Biotransformation of Lactones with Methylcyclohexane Ring and Their Biological Activity

Wińska, Katarzyna; Grabarczyk, Małgorzata; Mączka, Wanda; Żarowska, Barbara; Maciejewska, Gabriela; Dancewicz, Katarzyna; Gabryś, Beata; Anioł, Mirosław

doi:10.3390/app7010012

Cited by 7 publications

(9 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The lack of products derived from chlorolactone 4 was, therefore, not surprising. Bromo-and iodolactones are much more frequently transformed by filamentous fungi [19][20][21][22]. Such a dependence can be seen here as well.…”

Section: Preparative Biotransformation Of Halolactones 5 and 6 Analys...supporting

confidence: 70%

“…In our research, we used lactones containing halogen atoms in the molecule of substrates. Previous studies carried out so far showed [18][19][20][21][22][23][24] that filamentous fungi, especially those belonging to the genera Fusarium and Absidia, can carry out the hydrolytic dehalogenation of halolactones. As a result, hydroxylactones with a different conformation than halolactones obtained by chemical synthesis were obtained.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

New Bromo- and Iodo-Hydroxylactones with Two Methyl Groups Obtained by Biotransformation of Bicyclic Halolactones

et al. 2021

Self Cite

View full text Add to dashboard Cite

The subject of the research was to determine the ability of the filamentous fungi to biotransform bicyclic halolactones containing two methyl groups in their structure. By chemical synthesis three bicyclic halolactones with two methyl groups, one in the cyclohexane ring and one in the lactone ring, were obtained: 2-chloro-4,7-dimethyl-9-oxabicyclo[4.3.0]nonan-8-one, 2-bromo-4,7-dimethyl-9-oxabicyclo[4.3.0]nonan-8-one, and 2-iodo-4,7-dimethyl-9-oxabicyclo[4.3.0]nonan-8-one. These compounds were formed as mixtures of two diastereoisomers. The obtained halolactones (as mixture of two diastereoisomers) were subjected to screening biotransformation with the use of eight strains of filamentous fungi: Fusarium culmorum AM10, F. avenaceum AM12, F. semitectum AM20, F. solani AM203, Absidia coerulea AM93, A. cylindrospora AM336, Penicillium chermesinum AM113, P. frequentans AM351. Two of the substrates, 2-bromo-4,7-dimethyl-9-oxabicyclo[4.3.0]nonan-8-one and 2-iodo-4,7-dimethyl-9-oxabicyclo[4.3.0]nonan-8-one, were hydroxylated without removing the halogen atom from the molecule, giving 2-bromo-7-hydroxy-4,7-dimethyl-9-oxabicyclo[4.3.0]nonan-8-one, 2-bromo-5-hydroxy-4,7-dimethyl-9-oxabicyclo[4.3.0]nonan-8-one, and 2-iodo-7-hydroxy-4,7-dimethyl-9-oxabicyclo[4.3.0]nonan-8-one as products. The hydroxylation capacity was demonstrated by strains of Absidia cylindrospora AM336, Fusarium avenaceum AM12, and F. solani AM203. The structures of all lactones were determined on the basis spectroscopic data.

show abstract

Section: Preparative Biotransformation Of Halolactones 5 and 6 Analys...supporting

confidence: 70%

Section: Introductionmentioning

confidence: 99%

New Bromo- and Iodo-Hydroxylactones with Two Methyl Groups Obtained by Biotransformation of Bicyclic Halolactones

et al. 2021

Self Cite

View full text Add to dashboard Cite

show abstract

“…However, lactone compounds' antibacterial activity depends on if the structure contains substituent fluorine and the length of the bacterial lipopolysaccharide (Kowalczyk et al, 2021). As such, unsaturated and hydroxy lactone compounds have antibacterial activity against S. aureus (Wińska et al, 2018). -lactone compounds also show antibacterial activity (Mazur & Maslowiec, 2022).…”

Section: Resultsmentioning

confidence: 99%

Bioactivity of Endophytic Fungi Isolated from Branch of Jambu Mawar (Syzygium jambos (L.) Alston)

Aini

Elfita

Widjajanti

et al. 2023

molekul

View full text Add to dashboard Cite

Endophytic fungi isolated from medicinal plants have high diversity and the secondary metabolites produced have biological activity. Endophytic fungi isolated from medicinal plants have been the subject of many studies on their diversity and biological activity, one of which is jambu mawar (Syzygium jambos (L.) Alston). S. jambos has long been used as a traditional medicine to treat infections caused by pathogenic bacteria in many parts of the world, including South Sumatra. This study purposed to explore the diversity of endophytic fungi isolated from the branches of S. jambos, the antibacterial activity of endophytic fungi extracts, the determination of the structure of the compounds, and the activity of the active compounds of the selected endophytic fungi. Observations of the morphological characteristics of endophytic fungi were macroscopically and microscopically. The endophytic fungal extracts were then tested for antimicrobial activity against test bacteria Staphylococcus aureus, Bacillus subtilis, Salmonella typhi, and Escherichia coli using the Kirby-Bauer paper disk diffusion method. Isolation of pure compounds using a gravity chromatography column, the determination of the structure of the compound is determined based on 1H-NMR, 13C-NMR, HMQC, and HMBC spectroscopy. Four endophytic fungi, code SJC1–4, were isolated from a branch of S. jambos. The results of macroscopic and microscopic morphological characterization showed three genera of Botryosphaeria, Trichothecium, and Aspergillus. The endophytic fungal isolate SJC1 exhibited strong activity against Gram-positive bacteria and moderate activity against Gram-negative bacteria, while SJC2–4 showed moderate activity against the four bacteria. Molecular identification of SJC1 revealed that it was Botryosphaeria mamane. Isolation of SJC1’s pure compound yielded compound 1, which was identified as 5-acetyl-6-hydroxy-3-methyl-2H-pyran-2-one. This compound is thought to have antibacterial properties.

show abstract

“…All lactones, both substrate and biotransformation products, were able to inhibit the growth of the S. aureus strain. Complete inhibition was observed for lactones 90a – c , and lactone 91 ( Figure 13 ) showed a slight inhibition on the growth of this strain together with a significant extension of the adaptive phase (20–36 h) [ 89 ].…”

Section: Biotransformations As a Methods For Obtaining New Lactone De...mentioning

confidence: 99%

Antimicrobial Activity of Lactones

Mazur

Masłowiec

2022

Antibiotics

View full text Add to dashboard Cite

The development of bacterial resistance to antibiotics and the consequent lack of effective therapy is one of the biggest problems in modern medicine. A consequence of these processes is an urgent need to continuously design and develop novel antimicrobial agents. Among the compounds showing antimicrobial potential, lactones are a group to explore. For centuries, their antimicrobial activities have been used in folk medicine. Currently, novel lactone compounds are continuously described in the literature. Some of those structures exhibit high antimicrobial potential and some are an inspiration for design and synthesis of future drugs. This paper describes recent developments on antimicrobial lactones with smaller ring sizes, up to seven membered ε-lactones. Their isolation from natural sources, chemical synthesis, synergistic activity with antibiotics, and effects on quorum sensing are presented herein.

show abstract

Biotransformation of Lactones with Methylcyclohexane Ring and Their Biological Activity

Cited by 7 publications

References 34 publications

New Bromo- and Iodo-Hydroxylactones with Two Methyl Groups Obtained by Biotransformation of Bicyclic Halolactones

New Bromo- and Iodo-Hydroxylactones with Two Methyl Groups Obtained by Biotransformation of Bicyclic Halolactones

Bioactivity of Endophytic Fungi Isolated from Branch of Jambu Mawar (Syzygium jambos (L.) Alston)

Antimicrobial Activity of Lactones

Contact Info

Product

Resources

About