Abstract
Bacillus stearothermophilus, a thermophilic bacterium isolated from Kuwaiti desert, when incubated with exogenous progesterone for 10 days at 65°C produced two monohydroxylated, two dihydroxy isomers of progesterone and a B-Seco compound. These metabolites were purified by TLC and HPLC followed by their identification through 1H, 13C NMR and other spectroscopic data. Microbial hydroxylation of 17β-estradiol resulted in the production of estrone. The effect of some inducers resulted in the production of two metabolites from 17β-estradiol one of which was identified as 3,6β,17β-trihydroxyestra-1,3,5,14(10)-tetrene and the other metabolite remained unidentified. The transformation products were identified through their spectral data and comparison with reference to compounds. Antioxidant activities of progesterone transformed mixture and purified metabolites of 17β-estradiol were studied by linoleic acid/β-carotene assay. An enhanced antioxidant activity for progesterone transformation products was observed, when compared to progesterone. A comparison of antioxidant activity of progesterone and 17β-estradiol transformation products is reported.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Yoshishige U, Yoshito I, Hiroaki M, Shinji G, Takehiko K, Junji Y, Satoshi I, Takahito K (2006) 17β-Estradiol protects against oxidative stress-induced cell death through the glutathione/glutaredoxin-dependent redox regulation of Akt in myocardiac H9c2 cells. J Biol Chem 218(19):13092–13102
Finkel T, Holbrook NJ (2000) Oxidants, oxidative stress and the biology of aging. Nature 408:239–247
Yang SH, Liu R, Perez EJ, Wen Y, Stevens SM Jr, Valencia T, Brun-Zinkernagel AM, Prokai L, Will Y, Dykens J, Koulen P, Simpkins JW (2004) Mitochondrial localization of estrogen receptors β. Proc Natl Acad Sci U S A 101:4130–4135
Noriko S, Kenji T, Masahiro A, Junya A, Masayoshi H, Katsuya I, Seungbum K, Yi-Qiang L, Yumiko O, Tokumitsu W, Ieharu Y, Masao Y, Masato E, Yasuyoshi O (2001) Estrogen prevents oxidative stress–induced endothelial cell apoptosis in rats. Circulation 103:724–731
Baba T, Shimizu T, Suzuki Y, Ogawara M, Isono K, Koseki H, Kurosawa H, Shirakawa T (2005) Estrogen, insulin, and dietary signals cooperatively regulate longevity signals to enhance resistance to oxidative stress in mice. J Biol Chem 280:16417–16426
Yan L, Ji Z, Yan L, Xiao-Song G (2002) Protective effect of estradiol on hepatocytic oxidative damage. Gastroenterology 8(2):363–366
Kuhl H (1994) Cardiovascular effects and estrogen/gestagen substitution therapy. Ther Umsch 51:748–754
Al-Awadi S, Afzal M, Oommen S (2001) Studies on Bacillus stearothermophilus. Part 1. Transformation of progesterone to a new metabolite 9,10-seco-4-pregnene-3,9,20-trione. J Steroid Biochem Mol Biol 78(5):493–498
Al-Awadi S, Afzal M, Oommen S (2002) Studies on Bacillus stearothermophilus. Part II. Transformation of progesterone. J Steroid Biochem Mol Biol 82(2–3):251–256
Al-Awadi S, Afzal M, Oommen S (2003) Studies on Bacillus stearothermophilus. Part III. Transformation of testosterone. Appl Microbiol Biotechnol 62:48–52
Vga M, Castillo T, Retamales I, Heras JL, Devoto L, Videla LA (1994) Steroidogenic capacity and oxidative stress-related parameters in human luteal cell regression. Free Radic Biol Med 17(6):493–499
Gupta S, Agarwal A, Krajcir N, Alvarez JG (2006) Role of oxidative stress in endometriosis. Reprod Biomed 13(1):126–134
Acknowledgement
This work was supported by a Kuwait University grant # SB040 and SL02/02 for which the authors are thankful.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2010 Humana Press, a part of Springer Science+Business Media, LLC
About this protocol
Cite this protocol
Afzal, M., Al-Awadi, S., Oommen, S. (2010). Antioxidant Activity of Biotransformed Sex Hormones Facilitated by Bacillus Stearothermophilus . In: Armstrong, D. (eds) Advanced Protocols in Oxidative Stress II. Methods in Molecular Biology, vol 594. Humana Press, Totowa, NJ. https://doi.org/10.1007/978-1-60761-411-1_25
Download citation
DOI: https://doi.org/10.1007/978-1-60761-411-1_25
Published:
Publisher Name: Humana Press, Totowa, NJ
Print ISBN: 978-1-60761-410-4
Online ISBN: 978-1-60761-411-1
eBook Packages: Springer Protocols