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Preparation of Phosphatidylated Terpenes via Phospholipase D-Mediated Transphosphatidylation

Yamamoto, Yukihiro ; Hosokawa, Masashi ; Kurihara, Hideyuki ; Miyashita, Kazuo

Journal of the American Oil Chemists' Society, 2008-04, Vol.85 (4), p.313-320 [Periódico revisado por pares]

Berlin/Heidelberg: Berlin/Heidelberg : Springer-Verlag

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Título:
Preparation of Phosphatidylated Terpenes via Phospholipase D-Mediated Transphosphatidylation
Autor: Yamamoto, Yukihiro ; Hosokawa, Masashi ; Kurihara, Hideyuki ; Miyashita, Kazuo
Assuntos: Agriculture ; Apoptosis ; Aqueous system ; Arachis hypogaea ; Biological and medical sciences ; Biomaterials ; Biotechnology ; Brassica ; Chemicals ; Chemistry ; Chemistry and Materials Science ; Chromatography ; Fat industries ; Food industries ; Food Science ; Fundamental and applied biological sciences. Psychology ; Geraniol ; Industrial Chemistry/Chemical Engineering ; Ions ; NMR ; Nuclear magnetic resonance ; Original Paper ; phosphatidylation ; phosphatidylcholines ; Phospholipase D ; Phospholipid ; Proteins ; Solvents ; soybeans ; Staphylococcus infections ; Streptomyces chromofuscus ; Studies ; Terpene ; terpenoids ; Transphosphatidylation
É parte de: Journal of the American Oil Chemists' Society, 2008-04, Vol.85 (4), p.313-320
Notas: http://dx.doi.org/10.1007/s11746-008-1206-1
ObjectType-Article-1
SourceType-Scholarly Journals-1
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Descrição: Terpenes such as geraniol, geranylgeraniol, farnesol, and phytol are known as functional compounds which exhibit anticancer effects and activate nuclear receptors. For the application of functional terpenes in various fields, including the cosmetic and food industries, we attempted to synthesize phosphatidylated terpenes (terpene-PLs) by using phospholipase D (PLD). Transphosphatidylation of phosphatidylcholine with terpenes was carried out using PLD in a biphasic system containing ethyl acetate/water or in an aqueous system without organic solvent. The yield of terpene-PL increased with the reaction time and the amount of PLD in both the biphasic and aqueous systems. Further, the yield of terpene-PL in the aqueous system was higher than that in the biphasic system. In addition, among four PLDs from Streptomyces sp., Streptomyces chromofuscus, cabbage, and peanut, only the PLD from Streptomyces sp. could synthesize terpene-PL. The reaction yield, based on substrate phospholipid, of phosphatidylgeraniol reached 90 mol% under the following optimal reaction conditions: 50 μmol soyPC; 2,000 μmol geraniol; 1.6 U PLD; 0.8 ml of 0.2 M sodium acetate buffer (pH 5.6); temperature, 37 °C ; and reaction time, 24 h. The reaction yields of phosphatidylfarnesol, phosphatidylgeranylgeraniol, and phosphatidylphytol were 73, 54, and 17 mol%, respectively.
Editor: Berlin/Heidelberg: Berlin/Heidelberg : Springer-Verlag
Idioma: Inglês

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Preparation of Phosphatidylated Terpenes via Phospholipase D-Mediated Transphosphatidylation

Yamamoto, Yukihiro ; Hosokawa, Masashi ; Kurihara, Hideyuki ; Miyashita, Kazuo

Berlin/Heidelberg: Berlin/Heidelberg : Springer-Verlag

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