Preparation of phosphatidylated terpenes via phospholipase D-mediated transphosphatidylation

JAOCS, Journal of the American Oil Chemists' Society

Volumn 85, Issue 4, 2008, Pages 313-320

  Yamamoto, Yukihiro ^a   Hosokawa, Masashi ^a   Kurihara, Hideyuki ^a   Miyashita, Kazuo ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Aqueous system; Geraniol; Phospholipase D; Phospholipid; Terpene; Transphosphatidylation

Indexed keywords

FOOD PRODUCTS; LIPASES; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

AQUEOUS SYSTEM; BIPHASIC SYSTEM; ETHYL ACETATE; PHOSPHATIDYLATED TERPENES;

PHOSPHOLIPIDS;

ARACHIS HYPOGAEA; BRASSICA OLERACEA VAR. CAPITATA; STREPTOMYCES; STREPTOMYCES CHROMOFUSCUS; STREPTOMYCES SP.;

EID: 40449134976     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-008-1206-1     Document Type: Article

References (27)

1. Lee SY, Hibi N, Yamane T, Shimizu S (1985) Phosphatidylglycerol synthesis by phospholipase D in a microporous membrane bioreactor. J Ferment Technol 63:37-44
2. Juneja LR, Hibi N, Yamane T, Shimizu S (1987) Repeated bath and continuous operations for phosphatidylglycerol synthesis from phosphatidylcholine with immobilized phospholipase D. Appl Microbiol Biotechnol 27:146-151
3. Juneja LR, Kazuoka T, Goto N, Yamane T, Shimizu S (1989) Conversion of phosphatidylcholine to phosphatidylserine by various phospholipases D in the presence of l- or d-serine. Biochim Biophys Acta 1003:277-283
4. Hosokawa M, Shimatani T, Kanada T, Inoue Y, Takahashi K (2000) Conversion to docosahexaenoic acid-containing phosphatidylserine from squid skin lecithin by phospholipase D-mediated transphosphatidylation. J Agric Food Chem 48:4550-4554
5. 2 catalyzed hydrolyses. Chem Phys Lipids 39:31-39
6. Juneja LR, Kazuoka T, Yamane T, Shimizu S (1988) Kinetic evaluation of conversion of phosphatidylcholine to phosphatidylethanolamine by phospholipase D from different sources. Biochim Biophys Acta 960:334-341
7. Nagao A, Ishida N, Terao J (1991) Synthesis of 6-phosphatidyl-l-ascorbic acid by phospholipase D. Lipids 26:390-394
8. Shuto S, Itoh H, Ueda S, Imamura S, Fukukawa K, Tsujino M, Matsuda A, Ueda T (1988) A facile enzymatic synthesis of 5′-(3-sn-phosphatidyl) nucleosides and their antileukemic activities. Chem Pharm Bull 36:209-217
9. Hossen M, Hernandez E (2004) Phospholipase D-catalyzed synthesis of novel phospholipid-phytosterol conjugates. Lipids 39:777-782
10. Shoff SM, Grummer M, Yatvin MB, Elson CE (1991) Concentration-dependent increase of murine P388 and B16 population doubling time by the acyclic monoterpene geraniol. Cancer Res 51:37-42
11. Yu SG, Hildebrandt LA, Elson CE (1995) Geraniol, an inhibitor of mevalonate biosynthesis, suppresses the growth of hepatomas and melanomas transplanted to rats and mice. J Nutr 125:2763-2767
12. Adany I, Yazlovitskaya EM, Haug JS, Voziyan PA, Melnykovych G (1994) Differences in sensitivity to farnesol toxicity between neoplastically- and non-neoplastically-derived cells in culture. Cancer Lett 79:175-179
13. McAnally JA, Jung M, Mo H (2003) Farnesyl-O-acetylhydroquinone and geranyl-O-acetylhydroquinone suppress the proliferation of murine B16 melanoma cells, human prostate and colon adenocarcinoma cells, human lung carcinoma cells, and human leukemia cells. Cancer Lett 202:181-192
14. Hierro I, Valero A, Pérez P, González P, Cabo MM, Montilla MP, Naverro MC (2004) Action of different monoterpenic compounds against Anisakis simplex s.l. L3 Larvae. Phytomedicine 11:77-82
15. Inoue Y, Shiraishi A, Hada T, Hirose K, Hamashima H, Shimada J (2004) The antibacterial effects of terpene alcohols on Staphylococcus aureus and their mode of action. FEMS Microbiol Lett 237:325-331
16. Ohizumi H, Masuda Y, Nakajo S, Sakai I, Ohsawa S, Nakaya K (1995) Geranylgeraniol is a potent inducer of apoptosis in tumor cells. J Biochem 117:11-13
17. Miquel K, Pradines A, Favre G (1996) Farnesol and geranylgeraniol induce actin cytoskeleton disorganization and apoptosis in A549 lung adenocarcinoma cells. Biochem Biophys Res Commun 225:869-876
18. Hiruma Y, Nakahama K, Fujita H, Morita I (2004) Vitamin K2 and geranylgeraniol, its side chain component, inhibited osteoclast formation in a different manner. Biochem Biophys Res Commun 314:24-30
19. Takahashi N, Kawada T, Goto T, Yamamoto T, Taimatsu A, Matsui N, Kimura K, Saito M, Hosokawa M, Miyashita K, Fushiki T (2002) Dual action of isoprenols from herbal medicines on both PPARγ and PPARα in 3T3-L1 adipocytes and HepG2 hepatocytes. FEBS Lett 514:315-322
20. Goto T, Takahashi N, Kato S, Egawa K, Ebisu S, Moriyama T, Fushiki T, Kawada T (2005) Phytol directly activates peroxisome proliferator-activated receptor α (PPARα) and regulates gene expression involved in lipid metabolism in PPARα-expressing HepG2 hepatocytes. Biochem Biophys Res Commun 337:440-445
21. Dittrich N, Ulbrich-Hofmann R (2001) Transphosphatidylation by immobilized phospholipase D in aqueous media. Biotechnol Appl Biochem 34:189-194
22. Iwasaki Y, Mizumoto Y, Okada T, Yamamoto T, Tsutsumi K, Yamane T (2003) An aqueous suspension system for phospholipase D-mediated synthesis of PS without toxic organic solvent. JAOCS 80:653-657
23. Dittmer JC, RL Lester (1964) A simple, specific spray for the detection of phospholipids on thin-layer chromatograms. J Lipid Res 7:126-127
24. Kokusho Y, Tsunoda A, Kato S, Machida H, Iwasaki S (1993) Production of various phosphatidylsaccharides by phospholipase D from Actinomadura sp. strain no. 362. Biosci Biotechnol Biochem 57:1302-1305
25. Takami M, Hidaka N, Suzuki Y (1994) Phospholipase D-catalyzed synthesis of phosphatidyl aromatic compounds. Biosci Biotechnol Biochem 58:2140-2144
26. Koketsu M, Nitoda T, Sugino H, Juneja LR, Kim M, Yamamoto T, Abe N, Kajimoto T, Wong CH (1997) Synthesis of a novel sialic acid derivative (sialylphospholipid) as an antirotaviral agent. J Med Chem 40:3332-3335
27. Ulbrich-Hofmann R, Lerchner A, Oblozinsky M, Bezakova L (2005) Phospholipase D and its application in biocatalysis. Biotechnol Lett 27:535-544