Isoprenoid

DATA No : IIP0051 INFORMANT : Yoshichika Yoshioka

NAME : 3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol

COMMON NAME	:	Farnesol
SYMBOL	:	FOH
FORMULA	:	C₁₅H₂₆O MOL.WT (average) : 222.366

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BIOLOGICAL ACTIVITY

Farnesol inhibited growth of leukemia cells (CEM-C1) without causing cell lysis.(Ref. 0086) Farnesol inhibited phosphatidylcholine biosynthesis in cultured cells dy decreasing cholinephosphotransferase activity.(Ref. 0087) In HeLa cells farnesol caused translocation of PKC from membrane fraction to cytosol after 1hr of incubation and also prevented PMA-stimulated induction of PKC translocation from cytosol to membranes.(Ref. 0088)

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:

BOILING POINT	:	120 degree Celsius (at 0.2 mmHg)

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OPTICAL ROTATION	:

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SPECTRAL DATA

UV SPECTRA	:

IR SPECTRA	:

NMR SPECTRA	:	The 2H-labeled farnesol gave rise to 2H NMR powder patterns interpretable in terms of quadrupole splittings and splin-lattice relaxation times. Spin-lattice relaxation time measurements revealed high rates of motion for geraniol relative to cholesterol in similar membrane hosts and revealed correlation times close to the fatty acyl methyl termini in phosphatidylcholine.(Ref. 0038)

MASS SPECTRA	:

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

Pig liver(Ref. 0021).

CHEMICAL SYNTHESIS

METABOLISM

Incorporation of mevalonic acid-derived materials into proteins was studied with extremely halophilic archaebacteria, Halobacterium halobium and Halobacterium cutirubrum. The amount of farnesylated proteins was very small in H. halobium(Ref. 0089). The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capasity were as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and dolichol were not inhibitors(Ref. 0039).

GENETIC INFORMATION

NOTE

Tree dimansional structure(Ref. 0090).

REFERENCES

[0021]

AUTHOR	:	Mankowski, T., Jankowski, W., Chojnacki, T., and Franke, P.
TITLE	:	C55-Dolichol: occurrence in pig liver and preparation by hydrogenation of plant undecaprenol PubMed ID:1276128
JOURNAL	:	Biochemistry.
VOL	:	15 PAGE : 2125-2130 (1976)

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[0038]

AUTHOR	:	de Ropp, J. S., and Troy, F. A.
TITLE	:	2H NMR investigation of the organization and dynamics of polyisoprenols in membranes PubMed ID:4066690
JOURNAL	:	J Biol Chem.
VOL	:	260 PAGE : 15669-15674 (1985)

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[0039]

AUTHOR	:	Hinson, D. D., Chambliss, K. L., Toth, M. J., Tanaka, R. D., and Gibson, K. M.
TITLE	:	Post-translational regulation of mevalonate kinase by intermediates of the cholesterol and nonsterol isoprene biosynthetic pathways PubMed ID:9392419
JOURNAL	:	J Lipid Res.
VOL	:	38 PAGE : 2216-2223 (1997)

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[0086]

AUTHOR	:	Melnykovych, G., Haug, J. S., and Goldner, C. M.
TITLE	:	Growth inhibition of leukemia cell line CEM-C1 by farnesol: effects of phosphatidylcholine and diacylglycerol PubMed ID:1632790
JOURNAL	:	Biochem Biophys Res Commun.
VOL	:	186 PAGE : 543-548 (1992)

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[0087]

AUTHOR	:	Voziyan, P. A., Goldner, C. M., and Melnykovych, G.
TITLE	:	Farnesol inhibits phosphatidylcholine biosynthesis in cultured cells by decreasing cholinephosphotransferase activity PubMed ID:8240288
JOURNAL	:	Biochem J.
VOL	:	295 (Pt 3) PAGE : 757-762 (1993)

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[0088]

AUTHOR	:	Yazlovitskaya, E. M., and Melnykovych, G.
TITLE	:	Selective farnesol toxicity and translocation of protein kinase C in neoplastic HeLa-S3K and non-neoplastic CF-3 cells PubMed ID:7874691
JOURNAL	:	Cancer Lett.
VOL	:	88 PAGE : 179-183 (1995)

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[0089]

AUTHOR	:	Sagami, H., Kikuchi, A., Ogura, K., Fushihara, K., and Nishino, T.
TITLE	:	Novel isoprenoid modified proteins in Halobacteria PubMed ID:8093082
JOURNAL	:	Biochem Biophys Res Commun.
VOL	:	203 PAGE : 972-978 (1994)

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[0090]

AUTHOR	:	Murgolo, N. J., Patel, A., Stivala, S. S., and Wong, T. K.
TITLE	:	The conformation of dolichol PubMed ID:2706248
JOURNAL	:	Biochemistry.
VOL	:	28 PAGE : 253-260 (1989)

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