Two novel sesquiterpene lactones,cytotoxic vernolide-A and -B,from Vernonia cinerea

Bioassay-directed fractionation of an ethanolic extract of stems of Vernonia cinerea has resulted in the isolation of two novel sesquiterpene lactones, vernolide-A and -B. Their structures were elucidated on the basis of spectroscopic analysis. Biological evaluation showed that vernolide-A demonstrated potent cytotoxicity against human KB, DLD-1, NCI-661, and Hela tumor cell lines (ED(50)=0.02, 0.05, 0.53, 0.04 microg/ml for KB, DLD-1, NCI-661, and Hela, respectively); vernolide-B had marginal cytoxicity (ED(50)=3.78, 5.88, 6.42 microg/ml for KB, NCI-661, and Hela, respectively).     

Steroidal glycosides and aromatic compounds from Smilax riparia

Two new steroidal glycosides named riparosides A (1) and B (2), and two aromatic compounds (3, 4), together with four known flavonoid derivatives have been isolated from the EtOH extract of the rhizomes and roots of Smilax riparia A. DC. The structure of riparoside A (1) was determined to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranosyl 3beta,20alpha-dihydroxy-5alpha-furost-22(23)-ene 26-O-beta-D-glucopyranoside. Riparoside B (2) was characterized as 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranosyl 3beta,16beta-dihydroxy-5alpha-pregnan-20-one 16-O-[5-O-beta-D-glucopyranosyl 5-hydroxy-4-methyl-pentanoic acid]-ester 26-O-beta-D-glucopyranoside. Compounds 3 and 4 were elucidated as a sucrosyl ferulic acid ester and 7-O-methyl-10-oxythymol gentiobioside, respectively.     

Molecularly imprinted layer-coated monodisperse spherical silica microparticles toward affinity-enrichment of isoflavonoid glycosides from Radix puerariae

This paper reports the preparation of puerarin (PR) imprinted layer-coated silica microparticles toward selective recognition of PR and fast affinity-enrichment of the main isoflavonoid glycosides from the crude extract of Radix puerariae. Before the preparation, quantum mechanics (QM) method was applied to identify three kinds of common functional monomers capable of interaction with PR and then predicted optimal functional monomer (acrylamide, AA) and the relative molar ratio of template to functional monomer (PR/AA, 1:4). The obtained PR-imprinted silica microparticles were evaluated by transmission electron microscope (TEM) and rebinding experiments, exhibiting good morphology and high binding affinity to PR. Meanwhile, the rebinding amount of the imprinted microparticles to PR was nearly 2.1-folds that of non-imprinted microparticles. When the PR-imprinted microspheres were used as packing materials for solid-phase extraction, the recovery yields of PR, daidzin (DD) and genistin (GS) were simultaneously up to 90% by one-step extraction from the crude extract of Radix puerariae. Additionally, the PR-imprinted microparticles could be re-used for at least 5 times without losing any extraction efficiency. These results indicate that the PR-imprinted microparticles have highly selective adsorption capabilities to PR, DD and GS from the crude extract of Radix puerariae. The method of molecularly imprinted polymers (MIPs) coupled with solid-phase extraction (SPE) provides a good solution of the enrichment and separation of active extracts from complicated traditional Chinese medicine (TCM) with certain structures.     

Two phenylpropanoid glycosides from Neopicrorhiza scrophulariiflora

Two new phenylpropanoid glycosides, scrophulosides A (1) and B (2), were isolated from the rhizomes of Neopicrorhiza scrophulariiflora (Scrophulariaceae), along with two known compounds, androsin (3) and picroside I. Their structures were elucidated on the basis of both chemical and spectroscopic data.     

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 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 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.     

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 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 pentasaccharide resin glycosides from Argyreia acuta

Two new compounds of acutacosides 1 and 2, pentasaccharide resin glycosides were isolated from the aerial parts of Argyreia acuta. The core of the two compounds was operculinic acid A, and they were esterfied at the same position, just one substituent group was linked at C-2 of Rha. The absolute configuration of the aglycone in the two compounds was established by Mosher's method, which was (11S)-hydroxyhexadecanoic acid (jalapinolic acid). Their structures were established by a combination of spectroscopic and chemical methods.     

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 phthalide dimers from the radix of Angelica sinensis

The phytochemical investigation of extracts from the radix of Angelica sinensis yielded a new phthalide dimer, 3,3'Z-6.7',7.6'-diligustilide, along with a known dimer, levistolide A. Their structures were established on the basis of spectral data, particularly using 1D-NMR and several 2D shift-correlated NMR pulse sequences (1H-1H COSY, HSQC, HMBC and NOESY).     

Two labdane diterpene and megastigmane glycosides from Aquilegia hybrida

Two new labdane diterpene glycosides, named aquosides A and B, and a new megastigmane glycoside, named aquoside C, have been isolated from the air-dried aerial parts of Aquilegia hybrida together with three known compounds comprising a phenolic glycoside and two flavone C-glycosides. Their structures were determined on the basis of spectroscopic data and chemical evidence.     

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 bis-coumarin glycosides from Daphne giraldii NITSCHE

Two new bis-coumarin glycosides were isolated from the stem barks of Daphne giraldii NITSCHE. Their structures were elucidated as 6-O-alpha-L-rhamnnopyranosyl daphnogirin (1), and 6-O-beta-D-apiofuranosyl daphnogirin (2), on the basis of detailed spectroscopic analysis. Compounds 1 and 2 were tested inhibitory effects against production of nitric oxide (NO) in RAW264.7 cells, and cytotoxicity of human tumor cell lines A549, LOVO, QGY-7703, 6T-CEM. The results showed that compounds 1 and 2 neither reduced production of NO, nor inhibited human tumor cell lines.     

Five new steroidal glycosides,pregnedioside-A, -B,and their three monoacetates,from an Okinawan soft coral of Alcyonium sp.

Five new pregnene-type steroidal glycosides, named pregnedioside -a ($\text{1}$), 4′-O-acetyl-pregnedioside-a ($\text{2}$), 3′-O-acetyl-pregnedioside-a ($\text{3}$), pregnedioside-b ($\text{5}$), and 4′-O-acetyl-pregnedioside-b ($\text{6}$), were isolated from an Okinawan soft coral of Alcyonium sp. and their structures were elucidated. These are rare examples of steroidal gylcosides from soft coral.     

Two new abietane diterpenoid glycosides from Clinopodium chinense

Two new abietane diterpenoid glycosides, named clinopoditerpenes B (1) and C (2), were isolated from Clinopodium chinese. The structures of the new compounds were determined on the basis of extensive spectral analysis. Compound 1 exhibited cardioprotective effect against H₂O₂-induced apoptosis in H9c2 cells.     

Two new acylated flavonol glycosides from Vicia amurensis

Two new acylated flavonol glycosides, named amurenosides A and B, together with quercetin 3-(2,6-di-O-alpha-rhamnopyranosyl-beta-galactopyranoside), have been isolated from the whole plant of Vicia amurensis. Their structures were elucidated as quercetin 3-O-alpha-L-(3-feruloylrhamnopyranosyl)(1-->6)-[alpha-L-rhamnopyra nosyl(1-->2)]-beta-D-galactopyranoside and quercetin 3-O-alpha-L-(2-feruloylrhamnopyranosyl)(1-->6)-[alpha-L-rhamnopyra nosyl(1-->2)]-beta-D-galactopyranoside on the basis of various NMR techniques, FAB mass spectrometry and chemical reactions.     

Two new indolopyridoquinazoline alkaloidal glycosides from Ranunculus ternatus

Two new indolopyridoquinazoline alkaloidal glycosides, 11-O-beta-D-glucopyranosyl rutaecarpine (ternatoside C) and 11-O-alpha-L-rhamnosyl-(1-->6)-beta-D-glucopyranosyl rutaecarpine (ternatoside D) were isolated from the roots of Ranunculus ternatus. Their structures were determined on the basis of spectroscopic and chemical methods.