Antibacterial Prenylated p-Hydroxybenzoic Acid Derivatives from Oberonia myosurus and Identification of Putative Prenyltransferases

Twelve hitherto unknown tandem prenylated p-hydroxybenzoic acid derivatives, namely, oberoniamyosurusins A-L, together with five known derivatives, were isolated from an EtOH extract of the whole parts of the plant Oberonia myosurus. Compounds 10, 13, and 17 exhibited moderate inhibitory activity against Staphylococcus aureus subsp. aureus ATCC29213 with MIC50 values ranging from 7.6 to 23 mu g/mL. To determine the biosynthetic pathway of this class of tandem prenyl-substituted compounds, the full-length transcriptome of O. myosurus was sequenced, yielding 19.09 Gb of clean data and 10 949 nonredundant sequences. Two isoforms of p-hydroxybenzoic acid prenyltransferases were annotated and functionally characterized as the enzymes that might be involved in the biosynthesis of nervogenic acid (13) in Pichia pastoris.

Automated summary

Twelve previously unknown tandem prenylated p-hydroxybenzoic acid derivatives, named oberoniamyosurusins A-L, were isolated from the plant Oberonia myosurus, along with five known derivatives. Some of the compounds exhibited moderate inhibitory activity against Staphylococcus aureus. The biosynthetic pathway of these compounds was investigated using transcriptome sequencing of O. myosurus, identifying potential enzymes involved in nervogenic acid biosynthesis.