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  • 1 University of Medicine and Pharmacy Târgu Mureş, 540139 Târgu Mureş, Romania
  • | 2 University of Szeged, H-6720 Szeged, Hungary
  • | 3 University of Szeged, H-6720 Szeged, Hungary
  • | 4 University of Szeged, H-6720 Szeged, Hungary
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Physalin D was isolated from the methanol extract of Physalis alkekengi L. fruits by combination of different chromatographic methods (CPC, TLC, HPLC). The structure was elucidated based on 1H and 13C NMR spectral analysis with the aid of 2D-correlation spectroscopy (1H, 1H-COSY, HSQC and HMBC) and comparison with literature data. The quantity of physalin D in mature and immature fruits and calyces was determined by RP-HPLC-UV method. Among the studied samples, immature calyx showed the highest content of physalin D (0.7880 ± 0.0612%), while mature calyx contained 4 times less amount (0.2028 ± 0.016%). The physalin D content of the fruit was much lower; immature fruits contained 0.0992 ± 0.0083% physalin D and mature fruits 0.0259 ± 0.0021%. The antiproliferative activity of the CHCl3 extract and its fractions was tested on three cancer cell lines (HeLa, MCF-7 and A431). The antiproliferative activity of physalin D is discussed with regard the published data.

  • 1.

    Bahmani, M., Rafieian-Kopaei, R., Naghdi, N., Nejad, A. S. M., Afsordeh, O. (2016) Physalis alkekengi: A review of its therapeutic effects. J. Chem. Pharm. Sci. 9, 14721475.

    • Search Google Scholar
    • Export Citation
  • 2.

    Ciocarlan, V. (2000) Flora ilustrată a României. Editura Ceres, Bucureşti, pp. 616

  • 3.

    Damu, A. G., Kou, P. C., Su, C. R., Kuo, T. H., Chen, T. H., Bastow, K. F., Lee, K. H., Wu, T. S. (2007) Isolation, structures, and structure–cytotoxic activity relationships of with anolides and physalins from Physalis angulata. J. Nat. Prod. 70, 11461152.

    • Search Google Scholar
    • Export Citation
  • 4.

    Guimaraes, E. T., Lima, M. S., Santos, L. A., Ribeiro, I. M., Tomassini, T. C. B., Ribeiro dos Santos, R., Washington, L. C., Soares, M. B. (2009) Activity of physalins purified from Physalis angulata in in vitro and in vivo models of cutaneous leishmaniasis, J. Antimicrob. Chemother. 64, 8487.

    • Search Google Scholar
    • Export Citation
  • 5.

    Hegnauer, R. (1973) Chemotaxonomie der Pflanzen. Vol. VI, Birkhäuser Verlag, Basel und Stuttgart, pp. 411432.

  • 6.

    Helvaci, S., Kökdil, G., Kawai, M., Duran, N., Duran, G., Güvenç, A. (2010) Antimicrobial activity of the extracts and physalin D from Physalis alkekengi and evaluation of antioxidant potential of physalin D. Pharm. Biol. 48, 142150.

    • Search Google Scholar
    • Export Citation
  • 7.

    Januário, A. H., Rodrigues Filho, E., Pietro, R. C. L. R., Kashima, S., Sato, D. N., França, S. C. (2002) Antimycobacterial physalins from Physalis angulata L. (Solanaceae). Phytother. Res. 16, 445448.

    • Search Google Scholar
    • Export Citation
  • 8.

    Kawai, M., Makino, B., Yamamura, H., Araki, S., Butsugan, Y., Ohya, J. (2002) Cytotoxic activity of physalins and related compounds against HeLa cells. Pharmazie 57, 348350.

    • Search Google Scholar
    • Export Citation
  • 9.

    Kawai, M., Makino, B., Yamamura, H., Butsugan, Y. (1996) Upon “physalin L” isolated from Physalis minima. Phytochemistry 43, 661663.

    • Search Google Scholar
    • Export Citation
  • 10.

    Kawai, M., Matsuura, T. (1970) The structure of physalin C. A bitter principle of Physalis alkekengi var. franchetii. Tetrahedron 26, 17431745.

    • Search Google Scholar
    • Export Citation
  • 11.

    Kawai, M., Matsuura, T., Kyuno, S., Matsuki, H., Takenaka, M., Katsuoka, T., Butsugan, Y., Saito, K. (1987) A new physalin from Physalis alkekengi: structure of physalin L. Phytochemistry 26, 33133317.

    • Search Google Scholar
    • Export Citation
  • 12.

    Kawai, M., Ogura, T., Makino, B., Matsumoto, A., Yamamura, H., Butsugan, Y., Hayashi, M. (1992) Physalins N and O from Physalis alkekengi. Phytochemistry 31, 42994302.

    • Search Google Scholar
    • Export Citation
  • 13.

    Kawai, M., Yamamoto, T., Makino, B., Yamamura, H., Araki, S., Butsugan, Y., Saito, K. (2001) The structure of physalin T from Physalis alkekengi var. franchetii. J. Asian Nat. Prod. Res. 3, 199205.

    • Search Google Scholar
    • Export Citation
  • 14.

    Lima, M. S., Evangelista, A. F., Santos, G. G., Ribeiro, I. M., Tomassini, T. C. B., Pereira Soares, M. B., Villarreal, C. F. (2014) Antinociceptive properties of physalins from Physalis angulata. J. Nat. Prod. 77, 23972403.

    • Search Google Scholar
    • Export Citation
  • 15.

    Magalhães, H. I., Veras, M. L., Torres, M. R., Alves, A. P., Pessoa, O. D., Silveira, E. R., Costa-Lotufo, L. V., de Moraes, M. O., Pessoa, C. (2006) In-vitro and in-vivo antitumour activity of physalins B and D from Physalis angulata. J. Pharm. Pharmacol. 58, 235241.

    • Search Google Scholar
    • Export Citation
  • 16.

    Makino, B., Kawai, M., Iwata, Y., Yamamura, H., Butsugan, Y., Ogawa, K., Hayashi, M. (1995) Physalins possessing an endoperoxy structure from Physalis alkekengi var. franchetii. structural revision of physalin K. Bull. Chem. Soc. Jpn. 68, 219226.

    • Search Google Scholar
    • Export Citation
  • 17.

    Makino, B., Kawai, M., Kito, K., Yamamura, H., Butsugan, Y. (1995) New physalins possessing an additional carbon-carbon bond from Physalis alkekengi var. franchetii. Tetrahedron 51, 1252912538.

    • Search Google Scholar
    • Export Citation
  • 18.

    Makino, B., Kawai, M., Ogura, T., Nakanishi, M., Yamamura, H., Butsugan, Y. (1995) Structural revision of physalin H isolated from Physalis angulata. J. Nat. Prod. 58, 16681674.

    • Search Google Scholar
    • Export Citation
  • 19.

    Makino, B., Ohya, J., Yamamura, H. (2002) Cytotoxic activity of physalins possessing modified skeletal structures against HeLa cells. Pharmazie 57, 7071.

    • Search Google Scholar
    • Export Citation
  • 20.

    Matsuura, T., Kawai, M. (1969) Bitter principles of Physalis alkekengi var. franchetii: structure of physalin B. Tetrahedron Lett. 10, 17651766.

    • Search Google Scholar
    • Export Citation
  • 21.

    Matsuura, T., Kawai, M., Nakashima, R., Butsugan, Y. (1969) Bitter principles of Physalis alkekengi var. franchetii: structure of physalin A. Tetrahedron Lett. 10, 10831086.

    • Search Google Scholar
    • Export Citation
  • 22.

    Men, R., Li, N., Tang, Y., Xing, Y., Ding, C., Ding, W., Ma, Z. (2016) Chemopreventive agents from Physalis minima function as Michael reaction acceptors. Pharmacogn. Mag. 12, 231236.

    • Search Google Scholar
    • Export Citation
  • 23.

    Moore, D. M. (1972) Solanaceae. In: Tutin, T. G., Heywood, V. H., Burges, N. A., Moore, D. M., Valentine, D. H., Walters, S. M., Webb, D. A. (eds), Flora Europaea. Vol. 3, University Press, Cambridge, p. 196.

    • Search Google Scholar
    • Export Citation
  • 24.

    Mosmann, T. (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assay. J. Immunol. Methods 65, 5563.

    • Search Google Scholar
    • Export Citation
  • 25.

    Peng, X., Wu, Q., Gao, C., Gai, C., Yuan, D., Fu, H. (2015) Chemical constituents from the fruit calyx of Physalis alkekengi var. francheti, J. Chin. Pharm. Sci. 24, 600606.

    • Search Google Scholar
    • Export Citation
  • 26.

    Qui, L., Jiang, Z. H., Liu, H. X., Chen, L. X., Yao, X. S., Qui, F. (2008) A pair of 3-epimeric physalins from Physalis alkekengi L. var. franchetii. J. Asian Nat. Prod. Res. 10, 881885.

    • Search Google Scholar
    • Export Citation
  • 27.

    Qui, L., Zhao, F., Jiang, Z. H., Chen, L. X., Zhao, Q., Liu, H. X., Yao, X. S., Qui, F. (2008) Steroids and flavonoids from Physalis alkekengi var. franchetii and their inhibitory effect on nitric oxide production. J. Nat. Prod. 71, 642646.

    • Search Google Scholar
    • Export Citation
  • 28.

    Ray, A. B., Gupta, M. (1994) With asteroids, a growing group of naturally occurring steroidal lactones. In: Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch. (eds), Progress in the Chemistry of Organic Natural Products. Vol. 63, Springer Verlag, Wien, New York, pp. 1106.

    • Search Google Scholar
    • Export Citation
  • 29.

    Row, L. R., Reddy, K. S., Sarma, N. S., Matsuura, T., Nakashima, R. (1980) New physalins from Physalis angulata and Physalis lancifolia. Structure and reactions of physalins D, I, G and K. Phytochemistry 19, 11751181.

    • Search Google Scholar
    • Export Citation
  • 30.

    Row, L. R., Sarma, N. S., Matsuura, T., Nakashima, R. (1978) Physalins E and H, new physalins from Physalis angulata and P. lancifolia. Phytochemistry 17, 16411645.

    • Search Google Scholar
    • Export Citation
  • 31.

    Row, L. R., Sarma, N. S., Reddy, K. S., Matsuura, T., Nakashima, R. (1978) Structure of physalins F and H from Physalis angulata and P. lancifolia. Phytochemistry 17, 16471650.

    • Search Google Scholar
    • Export Citation
  • 32.

    , M. S., de Menezes, M. N., Krettli, A. U., Ribeiro, I. M., Tomassini, T. C., Ribeiro dos Santos, R., de Azevedo, W. F. Jr., Soares, M. B. (2011) Antimalarial activity of physalins B, D, F, and G. J. Nat. Prod. 74, 22692272.

    • Search Google Scholar
    • Export Citation
  • 33.

    Sunayama, R., Kuroyanagi, M., Umehara, K., Ueno, A. (1993) Physalin and neophysalins from Physalis alkekengi var. franchetii and their differentiation inducing activity, Phytochemistry 34, 529533.

    • Search Google Scholar
    • Export Citation

Editorial Board

      Csányi, Vilmos (Göd)
      Dudits, Dénes (Szeged)
      Falus, András (Budapest)
      Fischer, Ernő (Pécs)
      Gábriel, Róbert (Pécs)
      Gulya, Károly (Szeged)
      Gulyás, Balázs (Stockholm)
      Hajós, Ferenc (Budapest)
      Hámori, József (Budapest)
      Heszky, László (Gödöllő)
      Hideg, Éva (Szeged)
      E. Ito (Sanuki)
      Janda, Tibor (Martonvásár)
      Kavanaugh, Michael P. (Missoula)
      Kása, Péter (Szeged)
      Klein, Éva (Stockholm)
      Kovács, János (Budapest)
      Brigitte Mauch-Mani (Neuchâtel)
      Nässel, Dick R. (Stockholm)
      Nemcsók, János (Szeged)
      Péczely, Péter (Gödöllő)
      Roberts, D. F. (Newcastle-upon-Tyne)
      Sakharov, Dimitri A. (Moscow)
      Singh, Meharvan (Fort Worth)
      Sipiczky, Mátyás (Debrecen)
      Szeberényi, József (Pécs)
      Székely, György (Debrecen)
      Tari, Irma (Szeged)
      Vágvölgyi, Csaba (Szeged),
      L. Zaborszky (Newark)

 

Acta Biologica Hungarica
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Acta Biologica Hungarica
Language English
Size  
Year of
Foundation
1950
Publication
Programme
changed title
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per Year
 
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per Year
 
Founder Magyar Tudományos Akadémia
Founder's
Address
H-1051 Budapest, Hungary, Széchenyi István tér 9.
Publisher Akadémiai Kiadó
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H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
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Chief Executive Officer, Akadémiai Kiadó
ISSN 0236-5383 (Print)
ISSN 1588-256X (Online)