Synthesis, Surface Active Properties and Cytotoxicity of Sodium N-Acyl Prolines.

Sodium N-acyl prolines (NaNAPro) were synthesized using mixture of fatty acids obtained from coconut, palm, karanja, Sterculia foetida and high oleic sunflower oils via Schotten-Baumann reaction in 58-75% yields to study the synergetic effect of mixture of hydrophobic fatty acyl functionalities like saturation, unsaturation and cyclopropene fatty acids with different chain lengths and aliphatic hetero cyclic proline head group on their surface and cytotoxicity activities. The products were characterized by chromatographic and spectral techniques. The synthesized products were evaluated for their surface active properties such as surface tension, wetting power, foaming characteristics, emulsion stability, calcium tolerance, critical micelle concentration (CMC) and thermodynamic properties. The results revealed that all the products exhibited superior surface active properties like CMC, calcium tolerance and emulsion stability as compared to the standard surfactant, sodium lauryl sulphate (SLS). In addition, palm, Sterculia foetida and high oleic sunflower fatty N-acyl prolines exhibited promising cytotoxicity against different tumor cell lines.

Synthesis and Characterization of a Novel Phenolic Lipid for Use as Potential Lipophilic Antioxidant and as a Prodrug of Butyric Acid.

Ferulic acid was modified to produce a novel phenolipid containing butyl chains. Ferulic acid was esterified with butanol to produce butyl ferulate which was further dihydroxylated followed by esterification with butyric anhydride to produce the phenolipid containing butyric acid. IR, NMR and MS techniques confirmed the structure of the synthesized structured lipophilic phenolic compound. The synthesized compound was tested for in vitro antioxidant and antimicrobial activities. The produced phenolipid showed moderate antioxidant activity in DPPH (2, 2-diphenyl-1-picrylhydrazyl) radical scavenging assay but in linoleic acid oxidation method, it exhibited good activity compared with the parent compound and the reference compounds. The prepared derivative could find applications as antioxidant in lipophilic systems and also as a potential prodrug of butyric acid. It also showed antibacterial effect against the four bacterial strains studied. The drug-likeness properties of the prepared molecule calculated were in the acceptable ranges according to Lipinski's rule of 5 and suggest that it has potential to cross the blood-brain barrier.

Rapid Accumulation of Total Lipid in Rhizoclonium africanum Kutzing as Biodiesel Feedstock under Nutrient Limitations and the Associated Changes at Cellular Level.

Increase of total lipid and the proportion of the favorable fatty acids in marine green filamentous macroalga Rhizoclonium africanum (Chlorophyceae) was studied under nitrate and phosphate limitations. These stresses were given by both eliminating and doubling the required amounts of nitrate and phosphate salts in the growth media. A significant twofold increase in total lipid (193.03 mg/g) was achieved in cells in absence of nitrate in the culture medium, followed by phosphate limitation (142.65 mg/g). The intracellular accumulation of neutral lipids was observed by fluorescence microscopy. The scanning electron microscopic study showed the major structural changes under nutrient starvation. Fourier transform infrared spectroscopy (FTIR) revealed the presence of ester (C-O-C stretching), ketone (C-C stretching), carboxylic acid (O-H bending), phosphine (P-H stretching), aromatic (C-H stretching and bending), and alcohol (O-H stretching and bending) groups in the treated cells indicating the high accumulation of lipid hydrocarbons in the treated cells. Elevated levels of fatty acids favorable for biodiesel production, that is, C16:0, C16:1, C18:1, and C20:1, were identified under nitrate- and phosphate-deficient conditions. This study shows that the manipulation of cultural conditions could affect the biosynthetic pathways leading to increased lipid production while increasing the proportion of fatty acids suitable for biodiesel production.

Chemo-enzymatic synthesis of rac 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine and its analogues.

The synthesis of rac 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholines (6a-c), blood platelet activating ether lipid analogues has been achieved in a four-step sequence from epichlorohydrin (1). Etherification of epichlorohydrin with different alcohols namely tetradecyl (2a), hexadecyl (2b) and octadecyl (2c) alcohols gave glycidyl ethers (3a-c) with 78-80% yields. The second step involved opening of the epoxide by acetic anhydride to give acetylated products (4a-c, 76-78% yield), which were subsequently hydrolyzed selectively, a key step of the method employing a 1,3 specific lipase to obtain rac 1-O-alkyl-2- acetylglycerol (5a-c) with 45-50% yields. The hydrolyzed products (5a-c) were phosphorylated to obtain rac 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholines (6a-c) in 80-85% yields.

Synthesis of novel lipoamino acid conjugates of sapienic acid and evaluation of their cytotoxicity activities.

Novel lipoamino acids were prepared with the coupling of sapienic acid [(Z)-6-hexadecenoic acid] with α - amino group of amino acids and the resulting N-sapienoyl amino acids were tested for their cytotoxicity activities against four cancer based cell lines. Initially, sapienic acid was synthesized by the Wittig coupling of triphenylphosphonium bromide salt of 6-bromohexanoic acid and decanal with a Z specific reagent. The prepared sapienic acid was subsequently converted to its acid chloride which was further coupled with amino acids by the Schotten-Baumann reaction to form N-sapienoyl amino acid conjugates. Structural characterization of the prepared N-sapienoyl amino acid derivatives was done by spectral data (IR, mass spectra and NMR). These lipoamino acid derivatives were screened for in vitro cytotoxicity evaluation. Cytotoxicity evaluation against four cancer cell lines showed that N-sapienoyl isoleucine was active against three cell lines whereas other derivatives either showed activity against only one or two cell lines with very moderate activity and two derivatives were observed to be inactive against the tested cell lines.