Microbial reactions on 7alpha-hydroxyfrullanolide and evaluation of biotransformed products for antibacterial activity
| Autor: | Radhika Samerasekera, Emmanuel Schaub, Daniel J. Kozera, Athar Ata, Jordan Betteridge, Paul Holloway |
|---|---|
| Rok vydání: | 2009 |
| Předmět: |
Magnetic Resonance Spectroscopy
Stereochemistry Gram-positive bacteria Chemical structure Molecular Conformation Bioengineering Microbial Sensitivity Tests Asteraceae Gram-Positive Bacteria Biochemistry Biotransformation Rhizopus circinans Organic chemistry Molecular Biology Cunninghamella echinulata Cunninghamella biology Chemistry General Chemistry General Medicine biology.organism_classification Anti-Bacterial Agents Sphaeranthus indicus Molecular Medicine Aspergillus niger Antibacterial activity Sesquiterpenes Bacteria Rhizopus |
| Zdroj: | Chemistrybiodiversity. 6(9) |
| ISSN: | 1612-1880 |
| Popis: | 7alpha-Hydroxyfrullanolide (1), a known sesquiterpenoid, was isolated from Sphaeranthus indicus using an antibacterial-activity-directed fractionation method. This compound had exhibited a significant antibacterial activity against Gram-positive bacteria. Chemical and microbial reactions were performed to prepare eight different analogues of compound 1 in order to evaluate these newly synthesized compounds for antibacterial activity. These compounds were 1beta,7alpha-dihydroxyfrullanolide (2), 7alpha-hydroxy-1-oxofrullanolide (3), 4,5-dihydro-7alpha-hydroxyfrullanolide (4), 11,13-dihydro-7alpha-hydroxyfrullanolide (5), 13-acetyl-7alpha-hydroxyfrullanolide (6), 2alpha,7alpha-dihydroxysphaerantholide (7), 4alpha,5alpha-epoxy-7alpha-hydroxyfrullanolide (8), and 4beta,5beta-epoxy-7alpha-hydroxyfrullanolide (9). Microbial reactions on 1 using whole-cell cultures of Cunninghamella echinulata and Curvularia lunata yielded compounds 2-4. Incubation of compound 1 with the liquid cultures of Apsergillus niger and Rhizopus circinans yielded metabolites 5-7, while 8 and 9 were prepared by carrying out an epoxidation reaction on 1 using meta-chloroperbenzoic acid (mCPBA). Structures of compounds 2-9 were elucidated with the aid of extensive NMR spectral studies. Compounds 2-4 were found to be new metabolites. Compounds 1-9 were evaluated for antibacterial activity and found to exhibit a wide range of bioactivities. Antibacterial-activity data of 1-9 suggested that the bioactivity of 1 is largely due to the presence of C4=C5, C11=C13, and a gamma-lactone moiety. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Plný text