis. Based on the single-factor experiment, according to the center combination design this paper used three factors and three levels of response surface methodology for process optimization.

RESULTThe optimized conditions were as follows: ratio of solid to liquid was 1:9.5, at the temperature of 115 degrees C for 80 minutes, the actual extract ratio and purity of polyglycosides obtained were 0.21% and 0.52%, respectively.

CONCLUSIONThe method of pressurized liquid extraction has obvious advantages over conventional reflux extracting.

Glycosides ; isolation & purification ; Plant Extracts ; chemistry ; Pressure ; Tripterygium ; chemistry

Medicinal plants have provided numerous medicinal active ingredients for thousands of years and these ingredients have been used in Chinese medicine (CM) and traditional pharmacologies worldwide. Recently, the exploitation and utilisation of medicinal plant resources has increased significantly. The results of the studies have led to the identification of many active components, such as steroidal alkaloids, saponins, terpenoids, and glycosides, in various medicinal plants with different evolutionary levels. Moreover, research on the chemical classification, molecular phylogeny, and pharmacological activity of medicinal plants is increasing in popularity. Pharmacophylogeny is an interdisciplinary topic that studies the correlation between plant phylogeny, chemical composition, and curative effects (pharmacological activity and the traditional curative effect) of medicinal plants. In addition, it provides the basic tools to enable research and development of CM resources. This literature review, based on the genetic relationship between phytogroup and species, highlights the formation process, research content, applications, and future directions of pharmacophylogeny.
Alkaloids ; Glycosides ; Plant Extracts/chemistry* ; Plants, Medicinal/chemistry* ; Saponins ; Terpenes

Chemical constituents of ethanol extract of Pulsatillae Radix were investigated. The n-butanol fraction of ethanol extract of Pulsatillae Radix was isolated and purified by macroporous resin and silica gel column chromatography and semi-preparative high performance liquid chromatography. The triterpenoid glycosides were identified by multiple spectral methods. Six compounds were obtained from the n-butanol fraction of ethanol extract of Pulsatillae Radix and identified as 23-aldehyde-cussosaponin C(1), cussosaponin C(2), anemoside B4(3), akebia saponin D(4), pulchinenoside E3(5), and hederacoside C(6). Among them, compound 1 was a new compound.
1-Butanol ; Drugs, Chinese Herbal ; Glycosides/chemistry* ; Ethanol/chemistry*

OBJECTIVETo investigate chemical constituents from an ethanolic extract of the branch of Fraxinus sieboldiana (Oleaceaue)

METHODThe constituents were isolated and purified by a combination of various chromatographic techniques including silica gel, macroporous adsorbent resin, Sephadex LH-20, and preparative HPLC. Structures of the isolates were elucidated by spectroscopic methods including 1D and 2D NMR and MS techniques.

RESULTFour phenolic and twelve phenylethanoidal glycosides were obtained and their structures were identified as 2,6-dimethoxy-p-hydroquinone-4-O-beta-D-glucopyranoside (1), 2,6-dimethoxy-p-hydroquinone-1-O-beta-D-glucopyranoside (2), 4-hydroxy-3-methoxyphenyl beta-D-glucopyranoside (3), 4-hydroxy-3-methoxyphenyl beta-D-xylopyranosyl (1-->6)-O-beta-D-glucopyranoside (4), osmanthuside H (5), 2-(4-hydroxyphenyl) ethyl beta-D-glucopyranoside (6), 2-(3, 4-dihydroxyphenyl) ethyl beta-D-glucopyranoside (7), 2-hydroxy-4-(2-hydroxyethyl)-phenyl beta-D-glucopyranoside (8), 4-(2-hydroxyethyl)-2-methoxyphenyl beta-D-glucopyranoside (9), calceolarioside B (10), calceolarioside A (11), ferruginoside A (12), isolugrandoside (13), acteoside (14), chiritotoside C (15), and plantasisoside (16).

CONCLUSIONCompounds 1-4,9,12, 13 and 16 were obtained from the genus Fraxinus for the first time.

Ethanol ; chemistry ; Fraxinus ; chemistry ; Glycosides ; analysis ; chemistry ; isolation & purification ; Phenol ; chemistry ; Plant Stems ; chemistry