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

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.

• Authors: Yukihiro Yamamoto, Masashi Hosokawa, Hideyuki Kurihara, Takashi Maoka, Kazuo Miyashita
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 18 Issue 14 Pg. 4044-6 (Jul 15 2008) ISSN: 1464-3405 [Electronic] England
• PMID: 18556205 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Acyclic Monoterpenes
• Alcohols
• Antineoplastic Agents
• Bicyclic Monoterpenes
• Monoterpenes
• Terpenes
• perillyl alcohol
• myrtenal
• Phospholipase D
• geraniol

Topics

• Acyclic Monoterpenes
• Alcohols (chemistry)
• Antineoplastic Agents (pharmacology)
• Bicyclic Monoterpenes
• Catalysis
• Cell Line, Tumor
• Cell Proliferation
• Drug Screening Assays, Antitumor
• HL-60 Cells
• Humans
• Models, Chemical
• Monoterpenes (chemistry, pharmacology)
• Phospholipase D (chemistry)
• Terpenes (chemistry)