First total synthesis of 10α-hydroxy-4-muurolen-3-one and its C_(10)-isomer

An efficient synthetic route to muurolane type sesquiterpenes starting from （R）-carvone, employing allylic diazene rearrangement and the ring closing methesis （RCM） reaction as key steps, is described. The first asymmetric total synthesis of （-）-10α- hydroxy-4-muurolen-3-one 11 and （-）-10β-hydroxy-4-muurolen-3-one C was accomplished. Through the total synthesis, the absolute configurations of the natural products A, B and C were established.

Synthesis of 1,7-Bis(4-hydroxyphenyl)-3-hydroxy-1,3-heptadien-5-one

A facile synthesis of the analog of curcumin. 1,7-bis (4-hydroxyphenyl)-3-hydroxy-1.3-heptadien-5-one 1 was achieved. The key step was completed through the regioselective condensation of ketone 5 and acyl chloride 7.

A Facile Synthesis of 6β-Hydroxy-7α(H)-eudesma-4-en-3-one

A stereoselective total synthesis of 6β-hydroxy-7α(H)-eudesma-4-en-3- 1startingfrom (+)-dihydrocarvone 7 has been described.

The First Total Synthesis of Natural 6β-Cinnamoyloxy-1α- hydroxy-5, 10-bis-epi-eudesm-4-en-3-one

The first total synthesis of natural 6β-cinnamoyloxy-1α-hydroxy-5, 10-bis-epi- eudesm-4-en-3-one （1）, a highly complex natural eudesmane, was described.

Syntheses, Characterization and Biological Activity of Coordination Compounds of 3-Hydroxy-2-methyl-4<i>H</i>-pyran-4-one and Its Mixed Ligand Complexes with 1,2-Diaminocyclohexane

Coordination compounds of 3-hydroxy-2-methyl-4H-pyran-4-one with iron(III), cobat(III) and chromium(III) were synthesized with M:L (1:2). Mixed ligand coordination compounds of 3-hydroxy-2-methyl-4H-pyran-4-one and 1,2-diaminocyclohexane using the same metal ions were also synthesized M:L1:L2 (1:1:1) where L1 is 3-hydroxy-2-methyl-4H-pyran-4-one and L2 is 1,2-diaminocyclohexane. The coordination compounds obtained were characterized using electronic and infrared spectral analyses, magnetic susceptibility and percentage metal analysis. They were also evaluated for their cytotoxic and antioxidant activities. The result obtained suggested that octahedral geometry was obtained for all the compounds, as a result of additional two molecules of the solvent coordinated to the metal ions. Both the primary and secondary ligands coordinated in a bidentate fashion. The synthesized compounds exhibited moderate cytotoxicity, although none was as active as the standard. The cobalt(III) mixed ligand complex elicited the highest activity. The synthesized compounds all exhibited good to moderate antioxidant activity.

A Facile Synthesis of 9,10-Dimethoxybenzo[6,7]- ox-epino[3,4-<i>b</i>]quinolin-13(6<i>H</i>)-one and Its Derivatives

A concise and efficient method for the synthesis of novel 9,10-imethoxybenzo[6,7]oxepino[3,4-b]quinolin13(6H)-one and its derivatives 7a-p has been developed via the intramolecular Friedel-Crafts acylation reactions of 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylic acids 6a-p with polyphosphoric acid (PPA) as catalyst and solvent under mild conditions. The key intermediates 6a-p were prepared through the in situ formation of ethyl 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylates 5a-p followed by hydrolysis with aqueous ethanolic sodium hydroxide solution. The novel synthetic method has the advantages of good yields, easy work-up, and environmentally friendly character, which may provide a novel highly efficient process for making quinoline and related azaheterocycle libraries.

Synthesis of Gingerenone C and 5-Hydroxy-1-(4′-hydroxy-3-methoxyphenyl)-7-(4′′-hydroxyphenyl)-3-heptanone

The two diarylheptanoids (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl) hept-4-en-3-one 1 (Gingerenone C) and (±)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4- hydroxyphenyl)-3-heptanone 2 were synthesized from vanillin 3 and 4-hydroxybenzaldehyde 9.

苏木心材中一个新黄酮类化合物

目的:从苏木Caesalpinia sappan中寻找新的活性成分。方法:用溶剂萃取及硅胶正相色谱进行活性成分的分离纯化,根据理化性质、光谱数据进行结构鉴定。结果:从苏木95%乙醇提取物中分离得到了9个化合物:3,8-dihydroxy-4,10-dimethoxy-7-oxo-[2]benzopyrano[4,3-b][1]benzopyran-7-(5H)-one(1),3-deoxysappanchal-cone(2),sappanchalcone(3),3-deoxysappanone B(4),鼠李素(rhamnetin,5),原苏木素C(protosappanin C,6),3,7-di-hydroxy-chroman-4-one(7),己二酸二甲酯(8),胡萝卜苷(daucosterin,9)。结论:化合物1为新化合物,化合物7,8为首次从该植物中分离得到。药理筛选结果表明,化合物3对多种癌细胞株具有一定的抑制活性。

Chemical Constituents of One Species of Endophytic Fungus in Taxus chinensis

Three compounds were obtained from the mycelia of an endophytic fungus Gliocladium sp. (designated as strain F) of Taxus chinensis (Pilg.) Rehd. growing in Fujian Province, China. Their structures were determined on the basis of spectral analysis. (20S,22S)-4a-homo-22-hydroxy-4-oxaergosta-7,24(28)-dien-3-one was a novel compound. 4,8,12,16-tetramethyl-1,5,9,13-tetraoxacyclohexadecane-2,6,10,14-tetraone was firstly isolated from the genus ofGliocladium and 6,9-epoxyergosta-7,22-dien-3-ol was firstly obtained from the strain F.

A New Halogenated Biindole and A New Apo-carotenone from Green Alga Chaetomorpha basiretorsa Setchell

A new halogenated biindole and a new apo-carotenone have been isolated from the ethanolic extract of the green alga Chaetomorpha basiretorsa Sethcell. On the basis of chemical and spectroscopic methods including 2D NMR technique, their structures have been elucidated as 4,4′-dichloro-5,5′-dibromo-7,7′-dimethoxy-2,2′-bi-1H-indole and 1′S*,4′R*-8-(4′-hydroxy-2′,6′,6′- trimethylcyclohex-2-enyl)-6-methyloct-3E,5E,7E-trien-2-one, respectively.

Two pairs of unusual scalemic enantiomers from Isatis indigotica leaves

Two pairs of unusual scalemic enantiomers with a dimethoxyphenyl）ethyl]-2-methoxyindolin-3-one, novel carbon skeleton of 2-[1′-（4＂-hydroxy-3＂,5＂- named isatidifoliumindolinones A-D （1-4）, were isolated from an aqueous extract of lsatis indigotica leaves （da qing ye）. Their structures including absolute configurations were determined by spectroscopic data analysis combined with comparison of their experimental CD and calculated ECD spectra. Validity of the ECD spectra calculation to assign the absolute configurations is discussed. Plausible biosynthetic pathways of 1-4 are proposed. Stereochemistry-dependent activity against LPS-induced NO production in BY2 cells was observed, and among the stereoisomers compound 4 is most active.

Two new terpenoids from Reduning Injection

Objective:To study the antipyretic and anti-inflammatory constituents from the active fraction of Reduning(RDN)Injection.Methods:In this study,the active fraction of RDN Injection was screened by the LPS-induced mouse endotoxin shock model.The chemical constituents were isolated by chromatography on HP-20 macroporous adsorptive resins,silica gel,ODS columns and reverse phase MPLC and HPLC repeatedly,and their structures were elucidated based on spectroscopic analysis(HR-ESI-MS,NMR,ECD)and chemical methods.Meanwhile,we evaluated the anti-inflammatory activities of the isolates by measuring their inhibitory effects on TNF-αproduction in LPS stimulated RAW 264.7 macrophages.Results:The 95%ethanol eluate of RDN Injection by the macroporous adsorption resin column was proved to be the antipyretic and anti-inflammatory active fraction of this injection.A novel iridoid,named jasminoide A(1),and a new guaiane sesquiterpenoid,named(1 R,7 R,8 S,10 R)-7,8,11-trihydroxy-4-guaien-3-one(2),were isolated from Reduning injection,and compound 2 can inhibit TNF-αproduction with IC50 values of 72.24μmol/L.Conclusion:In this study,two new terpenoids were isolated from Reduning Injection,and compound 2 showed inhibitory activity against LPS-activated TNF-αproduction in RAW 264.7 cells in vitro.