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Synthesis of phosphatidylated-monoterpene alcohols catalyzed by phospholipase D and their antiproliferative effects on human cancer cells.

Bioorganic & medicinal chemistry letters (2008-06-17)
Yukihiro Yamamoto, Masashi Hosokawa, Hideyuki Kurihara, Takashi Maoka, Kazuo Miyashita
ABSTRACT

In order to prepare functional phospholipids in the medical and pharmaceutical fields, perillyl alcohol, myrtenol, and nerol were transphosphatidylated via phospholipase D in an aqueous system. The yields of phosphatidyl-perillyl alcohol, -myrtenol, and -nerol were 79 mol %, 87 mol %, and 91 mol %, respectively. The synthetic phosphatidylated monoterpenes showed a markedly antiproliferative effect on human prostate PC-3 and human leukemia HL-60 cells at 100 microM, while the free monoterpene alcohols had no effect at 400 microM.

MATERIALS
Product Number
Brand
Product Description

Supelco
Geraniol, analytical standard
Sigma-Aldrich
Geraniol, ≥97%, FCC, FG
Sigma-Aldrich
Geraniol, natural, ≥97%, FG
Sigma-Aldrich
Geraniol, 98%
Sigma-Aldrich
cis-3,7-Dimethyl-2,6-octadien-1-ol, 97%
Sigma-Aldrich
(S)-(−)-Perillyl alcohol, 96%
Sigma-Aldrich
(S)-(−)-Perillyl alcohol, ≥95%, FG
Sigma-Aldrich
cis-3,7-Dimethyl-2,6-octadien-1-ol, ≥97%, FCC, FG