Abstract
The biotransformation potential of cell suspension cultures generated from Withania somnifera leaf was investigated, using withanolides, i.e. withanolide A, withaferin A, and withanone as precursor substrates. Interestingly, the cell suspension cultures showed inter-conversion of withanolides, as well converted to some unknown compounds, released to the culture media. The bio-catalyzed withanolide was detected and quantified by TLC and HPLC, respectively. There is noticeable conversion of withanolide A to withanone, and vice versa though at a lower level. The type of reaction of this biotransformation appears to be substitution of 20-OH group to 17-OH in withanolide A. In this paper, we present for the first time the possibility of biotransformation by inter-conversion of withanolides of pharmacological importance through cell suspension culture of W. somnifera. The possible role of putative cytochrome P450 hydroxylases is implicated in the conversion.
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References
Anjaneyulu ASR, Rao DS (1997) A new withanolides from the leaves of Withania somnifera. Indian J Chem 36:161–165
Chaurasiya ND, Uniyal GC, Lal P, Misra L, Sangwan NS, Tuli R, Sangwan RS (2007) Analysis of withanolides in root and leaf of Withania somnifera by HPLC with photodiode array and evaporative light scattering detection. Phytochem Anal 19:148–154
Choudhary MI, Hussain S, Yousuf S, Dar A, Mudassar, Atta-ur-Rahmana (2005) Chlorinated and diepoxy withanolides from Withania somnifera and their cytotoxic effects against human lung cancer cell line. Phytochemistry 71:2205–2209
Devi PU, Sharada AC, Solomon FE, Kamath MS (1992) In vivo growth inhibitory effect of Withania somnifera (Ashwagandha) on a transplantable mouse tumor sarcoma 180. Indian J Exp Biol 30:169–172
Funska JA, Khandlova M, Sturdíkova JP, Rosazza, Kieslich K (1985) Biotransformation of withaferin-A by a culture of Arthrobacter simplex. Folia Microbiol 30:427–432
Jayaprakasam B, Zhang Y, Seeram NP, Nair MG (2003) Growth inhibition of human tumor cell lines by withanolides from Withania somnifera leaves. Life Sci 74:125–132
Kaileh M, Berghe WV, Heyerick A et al (2007) Withaferin A strongly elicits IKKβ hyperphosphorylation, concomitant with potent inhibition of its kinase activity. J Biol Chem 282:4253–4264
Kinghorn AD, Su BN, Jang DS, Chang LC, Lee D, Gu J-Q, Carcanche-Blanco EJ, Pawlus AD, Lee SK, Park EJ, Cuendet M, Gills JJ, Bhat K, Park H-S, Mata-Greenwood E, Song LL, Jang M, Pezzuto J (2004) Natural inhibitors of carcinogenesis. Planta Med 70:691–705
Kuboyama T, Tohda C, Komatsu K (2005) Neuritic regeneration and synaptic reconstruction induced by withanolide A. Br J Pharmacol 144:961–971
Matsuda H, Murakami T, Kishi A, Yoshikawa M (2001) Structures of withanosides I, II, III, IV, V, VI, and VII, new withanolide glycosides, from the roots of Indian Withania somnifera Dunal and inhibitory activity for tachyphylaxis to clonidine in isolated guinea-pig ileum. Bioorg Med Chem 9:1499–1507
Misra LN, Lal P, Chaurasiya ND, Sangwan RS, Sinha S, Tuli R (2008) Steroid Selective reactivity of 2-mercaptoethanol with 5β,6β-epoxide in steroids from Withania somnifera. Steroids 73:245–251
Sabir F, Sangwan NS, Chaurasiya ND, Misra LN, Sangwan RS (2008) In vitro withanolide production by Withania somnifera L. cultures. Z Naturfor 63c:409–413
Sangwan RS, Agarwal K, Luthra R et al (1993) Biotransformation of arteannuic acid into arteannuin-B and artemisinin in Artemisia annua. Phytochemistry 34:1301–1302
Sangwan RS, Chaurasiya ND, Misra LN, Lal P, Uniyal GC, Sharma R, Sangwan NS, Suri KA, Qazi GN, Tuli R (2004) Phytochemical variability in commercial herbal products and preparations of Withania somnifera (Ashwagandha). Curr Sci 86:461–465
Sangwan RS, Chaurasiya ND, Misra LN, Lal P, Uniyal GC, Sangwan NS, Srivastava AK, Suri KA, Qazi GN, Tuli R (2005) An improved process for isolation of withaferin-A from plant materials and products therefrom. US Patent # 7,108, 870
Sangwan RS, Chaurasiya ND, Lal P, Misra L, Uniyal GC, Tuli R, Sangwan NS (2007) Withanolide A biogeneration in in vitro shoot cultures of Ashwagandha (Withania somnifera Dunal), a main medicinal plant of Ayurveda. Chem Pharm Bull 55:1371–1375
Sangwan RS, Chaurasiya ND, Lal P, Misra L, Tuli R, Sangwan NS (2008) Root-contained withanolide A is inherently de novo synthesized within roots in Ashwagandha (Withania somnifera). Physiol Plant 133:278–287
Singh B, Chandan BK, Gupta DK (2003) Adaptogenic activity of a novel withanolide free aqueous fraction from the roots of Withania somnifera Dunal. Phytother Res 17:531–536
Su B-N, Gu J-Q, Kang Y-H, Park E-J, Pezzuto JM, Kinghorn AD (2004) Induction of the phase II enzyme, quinone reductase, by withanolides and norwithanolides from solanaceous species. Mini-Rev Org Chem 1:115–123
Zhao J, Nakamura N, Hattori M, Kuboyama T, Tohda C, Komatsu K (2002) Withanolide derivatives from the roots of Withania somnifera and their neurite outgrowth activities. Chem Pharmaceut Bull 50:760—765
Acknowledgments
The authors at CIMAP are thankful to the Director, CIMAP, for providing the necessary facilities and encouragement. The financial grant NWP-09 Program of CSIR, Government of India, New Delhi is gratefully acknowledged. F.S. and J.S. are grateful to CSIR, New Delhi for the award of senior and junior research fellowships, respectively.
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Sabir, F., Sangwan, R.S., Singh, J. et al. Biotransformation of withanolides by cell suspension cultures of Withania somnifera (Dunal). Plant Biotechnol Rep 5, 127–134 (2011). https://doi.org/10.1007/s11816-011-0165-4
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DOI: https://doi.org/10.1007/s11816-011-0165-4