Three new compounds from the bark of Antiaris toxicaria

Three new compounds, namely (+)-pranferol (1), antiarone M (2), and anticerol A (3), together with 9 known compounds, were obtained from the bark of Antiaris toxicaria. Their chemical structures were elucidated on the basis of spectroscopic methods including UV, IR, (HR) ESI–MS, ¹H, ¹³C NMR, HSQC, ¹H-¹H COSY, HMBC and X-ray crystallographic technique. The absolute configurations of compounds 1 and 2 were determined by modified mosher method and CD spectrum.     

Synthesis and biological evaluation of water-soluble derivatives of chiral gossypol as HIV fusion inhibitors targeting gp41

A series of novel or known water-soluble derivatives of chiral gossypol were synthesized and screened in vitro for their anti-HIV-1 activity. (?)-gossypol derivative was more active against HIV-1 than the corresponding (+)-gossypol derivative, respectively. Among these derivatives, d-glucosamine derivative of (?)-gossypol, oligopeptide derivative of (?)-gossypol and taurine derivative of (?)-gossypol, such as compounds 1a, 3a and 14a, showed significant inhibitory activities against HIV-1 replication, HIV-1 mediated cell-cell fusion and HIV gp41 6-helix bundle formation as some amino acid derivatives of (?)-gossypol.     

Constituents of the genus Oxylobus

The aerial parts of Oxylobus arbutifolius and O. adscendens gave eudesmanolides and labdane derivatives as well as two new euparin derivatives.     

Types of sesquiterpenes from Artemisia filifolia

The roots of Artemisia filifolia afforded in addition to known compounds an oxo-longipinane, a longibornan endoperoxide, two seco-longibornane derivatives and a himachalene derivative. The structures of the new sesquiterpenes were elucidated by several chemical transformations and by NMR spectroscopic investigations. Possible biogenetic pathways are discussed briefly.     

Review Article Number 138: Constituents of the yew trees

Yew trees, taxonomically classified under the genus Taxus, are sources of a number of physiologically active compounds of different classes. Taxane derivatives with various carbon skeletons, lignans, flavonoids, steroids and sugar derivatives have been isolated from different Taxus species. Compounds isolated from the genus Taxus between 1908 and December 1997 have been comprehensively reviewed.     

Two sesquiterpenes from Senecio species

The investigation of further Senecio species gave, in addition to known compounds, two new sesquiterpenes, an eremophilane and a eudesmane derivative.     

4β,19-Epoxy-norkaurene and other diterpenes from Mikania banisteriae

The aerial parts of Mikania banisterae afforded four new diterpenes, ent-kaur-16-en-18-al, 18-acetoxy-ent-kaurene, 18-hydroxy-16α,17-epoxy-ent-kaurane and 4β-19-epoxy-18-nor-ent-kaurene.     

Synthesis of Triazole Nucleoside Derivatives

Abstract

5′-O-Mesyl-2′,3′-O-isopropylidene ribonucleosides (4 and 12) were converted to their 5′-substituted nucleosides in good yields by reacted with NaN₃ or KI. 2′,3′-O-Isopropylidene ribonucleosides (3 and 11) were prepared in good yields from ribonucleosides 1 and 2 with a reaction mixture of acetone and triethyl orthoformate instead of using acetone diethyl acetal. Compound 1 or 2 was treated with 2-acetoxyisobutyryl halide (Cl or Br) to give 1-[2-O-acetyl-3-halo-3-deoxy-5-O-(2,5,5-trimethyl-1,3-dioxolan-4-on-2-yl)-β-D-xylofuranosyl]-1,2,4-triazole-3-carboxamide (19, 22, and 23) in high yields. Instead of using 2-acetoxyisobutyryl bromide, the mixture of 2-acetoxyisobutyryl chloride and NaBr was employed in the synthesis of 22 and 23. Treatment of 19 with an activated Zn/Cu couple and deprotection gave 2′,3′-anhydro nucleoside (21), and treatment of 22 and 23 with an activated Zn/Cu couple and a little of HOAc and deprotection gave corresponding 2′,3′-unsaturated triazole nucleosides (24 and 25), respectively. The biological activity of the compounds (7 ～ 10, 15 ～ 18, and 24) was examined in human liver cancer cells (A-549), lung cancer cells (BEL-7402), and Flu-A cells.

Synthesis of Triazole Nucleoside Derivatives

All authors

Zicheng Li, Shuhua Chen, Ning Jiang & Gang Cui

https://doi.org/10.1081/NCN-120022032

Published online:

07 February 2007

Compound 1.     

9.

Ein neues bisabolen-derivat und ein neues dihydro kaffeesäure-derivat aus Tarchonanthus trilobus     

Ferdinand Bohlmann  Antoinette Suwita 《Phytochemistry》1979,18(4):677-678

     

10.

Enhanced spectrofluorimetric determination of two novel combination therapies for the treatment of benign prostatic hyperplasia containing tamsulosin hydrochloride          下载免费PDF全文

Eman I. El‐Kimary  Essam F. Khamis  Saeid F. Belal  Mona M. Abdel Moneim 《Luminescence》2018,33(4):771-779

Two novel combination therapies for the treatment of benign prostatic hyperplasia were analyzed using simple and enhanced spectrofluorimetric methods based on derivative and derivative ratio techniques. The two combinations contained tamsulosin hydrochloride (TAM) as a minor component with tolterodine tartrate (TOL) or solifenacin succinate (SOL). The fluorescence of the three drugs under study was measured in methanolic water solution. For the TAM and SOL mixture, successful resolution between both drugs was achieved by derivative manipulation of both ratio and zero‐order emission spectra with good linearity in the ranges of 0.75–3.50 and 2.5–15.0 μg ml^?1 for TAM and SOL, respectively. Extensive emission spectral overlap was observed for the TAM and TOL mixture. Therefore, only derivative application of the ratio emission spectra resolved such overlap and quantitated TAM and TOL simultaneously in the ranges 0.75–3.50 and 2.5–20.0 μg ml^–1 for TAM and TOL, respectively. Optimization of various experimental parameters that affected the fluorescence intensity of the three drugs was performed. Successful application of all proposed methods was achieved for analysis of the two drugs in each combination therapy in their laboratory‐prepared mixtures and dosage forms with good accuracy and precision.     

11.

Asperidines A–C,pyrrolidine and piperidine derivatives from the soil-derived fungus Aspergillus sclerotiorum PSU-RSPG178     

Patima Phainuphong  Vatcharin Rukachaisirikul  Saowanit Saithong  Souwalak Phongpaichit  Jariya Sakayaroj  Chutima Srimaroeng  Atcharaporn Ontawong  Acharaporn Duangjai  Paradorn Muangnil  Chatchai Muanprasat 《Bioorganic & medicinal chemistry》2018,26(15):4502-4508

One new pyrrolidine derivative, asperidine A (1), and two new piperidine derivatives, asperidines B (2) and C (3), were isolated from the soil-derived fungus Aspergillus sclerotiorum PSU-RSPG178 together with two known alkaloids. Compound 3 possessed an unprecedented 7-oxa-1-azabicyclo[3.2.1]octane skeleton with four chiral centers. Their structures were determined by spectroscopic evidence. The absolute configurations of compounds 2 and 3 were established using Mosher’s method and further confirmed for compound 3 by X-ray crystallographic data. Compound 2 dose-dependently inhibited the CFTR-mediated chloride secretion in T84 cells with an IC₅₀ value of 0.96?μM whereas 3 displayed the same activity with the IC₅₀ value of 58.62?μM. Compounds 2 and 3 also significantly reduced intracellular ROS under both normal and H₂O₂-treated conditions compared with their respective controls in a dose-dependent manner without cytotoxic effect on Caco-2 cells. In addition, compound 3 was inactive against noncancerous Vero cells whereas compound 2 was considered to be inactive with the IC₅₀ value of >10?μM.     

12.

Activity of a nitroalkene derivative, 1-(5-bromofur-2-il)-2-bromo-2-nitroethene, in the Salmonella/microsome assay and the mouse bone marrow micronucleus test     

Alberto Ramos  Angel Vizoso  Aymeé Edreira  José Betancourt  Mercedes Décalo 《Mutation Research - Genetic Toxicology and Environmental Mutagenesis》1997,390(3):233

Mutagenicity of a substituted nitroalkene, 1-(5-bromofur-2-il)-2-bromo-2-nitroethene (BNF) was tested in the Salmonella/microsome assay using the strains TA 98, TA 100 and TA 100NR (nitroreductase deficient). BNF was a direct mutagen in TA 98 and TA 100; the response was lowered when exogenous metabolic activation (S9) was used. A further decrease in mutagenicity was observed in strain TA 100NR, as compared to the parental TA 100, which showed the involvement of nitroreduction in the overall response elicited by BNF. The micronucleus assay was carried out in Swiss male mice which were given a single i.p. dose of 10–20 mg/kg of BNF dissolved in peanut oil, bone marrow being sampled 24 and 48 h later. The micronucleated polychromatic erythrocyte counts (MNPCE) showed a weak response in the dose range of 10–17.5 mg/kg at the second sampling (48 h) and a significant rise for 20 mg/kg at 24 and 48 h.     

13.

Ein neues Kaurensäure- und ein euparin-derivat aus Oyedaea-arten     

Ferdinand Bohlmann  Christa Zdero 《Phytochemistry》1979,18(3):492-493

     

14.

A series of heteroleptic complexes of the type fac-[MnL₂] [H₂L=derivatives of N-(2-hydroxybenzyl)glycine or N-(5-nitro-2-hydroxybenzyl)sarcosine] possessing unusual Mn(III) co-ordination spheres     

Musa S. Shongwe  Masahiro Mikuriya  Ryoji Nukada  Eric W. Ainscough  Andrew M. Brodie  Joyce M. Waters 《Inorganica chimica acta》1999,290(2):o1366-236

The mononuclear manganese(III) complexes [C₅H₁₀NH₂][MnL₂] [L²⁻=a substituted N-(2-hydroxybenzyl)glycinate (hbg²⁻) viz. 3,5-dibromo- (3,5-Br-hbg²⁻), 3,5-dichloro- (3,5-Cl-hbg²⁻), 3-methyl-5-chloro- (3,5-Me,Cl-hbg²⁻), 5-bromo- (5-Br-hbg²⁻), 5-chloro- (5-Cl-hbg²⁻), 5-nitro- (5-NO₂-hbg²⁻) or N-(5-nitro-2-hydroxybenzyl)sarcosine (5-NO₂-hbs²⁻)] have been synthesised by reaction of the appropriate ligand with manganese(II) perchlorate under ambient conditions in a 2:1 molar ratio using piperidine as base. The structures of three of these complexes, [C₅H₁₀NH₂][Mn(3,5-Cl-hbg)₂] (2), [C₅H₁₀NH₂][Mn(5-NO₂-hbg)₂] (6) and [C₅H₁₀NH₂][Mn(5-NO₂-hbs)₂] (7) have been elucidated by single-crystal X-ray crystallography and each displays two similar, independent [MnL₂]⁻ ions in the asymmetric unit linked via piperidinium cations through hydrogen bonding. The ligands co-ordinate in a facial tridentate fashion with the three donor atoms being the phenolate and carboxylate oxygens and the amine nitrogen. The geometry at the Mn centres is compressed rhombic octahedral consistent with a pseudo-Jahn–Teller compression along the Mn–O(phenolate) axis. Mean bond lengths are in the ranges 1.886–1.889 Å for the Mn–O(phenolate), 2.062–2.125 Å for the Mn–O(carboxylate) and 2.091–2.184 Å for the Mn–N(amine) distances. The magnetic susceptibility and electronic and IR spectroscopic data are discussed with reference to the crystal structures.     

15.

Neue tremeton-derivate aus Parastrephia lepidophylla     

Ferdinand Bohlmann  Ulrich Fritz  Robert M. King 《Phytochemistry》1979,18(8):1403-1405

     

16.

Ein neues germacren-derivat sowie ein diterpenmalonat aus Baccharis-arten     

Ferdinand Bohlmann  Christa Zdero  Harold Robinson  Robert M. King 《Phytochemistry》1979,18(12):1993-1996

The investigation of the aerial part of B. scandens afforded a new ketone, a germacrene derivative. The aerial parts of B. tricuneata var. lineata yielded, in addition to known ent-clerodane derivatives, a malonate of a further diterpene of this type. The structures are elucidated by spectroscopic methods.     

17.

Neue C10-säureamide,furanoeremophilane und andere inhaltsstoffe aus bolivianischen Senecio-arten     

Ferdinand Bohlmann  Christa Zdero 《Phytochemistry》1979,18(1):125-128

The investigation of seven Bolivian Senecio species afforded in addition to known compounds five new furanoeremophilanes, two C₁₀-amides, a new isoeugenol ester and the isomer of pterophorin. The structures are elucidated mainly by spectroscopic methods. While most of the new compounds are closely related to those isolated before from Senecio species, four of them are unusual. Another is a new type of a furanoeremophilane; its biogenesis however, can be explained easily from known types.     

18.

钙调素拮抗剂──双苄基异喹啉类化合物结构与活性关系的研究     

陈少林  胡卓逸  郝志奇  蔡惠明  黄文龙 《中国生物化学与分子生物学报》1990,6(5):413-416

 双苄基异喹啉类化合物拮抗钙调素(CaM),抑制CaM激活的环核苷酸磷酸二酯酶(PDE),研究表明:蝙蝠葛碱和小檗胺分子中12位羟墓被芳香基团酯化或醚化时,芳香基团的电子云分布状态变化能增加或降低分子的拮抗活性;取代基中的次甲基数增加可以增强分子的拮抗活性。分子非极性端引入含氮基团,化合物的拮抗活性较低。测试的化合物中,E_6D_(12)和D_(14)的拮抗CaM活性较强,IC_(50)分别为0.58μmol/L0.58μmol/L和0.53μmol/L。实验结果表明,分子的拮抗活性与分子非极性端的疏水性、电子云分布状态以及分子空间结构等多种结构性质相关。     

19.

Synthesis and antimicrobial activity of a water-soluble chitosan derivative with a fiber-reactive group   总被引：25，自引：0，他引：25  

Lim SH  Hudson SM 《Carbohydrate research》2004,339(2):313-319

A novel fiber-reactive chitosan derivative was synthesized in two steps from a chitosan of low molecular weight and low degree of acetylation. First, a water-soluble chitosan derivative, N-[(2-hydroxy-3-trimethylammonium)propyl]chitosan chloride (HTCC), was prepared by introducing quaternary ammonium salt groups on the amino groups of chitosan. This derivative was further modified by introducing functional (acrylamidomethyl) groups, which can form covalent bonds with cellulose under alkaline conditions, on the primary alcohol groups (C-6) of the chitosan backbone. The fiber-reactive chitosan derivative, O-acrylamidomethyl-HTCC (NMA-HTCC), showed complete bacterial reduction within 20 min at the concentration of 10ppm, when contacted with Staphylococcus aureus and Escherichia coli (1.5-2.5 x 10(5) colony forming units per milliliter [CFU/mL]).     

20.

A prenylated dihydroflavonol from Mundulea suberosa     

E. Venkata Rao  P. Sridhar  B. V. L. Narasimha Rao  P. Ellaiah 《Phytochemistry》1999,50(8):5423

A new prenylated dihydroflavonol was isolated from Mundulea suberosa and characterised as 5-methyl lupinifolinol by spectral data. Its antibacterial activity was studied.     

Enhanced spectrofluorimetric determination of two novel combination therapies for the treatment of benign prostatic hyperplasia containing tamsulosin hydrochloride

Two novel combination therapies for the treatment of benign prostatic hyperplasia were analyzed using simple and enhanced spectrofluorimetric methods based on derivative and derivative ratio techniques. The two combinations contained tamsulosin hydrochloride (TAM) as a minor component with tolterodine tartrate (TOL) or solifenacin succinate (SOL). The fluorescence of the three drugs under study was measured in methanolic water solution. For the TAM and SOL mixture, successful resolution between both drugs was achieved by derivative manipulation of both ratio and zero‐order emission spectra with good linearity in the ranges of 0.75–3.50 and 2.5–15.0 μg ml^?1 for TAM and SOL, respectively. Extensive emission spectral overlap was observed for the TAM and TOL mixture. Therefore, only derivative application of the ratio emission spectra resolved such overlap and quantitated TAM and TOL simultaneously in the ranges 0.75–3.50 and 2.5–20.0 μg ml^–1 for TAM and TOL, respectively. Optimization of various experimental parameters that affected the fluorescence intensity of the three drugs was performed. Successful application of all proposed methods was achieved for analysis of the two drugs in each combination therapy in their laboratory‐prepared mixtures and dosage forms with good accuracy and precision.     

Asperidines A–C,pyrrolidine and piperidine derivatives from the soil-derived fungus Aspergillus sclerotiorum PSU-RSPG178

One new pyrrolidine derivative, asperidine A (1), and two new piperidine derivatives, asperidines B (2) and C (3), were isolated from the soil-derived fungus Aspergillus sclerotiorum PSU-RSPG178 together with two known alkaloids. Compound 3 possessed an unprecedented 7-oxa-1-azabicyclo[3.2.1]octane skeleton with four chiral centers. Their structures were determined by spectroscopic evidence. The absolute configurations of compounds 2 and 3 were established using Mosher’s method and further confirmed for compound 3 by X-ray crystallographic data. Compound 2 dose-dependently inhibited the CFTR-mediated chloride secretion in T84 cells with an IC₅₀ value of 0.96?μM whereas 3 displayed the same activity with the IC₅₀ value of 58.62?μM. Compounds 2 and 3 also significantly reduced intracellular ROS under both normal and H₂O₂-treated conditions compared with their respective controls in a dose-dependent manner without cytotoxic effect on Caco-2 cells. In addition, compound 3 was inactive against noncancerous Vero cells whereas compound 2 was considered to be inactive with the IC₅₀ value of >10?μM.     

Activity of a nitroalkene derivative, 1-(5-bromofur-2-il)-2-bromo-2-nitroethene, in the Salmonella/microsome assay and the mouse bone marrow micronucleus test

Mutagenicity of a substituted nitroalkene, 1-(5-bromofur-2-il)-2-bromo-2-nitroethene (BNF) was tested in the Salmonella/microsome assay using the strains TA 98, TA 100 and TA 100NR (nitroreductase deficient). BNF was a direct mutagen in TA 98 and TA 100; the response was lowered when exogenous metabolic activation (S9) was used. A further decrease in mutagenicity was observed in strain TA 100NR, as compared to the parental TA 100, which showed the involvement of nitroreduction in the overall response elicited by BNF. The micronucleus assay was carried out in Swiss male mice which were given a single i.p. dose of 10–20 mg/kg of BNF dissolved in peanut oil, bone marrow being sampled 24 and 48 h later. The micronucleated polychromatic erythrocyte counts (MNPCE) showed a weak response in the dose range of 10–17.5 mg/kg at the second sampling (48 h) and a significant rise for 20 mg/kg at 24 and 48 h.     

A series of heteroleptic complexes of the type fac-[MnL2] [H2L=derivatives of N-(2-hydroxybenzyl)glycine or N-(5-nitro-2-hydroxybenzyl)sarcosine] possessing unusual Mn(III) co-ordination spheres

The mononuclear manganese(III) complexes [C₅H₁₀NH₂][MnL₂] [L²⁻=a substituted N-(2-hydroxybenzyl)glycinate (hbg²⁻) viz. 3,5-dibromo- (3,5-Br-hbg²⁻), 3,5-dichloro- (3,5-Cl-hbg²⁻), 3-methyl-5-chloro- (3,5-Me,Cl-hbg²⁻), 5-bromo- (5-Br-hbg²⁻), 5-chloro- (5-Cl-hbg²⁻), 5-nitro- (5-NO₂-hbg²⁻) or N-(5-nitro-2-hydroxybenzyl)sarcosine (5-NO₂-hbs²⁻)] have been synthesised by reaction of the appropriate ligand with manganese(II) perchlorate under ambient conditions in a 2:1 molar ratio using piperidine as base. The structures of three of these complexes, [C₅H₁₀NH₂][Mn(3,5-Cl-hbg)₂] (2), [C₅H₁₀NH₂][Mn(5-NO₂-hbg)₂] (6) and [C₅H₁₀NH₂][Mn(5-NO₂-hbs)₂] (7) have been elucidated by single-crystal X-ray crystallography and each displays two similar, independent [MnL₂]⁻ ions in the asymmetric unit linked via piperidinium cations through hydrogen bonding. The ligands co-ordinate in a facial tridentate fashion with the three donor atoms being the phenolate and carboxylate oxygens and the amine nitrogen. The geometry at the Mn centres is compressed rhombic octahedral consistent with a pseudo-Jahn–Teller compression along the Mn–O(phenolate) axis. Mean bond lengths are in the ranges 1.886–1.889 Å for the Mn–O(phenolate), 2.062–2.125 Å for the Mn–O(carboxylate) and 2.091–2.184 Å for the Mn–N(amine) distances. The magnetic susceptibility and electronic and IR spectroscopic data are discussed with reference to the crystal structures.     

Ein neues germacren-derivat sowie ein diterpenmalonat aus Baccharis-arten

The investigation of the aerial part of B. scandens afforded a new ketone, a germacrene derivative. The aerial parts of B. tricuneata var. lineata yielded, in addition to known ent-clerodane derivatives, a malonate of a further diterpene of this type. The structures are elucidated by spectroscopic methods.     

Neue C10-säureamide,furanoeremophilane und andere inhaltsstoffe aus bolivianischen Senecio-arten

The investigation of seven Bolivian Senecio species afforded in addition to known compounds five new furanoeremophilanes, two C₁₀-amides, a new isoeugenol ester and the isomer of pterophorin. The structures are elucidated mainly by spectroscopic methods. While most of the new compounds are closely related to those isolated before from Senecio species, four of them are unusual. Another is a new type of a furanoeremophilane; its biogenesis however, can be explained easily from known types.     

钙调素拮抗剂──双苄基异喹啉类化合物结构与活性关系的研究

 双苄基异喹啉类化合物拮抗钙调素(CaM),抑制CaM激活的环核苷酸磷酸二酯酶(PDE),研究表明:蝙蝠葛碱和小檗胺分子中12位羟墓被芳香基团酯化或醚化时,芳香基团的电子云分布状态变化能增加或降低分子的拮抗活性;取代基中的次甲基数增加可以增强分子的拮抗活性。分子非极性端引入含氮基团,化合物的拮抗活性较低。测试的化合物中,E_6D_(12)和D_(14)的拮抗CaM活性较强,IC_(50)分别为0.58μmol/L0.58μmol/L和0.53μmol/L。实验结果表明,分子的拮抗活性与分子非极性端的疏水性、电子云分布状态以及分子空间结构等多种结构性质相关。     

Synthesis and antimicrobial activity of a water-soluble chitosan derivative with a fiber-reactive group

A novel fiber-reactive chitosan derivative was synthesized in two steps from a chitosan of low molecular weight and low degree of acetylation. First, a water-soluble chitosan derivative, N-[(2-hydroxy-3-trimethylammonium)propyl]chitosan chloride (HTCC), was prepared by introducing quaternary ammonium salt groups on the amino groups of chitosan. This derivative was further modified by introducing functional (acrylamidomethyl) groups, which can form covalent bonds with cellulose under alkaline conditions, on the primary alcohol groups (C-6) of the chitosan backbone. The fiber-reactive chitosan derivative, O-acrylamidomethyl-HTCC (NMA-HTCC), showed complete bacterial reduction within 20 min at the concentration of 10ppm, when contacted with Staphylococcus aureus and Escherichia coli (1.5-2.5 x 10(5) colony forming units per milliliter [CFU/mL]).     

A prenylated dihydroflavonol from Mundulea suberosa

A new prenylated dihydroflavonol was isolated from Mundulea suberosa and characterised as 5-methyl lupinifolinol by spectral data. Its antibacterial activity was studied.