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Keywords = isobenzofuranone

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24 pages, 3208 KB  
Article
Antidepressant-Like Effects of n-Butylidenephthalide Using In Vivo and In Silico Approaches
by María Leonor González-Rivera, María del Carmen Juárez-Vázquez, Athzirys Alejandra Melecio-Hernández, Diana Casique-Aguirre, Gabriela Josefina López-González, Ramsés Maximiliano Ramírez-Martínez, Andrea Ayala-Torres, Yurisleidys Quesada-Mendiola, Juan Ramón Zapata-Morales and Angel Josabad Alonso-Castro
Pharmaceuticals 2026, 19(2), 242; https://doi.org/10.3390/ph19020242 - 30 Jan 2026
Viewed by 1258
Abstract
Background: The plant-derived compound n-butylidenephthalide (BP) is an isobenzofuranone that has shown neuropharmacological effects on preclinical models of Parkinson’s, Alzheimer’s, and amyotrophic lateral sclerosis. Methods: This study evaluated the anti-inflammatory, antinociceptive, anxiolytic-like, hypnotic, anticonvulsant, and antidepressant-like effects of BP (50–200 mg/kg p.o.) [...] Read more.
Background: The plant-derived compound n-butylidenephthalide (BP) is an isobenzofuranone that has shown neuropharmacological effects on preclinical models of Parkinson’s, Alzheimer’s, and amyotrophic lateral sclerosis. Methods: This study evaluated the anti-inflammatory, antinociceptive, anxiolytic-like, hypnotic, anticonvulsant, and antidepressant-like effects of BP (50–200 mg/kg p.o.) using Balb/c mice in acute assays. This study also evaluated the antidepressant-like effects of BP in a mouse model of reserpine-induced depression-like behavior for 20 days. Inhibitors involved in the molecular process of depression and in silico studies were used to evaluate a possible mechanism of action for the antidepressant-like effects of BP. Results: BP induced low anti-inflammatory effects, showed low anticonvulsant effects, and lacked hypnotic effects or motor impairment in acute assays. The antidepressant-like effects of BP (100–200 mg/kg p.o.) were comparable to amitriptyline (25 mg/kg p.o.) in acute assays. The participation of serotonergic and adrenergic systems is involved in the acute antidepressant-like effects of BP. In the reserpine-induced depression model, BP (100 mg/kg p.o.) showed antidepressant-like effects in one of the two antidepressant tests, but with a lower effect than amitriptyline (20 mg/kg p.o.). Conclusions: BP (100 and 200 mg/kg) showed antidepressant-like effects in acute assays and, to a lesser extent, in a reserpine-induced chronic model of depression-like behavior. Full article
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14 pages, 6599 KB  
Article
The Influence of Beverages on Resin Composites: An In Vitro Study
by Irina Gradinaru, Ana Lavinia Vasiliu, Alexandra Bargan, Laura Elisabeta Checherita, Bianca-Iulia Ciubotaru, Adina Oana Armencia, Bogdan Istrate, Cristina Gena Dascalu and Magda Ecaterina Antohe
Biomedicines 2023, 11(9), 2571; https://doi.org/10.3390/biomedicines11092571 - 19 Sep 2023
Cited by 9 | Viewed by 2890
Abstract
Dental composites, through their structural diversity, represent the biomaterials frequently used in dental reconstructive therapy. The aim of our study was to observe the influence of different beverage environment conditions on seven types of obturation dental materials with different compositions. Our research focused [...] Read more.
Dental composites, through their structural diversity, represent the biomaterials frequently used in dental reconstructive therapy. The aim of our study was to observe the influence of different beverage environment conditions on seven types of obturation dental materials with different compositions. Our research focused on the surface modification analysis of the materials after the immersion in the different beverages; in this regard, we used the EDAX technique correlated with the energy-dispersive X-ray fluorescence (XRF). The pH of the drinks and that of the simulated saliva solution were determined by the titrimetric method, a sodium hydroxide solution 0.1 mol/dm3 was prepared and used for the titration. An amount of 5 mL of each analyzed solution was added to 15 mL of distilled water to obtain a dilution, to which 3 drops of phenolphthalein (as a color indicator—Phenolphthalein, 3,3-Bis(4-hydroxyphenyl)-1(3H)-isobenzofuranone, C20H14O4 Mw: 318.32, purchased from Merck) were added for each analysis. For each solution, the experiment was repeated three times in order to obtain accurate results. The results of our study materialized into a real plea for modifying the patients’ behavior in terms of diet and preferences for acidic drinks, so that their quality-of-life valence can be improved by keeping the composite materials in a long-term unalterable state on the one hand; on the other hand, systemic damage can be prevented as well. Full article
(This article belongs to the Section Biomedical Engineering and Materials)
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10 pages, 1325 KB  
Communication
DPPH Radical Scavenging Activity of New Phenolics from the Fermentation Broth of Mushroom Morehella importuna
by Feifei Wang, Jie Tan, Ruixiang Jiang, Feifei Li, Renqing Zheng, Linjun Yu, Lianzhong Luo and Yongbiao Zheng
Molecules 2023, 28(12), 4760; https://doi.org/10.3390/molecules28124760 - 14 Jun 2023
Cited by 14 | Viewed by 4144
Abstract
In recent years, wild morel mushroom species have begun to be widely cultivated in China due to their high edible and medicinal values. To parse the medicinal ingredients, we employed the technique of liquid-submerged fermentation to investigate the secondary metabolites of Morehella importuna [...] Read more.
In recent years, wild morel mushroom species have begun to be widely cultivated in China due to their high edible and medicinal values. To parse the medicinal ingredients, we employed the technique of liquid-submerged fermentation to investigate the secondary metabolites of Morehella importuna. Two new natural isobenzofuranone derivatives (12) and one new orsellinaldehyde derivative (3), together with seven known compounds, including one o-orsellinaldehyde (4), phenylacetic acid (5), benzoic acid (6), 4-hydroxy-phenylacetic acid (7), 3,5-dihydroxybenzoic acid (8), N,N′-pentane-1,5-diyldiacetamide (9), and 1H-pyrrole-2-carboxylic acid (10), were obtained from the fermented broth of M. importuna. Their structures were determined according to the data of NMR, HR Q-TOF MS, IR, UV, optical activity, and single-crystal X-ray crystallography. TLC-bioautography displayed that these compounds possess significant antioxidant activity with the half DPPH free radical scavenging concentration of 1.79 (1), 4.10 (2), 4.28 (4), 2.45 (5), 4.40 (7), 1.73 (8), and 6.00 (10) mM. The experimental results would shed light on the medicinal value of M. importuna for its abundant antioxidants. Full article
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20 pages, 1510 KB  
Article
Acid/Base-Steered Cascade Cyclization: An Efficient One-Pot Access to Diverse Isobenzofuranone and Isoindolobenzoxazinone Derivatives
by Ran Shi, Xiangmin Wang, Xuesi Zhang, Sen Chen, Zu-Li Wang, Huijing Qi and Xin-Ming Xu
Molecules 2023, 28(3), 1443; https://doi.org/10.3390/molecules28031443 - 2 Feb 2023
Cited by 4 | Viewed by 4185
Abstract
We herein report the acid/base-steered two distinct reaction pathways of 2-acylbenzoic acids with isatoic anhydrides. In the presence of Na2CO3, the cascade process consists of the cyclization of 2-acetylbenzoic acid and nucleophilic ring-opening reaction of isatoic anhydride to furnish [...] Read more.
We herein report the acid/base-steered two distinct reaction pathways of 2-acylbenzoic acids with isatoic anhydrides. In the presence of Na2CO3, the cascade process consists of the cyclization of 2-acetylbenzoic acid and nucleophilic ring-opening reaction of isatoic anhydride to furnish isobenzofuranone derivatives with high efficiency. However, p-toluenesulfonic acid can promote the product isobenzofuranones to undergo sequential intramolecular rearrangment, nucleophilic addition and cyclization reaction to produce diverse isoindolobenzoxazinones in good yields. The synthetic utility of this method was further demonstrated by the gram-scale preparation of the desired products and the facile transformations of the resulting products. Full article
(This article belongs to the Special Issue Novel Organic Synthetic Route to Heterocyclic Compounds)
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20 pages, 1687 KB  
Article
Antiparasitic Meroterpenoids Isolated from Memnoniella dichroa CF-080171
by Frederick Boye Annang, Guiomar Pérez-Moreno, Cristina Bosch-Navarrete, Victor González-Menéndez, Jesús Martín, Thomas A. Mackenzie, Maria C. Ramos, Luis M. Ruiz-Pérez, Olga Genilloud, Dolores González-Pacanowska, Francisca Vicente and Fernando Reyes
Pharmaceutics 2023, 15(2), 492; https://doi.org/10.3390/pharmaceutics15020492 - 2 Feb 2023
Cited by 1 | Viewed by 3413
Abstract
Memnoniella is a fungal genus from which a wide range of diverse biologically active compounds have been isolated. A Memnoniella dichroa CF-080171 extract was identified to exhibit potent activity against Plasmodium falciparum 3D7 and Trypanosoma cruzi Tulahuen whole parasites in a high-throughput screening [...] Read more.
Memnoniella is a fungal genus from which a wide range of diverse biologically active compounds have been isolated. A Memnoniella dichroa CF-080171 extract was identified to exhibit potent activity against Plasmodium falciparum 3D7 and Trypanosoma cruzi Tulahuen whole parasites in a high-throughput screening (HTS) campaign of microbial extracts from the Fundación MEDINA’s collection. Bioassay-guided isolation of the active metabolites from this extract afforded eight new meroterpenoids of varying potencies, namely, memnobotrins C-E (13), a glycosylated isobenzofuranone (4), a tricyclic isobenzofuranone (5), a tetracyclic benzopyrane (6), a tetracyclic isobenzofuranone (7), and a pentacyclic isobenzofuranone (8). The structures of the isolated compounds were established by (+)-ESI-TOF high-resolution mass spectrometry and nuclear magnetic resonance spectroscopy. Compounds 1, 2, and 4 exhibited potent antiparasitic activity against P. falciparum 3D7 (EC50 0.04–0.243 μM) and T. cruzi Tulahuen (EC50 0.266–1.37 μM) parasites, as well as cytotoxic activity against HepG2 tumoral liver cells (EC50 1.20–4.84 μM). The remaining compounds (3, 58) showed moderate or no activity against the above-mentioned parasites and cells. Full article
(This article belongs to the Section Drug Targeting and Design)
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9 pages, 2000 KB  
Short Note
3-Amino-4-(diphenylamino)-1H-2-benzopyran-1-one
by Felipe Quiroga-Suavita, Ricaurte Rodríguez and Omar León
Molbank 2022, 2022(3), M1408; https://doi.org/10.3390/M1408 - 14 Jul 2022
Viewed by 2701
Abstract
Various synthetic methodologies to obtain 3,4-diaminoisocumarin nucleus have been reported and described. However, mechanistic analysis based on experimental evidence is lacking. Herein, we report the synthesis of the novel 3-amino-4-(diphenylamino)-1H-2-benzopyran-1-one using a two-step methodology with a new mechanistic proposal to explain [...] Read more.
Various synthetic methodologies to obtain 3,4-diaminoisocumarin nucleus have been reported and described. However, mechanistic analysis based on experimental evidence is lacking. Herein, we report the synthesis of the novel 3-amino-4-(diphenylamino)-1H-2-benzopyran-1-one using a two-step methodology with a new mechanistic proposal to explain the formation of the latter based on previously reported precursors and the established conditions. This compound was afforded in 80% yield. Full article
(This article belongs to the Collection Heterocycle Reactions)
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7 pages, 2059 KB  
Communication
Unexpected Formation of 4-[(1-Carbamoyl-3-oxo-1,3-dihydro-2-benzofuran-1-yl)amino]benzoic Acid from 4-[(3-Amino-1-oxo-1H-2-benzopyran-4-yl)amino]benzoic Acid
by Ricaurte Rodríguez, Felipe Quiroga-Suavita and Mónica Yadira Dotor Robayo
Molbank 2022, 2022(3), M1407; https://doi.org/10.3390/M1407 - 12 Jul 2022
Viewed by 3302
Abstract
With the aim of obtaining derivatives belonging to 2′,3′-diphenyl-3H-spiro[[2]benzofuran-1,4′-imidazole]-3,5′(3′H)-dione nucleus, we synthesized 4-[(3-amino-1-oxo-1H-2-benzopyran-4-yl)amino]benzoic acid (a 3,4-diaminoisocoumarine derivative), a known precursor of 4-[(1-carbamoyl-3-oxo-1,3-dihydro-2-benzofuran-1-yl)amino]benzoic acid (a phthalide–carboxamide-bearing system) by a novel methodology that we report here. The reaction conditions [...] Read more.
With the aim of obtaining derivatives belonging to 2′,3′-diphenyl-3H-spiro[[2]benzofuran-1,4′-imidazole]-3,5′(3′H)-dione nucleus, we synthesized 4-[(3-amino-1-oxo-1H-2-benzopyran-4-yl)amino]benzoic acid (a 3,4-diaminoisocoumarine derivative), a known precursor of 4-[(1-carbamoyl-3-oxo-1,3-dihydro-2-benzofuran-1-yl)amino]benzoic acid (a phthalide–carboxamide-bearing system) by a novel methodology that we report here. The reaction conditions were optimized to afford the latter in 62% yield. Full article
(This article belongs to the Collection Heterocycle Reactions)
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5 pages, 989 KB  
Short Note
N-{2-[(3-Oxo-1,3-dihydro-2-benzofuran-1-yl)acetyl]phenyl}acetamide
by Ricaurte Rodríguez, Omar León, Felipe Quiroga and Jonnathan Cifuentes
Molbank 2021, 2021(3), M1244; https://doi.org/10.3390/M1244 - 2 Jul 2021
Viewed by 4132
Abstract
With the aim of obtaining different derivatives belonging to the isoindolo[2,1-a]quinoline family, we have synthesized a novel N-{2-[(3-oxo-1,3-dihydro-2-benzofuran-1-yl)acetyl]phenyl}acetamide derivative by a Claisen–Smichdt-type condensation reaction in 75% yield. Full article
(This article belongs to the Collection Molecules from Side Reactions)
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4 pages, 501 KB  
Short Note
Dimethyl 2-(1-Methyl-3-oxo-1,3-dihydroisobenzofuran-1-yl)malonate
by Antonia Di Mola, Rosanna Filosa and Antonio Massa
Molbank 2020, 2020(2), M1124; https://doi.org/10.3390/M1124 - 6 Apr 2020
Cited by 1 | Viewed by 3629
Abstract
In this work we report a facile access to a 3,3-disubstituted isobenzofuranone by tandem addition/cyclization reaction to methyl 2-acetylbenzoate in the presence of dimethyl malonate, under basic conditions. Full article
(This article belongs to the Collection Molecules from Catalytic Processes)
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12 pages, 1405 KB  
Article
Microbial Kinetic Resolution of Aroma Compounds Using Solid-State Fermentation
by Filip Boratyński, Ewa Szczepańska, Aleksandra Grudniewska and Teresa Olejniczak
Catalysts 2018, 8(1), 28; https://doi.org/10.3390/catal8010028 - 16 Jan 2018
Cited by 22 | Viewed by 7160
Abstract
A novel microbial approach to the production of enantiomerically enriched and pure aroma compounds based on kinetic resolution via solid-state fermentation is proposed. Twenty-five filamentous fungi were screened for lipase activity and enantioselective hydrolysis of a volatile racemic ester (1-phenylethyl acetate (1 [...] Read more.
A novel microbial approach to the production of enantiomerically enriched and pure aroma compounds based on kinetic resolution via solid-state fermentation is proposed. Twenty-five filamentous fungi were screened for lipase activity and enantioselective hydrolysis of a volatile racemic ester (1-phenylethyl acetate (1)) and several racemic lactones (trans and cis whisky lactones (4, 5), γ-decalactone (7), δ-decalactone (8), (cis-3a,4,7,7a-tetrahydro-1(3H)-isobenzofuranone) (9)). Solid-state fermentation was conducted with linseed and rapeseed cakes. Kinetic resolution afforded enantiomerically enriched products with high enantiomeric excesses (ee = 82–99%). The results highlight the potential economic value of solid-state fermentation using agroindustrial side-stream feedstocks as an alternative to more expensive processes conducted in submerged fermentation. Full article
(This article belongs to the Special Issue Enzyme-Mediated Stereoselective Synthesis)
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13 pages, 1547 KB  
Article
Isobenzofuranones and Isochromenones from the Deep-Sea Derived Fungus Leptosphaeria sp. SCSIO 41005
by Xiaowei Luo, Xiuping Lin, Limbadri Salendra, Xiaoyan Pang, Yu Dai, Bin Yang, Juan Liu, Junfeng Wang, Xuefeng Zhou and Yonghong Liu
Mar. Drugs 2017, 15(7), 204; https://doi.org/10.3390/md15070204 - 29 Jun 2017
Cited by 29 | Viewed by 5667
Abstract
Four new isobenzofuranones, leptosphaerins J–M (14), including an unusual naturally-occurring centrosymmetric dimer skeleton (1), and two new isochromenones, clearanols I–J (910), were obtained from a culture of a deep-sea sediment-derived fungus Leptosphaeria sp. [...] Read more.
Four new isobenzofuranones, leptosphaerins J–M (14), including an unusual naturally-occurring centrosymmetric dimer skeleton (1), and two new isochromenones, clearanols I–J (910), were obtained from a culture of a deep-sea sediment-derived fungus Leptosphaeria sp. SCSIO 41005, together with four known isobenzofuranones (58) and six known isochromenones (1116). These structures were elucidated by extensive spectroscopic analyses, and absolute configurations were assigned on the basis of electronic circular dichroism and optical rotations data comparison. Additionally, the absolute configurations of the new compounds 1 and 9, together with the known one 7 with stereochemistry undetermined, were further confirmed by single crystal X-ray diffraction experiments. A plausible biosynthetic pathway of these isobenzofuranones and isochromenones was also proposed. Full article
(This article belongs to the Special Issue Marine Secondary Metabolite II, 2017)
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7 pages, 941 KB  
Communication
Two New Metabolites from the Endophytic Fungus Alternaria sp. A744 Derived from Morinda officinalis
by Ying Wang, Hong-Xin Liu, Yu-Chan Chen, Zhang-Hua Sun, Hao-Hua Li, Sai-Ni Li, Ming-Li Yan and Wei-Min Zhang
Molecules 2017, 22(5), 765; https://doi.org/10.3390/molecules22050765 - 8 May 2017
Cited by 34 | Viewed by 5295
Abstract
Two new compounds isobenzofuranone A (1) and indandione B (2), together with eleven known compounds (313) were isolated from liquid cultures of an endophytic fungus Alternaria sp., which was obtained from the medicinal plant Morinda [...] Read more.
Two new compounds isobenzofuranone A (1) and indandione B (2), together with eleven known compounds (313) were isolated from liquid cultures of an endophytic fungus Alternaria sp., which was obtained from the medicinal plant Morinda officinalis. Among them, the indandione (2) showed a rarely occurring indanone skeleton in natural products. Their structures were elucidated mainly on the basis of extensive spectroscopic data analysis. All of the compounds were evaluated with cytotoxic and α-glucosidase inhibitory activity assays. Compounds 11 and 12 showed significant inhibitory activities against four tumor cell lines; MCF-7, HepG-2, NCI-H460 and SF-268, with IC50 values in the range of 1.91–9.67 μM, and compounds 4, 5, 9, 10, 12 and 13 showed excellent inhibitory activities against α-glucosidase with IC50 values in the range of 12.05–166.13 μM. Full article
(This article belongs to the Section Natural Products Chemistry)
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12 pages, 1234 KB  
Article
LC-MS/MS Analysis and Pharmacokinetics of Sodium (±)-5-Bromo-2-(α-hydroxypentyl) Benzoate (BZP), an Innovative Potent Anti-Ischemic Stroke Agent in Rats
by Xin Tian, Bingjie Liu, Yuhai Zhang, Hongmeng Li, Jingyao Wei, Gaoju Wang, Junbiao Chang and Hailing Qiao
Molecules 2016, 21(4), 501; https://doi.org/10.3390/molecules21040501 - 16 Apr 2016
Cited by 12 | Viewed by 6917
Abstract
A rapid, sensitive and selective liquid chromatography-triple quadrupole mass spectrometry (LC-MS/MS) method was developed and validated for the simultaneous determination of sodium (±)-5-Bromo-2-(α-hydroxypentyl) benzoate (BZP) and its active metabolite 3-butyl-6-bromo-1(3H)-isobenzofuranone (Br-NBP) in rat plasma using potassium 2-(1-hydroxypentyl)-benzoate (PHPB) and l-3-n-butylphthalide (NBP) [...] Read more.
A rapid, sensitive and selective liquid chromatography-triple quadrupole mass spectrometry (LC-MS/MS) method was developed and validated for the simultaneous determination of sodium (±)-5-Bromo-2-(α-hydroxypentyl) benzoate (BZP) and its active metabolite 3-butyl-6-bromo-1(3H)-isobenzofuranone (Br-NBP) in rat plasma using potassium 2-(1-hydroxypentyl)-benzoate (PHPB) and l-3-n-butylphthalide (NBP) as internal standards (IS). Chromatographic separation was achieved on a Hypersil GOLD C18 column using a gradient elution of ammonium acetate and methanol at a flow rate of 0.2 mL/min. Good linearity was achieved within the wide concentration range of 5–10,000 ng/mL. The intra-day and inter-day precision was less than 8.71% and the accuracy was within −8.53% and 6.38% in quality control and the lower limit of quantitation samples. BZP and Br-NBP were stable during the analysis and the storage period. The method was successfully applied to pharmacokinetic studies of BZP in Sprague-Dawley rats for the first time. After a single intravenous administration of BZP at the dose of 0.75 mg/kg, the plasma concentration of BZP and Br-NBP declined rapidly and the AUC0-t of BZP was significantly greater in female rats compared to male rats (p < 0.05). The data presented in this study serve as a firm basis for further investigation of BZP in both preclinical and clinical phases. Full article
(This article belongs to the Section Medicinal Chemistry)
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10 pages, 2319 KB  
Article
The Antileishmanial Potential of C-3 Functionalized Isobenzofuranones against Leishmania (Leishmania) Infantum Chagasi
by Wagner Luiz Pereira, Raphael De Souza Vasconcellos, Christiane Mariotini-Moura, Rodrigo Saar Gomes, Rafaela De Cássia Firmino, Adalberto Manoel Da Silva, Abelardo Silva Júnior, Gustavo Costa Bressan, Márcia Rogéria Almeida, Luís Carlos Crocco Afonso, Róbson Ricardo Teixeira and Juliana Lopes Rangel Fietto
Molecules 2015, 20(12), 22435-22444; https://doi.org/10.3390/molecules201219857 - 14 Dec 2015
Cited by 9 | Viewed by 6061
Abstract
Leishmaniases are diseases caused by protozoan parasites of the genus Leishmania. Clinically, leishmaniases range from cutaneous to visceral forms, with estimated global incidences of 1.2 and 0.4 million cases per year, respectively. The treatment of these diseases relies on multiple parenteral injections [...] Read more.
Leishmaniases are diseases caused by protozoan parasites of the genus Leishmania. Clinically, leishmaniases range from cutaneous to visceral forms, with estimated global incidences of 1.2 and 0.4 million cases per year, respectively. The treatment of these diseases relies on multiple parenteral injections with pentavalent antimonials or amphotericin B. However, these pharmaceuticals are either too toxic or expensive for routine use in developing countries. These facts call for safer, cheaper, and more effective new antileishmanial drugs. In this investigation, we describe the results of the assessment of the activities of a series of isobenzofuran-1(3H)-ones (phtalides) against Leishmania (Leishmania) infantum chagasi, which is the main causative agent of visceral leishmaniasis in the New World. The compounds were tested at concentrations of 100, 75, 50, 25 and 6.25 µM over 24, 48, and 72 h. After 48 h of treatment at the 100 µM concentration, compounds 7 and 8 decreased parasite viability to 4% and 6%, respectively. The concentration that gives half-maximal responses (LC50) for the antileishmanial activities of compounds 7 and 8 against promastigotes after 24 h were 60.48 and 65.93 µM, respectively. Additionally, compounds 7 and 8 significantly reduced parasite infection in macrophages. Full article
(This article belongs to the Section Medicinal Chemistry)
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17 pages, 216 KB  
Article
Microbial Stereoselective One-Step Conversion of Diols to Chiral Lactones in Yeast Cultures
by Filip Boratyński, Ewa Szczepańska, Jakub Pannek and Teresa Olejniczak
Catalysts 2015, 5(4), 2068-2084; https://doi.org/10.3390/catal5042068 - 8 Dec 2015
Cited by 3 | Viewed by 6157
Abstract
It has been shown that whole cells of different strains of yeast catalyze stereoselective oxidation of meso diols to the corresponding chiral lactones. Among screening-scale experiments, Candida pelliculosa ZP22 was selected as the most effective biocatalyst for the oxidation of monocyclic diols 3a–b [...] Read more.
It has been shown that whole cells of different strains of yeast catalyze stereoselective oxidation of meso diols to the corresponding chiral lactones. Among screening-scale experiments, Candida pelliculosa ZP22 was selected as the most effective biocatalyst for the oxidation of monocyclic diols 3a–b with respect to the ratio of high conversion to stereoselectivity. This strain was used in the preparative oxidation, affording enantiomerically-enriched isomers of lactones: (+)-(3aR,7aS)-cis-hexahydro-1(3H) -isobenzofuranone (2a) and (+)-(3aS,4,7,7aR)-cis-tetrahydro-1(3H)-isobenzofuranone (2b). Scaling up the culture growth, as well as biotransformation conditions has been successfully accomplished. Among more bulky substrates, bicyclic diol 3d was totally converted into enantiomerically-pure exo-bridged (+)-(3aR,4S,7R,7aS)-cis-tetrahydro-4,7-methanoisobenzofuran -1(3H)-one (2d) by Yarrovia lipolytica AR71. Microbial oxidation of diol 3f by Candida sake AM908 and Rhodotorula rubra AM4 afforded optically-pure cis-3-butylhexahydro-1(3H) -isobenzofuranone (2f), however with low conversion. Full article
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