Separation and determination of flavone and xanthone glycosides in Tibetan folk medicinal species Swertia mussotii and S. franchetiana by capillary electrophoresis

The contents of five pharmacologically active flavone and xanthone glycosides, namely, swertianolin, swertisin, isoorientin, mangiferin, and 7-O-[α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyl]-1,8-dihydroxy-3-methoxyxanthone, extracted from Tibetan folk medicinal species Swertia mussotii and S. franchetiana were determined by capillary electrophoresis with diode-array detection. The separation of five components has been optimized with a capillary column with a total length of 48.5 cm and effective length of 40 cm (50 μm i.d). The influence of the running buffer, the sodium dodecyl sulfonate (SDS) concentration, organic modifier, etc. on the resolution was evaluated. The background electrolyte contained 30 mM borate buffer, 28 mM SDS, 1.0% (v/v) acetonitrile, and was adjusted to pH 9.0 with 0.1 M NaOH. A good baseline resolution was obtained for the separation of five components within 5 min with the working voltage of 24 kV and a column temperature of 25°C. The established method was rapid and reproducible for the separation and determination of five flavone and xanthone glycosides from the extracts of S. mussotii and franchetiana plant samples. The text was submitted by the authors in English.     

Two new iridoid glycosides from the root barks of Sambucus williamsii Hance

Two new iridoid glycosides, named williamsoside C (1) and williamsoside D (2) were isolated from the root barks of Sambucus williamsii Hance. Their structures were established on the basis of extensive spectroscopic analysis (1D, 2D NMR and HRESIMS) and chemical studies as α-D-glucopyranosyl (1→2)-β-D-fructofuranosyl (4→6)-β-morroniside (1) and 7β-O-ethyl morroniside-(6'-O-7')-β-morroniside (2), respectively.     

Two new iridoid glycosides from the root barks of Sambucus williamsii Hance

Chemical investigation of the ethanol extract of the root barks of Sambucus williamsii Hance collected in the Heilongjiang province of China resulted in the isolation of two new iridoid glycosides, williamsoside A (1) and williamsoside B (2). Their structures were elucidated on the basis of extensive spectroscopic analysis (1D, 2D-NMR and HRESIMS) and chemical studies. Iridoid glycosides have for a long time been considered as characteristic ingredients of S. williamsii. However, the presence of iridoid glycosides with apiofuranosyl moieties in S. williamsii is reported for the first time in this study.     

Two new xanthone glycosides from Swertia punicea Hemsl. and their anti-inflammatory activity

Abstract

Two new xanthone glycosides (1–2), together with seven known analogues (3–9), were isolated from whole herb of Swertia punicea. The structures of these metabolites were established on the basis of detailed spectroscopic analysis and comparison with data reported in the literature. In an in vitro test, all isolates were evaluated for their anti-inflammatory activity. The results revealed that all of them showed significant anti-inflammatory activity with IC₅₀ values ranging from 1.237 to 3.319?mM. Compounds 3, 4, and 5 (IC₅₀ values in the range 1.237–1.987?mM) displayed more potent anti-inflammatory activity than the positive control, indomethacin (IC₅₀ value of 2.004?mM).     

Allobetonicoside and 6-O-Acetylmioporoside: Two new iridoid glycosides from Betonica officinalis L.

A new allose-containing iridoid diglycoside, allobetonicoside ( 1 ), and a new acyl iridoid glucoside, 6-O-acetylmioporoside ( 2 ) have been isolated from the aerial parts of Betonica officinalis L. in addition to two known iridoid glucosides, acetylharpagide ( 3 ) and reptoside ( 4 ). Their structures have been determined by spectroscopic methods as well as by means of chemical evidence.     

藏药达乌里秦艽中环烯醚萜苷的HPLC测定

采用HPLc法同时测定了藏药达乌里秦艽中龙胆苦苷(gentiopicroside)、獐牙菜苦苷(swertiamarin)、獐牙菜苷(sweroside)和落干酸(loganic acid)4种主要环烯醚萜苷类成分,利用在线质谱(MS)进行了定性分析,并与同属藏药麻花艽进行了比较.色谱柱为Eclipse XDB-C8(4.6 mm×150 mm i.d.,5 μm),流动相A:体积分数5%乙腈(含10 mmol甲酸)水溶液,流动相B:体积分数95%乙腈水溶液,以流动相A在0～15 min内由100%线性减至90%,15～20 min内保持90%不变线性梯度洗脱.流速1.0 mL/min,检测波长240 nm,柱温30℃.结果表明,4种成分均达到了基线分离,具有较好的线性关系和回收率.本法可作为达乌里秦艽药材有效成分的测定方法,为其有效成分的进一步开发利用提供依据.     

Structures of new aromatics glycosides from a Japanese folk medicine, the roots of Angelica furcijuga

Three new aromatics glycosides, hyuganosides II, IIIa, and IIIb, were isolated from a Japanese folk medicine, the roots of Angelica furcijuga KITAGAWA. The structures of the new glycosides were determined on the basis of chemical and physicochemical evidence.     

Two new xanthone diglycosides from Swertia longifolia Boiss

From aerial parts of Swertia longifolia Boiss., which grows in the north of Iran, five xanthones, two of which in diglycosidic form, were isolated. The structures were confirmed by means of their spectral data as isobellidifolin, bellidin, gentisein, 1,5-dihydroxy-3-methoxy-6-O-primeverosyl xanthone, and 8-hydroxy-3,5-dimethoxy-1-O-primeverosyl xanthone, the latter two of which were new derivatives in the plant kingdom.     

Phenylethanoid and iridoid glycosides from Veronica persica

A new phenylethanoid glycoside, persicoside (1) and three known phenylethanoid glycosides, acteoside (2), isoacteoside (3) and lavandulifolioside (4) were isolated from the aerial parts of Veronica persica. On the basis of spectral analyses, the structure of the new compound was elucidated to be 3,4-dihydroxy-beta-phenylethoxy-O-[beta-D-glucopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->3)]-4-O-caffeoyl-beta-D-glucopyranoside. Persicoside (1) and acteoside (2) exhibited radical scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. Beside phenylethanoid glycosides, a hexitol, dulcitol (5) and seven known iridoid glucosides, aucubin (6), veronicoside (7), amphicoside (8), 6-O-veratroyl-catalpol (9), catalposide (10), verproside (11) and verminoside (12) were isolated.     

Two new glycosides from the genus of Cassia

Two new glycosides were isolated and characterized by spectral analysis from the seeds of Cassia obtusifolia and the leaves of Cassia angustifolia.The structure was elucidated as 1-hydroxyl-2-acetyl-3,8-dimethoxynaphthalene-6-O-β-D-apiofuranosyl- (1→2)-β-D-glucopyranoside and 2-acetyl-3-methyl-8-methoxyl-1,4-naphthoquinone-6-O-β-D-glucopyranoside.     

Two new phenolic glycosides from Viscum articulatum

Two new phenolic glycosides, 1-O-benzyl-[5-O-benzoyl-beta-D-apiofuranosyl (1-->2)]-beta-D-glucopyranoside (1), and 4;-hydroxy-7,3;-dimethoxyflavan-5-O- beta-D-gluco-pyranoside (2), together with nine known flavanones 3 - 11, have been isolated from the dried whole plants of Viscum articulatum.Their structures were identified by extensive spectral analysis, especially 2D NMR techniques. Compound 9 showed weak anti-HIV-1 activity.     

Two new phenethanol glycosides from Ligustrum robustum

Two new phenethanol glycosides,named ligurobustoside P（1）,ligurobustoside Q（2） have been isolated from the leaves of Ligustrum robustum,together with the known compound angoroside A（3） which was firstly isolated from this species.The structures of the two new phenethanol glycosides（1-2） were elucidated by a combination of high-resolution electron ionization mass spectrometry（HR-ESI-MS）,¹H NMR,¹³C NMR,HMQC,and HMBC spectra for the first time.     

Two new tetranor-cycloartane glycosides from cimicifuga rhizome

Two new tetranor-cycloartane glycosides (1, 2) were isolated from Cimicifuga Rhizome. Their structures were determined by spectroscopic analysis. These compounds suggested the existence of a biogenetic pathway into C-23 lactone-type cycloartane glycosides.     

Two new phenylpropanoid glycosides from Sanguisorba officinalis

Two new phenylpropanoid glycosides,9-O-[6-O-acetyl-β-D-glucopyranosyl]-4-hydroxycinnamic acid(1) and 8-O-β-D-glucopyranosyl -(R)-(+)-3,4,8-trihydroxy methyl phenylpropionate(2) were isolated from the 80%EtOH extract of the roots of Sanguisorba officinalis.Their structures were characterized by spectroscopic analysis and chemical method,including 1D NMR,2D NMR,and HR-ESI-MS.Compounds 1 and 2 exhibited the moderate antimicrobial activities against all Gram-positive and Gram-negative bacteria tested.     

Two new monoterpene glycosides from Doellingeria scaber

Two new methane-type monoterpene glycosides were isolated from the roots of Doellingeria scaber.Their structures wereidentified as trans-p-menthane-1α,2β,8-triol 8-O-β-D-(3',6'-diangeloyloxy)-glucopyranoside and trans-p-menthane-1α,2β,8-triol 8-O-β-D-(3'-angeloyloxy,6'-isobutyloxy)-glucopyranoside based on 1D and 2D NMR spectroscopy.     

Two new steroidal glycosides from Ophiopogon japonicus

Two new C27-steroidal glycosides were isolated from the fibrous roots of Ophiopogon japonicus. The spectral analysis and chemical evidence revealed their chemical structures to be （25R）-spirost-5,14-dien-3β-yl-O-α-L-rhamnopyranosyl-（1 → 2）-β-D- xylopyranosyl-（1 → 4）-β-D-glucopyranoside （1） and ophiogenin 3-O-β-D-glucopyranoside （2）.     

Two new flavanonol glycosides from Gordonia chrysandra

Two new flavanonol glycosides named chrysandrosides A and B were isolated from the roots of Gordonia chrysandra Cowan. Their structures were determined by 1D and 2D NMR, FAB-MS techniques and chemical methods. Chrysandrosides A and B showed pronounced hepatoprotective activities against o-galactosamine （o-GalN）-induced toxicity in rat hepatic epithelial stemlike cells （WB-F344）. 2007 Dong Ming Zhang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.     

Aliphatic alcohol and iridoid glycosides from Asystasia intrusa

An aliphatic alcohol glycoside (asystoside) and an iridoid diglucoside (3'-O-beta-D-glucopyranosyl-catalpol) were isolated from the aerial part of Asystasia intrusa along with benzyl beta-D-glucopyranoside, zizybeoside I, (6S,9R)-roseoside, verbascoside, ehrenoside, 6beta-hydroxyantirrhide, angeloside, catalpol, ajugol, 6-deoxycatalpol, and scutellarioside II. The structural elucidations were based on analyses of physical and spectroscopic data.     

Separation of six xanthones from Swertia franchetiana by high‐speed countercurrent chromatography

In our present study, two groups of xanthones isomers (1‐hydroxy‐3,5,8‐trimethoxyxanthone and 1‐hydroxy‐3,7,8‐trimethoxyxanthone; 1,8‐dihydroxy‐3,7‐dimethoxyxanthone and 1,8‐dihydroxy‐3,5‐dimethanolxanthone) and other two xanthones (3‐methoxy‐1,5,8‐trihydroxyxanthone and 3,5‐dimethoxy‐1‐hydroxyxanthone) were separated from Swertia franchetiana . First, a solvent system composed of petroleum ether/methanol/water (2:1:0.6, v/v) was developed for the liquid–liquid extraction of these xanthones from the crude extract. Then, an efficient method was established for the one‐step separation of these six xanthones by high‐speed countercurrent chromatography using n‐hexane/ethyl acetate/methanol/ethanol/water (HEMEW; 6:4:4:2:4, v/v) as the solvent system. The results showed that liquid–liquid extraction could be well developed for efficient enrichment of target compounds. Additionally, high‐speed countercurrent chromatography could be a powerful technology for separation xanthones isomers. It was found ethanol could be a good methanol substitute when the HEMEW system could not provide good separation factors.     

Two new glycosides from the seeds of Cassia obtusifolia

Two new glycosides,nor-rubrofusarin-6-O-β-D-(6′-O-acetyl)glucopyranoside(1) and 1-desmethylaurantio-obtusin-2-O-β-D-glucopyranoside (2) were isolated from the seeds of Cassia obtusifolia and their structures were established by chemical and spectral evidences.