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Yarra M.,Center for Lipid Research Division Indian Institute of Chemical TechnologyTarnaka | Kaki S.S.,Center for Lipid Research Division Indian Institute of Chemical TechnologyTarnaka | Prasad R.B.N.,Center for Lipid Research Division Indian Institute of Chemical TechnologyTarnaka | Mallampalli K.S.L.,Center for Lipid Research Division Indian Institute of Chemical TechnologyTarnaka | And 2 more authors.
European Journal of Lipid Science and Technology | Year: 2015

A series of novel phenolipids were synthesized by coupling (Z)-methyl-12-aminooctadec-9-enoate with substituted aromatic phenolic acids. The substrate (Z)-methyl-12-aminooctadec-9-enoate was synthesized from methyl ricinoleate employing a four-step procedure. The synthesized phenolipids were thoroughly characterized by FT-IR, 1H NMR, 13C NMR, ESI-MS, and HRMS spectral analysis. The in vitro antioxidant activities of synthesized compounds were evaluated by 2, 2-diphenyl-1-picrylhydrazyl radical (DPPH•), superoxide free radical scavenging activity, and lipid peroxidation inhibitory activities. The novel phenolic compounds were compared in terms of antioxidant activity with the commercial antioxidants, namely butylated hydroxy toluene (BHT) and α-tocopherol as reference compounds. The antioxidant screening data of all the synthesized compounds revealed that DPPH free radical scavenging activity, superoxide, and lipid peroxidation inhibitory activity of caffeic and gallic acid substituted phenolipids exhibited excellent activity as compared to commercial antioxidants, BHT, and α-tocopherol. The synthesized phenolipids were also evaluated for anticancer activities against four different cancer cell lines namely DU145, HePG2, SKOV3, MDA-MB-231. Among these compounds, 7a, 7b, 7d, 7e which were derived from cinnamic acid-based phenolic acids and 8b which is derived from vanillic acid exhibited good anticancer activity against the tested cell lines. Practical applications: Lipophilization of phenolic acids improves their antioxidant and anticancer properties. The (Z)-methyl-12-aminooctadec-9-enoate-based phenolipids can be exploited in a number of lipophilic antioxidant and anticancer formulations. A panel of (Z)-methyl-12-aminooctadec-9-enoate-based phenolipids are synthesized for the first time from methyl ricinoleate, an unusual fatty acid isolated from castor oil. These compounds were evaluated for antioxidant properties, and gallic and caffeic acid-based phenolipids exhibited extraordinary properties compared to BHT and α-tocopherol commercially available antioxidants used in food and pharmaceutical formulations. These compounds were evaluated for anticancer activity for the first time, where these have exhibited good to moderate activity. Hence, (Z)-methyl-12-aminooctadec-9-enoate-based phenolipids can be exploited in a number of lipophilic antioxidant and anticancer formulations. A panel of (Z)-methyl-12-aminooctadec-9-enoate-based phenolipids are synthesized for the first time from methyl ricinoleate, an unusual fatty acid isolated from castor oil. These compounds were evaluated for antioxidant properties, and gallic and caffeic acid-based phenolipids exhibited extraordinary properties compared to BHT and α-tocopherol commercially available antioxidants used in food and pharmaceutical formulations. These compounds were evaluated for anticancer activity for the first time, where these have exhibited good to moderate activity. Hence, (Z)-methyl-12-aminooctadec-9-enoate-based phenolipids can be exploited in a number of lipophilic antioxidant and anticancer formulations. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Bhaskar Rao A.,Medicinal Chemistry and Pharmacology DivisionCSIR Indian Institute of Chemical TechnologyTarnaka | Prasad E.,Medicinal Chemistry and Pharmacology DivisionCSIR Indian Institute of Chemical TechnologyTarnaka | Deepthi S.S.,Medicinal Chemistry and Pharmacology DivisionCSIR Indian Institute of Chemical TechnologyTarnaka
Archiv der Pharmazie | Year: 2014

Medicinal plants proved to be a rich source in exploring a variety of lead structures in the development of new drugs. The natural curcuminoids have gained considerable attention in recent years for their multiple beneficial pharmacological and biological activities. Clinical application of these curcuminoids is often impaired due to their poor water solubility, resulting in low in vivo bioavailability of the active compound in humans. The objective of the present study is to synthesize glucosyl conjugates of curcumin 1 and tetrahydrocurcumin 4 and to evaluate their biological activities. The study highlights the synthesis of curcumin-β-di-glucoside 3 (yield 71%) and tetrahydrocurcumin-β-di-glucoside 6 (yield 64%) in good yields in a biphasic reaction medium using a phase transfer catalyst under simple and ecofriendly conditions. Both the glucosyl curcuminoids showed enhanced antioxidant, tyrosinase enzyme inhibitory, antimicrobial and potent cytotoxic activity. The improved biological activity may be due to the increased solubility of the glucosyl conjugated compounds compared to the native curcuminoids; this was further confirmed by partition coefficient studies. Thus, the synthesized glucosyl curcumin may serve as promising future therapeutic molecule in the management of cancer, whereas glucosyl tetrahydrocurcumin can be a useful ingredient in achromatic food and in cosmetic applications. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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