Further Polycyclic Quinones of Micromonospora sp

The crude acetone extract of a marine Micromonospora sp. strain associated with Eudistoma vannnamei was fractioned with hexane and ethyl acetate. The crude extract and both soluble fractions were assayed against several bacteria strains. The new polycyclic quinones 12‐hydroxy‐9‐propyltetracene‐6,1‐d...

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Published in:Chemistry & biodiversity 2024-07, Vol.21 (7), p.e202301771-n/a
Main Authors: Silva de Freitas Cesário, Hozana Patricia, das Chagas Lima Pinto, Francisco, Marques Canuto, Kirley, Rocha Silveira, Ediberto, Veras Wilke, Diego, Gois Ferreira, Elthon, Marques da Fonseca, Aluísio, Alves de Vasconcelos, Mayron, Teixeira, Edson Holanda, Deusdênia Loiola Pessoa, Otilia
Format: Article
Language:English
Subjects:
Acetic acid
Anthraquinone
Anthraquinones
Antimicrobial activity
Bacteria
Bacterial diseases
Diketones
Drug development
Ethyl acetate
Hexanes
Hydrolase
Micromonospora
Micromonospora sp
Molecular docking
Molecular dynamics
NMR
Nuclear magnetic resonance
Penicillin
polycyclic quinones
Quinones
Staphylococcus aureus
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Summary:The crude acetone extract of a marine Micromonospora sp. strain associated with Eudistoma vannnamei was fractioned with hexane and ethyl acetate. The crude extract and both soluble fractions were assayed against several bacteria strains. The new polycyclic quinones 12‐hydroxy‐9‐propyltetracene‐6,1‐dione (1), 5,12‐dihydroxy‐4‐methoxy‐9‐propyltetracene‐5,12‐dione (2), and 4,6‐dihydroxy‐3‐methoxycarbonyl‐ methyl‐6a‐(oxobutyl)‐5,12‐anthraquinone (3), along with the known 4,6‐dihydroxy‐3‐methoxycarbonyl‐methyl‐6a‐(oxo‐3‐methyl‐butyl)‐5,12‐anthraquinone (4) and 4,6‐dihydroxy‐3‐methoxycarbonyl‐methyl‐6a‐(oxopentyl)‐5,12‐anthraquinone (5) were isolated from the hexane‐soluble fraction, while from the active ethyl acetate fraction were isolated the known 4,6,11‐trihydroxy‐9‐propyltetracene‐5,12‐dione (6), 4‐methoxy‐9‐propyltetracene‐6,11‐dione (7), 7,8,9,10‐tetrahydro‐9‐hydroxy‐4‐methoxy‐9‐propyltetracene‐6,11‐dione (8), and 10β‐carbomethoxy‐7,8,9,10‐tetrahydro‐4,6,7α,9α,11‐pentahydroxy‐9‐propyltetracene‐5,12‐dione (9). The structures of the new compounds were established by interpretation of HRMS and NMR techniques. A study of molecular docking was performed with the compounds from the active ethyl acetate fraction to correlate tentatively with the antimicrobial activity. Molecular docking, RMSD, RMSF, and MM‐GBSA evaluations were performed to investigate the inhibitory activity of 6–8 against the protein PDB‐codex 1MWT, being considered a promising target for studying drug development responsible for inhibiting replication of Staphylococcus aureus. Penicillin G was used as the standard inhibitory. Anthracyclinones 6–8 were the best hydrolase inhibitor with affinity energy −8.1 to −7.9 kcal/mol compared to penicillin G, which presented −6.9 kcal/mol. Both 8 and 7 present potent inhibitory effects against hydrolase through molecular dynamics simulation and exhibit favorable drug‐like properties, promising new hydrolase blockers to fight bacterial infections from Staphylococcus aureus.
ISSN:1612-1872
1612-1880
1612-1880
DOI:10.1002/cbdv.202301771