Abstract
Naringin dihydrochalcone (DC) is originally derived from the flavonoid naringin, which occurs naturally in citrus fruits, especially in grapefruit. It is used as an artificial sweetener with a strong antioxidant activity with potential applications in food and pharmaceutical fields. At present, enzymatic and chemical methods to make products of naringin DC by hydroxylation reactions have not been developed. Here, an enzymatic strategy for the efficient synthesis of potentially valuable products from naringin DC, a glycoside of phloretin, was developed using Bacillus megaterium CYP102A1 monooxygenase. The major product was identified to be neoeriocitrin DC by NMR and LC-MS analyses. Sixty-seven mutants of CYP102A1 were tested for hydroxylation of naringin DC to produce neoeriocitrin DC. Six mutants with high activity were selected to determine the kinetic parameters and total turnover numbers (TTNs). The kcat value of the most active mutant was 11 min−1 and its TTN was 315. The productivity of neoeriocitrin DC production increased up to 1.1 mM h−1, which corresponds to 0.65 g L−1 h−1. In this study, we achieved a regioselective hydroxylation of naringin DC to produce neoeriocitrin DC.
Highlights
Dihydrochalcone (DC) is a bicyclic flavonoid family with two aromatic rings and a saturated C3 bridge [1]
To determine the ability of CYP102A1toward to hydroxylate the activity of wild type (WT)
The 60on mutants used for first screening were selected based works showing their improved a number of non-natural substrates, such as natural on our and previous works showing their improved catalytic activities onrelative a number of CYP102A1, non-natural products pharmaceuticals
Summary
Dihydrochalcone (DC) is a bicyclic flavonoid family with two aromatic rings and a saturated C3 bridge [1]. DC compounds are mainly found in citrus fruits, grapefruits, and apples, and they play an important role in resisting biotic or abiotic stresses in plant [2,3]. More than 200 DC compounds have been identified from over 30 plant families [4]. As DC compounds show strong antioxidant activities, a large number of studies have researched the potential benefits of DC compounds to human health. They were demonstrated to be effective in preventing different physiopathological processes [3], notably diabetes [5] and bone resorption [6]. Scientists have more often been attracted by in vitro and in vivo biological activities of DC compounds
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