Current Science

Open Access Open Access  Restricted Access Subscription Access

Isolation and Structural Elucidation of an Isothiocyanate Compound from Indigofera tinctoria Linn. Extract


Affiliations
1 Department of Bioscience and Biotechnology, Banasthali University, Niwai 304 022, India
 

Indigofera tinctoria is a well-known medicinal plant that possesses several therapeutic activities. Isothiocyanate derivative from hydroethanolic extract of Indigoferatinctoria (HEIT) was isolated by means of chromatographic techniques, i.e. adsorption chromatography,thin layer chromatography and high-pressure liquid chromatography. Structural characterization of isolated compound was done using various spectroscopic techniques (liquid chromatograph–mass spectrometry,1H nuclear magnetic resonance and Fourier transform-infrared spectroscopy) and the possible structure was identified as 1-[1,2-Diisothiocyanato-2-(3-isothiocyanato-2,2-dimethyl-propylsulphanyl)-ethoxy]-3-isothiocyanato-2,2-dimethyl-propane (C16H22N4OS5;m/z 446.70; ITC-1). Maximum yield of ITC-1 was obtained as 22 mg/5 g HEIT with 97% purity.

Keywords

Column Chromatography, HPLC, Indigofera tinctoria, Isothiocynate Compounds, LC–MS.
User
Notifications
Font Size

  • Block, E., Reactions of Organosulfur Compounds, Academic Press, New York, 1978.

  • Subrahmanyam, N. S., Modern Plant Taxonomy, Vikas Publishing House Pvt Ltd, New Delhi, 2009.

  • Kris-Etherton, P. M. et al., Bioactive compounds in foods: their role in the prevention of cardiovascular disease and cancer. Am. J. Med., 2002, 113(9B), 71S–88S.

  • Nadkarni, K. M., Nadkarni, A. K. and Chopra, R. N., In Indian Materia Medica, Popular Prakashan, Bombay, India, 1991.

  • Singh, A., Medicinal Plants of the World, Oxford & IBH Publishing Co, New Delhi, 2006.

  • Savithramma, N., Sulochana, Ch. and Rao, K. N., Ethnobotanical survey of plants used to treat asthma in Andhra Pradesh, India. J. Ethnopharmacol., 2007, 113(1), 4–61.

  • Motamarri, S. N., Karthikeyan, M., Rajasekar, S. and Gopal, V., Indigofera tinctoria Linn – a phytopharmacological review. Int. J. Res. Pharm. Biomed. Sci., 2012, 3(1), 164–169.

  • Khandelwal, K. P., Practical Pharmacology: Techniques and Experiments, Nirali Prakashan, Pune, India, 2006.

  • Causes of retention time drift in HPLC; http://www.crawford-scientific.com/Chromatography-Technical-Tips-Retention-Time-Drift-in-HPLC.html (accessed on 17 January 2017).

  • Perkin, A. G. and Bloxam, W. P., XXX – Some constituents of natural indigo. Part I. J. Chem. Soc. Trans., 1907, 91, 279–288.

  • Kamal, R. and Mangla, M., In vivo and in vitro investigations on rotenoids from Indigofera tinctoria and their bioefficacy against the larvae of Anopheles stephensi and adults of Callosobruchus chinensis. J. Biosci., 1993, 18(1), 93–101.

  • Kamal, R. and Mangla, M., In vivo and in vitro production of histamine from Indigofera tinctoria. Indian Drugs, 1992, 29, 179.

  • Singh, B. et al., Isolation, structure elucidation and in vivo hepatoprotective potential of trans‐tetracos‐15‐enoic acid from Indigofera tinctoria Linn. Phytother. Res., 2006, 20(10), 831–839.

  • Yadav, R. K., Singh, D., Verma, D. M. and Maheshwari, R. K., Effects of rotenoids from Indigofera tinctoria (L) R. Br. On Callosobruchus chinensis and Trogoderma granarium. Bull. Environ. Pharmacol. Life Sci., 2013, 2(9), 24–29.

  • Yanping, X., Szilvia, S. and Zhe, L., The antioxidant role of thiocyanate in the pathogenesis of cystic fibrosis and other inflammationrelated diseases. Proc. Natl. Acad. Sci., 2009, 106(48), 20515–20519.

  • Singh, S. V. and Singh, K., Cancer chemoprevention with dietary isothiocyanates matures for clinical translational research. Carcinogenesis, 2012, 33(10), 1833–1842.

  • Moriarty, R. M., Naithani, R. and Surve, B., Organosulfur compounds in cancer chemoprevention. Mini. Rev. Med. Chem., 2007, 7(8), 827–838.

  • Tsimberidou, A. M. and Keating, M. J., Treatment of fludarabinerefractory chronic lymphocytic leukemia. Cancer, 2009, 115(13), 2824–2836.

  • Madhunapantula, S. V. and Robertson, G. P., Therapeutic implications of targeting AKT signaling in melanoma. Enzyme Res., 2011, 2011, 1–20.

  • Wall, T., How broccoli fights cancer? Discovery News, 2011; http://news.discovery.com/human/health/how-broccoli-fights-cancer110310.html

  • Wang, X. et al., Selective depletion of mutant p53 by cancer chemo-preventive isothiocyanates and their structure-activity relationships. J. Med. Chem., 2011, 54(3), 809–816.

  • Wattenberg, L. W., Inhibition of carcinogenic effects of polycyclic hydrocarbons by benzyl isothiocyanate and related compounds. J. Natl. Cancer. Inst., 1977, 58(2), 395–398.

  • Sugie, S., Okumura, A., Tanaka, T. and Mori, H., Inhibitory effects of benzyl isothiocyanate and benzyl thiocyanate on diethylnitrosamine induced hepatocarcinogenesis in rats. Jpn. J. Cancer. Res., 1993, 84, 865-870.

  • Cinciripini, P. M., Hecht, S. S., Henningfield, J. E., Manley, M. W. and Kramer, B. S., Tobacco addiction: implications for treatment and cancer prevention. J. Natl. Cancer. Inst., 1997, 89(24), 1852–1867.

  • Chung, F. L., Conaway, C. C., Rao, C. V. and Reddy, B. S., Chemoprevention of colonic aberrant crypt foci in Fischer rats by sulforaphane and phenyl isothiocyanate. Carcinogenesis, 2000, 21(12), 2287–2291.

  • Hecht, S. S., Kenny, P. M., Wang, M., Trushin, N. and Upadhyaya, P., Effects of phenethyl isothiocyanate and benzyl isothiocyanate, individually and in combination, on lung tumorigenesis induced in A/J mice by benzo[a]pyrene and 4-(methylnitrosamino)1-(3-pyridyl)-1-butanone. Cancer Lett., 2000, 50(1), 49–56.

  • London, S. J., Yuan, J. M., Chung, F. L., Gao, Y. T., Coetzee, G. A., Ross, R. K. and Yu, M. C., Isothiocyanates, glutathione Stransferase M1 and T1 polymorphisms, and lung cancer risk: a prospective study of men in Shanghai, China. Lancet, 2000, 356(9231), 724–729.

  • Kuroiwa, Y., Nishikawa, A., Kitamura, Y., Kanki, K., Ishii, Y., Umemura, T. and Hirose, M., Protective effects of benzyl isothiocyanate and sulforaphane but not resveratrol against initiation of pancreatic carcinogenesis in hamsters. Cancer Lett., 2006, 241(2), 275–280.

  • Fahey, J. W., Zalcmann, A. T. and Talalay, P., The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry, 2001, 56(1), 5–51.


Abstract Views: 332

PDF Views: 124




  • Isolation and Structural Elucidation of an Isothiocyanate Compound from Indigofera tinctoria Linn. Extract

Abstract Views: 332  |  PDF Views: 124

Authors

Veena Sharma
Department of Bioscience and Biotechnology, Banasthali University, Niwai 304 022, India
Rashmi Singh
Department of Bioscience and Biotechnology, Banasthali University, Niwai 304 022, India

Abstract


Indigofera tinctoria is a well-known medicinal plant that possesses several therapeutic activities. Isothiocyanate derivative from hydroethanolic extract of Indigoferatinctoria (HEIT) was isolated by means of chromatographic techniques, i.e. adsorption chromatography,thin layer chromatography and high-pressure liquid chromatography. Structural characterization of isolated compound was done using various spectroscopic techniques (liquid chromatograph–mass spectrometry,1H nuclear magnetic resonance and Fourier transform-infrared spectroscopy) and the possible structure was identified as 1-[1,2-Diisothiocyanato-2-(3-isothiocyanato-2,2-dimethyl-propylsulphanyl)-ethoxy]-3-isothiocyanato-2,2-dimethyl-propane (C16H22N4OS5;m/z 446.70; ITC-1). Maximum yield of ITC-1 was obtained as 22 mg/5 g HEIT with 97% purity.

Keywords


Column Chromatography, HPLC, Indigofera tinctoria, Isothiocynate Compounds, LC–MS.

References





DOI: https://doi.org/10.18520/cs%2Fv113%2Fi05%2F941-946