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Preparation of Phosphatidylated Terpenes via Phospholipase D‐Mediated Transphosphatidylation
Author(s) -
Yamamoto Yukihiro,
Hosokawa Masashi,
Kurihara Hideyuki,
Miyashita Kazuo
Publication year - 2008
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-008-1206-1
Subject(s) - terpene , geraniol , chemistry , farnesol , citronellol , aqueous solution , organic chemistry , solvent , phospholipase d , stereochemistry , chromatography , essential oil , enzyme
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.