118-41-2Relevant articles and documents
Cloning and heterologous expression of two aryl-aldehyde dehydrogenases from the white-rot basidiomycete Phanerochaete chrysosporium
Nakamura, Tomofumi,Ichinose, Hirofumi,Wariishi, Hiroyuki
, p. 470 - 475 (2010)
We identified two aryl-aldehyde dehydrogenase proteins (PcALDH1 and PcALDH2) from the white-rot basidiomycete Phanerochaete chrysosporium. Both PcALDHs were translationally up-regulated in response to exogenous addition of vanillin, one of the key aromatic compounds in the pathway of lignin degradation by basidiomycetes. To clarify the catalytic functions of PcALDHs, we isolated full-length cDNAs encoding these proteins and heterologously expressed the recombinant enzymes using a pET/Escherichia coli system. The open reading frames of both PcALDH1 and PcALDH2 consisted of 1503 nucleotides. The deduced amino acid sequences of both proteins showed high homologies with aryl-aldehyde dehydrogenases from other organisms and contained ten conserved domains of ALDHs. Moreover, a novel glycine-rich motif "GxGxxxG" was located at the NAD+-binding site. The recombinant PcALDHs catalyzed dehydrogenation reactions of several aryl-aldehyde compounds, including vanillin, to their corresponding aromatic acids. These results strongly suggested that PcALDHs metabolize aryl-aldehyde compounds generated during fungal degradation of lignin and various aromatic xenobiotics.
Cytotoxic cholestane glycosides from the bulbs of Ornithogalum saundersiae
Kuroda, Minpei,Mimaki, Yoshihiro,Yokosuka, Akihito,Sashida, Yutaka,Beutler, John A.
, p. 88 - 91 (2001)
Further phytochemical analysis of the bulbs of Ornithogalum saundersiae has yielded two new cytotoxic cholestane triglycosides (1 and 2). The structures of these compounds were determined by spectroscopic analysis, including 2D NMR spectroscopic data, and
One pot synthesis of α-aminophosphonates containing bromo and 3,4,5-trimethoxybenzyl groups under solvent-free conditions
Li, Caihong,Song, Baoan,Yan, Kai,Xu, Gangfang,Hu, Deyu,Yang, Song,Jin, Linhong,Xue, Wei,Lu, Ping
, p. 163 - 172 (2007)
New α-aminophosphonates were synthesized by the Kabachnik-Fields reaction of 3,4,5-trimethoxybenzaldehyde (TMB) with p- or m-bromoaniline and a dialkyl phosphite under solvent-free conditions. TMB was prepared from gallic acid via a four step synthetic sequence involving etherification, esterification, hydrazidation and potassium ferricyanide oxidation. The structures of all synthesized compounds were confirmed by elemental analysis, IR, 1H-, 13C- and 31P-NMR spectral data. Compound 7g was also characterized by X-ray crystallography. A half-leaf method was used to determine the in vivo curative efficacy of the eight title products against tobacco mosaic virus (TMV). It was found that compounds 7g and 7h possess good in vivo curative effects against TMV.
ALSTOLENINE, 19,20-DIHYDROPOLYNEURIDINE AND OTHER MINOR ALKALOIDS OF THE LEAVES OF ALSTONIA VENENATA
Majumder, Priyalal,Basu, Ashoke
, p. 2389 - 2392 (1982)
Structures of alstolenine and 19,20-dihydropolyneuridine, two new indole alkaloids of the leaves of Alstonia venenata have been established.In addition, deacetylakuammiline, polyneuridine and raucaffrinoline have been isolated for the first time from this plant.Key Word Index-Alstonia venenata; Apocynaceae; alstolenine; 19,20-dihydropolyneuridine; polyneuridine; deacetylakuammiline; raucaffrinoline; indol alkaloids.
The Selective Liquid-Phase Oxidation of 3,4,5-Trimethoxytoluene to 3,4,5-Trimethoxybezaldehyde
Kitajima, Nobumasa,Takemura, Kazuya,Moro-Oka, Yoshihiko,Yoshikuni, Tadatsugu,Akada, Mitsuo,et al.
, p. 1035 - 1038 (1988)
The selective liquid-phase oxidation of 3,4,5-trimethoxytoluene to 3,4,5-trimethoxybenzaldehyde, an important chemical intermediate for medicine production, was developed; when 2.0 mmol of the reactant was heated at 110 deg C for 2 h in an autoclave under 3 atm O2 with 10 ml of acetic acid in the presence of 0.75 mmol of Co(OAc)2-Mn(OAc)2 (3:1 mol ratio), a 92percent yield of the aldehyde was obtained.
Solvolysis, Electrochemistry, and Development of Synthetic Building Blocks from Sawdust
Nguyen, Bichlien H.,Perkins, Robert J.,Smith, Jake A.,Moeller, Kevin D.
, p. 11953 - 11962 (2015)
Either aldehyde or cinnamyl ether products can be selectively extracted from raw sawdust by controlling the temperature and pressure of a solvolysis reaction. These materials have been used as platform chemicals for the synthesis of 15 different synthetic substrates. The conversion of the initial sawdust-derived materials into electron-rich aryl substrates often requires the use of oxidation and reduction chemistry, and the role electrochemistry can play as a sustainable method for these transformations has been defined.
Synthesis and antitumor activity of novel 6,7,8-trimethoxy N-aryl-substituted-4-aminoquinazoline derivatives
Liu, Fang,Huai, Ziyou,Xia, Guotai,Song, Liuping,Li, Sha,Xu, Yulan,Hong, Kangjun,Yao, Mingyue,Liu, Gang,Huang, Yinjiu
, p. 2561 - 2565 (2018)
A series of 6,7,8-trimethoxy N-aryl-substituted-4-aminoquinazoline derivatives were synthesized as epidermal growth factor receptor (EGFR) inhibitors, and their antitumor activities were assessed in the gastric cancer cell line SGC7901 using MTT assay. All compounds of Tg1–14 were found to inhibit SGC7901 cell proliferation, and compound Tg11 (IC50 = 0.434 μM) was found to be slightly more effective against SGC7901 cells than epirubicin (IC50 = 5.16 μM). This suggests that compound Tg11 can be used as a new substitution structure to develop more efficacious antitumor agents. Western blot analysis showed that treatment with Tg11 (40 μM for 30 min) resulted in near complete inhibition of EGF-induced ERK1/2 phosphorylation, indicating that its anti-proliferative effect is largely associated with inhibition of ERK1/2 activation. These data imply that Tg11 is a potential anticancer agent capable of inhibiting cell proliferation.
One-Pot Biocatalytic In Vivo Methylation-Hydroamination of Bioderived Lignin Monomers to Generate a Key Precursor to L-DOPA
Birmingham, William R.,Galman, James L.,Parmeggiani, Fabio,Seibt, Lisa,Turner, Nicholas J.
, (2022/01/13)
Electron-rich phenolic substrates can be derived from the depolymerisation of lignin feedstocks. Direct biotransformations of the hydroxycinnamic acid monomers obtained can be exploited to produce high-value chemicals, such as α-amino acids, however the reaction is often hampered by the chemical autooxidation in alkaline or harsh reaction media. Regioselective O-methyltransferases (OMTs) are ubiquitous enzymes in natural secondary metabolic pathways utilising an expensive co-substrate S-adenosyl-l-methionine (SAM) as the methylating reagent altering the physicochemical properties of the hydroxycinnamic acids. In this study, we engineered an OMT to accept a variety of electron-rich phenolic substrates, modified a commercial E. coli strain BL21 (DE3) to regenerate SAM in vivo, and combined it with an engineered ammonia lyase to partake in a one-pot, two whole cell enzyme cascade to produce the l-DOPA precursor l-veratrylglycine from lignin-derived ferulic acid.
Polyhydroxybenzoic acid derivatives as potential new antimalarial agents
Degotte, Gilles,Francotte, Pierre,Pirotte, Bernard,Frédérich, Michel
, (2021/08/07)
With more than 200 million cases and 400,000 related deaths, malaria remains one of the deadliest infectious diseases of 2021. Unfortunately, despite the availability of efficient treatments, we have observed an increase in people infected with malaria since 2015 (from 211 million in 2015 to 229 million in 2019). This trend could partially be due to the development of resistance to all the current drugs. Therefore, there is an urgent need for new alternatives. We have, thus, selected common natural scaffolds, polyhydroxybenzoic acids, and synthesized a library of derivatives to better understand the structure–activity relationships explaining their antiplasmodial effect. Only gallic acid derivatives showed a noticeable potential for further developments. Indeed, they showed a selective inhibitory effect on Plasmodium (IC50 ~20 μM, SI > 5) often associated with interesting water solubility. Moreover, this has confirmed the critical importance of free phenolic functions (pyrogallol moiety) for the antimalarial effect. Methyl 4-benzoxy-3,5-dihydroxybenzoate (39) has, for the first time, been recognized as a potential lead for future research because of its marked inhibitory activity against Plasmodium falciparum and its significant hydrosolubility (3.72 mM).
Selectively Upgrading Lignin Derivatives to Carboxylates through Electrochemical Oxidative C(OH)?C Bond Cleavage by a Mn-Doped Cobalt Oxyhydroxide Catalyst
Zhou, Hua,Li, Zhenhua,Xu, Si-Min,Lu, Lilin,Xu, Ming,Ji, Kaiyue,Ge, Ruixiang,Yan, Yifan,Ma, Lina,Kong, Xianggui,Zheng, Lirong,Duan, Haohong
supporting information, p. 8976 - 8982 (2021/03/16)
Oxidative cleavage of C(OH)?C bonds to afford carboxylates is of significant importance for the petrochemical industry and biomass valorization. Here we report an efficient electrochemical strategy for the selective upgrading of lignin derivatives to carboxylates by a manganese-doped cobalt oxyhydroxide (MnCoOOH) catalyst. A wide range of lignin-derived substrates with C(OH)-C or C(O)-C units undergo efficient cleavage to corresponding carboxylates in excellent yields (80–99 %) and operational stability (200 h). Detailed investigations reveal a tandem oxidation mechanism that base from the electrolyte converts secondary alcohols and their derived ketones to reactive nucleophiles, which are oxidized by electrophilic oxygen species on MnCoOOH from water. As proof of concept, this approach was applied to upgrade lignin derivatives with C(OH)-C or C(O)-C motifs, achieving convergent transformation of lignin-derived mixtures to benzoate and KA oil to adipate with 91.5 % and 64.2 % yields, respectively.
