Isolation and Identification of a Growth Inhibitory Substance from Heliotropium indicum L.


Heliotropium indicum L. belongs to the family Boraginaceae. The plant has been used as a folk medicine because it contains substances of various biological activities. It is also identified as a common weed which grows wildly in crop fields in tropical and subtropical regions of the world. However, there is little information on the allelopathic effect in this plant. Therefore, this study was undertaken to investigate the growth inhibitory effect and to identify the growth inhibitory substances in H. indicum. An aqueous methanol extract of H. indicum inhibited shoot and root growth of barnyard grass, foxtail fescue, timothy, cress, lettuce and rapeseed at concentrations higher than 10 mg dry weight equivalent extract/mL. The concentrations required for 50% growth inhibition (I50) of those test plants ranged from 3–282 mg dry weight equivalent extract/mL. The extract was then separated using a sequence of chromatographic fractionations and a growth inhibitory substance was isolated and identified by spectral analysis as methyl caffeate. Methyl caffeate inhibited the growth of lettuce and foxtail fescue at concentrations higher than 1.0 mM. The results suggest that methyl caffeate may contribute to the growth inhibitory effect of H. indicum and may play an important role in the allelopathic effect of H. indicum.


  1. 1.

    Abubakar, M. S., Musa, A. M., Ahmed, A., Hussaini, I. M. (2007) The perception and practice of traditional medicine in the treatment of cancers and inflammations by the Hausa and Fulani tribes of Northern Nigeria. J. Ethnopharmacol. 111, 625–629.

    CAS  Article  Google Scholar 

  2. 2.

    Abdulghader, K., Majid, N., Nabat, N. (2008) Chemical stress induced by Heliotrope (Heliotropium europaeum L.) allelochemicals and increased activity of antioxidant enzymes. Pak. J. Biol. Sci. 11, 915–919.

    CAS  Article  Google Scholar 

  3. 3.

    Afef, L., Omezzine, F., Haouala, R. (2014) The impact of tunisian capparidaceae species on cytological, physiological and biochemical mechanisms in lettuce. S. Afr. J. Bot. 93, 222–230.

    Article  Google Scholar 

  4. 4.

    Ali, K. A., Sakri, F. Q., Li, Q. X. (2012) Isolation and purification of allelochemicals from Cephalaria syriaca plant. Int. J. Bio. sci. 2, 90–103.

    CAS  Google Scholar 

  5. 5.

    Arakawa, R., Yamaguchi, M. (2004) Product analysis of caffeic acid oxidation by on-line electrochemistry/electrospray ionization mass spectrometry. J. Am. Soc. Mass. Spectrom. 15, 1228–1236.

    CAS  Article  Google Scholar 

  6. 6.

    Balachadran, C., Veeramuthu, D., Naif, A. A., Balakrishna, K., Nitin, P. K., Vikrant, S. R., Inshad, A. K., Savarimuthu, I. (2012) Antimicrobial and antimycrobacterial activities of methyl caffeate isolated from Solanum torvum Swartz. fruit. Indian J. Microbiol. 4, 676–681.

    Article  Google Scholar 

  7. 7.

    Balachadran, C., Emi, N., Arun, Y., Yamamoto, Y., Ahilan, B., Sangeetha, B., Duraipandiyan, V., Inaguma, Y., Okamoto, A., Ignacimuthu, S., Al-Dhadi, N. A., Perumal, P. T. (2015) In vitro anticancer activity of methyl caffeate isolated from Solanum torvum Swartz. fruit. Chem. Biol. Interact. 242, 81–90.

    Article  Google Scholar 

  8. 8.

    Bailly, F., Robert, A. T., Olympe, T., Nathalie, J., Hubert, H., Philippe, C. (2013) Antiproliferative and apoptotic effects of the oxidative dimerization product of methyl caffeate on human breast cancer cells. Bioorg. Med. Chem. Lett. 23, 574–578.

    CAS  Article  Google Scholar 

  9. 9.

    Das, S., Coku, A. (2014) Allelopathic and antimicrobial evaluation of two Indian weeds–Heliotropium indicum L. and Synedrella nodiflora L. Gaertn with phytochemical studies. Am. J. PharmTech R. 4, 367–377.

    Google Scholar 

  10. 10.

    Dash, G. K., Abdulla, M. S. (2013) A review on Heliotropium indicum L. (Boraginaceae). Int. J. Pharm. Sci. Res. 4.4, 1253–1258.

    Google Scholar 

  11. 11.

    Dayan, F. E., Howell, J., Weidenhamer, J. D. (2009) Dynamic root exudation of sorgoleon and its in planta mechanism of action. J. Exp. Bot. 60.7, 2107–2117.

    Google Scholar 

  12. 12.

    Galinato, M. I., Moody, K., Piggin, C. M. (1999) Upland rice weeds of South and Southeast Asia. Philippines International Rice Research Institute, Makati, Philippines.

    Google Scholar 

  13. 13.

    Gandhi, G. R., Savarimuthu, I., Michael, G. P., Ponnusamy, S. (2011) Antihyperglycemic activity and antidiabetic effect of methyl caffeate isolated from Solanum torvum Swartz. fruit in streptozotocin induced diabetic rats. Eur. J. Pharmacol. 670, 623–631.

    CAS  Article  Google Scholar 

  14. 14.

    Ghori, K. M., Ghaffari, M. A., Hussain, S. N., Manzoor, M., Aziz, M., Sarwer, W. (2016) Ethnopharmacological, phytochemical and pharmacognostic potential of genus Heliotropium L. Turk. J. Pharm. Sci. 13, 259–280.

    CAS  Article  Google Scholar 

  15. 15.

    Inbaraj, J. J., Chignell, C. F. (2004) Cytotoxic action of juglone and plumbagin: a mechanistic study using HaCaT keratinocytes. Chem. Res. Toxicol. 17, 55–62.

    CAS  Article  Google Scholar 

  16. 16.

    Islam, M. S., Kato-Noguchi, H. (2016) Phytotoxicity assessment of Cyperus difformis (L.) towards a sustainable weed management option. J. Anim. Plant Sci. 26, 1765–1771.

    Google Scholar 

  17. 17.

    Kadioglu, I., Yanar, Y. (2004) Allelopathic effects of plant extracts against seed germination of some weeds. Asian J. Plant Sci. 3, 472–475.

    Article  Google Scholar 

  18. 18.

    Kugelman, M., Liu, W. C., Axelrod, M., McBride, T. J., Rao, K. V. (1976) Indicine-N-oxide: the antitumor principle of Heliotropium indicum. Lloydia. 39, 125–128.

    CAS  Google Scholar 

  19. 19.

    Lara-Nunez, A., Romero-Romero, T., Ventura, J. L., Blancas, V., Anaya, A. L., Cruz-Ortega, R. (2006) Allelochemical stress caused inhibition of growth and oxidative damages in Lycopersicon esculentum Mill. Plant, Cell and Environment 29, 2009–2016.

    CAS  Article  Google Scholar 

  20. 20.

    Lee, S. P., Jun, G., Yoon, E., Park, S., Yang, C. (2001) Inhibitory effect of methyl caffeate on Fos-Jun-DNA complex formation and suppression of cancer cell growth. Bull. Korean Chem. Soc., 22.10, 1131–1135.

    Google Scholar 

  21. 21.

    Ma, L., Hongli, W., Ru, B., Li, Z., Xiaohong, Y., Dabin, H. (2011) Phytotoxic effects of Stellera chamaejasme L. root extract. Afr. J. Agric. Res. 6, 1170–1176.

    Google Scholar 

  22. 22.

    Ma, D. W., Wang, Y. N., Wang, Y., Zhang, H., Liao, Y., He, H. (2015) Advance in allelochemical stress induced damage to plant cell. Acta Ecol. Sin. 35, 1640–1645.

    Google Scholar 

  23. 23.

    Prevost, M. S., Delarue-Cochin, S., Marteaux, J., Colas, C., Van, R. C., Blondel, A., Malliavin, T., Corringer, P. J., Joseph, D. (2013) Identification of cinnamic acid derivatives as novel antagonist of the prokaryotic proton-gated ion channel GLIC. J. Med. Chem. 56, 4619–4630.

    CAS  Article  Google Scholar 

  24. 24.

    Pyo, M. K., Yong, Y. L., Hye, Y. C. (2002) Anti-platelet effect of the constituents isolated from the barks and fruits of Magnolia obovate. Arch. Pharm. Res. 25, 325–328.

    CAS  Article  Google Scholar 

  25. 25.

    Reddy, J. S, Rao, P. R., Reddy, M. S. (2002) Wound healing effects of Heliotropium indicum, Plumbago zeylanicum and Acalypha indica in rats. J. Ethnopharmacol. 79, 249–251.

    Article  Google Scholar 

  26. 26.

    Rice, E. L. (1984) Allelopathy, 2nd Ed. Academic Press, Orlando.

    Google Scholar 

  27. 27.

    Suleiman, M. H. A., Banaga, F. A. (2016) Evaluation of allelopathic action of Adansonia digitate L. root extract on the germination and growth of lettuce, hibiscus and sorgum. Int. J. Pharm. Sci. Rev. Res. 37, 137–142.

    CAS  Google Scholar 

  28. 28.

    Vilhena, K. S., Guilhon, G. M., Zoghbi, M. D., Santos, L. S., Souza Filho, A. P. (2014) Chemical investigation of Cyprus distans L. and inhibitory activity of scabequinone in seed germination and seedling growth bioassays. Nat. Prod. Res. 28.23, 2128–2133.

    Google Scholar 

  29. 29.

    Wang, J., Jia, G., Junnan, Z., Jie, P., Tianxing, L., Zhihong, X. (2015) Isolation, identification and antioxidant activity of bound phenolic compounds present in rice bran. Food Chem. 171, 40–49.

    CAS  Article  Google Scholar 

  30. 30.

    Waterhouse, D. F. (1993) The major arthropod pests and weeds of agriculture in southeast Asia: distribution, importance and origin. Brown Prior Anderson, Victoria, Australia.

    Google Scholar 

  31. 31.

    Xiang, M., Hanwen, S., Jinyue, H., Yunjin, Y. (2011) Isolation, identification and determination of methyl caffeate, ethyl caffeate and other phenolic compounds from Polygonum amplexicaule var. sinense. J. Med. Plants Res. 5, 1685–1691.

    CAS  Google Scholar 

  32. 32.

    Zhu, Y., Zhang, L. X., Zhao, Y., Huang, G. D. (2010) Unusual susquiterpene lactones with a new carbon skeleton and new acetylenes from Ajania przewalskii. Food Chem. 118, 228–238.

    CAS  Article  Google Scholar 

Download references

Author information



Corresponding author

Correspondence to Sirinapa Chaipon.

Rights and permissions

This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (, which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Chaipon, S., Suwitchayanon, P., Iwasaki, A. et al. Isolation and Identification of a Growth Inhibitory Substance from Heliotropium indicum L.. BIOLOGIA FUTURA 69, 259–269 (2018).

Download citation

Key words

  • Growth inhibitory effect
  • Heliotropium indicum
  • aqueous methanol extract
  • methyl caffeate
  • growth inhibitory substance