Dehydroepiandrosterone (1) was investigated for biotransformation studies using the plant cell suspension culture of Azadirachta indica A. Juss. for the first time, yielding metabolites 2–6: 5α,3,17-androstanedione (2), 5-androstene-3β,17β-diol (3), 3β-hydroxyandrostan-17-one (4), 3β,11α-dihydroxy-5-androsten-17-one (5), and 3β,7α-dihydroxy-5-androsten-17-one (6), whose structures were solved through modern spectroscopic methods. All five compounds 2–6 have not been reported obtained by this way before. This is a new method to biosynthesize compounds 2–6 employing cultured cells of A. indica. Metabolites 2, 3, and 6 are important biologically active compounds, whereas 4 is a precursor for the production of the 7-hydroxylated compound having antiglucocorticoid and neuroprotective effects.
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References
K. Ishihara, H. Hamada, T. Hirata, and N. Nakajima, J. Mol. Catal. B: Enzym., 23, 145 (2003).
F. DiCosmo and M. Misawa, Plant Cell Culture Secondary Metabolism Toward Industrial Application, CRC Inc., Florida, 1996.
P. Fernandes, A. Cruz, B. Angelova, H. M. Pinheiro, and J. M. S. Cabral, Enzym. Microb. Technol., 32, 688 (2003).
J. Dai, S. Zhang, J. Sakai, J. Bai, Y. Oku, and M. Ando, Tetrahedron Lett., 44, 1091 (2003).
A. Giri, V. Dhingra, C. C. Girib, A. Singh, O. P. Ward, and M. Lakshmi Narasu, Biotechnol. Adv., 19, 175 (2001).
T. Mukaiyama, T. Yamada, T. Nagata, and K. Imagawa, Chem. Lett., 327 (1993).
K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K. Jeong, H. Kwong, K. Morikawa, Z. Wang, D. Xu, and X. Zhang, J. Org. Chem., 57, 2768 (1992).
G. P. Stahly, S. Bates, M. C. Andres, and B. A. Cowans, Cryst. Growth Des., 6, 925 (2006).
Azizuddin, Saifullah, S. Khan, M. I. Choudhary, and Atta-ur-Rahman, Turk. J. Chem., 32, 141 (2008).
R. Aono and N. Doukyu, Biosci. Biotechnol. Biochem., 60, 1146 (1996).
Kohei, Y. Takara, and O. Hiroji, Kyoto-furitsu Ika Daigaku Zasshi, 97, 495 (1988).
R. R. Watson, DHEA in Human Health and Aging, CRC Press, 2011, 37 p.
S. Chalbot and R. Morfin, Drug Metab. Dispos., 33, 56 (2005).
A. Swizdor, T. Kolek, A. Panek, and A. Bialonska, Biochim. Biophys. Acta, Bioenerg., 1811, 253 (2011).
L. Richard, Steroids, 67, 967 (2002).
H. Li, H. M. Liu, W. Geb, L. Huang, and L. Shan, Steroids, 70, 970 (2005).
T. Murashige and F. Skoog, Physiol. Plant., 15, 473 (1962).
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Published in Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2013, pp. 576–580.
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Saifullah, Khan, S., Azizuddin et al. Potential of Azadirachta indica cell suspension culture to produce biologically active metabolites of dehydroepiandrosterone. Chem Nat Compd 49, 671–676 (2013). https://doi.org/10.1007/s10600-013-0704-z
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DOI: https://doi.org/10.1007/s10600-013-0704-z