Ricinoleic acid

Bioactive polymeric formulations for wound healing.[Pubmed:30923437]

Polym Adv Technol. 2018 Jun;29(6):1815-1825.

Ricinoleic acid (RA) has potential to promote wound healing because of its analgesic and anti-inflammatory properties. This study investigates the synthesis and characterization of RA liposomes infused in a hydrogel for topical application. Lecithin liposomes containing RA were prepared and incorporated into a chitosan solution and were subsequently cross-linked with dialdehyde beta-cyclodextrin (Di-beta-CD). Chitosan/Di-beta-CD concentrations and reaction temperatures were varied to alter gelation time, water content, and mechanical properties of the hydrogel in an effort to obtain a wide range of RA release profiles. Hydrogel cross-linking was confirmed by spectroscopy, and liposome and carrier hydrogel morphology via microscopy. Chitosan, Di-beta-CD, and liposome concentrations within the formulation affected the extent of matrix swelling, mechanical strength, and pore and overall morphology. Higher cross-linking density of the hydrogel led to lower water uptake and slower release rate of RA. Optimized formulations resulted in a burst release of RA followed by a steady release pattern accounting for 80% of the encapsulated RA over a period of 48 hours. However, RA concentrations above 0.1 mg/mL were found to be cytotoxic to fibroblast cultures in vitro because of the oily nature of RA. These formulations promoted wound healing when used to treat full thickness skin wounds (2 cm(2)) in Wister male rats. The wound contraction rates were significantly higher compared to a commercially available topical cream after a time period of 21 days. Histopathological analysis of the RA-liposomal chitosan hydrogel group showed that the epidermis, dermis, and subcutaneous skin layers displayed an accelerated yet normal healing compared to control group.

Identification of genes associated with ricinoleic acid accumulation in Hiptage benghalensis via transcriptome analysis.[Pubmed:30679955]

Biotechnol Biofuels. 2019 Jan 21;12:16.

Background: Ricinoleic acid is a high-value hydroxy fatty acid with broad industrial applications. Hiptage benghalensis seed oil contains a high amount of Ricinoleic acid (~ 80%) and represents an emerging source of this unusual fatty acid. However, the mechanism of Ricinoleic acid accumulation in H. benghalensis is yet to be explored at the molecular level, which hampers the exploration of its potential in Ricinoleic acid production. Results: To explore the molecular mechanism of Ricinoleic acid biosynthesis and regulation, H. benghalensis seeds were harvested at five developing stages (13, 16, 19, 22, and 25 days after pollination) for lipid analysis. The results revealed that the rapid accumulation of Ricinoleic acid occurred at the early-mid-seed development stages (16-22 days after pollination). Subsequently, the gene transcription profiles of the developing seeds were characterized via a comprehensive transcriptome analysis with second-generation sequencing and single-molecule real-time sequencing. Differential expression patterns were identified in 12,555 transcripts, including 71 enzymes in lipid metabolic pathways, 246 putative transcription factors (TFs) and 124 long noncoding RNAs (lncRNAs). Twelve genes involved in diverse lipid metabolism pathways, including fatty acid biosynthesis and modification (hydroxylation), lipid traffic, triacylglycerol assembly, acyl editing and oil-body formation, displayed high expression levels and consistent expression patterns with Ricinoleic acid accumulation in the developing seeds, suggesting their primary roles in Ricinoleic acid production. Subsequent co-expression network analysis identified 57 TFs and 35 lncRNAs, which are putatively involved in the regulation of Ricinoleic acid biosynthesis. The transcriptome data were further validated by analyzing the expression profiles of key enzyme-encoding genes, TFs and lncRNAs with quantitative real-time PCR. Finally, a network of genes associated with Ricinoleic acid accumulation in H. benghalensis was established. Conclusions: This study was the first step toward the understating of the molecular mechanisms of Ricinoleic acid biosynthesis and oil accumulation in H. benghalensis seeds and identified a pool of novel genes regulating Ricinoleic acid accumulation. The results set a foundation for developing H. benghalensis into a novel Ricinoleic acid feedstock at the transcriptomic level and provided valuable candidate genes for improving Ricinoleic acid production in other plants.

Tri-Hydroxy-Triacylglycerol Is Efficiently Produced by Position-Specific Castor Acyltransferases.[Pubmed:30610110]

Plant Physiol. 2019 Mar;179(3):1050-1063.

Understanding the biochemistry of triacylglycerol (TAG) assembly is critical in tailoring seed oils to produce high-value products. Hydroxy-fatty acid (HFA) is one such valuable modified fatty acid, which can be produced at low levels in Arabidopsis (Arabidopsis thaliana) seed through transgenic expression of the castor (Ricinus communis) hydroxylase. The resulting plants have low seed oil content and poor seedling establishment, indicating that Arabidopsis lacks efficient metabolic networks for biosynthesis and catabolism of hydroxy-containing TAG. To improve utilization of such substrates, we expressed three castor acyltransferase enzymes that incorporate HFA at each stereochemical position during TAG synthesis. This produced abundant tri-HFA TAG and concentrated 44% of seed HFA moieties into this one TAG species. Ricinoleic acid was more abundant than any other fatty acid in these seeds, which had 3-fold more HFA by weight than that in seeds following simple hydroxylase expression, the highest yet measured in a nonnative plant. Efficient utilization of hydroxy-containing lipid substrates increased the rate of TAG synthesis 2-fold, leading to complete relief of the low-oil phenotype. Partition of HFA into specific TAG molecules increased the storage lipid available for mobilization during seedling development, resulting in a 1.9-fold increase in seedling establishment. Expression of a complete acyltransferase pathway to efficiently process HFA establishes a benchmark in the quest to successfully produce modified oils in plants.

Ricinoleic acid, from castor (Ricinus communis) seed oil, is a high-value hydroxy fatty acid with broad industrial applications. Ricinoleic acid is an attractive feedstock for the production of high-performance lubricants, cosmetics, polymers, surfactants, and coatings.

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