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1. Chromatographic analysis of CBD and THC after their acylation with blockade of compound transformation

Author:
Rafal Typek; Piotr Holowinski; Andrzej L. Dawidowicz; Michal P. Dybowski; Michal Rombel
Source:
Talanta 2023 v.251 pp. 123777
ISSN:
0039-9140
Subject:
acylation; azines; isomerization; temperature
Abstract:
... for the analysis of cannabinoids in bio-matrices are continually improved to achieve best possible sensitivity in their detection and accurate quantification. It has been well documented that CBD cyclizes to Δ9-THC and Δ9-THC isomerizes to Δ8-THC under acidic conditions by means of a Lewis-acid-catalyzed process, causing difficulty in accurate quantification of Δ9-THC in the presence of CBD, of CB ...
DOI:
10.1016/j.talanta.2022.123777

2. (NH₄)₂S₂O₈-Mediated Metal-Free Decarboxylative Formylation/Acylation of α-Oxo/Ketoacids and Its Application to the Synthesis of Indole Alkaloids

Author:
Votarikari Dinesh; Rajagopal Nagarajan
Source:
Journal of organic chemistry 2022 v.87 no.15 pp. 10359-10365
ISSN:
1520-6904
Subject:
acylation; ambient temperature; cross-coupling reactions; organic chemistry
Abstract:
... A metal-free method for the formylation/acylation of indoles and β-carbolines with (NH₄)₂S₂O₈ via direct decarboxylative cross-coupling of α-oxo/ketoacids in moderate to good yields is described. The reaction occurs between ambient temperature and 40 °C under mild reaction conditions with commercially available starting materials. This methodology can be expanded to some biologically active indole ...
DOI:
10.1021/acs.joc.2c00552

3. 13-Epi-9-Deacetylxenicin Derivatives from a Taiwanese Soft Coral Asterospicularia laurae and Treir Cytotoxic Activity

Author:
Zheng-Yu Lin; Kun-Ching Cheng; Huey-Jen Su; Chi-I Chang; Jue-Liang Hsu; Min-fen Hsu; Mei-Chin Lu; Yun-Sheng Lin
Source:
Chemistry of natural compounds 2022 v.58 no.4 pp. 659-668
ISSN:
0009-3130
Subject:
X-ray diffraction; acylation; corals; cytotoxicity; diterpenoids; humans; mass spectrometry; metabolites; neoplasm cells; spectral analysis
Abstract:
... The xenicane-type diterpene 13-epi-9-deacetylxenicin (1) was isolated from polar extract of the soft coral Asterospicularia laurae. The structure of 13-epi-9-deacetylxenicin was determined by X-ray diffraction analysis, and the absoulte configuration was determined using the modified Mosher′s method. Eleven acylation products of 13-epi-9-deacetylxenicin were prepared: 13-epi-9-O-p-anisoylxenicin ( ...
DOI:
10.1007/s10600-022-03765-z

4. Acylating blueberry anthocyanins with fatty acids: Improvement of their lipid solubility and antioxidant activities

Author:
Pengkai Wang; Jingna Liu; Yuanhong Zhuang; Peng Fei
Source:
Food chemistry: X 2022 v.15 pp. 100420
ISSN:
2590-1575
Subject:
Caenorhabditis elegans; acylation; anthocyanins; antioxidants; blueberries; food chemistry; malondialdehyde; myristic acid; solubility
Abstract:
... Aimed at exploring the impact of fatty acid side chains on the anthocyanins, n-valeric acid, n-decanoic acid and myristic acid were used to grafting onto the blueberry anthocyanins, and the acylating degree value of the of n-valeric acid acylated anthocyanins (Va-An), n-decanoic acid acylated anthocyanins (De-An) and myristic acid acylated anthocyanins (My-An) reached 6.43 %, 7.56% and 8.38 %, res ...
DOI:
10.1016/j.fochx.2022.100420

5. Acylation of Anthocyanins and Their Applications in the Food Industry: Mechanisms and Recent Research Advances

Author:
Xiu’er Luo; Ruoyong Wang; Jinhua Wang; Ying Li; Huainan Luo; Shi Chen; Xin’an Zeng; Zhong Han
Source:
Foods 2022 v.11 no.14 pp. -
ISSN:
2304-8158
Subject:
acylation; anthocyanins; biosynthesis; commercialization; food industry; industrial applications; solubility
Abstract:
... Anthocyanins are extensively used as natural non-toxic compounds in the food industry due to their unique biological properties. However, the instability of anthocyanins greatly affects their industrial application. Studies related to acylated anthocyanins with higher stability and increased solubility in organic solvents have shown that the acylation of anthocyanins can improve the stability and ...
DOI:
10.3390/foods11142166

6. Acylation of m-cresol with acetic acid supported by in-situ ester formation on H-ZSM-5 zeolites

Author:
Han K. Chau; Daniel E. Resasco; Phuong Do; Steven P. Crossley
Source:
Journal of catalysis 2022 v.406 pp. 48-55
ISSN:
0021-9517
Subject:
acetates; acetic acid; acetophenones; active sites; acylation; catalysts; catalytic activity; esterification; feedstocks; kinetics; partial pressure; reaction kinetics; solvents; vapors; zeolites
Abstract:
... Friedel-Crafts acylation of phenolic compounds with carboxylic acids catalyzed by Brønsted-acid zeolites is an interesting reaction that could find application in the production of fuels and chemicals from renewable feedstocks. The mechanism of direct acylation of m-cresol with acetic acid over protonic zeolites and the role that the confining environment may have on reaction rate and product sele ...
DOI:
10.1016/j.jcat.2021.12.020

7. Adjusting and visualizing the stability of an acyl chloride through the delocalization effect and introducing AIEgens

Author:
Lu Liu; Qing Wan; Chen Gui; Ping He; Zujin Zhao; Zhiming Wang; Ben Zhong Tang
Source:
Chemical communications 2022 v.58 no.38 pp. 5769-5772
ISSN:
1364-548X
Subject:
acylation; crystallography; fluorescence; imidazole; temperature
Abstract:
... Acyl chloride is an important functional group in acylation reactions, though its compounds are difficult to store and transport due to their high reactivity. In this research, phenanthro[9,10-d]imidazole is introduced into an acyl chloride agent of TPEPCl to enhance the stability via the delocalization effect. Meanwhile, rarely reported acyl chloride crystals have been achieved which could furthe ...
DOI:
10.1039/d2cc00909a

8. Agile Construction of Porous Organic Frameworks Pending Carboxylic Acids and Imidazolium-Based Ionic Liquids for the Efficient Fixation of CO₂ to Cyclic Carbonates

Author:
Yunlong Yang; Yuanlong Guo; Jili Yuan; Haibo Xie; Chengtao Gao; Tianxiang Zhao; Qiang Zheng
Source:
ACS sustainable chemistry & engineering 2022 v.10 no.24 pp. 7990-8001
ISSN:
2168-0485
Subject:
acylation; adsorption; carbon dioxide; carboxylic acids; catalytic activity; composite polymers; density functional theory; energy; epoxides; green chemistry; maleic anhydrides; moieties; porous media; styrene; surface area
Abstract:
... The design and facile preparation of ionic liquids (ILs)-functionalized polymer materials is a hot research topic due to their potential wide applications. Herein, taking the reaction advantage of a cyclic anhydride with an alcoholic compound to atom-economically generate a carboxyl ester pending a carboxylic acid moiety, porous organic framework (POF) materials pending carboxylic acids and imidaz ...
DOI:
10.1021/acssuschemeng.2c01660

9. Alternative Synthesis of Cefamandole with Biocatalytic Acylation Catalyzed by Immobilized Cephalosporin-Acid Synthetase

Author:
A. V. Sklyarenko; I. A. Groshkova; I. N. Krestyanova; S. V. Yarotsky
Source:
Applied biochemistry and microbiology 2022 v.58 no.3 pp. 251-260
ISSN:
0003-6838
Subject:
acylation; biocatalysts; ethylene glycol; mandelic acid; microbiology; pH
Abstract:
... The processes of the biocatalytic acylation of 1-methyl-5-mercapto-1,2,3,4-tetrazolil-7-amino-cephalosporanic acid (7-TMCA) and 7-aminocephalosporanic acid (7-ACA) by methyl ester of mandelic acid (MEMA) were optimized with an immobilized cephalosporin-acid synthetase as the biocatalyst. Under optimized conditions in water-organic medium containing 43% (vol/vol) of ethylene glycol at 30°С with a s ...
DOI:
10.1134/S0003683822030127

10. Anhydride structures affect the acylation modification and emulsion stabilization ability of mammalian and fish gelatins

Author:
Ting Zhang; Jiamin Xu; Shudan Huang; Ningping Tao; Xichang Wang; Jian Zhong
Source:
Food chemistry 2022 v.375 pp. 131882
ISSN:
0308-8146
Subject:
acylation; anhydrides; carbon; cattle; cold-water fish; droplets; emulsifiers; emulsions; fish skin; food chemistry; gelatin; hydrophobicity
Abstract:
... In this work, ring-like anhydrides (C4, C5, and C6) with different sizes and succinic anhydrides (C4, C10, C12, C14, and C16) with different side chain lengths were used to modify bovine bone gelatin (BBG) and cold-water fish skin gelatin (CFG), and the effect of acylated gelatins on fish oil-loaded emulsions stability was explored. The results showed that the degree of N-acylation decreased with ...
DOI:
10.1016/j.foodchem.2021.131882

11. Antimicrobial activity of cyanidin-3-O-glucoside–lauric acid ester against Staphylococcus aureus and Escherichia coli

Author:
Lili Li; Ping Zhou; Yidi Wang; Ying Pan; Min Chen; Ye Tian; Hua Zhou; Baoru Yang; Hecheng Meng; Jie Zheng
Source:
Food chemistry 2022 v.383 pp. 132410
ISSN:
0308-8146
Subject:
Escherichia coli; Staphylococcus aureus; acylation; anthocyanins; antibacterial properties; cell membranes; fatty acids; food chemistry; food preservatives; lipophilicity; minimum inhibitory concentration; pH; solubility
Abstract:
... Enzymatic acylation of anthocyanin with fatty acid improves its lipophilic solubility and application potential. Nevertheless, evaluation of functional properties of product is premise for application. This study investigated the antimicrobial potential and the underlying mechanisms of an acylated anthocyanin, namely, cyanidin-3-O-glucoside–lauric acid ester (C3G-LA), to provide guidelines for its ...
DOI:
10.1016/j.foodchem.2022.132410

12. Calysepins I–VII, Hexasaccharide Resin Glycosides from Calystegia sepium and Their Cytotoxic Evaluation

Author:
Kai-Qing Lv; Hong-Ying Ji; Gao-Xiang Du; Shou Peng; Peng-Ju Guo; Ge Wang; Yao Zhu; Qing Wang; Wen-Qiong Wang; Li-Jiang Xuan
Source:
Journal of natural products 2022 v.85 no.5 pp. 1294-1303
ISSN:
1520-6025
Subject:
Calystegia sepium; acylation; cytotoxicity; glucose; glycosides; rhamnose; spectral analysis
Abstract:
... Seven new hexasaccharide resin glycosides, named calysepins I–VII (1–7), with 27-membered rings, were obtained from the aerial parts of Calystegia sepium. Their structures with absolute configuration were established on the basis of spectroscopic data interpretation analysis and the use of chemical methods. They were defined as hexasaccharides composed of one d-quinovose, four d-glucose, and one l ...
DOI:
10.1021/acs.jnatprod.2c00008

13. Cancer cell metabolism connects epigenetic modifications to transcriptional regulation

Author:
Ashby J. Morrison
Source:
FEBS journal 2022 v.289 no.5 pp. 1302-1314
ISSN:
1742-464X
Subject:
DNA; acylation; cardiovascular diseases; cell death; chromatin; diabetes; energy metabolism; epigenetics; gene expression regulation; genome; histones; metabolites; methylation; neoplasm cells; transcription (genetics)
Abstract:
... Adaptation of cellular function with the nutrient environment is essential for survival. Failure to adapt can lead to cell death and/or disease. Indeed, energy metabolism alterations are a major contributing factor for many pathologies, including cancer, cardiovascular disease, and diabetes. In particular, a primary characteristic of cancer cells is altered metabolism that promotes survival and pr ...
DOI:
10.1111/febs.16032

14. Characterization of the anthocyanin biosynthesis pathway at the metabolic level in the red leaves of Pistacia chinensis

Author:
Xiehai Song; Jin Zhang; Xiaochao Chang; Lihong Xian; Yong Liu
Source:
Scientia horticulturae 2022 v.302 pp. 111158
ISSN:
0304-4238
Subject:
Pistacia chinensis; acylation; anthocyanins; autumn; biosynthesis; color; leaves; metabolites; methylation; ornamental value; procyanidins; taxifolin; transcription (genetics); trees
Abstract:
... Pistacia chinensis is a tree species with colorful leaves and great ornamental value. The molecular mechanism of its anthocyanin biosynthesis has been described from the transcriptional level. However, the type of anthocyanin cannot be obtained from the transcription level, which leads to the ambiguity of anthocyanin biosynthesis pathway. In this study, the pathway of anthocyanin biosynthesis was ...
DOI:
10.1016/j.scienta.2022.111158

15. Chemical modification of clay nanocomposites for the improvement of the catalytic properties of Lipase A from Candida antarctica

Author:
Antônio Luthierre Gama Cavalcante; Anderson Valério Chaves; Pierre Basílio Almeida Fechine; Jeferson Yves Nunes Holanda Alexandre; Tiago Melo Freire; Dalila Maria Barbosa Davi; Francisco Simão Neto; Isamayra Germano de Sousa; Katerine da Silva Moreira; André Luiz Barros de Oliveira; Marcos Carlos de Mattos; Maria Conceição Ferreira Oliveira; Maria Vieira de Brito; Stéphanie Ballereau; Vania Bernardes-Génisson; Aluísio Marques da Fonseca; José C.S. dos Santos
Source:
Process biochemistry 2022 v.120 pp. 1-14
ISSN:
1359-5113
Subject:
Fourier transform infrared spectroscopy; Pseudozyma antarctica; acylation; aluminum; bioavailability; biocatalysts; carboxylic ester hydrolases; carboxymethylcellulose; clay; electron microscopy; enantioselectivity; glutaraldehyde; half life; kaolin; ligands; nanocomposites; polyethyleneimine; surface area; temperature; thermogravimetry
Abstract:
... Kaolin is a mineral composed of hydrated aluminum silicates, clayey and with high bioavailability. The choice of this mineral as immobilization matrix took into account these aspects mentioned above and its high surface area conducive to enzymatic immobilization, containing many OH⁻ binding groups on its surface. Subsequently, the kaolin was functionalized with carboxymethylcellulose and polyethyl ...
DOI:
10.1016/j.procbio.2022.05.020

16. Comparative coexpression networks pinpoint acyltransferases decorating structures of major iridoid glycosides in a medicinal herb, Picrorhiza kurroa

Author:
Ashish Sharma; Shilpa Sharma; Hemant Sood; Rajinder Singh Chauhan
Source:
Plant gene 2022 v.31 pp. 100366
ISSN:
2352-4073
Subject:
1,3-beta-glucan synthase; Picrorhiza kurrooa; acylation; acyltransferases; biosynthesis; catalpol; catechol oxidase; genes; medicinal plants; serine; stolons; transcriptome
Abstract:
... Picrorhiza kurroa, a hepatoprotective Himalayan medicinal herb contains a variety of iridoid glycosides mainly present in stolons and roots, contributing to several medicinal properties. However, off late the herb has been declared as endangered, therefore, warranting alternate production routes for those iridoid glycosides. Catalpol, the major intermediary compound, is transformed into several ir ...
DOI:
10.1016/j.plgene.2022.100366

17. Crystalline lamellar films with honeycomb structure from comb-like polymers of poly(2-long-alkyl-2-oxazoline)s

Author:
Wen-Li Wang; Kousuke Kawai; Hiroaki Sigemitsu; Ren-Hua Jin
Source:
Journal of colloid and interface science 2022 v.627 pp. 28-39
ISSN:
0021-9797
Subject:
acylation; chloroform; composite polymers; films (materials); humidity; polyethyleneimine
Abstract:
... Comb-like copolymers are usually structured by grafting polymeric side chains onto main polymer chain. There are few reports of comb-on-comb polymers in which dense secondary side chains are grafted onto primary side chain. In this work, we synthesized comb polymers with grafted-on-graft side chains (c-PEI-g-Acyl) via an effective acylation reaction of comb polymers possessing polyethyleneimine (P ...
DOI:
10.1016/j.jcis.2022.07.041

18. A De Novo Route to 3,6-Dideoxy Sugars

Author:
Sheng Yang; Chun-Jui Chu; Todd L. Lowary
Source:
Organic letters 2022 v.24 no.30 pp. 5614-5618
ISSN:
1523-7052
Subject:
acylation; glycosides; stereoselective synthesis
Abstract:
... We report the de novo asymmetric synthesis of the 3,6-dideoxy sugars abequose, paratose, and tyvelose from 2-acetylfuran. Conversion of this readily available ketone to a pyranone derivative was followed by transformation to either an α- or β-glycoside via diasteroselective acylation. Michael addition at C2 controlled primarily by the C1 configuration in the glycoside produced 3,6-dideoxy-4-keto s ...
DOI:
10.1021/acs.orglett.2c02349

19. Design of 2,5-furandicarboxylic based polyesters degraded in different environmental conditions: Comprehensive experimental and theoretical study

Author:
Han Hu; Jiayi Li; Shenggan Luo; Ying Tian; Jinggang Wang; Yi-Lei Zhao; Ruoyu Zhang; Jin Zhu
Source:
Journal of hazardous materials 2022 v.425 pp. 127752
ISSN:
0304-3894
Subject:
Pseudozyma antarctica; acylation; adipic acid; biodegradability; carboxylic ester hydrolases; energy; hydrolysis; hydrophilicity; hydrophobicity; polyesters; seawater; succinic acid
Abstract:
... Nowadays, the promotion and application of aliphatic-aromatic copolyesters, such as poly (butylene adipate–co–terephthalate) (PBAT), are growing into a general trend. Although the structures of diacids exerted substantial impacts on degradation behavior, the underlying mechanisms have rarely been studied. In this work, 2,5-Furandicarboxylic acid was combined with succinic acid (PBSF), adipic acid ...
DOI:
10.1016/j.jhazmat.2021.127752

20. Diacylphloroglucinol derivatives as antioxidant agents: green synthesis, optimisation, in vitro, and in silico evaluation

Author:
Wahyu E. Prasetyo; Triana Kusumaningsih; Maulidan Firdaus; Soerya D. Marliana; Venty Suryanti; Anif N. Artanti; Ita Apriana; Septin D. Anggraini
Source:
Natural product research 2022 v.36 no.6 pp. 1460-1466
ISSN:
1478-6427
Subject:
acylation; antioxidant activity; antioxidants; catalysts; computer simulation; density functional theory; energy efficiency; research; response surface methodology; ultrasonic treatment
Abstract:
... Several derivatives of diacylphloroglucinol (3a–3c and 5a–5b) as an analogue of natural product compound 2,4-diacetylphloroglucinol 3a, were successfully synthesised in an excellent yield via a greener Friedel–Craft acylation using methanesulfonic acid (MSA) as a catalyst under an ultrasound-assisted condition. Operational simplicity, excellent yield, expedient metal-free synthesis, energy-efficie ...
DOI:
10.1080/14786419.2021.1889542