A regioselective, stereoselective synthesis of a diacylglycerophosphocholine hydroperoxide by use of lipoxygenase and lipase

Baba, Naomichi; Yoneda, Kenji; Tahara, Shoich; Iwasa, Junkichi; Kaneko, Takao; Matsuo, Mitsuyoshi

doi:10.1039/c39900001281

Cited by 50 publications

(25 citation statements)

References 5 publications

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“…ML-OOH was prepared in a pure state by enzymatic oxidation of linoleic acid using soybean lipoxygenase and the carboxyl group was methylated with diazomethane followed by silica gel column purification (Baba et al, 1990). The 0939-5075/97/0300-0270 $ 06.00 © 1997 Verlag der Zeitschrift für Naturforschung.…”

Section: Methodsmentioning

confidence: 99%

Preventive Action of Phospholipids on Decomposition of Methyl 13-Hydroperoxyoctadecadienoate

Alam

Nakajima

Baba

1997

Zeitschrift Für Naturforschung C

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Phospholipids. Antioxidant, Ascorbic Acid. Iron, 13-Hydroperoxyoctadecadienoic Acid Methyl EsterThe effects of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine on the thermal decom position of methyl 13-hydroperoxyoctadecadienoate were investigated in a chloroform/methanol mixture. Among the phospholipids tested, phosphatidylserine in hibited the thermal decomposition of methyl 13-hydro peroxyoctadecadienoate to about 30% after exposure to 60 °C for 48h wheareas only 10% remained in the ab sence of the phospholipid for the same heating period. Addition of eugenol with phosphatidylserine showed high synergistic activity which prevented the decomposi tion of the hydroperoxide to a higher extent under the same conditions. Phosphatidylserine was also found to inhibit iron -accelerated decomposition of methyl 13-hydroperoxyoctadecadienoate. Moreover, the decompo sition of the hydroperoxide accelerated by ascorbic acid was effectively prevented by a combination of eugenol and phosphatidylserine.

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Section: Methodsmentioning

confidence: 99%

Preventive Action of Phospholipids on Decomposition of Methyl 13-Hydroperoxyoctadecadienoate

Alam

Nakajima

Baba

1997

Zeitschrift Für Naturforschung C

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“…Early studies reported that some vinyl ethers can react with organic hydroperoxides to form perketals 14,15 . We therefore predicted that this reaction could be applied to the preparation of pure lipid hydroperoxides, and this was achieved using a vinyl ether molecule 2-methoxypropene, MxP Fig.…”

Section: Introductionmentioning

confidence: 99%

Preparation of 13 or 9-Hydroperoxy-9Z,11E (9E,11E) or 10E,12Z (10E,12E)-Octadecadienoic Phosphatidylcholine Hydroperoxide

et al. 2014

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“…For instance, by using these reactions, Porter et al (19) succeeded in purifying fatty acid methyl ester hydroperoxides. The reactivity of MxP with LOOHs other than fatty acid methyl ester hydroperoxides has never been reported; but these studies (16)(17)(18)(19)(20)(21) indicated that the reaction may be useful for the preparation of a wide variety of pure LOOHs (Fig. 1A).…”

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confidence: 99%

Preparation of pure lipid hydroperoxides

Ibusuki

Nakagawa

Asai

et al. 2008

Journal of Lipid Research

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Increasing evidence of lipid peroxidation in food deterioration and pathophysiology of diseases have revealed the need for a pure lipid hydroperoxide (LOOH) reference as an authentic standard for quantification and as a compound for biological studies in this field. Generally, LOOH is prepared from photo-or enzymatically oxidized lipids; however, separating LOOH from other oxidation products and preparing pure LOOH is difficult. Early studies showed the usability of reaction between hydroperoxide and vinyl ether for preparation of pure LOOH. Because the reactivity of vinyl ether with LOOHs other than fatty acid hydroperoxides has never been reported, here, we employed the reaction for preparation of a wide variety of pure LOOHs. Phospholipid, cholesteryl ester, triacylglycerol, or fatty acid was photo-or enzymatically oxidized; the resultant crude sample containing hydroperoxide was allowed to react with a vinyl ether [2-methoxypropene (MxP)]. Liquid chromatography (LC) and mass spectrometry confirmed that MxP selectively reacts with LOOH, yielding a stable MxP adduct (perketal). The lipophilic perketal was eluted at a position away from that of intact LOOH and identified and isolated by LC. Upon treatment with acid, perketal released the original LOOH, which was finally purified by LC. Using our optimized purification procedures, for instance, we produced 75 mg of pure phosphatidylcholine hydroperoxide (.99%) from 100 mg of phosphatidylcholine. Our developed method expands the concept of the perketal method, which provides pure LOOH references. The LOOHs prepared by the perketal method would be used as "gold standards" in LOOH methodology. Because lipid peroxidation is involved in food deterioration (1) and pathophysiology of human diseases (2, 3), there has been a great interest in the accurate measurement of lipid hydroperoxide (LOOH) concentration. This can be performed by several quantitative methods (4-11), and the most sensitive and reliable one is chemiluminescence detection-liquid chromatography (CL-LC) (9-11). Since there is no approved LOOH calibrator ("gold standard") available, it is impossible to compare the LOOH levels from various laboratories around the world.Currently, researchers prepare their own in-house reference LOOH [i.e., lipids (e.g., phospholipids, cholesterols, triacylglycerols, and fatty acids)] are subjected to photo-(12), free radical (13), or enzymatic oxidation (14, 15). The resultant crude or partly purified LOOH is generally used as a calibrator. However, these references are neither officially approved nor do they correspond to each other, particularly with regard to their purity. As frequently mentioned by LOOH researchers, this problem is mainly caused by the difficulty in distinguishing and isolating LOOH from other oxidation products such as hydroxides (13). Therefore, efficient purification of a wide variety of LOOHs is the key to the development of the gold standard not only for the accurate quantification of LOOH but also for the evaluation of its biological fu...

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A regioselective, stereoselective synthesis of a diacylglycerophosphocholine hydroperoxide by use of lipoxygenase and lipase

Cited by 50 publications

References 5 publications

Preventive Action of Phospholipids on Decomposition of Methyl 13-Hydroperoxyoctadecadienoate

Preventive Action of Phospholipids on Decomposition of Methyl 13-Hydroperoxyoctadecadienoate

Preparation of 13 or 9-Hydroperoxy-9Z,11E (9E,11E) or 10E,12Z (10E,12E)-Octadecadienoic Phosphatidylcholine Hydroperoxide

Preparation of pure lipid hydroperoxides

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