Synthesis of phosphatidylated-monoterpene alcohols catalyzed by phospholipase D and their antiproliferative effects on human cancer cells.
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.
Yamamoto
Yukihiro
Y
Faculty of Fisheries Sciences, Hokkaido University, 3-1-1 Minato, Hakodate, Hokkaido 041-8611, Japan.
Hosokawa
Masashi
M
Kurihara
Hideyuki
H
Maoka
Takashi
T
Miyashita
Kazuo
K
D000080462:Acyclic Monoterpenes; D000438:Alcohols / Q000737:chemistry; D000970:Antineoplastic Agents / Q000494:pharmacology*; D000081008:Bicyclic Monoterpenes; D002384:Catalysis; D045744:Cell Line, Tumor; D049109:Cell Proliferation; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006801:Humans; D008956:Models, Chemical; D039821:Monoterpenes / Q000737:chemistry / Q000494:pharmacology; D010739:Phospholipase D / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry
D000080462:Acyclic Monoterpenes; D000438:Alcohols; D000970:Antineoplastic Agents; D000081008:Bicyclic Monoterpenes; D039821:Monoterpenes; D013729:Terpenes; C032208:perillyl alcohol; C061545:myrtenal; D010739:Phospholipase D; C007836:geraniol