LAUSR

Novel derivatives were synthesized using natural scaffold, like phenylpropanoids C 6 –C 3 backbone to reduce unfavorable browning of food due to tyrosinase and oxidative spoilage. Most of the compounds displayed mushroom tyrosinase inhibition better than kojic acid. Compound CE48 exhibited better anti-tyrosinase (IC 50 -29.64 μM) and antioxidant (EC 50 -12.67 μM) activity than the reference compounds, kojic acid (IC 50 -50.30 μM) and ascorbic acid (EC 50 -14.55 μM), respectively. Compounds SAM30, SE78, 11F, and CE48 showed better anti- B. subtilis , anti- S. aureus , and anti- A. niger activity, respectively, compared to their parents. Molecular docking studies between inhibitors and mushroom tyrosinase corroborated the experimental reports, except SAM30 (glide score − 8.117) and SE78 (glide score − 6.151). In silico absorption, distribution, metabolism, excretion/toxicity (ADME/T) and toxicological studies of these newly synthesized compounds exhibited acceptable pharmacokinetic and safety profiles, like good aqueous solubility (− 3.34 to − 7.57), low human oral absorption (e.g., SAM30, SE78, FAM34), low gut–blood barrier permeability [36.67–209.88 nm/s in Cancer coli-2 (Caco-2) cells] and [19.45–91.51 nm/s in Madin-Darby Canine Kidney (MDCK) cells], low blood–brain barrier penetration, non-mutagenicity, and non-carcinogenicity. Interestingly, the synthesized compounds also possessed multifunctional properties, like microbial growth inhibitor, free radicals scavenger, and it also prevented browning of raw fruits and vegetables by inhibiting tyrosinase enzyme.