National Toxicology Program

11.0 ONLINE DATABASES AND SECONDARY REFERENCES

11.1 Online Databases

Chemical Information System Files

SANSS
TSCATS (Toxic Substances Control Act Test Submissions)

DIALOG Files

Chem. Econ. Hdbk.
NIOSHTIC
KIRK-OTHMER ENCYLOPEDIA OF CHEM. TECHNOL.

National Library of Medicine Databases

EMIC and EMICBACK (Environmental Mutagen Information Center)

STN International Files

AGRICOLA
BIOSIS
CA File
CABA
CANCERLIT
CAPLUS
CBNB
CEN
CHEMLIST
CROPB
CROPU
CSNB
DDFB
DDFU
DRUGLAUNCH
EMBASE
FSTA
HODOC
IPA
LIFESCI
MEDLINE
NAPRALERT
PHIN
PROMPT
RTECS
TOXLINE
TOXLIT

TOXLINE includes the following subfiles:

11.2 Secondary References

CRC Handbook of Chemistry and Physics, Weast, R.C., and M.J. Astle, Eds. CRC Press, Boca Raton, FL, 1980.

The Merck Index, 12^th ed., Budavari, S. Ed. Merck & Co., Inc., Whitehall, NJ. Listed in Section 12 as Budavari (1996).

12.0 REFERENCES

Abe, S. and T. Kaneda. 1975. Effect of betaines and taurine and its derivatives on plasma cholesterol levels in rats. Eiyo To Shokuryo 28(3):125-128. In Japanese (except abstract in English).

Anonymous. 1983. New hope for Parkinsonism. Chem. Week (27 April 1983):331.

Anthoni, U., C. Christophersen, L. Hougaard, and P. H. Nielsen. 1991. Review: Quaternary ammonium compounds in the biosphere-an example of a versatile adaptive strategy. Comp. Biochem. Physiol. 99B(1):1-18.

Beckstrom-Sternberg and J.A. Duke. 1997. Searches for plants containing trigonelline and biological activities of trigonelline. Phytochemeco Database produced by USDA Agricultural Research Service. Internet URL:http://sun.ars-grin.gov/cgi-bin/duke/ethnobot.pl.

Berglund, T. 1994. Nicotinamide, a missing link in the early stress response in eukaryotic cells: a hypothesis with special reference to oxidative stress in plants. FEBS Lett. 351:145-149.

Berglund, T., G. Kalbin, A. Strid, J. Rydström, A. B. Ohlsson. 1996. UV-B- and oxidative stress-induced increase in nicotinamide and trigonelline and inhibition of defensive metabolism induction by poly(ADP-ribose)polymerase inhibitor in plant tissue. FEBS Lett. 380:188-193.

Bodor, N. and H. H. Farag. 1983. Improved delivery through biological membranes. II. A redox chemical drug-delivery system and its use for brain-specific delivery of phenylethylamine. J. Med. Chem. 26:313-318.

Budavari, S. Ed. 1996. Trigonelline. In: The Merck Index. 12^th ed., Merck & Co., Inc., Whitehall, NJ. p. 1651.

Carter, E. G. A. and K. J. Carpenter. 1981. Trigonelline not a metabolite of bound niacin from cereals. Fed. Proc. 40:3II. No. 3604.

Chemlist. 1997. Database search for trigonelline. Chemlist Abstract No. 109540.

Chikhale, P. and N. Bodor. 1991. Improved delivery of acyclovir to the skin using a dihydrotrigonelline trigonelline redox carrier. J. Pharm. Sci. 80(4):402-403.

Czok, G. 1974. Biopharmacological effects of coffee substances other than caffeine. Arch. Sci. Med. 131(1):15-17.

Der Marderosian, A. H. 1977. Pharmacognosy: Medicinal teas-boon or bane? Drug Ther. 7 (Research Paper):178-186.

Faulkner, K. K. and J. W. H. Smith. 1950. Preliminary studies of the toxicity of locoweed extracts. Proc. Oklahoma Acad. Sci. 31:48-50.

Fung, V. A., T. P. Cameron, T. J. Hughes, P. E. Kirby, and V. C. Dunkel. 1988. Mutagenic activity of some coffee flavor ingredients. Mutat. Res. 204:219-228.

Gill, E. W., W. D. M. Paton, and R. G. Pertwee. 1970. Preliminary experiments on the chemistry and pharmacology of Cannabis. Nature (London) 228(Oct. 10):134-136.

Höhl, U., B. Upmeier, and W. Barz. 1988. Growth and nicotinate biotransformation in batch cultured and airlift fermenter grown soybean cell suspension cultures. Appl. Microbiol. Biotechnol. 28:319-323.

IARC (International Agency for Research on Cancer). 1991. Coffee,Tea, Mate, Methylxanthines, and Methylglyoxal. In: IARC Monographs on the Evaluation of the Carcinogenic Risks to Humans. Vol. 51:69.

Ito, Y., T. Suzuki, T. Shirai, and T. Hirano. 1994. Presence of cyclic betaines in fish. Comp. Biochem. Physiol. 199B(1):115-124.

Li, C. P. 1974. Chinese Herbal Medicine, NIH Pub. No. 75-732. U.S. Dept. of Health, Education, and Welfare, Washington, D.C.

Lynn, D. G., K. Nakanishi, S. L. Patt, J. L. Occolowitz, S. Almeida, and L. S. Evans. 1978. Isolation and characterization of the first mitotic cycle hormone that regulates cell proliferation. J. Am. Chem. Soc. 100:7759.

Mai, J. and H. Mai. 1997. Oral preparations containing fenugreek extracts for strengthening nail and hair. U.S Patent No. 95-541421 from CAPLUS 1997:351136.

Nakanishi, K. 1979. Studies on some biologically active compounds. Pure Appl. Chem. 51:731-745.

Palomino, E., D. Kessel, and J. P. Horwitz. 1989. A dihydropyridine carrier system for sustained delivery of 2,3-dideoxynucleosides to the brain. J. Med. Chem. 32:622-625.

Physicians' Desk Reference. 1995. Nicolar. pp. 1973-1975.

Pop, E., E. Shek, T. Murakami, and N. S. Bodor. 1989. Improved anticonvulsant activity of phenytoin by a redox brain delivery system I: Synthesis and some properties of the dihydropyridine derivatives. J. Pharm. Sci. 78(8):609-616.

Randall, K., M. Lever, B. A. Peddie, and S. T. Chambers. 1996. Accumulation of natural and synthetic betaines by a mammalian renal cell line. Biochem. Cell Biol. 74:283-287.

Reynard, A. M. 1968. The reversible and irreversible inhibition of N'-methylnicotinamide uptake into rat kidney cortex slices. J. Pharmacol. Exp. Ther. 163(2):461-467.

Roger, J.-C., D. G. Upshall, and J. E. Casida. 1969. Strucure-activity and metabolism studies on organophosphate teratogens and their alleviating agents in developing hen eggs with special emphasis on bidrin. Biochem. Pharmacol. 18:373-392.

Shani (Mishkinsky), J., A. Goldschmied, B. Joseph, Z. Ahronson, and F. G. Sulman. 1974. Hypoglycaemic effect of Trigonella Foenum Graecum [sic]and Lupinus Termis (Leguminosae) seeds and their major alkaloids in alloxan-diabetic and normal rats. Arch. Int. Pharmacodyn. 210:27-37.

Shibata, K. and H. Taguchi. 1987. Effect of dietary N'-methylnicotinamide or trigonelline on the growth and niacin metabolism in weanling rats. Vitamins 61(10):493-499. Abstract from CAPLUS 1988:36568.

Taguchi, H., M. Sakaguchi, and Y. Shimabayashi. 1985. Trigonelline content in coffee beans and the thermal conversion of trigonelline into nicotinic acid during the roasting of coffee beans. Agric. Biol. Chem. 49(12):3467-3472. Abstract from BIOSIS 86:238715.

Taguchi, H., M. Sakaguchi, and Y. Shimabayashi. 1986. Contents of quinolinic acid trigonelline and N-1 methylnicotinamide in various foods and thermal conversion of these compounds into nicotinic acid and nicotinamide. Vitamins 60(11):537-546. Abstract from BIOSIS 87:88133

Tramontano, W. A., P. A. McGinley, E. F. Ciancaglini, and L. S. Evans. 1986. A survey of trigonelline concentrations in dry seeds of the Dicotyledoneae. Environ. Exp. Bot. 26(3):197-205.

Tramontano, W. A., D. A. Phillips, C. A. Carman, and A. M. Massaro. 1990. Nuclear incorporation of [adenine¹⁴C]NAD is altered by compounds which affect poly(ADP-ribose) formation. Phytochemistry 29(1):31-33.

Viani, R. and I. Horman. 1974. Thermal behavior of trigonelline. J. Food Sci. 39(6):1216-1217.

Wasserman, G., H. D. Stahl, W. Rehman, and P. Whitman. 1993. Coffee. In: Kirk-Othmer Encyclopedia of Chemical Technology, 4^th ed., Vol. 6. John Wiley and Sons, New York.

Wu, X., K. Skog, and M. Jägerstad. 1997. Trigonelline, a naturally occurring constituent of green coffee beans behind the mutagenic activity of roasted coffee? Mutat. Res. 391:171-177.

Yuyama, S. and Y. Kawano. 1996. Urinary excretion of N'-methyl-2-pyridone-5-carboxylic acid and the fate of remaining of trigonelline. Adv. Exp. Med. Biol. 398:599-603.

Yuyama, S. and T. Suzuki. 1991. The excretion of N'-methyl-2-pyridone-5-carboxylic acid and related compounds in human subjects after oral administration of nicotinic acid, trigonelline, and N'-methyl-2-pyridone-5-carboxylic acid. Adv. Exp. Med. Biol. 294:475-479.

ACKNOWLEDGEMENTS

Support to the National Toxicology Program for the preparation of Trigonelline-Review of Toxicological Literature was provided by Integrated Laboratory Systems, Inc., through NIEHS Contract Number N01-ES-65402. Contributors included: Raymond R. Tice, Ph.D. (Principal Investigator); Bonnie L. Carson, M.S. (Co-Principal Investigator); Karen E. Haneke, M.S.; and Maria E. Donner, Ph.D.

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