Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis and Biotransformation of Bicyclic Unsaturated Lactones with Three or Four Methyl Groups.

ABSTRACT: The aim of this study was to obtain new unsaturated lactones by chemical synthesis and their microbial transformations using fungal strains. Some of these strains were able to transform unsaturated lactones into different hydroxy or epoxy derivatives. Strains of Syncephalastrum racemosum and Absidia cylindrospora gave products with a hydroxy group introduced into a tertiary carbon, while the Penicillium vermiculatum strain hydroxylated primary carbons. The Syncephalastrum racemosum strain hydroxylated both substrates in an allylic position. Using the Absidia cylindrospora and Penicillium vermiculatum strains led to the obtained epoxylactones. The structures of all lactones were established on the basis of spectroscopic data.

SUBMITTER: Winska K

PROVIDER: S-EPMC6155629 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis and Biotransformation of Bicyclic Unsaturated Lactones with Three or Four Methyl Groups.

Wińska Katarzyna K Grabarczyk Małgorzata M Mączka Wanda W Kondas Adrianna A Maciejewska Gabriela G Bonikowski Radosław R Anioł Mirosław M

Molecules (Basel, Switzerland) 20170117 1

The aim of this study was to obtain new unsaturated lactones by chemical synthesis and their microbial transformations using fungal strains. Some of these strains were able to transform unsaturated lactones into different hydroxy or epoxy derivatives. Strains of Syncephalastrum racemosum and Absidia cylindrospora gave products with a hydroxy group introduced into a tertiary carbon, while the Penicillium vermiculatum strain hydroxylated primary carbons. The Syncephalastrum ...[more]

PMID: 28106750

Similar Datasets

Rapid synthesis of bicyclic lactones via palladium-catalyzed aminocarbonylative lactonizations.

Project description:A novel and efficient palladium-catalyzed aminocarbonylative lactonization of amino propargylic alcohols has been developed to provide rapid access to various bicyclic lactones especially dihydropyrrole-fused furanones, which are novel structures and have not been explored in biological and medicinal settings. This method can also be used to access β-lactone products such as 16. Preliminary biological evaluations revealed that compounds 13h and 13s demonstrated promising activity against Clostridium difficile and compounds 13h, 13k, 13s, and 16b showed activity against several important fungal pathogens.

| S-EPMC8279068 | biostudies-literature

Lactones 41. Synthesis and microbial hydroxylation of unsaturated terpenoid lactones with p-menthane ring systems.

Project description:Racemic [(±)-4-isopropyl-1-methyl-7-oxa-cis-bicyclo[4.3.0]non-4-en-8-one] and optically active δ,ε-unsaturated lactones [(-)-(1R,6R)-4-isopropyl-1-methyl-7-oxabicyclo[4.3.0]non-4-en-8-one and (+)-(1S,6S)-4-isopropyl-1-methyl-7-oxabicyclo[4.3.0] non-4-en-8-one)] with the p-menthane system were obtained and their odoriferous properties were evaluated. Biotransformations of the racemic lactone with three fungal strains: Absidia cylindrospora AM336, Absidia glauca AM177 and Syncephalastrum racemosum AM105, were carried out. Microbial transformations afforded hydroxylactones with the hydroxy group in the allylic position.

| S-EPMC6269982 | biostudies-literature

Substrate encapsulation: an efficient strategy for the RCM synthesis of unsaturated epsilon-lactones.

Project description:A facile substrate-encapsulated RCM-based synthesis of 7-membered lactones is reported. Coordination of the alpha,omega-dienyl ester precursor to the bulky Lewis acid (LA) aluminum tris(2,6-diphenylphenoxide) (ATPH) provides a protective extended steric pocket to the olefin moieties, thereby favoring intramolecular RCM over intermolecular ADMET oligomerization. The LA-encapsulated esters undergo ring-closure in the presence of Ru-based olefin metathesis catalysts to give previously difficult-to-access 7-membered beta,gamma- and gamma,delta-unsaturated lactones in good yields.

| S-EPMC3083066 | biostudies-literature

Asymmetric Synthesis of [2.2.2]-Bicyclic Lactones via All-Carbon Inverse-Electron-Demand Diels-Alder Reaction.

Project description:In this paper, a new cycloaddition between α,β-unsaturated aldehydes and coumalates realized under dienamine activation has been described. The reaction proceeds regioselectively with the distal double bond of the dienamine system acting as electron-rich dienophile. It leads to the formation of biologically relevant [2.2.2]-bicyclic lactones. Their functionalization potential has been confirmed in selected, diastereoselective transformations.

| S-EPMC7497662 | biostudies-literature

Biotransformation of Bicyclic Halolactones with a Methyl Group in the Cyclohexane Ring into Hydroxylactones and Their Biological Activity.

Project description:The aim of this study was the chemical synthesis of a series of halo- and unsaturated lactones, as well as their microbial transformation products. Finally some of their biological activities were assessed. Three bicyclic halolactones with a methyl group in the cyclohexane ring were obtained from the corresponding ?,?-unsaturated ester during a two-step synthesis. These lactones were subjected to screening biotransformation using twenty two fungal strains. These strains were tested on their ability to transform halolactones into new hydroxylactones. Among the six strains able to catalyze hydrolytic dehalogenation, only two (Fusarium equiseti, AM22 and Yarrowia lipolytica, AM71) gave a product in a high yield. Moreover, one strain (Penicillium wermiculatum, AM30) introduced the hydroxy group on the cyclohexane ring without removing the halogen atom. The biological activity of five of the obtained lactones was tested. Some of these compounds exhibited growth inhibition against bacteria, yeasts and fungi and deterrent activity against peach-potato aphid.

| S-EPMC6273801 | biostudies-other

Asymmetric Synthesis of ?-Lactones through Koga Amine-Controlled Addition of Enediolates to ?,?-Unsaturated Sulfoxonium Salts.

Project description:A chiral Koga amine-controlled asymmetric synthesis of cis-?-lactones through a formal [3 + 2] cycloaddition of enediolates with ?,?-unsaturated sulfoxonium salts is described. The desired structural motif was formed in moderate to good yields (50-71% for 13 examples), with good to very good diastereoselectivity (dr 5:1 to 10:1 for 20 examples), favoring the cis-isomer, and good to excellent enantioselectivity (70-91% ee for 13 examples).

| S-EPMC5591458 | biostudies-literature

Catalytic Hydroxycyclopropanol Ring-Opening Carbonylative Lactonization to Fused Bicyclic Lactones.

Project description:A novel palladium-catalyzed ring opening carbonylative lactonization of readily available hydroxycyclopropanols was developed to efficiently synthesize tetrahydrofuran (THF) or tetrahydropyran (THP)-fused bicyclic γ-lactones, two privileged scaffolds often found in natural products. The reaction features mild reaction conditions, good functional group tolerability, and scalability. Its application was demonstrated in a short total synthesis of (±)-paeonilide. The fused bicyclic γ-lactone products can be easily diversified to other medicinally important scaffolds, which further broadens the application of this new carbonylation method.

| S-EPMC8232350 | biostudies-literature

Preparation of bicyclic 1,2,4-trioxanes from gamma,delta-unsaturated ketones.

Project description:Treatment of gamma,delta-unsaturated ketones with hydrogen peroxide and acid provides a rapid entry into the medicinally important 1,2,4-trioxane structure. Alkene substitution that stabilizes carbocationic intermediates proved to be important for the success of this transformation.

| S-EPMC2657341 | biostudies-literature

Electrophilic reactivities of cyclic enones and α,β-unsaturated lactones.

Project description:The reactivities of cyclic enones and α,β-unsaturated lactones were characterized by following the kinetics of their reactions with colored carbon-centered reference nucleophiles in DMSO at 20 °C. The experimentally determined second-order rate constants k 2 were analyzed with the Mayr-Patz equation, lg k = s N(N + E), to furnish the electrophilicity descriptors E for the Michael acceptors. Cyclic enones and lactones show different reactivity trends than their acyclic analogs. While cyclization reduces the reactivity of enones slightly, α,β-unsaturated lactones are significantly more reactive Michael acceptors than analogously substituted open-chain esters. The observed reactivity trends were rationalized through quantum-chemically calculated Gibbs energy profiles (at the SMD(DMSO)/M06-2X/6-31+G(d,p) level of theory) and distortion interaction analysis for the reactions of the cyclic Michael acceptors with a sulfonium ylide. The electrophilicities of simplified electrophilic fragments reflect the general reactivity pattern of structurally more complex terpene-derived cyclic enones and sesquiterpene lactones, such as parthenolide.

| S-EPMC8179571 | biostudies-literature

Structural Elucidation of Trace Components Combining GC/MS, GC/IR, DFT-Calculation and Synthesis-Salinilactones, Unprecedented Bicyclic Lactones from Salinispora Bacteria.

Project description:The analysis of volatiles released by marine Salinispora bacteria uncovered a new class of natural compounds displaying an unusual bicyclic [3.1.0]-lactone skeleton. Although only sub-μg quantities of the compounds were available, the combination of analytical methods, computational spectroscopy, and synthesis allowed unambiguous structural identification of the compounds, called salinilactones, without the need for isolation. Orthogonal hyphenated methods, GC/MS and solid-phase GC/IR allowed to propose a small set of structures consistent with the data. A candidate structure was selected by comparison of DFT-calculated IR spectra and the experimental IR-spectrum. Synthesis confirmed the structure and absolute configuration of three bicyclic lactones, salinilactones A-C. The salinilactones are structurally closely related to the A-factor class of compounds, autoregulators from streptomycete bacteria. They exhibited inhibitory activity against Salinispora and Streptomyces strains.

| S-EPMC6243141 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data