JOURNAL OF THE CZECH PHARMACEUTICAL SOCIETY AND THE SLOVAK PHARMACEUTICAL SOCIETY

Čes. slov. farm. 2006, 55(4):151-159

Naphthoquinones - biosynthesis, occurrence and metabolism in plants

P. Babula1, R. Mikelová2, V. Adam2, R. Kizek2, L. Havel3, Z. Sladký1
1 Veterinární a farmaceutická univerzita Brno, Farmaceutická fakulta, Ústav přírodních léčiv
2 Mendelova zemědělská a lesnická univerzita v Brně, Agronomická fakulta, Ústav chemie a biochemie
3 Mendelova zemědělská a lesnická univerzita v Brně, Agronomická fakulta, Ústav biologie rostlin

Naphthoquinones are relatively widely occurring natural substances, products of secondary metabolism of some actinomycetes, fungi, lichens, and higher plants. The importance of these substances for the producers proper is, due to their wide biological activity, still discussed. In most cases they act as phytoalexines. In the case of fungi, they may play a significant role in the pathogenicity of moulds - naphthoquinones interact with mitochondria, microsomes and cytoplasmic proteins, in the form of radicals they are bound to DNA and RNA, and they do damage to them. Naphthoquinones are highly cytotoxic substances; their antimicrobial, antifungal, antiviral and antiparasitic effects have been observed. In traditional medicines, particularly in some parts of Asia (China) and South America, naphthoquinones-containing plants are widely used primarily in the treatment of various tumoral and parasitic diseases.

Keywords: plumbagin; juglone; vitamin K; shikimic acid; Drosera

Received: July 28, 2005; Accepted: May 3, 2006; Published: April 1, 2006  Show citation

ACS AIP APA ASA Harvard Chicago Chicago Notes IEEE ISO690 MLA NLM Turabian Vancouver
Babula P, Mikelová R, Adam V, Kizek R, Havel L, Sladký Z. Naphthoquinones - biosynthesis, occurrence and metabolism in plants. Čes. slov. farm. 2006;55(4):151-159.
Share...
Download citation
  • BibTeX (.bib)
  • Bookends (.ris)
  • EasyBib (.ris)
  • EndNote (.enw)
  • EndNote 8 (.xml)
  • ISI WoS (.isi)
  • Medlars (.medlars)
  • Mendeley (.ris)
  • MODS (.xml)
  • Papers (.ris)
  • RefWorks (.txt)
  • RefManager (.ris)
  • RIS (.ris)
  • MS Word (.xml)
  • Zotero (.ris)
    • Open full article

    References

    1. Wagner, H.: Pharmaceutische Biologie. Drogen und ihre Inhaltsstoffe, Volume 5. Stuttgart, Gustav Fischer, 1993.
    2. Gunaherath, G. M., Kamal, G. M., Gunatilaka, A. A. L. et al.: Phytochem., 1983; 22, 1245-1248. Go to original source...
    3. Yue, J., Xu, J., Zhao, Y. et al.: Chemical components from Ceratostigma willmottianum. J. Nat. Prod., 1997; 60, 1031-1033. Go to original source...
    4. Binder, R. G., Benson, M. E., Flath, R. A.: Phytochem., 1989; 10, 28. Go to original source...
    5. Bruneton, J.: Pharmacogosie, Phytochimie, Plantes Médicinales, Paris: Technique et Documentation, Lavoisier, 1993.
    6. Zhong, S. M., Waterman, P. G., Jeffreys, J. A. D.: Phytochem., 1984; 23, 1067-1072. Go to original source...
    7. Zakaria, M. B., Jeffreys, J. A. D., Waterman, P. G., Zhong, S. M.: Phytochem., 1984; 23, 1481-1484. Go to original source...
    8. Mebe, P., Cordell, G. A., and Pezzuto, J. M.: Phytochem., 1998; 47, 311-314. Go to original source...
    9. Ozgen, U., Coskun, M., Kazaz, C., Secen, H.: Turkish journal of chemistry, 2004; 28, 451-454.
    10. Staniforth, V., Wang, S. Y., Shyur, L. F., Yang, N. S.: Journal of Biological chemistry, 2004; 279, 5877-5885. Go to original source... Go to PubMed...
    11. Mita, G., Gerardi, C., Miceli, A. et al.: Plant Cell Reports, 1994; 13, 406-410. Go to original source... Go to PubMed...
    12. Bieber, L. W., Brebs, H. C., Schafer, W.: Phytochem., 1994; 35, 1027-1028. Go to original source...
    13. Bringman, G., Rischer, H., Wohlfahrt, M. et al.: Phytochem., 2000; 53, 339-344.
    14. Williams, C. A., Harborne, J. B., Goldblatt, P.: Phytochem., 1986; 25, 2135-2154. Go to original source...
    15. Hara, H., Maruyama, N., Yamashita, S. et al.: Chem. and Pharm. Bull., 1997; 45, 1714-1716. Go to original source...
    16. Khan, R. M., Mlungwana, S. M.: Phytochem., 1995; 50, 439-442. Go to original source...
    17. Gupta, P. K., Singh, P.: Journal of asian natural products research, 2004; 6, 237-240. Go to original source... Go to PubMed...
    18. Itoigawa, M., Ito, C., Tan, H. T. W. et al.: Cancer Letters, 2001; 174, 135-139. Go to original source... Go to PubMed...
    19. Gormann, R., Kaloga, M., Li, X. C. et al.: Phytochem., 2003; 64, 583-587. Go to original source... Go to PubMed...
    20. Gafner, S., Wolfender, J. L., Nianga, M. et al.: Phytochem., 1996; 42, 1315-1320. Go to original source... Go to PubMed...
    21. De Moura, K. C. G., Emery, F. S., Neves-Pinto, C. et al.: J. Braz. Chem. Soc., 2001; 12, 325-338. Go to original source...
    22. Zani, C. L., Oliveira, A. B. D., Oliviera, G. D.: Phytochem., 1991; 30, 2379-2381. Go to original source...
    23. Rogathi, B. K., Gupta, B. R., Roy, D., Kjhanna, R. N.: J. Chem., 1993; 22, 886-889.
    24. Shetgiri, N. P., Kokitkar, S. V., Sawant, S. N.: Acta Pol. Pharm., 2001; 58, 133-136.
    25. Duarte, D. S., Dolabela, M. F., Salas, C. E. et al.: J. Pharm. Pharmacol., 2000; 52, 347-352. Go to original source... Go to PubMed...
    26. Inouye, K., Chen, C. C.: Phytochem., 1981; 20, 2271-2276. Go to original source...
    27. Moideen, S. V. K., Houghton, P. J., Rock, P. et al.: Planta Med., 1999; 65, 536-540. Go to original source... Go to PubMed...
    28. Singh, P., Singh, A.: Pharm., 1980; 35, 701-702.
    29. Jassbi, A. R., Singh, P., Jain, S., Tahara, S.: Helvetica Chimica Acta, 2004; 87, 820-824. Go to original source...
    30. Onegi, B., Kraft, C., Kohler, I. et al.: Phytochem., 2002; 60, 39-44. Go to original source... Go to PubMed...
    31. Jacome, R. L. R. P., de Oliveira, A. B., Raslan, D. S. et al.: Quimica Nova, 1999; 22, 175-177. Go to original source...
    32. Kizu, H. et al.: Yakugaku Zasshi-journal of the pharmaceutical society of Japan, 1994; 144, 492-513. Go to original source... Go to PubMed...
    33. Itokawa, H., Matsumoto, K., Morita, H., Takeya, K.: Phytochem., 1992; 31, 1061-1062. Go to original source...
    34. Zenk, M. H., Furbringer, M., Steglich, W.: Phytochem., 1969; 8, 2199-2220. Go to original source...
    35. Culham, A., Gornall, R. J.: Biochem. Syst. and Ecol., 1994; 22, 507-515. Go to original source...
    36. Kreher, B., Neszmelyi, A., Wagner, H.: Phytochem., 1990; 29, 605-606. Go to original source...
    37. Babula, P., Mikelova, R., Adam, V. et al.: Chem. Listy, 2006; 100, 271-276.
    38. Likhitwitayaawud, K., Kaewamatawong, R., Ruandgungsi, N., Krungkrai, J.: Planta Med., 1998; 64, 237-241. Go to original source... Go to PubMed...
    39. Bruneton, J.: Pharmacognosy, Phytochemistry, Medicinal Plants, Andover, England UK, 1995.
    40. Ali, B. H., Bashir, A. K., Tanira, M. O. M.: Pharmacology, 1995; 51, 356-363. Go to original source... Go to PubMed...
    41. Fournet, A., Angelo, A., Munoz, V. et al.: J. Ethnopharmacol., 1992; 32, 159-164. Go to original source... Go to PubMed...
    42. Wu, T. S., Hsu, H. C., Wu, P. L. et al.: Chem. and Pharm. Bull., 1998; 46, 413-418. Go to original source... Go to PubMed...
    43. Medentsev, A. G., Maslov, A. N., Akimenko, V. K.: Biochemistry - Moscow, 1990; 55, 1319-1323.
    44. Kurobane, I., Zaita, N., Fukuda, A.: J. Antibiot., 1986; 39, 205-214. Go to original source... Go to PubMed...
    45. Moore, S. B., Hopke, N. J.: Chem. Biochem., 2001; 2, 35-38. Go to original source...
    46. Medentsev, A. G., Akimenko, V. K.: Phytochem., 1998; 47, 935-959. Go to original source... Go to PubMed...
    47. Rizzacasa, M. A., Sargent, V. M.: J. Chem. Soc. Perkin. Trans., 1987; 1, 2017-2022. Go to original source...
    48. Murray, R. K., Granner, D. K., Mayes, P. A., Rodwell, V. W.: Harperova biochemie, Jinočany, H+H, 2002.
    49. Tomko, J. et al.: Farmakognózia, učebnica pre farmaceutické fakulty, 2. opravené vydání. Martin, Osveta, 1999.
    50. Rischer, H., Hamm, A., Bringman, G.: Phytochem., 2002; 59, 603-609. Go to original source... Go to PubMed...
    51. Duroux, L., Delmotte, F. M., Lancelin, J. M. et al.: Biochemical Journal, 1998; 333, 275-283. Go to original source... Go to PubMed...
    52. Medentsev, A. G., Akimenko, V. K.: Microbiology, 1997; 66, 647-651.
    53. Takashi, T., Atsushi, D., Noboru, T., Minoru, U.: Bull. Chem. Soc. Jpn., 2004; 77, 537-541.
    54. Krishnaswamy, M., Purushothaman, K. K.: Indian J. Exp. Biol., 1998; 18, 876-877.
    55. Srinivas, P., Gopinath, G., Banerji, A. et al.: Molecular Carcinogenesis 2004; 4, 201-211. Go to original source... Go to PubMed...
    56. Ravelo, A. G., Estevez-Braun, A., ChavezOrellana, H. et al.: Current topics in medicinal chemistry, 2004; 4, 241-265. Go to original source... Go to PubMed...
    57. Krishnan, P., Bastow, K. F.: Biochem. Pharmacol., 2000; 60, 1367-1379. Go to original source... Go to PubMed...
    58. Didry, N., Dubreuil, L., Pinkas, M.: Pharmazie, 1994; 49, 681-683.
    59. de Paiva, S. R., Figueiredo, M. R., Aragao, T. V., Kaplan, M. A. C.: Memorias do instituto oswaldo cruz, 2003; 98, 959-961. Go to original source... Go to PubMed...
    60. Oliveira, C. G. T., Miranda, F. F., Ferreira, V. F. et al.: J. Braz. Chem. Soc., 2001; 12, 229-345. Go to original source...
    61. Hazra, B., Sarkar, R., Bhattacharyya, S. et al.: Phytoter. Res., 2002; 16, 133-137. Go to original source... Go to PubMed...
    62. Ray, S., Hazra, B., Mittra, B. et al.: Molecular Pharmacology, 1998; 54, 994-999. Go to original source... Go to PubMed...
    63. Floreani, M., Forlin, A., Pandolfo, L. et al.: J. Pharmacol. Exp. Ther., 1996; 278, 763-770. Go to original source...
    64. Sharma, I., Gusain, D., Dixit, V. P.: Ind. J. Physiol. Pharmacol., 1991; 35, 10-14.
    65. Czygan, F. C.: Sonnentaukraut. In Teedrogen und Phytopharmakd, Stuttgart: Wissenschaftliche Verlagsgellschaft;, 1989
    66. Satyavati, G. V., Gupta, A. K., Tandon, N.: Medicinal plants of India. In: Indian Council of Medicinal Research,, 1987; 2, 472: New Delhi.
    67. Premakumari, P., Rathinam, K., Santhakumari, G.: Ind. J. Med. Res., 1977; 65, 829-838.
    68. Chen, X., Yang, L., Oppenheim, J. J., Howard, O. M. Z.: Phytoter. Res., 2002; 16, 16. Go to original source... Go to PubMed...
    69. Schmeda-Hirschmann, G., Papastergiou, F.: Zeitschrift fur Naturforschung C-A Journal of Biosciences, 2003; 58, 495-501. Go to original source... Go to PubMed...
    70. Ali, S., Sing, P., Thomson, R. H.: J. Chem. Soc. Perkin. Trans., 1980; 1, 257-259. Go to original source...
    71. Aguinaldo, A. M., Armstrong, J. A., Cannon, J. R. et al.: Australian Journal of Chemistry, 1996; 49, 197-198. Go to original source...

    Return to the content


    Czech and Slovak Pharmacy

    Madam, Sir,
    please be aware that the website on which you intend to enter, not the general public because it contains technical information about medicines, including advertisements relating to medicinal products. This information and communication professionals are solely under §2 of the Act n.40/1995 Coll. Is active persons authorized to prescribe or supply (hereinafter expert).
    Take note that if you are not an expert, you run the risk of danger to their health or the health of other persons, if you the obtained information improperly understood or interpreted, and especially advertising which may be part of this site, or whether you used it for self-diagnosis or medical treatment, whether in relation to each other in person or in relation to others.

    I declare:

    1. that I have met the above instruction
    2. I'm an expert within the meaning of the Act n.40/1995 Coll. the regulation of advertising, as amended, and I am aware of the risks that would be a person other than the expert input to these sites exhibited

    No
    Yes

    If your statement is not true, please be aware
    that brings the risk of danger to their health or the health of others.