open access

https://hdl.handle.net/2115/44830

Synthesis of novel phospholipids that bind phenylalkanols and hydroquinone via phospholipase D-catalyzed transphosphatidylation

英語

Phenylalkanols

2011-01-31

Elsevier B.V.

New Biotechnology

28(1)

1-6

Phenylalkanols such as tyrosol and hydroxytyrosol (h-tyrosol), which possess antioxidant and anticancer properties, were phosphatidylated by phospholipase D (PLD)-catalyzed transphosphatidylation. After a 24-h reaction of phosphatidylcholine (PC) and tyrosol with PLD, a new product was detected by TLC and identified to phosphatidyl-tyrosol by high resolution MS and NMR analyses. The optimum reaction conditions were as follows; soyPC 50 μmol, tyrosol 500 μmol, ethyl acetate 1.6 ml, PLD 1.6 U, 0.2 M sodium acetate buffer (pH 5.6) 0.8 ml, 37℃ for 24 h. Under the optimum reaction conditions, the yields of phosphatidyl-tyrosol, hydroquinone (HQ), 2-(4-aminophenyl) ethanol (4APE), h-tyrosol, and 2-phenylethanol (PEA) were 87 ± 3.7, 13 ± 1.3, 90 ± 2.3, 64 ± 5.5 and 85 ± 1.0 mol%, respectively. Furthermore, from the results of transphosphatidylation of soyPC with several phenylethanols and phenylpropanols, we established the following details about the reaction specificity of transphosphatidylation by PLD from Streptomyces sp: (1) Para-amino and para-hydroxyl groups in the benzene ring of PEA derivatives do not affect the transphosphatidylation by PLD, whereas meta-hydroxyl group slightly inhibits the transphosphatidylation. (2) Meta and ortho-methyl groups in the benzene ring of PEA derivatives also slightly inhibit the transphosphatidylation. (3) Secondary and tertiary alcohols and hydroquinone are difficult to transphosphatidylate by PLD.

学術雑誌論文

Accepted Manuscript

1871-6784