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Chem Biodivers ; 21(6): e202400463, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38606752

ABSTRACT

One novel compound, (R)-3, 6-diethoxy-4-hydroxycyclohex-3-en-1-one (1) and thirteen known compounds were isolated from the waste tobacco leaves. The structures of two compounds (1-2) were confirmed and attributed firstly by the extensive spectroscopic data, including 1D/2D NMR, IR, HR-ESI-MS, CD, and ECD spectra. Notably, seven compounds (2, 3, 9, 10, 11, 12, and 13) exhibited better tyrosinase inhibitory activity than the positive control kojic acid. The binding modes of these compounds revealed that their structure formed strong hydrogen bonds and van der Waals forces with the active sites of tyrosinase. These results indicated that waste tobacco leaves are good resources for developing tyrosinase inhibitors.


Subject(s)
Enzyme Inhibitors , Monophenol Monooxygenase , Nicotiana , Plant Leaves , Monophenol Monooxygenase/antagonists & inhibitors , Monophenol Monooxygenase/metabolism , Plant Leaves/chemistry , Nicotiana/chemistry , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/pharmacology , Enzyme Inhibitors/isolation & purification , Molecular Structure , Structure-Activity Relationship , Molecular Docking Simulation
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