Bioevaluation and molecular docking analysis of novel phenylpropanoid derivatives as potent food preservative and anti-microbials
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 an...
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Published in | 3 Biotech Vol. 11; no. 2; p. 70 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
Cham
Springer International Publishing
01.02.2021
Springer Nature B.V |
Subjects | |
Online Access | Get full text |
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Summary: | 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. |
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ISSN: | 2190-572X 2190-5738 |
DOI: | 10.1007/s13205-020-02636-0 |