Synthesis, characterization and evaluation of antiproliferative activity of diisopropylphenyl esters of fatty acids from selected oils

Yasa, Sathyam Reddy; Kaki, Shiva Shanker; Rao, Bala Bhaskara; Jain, Nishant; Penumarthy, Vijayalakshmi

doi:10.1007/s00044-016-1564-4

Cited by 6 publications

(3 citation statements)

References 28 publications

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“…Earlier reports on the production of phenolipids were focused on the incorporation of phenolic compounds into triglycerides where a number of phenolic acids were transesterified with different oils or triglycerides [6]. Apart from these structured phenolipids, different fatty acids were esterified with phenolic compounds to produce novel esters which were evaluated for anti-oxidant and antimicrobial activities [7–8]. However, there are very few reports where the phenolic acids have been derivatized with other functionalities apart from esters.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

Narra¹,

Kaki²,

Misra³

et al. 2017

Beilstein J. Org. Chem.

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The synthesis of five novel methyl 10-undecenoate-based lipoconjugates of phenolic acids from undecenoic acid was carried out. Undecenoic acid was methylated to methyl 10-undecenoate which was subjected to a thiol–ene reaction with cysteamine hydrochloride. Further amidation of the amine was carried out with different phenolic acids such as caffeic, ferulic, sinapic, coumaric and cinnamic acid. All synthesized compounds were fully characterized and their structures were conﬁrmed by spectral data. The anti-oxidant activity of the synthesized lipoconjugates of phenolic acids was studied by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay and also by the inhibition of linoleic acid oxidation in micellar medium by differential scanning calorimetry (DSC). The prepared compounds were also screened for their cytotoxic activity against five cell lines. It was observed that the lipoconjugates of caffeic acid, sinapic acid, ferulic acid, and coumaric acid displayed anticancer and anti-oxidant properties. The anticancer properties of these derivatives have been assessed by their IC50 inhibitory values in the proliferation of MDA-MB231, SKOV3, MCF7, DU 145 and HepG2 cancer cell lines.

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Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

Narra¹,

Kaki²,

Misra³

et al. 2017

Beilstein J. Org. Chem.

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“…13 However, most of the species of silkworm are yet to be exploited as a source of oil through the extraction of omega-3 fatty acids, especially ALA. The silkworm pupal oils are witnessed to have several bio-activities, namely antioxidants, 14 anticancer, 15 vasculoprotective, 16 antibacterial, 17 hypercholesterolemic, 14 and antiulcerative (Long et al, 2019) 18 (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Tasar silkworm pupal oil: An excellent source of edible oil for industrial and therapeutic applications

Srivastava,

Singh,

Ramappa

2023

J. Drug Delivery Ther.

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Polyunsaturated fatty acids are widely recognized due to their remedial properties. In our previous studies, we reported that Tasar silkworm pupal oil (TSPO) is rich in polyunsaturated fatty acids, particularly alpha-linolenic acid (ALA). Further we also extracted ALA from TSPO and reported its significant anticancer activity. In the present study, extraction of TSPO and physico-chemical characterizations including saponification, acid, peroxide, iodine pH values, and colour determination were carried out to investigate the edible properties of TSPO for commercialization as a therapeutically active functional food. Further, the anti-diabetic activity of TSPO were analyzed by α-amylase inhibition assay. The saponification (154.75 ± 0.581mg KOH/g), acid (6.24 ± 0.421 mg KOH/g), peroxide (16.20 ± 0.265 meq/kg), iodine (40.33 ± 0.577g/100 ml), pH (6.17), and colour (14 Y+1.2 R) values were within the permissible range for commercialization. In addition to this, the results of the α-amylase inhibition assay showed that TSPO exhibited an IC50 value of 207339 µg/ml. The results may facilitate the use of TSPO oil in therapeutic and functional food applications Keywords: Characterization; Commercialization; Tasar pupal oil; Silkworm pupae.

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“…Fatty acids and their derivatives have been found to have anticancer activity . Also, fatty acids and their derivatives are precursors of many biomolecules with roles in the regulation of blood pressure, and in the prevention of heart disease and some chronic diseases …”

Section: Introductionmentioning

confidence: 99%

[(para‐Cymene)Ru(dppp)Cl][PF₆]‐Catalysed Stereospecific Synthesis of O‐Dienyl Esters, and Evaluation of the Anticancer Activity of a Long‐Chain Fatty Acid O‐Dienyl Ester

et al. 2017

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O‐Dienyl esters are obtained through the regio‐ and stereospecific addition of both aromatic and aliphatic carboxylic acids to terminal propargylic alcohols, with the sequential formation of a carbon–oxygen bond and dehydration, in the presence of [(p‐cymene)Ru(dppp)Cl][PF6] (1). Also, the cytotoxicity and anticancer activity of the newly synthesized O‐dienyl ester (Z)‐3‐methylbuta‐1,3‐dienyl oleate have been investigated.

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Synthesis, characterization and evaluation of antiproliferative activity of diisopropylphenyl esters of fatty acids from selected oils

Cited by 6 publications

References 28 publications

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

Tasar silkworm pupal oil: An excellent source of edible oil for industrial and therapeutic applications

[(para‐Cymene)Ru(dppp)Cl][PF₆]‐Catalysed Stereospecific Synthesis of O‐Dienyl Esters, and Evaluation of the Anticancer Activity of a Long‐Chain Fatty Acid O‐Dienyl Ester

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Synthesis, characterization and evaluation of antiproliferative activity of diisopropylphenyl esters of fatty acids from selected oils

Cited by 6 publications

References 28 publications

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

Tasar silkworm pupal oil: An excellent source of edible oil for industrial and therapeutic applications

[(para‐Cymene)Ru(dppp)Cl][PF6]‐Catalysed Stereospecific Synthesis of O‐Dienyl Esters, and Evaluation of the Anticancer Activity of a Long‐Chain Fatty Acid O‐Dienyl Ester

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[(para‐Cymene)Ru(dppp)Cl][PF₆]‐Catalysed Stereospecific Synthesis of O‐Dienyl Esters, and Evaluation of the Anticancer Activity of a Long‐Chain Fatty Acid O‐Dienyl Ester