The carcinogenic effects of benzoquinones produced by the flour beetle

• Autorzy: Lis L. , Bakula T. , Baranowski M. , Czarnewicz A.
• Języki publikacji: EN

Abstrakty

EN

Humans and animals come into contact with various compounds in their natural environment. Most of the encountered substances are neutral, yet some may carry adverse health effects. The ingested food may be a source of harmful substances, including benzoquinones which, as shown by research results cited in this paper, demonstrate toxic, carcinogenic and enterotoxic activity. This group of compounds is inclusive of 2-methyl-1,4-benzoquinone (MBQ) and 2-ethyl-1,4-benzoquinone (EBQ), defensive secretions of the confused flour beetle (Tribolium confusum J. du V) and the red flour beetle (Tribolium castaneum Herbst). Benzoquinones have a carcinogenic effect, they are inhibitors of growth of various microorganisms, they produce a self-defense mechanism in threat situations and affect population aggregation. As noted by the referenced authors, the properties of benzoquinones have not been fully researched to this date.

Słowa kluczowe

EN

beetle; benzoquinone; carcinogenic effect; enterotoxic activity; enterotoxin; flour beetle; healthy effect; 2-methyl-1,4 benzoquinone; 2-ethyl-1,4 benzoquinone; Tribolium confusum; red flour beetle; Tribolium castaneum

• Wydawca: -
• Czasopismo: Polish Journal of Veterinary Sciences
• Rocznik: 2011
• Tom: 14
• Numer: 1
• Opis fizyczny: p.159-164,ref.

Twórcy

autor

Lis L.

• Department of Veterinary Prevention and Feed Hygiene, Faculty of Veterinary Medicine, University of Warmia and Mazury in Olsztyn, Oczapowskiego 13, 10-718 Olsztyn, Poland

autor

Bakula T.

autor

Baranowski M.

autor

Czarnewicz A.

Bibliografia

• Roth LM, Howland RB (1941) Studies on the gaseous secretion of Tribolium confusum Duval. I. Abnormaliteies produced in Tribolium confusum Duval by exposure to a secretion given off by the adults. Ann Entomol Soc Am 34: 151-175.
• Alexander P, Barton DHR (1943) The excretion of ethylquinone by the Flour Beetle. Biochem J 37: 463-465.
• Loconti JD, Roth LM (1953) Composition of the odorous secretion of Tribolium castaneum. Ann Entomol Soc Am 46: 281-289.
• Engelhardt M, Rapoport H, Sokoloff A (1965) Odorous Secretion of Normal and Mutant Tribolium confusum. Science 150: 632-633.
• Ladisch RK, Suter MA (1967) Affinity of Tetritoxin to Animal Protein. Proc Penn Acad Sci 41: 206-212.
• Blum MS (1978) Biochemical defenses of insects. In: Rockstein M (ed) Biochemistry of insects. Academic Press, London, pp 465-513.
• Howard RW (1987) Chemosystematic studies of the Triboliini (Coleoptera: Tenebrionidae): phylogenetic inferences from the defensive chemicals of eight Tribolium spp., Palorus ratzeburgi (Wissmann), and Latheticus oryzae Waterhouse. Ann Entomol Soc Am 80: 398-405.
• Omaye ST, Wirtz RA, Fruin JT (1981) Toxicity of substituted p-benzoquinones found in the secretion of tenebrionid flour beetles. Proc West Pharmacol Soc 24: 169-171.
• Ladisch RK, Mcque B (1953) Methods of obtaining quinones from flour beetles. Science 118: 324-325.
• Yezerski A, Gilmor TP, Stevens L (2000) Variation in the production and distribution of substituted benzoquinone compounds among genetic strains of the confused flour beetle, Tribolium confusum. Physiol Biochem Zool 73: 192-199.
• Yezerski A, Gilmor TP, Stevens L (2004) Genetic analysis of benzoquinone production in Tribolium confusum. J Chem Ecol 30: 1035-1044.
• Payne NM (1925) Some effects of Tribolium on flour. J Econ Entomol 18: 737-744.
• Roth LM (1943) Studies on the gaseous secretion of Tribolium confusum Duval. II. The odoriferous glands of Tribolium confusum. Ann Entomol Soc Am 36: 397-424.
• Von Endt DW, Wheeler JW (1971) I-Pentadecene production in Tribolium confusum. Science 172: 60-61.
• Pappas PW, Morrison SE (1995) Benzoquinones of the beetles, Tribolium castaneum and Tribolium confusum. Prep Biochem 25: 155-168.
• Pappas PW, Wardrop SM (1996) Quantification of benzoquinones in the flour beetles, Tribolium castaneum and Tribolium confusum. Prep Biochem Biotechnol 26: 53-66.
• IARC (1999) Monographs on the evaluation of the carcinogenic risk of chemicals to man. Lyon 71: 1245-1250.
• IARC (1977) Monographs on the evaluation of the carcinogenic risk of chemicals to man. Some fumigants, the herbicides 2,4-D and 2,4,5-T, chlorinated dibenzodioxins and miscellaneous industrial chemicals. Lyon 15: 255-264.
• Monks TJ, Jones DC (2002) The metabolism and toxicity of quinones, quinonimines, quinone methides, and quinone-thioethers. Curr Drug Metab 3: 425-438.
• Post GB, Snyder R, Kalf GF (1985) Inhibition of RNA synthesis and interleukin-2 production in lymphocytes in vitro by benzene and its metabolites, hydroquinone and p- benzoquinone. Toxicol Lett 29: 161-167.
• Post GB, Snyder R, Kalf GF (1984) Inhibition of mRNA synthesis in rabbit bone marrow nuclei in vitro by quinone metabolites of benzene. Chem Biol Interact 50: 203-211.
• Post GB, Snyder R, Kalf GF (1986) Metabolism of benzene and phenol in macrophages in vitro and the inhibition of RNA synthesis by benzene metabolites. Cell Biol Toxicol 2: 231-246.
• D’Odorico A, Sturniolo GC, Bilton RF, Morris AI, Gilmore IT, Naccarato R (1997) Quinone-induced DNA single strand breaks in a human colon carcinoma cell line. Carcinogenesis 18: 43-46.
• Souček P (1999) Cytochrome P450 destruction by quinines: comparison of effects in rat and human liver microsomes. Chem Biol Interact 121: 223-236.
• Souček P, Ivan G, Stopka P (2000) Effect of the microsomal system on interconversions between hydroquinone, benzoquinone, oxygen activation, and lipid peroxidation. Chem Biol Interact 126: 45-61.
• Zhongwen X, Yangbin Z, Guliaev AB, Huiyun S, Bo Hang, Singer B, Zhigang W (2005) The p-benzoquinone DNA adducts derived from benzene are highly mutagenic. DNA Repair 4: 1399-1409.
• Kondrová E, Stopka P, Souček P (2007) Cytochrome P450 destruction by benzene metabolites 1,4-benzoquinone and 1,4-hydroquinone and the formation of hydroxyl radicals in minipig liver microsomes. Toxicol In Vitro 21: 566-575.
• Yezerski A, Ciccone C, Rozitski J, Volingavage B (2007) The Effects of a Naturally Produced Benzoquinone on Microbes Common to Flour. J Chem Ecol 33: 1217-1225.
• Yezerski A, Cussatt G, Glick D, Evancho M (2005) The effects of the presence of stored product pests on the microfauna of a flour community. J Appl Microbiol 98: 507-515.
• Takizawa N (1940) Über die experimentelle erzengung der haunt-med lungenkrebse ber der mark durch bapinselung mit chinone. Gann 34: 158-160.
• Takizawa N (1941) Uber die wucherung des epithels deslLungengervebes bei maus durch die bepinselung von chinone. Beitrage zur Histogenese des Lungenkrebses. Gann 35: 327-330.
• Takizawa N, Sugischita M (1948) Cancerogenic action of quinone on skin and lung tissue of the mouse. Gann 39: 56-57.
• Sugischita M (1950) Experiments in the production of skin and lung cancer in the mouse by means of unreduced quinone. Gann 41: 125-127.
• Tiedemann H (1953) Wirkt p-Benzochinon bei lokaler Auwendung cancerogen? Z Naturforsch 8: 49-50.
• Kishizawa F (1954) Carcinogenic action of para-benzoquinone on the lung of mice by the experimental inhalation. Gann 45: 389-391.
• Kishizawa F (1955) Carcinogenic action of para-benzoquinone on the lung of mice by the experimental inhalation. Gann 46: 359-361.
• Kishizawa F (1956) Carcinogenic action of para-benzoquinone on the lung of mice by the experimental inhalation. Gann 47: 601-603.
• Umeda M (1957) Production of rat sarcoma by injections of propylene glycol solution of p-quinone. Gann 48: 139-144.
• Ladisch RK (1963) Isolation and characterization of certain insect secretions. Proc Penn Acad Sci 37: 127-136.
• Ladisch RK (1964) Quinone toxins and allied synthetics car-cinogenesis. Proc Penn Acad Sci 38: 144-149.
• Ladisch RK (1965a) Assay of Tetritoxin in flour beetles tribolium and method of detecting the toxin on cereal foods. Proc Penn Acad Sci 39: 36-41.
• Ladisch RK (1965b) Tetritoxin: binding with amino acids and proteins. Proc Penn Acad Sci 39: 48-56.
• Ladisch RK, Suter MA (1965) Tetritoxin: synthesis and toxicity rating. Proc Penn Acad Sci 39: 42-47.
• Suter MA, Ladisch RK (1963) Toxicity of insect quinones to mice. Proc Penn Acad Sci 37: 137-141.
• Ladisch RK, Ladisch SK, Howe PM (1967) Quinoid secretions in grain and flour beetles. Nature 215: 939-940.
• Ladisch RK, Suter MA, Froio GF (1968) Sweat gland carcinoma produced in mice by insect quinones. Proc Penn Acad Sci 42: 87-91.
• Shimkin MB, Gruenstein M, Meranze DR (1971) Test for carcinogenic activity of benzoquinones in long-evans rats. Cancer Res 31: 957-959.
• El-Mofty MM, Osman SI, Sakr SA, Toulan BA (1988) Car-cinogenicity of flour infested with Tribolium castaneum using the Egyptian toad Bufo regularis as a biological test animal. Oncology 45: 65-67.
• El-Mofty MM, Sakr SA, Osman SI, Toulan BA (1989) Carcinogenic effect of biscuits made of flour infested tribolium castaneum in bufo regularis. Oncology 46: 63-65.
• El-Mofty MM, Khudoley VV, Sakr SA, Fathala NG (1992) Flour infested with Tribolium castaneum, biscuits made of this flour, and 1,4-benzoquinone induce neoplastic lesions in Swiss Albino mice. Nutr Cancer 17: 97-104.
• Elhassaneen YA, El-Moaty AA Abd (2003) Blood oxidant and antioxidant status in rats feeding with insect-infested wheat flour. Pak J Biol Sci 6: 1354-1360.