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Oxylipins from long chain polyunsaturated fatty acids and methods of making and using the same

A technology selected from, epoxy, applied in the direction of food preparation, skin care preparations, medical preparations containing active ingredients, etc., can solve the problems of no description of methods to increase the content of beneficial hydroxy fatty acid derivatives, no description, etc.

Inactive Publication Date: 2010-03-03
MARTEK BIOSCIENCES CORP (N D GES D STAATES DELAWARE) COLUMBIA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] Furthermore, none of the above references describe methods for producing these specific compounds in microbial cultures or plants, nor do they describe methods for increasing the content of these beneficial hydroxy fatty acid derivatives in edible oils

Method used

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  • Oxylipins from long chain polyunsaturated fatty acids and methods of making and using the same
  • Oxylipins from long chain polyunsaturated fatty acids and methods of making and using the same
  • Oxylipins from long chain polyunsaturated fatty acids and methods of making and using the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0483]The following examples show that DPAn-6 can be completely converted to monohydroxy diene derivatives by 15-lipoxygenase and more efficiently than DPAn-3 or DHA.

[0484] Soybean 15-lipoxygenase (soybean15-lipoxygenase) (Sigma-Aldrich, St. Louis, MO) at a final concentration of 4 μg / ml was mixed with DHA at a concentration of 100 μM, DPAn-6 at a concentration of 100 μM, or DPAn-6 at a concentration of 100 μM DPAn-3 (NuChek Prep, Elysian, MN) in a solution of 0.05M sodium borate buffer (pH 9.0), and the reaction mixture was incubated at 0°C. The appearance of the monohydroxy conjugated diene derivatives of the fatty acids was monitored by absorbance at 238 nm. Use 28,000M -1 cm -1 The extinction coefficient (extinction coefficient of28,000M -1 cm -1 ) to quantify the conjugated diene product (Shimizu et al; Methods in Enzymology, 1990 Vol 187, 296-306). As shown in Example 1, 100% of DPAn-6 was efficiently converted to its conjugated diene derivative under these condi...

Embodiment 2

[0486] The following examples describe the major 15-lipoxygenase product of DHA.

[0487] DHA (100 μM, NuChek Prep, Elysian, MN) was incubated with 15-LOX (15-lipoxygenase) (4 μg / ml) in 0.05 M sodium borate buffer (pH 9.0) at 4 °C and vigorously stirred for 30 minute. Reaction product with NaBH 4 (0.45 mg / ml) reduction followed by extraction on a solid phase C-18 cartridge (SupelcoDiscovery DSC-19) using absolute ethanol for elution. The reaction products were analyzed by LC / MS / MS using an Agilent 1100 series high performance liquid chromatography (HPLC) device (San Paulo, CA USA) (with an Esquire 3000 ion trap mass spectrometer equipped with an electrospray ionization source (Bruker Daltonics, Billerica MA USA) interface) to analyze. The HPLC is carried out on the LUNAC18(2) column (250×4.6mm, 5 microns, Phenomenex, Torrance CA, USA) by the following conditions: use a mobile phase consisting of 100mM ammonium acetate / 30% methanol / water, in which acetonitrile Gradient from...

Embodiment 3

[0490] The following example identifies the major 15-lipoxygenase product of DPAn-6 and demonstrates the production of mono- and dihydroxy derivatives similar to those produced from DHA (see Example 2).

[0491] DPAn-6 was treated with 15-lipoxygenase and analyzed by LC / MS / MS under the conditions described in Example 2. Figure 3 depicts the structures of the mono- and di-hydroxyl reaction products of this DPAn-6 / 15-LOX reaction. Figure 3B The MS / MS spectrum of the monohydroxyl product is depicted showing the molecular ion (m / z 345) and characteristic fragments of 17-hydroxyDPAn-6. The inset shows the UV spectrum of this compound with the expected peak at 237 nm, which is characteristic of the conjugated diene. Figure 3C and 3D MS / MS spectra of the two dihydroxy products are depicted, where the molecular ions (m / z 361) of 10,17-dihydroxyDPAn-6 (3C) and 7,17-dihydroxyDPAn-6 (3D) are indicated and feature fragments. The inset UV spectrum shows the expected triplet at 270nm ...

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Abstract

Disclosed are novel oxylipins, referred to herein as docosanoids and eicosanoids, that are derived from C22 polyunsaturated fatty acids and from C20 polyunsaturated fatty acids, respectively, and methods of making and using such oxylipins. Also disclosed is the use of docosapentaenoic acid (C22:5n-6) (DPAn-6), docosapentaenoic acid (C22:5n-3) (DPAn-3), and docosatetraenoic acid (DTAn-6: C22:4n-6),docosatrienoic acid (C22:3n-3) (DTrAn-3), docosadienoic acid (C22:2n-6) (DDAn-6), eicosatrienoic acid (C20:3n-3) (ETrAn-3) eicosapentaenoic acid and arachidonic acid as substrates for the productionof novel oxylipins, and to the oxylipins produced thereby. Also disclosed is the use of DPAn-6, DPAn-3, DTAn-6, and / or the oxylipins derived therefrom, and / or novel docosanoids derived from the structures of C22 fatty acids in therapeutic and nutritional or cosmetic applications, and particularly as anti-inflammatory or anti-neurodegenerative compounds. The invention also relates to novel ways ofproducing long chain polyunsaturated acid (LCPUF A)-rich oils and compositions that contain enhanced and effective amounts of LCPUF A-derived oxylipins, and particularly, docosanoids.

Description

[0001] Cross References to Related Applications [0002] This application cross-references U.S. Patent Application 60 / 890,701, filed November 21, 2005, which is incorporated herein by reference technical field [0003] The present invention relates generally to docosapentaenoic acid (docosapentaenoic acid, C22: 5n-6) (DPAn-6), docosapentaenoic acid (docosapentaenoic acid, C22: 5n-3) (DPAn-3) , docosatetraenoic acid (docosatetraenoic acid, DTAn-6: C22: 4n-6), docosatrienoic acid (docosatrienoic acid, C22: 3n-3) (DTrAn-3, also known as DTRAn- 3), docosadienoic acid (docosadienoic acid, C22: 2n-6) (DDAn-6), eicosatrienoic acid (eicosatrienoic acid, C20: 3n-3) (ETrAn-3) and 20 Use of eicosatrienoic acid (C20:3n-9) (ETrAn-9) as a substrate for the production of novel oxylipins and oxylipins produced therefrom. The present invention also relates to the use of DHA, DPAn-6, DPAn-3, DTAn-6, DTrAn-3, DDAn-6, ETrAn-3, ETrAn-9, ARA, EPA and / or oxylipin derived from them, Especially for...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/22C07C53/00
CPCC07C59/42A61Q19/00A61K31/60A61K31/202A23L1/3008A61K8/361C07D303/36C07D303/48A61K45/06A23L33/12A61P25/00A61P25/28A61P29/00A61P39/06A61P43/00A61P9/00A61K8/922A61K2300/00
Inventor 琳达·阿特伯恩威廉·巴克利宾迪·丹吉詹姆斯·弗拉特琼·李达特·文贾莫里玛丽·范埃尔斯维克
Owner MARTEK BIOSCIENCES CORP (N D GES D STAATES DELAWARE) COLUMBIA
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