Two new acetylated ginsenosides from the roots of Panax quinquefolium

Two new acetylated ginsenosides, 20（S）-protopanaxatriol-6-O-α-L-rhamnopyranosyl （1 → 2）-β-D-6＇-O-acetylglucopyranoside （1） and 20（R）-protopanaxatrol-6-O-α-L-rhamnopyranosyl （1 → 2）-β-o-6＇-O-acetylglucopyranoside （2）, were isolated from the roots of Panax quinquefolium. The structures were elucidated on the basis of spectroscopic techniques and chemical means.     

A new C27-steroidal glycoside from Ophiopogon japonicus

A new C27-steroidal glycoside with three known compounds were isolated from the tuber of Ophiopogonjaponicus （Thunb.） Ker-Gawl. Based on the spectral analysis, including HRMS, 1H NMR, 13C NMR, DEPT, 1H-1H COSY, HMQC and HMBC, their chemical structures were determined as pennogenin-3-O-α-L-rhamnopyranosyl-（1→ 2）-β-D-xylopyranosyl-（1→ 4）-13-D-gluco- pyranoside （1）, pennogenin-3-O-α-L-rhamnopyranosyl-（1→ 2）-β-D-glucopyranoside （2）, ophiopojaponin C （3） and ophiopogonin D （4）. 2007 Jian Zhong Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.     

Synthesis ofα-D-GlcpNAc-（1→2）-[α-D-ManpNAc-（1→3）-]α-L-Rhap-（1→2）-α-L-Rhap-（1→3）-α-L-Rhap,the repeating unit of O10 antigen from Acinetobacter baumannii

An efficient synthesis ofα-D-GlcpNAc-（1→2）-[α-D-ManpNAc-（1→3）-]α-L-Rhap-（1→2）-α-L-Rhap-（1→3）-α-L-Rhap（1）, the repeating unit of the O10 antigen from Acinetobacter baumannii was achieved via sequential assembly of the building blocks,p- methoxylphenyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside（2）;2-O-allyloxycarbonyl-3,4-di-O-bcnzoyl-α-L-rhamnopyranosyl tri- chloroacetimidate（3）;4-methoxylphenyl 3-O-allyloxycarbonyl-4-O-benzoyl-α-L-rhanmopyranoside（4）;2-azido-3-O-benzoyl-2- deoxy-4,6-O-isopropylidene-α-D-mannopyranosyl trichloroacetirnidatc（5）;2-azido-3,4,6-tri-O-benzoyl-2-deoxy-α,β-D-glucopyr- ano syl trichloroacetimidatc（6）.The total yield of 1 from 4 was 4.7%.     

Cytotoxic triterpenoid saponins from Ardisia pusilla

A new triterpenoid saponin,3-O-{β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-ghcopyranosyl-(1→2)]-α-L-arabinopyranosyl }-3β,16α,28α-trihydroxy-1313,28-epoxy-oleanan-30-al(ardipusilloside Ⅲ,1),together with two known sapo-nins,ardisiacrispins A(2)and B(3),were isolated from the whole plants ofArdisia pusilla A.DC.Their structures were elucidated by extensive spectral analysis and chemical evidences.Saponins 1 and 3 exhibited significant cytotoxicity against human glioblastoma U251MG cells.     

Synthesis of di-and tetrasaccharide containing 6-deoxytalose from the O-antigenic polysaccharide of B. pseudomallei strain 304b

Synthesis of the disaccharide β-D-Glup-(1→3)-6-deoxy-α-L-Talp Ⅱ,and its dimer Ⅲ from the O-antigenic polysaccharide of Burkholderia pseudomallei strain 304b,were achieved through assembly of suitably synthesized building blocks,4-methoxylphenyl 6-deoxy-2,4-di-O-benzoyl-α-L-talopyranoside (7),3-O-allyl-2,4,6-tri-O-benzoyl-α,β-D-glucopyranosyl trichloroacetimidate (8) and 2,3,4,6-tetra-O-benzoyi-α,β-D-glucopyranosyl trichloroacetimidate (Ⅱ).The total yield of Ⅲ from 4-methoxyiphenyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (1) was 18%.     

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 triterpene glycosides from the sea cucumber Bohadschia marmorata Jaeger

Further studies on the sea cucumber Bohadschia marmorata Jaeger led to the isolation of a new holostan-type triterpene glycoside,Marmoroside C（1）together with a known triterpene glycoside（2）.On the basis of spectroscopic analyses,including two- dimensional NMR techniques,and chemical reactions,the structure of the new triterpene glycoside was elucidated as 3-O-[3-O- methyl-β-D-glucopyranosyl-（1→3）-β-D-glucopyranosyl-（1→4）-β-D-quinovopyranosyl-（1→2）-4-O-sodium-sulfato-β-D-xylo- pyranosyl]-25-acetoxy-22-oxo-9（11）-holostene-3β,12α,17α-triol.     

A new cycloartane nortriterpenoid from Quercus variabilis Blume

The leaves and stems of Quercus variabilis Blume afforded a new cycloartane nortriterpenoid,3α-acetyloxy-4α,14α-dimethyl-9β, 19-cycloergost-24-oic acid(1),along with five known compounds(2-6).The structure of 1 was elucidated by 1D and 2D NMR and mass spectroscopy.     

A novel cytotoxic neophysalin from Physalis alkekengi var.francheti

A new neophysalin,named 5α-hydroxy-25,27-dihydro-4,7-didehydro-7-deoxyneophysalin A(1),along with three other known neophysalins(2-4) were isolated from the calyxes of Physalis alkekengi L.var.francheti(Mast.) Makino.The structure of 1 was determined by means of 1D and 2D NMR,UV,IR and mass spectra.Compound 1 displayed potent cytotoxicities in vitro against PC- 3 and LNCaP cell lines.     

Novel Enone-benzene Rearrangement of 4,4-Dialkylcholest-5-en-3-ones to Ring-B Aromatic Steroidal Hydrocarbons Catalysed by p-Toluenesulfonic acid

Under acidic conditions, α,α-dimethyl-β,γ-unsaturated cyclohexanones undergoes an enone-benzene rearrangement leading to aromatic derivatives^1-4. We recently run an enone-benzene rearrangement of 4,4-dimethyl-cholest-5-en-3-one (1a) catalysed by montmorillonite K-10 to give 1,3,4-trimethyl-19-norcholesta-1,3,5(10)-triene (2a) in moderate yield accompanying intractable mixture of hydrocarbons as by products⁵. Repetition of this reaction by employing TsOH as a catalyst, 2a was obtained in 65% yield and a new product, 6-methyl-3-isopropyl-A,19-dinorcholesta-6,8,10(5)-triene (3a), was also isolated in 25% yield. The formation of 3a has not been reported in earlier studies^1-5. Herein we report the novel enone-benzene rearrangement of 4,4-dialkylcholest-5-en-3-ones (1a~d) leading to ring-B aromatic steroidal hydrocarbons (3a~d) catalysed by TsOH (Scheme 1).     

Flavonoid triglycosides from the seeds of Camellia oleifera Abel

Two flavonoid triglycosides, kaempferol 3-O-{ β-D-glucopyranosyl-（1→2）-[α-L-rhamnopyranosyl-（1→ 6）]-β-D-glucopyranoside} （1） and kaempferol 3-O-{ β-D-xylopyranosyl-（1 → 2）-[α-L-rhamnopyranosyl-（1→6）]-β-D-glucopyranoside } （2）, were isolated from the seed of Camellia oleifera Abel. The absolute configuration of compound 1 was established on the basis of its X-ray analysis. Their cytotoxic activities and anti-HIV-RT activities were evaluated.     

云南重楼中的新甾体皂苷

从云南重楼Paris polyphylla Sm. var. yunnanensis(France. )Hand.-Mazz.的干燥根茎中分离鉴定了4个甾体皂苷(1~4), 其中化合物1是新化合物, 采用波谱技术鉴定其结构为24-O-β-D-吡喃半乳糖基-(23S,24S)-螺甾-5, 25(27)-二烯-1β,3β,23,24-四醇-1-O-β-D-吡喃木糖基(1→6)-β-D-吡喃葡萄糖基(1→3)[α-L-吡喃鼠李糖基(1→2)]-β-D-吡喃葡萄糖苷.     

A new glycoside from the leaves of Neoalsomitra integrifoliola

A new ionone glycoside （6R,9R）-blumenyl α-L-rhamnopyranosyl-（1 → 6）-β-D-gluco-pyranoside （1）, together with a new natural product 2-methoxyl-4-trans-pmpenyl-phenol α-L-rhamnopyranosyl-（1 → 6）-β-D-glucopyranoside （2）, was isolated from the leaves ofNeoalsomitra integrifoliola. Their structures were elucidated by chemical and spectral analysis. Compound 1 showed weak anti-inflammatory and low-level antioxidant activities.     

川麦冬中的新呋甾皂苷的分离与鉴定

从川麦冬块根总皂苷中分离并鉴定了4个双糖链甾体皂苷化合物, 其中化合物1为新化合物, 化合物2~4是已知化合物.     

Two new kaempferol glycosides from the seeds of Camellia semiserrata Chi

Two new acetylated kaempferol glycosides were isolated from the seeds of Camellia semiserrata Chi,their structures were elucidated as kaempferol-3-O-[(3-O-acetyl)-α-L-rhamnopyranosyl(1→3)(4-O-acetyl)-α-L-rhamnopyranosyl(1→6)-β-D-glucopyranoside] (1) and kaempferol-3-O-[(2-O-acetyl)-α-L-rhamnopyranosyl(1→3)(4-O-acetyl)-α-L-rhamnopyranosyl(1→6)-β-D-gluco -pyranoside](2) by spectral experiments(including ESI-MS,1D- and 2D-NMR).     

Two New Phenolic Glycosides from Magnolia rostrata

For a long time Magnolia rostrata has been used as a substitute of Magnolia officinalis which is a precious traditional Chinese medicine1. The aqueous constituents of M. rostrata have not been studied2. During our studies on the n-Bu-OH extract, two new phenolic glycosides (Figure 1) were isolated. Here, we report their structural elucidation. Compound 1, white amorphous powder, mp 180-182°C exhibited a molecular formula C21H30O11 based on its quasi-molecular ion peak at m/z 457 [M-H]- …     

Synthesis of di-μ-OXO-tetra-（α-pentyloxy） tin（Ⅳ） phthalocyanine

Axially substituted tin phthalocyanines, namely dichloride-tetra-（α-pentyloxy） tin （Ⅳ） phthalocyanine 2, dihydroxy-tetra-（α-pentyloxy） tin （Ⅳ） phthalocyanine 3 and its dimmer di-μ-oxo-tetra-（α-pentyloxy） tin（Ⅳ） phthalocyanine 4 were synthesized. The catalytic effect of H2O-free CaCl2 in quinoline was used for condensation of dihydroxy tin phthalocyanine 3 to the cofacially array dimmer 4. Their structures were characterized by UV-vis, IR, elemental analysis, MS, as well as ^1HNMR spectroscopy.     

CONDENSATION REACTION OF α-AROYL-α-ACETYL KETENE CYCLIC DITHIOACETALS WITH AROMATIC ALDEHYDES

As a versatile three-carbon syntho,α-oxoketene cyclic acetals 1 have been applied in many fields. In order to study the structure and application of 1, we performed that α-aroyl-α-acetyl ketene cyclic dithioacetals 2 or 3 condensed with aromatic aldehydes catalyzed by sodium ethoxide and fifteen new condensation products 4 and 5 were obtained.     

Synthesis and properties of optically active 1,3-diols and their derivatives as chiral dopants for ferroelectric liquid crystals

New chiral dopants β-hydroxy ketones 1, 1,3-diols 2, 1,3-dioxanes 3 and 1,3-dioxan-2-ones 4 were designed and synthesized. Reaction of (R)-1,2-epoxyoctane with carbanions derived from 2-(4-substituted phenyl)-1,3-dithianes followed by hydrolysis of the resulting hydroxy dithianes afforded 1. Reduction of 1 gave the diols 2, which yielded 3 upon acetalization and 4 upon carbonation. The syn isomers of 2, 3, and 4 exhibited larger spontaneous polarizations, when applied as chiral dopants, than the anti isomers or hydroxy ketones 1.     

Two New Borates Built by Different Types of {B9} Cluster Units

Two new belt-like borates Na₄[B₉O₁₄(OH)₃]·0.5H₂O(1) and Na₅[B₉O₁₄(OH)₄](2) have been synthesized under solvothermal conditions. Both compounds contain unprecedented B₉O₁₆(OH)_n^(n+5)-[n=3(1), 4(2)] clusters, which are constructed from four B₃O₃ rings via three BO₄ tetrahedra. Compound 1 exhibits a rare 1D belt with two types of 8-membered ring(MR) windows based on B₉O₁₆(OH)₃^8- clusters. Compound 2 features two different 1D belts built by different B₉O₁₆(OH)₄^9- units, which is first discovered in borate family. UV-Vis diffuse reflectance spectra reveal that compounds 1 and 2 have the cut-off edges below 190 nm, indicating that they may have potential application in deep UV(DUV) region.