2
0
Chem. Res. Toxicol., Vol. 15, No. 1, 2002
Miyazawa et al.
(
(
(
14) Borghoff, S. J ., Short, B. G., and Swenberg, J . A. (1990) Biochemi-
cal mechanisms and pathobiology of R2u-globulin nephropathy.
Annu. Rev. Pharmacol. Toxicol. 30, 349-367.
15) Daniel, R., and Swenberg, J . A. (1991) The presence of R2u-
globulin is necessary for d-limonene promotion of male rat kidney
tumors. Cancer Res. 51, 3512-3521.
(31) Shimada, T., Yamazaki, H., Mimura, M., Inui, Y., and Guengerich,
F. P. (1994) Interindividual variations in human liver cytochrome
P-450 enzymes involved in the oxidation of drugs, carcinogens
and toxic chemicals: studies with liver microsomes of 30 J apanese
and 30 Caucasians. J . Pharmacol. Exp. Ther. 270, 414-423.
(32) Shimada, T., Nakamura, S., Imaoka, S., and Funae, Y. (1987)
16) Lock, E. A., Chabonneau, M., Strasser, J ., Swenberg, J . A., and
Bus, J . S. (1987) 2,2,2-Trimethylpentane-induced nephrotoxicity
II. The reversible binding of a TMP metabolite to a renal protein
fraction containing R2u-globulin. Toxicol. Appl. Pharmacol. 91,
1
Genotoxic and mutagenic activation of aflatoxin B by consitutive
forms of cytochrome P-450 in rat liver microsomes. Toxicol. Appl.
Pharmacol. 91, 13-21.
(33) Shimada, T., Misono, K. S., and Guengerich, F. P. (1986) Human
liver microsomal cytochrome P-450 mephenytoin 4-hydroxylase,
a prototype of genetic polymorphism in oxidative drug metabo-
lism. Purification and characterization of two similar forms
involved in the reaction. J . Biol. Chem. 261, 909-921.
(34) Yamazaki, H., Gillam, E. M. J ., Dong, M.-S., J ohnson, W. W.,
Guengerich, F. P., and Shimada, T. (1997) Reconstitution of
recombinant cytochrome P450 2C10 (2C9) and comparison with
cytochrome P450 3A4 and other forms: Effects of cytochrome
1
82-192.
(
17) Igimi, H., Nishimura, M., Kodama, R., and Ide, H. (1974) Studies
on the metabolism of d-limonene (p-mentha-1,8-diene) I. The
absorption, distribution and excretion of d-limonene in rats.
Xenobiotica 4, 77-84.
(
18) Regan, J . W., and Bjeldanes, L. F. (1976) Metabolism of (+)-
limonene in rats. J . Agric. Food Chem. 24, 377-380.
(
19) Kodama, R., Yano, T., Furukawa, K., Noda, K., and Ide, H. (1976)
Studies on the metabolism of d-limonene (p-mentha-1,8-diene).
IV. Isolation and characterization of new metabolites and species
differences in metabolism. Xenobiotica 6, 377-389.
P450-P450 and cytochrome P450-b
Biophys. 342, 329-337.
5
interactions. Arch. Biochem.
(35) Shimada, T., and Yamazaki, H. (1998) Cytochrome P450 recon-
stitution systems. In Methods in Molecular Biology (Phillips, I.
R., and Shephard, E. A., Eds.) pp 85-93, Humana Press, Totowa,
NJ .
(36) Omura, T., and Sato, R. (1964) The carbon monoxide-binding
pigment of liver microsomes. I. Evidence for its hemoprotein
nature. J . Biol. Chem. 239, 2370-2378.
(37) Lowry, O. H., Rosebrough, N. J ., Farr, A. L., and Randall, R. J .
(1951) Protein measurement with the Folin phenol reagent. J .
Biol. Chem. 193, 265-275.
(38) Komatsu, K., Ito, K., Nakajima, Y., Kanamitsu, S., Imaoka, S.,
Funae, Y., Green, C. E., Tyson, C. A., Shimada, N., and Sugiyama,
Y. (2000) Prediction of in vivo drug-drug interactions between
tolbutamide and various sulfonamides in humans based on in
vitro experiments. Drug Metab. Dispos. 28, 475-481.
(39) Imaoka, S., Fujita, S., and Funae, Y. (1991) Age-dependent
expression of cytochrome P-450s in rat liver. Biochim. Biophys.
Acta 1097, 187-192.
(40) Ryan, D. E., and Levin, W. (1990) Purification and characteriza-
tion of hepatic microsomal cytochrome P-450. Pharmacol. Ther.
45, 153-239.
(41) Dietrich, D. R., and Swenberg, J . A. (1991) NCI-Black-Reiter
(NBR) male rats fail to develop renal disease following exposure
to agents that induce R2u-globulin (R2u) nephropathy. Fundam.
Appl. Toxicol. 16, 749-762.
(
(
(
20) Watabe, T., Hiratsuka, A., Ozawa, N., and Isobe, M. (1981) A
comparative study on the metabolism of d-limonene and 4-vinyl-
cyclohex-1-ene by hepatic microsomes. Xenobiotica 11, 333-344.
21) Kodama, R., Noda, K., and Ide, H. (1974) Studies on the
metabolism of d-limonene (p-mentha-1,8-diene) II. The metabolic
fate of d-limonene in rabbits. Xenobiotica 4, 85-95.
22) J ager, W., Mayer, M., Platzer, P., Rezicek, G., Dietrich, H., and
Buchbauer, G. (1999) Stereoselective metabolism of the mono-
terpene carvone by rat and human liver microsomes. J . Pharm.
Pharmacol. 52, 191-197.
(
(
(
(
(
(
(
(
23) Watabe, T., Hiratsuka, A., Isobe, M., and Ozawa, N. (1980)
Metabolism of d-limonene by hepatic microsomes to nonmutagenic
epoxides toward Salmonella typhimurium. Biochem. Pharmacol.
2
9, 1068-1071.
24) Yamazaki, H., and Shimada, T. (1998) Formation in vitro of an
2
+
inhibitory cytochrome P450‚Fe -metabolite complex with roxithro-
mycin and its decladinosyl, O-dealkyl, and N-demethyl metabo-
lites in rat liver microsomes. Xenobiotica 28, 995-1004.
25) Miyazawa, M., Shindo, M., and Shimada, T. (2001) Oxidation of
1
,8-cineole, the monoterpene cyclic ether originated from Euca-
lyptus polybractea, by cytochrome P450 3A enzymes in rat and
human liver microsomes. Drug Metab. Dispos. 29, 200-205.
26) Shimada, T., Tsumura, F., Yamazaki, H., Guengerich, F. P., and
Inoue, K. (2001) Characterization of (()-bufuralol hydroxylation
activities in liver microsomes of J apanese and Caucasian subjects
genotyped for CYP2D6. Pharmacogenetics 11, 143-156.
27) Shimada, T., Tsumura, F., and Yamazaki, H. (1999) Prediction
of human liver microsomal oxidations of 7-ethoxycoumarin and
chlorzoxazone using kinetic parameters of recombinant cyto-
chrome P450 enzymes. Drug Metab. Dispos. 27, 1274-1280.
28) Mimura, M., Yamazaki, H., Sugahara, C., Hiroi, T., Funae, Y.,
and Shimada, T. (1994) Differential roles of cytochromes P450
(42) Lehman-Mckeeman, L. D., and Caudill, D. (1994) d-Limonene
induced Hyaline droplet nephropathy in R2u-globulin transgenic
mice. Fundam. Appl. Toxicol. 23, 562-568.
(43) EI-Bayoumy, K. (1994) Evaluation of chemopreventive agents
against breast cancer and proposed strategies for future clinical
intervention trials. Carcinogenesis 15, 2395-2420.
(
(
(
44) Crowell, P. L., Kennan, W. S., Haag, J . D., Ahmad, S., Vedejs,
E., and Gould, M. N. (1992) Chemoprevention of mammary
carcinogenesis by hydroxylated derivatives of d-limonene. Car-
cinogenesis 13, 1261-1264.
45) Ariyoshi, T., Araki, M., Ideguchi, K., and Ishizuka, Y. (1975)
Studies on the metabolism of d-Limonene (p-Mentha-1,8-diene).
III. Effects of d-limonene on the lipids and drug-metabolizing
enzymes in rat livers. Xenobiotica 5, 33-38.
2
D1, 2C11, and 1A1/2 in the hydroxylation of bufuralol by rat
liver microsomes. Biochem. Pharmacol. 47, 1957-1963.
29) Yamazaki, H., Hiroki, S., Urano, T., Inoue, K., and Shimada, T.
(1996) Effects of roxithromycin, erythromycin and troleandomycin
on their N-demethylation by rat and human cytochrome P450
enzymes. Xenobiotica 26, 1143-1153.
30) Shimada, T., and Nakamura, S. (1987) Cytochrome P-450-
mediated activation of procarcinogens and promutagens to DNA-
damaging products by measuring expression of umu gene in
Salmonella typhimurium TA1535/pSK1002. Biochem. Pharmacol.
46) Guengerich, F. P., and Liebler, D. C. (1985) Enzymatic activation
of chemicals to toxic metabolites. CRC Crit. Rev. Toxicol. 14,
2
59-307.
3
6, 1979-1987.
TX0155350