Synthesis of phosphatidylcholines containing ricinoleic acid

Borsotti, G.; Guglielmetti, Gianfranco; Spera, Silvia; Battistel, Ezio

doi:10.1016/s0040-4020(01)01057-2

Cited by 25 publications

(20 citation statements)

References 14 publications

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“…S1, compounds 8 and 15) gave poor results, another method was tested using oxalyl chloride ( 33 ) to generate the acyl chloride of α-eleostearic acid before the final reaction, but without success. However, better results were observed with DCC/PPyr, as used by Borsotti et al ( 34 ), promoting the acylation of lyso-PC (supplemental Fig. S1, compounds 7 and 14) with anhydride fatty acid derivatives, giving acceptable yields of 48 and 25% for EOPC and OEPC, respectively.…”

Section: Resultsmentioning

confidence: 91%

A continuous spectrophotometric assay that distinguishes between phospholipase A1 and A2 activities

Alaoui

Soulère

Noiriel

et al. 2016

Journal of Lipid Research

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A new spectrophotometric assay was developed to measure, continuously and specifically, phospholipase A1 (PLA1) or phospholipase A2 (PLA2) activities using synthetic glycerophosphatidylcholines (PCs) containing α-eleostearic acid, either at the sn-1 position [1-α-eleostearoyl-2-octadecyl-rac-glycero-3-phosphocholine (EOPC)] or at the sn-2 position [1-octadecyl-2-α-eleostearoyl-rac-glycero-3-phosphocholine (OEPC)]. The substrates were coated onto the wells of microtiter plates. A nonhydrolyzable ether bond, with a non-UV-absorbing alkyl chain, was introduced at the other sn position to prevent acyl chain migration during lipolysis. Upon enzyme action, α-eleostearic acid is liberated and then solubilized into the micellar phase. The PLA1 or PLA2 activity was measured by the increase in absorbance at 272 nm due to the transition of α-eleostearic acid from the adsorbed to the soluble state. EOPC and OEPC differentiate, with excellent accuracy, between PLA1 and PLA2 activity. Lecitase®, guinea pig pancreatic lipase-related protein 2 (known to be a PLA1 enzyme), bee venom PLA2, and porcine pancreatic PLA2 were all used to validate the assay. Compared with current assays used for continuously measuring PLA1 or PLA2 activities and/or their inhibitors, the development of this sensitive enzymatic method, using coated PC substrate analogs to natural lipids and based on the UV spectroscopic properties of α-eleostearic acid, is a significant improvement.

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Section: Resultsmentioning

confidence: 91%

A continuous spectrophotometric assay that distinguishes between phospholipase A1 and A2 activities

Alaoui

Soulère

Noiriel

et al. 2016

Journal of Lipid Research

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“…For example, ricinoleic acid was incorporated into the sn-1 position of egg and soybean lecithin using immobilized PLA 1 (23). The immobilized PLA 1 showed an exclusive regioselectivity toward the sn-1 position, which was absent from known complicated chemical methods (24). The enzymatic production of lysophospholipids from phospholipids was performed using PLA 1 from Aspergillus niger and others (25,26).…”

Section: Plamentioning

confidence: 99%

Phospholipases: Occurrence and production in microorganisms, assay for high‐throughput screening, and gene discovery from natural and man‐made diversity

Song

Han

Rhee

2005

J Americ Oil Chem Soc

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Various kinds of phospholipids have wide industrial applications such as in food and nutraceuticals, cosmetics, agricultural products, and pharmaceuticals. The demand for reliable biocatalysts for the production of phospholipid products, such as phospholipases A 1 , A 2 , C, and D, has steadily increased over the past several decades. A large number of microbial phospholipases have been isolated and characterized, and the increasing availability of these enzymes could eventually lead to the sustained development of phospholipid-related biotechnology. Although a number of reactions have been performed using phospholipases, a reliable and efficient supply of superior phospholipases in quantity is still a challenge for their practical application. High-throughput functional assay methods for phospholipases should be devised to develop superior new species from the huge diversity of phospholipases. Recent biotechnological advances in the discovery of new phospholipase genes from natural sources, such as extremophiles and metagenome libraries, and in the functional enhancement of phospholipases by protein engineering, such as directed evolution, can provide valuable means of rapidly developing practical uses of phospholipases for various applications.

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“…Ricinoleic acid can be easily prepared by hydrolysis of castor oil [15]. The presence of both hydroxy and carboxy groups in the molecule of ricinoleic acid enables it to undergo intermolecular esterification, thus resulting in the formation of the oligomeric ricinoleic acid.…”

Section: Introductionmentioning

confidence: 99%

Oligomeric ricinoleic acid preparation promoted by an efficient and recoverable Brønsted acidic ionic liquid

You¹,

He²,

Gao³

et al. 2020

Beilstein J. Org. Chem.

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Raw material from biomass and green preparation processes are the two key features for the development of green products. As a bio-lubricant in metalworking fluids, estolides of ricinoleic acid are considered as the promising substitute to mineral oil with a favorable viscosity and viscosity index. Thus, an efficient and sustainable synthesis protocol is urgently needed to make the product really green. In this work, an environment-friendly Brønsted acidic ionic liquid (IL) 1-butanesulfonic acid diazabicyclo[5.4.0]undec-7-ene dihydrogen phosphate ([HSO3-BDBU]H2PO4) was developed as the efficient catalyst for the production of oligomeric ricinoleic acid from ricinoleic acid under solvent-free conditions. The reaction parameters containing reaction temperature, vacuum degree, amount of catalyst and reaction time were optimized and it was found that the reaction under the conditions of 190 °C and 50 kPa with 15 wt % of the [HSO3-BDBU]H2PO4 related to ricinoleic acid can afford a qualified product with an acid value of 51 mg KOH/g (which corresponds to the oligomerization degree of 4) after 6 h. Furthermore, the acid value of the product can be adjusted by regulating the reaction time, implying this protocol can serve as a versatile method to prepare the products with different oligomerization degree and different applications. The other merit of this protocol is the facile product separation by stratification and decantation ascribed to the immiscibility of the product and catalyst at room temperature. It is also worth mentioning that the IL catalyst can be used at least for five cycles with high catalytic activity. As a result, the protocol based on the IL catalyst, i.e. [HSO3-BDBU]H2PO4 shows great potential in industrial production of oligomeric ricinoleic acid from ricinoleic acid.

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Synthesis of phosphatidylcholines containing ricinoleic acid

Cited by 25 publications

References 14 publications

A continuous spectrophotometric assay that distinguishes between phospholipase A1 and A2 activities

A continuous spectrophotometric assay that distinguishes between phospholipase A1 and A2 activities

Phospholipases: Occurrence and production in microorganisms, assay for high‐throughput screening, and gene discovery from natural and man‐made diversity

Oligomeric ricinoleic acid preparation promoted by an efficient and recoverable Brønsted acidic ionic liquid

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