Author
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Hou, Ching |
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Submitted to: Meeting Abstract
Publication Type: Abstract Only Publication Acceptance Date: 10/23/2014 Publication Date: 10/23/2014 Citation: Hou, C.T. 2014. Production of hydroxyl fatty acids, polyol oils, and diacylglycerol by bioprocess [abstract]. United States and Japan Cooperative Program in Natural Resources . Green Chemistry 8. Interpretive Summary: Technical Abstract: Hydroxy fatty acids (HFA), originally found in plant systems, are good examples of the structurally modified lipids, rendering special properties such as higher viscosity and reactivity compared to normal fatty acids. Based on these properties, HFAs possess high industrial potentials in a wide range of applications including resins, waxes, nylons, plastics, lubricants, cosmetics, and additives in coatings and paintings. Potential uses of these HFA are reported as antimicrobial and other bioactive (such as enzyme inhibitor) agents. Since HFA production was limited in plant system, various microbial strains were tested to produce HFAs from different unsaturated fatty acids. Polyol oils (oxygenated acylglycerols) are important starting materials for the manufacture of polymers such as polyurethane. Currently, they are produced by a two-step chemical process involving epoxidation and the subsequent opening of the oxirane ring. Recently, we established a green process to produce polyol oils directly from soybean oil. In this process, diacylglycerols were also produced as co-products which can be used as healthy (dietary) oil. Monohydroxy Fatty Acids: In 1962, a Pseudomonad isolated from fatty material was found to hydrate oleic acid at the cis 9 double bond to produce 10-hydroxystearic acid (10-HSA) with 14% yield. So far, microbial hydration of oleic acid was found in Pseudomonas, Nocardia (Rhodococcus), Corynebacterium, Sphingobacterium, Micrococcus, Absidia, Aspergillus, Candida, Mycobacterium, and Schizosaccharomyces [1]. Flavobacterium DS5 produces 10-keto-stearic acid from oleic acid (10-KSA)[2]. Data indicated that 10-KSA was converted from 10-HSA produced by hydroxylation of oleic acid. It is interesting to find that all unsaturated fatty acids tested are hydrated at the carbon 9,10 positions with the oxygen functionality at C-10 despite their varying degree of unsaturations. It was found that all microbial hydratases hydrate oleic and linoleic acids at the C-10 position [3]. From the chemical structure similarity point of view, 10-HSA and 10-KSA might be used to replace ricinoleic acid, the much higher valued fatty acid. On biological activity, 10-hydroxy-12(Z)-octadecenoic acid decreased muscular tension in rat cardiac muscle. Dihydroxy Fatty Acids: Pseudomonas aeruginosa PR3, isolated from a water sample at a pig farm in Morton, IL, was found to convert oleic acid to a new compound, 7,10-dihydroxy-8(E)-octadecenoic acid (DOD)[4]. The production of DOD from oleic acid is unique in that it involves both hydroxylation and possibly isomerization, an addition of two hydroxy groups at two positions and a rearrangement of the double bond of the substrate molecule. DOD was tested for its potential application in the production of polyurethane rigid foam and skin-care products. Physiological activity tests of DOD revealed that DOD has antimicrobial activity against Bacillus subtilis, Staphylococcus aureus, and a common yeast pathogen, Candida albicans [5]. Subsequent investigation of reactions led to the isolation of 10-hydroxy-8(E)-octadecenoic acid (HOD)[6], an intermediate in the bioconversion of oleic acid to DOD. HOD exhibited strong anti yeast a-glucosidase (EC 3.2.1.20) activity. HOD showed better inhibition activity on a-glucosidase as compared to commercially available antidiabetic remedy, acarbose [7]. Unfortunately in subsequent studies in collaboration with Dr. Kobori of NFRI, we found that HOD did not inhibit the mammalian a-glucosidase activity. Trihydroxy Fatty Acids: Production of trihydroxy unsaturated fatty acids in nature are rare and are produced in trace amounts by plants as antifungal substances. We discovered the production of new compounds, 12,13,17-trihydroxy-9(Z)-octadecenoic acid (12,13,17-THOA) and 12,13,16-trihydroxy-9(Z)-octadecenoic acid (12,13,16-THOA) from linoleic acid by a new microbial cu |
