Journal of Chemical Ecology

, Volume 31, Issue 7, pp 1657–1668 | Cite as

Potential Allelochemicals from an Invasive Weed Mikania micrantha H.B.K.

  • Hua Shao
  • Shaolin Peng
  • Xiaoyi Wei
  • Deqing Zhang
  • Chi ZhangEmail author


Phytotoxicity-directed extraction and fractionation of the aerial parts of Mikania micrantha H.B.K. led to the isolation and identification of three sesquiterpenoids: dihydromikanolide, deoxymikanolide, and 2,3-epoxy-1-hydroxy-4,9-germacradiene-12,8:15,6-diolide. These sesquiterpenoids inhibited both germination and seedling growth of tested species with deoxymikanolide possessing the strongest phytotoxicity. In a bioassay against lettuce (Lectuca sativa L.), deoxymikanolide reduced radicle elongation at low concentration (IC50 = 47 μg/ml); dihydromikanolide showed a weaker effect (IC50 = 96 μg/ml), and 2,3-epoxy-1-hydroxy-4,9-germacradiene-12,8:15,6-diolide exhibited the least effect (IC50 = 242 μg/ml). Deoxymikanolide caused yellowish lesions at the root tips of lettuce at a concentration of 50 μg/ml, and a 250 μg/ml solution killed lettuce seedlings. A bioassay against the monocot ryegrass (Lolium multiforum) revealed similar results on radicle elongation, which implied that the growth inhibition by these compounds was not selective. To evaluate their phytotoxicity to plants in natural habitats, three common companion tree species in south China, Acacia mangium, Eucalyptus robusta, and Pinus massoniana, were also tested and similar results were obtained. This is the first report on the isolation of 2,3-epoxy-1-hydroxy-4,9-germacradiene-12,8:15,6-diolide as a naturally occurring product.

Key Words

Phytotoxicity allelochemical Mikania micrantha exotic species dihydromikanolide deoxymikanolide 2,3-epoxy-1-hydroxy-4 9-germacradiene-12,8: 15,6-diolide. 


  1. Anaya, A. L., Mata, R., Rivero-Cruz, F., HernÁndez-Bautista, B. E., ChÁvez-Velasco, D., GÓmez-Pompa, A. 1999Allelochemical potential of Metopium brownieJ. Chem. Ecol.25141157Google Scholar
  2. Bagchi, G. D., Jain, D. C., Kumar, S. 1997Arteether: a potent plant growth inhibitor from Artemisia annuaPhytochemistry4511311133Google Scholar
  3. Barreto, R. W., Evans, H. C. 1995The mycobiota of the weed Mikania micrantha in southern Brazil with particular reference to fungal pathogens for biological controlMycol. Res.99343352Google Scholar
  4. Cock, M. J. W. 1982The biology and host specificity of Liothrips mikaniae (Presner) (Thysanoptera: Phlaeothripidae), a potential biological control agent of Mikania micrantha (Compositae)Bull. Entomol. Res.72523533Google Scholar
  5. Cock, M. J. W., Ellison, C. A., Evans, H. C., Ooi, P. A. C. 2000Can failure be turned into success for biological control of mile-a-minute weed (Mikania micrantha)?Spencer, N. R. eds. Proceedings of the Xth International Symposium on Biological Control of Weeds. 4–14 July 1999Montana State UniversityMontana, USA155167Google Scholar
  6. Cuenca, M. D. A., Bardon, A., Catalan, C. A. N. 1988Sesquiterpene lactones from Mikania micranthaJ. Nat. Prod.51625626Google Scholar
  7. He, L. P., Liang, Q. Y., Yang, R. H., Xu, S. D. 2000An exotic weed: Mikania micrantha—its distribution and harmfulness in ShenzhenFor. Technol. Guangdong163841Google Scholar
  8. Hedge, R. S., Miller, D. A. 1992Scanning electron microscopy for studying root morphology and anatomy in alfalfa autotoxicityAgron. J.84618620Google Scholar
  9. Herz, W., Subramaniam, P. S., Santhanam, P. S., Aota, K., Hall, A. L. 1970Structure elucidation of sesquiterpene dilactones from Mikania scandens (L.) WilldJ. Org. Chem.3514531464PubMedGoogle Scholar
  10. Holm, L. G., Plucknett, D. L., Pancho, J. V., Herberger, J. P. 1977The World’s Worst Weeds: Distribution and BiologyThe University Press of HawaiiHonolulu609 ppGoogle Scholar
  11. Inderjit, , Weston, L. A. 2000Are laboratory bioassays for allelopathy suitable for prediction of field responses?J. Chem. Ecol.2621112118Google Scholar
  12. Ismail, B. S., Chong, T-V. 2002Effects of aqueous extracts and decomposition of Mikania micrantha H.B.K. debris on selected agronomic cropsWeed Biol. Manage.23138Google Scholar
  13. Ismail, B. S., Mah, L. S. 1993Effects of Mikania micrantha H.B.K. on germination and growth of weed speciesPlant Soil157107113Google Scholar
  14. Kamo, T., Hiradate, S., Fujii, Y. 2003First isolation of natural cyanamide as a possible allelochemical from hairy vetchJ. Chem. Ecol.29275283PubMedGoogle Scholar
  15. Kong, G. H., Wu, Q. G., Hu, Q. M., Ye, W. H. 2000Further supplementary data on Mikania micrantha H.B.K. (Asteraceae)J. Trop. Subtrop. Botany8128130Google Scholar
  16. Lan, C. Y., Wang, Y. J. 2001Studies on the Natural Resources and Ecology of Neilingding Island in GuangdongForestry Press of ChinaBeijingGoogle Scholar
  17. Macias, F. A., Torres, A., Molinillo, J. M. G., Castellano, D. 1996Potential allelopathic sesquiterpene lactones from sunflower leavesPhytochemistry4312051215Google Scholar
  18. Macias, F. A., Galindo, J. C. G., Molinillo, J. M. G., Castellano, D. 2000Dehydrozaluzanin C: A potent plant growth regulator with potential use as a natural herbicide templatePhytochemistry54165171PubMedGoogle Scholar
  19. Parker, C. 1972The Mikania problemPest Artic. News Summ.18312315Google Scholar
  20. Quayyum, H. A., Mallik, A. U., Lee, P. F. 1999Allelopathic potential of aquatic plants associated with wild rice (Zizania palustris): I. Bioassay with plant and lake sediment samplesJ. Chem. Ecol.25209221Google Scholar
  21. Romeo, J. T. 2000Raising the beam: Moving beyond phytotoxicityJ. Chem. Ecol.2620112014Google Scholar
  22. Viles, A. L., Reese, R. N. 1995Allelopathic potential of Echinacea angustifolia D.C.Environ. Exp. Bot.363943Google Scholar

Copyright information

© Springer Science + Business Media, Inc. 2005

Authors and Affiliations

  • Hua Shao
    • 1
  • Shaolin Peng
    • 1
  • Xiaoyi Wei
    • 1
  • Deqing Zhang
    • 2
  • Chi Zhang
    • 1
    • 3
    Email author
  1. 1.South China Institute of BotanyChinese Academy of SciencesGuangzhouChina
  2. 2.Gluck Research CenterUniversity of KentuckyLexingtonUSA
  3. 3.School of Forestry and Wildlife SciencesAuburn UniversityAuburnUSA

Personalised recommendations