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Chemo‐enzymatic synthesis of lipophilic ferulates and their evaluation for antioxidant and antimicrobial activities
Author(s) -
Kanjilal Sanjit,
Shanker Kaki Shiva,
Rao Kotte Sagar,
Reddy Kunduru Konda,
Rao Bhamidipati V. S. K.,
Kumar Kota B. Shiva,
Kantam Mannepalli L.,
Prasad Rachapudi B. N.
Publication year - 2008
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.200800106
Subject(s) - chemistry , ferulic acid , antioxidant , antimicrobial , organic chemistry , fatty acid , moiety , biochemistry
An efficient chemo‐enzymatic synthesis of ferulic acid‐based structured lipids mimicking triacylglycerol with a pendant phenolic moiety was carried out for the first time. Initially, ferulic acid was reduced to coniferyl alcohol, followed by its esterification with fatty acids. The key step in the synthesis was dihydroxylation of the olefinic side chain of coniferyl ester, which was eventually esterified with fatty acids to generate phenolic structured lipids. Two such compounds of varying fatty acid chain lengths were synthesized in good yield. Structural confirmation of both compounds is based on IR, 1 H and 13 C NMR, and MS techniques. The synthesized compounds were tested for in vitro antioxidant and antimicrobial activities. Both compounds exhibited moderate to good antioxidant activity. The phenolic structured lipid with only shorter‐chain fatty acids showed antibacterial activity. Both compounds did not show any antifungal activity.