Carbocyclic Fatty Acids

Ahmad, M. S.; Ali, Shoukath M.; Ahmad, Ateeq; Sheikh, Saifuddin; Ahmad, Imran

doi:10.1016/b978-0-12-809521-8.00004-0

Cited by 6 publications

(5 citation statements)

References 110 publications

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“…Microalgae, such as Picochlorum and Nannochloropsis, are particularly significant due to their euryhaline nature and high eicosapentaenoic acid (EPA) content [16,17]. These unique characteristics make them viable candidates for applications in the nutraceutical and biodiesel production sectors [18,19].…”

Section: Introductionmentioning

confidence: 99%

The Discovery and Characterization of a Novel Microalgal Strain, Picochlorum sp. KCTC AG61293, with Potential for α-Linolenic Acid Production

Kang,

Shin,

2024

JMSE

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Microalgae are highly valued for their rapid biomass production and metabolite synthesis, as well as their abundance of beneficial compounds. They have a variety of applications, including serving as the primary ingredient in biofuels, functional foods, and cosmetics. The genus Picochlorum, which was established to represent the unique characteristics of “Nannochloris-like” algae, exhibits rapid growth and a high salt tolerance. The morphology, molecular phylogeny, and fatty acid composition of an unspecified Picochlorum strain KCTC AG61293 found in Korean coastal waters were investigated. The strain exhibited a unique cell morphology and reproduction type compared to other Picochlorum species, as determined using light microscopy, fluorescence microscopy, and field emission scanning electron microscopy (FE-SEM). The vegetative cells were elongated and cylindrical in shape, underwent binary fission, and possessed a parietal chloroplast. A molecular phylogenetic analysis using nuclear small subunit ribosomal RNA sequences showed that Picochlorum sp. (KCTC AG61293) belongs to the Picochlorum clade and is closely related to the genus Nannochloris. Compared to other reference species, Picochlorum sp. (KCTC AG61293) had higher levels of saturated fatty acids (SFAs) and alpha-linolenic acid (ALA). The increased levels of SFAs and ALA suggest that Picochlorum sp. (KCTC AG61293) may be a promising candidate for biofuel production and other industrial uses.

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Section: Introductionmentioning

confidence: 99%

The Discovery and Characterization of a Novel Microalgal Strain, Picochlorum sp. KCTC AG61293, with Potential for α-Linolenic Acid Production

Kang,

Shin,

2024

JMSE

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“…As discussed by Row and Prescher, it is often useful to look to nature for new bioorthogonal probes, as even rare motifs present in natural products indicate stability and compatibility in living systems. [27] In light of this, Nunn's 1952 discovery [38] of the plant metabolite sterculic acid (StA, 1), a carbocyclic fatty acid [39] found in the kernels of Sterculia foetida, piqued our interest. This 18-carbon cis-unsaturated lipid contains a naturally occurring 1,2-substituted cyclopropene-ring at C9-C10.…”

Section: Introductionmentioning

confidence: 99%

Live‐Cell Imaging of Sterculic Acid—a Naturally Occurring 1,2‐Cyclopropene Fatty Acid—by Bioorthogonal Reaction with Turn‐On Tetrazine‐Fluorophore Conjugates**

et al. 2022

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In the field of lipid research, bioorthogonal chemistry has made the study of lipid uptake and processing in living systems possible, whilst minimising biological properties arising from detectable pendant groups. To allow the study of unsaturated free fatty acids in live cells, we here report the use of sterculic acid, a 1,2-cyclopropene-containing oleic acid analogue, as a bioorthogonal probe. We show that this lipid can be readily taken up by dendritic cells without toxic side effects, and that it can subsequently be visualised using an inverse electron-demand Diels-Alder reaction with quenched tetrazine-fluorophore conjugates. In addition, the lipid can be used to identify changes in protein oleoylation after immune cell activation. Finally, this reaction can be integrated into a multiplexed bioorthogonal reaction workflow by combining it with two sequential copper-catalysed Huisgen ligation reactions. This allows for the study of multiple biomolecules in the cell simultaneously by multimodal confocal imaging.

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“…Renewable oils have been used for the production of not only biodiesel but also oleochemicals for the chemical industry. These include fatty acids and their methyl esters, fatty amines, and fatty alcohols. ,− …”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Cascade Conversion of Linoleic Acid into a Secondary Fatty Alcohol Using a Combination of 13S-Lipoxygenase, Chemical Reduction, and a Photo-Activated Decarboxylase

Cha

Lee

et al. 2021

ACS Sustainable Chem. Eng.

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Linoleic acid serves as a starting material in the production of various oleochemicals. Here, we have investigated the transformation of linoleic acid into 13S-hydroxy-(9Z,11E)-octadecadienoic acid (13-HOD) (17) and 6S-hydroxy-(7E,9Z)heptadecadiene (6-HHD) (18) by using 13S-lipoxygenase from Pseudomonas aeruginosa (Pa-LOX) and photo-activated decarboxylase from Chlorella variabilis NC64A (Cv-FAP). Remarkably, the recombinant Escherichia coli expressing Pa-LOX was able to produce 13S-hydroperoxy-(9Z,11E)-octadecadienoic acid ( 16) at a maximum rate of 850 μmol/g dry cells/min. This allowed the accumulation of 13-HOD (17) to 161 mM (48 g/L) concentration from 200 mM linoleic acid in the reaction medium within 3.5 h. We have also demonstrated that the fatty acids, including CC bonds in cis-and trans-forms [e.g., 13-HOD (17)], were subjected to photo-activated decarboxylation by Cv-FAP. Ultimately, the secondary fatty alcohol [i.e., 6-HHD ( 18)] was produced from linoleic acid through the chemo/enzymatic cascade transformation, consisting of dioxygenation of linoleic acid by intracellular Pa-LOX and reduction of the hydroperoxy fatty acid (16) by Tris(2-carboxyethyl) phosphine or cysteine. Moreover, the photoactivated decarboxylation of the hydroxy fatty acid (17) by intracellular Cv-FAP achieved a conversion of ca. 74% in a one-pot process. This study will contribute to the valorization of γ-linolenic and arachidonic acid, as well as linoleic acid, which are the substrates of Pa-LOX.

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Carbocyclic Fatty Acids

Cited by 6 publications

References 110 publications

The Discovery and Characterization of a Novel Microalgal Strain, Picochlorum sp. KCTC AG61293, with Potential for α-Linolenic Acid Production

The Discovery and Characterization of a Novel Microalgal Strain, Picochlorum sp. KCTC AG61293, with Potential for α-Linolenic Acid Production

Live‐Cell Imaging of Sterculic Acid—a Naturally Occurring 1,2‐Cyclopropene Fatty Acid—by Bioorthogonal Reaction with Turn‐On Tetrazine‐Fluorophore Conjugates**

Chemoenzymatic Cascade Conversion of Linoleic Acid into a Secondary Fatty Alcohol Using a Combination of 13S-Lipoxygenase, Chemical Reduction, and a Photo-Activated Decarboxylase

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