7512-17-6Relevant articles and documents
Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives
Cao, Lian-Gong,Cao, Zhi-Ling,Jiang, Kai-Jun,Liu, Shu-Hao,Liu, Wei-Wei,Lu, Xing,Shao, Zhong-Bai,Shi, Da-Hua,Wang, Lei,Wang, You-Xian
, p. 359 - 364 (2020/12/28)
Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.
Synthesis and Anti-Cholinesterase Activity of Novel Glycosyl Benzofuranylthiazole Derivatives
Cao, L.,Cao, Zh.,Chen, Ch.,Jiang, K.,Liu, Sh.,Liu, W.,Lu, X.,Shao, Zh.,Shi, D.,Su, Z.,Wang, L.,Wang, Y.,Wu, Y.
, p. 1513 - 1518 (2021/10/26)
Abstract: A new series of glycosyl benzofuranylthiazole derivatives were designed, synthesized, characterized, and evaluated as potential candidates to treat Alzheimer’s disease. The compounds have been synthesized by the cyclocondensation of glycosyl thiourea with a variety of 2-(bromoacetyl)benzofurans. The reaction conditions have been optimized, and good yields (79–95%) have been obtained. The synthesized compounds showed different degrees of cholinesterase inhibitory activity.
Glycosides and Glycoconjugates of the Diterpenoid Isosteviol with a 1,2,3-Triazolyl Moiety: Synthesis and Cytotoxicity Evaluation
Andreeva, Olga V.,Garifullin, Bulat F.,Sharipova, Radmila R.,Strobykina, Irina Yu.,Sapunova, Anastasiya S.,Voloshina, Alexandra D.,Belenok, Mayya G.,Dobrynin, Alexey B.,Khabibulina, Leysan R.,Kataev, Vladimir E.
, p. 2367 - 2380 (2020/08/28)
Several glycoconjugates of the diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) with a 1,2,3-triazolyl moiety were synthesized, and their cytotoxicity was evaluated against some human cancer and normal cell lines. Most of the synthesized compounds demonstrated weak inhibitory activities against the M-HeLa and MCF-7 human cancer cell lines. Three lead compounds, 54, 56 and 57, exhibited high selective cytotoxic activity against M-HeLa cells (IC50 = 1.7-1.9 μM) that corresponded to the activity of the anticancer drug doxorubicin (IC50 = 3.0 μM). Moreover, the lead compounds were not cytotoxic with respect to a Chang liver human normal cell line (IC50 > 100 μM), whereas doxorubicin was cytotoxic to this cell line (IC50 = 3.0 μM). It was found that cytotoxic activity of the lead compounds is due to induction of apoptosis proceeding along the mitochondrial pathway. The present findings suggest that 1,2,3-triazolyl-ring-containing glycoconjugates of isosteviol are a promising scaffold for the design of novel anticancer agents.
Biochemical Characterization and Structural Analysis of a β- N-Acetylglucosaminidase from Paenibacillus barengoltzii for Efficient Production of N-Acetyl- d -glucosamine
Liu, Yihao,Jiang, Zhengqiang,Ma, Junwen,Ma, Shuai,Yan, Qiaojuan,Yang, Shaoqing
, p. 5648 - 5657 (2020/06/03)
Bioproduction of N-acetyl-d-glucosamine (GlcNAc) from chitin, the second most abundant natural renewable polymer on earth, is of great value in which chitinolytic enzymes play key roles. In this study, a novel glycoside hydrolase family-18 β-N-acetylglucosaminidase (PbNag39) from Paenibacillus barengoltzii suitable for GlcNAc production was identified and biochemically characterized. It possessed a unique shallow catalytic groove (5.8 ?) as well as a smaller C-terminal domain (solvent-accessible surface area, 5.1 × 103 ?2) and exhibited strict substrate specificity toward N-acetyl chitooligosaccharides (COS) with GlcNAc as the sole product, showing a typical manner of action of β-N-acetylglucosaminidases. Thus, an environmentally friendly bioprocess for GlcNAc production from ball-milled powdery chitin by an enzyme cocktail reaction was further developed. By using the new route, the powdery chitin conversion rate increased from 23.3% (v/v) to 75.3% with a final GlcNAc content of 22.6 mg mL-1. The efficient and environmentally friendly bioprocess may have great application potential in GlcNAc production.
Synthesis and anticholinesterase activities of novel glycosyl benzoxazole derivatives
Cao, Zhi-Ling,Liu, Shu-Hao,Liu, Wei-Wei,Ren, Shu-Ting,Shi, Da-Hua,Wang, Lei,Wang, You-Xian,Wu, Yu-Ran
, p. 363 - 366 (2020/02/05)
Eight glycosyl benzoxazole derivatives are synthesized by nucleophilic addition reactions of glycosyl isothiocyanate with o-aminophenol in tetrahydrofuran. The reaction conditions are optimized, and good yields (86%–94%) were obtained. The structures of all new products are confirmed by infrared, 1H nuclear magnetic resonance, and high-resolution mass spectrometry (electrospray ionization). In addition, the in vitro cholinesterase inhibitory activities of these new compounds are tested by Ellman’s method.
Simplified determination of the content and average degree of acetylation of chitin in crude black soldier fly larvae samples
D'Hondt, Els,Soetemans, Lise,Bastiaens, Leen,Maesen, Miranda,Jespers, Vincent,Van den Bosch, Bert,Voorspoels, Stefan,Elst, Kathy
supporting information, (2020/01/25)
Insects are considered a promising alternative protein source for food and feed, but contain significant amounts of chitin, often undesirable due to indigestibility, disagreeable texture and negative effect on nutrients intake. Fractionation strategies are thus increasingly being applied to isolate and valorize chitin separately. The analysis of chitin generally requires an intensive pretreatment to remove impurities, and derivatization to generate sufficient detector response. In this work, a liquid chromatography method, without pretreatment nor derivatization, was developed for the simultaneous determination of chitin content and degree of acetylation in non-purified samples of black soldier fly (BSF) larvae. The method is found to be more suitable, compared to traditional methods, for assessing high degrees of acetylation. For the first time, the degree of acetylation of BSF chitin (81 ± 2%) is reported. Additionally, the chitin content of BSF soft tissues is estimated at approximately 20% of the total chitin content (8.5 ± 0.1%).
N-acetyltransferases from three different organisms displaying distinct selectivity toward hexosamines and N-terminal amine of peptides
Zhang, Peiru,Liu, Pei,Xu, Yangyang,Liang, Yulu,Wang, Peng George,Cheng, Jiansong
, p. 72 - 75 (2018/11/30)
N-acetyltransferases are a family of enzymes that catalyze the transfer of the acetyl moiety (–COCH3) from acetyl coenzyme A (Acetyl-CoA) to a primary amine of acceptor substrates from small molecules such as aminoglycoside to macromolecules of various proteins. In this study, the substrate selectivity of three N-acetyltransferases falling into different phylogenetic groups was probed against a series of hexosamines and synthetic peptides. GlmA from Clostridium acetobutylicum and RmNag from Rhizomucor miehei, which have been defined as glucosamine N-acetyltransferases, were herein demonstrated to be also capable of acetylating the free amino group on the very first glycine residue of peptide in spite of varied catalytic efficiency. The human recombinant N-acetyltransferase of Naa10p, however, prefers primary amine groups in the peptides as opposed to glucosamine. The varied preference of GlmA, RmNag and Naa10p probably arose from the divergent evolution of these N-acetyltransferases. The expanded knowledge of acceptor specificity would as well facilitate the application of these N-acetyltransferases in the acetylation of hexosamines or peptides.
Aromatic butenolides produced by a soil ascomycete Auxarthron sp. KCB15F070 derived from a volcanic island
Kim, Jong Won,Son, Sangkeun,Kim, Gil Soo,Otaka, Junnosuke,Miura, Yuzuki,Muranaka, Atsuya,Uchiyama, Masanobu,Lee, Jung-Sook,Jang, Mina,Ko, Sung-Kyun,Takahashi, Shunji,Osada, Hiroyuki,Jang, Jae-Hyuk,Ahn, Jong Seog
, (2019/10/19)
LC/MS-based chemical screening of fungal extract fraction library led to identification of three 2,3-aryl substituted furanone metabolites (1–3), including one known butenolide glycoside (1) whose stereochemistry remained unsolved and two new compounds gotjawaside and gotjawalide (2 and 3), from Auxarthron sp. KCB15F070, a fungus isolated from a soil sample of the volcanic island Jeju, Korea. Their planar structures were elucidated by 1D- and 2D-NMR spectroscopic and HRESIMS spectrometric techniques, and the absolute configurations of three compounds were solved using a combination of chemical derivatizations and computational analysis of vibrational circular dichroism (VCD) spectra.
Structures of triterpenoids from the leaves of Lansium domesticum
Matsumoto, Takahiro,Kitagawa, Takahiro,Ohta, Tomoe,Yoshida, Tatsusada,Imahori, Daisuke,Teo, Stephen,Ahmad, Haji Sapuan bin,Watanabe, Tetsushi
, p. 727 - 734 (2019/05/29)
From the methanolic extract of the leaves of Lansium domesticum, three new onoceranoid-type triterpenoids, lansium acids X–XII and a new cycloartane-type triterpene, lansium acid XIII, were isolated. The chemical structures of the isolated new compounds were elucidated on the basis of chemical/physicochemical evidence. For new onoceranoid-type triterpenoids, the absolute configurations were established by comparison of experimental and predicted electronic circular dichroism (ECD) data. The isolated onoceranoid-type triterpenoids showed antimutagenic effects in the Ames assay against 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1).
