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Biologically active C-alkylated flavonoids from Dodonaea viscosa

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Abstract

A new C-alkylated flavonoid (5,7-dihydroxy-3′-(4″-acetoxy-3″-methylbutyl)-3,6,4′-trimethoxyflavone (1), along with two known C-alkylated flavonoids (5,7-dihydroxy-3′-(3-hydroxymethylbutyl)-3,6,4′-trimethoxyflavone (2), 5,7,4′-trihydroxy-3′-(3-hyroxymethylbutyl)-3,6-dimethoxyflavone (3) and two new source C-alkylated flavonoids (5,7-dihydroxy-3′-(2-hydroxy-3-methyl-3-butenyl)-3,6,4′-trimethoxyflavone (4), 5,7,4′-trihydroxy-3,6-dimethoxy-3′-isoprenyl-flavone (5) were isolated from the aerial parts of Dodonaea viscosa. The structures of all compounds were established on the basis of 1D and 2D NMR spectroscopy and mass spectrometry. The isolated compounds were evaluated for their inhibitory effect on urease and α-chymotrypsin enzyme. All the compounds (1–5) exhibited mild inhibition against urease but remained recessive in case of α-chymotrypsin.

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References

  • Abdullah, P., Sapindaceae. In Nasir, E. and Ali, S. I. (Eds). Flora of West Pakistan No. 39. Stewart Herbarium, Gordon College, Rawalpindi, pp. 1–3, (1973).

    Google Scholar 

  • Anis, I., Ahmed, S., Malik, A., Yasin, A., and Choudhary, M. I., Enzyme inhibitory constituents from Duranta repens. Chem. Pharm. Bull., 50, 515–518 (2002).

    Article  PubMed  CAS  Google Scholar 

  • Arfan, M., Ali, M., Anis, I., Ahmad, H., Choudhary, M. I., Khan, A., and Shah, M. R., Urease inhibitors from Hypericum oblongifolium Wall. J. Enzym. Inhib. Med. Chem., 25, 296–299 (2010).

    Article  CAS  Google Scholar 

  • Arun, M. and Asha, V. V., Gastroprotective effect of Dodonaea viscosa on various experimental ulcer models. J. Ethnopharmacol., 118, 460–465 (2008).

    Article  PubMed  CAS  Google Scholar 

  • Atta-ur-Rahman and Choudhary, M. I., Bioactive natural products as a potential source of new pharmacophores. A theory of memory. Pure Appl. Chem., 73, 555–560 (2001).

    Article  CAS  Google Scholar 

  • Azhar-ul-Haq, Malik, A., Khan, A. U., Shah, M. R., and Muhammad, P., Spinoside, new coumaroyl flavone glycoside from Amaranthus spinosus. Arch. Pharm. Res., 27, 1216–1219 (2004).

    Article  PubMed  CAS  Google Scholar 

  • Cannell, R. J. P., Kellam, S. J., Owsianka, A. M., and Walker, J. M., Results of a Large Scale Screen Microalgae for the production of protease inhibitors. Planta Med., 54, 10–14 (1988).

    Article  PubMed  CAS  Google Scholar 

  • Clarkson, C., Maharaj, V. J., Crouch, N. R., Grace, O. M., Pillay, P., Matsabisa, M. G., Bhagwandin, N., Smith, P. J., and Folb, P. I., In vitro antiplasmodial activity of medicinal plants native to or naturalized in South Africa. J. Ethnopharmacol., 92, 177–191 (2004).

    Article  PubMed  Google Scholar 

  • Coblentz, A. and Coblentz, D. R., Treatment of peptic ulcer with chymotrypsin and an antibiotic. Mil. Med., 131, 150–154 (1966).

    PubMed  CAS  Google Scholar 

  • Coblentz, A., Treatment of geriatric peptic ulcer with chymotrypsin and an antibiotic. J. Am. Geriatr. Soc., 16, 1039–1046 (1968).

    PubMed  CAS  Google Scholar 

  • Ferheen, S., Ahmed, E., Afza, N., Malik, A., Shah, M. R., Nawaz, S. A., and Choudhary, M. I., Haloxylines A and B, antifungal and cholinesterase inhibiting piperidine alkaloids from Haloxylon salicornicum. Chem. Pharm. Bull., 53, 570–572 (2005).

    Article  PubMed  CAS  Google Scholar 

  • Hussain, J., Ullah, F., Hussain, H., Hussain, S. T., and Shah, M. R., Nepetolide: A new diterpene from Nepeta suavis. Z. Naturforsch. B, 63, 591–594 (2008).

    CAS  Google Scholar 

  • Hussain, J., Jamila, N., Khan, F. U., Devkota, K. P., Shah, M. R., and Anwar, S., Nepetanal and nepetanoate: A new diterpene aldehyde and a benzene derivative ester from Nepeta juncea. Magn. Reson. Chem., 47, 625–627 (2009a).

    Article  PubMed  CAS  Google Scholar 

  • Hussain, J., Khan, F. U., Rehman, N. U., Ullah, R., Mohmmad, Z., Tasleem, S., Naeem, A., and Shah, M. R., One new triterpene ester from Nepeta suavis. J. Asian Nat. Prod. Res., 11, 997–1000 (2009b).

    Article  PubMed  CAS  Google Scholar 

  • Iqbal, K., Malik, A., Mukhtar, N., Anis, I., Nahar, S., and Choudhary, M. I., α-Glucosidease inhibitory constituents of Duranta repens. Chem. Pharm. Bull., 52, 785–789 (2004).

    Article  PubMed  CAS  Google Scholar 

  • Jan, A. K., Shah, M. R., Anis, I., and Marwat, I. K., In vitro antifungal and antibacterial activities of extracts of Galium tricornutum subsp Longipedunculatum. J. Enzym. Inhib. Med. Chem., 24, 192–196 (2009).

    Article  Google Scholar 

  • Khan, S. B., Azhar-Ul-Haq, Afza, N., Malik, A., Khan, M. T., Shah, M. R., and Choudhary, M. I., Tyrosinase-inhibitory long-chain esters from Amberboa ramosa. Chem. Pharm. Bull., 53, 86–89 (2005a).

    Article  PubMed  CAS  Google Scholar 

  • Khan, S. B., Azhar-ul-Haq, Perveen, S., Afza, N., Malik, A., Nawaz, S. A., Shah, M. R., and Choudhary, M. I., Butyrylcholinesterase inhibitory guaianolides from Amberboa ramosa. Arch. Pharm. Res., 28, 172–176 (2005b).

    Article  PubMed  CAS  Google Scholar 

  • Khurram, M., Khan, M. A., Hameed, A., Abbas, N., Qayum, A., and Inayat, H., Antibacterial activities of Dodonaea viscosa using contact bioautography technique. Molecules, 14, 1332–1341 (2009).

    Article  PubMed  Google Scholar 

  • Mohammad, A., Shah, M. R., Anis, I., McKee, V., and Frese, W. E. J., 7-[2-(3-Furyl)ethyl]-7,8-dimethyl-3,5,6,6a,7,8,9,10-octahydro-1H-naphtho[1,8a-c]furan-3-one. Acta Crystallogr. Sect. E Struct. Rep. Online, 66, o2529 (2010a).

    Article  PubMed  Google Scholar 

  • Mohammad, A., Shah, M. R., Anis, I., McKee, V., and Frese, W. E. J., 5,7-Dihydroxy-3,6-dimethoxy-2-(4-methoxyphenyl)-4Hchromen-4-one monohydrate. Acta Crystallogr. Sect. E Struct. Rep. Online, 66, o2716–o2717 (2010b).

    Article  PubMed  Google Scholar 

  • Nisar, M., Tariq, S. A., Marwat, I. K., Shah, M. R., and Khan, I., Antibacterial, antifungal, insecticidal, cytotoxicity and phytotoxicity studies on Indigofera gerardiana. J. Enzym. Inhib. Med. Chem., 24, 224–229 (2009).

    Article  CAS  Google Scholar 

  • Pirzada, A. J., Shaikh, W., Usmanghani, K., and Mohiuddin, E., Antifungal activity of Dodonaea viscosa Jacq extract on pathogenic fungi isolated from superficial skin infection. Pak. J. Pharm. Sci., 23, 337–340 (2010).

    PubMed  CAS  Google Scholar 

  • Riaz, N., Anis, I., Khan, P. M., Shah, R., and Malik, A., A new triterpene from Alysicarpus monolifer. Nat. Prod. Lett., 16, 415–418 (2002).

    Article  PubMed  CAS  Google Scholar 

  • Sachdev, K. and Kulshreshtha, D. K., Aliarin, A new flavonoid from Dodonaea viscosa Linn. Indian J. Chem. B, 21, 798–799 (1982).

    Google Scholar 

  • Sachdev, K. and Kulshreshtha, D. K., Flavonoids from Dodonaea viscosa. Phytochemistry, 22, 1253–1256 (1983).

    Article  CAS  Google Scholar 

  • Sharif, A., Ahmed, E., Malik, A., Riaz, N., Afza, N., Nawaz, S. A., Arshad, M., Shah, M. R., and Choudhary, M. I., Lipoxygenase inhibitory constituents from Indigofera oblongifolia. Arch. Pharm. Res., 28, 761–764 (2005).

    Article  PubMed  CAS  Google Scholar 

  • Veerapur, V. P., Prabhakar, K. R., Parihar, V. K., Bansal, P., Srinivasan, K. K., Priyadarsini, K. I., and Unnikrishnan, M. K., Antidiabetic, hypolipidaemic and antioxidant activity of Dodonaea viscosa aerial parts in streptozotocininduced diabetic rats. Int. J. Phytomed., 2, 59–70 (2010).

    Google Scholar 

  • Wagner, H., Ludwig, C., Grotjahn, L., and Khan, M. S. Y., Biologically active saponins from Dodonaea viscosa. Phytochemistry, 26, 697–701 (1987).

    Article  CAS  Google Scholar 

  • Wollenweber, E. and Roitman, J. N., New reports on surface flavonoids from Chaaebatiaria (Rosaceae), Dodonaea (Sapindaceae), Elsholtzia (Lamiaceae), and Silphium (Asteraceae). Nat. Prod. Commun., 2, 385–389 (2007).

    CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, University of Karachi, Karachi, 75270, Pakistan

    Akhtar Muhammad & Itrat Anis

  2. H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan

    Ajmal Khan, Bishnu P. Marasini, Muhammad Iqbal Choudhary & Muhammad Raza Shah

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  1. Akhtar Muhammad
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  2. Itrat Anis
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  3. Ajmal Khan
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  4. Bishnu P. Marasini
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  5. Muhammad Iqbal Choudhary
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  6. Muhammad Raza Shah
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Correspondence to Itrat Anis.

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Muhammad, A., Anis, I., Khan, A. et al. Biologically active C-alkylated flavonoids from Dodonaea viscosa . Arch. Pharm. Res. 35, 431–436 (2012). https://doi.org/10.1007/s12272-012-0305-6

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  • DOI: https://doi.org/10.1007/s12272-012-0305-6

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