Detoxification of 1,2-dihydroxy- 4-allylbenzene, a major phenolic compound in Piper betle, through glucuronidation using S9 protein of rat liver (Sprague Dawley)

Erryana Martati

Abstract


1,2-dihydroxy- 4-allylbenzene (DHAB) is a major compound in Piper betle leaf and also a metabolite of safrole metabolism. Epidemilogic studies showed people who have betel quid chewing habit are related to the incidence of oral submucous fibrosis and/or tumor formation. The aims of this research was to study the detoxification through the glucuronidation of DHAB using S9 protein of male rat liver  (Sprague Dawley) and a co-factor of uridin 5′-diphosphoglucuronide acid (UDPGA). The results showed that glucuronidation of DHAB using S9 protein of rat liver resulted two isomers of glucuronide metabolites due to the availibility of two active hydroxyl groups that one of them can bind glucuronide but not two of hydroxyl at the same time.


Keywords


1,2-dihydroxy- 4-allylbenzene, safrole, glucuronidation, S9 protein rat liver

Full Text:

PDF

References


Al-Malahmeh A.J., Alajlouni A.M, Ning J, Wesseling S, Vervoort J, Rietjens I.M.C.M., 2017, Determination and risk assessment of naturally occurring genotoxic and carcinogenic alkenylbenzenes in nutmeg-based plant food supplements. J Appl Toxicol. 37(10):1254-1264.

Al-Subeihi, A.A.A., Spenkelink, B., Rachmawati, N., Boersma, M.G., Punt, A., Vervoort, J., van Bladeren, P.J., Rietjens, I.M.C.M., 2011, Physiologically based biokinetic model of bioactivation and detoxification of the alkenylbenzene methyleugenol in rat. Toxicol. In Vitro 25, 267-285.

Amonkar, A.J., Padma P.R., Bhide, S.V., 1989, Protective effect of hydroxychavicol, a phenolic component of betel leaf, against the tobacco-specific carcinogens.

Berg, S.J.P.L., Punt, A., Soffers, A.E.M.F., Vervoort, J., Ngeleja, S., Spenkelink, B., Rietjens, I.M.C.M., 2012, Physiologically Based Kinetic Models for the Alkenylbenzene Elemicin in Rat and Human and Possible Implications for Risk Assessment. Chem. Res. Toxicol.

Berg S. J. P. L., Restani, P., Boersma M. G., Delmulle L, and Rietjens I. M. C. M. 2011. Levels of Genotoxic and Carcinogenic Compounds in Plant Food Supplements and Associated Risk Assessment. Food and Nutrition Sciences 2: 989-1010.

Chang M.C., Uang B.J, Wu H.L., Lee J.J, Hahn L.J, Jeng J.H. 2002. Inducing the cell cycle arrest and apoptosis of oral KB carcinoma cells by hydroxychavicol: roles of glutathione and reactive oxygen species. Br J Pharmacol.,135(3):619-30.

Chung, Y.T., Chen, C.L., Wu, C,C.,Chan, S.A.,Chi, C.W., and Liu, T.Y., 2008. Safrole-DNA adduct in hepatocellular carcinoma associated with betel quid chewing. Toxicology Letter. 183 (1-3), 21-27.

Fisher, M.B., Campanale, K., Ackermann, B.L., VandenBranden, M., Wrighton, S.A., 2000, In vitro glucuronidation using human liver microsomes and the pore-forming peptide alamethicin. Drug Metab. Dispos. 28, 560-566.

Hwang, L.S., Wang, C.K., Sheu, M.J., Kao, L.S., 1992, Phenolic Compounds of Piper betle Flower as Flavoring and Neuronal Activity Modulating Agents, In: Ho, C.T., Chang, Y.L., Huang, M.T. (Eds.) Phenolic Compounds in Food and Their Effects on Health I. American

Martati, E., Boersma, M.G., Spenkelink, A., Khadka, D.B., Punt, A., Vervoort, J., van Bladeren, P.J., Rietjens, I.M.C.M., 2011, Physiologically Based Biokinetic (PBBK) model for safrole bioactivation and detoxification in rats. Chem. Res. Toxicol. 24, 818-834.

Martati, E., Boersma, M.G., Spenkelink, A., Khadka, D.B., van Bladeren, P.J., Rietjens, I.M.C.M., Punt, A., 2012, Physiologically Based Biokinetic (PBBK) Modeling of Safrole Bioactivation and Detoxification in Humans as Compared With Rats. Toxicol. Sci. 128, 301-316.

Nakagawa, Y., Suzuki, T., Nakajima, K., Ishii, H., Ogata, A., 2009, Biotransformation and cytotoxic effects of hydroxychavicol, an intermediate of safrole metabolism, in isolated rat hepatocytes. Chem. Biol. Interact. 180, 89-97.

Periasamy, G., Karim, S., Gibrelibanos, M., Gebremedhin, G., Gilani, A.H., 2016, Nutmeg (Myristica fragrans Houtt.) Oils. In Preedy, V.R., Essential oil in Food Preservation, Flavor and Safety ,Elsevier, London UK, 607-613.

Punt, A., Freidig, A.P., Delatour, T., Scholz, G., Boersma, M.G., Schilter, B., van Bladeren, P.J., Rietjens, I.M.C.M., 2008, A physiologically based biokinetic (PBBK) model for estragole bioactivation and detoxification in rat. Toxicol. Appl. Pharmacol. 231, 248-259.

Rocha, L, Armando, L, Tietbohl, C. 2016, Staranise (Illicium verum Hook) Oil. In Preedy, V.R., Essential oil in Food Preservation, Flavor and Safety ,Elsevier, London UK, 751-756




DOI: http://dx.doi.org/10.12928/pharmaciana.v8i1.9194

Refbacks

  • There are currently no refbacks.


Copyright (c) 2018 Pharmaciana

Creative Commons License
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Pharmaciana indexed by:

Google ScholarDirectory of Open Access JournalIndonesian Scientific Journal Database (ISJD)Indonesian Publication Index (IPI)CrossrefBielefeld Academic Search Engine (BASE)Sherpa RomeoOpen Academic Journal Index (OAJI)

 

 

 

-----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Creative Commons License
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.