Sapogenin is the main block of Camellia
oleifera saponin, which was purified and structurally
modified by the C28 acylation reaction to synthesize 19
new derivatives. The
growth and biofilm inhibition of Staphylococcus aureus and Escherichia coli was measured
to evaluate their antibacterial effects. A three-dimensional quantitative
structure–activity relationship (3D-QSAR) assay indicated that
the antibacterial activities were significantly enhanced after sapogenin
was modified with an aromatic ring or heterocyclic ring and electron-withdrawing
substituents at the meta or para position. Among them, the derivative of sapogenin with a 2-mercapto-4-methyl-5-thiazolyl
acetyl group obviously destroyed bacterial biofilm and made bacteria
lysis. 3D-QSAR provides practical information for the structural design
of sapogenin derivatives with strong antibacterial activity, and the C. oleifera sapogenin derivative 28-O-(2-mercapto-4-methyl-5-thiazolyl)-3β,16α,21β,22α-O-tetrahydroxy-oleantel-2-ene-23-aldehyde (S-16) is an effective candidate as an antibacterial agent for the prevention
of bacterial resistance against antibiotics.
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