0000000000136275
AUTHOR
Yu Zhao
Synthesis and structure-activity relationship studies of cytotoxic cinnamic alcohol derivatives.
Three series of di- and trisubstituted derivatives of cinnamic alcohol and its conjugated dienol analogues were designed and synthesised. The derivatives were screened for cytotoxicity against nine tumour cell lines: KB, A549, Hela, CNE, PC-3, BEL-7404, HL-60, BGC823 and P388D1. Most of the cinnamic alcohol derivatives showed cytotoxic activity. The compound 7-(4',5'-dichlorobenzyloxy)-6,8-dihydroxycinnamic alcohol (55) exhibited significant cytotoxicity to seven human tumour cell lines on a micromolar range, especially with regard to the KB and P388D1 cell lines, showing IC(50) values of 0.4 and 0.5 µM, respectively. The structure-activity relationships of the derivatives are discussed.
A new dibenzofuran and other constituents from Ligularia caloxantha, a Chinese medicinal plant.
A new dibenzofuran named 1,2,4-trimethyl-7,8-dimethoxy-dibenzofuran (1), together with seven known compounds, euparin (2), 2,5-diacetyl-6-hydroxy-benzofuran (3), 2-acetyl-5,6-dimethoxy-benzofuran (4), gummosogenin (5), lupeol (6), stigmasterol (7) and (E)-2,5-dihydroxy-cinnamic acid (8), were isolated from the roots of Ligularia caloxantha, a Chinese medicinal plant. The structures of the compounds were elucidated by spectroscopic methods.
Lignans from Torreya jackii identified by stopped-flow high-performance liquid chromatography–nuclear magnetic resonance spectroscopy
Abstract Coupled reversed-phase HPLC–NMR spectroscopy has been applied to the rapid detection and identification of plant metabolites of Torreya jackii , a species of Taxaceae. Analysis consisted of gradient HPLC elution and directly coupled 1 H NMR (500 MHz) spectroscopic detection in a stopped-flow mode. Seven lignans were detected and their structures were elucidated, based on their HPLC– 1 H NMR spectra and MS data. The structures were confirmed by isolation of the single components followed by conventional NMR measurements.
Antioxidant and neuroprotective effects of synthesized sintenin derivatives
Three series of sintenin derivatives (compounds 1-14) were designed and prepared and their antioxidative and neuroprotective effects were evaluated. The in vitro models of scavenging 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals, chelating ferrous ions, inhibiting the rat brain homogenates lipid peroxidation, and protecting neurons damaged by hydrogen peroxide were employed for bioassays. It was found that sintenin derivatives 4 and 13 showed remarkable antioxidative and neuroprotective activities.
Synthesis and antioxidant evaluation of novel silybin analogues
In this work, we evaluated the antioxidant properties of the eight novel silybin analogues for their capacity to scavenge free radicals including superoxide anion radicals and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals in vitro. Compound 7d demonstrated an excellent antioxidant effect in scavenging superoxide anion free radical with an IC50 value of 26.5 microM, while the IC50 of quercetin (the reference compound) was 38.1 microM. Compounds 7b, 7e, 7h showed certain scavenging activities for both types of free radicals.
Preparation of C-23 esterified silybin derivatives and evaluation of their lipid peroxidation inhibitory and DNA protective properties.
A diverse series of C-23 esterified silybin derivatives (1a-n) were designed and synthesized. The antioxidative properties of these compounds were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) and superoxide anion radical scavenging, ferrous ion chelation, and inhibition of rat liver homogenate lipid peroxidation. Their protective effects on the prevention of hydrogen peroxide induced DNA damage were also investigated. Most of the synthesized compounds exhibited more effective antioxidant activities than silybin. The esterified silybin analogues displayed satisfactory performance especially on iron chelation and antiperoxidative activity. Compound 1n in particular exhibited remarkable a…
Preparation of ferulic acid derivatives and evaluation of their xanthine oxidase inhibition activity.
Several ferulic acid ethyl esters (3a-h) were synthesized under the Knoevengel reaction condition and they were further reduced to afford the respective allylic alcohol derivatives (4a-g). Some of them were evaluated for the xanthine oxidase (XO) inhibitory activity. Among them, 3h exhibited a significant inhibitory activity with an IC50 value of 1.35 x 10(-5) M, while the IC50 value of allopurinol used as the positive control was 1.49 x 10(-5) M. The study suggested that the higher acidity of the phenolic OH group in the ferulic acid derivatives might result in improved XO inhibitory activity.
Design, synthesis, and SAR analysis of cytotoxic sinapyl alcohol derivatives.
Five series totalling 51 of sinapyl alcohol derivatives were designed and synthesized. Their cytotoxicity analyses were performed oil six human tumor cell lines Such as PC-3. CNE, KB, A549, BEL-7404, and HeLa. Certain sinapyl alcohol derivatives showed significant cytotoxic activities. Compound 14d exhibited especially potent cytotoxicity against the BEL-7404 cell line with an IC50 value of 0.7 mu M, which showed more cytotoxic activity than the positive control, cisplatin. The structure-cytotoxicity relationships were discussed and the CoMFA analysis was performed using the cytotoxic data against HeLa cells as a template. (c) 2005 Elsevier Ltd. All rights reserved.
Eremophilane Derivatives with a Novel Carbon Skeleton from Ligularia veitchiana
Abstract Ligulaverin A 1, an eremophilane derivative with a novel carbon skeleton, was isolated from the medicinal plant Ligularia veitchiana, along with four analogues (ligulaverin B 2, ligulaverin C 3, ligulaverin D 4 and ligulaverin E 5). Their structures were elucidated by NMR techniques and X-ray diffraction. The biosynthetic route to this nineteen-carbon skeleton is discussed. © 1997 Elsevier Science Ltd.
Synthesis, biological evaluation, and structure-activity relationship study of novel cytotoxic aza-caffeic acid derivatives.
Abstract Three series of aza-caffeic acid derivatives with different linkers were designed and synthesized. Each of the synthesized derivatives was then used in cytotoxicity screening on either 8 or 12 human cancer cell lines. The structure–activity relationships on three structural regions A, B, and C are analyzed in detail, indicating that a nine bond linker B, containing a piperazine unit, is the most favorable linker leading to the generation of molecules with potent cytotoxicities. Compound ( E )-1-(4-(3,4-dichlorobenzyl)piperazin-1-yl)-3-(4-(4-ethoxybenzyloxy)-3,5-dimethoxyphenyl)prop-2-en-1-one ( 80 ) exhibited the most significant and selective cytotoxicity to KB, BEL7404, K562, and…
Expression, purification, crystallization and preliminary X-ray analysis of perakine reductase, a new member of the aldo-keto reductase enzyme superfamily from higher plants
Perakine reductase (PR) is a novel member of the aldo-keto reductase enzyme superfamily from higher plants. PR from the plant Rauvolfia serpentina is involved in the biosynthesis of monoterpenoid indole alkaloids by performing NADPH-dependent reduction of perakine, yielding raucaffrinoline. However, PR can also reduce cinnamic aldehyde and some of its derivatives. After heterologous expression of a triple mutant of PR in Escherichia coli, crystals of the purified and methylated enzyme were obtained by the hanging-drop vapour-diffusion technique at 293 K with 100 mM sodium citrate pH 5.6 and 27% PEG 4000 as precipitant. Crystals belong to space group C222(1) and diffract to 2.0 A, with unit-…
Taxane analysis by high performance liquid chromatography-Nuclear magnetic resonance spectroscopy ofTaxus species
High performance liquid chromatography–nuclear magnetic resonance spectroscopic analyses of taxane diterpenoids from three Taxus species were carried out employing a stopped-flow technique. Several taxanes have been identified from 500 mg leaf samples without prior isolation. © 1998 John Wiley & Sons, Ltd.
Four new eremophilendiolides from Ligularia atroviolacea
From Ligularia atroviolacea, four new eremophilendiolides, 8 beta-hydroxy-eremophil-3,7 (11)-dien-12,8 alpha(14,6 alpha)-diolide (1), 8 beta-methoxy-eremophil-3,7(11)-dien-12,8 alpha(14,6 alpha)-diolide (2), 8 alpha-hydroxy-eremophil-3,7(11)-dien-12,8 beta(14,6 alpha)-diolide (3) and eremophil-3,7(11),8-trien-12,8 (14,6 alpha)-diolide (4), as well as a known diolide (5) were isolated. Their structures were elucidated on the basis of 1D and 2D NMR as well as ESI-MS spectral data. (c) 2006 Yu Zhao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
Preparation of two sets of 5,6,7-trioxygenated dihydroflavonol derivatives as free radical scavengers and neuronal cell protectors to oxidative damage.
An unusual class of 5,6,7-trioxygenated dihydroflavonols (3a-e and 4a-j) were designed and prepared. Their antioxidative properties were assessed by examining their capacities in several in vitro models, including superoxide anion and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, rat liver homogenate lipid peroxidation inhibition, PC12 cells protection from oxidative damage, and xanthine oxidase inhibition. These dihydroflavonols displayed positive quenching abilities towards O(2)(-) and DPPH free radicals, in which the majority exhibited superior antioxidant properties to Vitamin C. cis-Configurated compound (+/-)-3e demonstrated remarkable inhibition to LPO with an IC(50) value…
CSD 1838368: Experimental Crystal Structure Determination
Related Article: Li‐Cheng Yang, Zher Yin Tan, Zi‐Qiang Rong, Ruoyang Liu, Ya‐Nong Wang, Yu Zhao|2018|Angew.Chem.,Int.Ed.|57|7860|doi:10.1002/anie.201804160
CSD 1838401: Experimental Crystal Structure Determination
Related Article: Li‐Cheng Yang, Zher Yin Tan, Zi‐Qiang Rong, Ruoyang Liu, Ya‐Nong Wang, Yu Zhao|2018|Angew.Chem.,Int.Ed.|57|7860|doi:10.1002/anie.201804160
CSD 1838364: Experimental Crystal Structure Determination
Related Article: Li‐Cheng Yang, Zher Yin Tan, Zi‐Qiang Rong, Ruoyang Liu, Ya‐Nong Wang, Yu Zhao|2018|Angew.Chem.,Int.Ed.|57|7860|doi:10.1002/anie.201804160