Bioorganic & Medicinal Chemistry Letters 2008-07-15

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

Yukihiro Yamamoto, Masashi Hosokawa, Hideyuki Kurihara, Takashi Maoka, Kazuo Miyashita, Yukihiro Yamamoto, Masashi Hosokawa, Hideyuki Kurihara, Takashi Maoka, Kazuo Miyashita, Yukihiro Yamamoto, Masashi Hosokawa, Hideyuki Kurihara, Takashi Maoka, Kazuo Miyashita

Index: Bioorg. Med. Chem. Lett. 18 , 4044-6, (2008)

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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.