4.3 Article

Paradox of omega-3 PUFA oxidation

Journal

EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY
Volume 116, Issue 10, Pages 1268-1279

Publisher

WILEY-BLACKWELL
DOI: 10.1002/ejlt.201400114

Keywords

DHA; Emulsion; EPA; Liposome; Micelle; Oxidative stability

Ask authors/readers for more resources

The oxidative stability of polyunsaturated fatty acids (PUFAs) in micelles and in liposomes is dramatically different from that observed in the bulk phase and in organic solvents. In aqueous micelles, docosahexaenoic acid (DHA, 22:6n-3) is oxidatively most stable followed by EPA (20:5n-3), arachidonic acid (AA, 20:4n-6), alpha-linolenic acid (18:3n-3), gamma-linolenic acid (18:3n-6), and linoleic acid (LA, 18:2n-6), respectively. In phosphatidylcholine (PC) liposomes, DHA-PC showed the highest oxidative stability followed by AA-PC and LA-PC in that order. This order was completely opposite to that found in bulk and in organic solvent systems. NMR and GC-MS analysis and a computer modelling approach to hydroperoxide isomer composition suggest that the physical and stereochemical characteristics of DHA molecules in the aqueous phase are related to its unusually high oxidative stability. The possible mechanisms are a tight packing conformation ofDHAmolecules and the presence of water molecule near the double bonds of DHA, which may inhibit hydrogen abstraction from the bis-allylic positions of DHA.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.3
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Biotechnology & Applied Microbiology

Factors influencing the induction of adventitious bud and callus in the brown alga Sargassum horneri (Turner) C. Agardh

Toshiki Uji, Daisuke Nanaumi, Chikara Kawagoe, Naotsune Saga, Kazuo Miyashita

JOURNAL OF APPLIED PHYCOLOGY (2016)

Article Food Science & Technology

Does squalene alter the antioxidant potential of astaxanthin and fucoxanthinol? In vitro evidence in RAW 264.7 cells, a murine macrophage

Sangeetha Ravi Kumar, Bhaskar Narayan, Yuki Kizawa, Masashi Hosokawa, Kazuo Miyashita

JOURNAL OF FOOD SCIENCE AND TECHNOLOGY-MYSORE (2016)

Article Chemistry, Applied

Formation of Acrolein in the Autoxidation of Triacylglycerols with Different Fatty Acid Compositions

Ako Shibata, Mariko Uemura, Masashi Hosokawa, Kazuo Miyashita

JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY (2015)

Article Biochemistry & Molecular Biology

Dietary ALA from Spinach Enhances Liver n-3 Fatty Acid Content to Greater Extent than Linseed Oil in Mice Fed Equivalent Amounts of ALA

Miho Kuroe, Hiroyuki Kamogawa, Masashi Hosokawa, Kazuo Miyashita

LIPIDS (2016)

Article Chemistry, Medicinal

Fucoxanthinol, Metabolite of Fucoxanthin, Improves Obesity-Induced Inflammation in Adipocyte Cells

Hayato Maeda, Shogo Kanno, Mei Kodate, Masashi Hosokawa, Kazuo Miyashita

MARINE DRUGS (2015)

Article Food Science & Technology

Squalene modulates fatty acid metabolism: Enhanced EPA/DHA in obese/diabetic mice (KK-Ay) model

Sangeetha Ravi Kumar, Ippei Yamauchi, Bhaskar Narayan, Ami Katsuki, Masashi Hosokawa, Kazuo Miyashita

EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY (2016)

Article Chemistry, Applied

Fabrication of Fucoxanthin-Loaded Microsphere (F-LM) By Two Steps Double-Emulsion Solvent Evaporation Method and Characterization of Fucoxanthin before and after Microencapsulation

Dedi Noviendri, Irwandi Jaswir, Muhammad Taher, Farahidah Mohamed, Hamzah Mohd Salleh, Ibrahim Ali Noorbatcha, Fitri Octavianti, Widya Lestari, Ridar Hendri, Hasna Ahmad, Kazuo Miyashita, Alias Abdullah

JOURNAL OF OLEO SCIENCE (2016)

Article Chemistry, Applied

Bioconversion of Docosapentaenoic Acid in Human Cell Lines, Caco-2, HepG2, and THP-1

Yanzhu Tian, Donato Romanazzi, Kazuo Miyashita, Masashi Hosokawa

JOURNAL OF OLEO SCIENCE (2016)

Article Chemistry, Applied

Inhibitory Effect of Dihydrosphingosine with α-Tocopherol on Volatile Formation during the Autoxidation of Polyunsaturated Triacylglycerols

Mariko Uemura, Ako Shibata, Masashi Hosokawa, Ai Iwashima-Suzuki, Makoto Shiota, Kazuo Miyashita

JOURNAL OF OLEO SCIENCE (2016)

Article Cell Biology

Combined effect of astaxanthin and squalene on oxidative stress in vivo

Sangeetha Ravi Kumar, Bhaskar Narayan, Yuki Sawada, Masashi Hosokawa, Kazuo Miyashita

MOLECULAR AND CELLULAR BIOCHEMISTRY (2016)

Article Chemistry, Applied

Fatty Acid and Lipid Class Composition of the Microalga Phaeodactylum tricornutum

Yu-Hong Yang, Lei Du, Masashi Hosokawa, Kazuo Miyashita, Yume Kokubun, Hisayoshi Arai, Hiroyuki Taroda

JOURNAL OF OLEO SCIENCE (2017)

Article Biochemistry & Molecular Biology

Regulation of Polyunsaturated Fatty Acid Biosynthesis by Seaweed Fucoxanthin and Its Metabolite in Cultured Hepatocytes

Tsunehiro Aki, Masaya Yamamoto, Toshiaki Takahashi, Kohki Tomita, Rieko Toyoura, Kazuhiro Iwashita, Seiji Kawamoto, Masashi Hosokawa, Kazuo Miyashita, Kazuhisa Ono

LIPIDS (2014)

Article Nutrition & Dietetics

Reduction of HbA1c levels by fucoxanthin-enriched akamoku oil possibly involves the thrifty allele of uncoupling protein 1 (UCP1): a randomised controlled trial in normal-weight and obese Japanese adults

Nana Mikami, Masashi Hosokawa, Kazuo Miyashita, Hitoshi Sohma, Yoichi M. Ito, Yasuo Kokai

JOURNAL OF NUTRITIONAL SCIENCE (2017)

Article Biochemistry & Molecular Biology

The dietary effect of milk sphingomyelin on the lipid metabolism of obese/diabetic KK-Ay mice and wild-type C57BL/6J mice

Ippei Yamauchi, Mariko Uemura, Masashi Hosokawa, Ai Iwashima-Suzuki, Makoto Shiota, Kazuo Miyashita

FOOD & FUNCTION (2016)

No Data Available