Bioevaluation and molecular docking analysis of novel phenylpropanoid derivatives as potent food preservative and anti-microbials.

UNLABELLED

Novel derivatives were synthesized using natural scaffold, like phenylpropanoids C-C 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-29.64 μM) and antioxidant (EC-12.67 μM) activity than the reference compounds, kojic acid (IC-50.30 μM) and ascorbic acid (EC-14.55 μM), respectively. Compounds SAM30, SE78, 11F, and CE48 showed better anti-, anti-, and anti- 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.

SUPPLEMENTARY INFORMATION

The online version contains supplementary material available at 10.1007/s13205-020-02636-0.