The growing and aging population coupled with the demand for environmentally sustainable solutions necessitates innovative developments in pharmaceuticals and agrochemicals. Terpenoids, a diverse group of specialized metabolites, have the potential to address these mounting challenges. Chapter 1 reviews terpene biosynthesis, while the remaining chapters cover research advances that improve our understanding of plant terpene biosynthesis and its applications. These research chapters cover the characterization of multiple CYP76BK1 orthologs involved in furanoclerodane metabolism, the discovery of the notably promiscuous Ajuga reptans CYP736A358, and exploration of novel enzyme-synthetic substrate analog combinations to yield semi-synthetic products. The CYP76BK1 orthologs were shown to catalyze the production of furan and one of two distinct lactone ring moieties on primarily clerodane backbones. In contrast, CYP736A358 exhibited limited product promiscuity, yet remarkable substrate promiscuity towards diterpenes, suggesting its place as a biotechnology multi-tool. In the final chapter, evolutionarily distinct sesquiterpene synthases natively producing similar products demonstrated different preferences towards synthetic analogs of their native substrate, the products of which had varied anti-fungal activities. These findings not only underscore the enzymatic flexibility within terpene specialized metabolism but provide new tools to produce commercially relevant terpenoids.
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