Skip to main content
Log in

Defense on the Rocks: Low Monoterpenoid Levels in Plants on Pillars Without Mammalian Herbivores

  • Published:
Journal of Chemical Ecology Aims and scope Submit manuscript

Abstract

This study addresses the adaptive dynamics of plant toxins that ward off herbivores, an aspect of chemical warfare in ecosystems. Thyme basil (Acinos suaveolens) growing in an area regularly grazed by mammals contains double the concentration of monoterpenoids (15.61 vs. 8.18 mg/g dry matter, P = 0.001) when contrasted with plants growing on inaccessible rock pillars and not exposed to mammalian herbivores. Thyme basil produces two monoterpenoids—menthone and R-(+)-pulegone—that show contrasting toxicity. The more toxic R-(+)-pulegone shows an increase in relative abundance (66.3% vs. 47.5%, P < 0.001) in plants exposed to browsing The results demonstrate how plant chemistry responds to both abiotic and biotic environmental conditions.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  • ANDERSON, I. B., MULLEN, W. H., MEEKER, J. E., KHOJASTEDH-BAKHT, S. C., and BLANC, P. D. 1996. Pennyroyal toxicity: measurement of toxic metabolite levels in two cases and review of the literature. Ann. Intern. Med. 124:726–734.

    PubMed  CAS  Google Scholar 

  • BURBOT, A. J., and LOOMIS, W. D. 1967. Effects of light and temperature on the monoterpenes of peppermint. Plant Physiol. 42:20–28.

    Article  Google Scholar 

  • COULADIS, M., TZAKOU, O., DEMETZOS, C., and PERDETZOGLOU, D. 2002. Chemical composition and antibacterial activity of the oil of Acinos suaveolens (Sibth. et Sm.) G. Don f. from Greece. J. Essent. Oil Res. 14:139–140.

    CAS  Google Scholar 

  • DUNCAN, A. J., REID, S. A., THOSS, V., and ELSTON, D. A. 2005. Browse selection in response to simulated seasonal changes in diet quality through postingestive effects. J. Chem. Ecol. 31:729–744.

    Article  PubMed  CAS  Google Scholar 

  • EMEA 2005. Final public statement on the use of herbal medicinal products containing pulegone and menthofuran. European Agency for the Evaluation of Medicinal Products. Reference EMEA/HMPC/138386/2005.

  • GERSHENZON, J., and DUDAREVA, N. 2007. The function of terpene natural products in the natural world. Nat. Chem. Biol. 3:408–414.

    Article  PubMed  CAS  Google Scholar 

  • GERSHENZON, J., MCCONKEY, M.E., and CROTE, A.U. 2000. Regulation of monoterpene accumulation in leaves of peppermint. Plant Physiol. 122:205–214.

    Article  PubMed  CAS  Google Scholar 

  • GORDON, W. P., FORTE, A. J., MCMURTRY, R. J., GAL, J., and NELSON, S. D. 1982. Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse. Toxicol. Appl. Pharmacol. 65:413–424.

    Article  PubMed  CAS  Google Scholar 

  • LANGENHEIM, J. H. 2003. Plant Resins: Chemistry, Evolution, Ecology and Ethnobotany. Timber, Portland, Cambridge.

    Google Scholar 

  • LATTA, R. G., LINHART, Y. B., LUNDQUIST, L., and SNYDER, M. A. 2000. Patterns of monoterpene variation within individual trees in ponderosa pine. J. Chem. Ecol. 26:1341–1357.

    Article  CAS  Google Scholar 

  • LATTA, R. G., LINHART, Y. B., SNYDER, M. A., and LUNDQUIST, L. 2003. Patterns of variation and correlations in the monoterpene composition of xylem oleoresin within populations of ponderosa pine. Biochem. Syst. Ecol. 31:451–465.

    Article  CAS  Google Scholar 

  • LINCOLN, D. E., and LANGENHEIM, J. H. 1976. Geographic patterns of monoterpenoid composition in Satureja douglasii. Biochem. Syst. Ecol. 4:237–248.

    Article  CAS  Google Scholar 

  • LINCOLN, D. E., and LANGENHEIM, J. H. 1979. Variation of Satureja douglasii monoterpenoids in relation to light intensity and herbivory. Biochem. Syst. Ecol. 7:289–298.

    Article  CAS  Google Scholar 

  • LINCOLN, D. E., and LANGENHEIM, J. H. 1981. A genetic approach to monoterpenoid compositional variation in Satureja douglasii. Biochem. Syst. Ecol. 9:153–160.

    Article  CAS  Google Scholar 

  • MADSEN, C., WURTZEN, G., and CARSTENSEN, J. 1986. Short-term toxicity study in rats dosed with menthone. Toxicol. Lett. 32:147–152.

    Article  PubMed  CAS  Google Scholar 

  • MAHMOUD, S. S., and CROTEAU, R. B. 2003. Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase. Proc. Natl. Acad. Sci. U.S.A. 100:14481–14486.

    Article  PubMed  CAS  Google Scholar 

  • MAFFEI, M., CAMUSSO, W., and SACCO, S. 2001. Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential. Phytochemistry 58:703–707.

    Article  PubMed  CAS  Google Scholar 

  • MCCLANAHAN, R. H., THOMASSE, N. D., SLATTERY, J. T., and NELSON, S. D. 1989. Metabolic activation of (R)-(+)-pulegone to a reactive enonal that covalently binds to mouse liver proteins. Chem. Res. Toxicol. 2:349–355.

    Article  PubMed  CAS  Google Scholar 

  • MCCONKEY, M.E., GERSHENZON, J., and CROTE, A.U. 2000. Development of monoterpene biosynthesis in the glandular trichomes of peppermint. Plant Physiol. 122:215–224.

    Article  PubMed  CAS  Google Scholar 

  • MILEWSKI, A. V., YOUNG, T. P., and MADDEN, D. 1991. Thorns as induced defenses: experimental evidence. Oecologia 86:70–75.

    Article  Google Scholar 

  • MOORTHY, B., MADYASTHA, P., and MADYASTHA, K. M. 1991. Destruction of rat liver microsomal cytochrome P-450 in vitro by a monoterpene ketone, pulegone: A hepatotoxin. Indian J. Chem., Sect. B 30:138–146.

    Google Scholar 

  • OUMZIL, H., GHOULAMI, S., RHAJAOUI, M., ILIDRISSI, A., FKIH-TETOUANI, S., FAID, M., and BENJOUAD, A. 2002. Antibacterial and antifungal activity of essential oils of Mentha suaveolens. Phytother. Res. 16:727–731.

    Article  PubMed  CAS  Google Scholar 

  • PALMER, T. M., STANTON, M. L., YOUNG, T. P., GOHEEN, J. R., PRINGLE, R. M., and KARBAN, R. 2008. Breakdown of an ant-plant mutualism follows the loss of large herbivores from an African savanna. Science 319:192.

    Article  PubMed  CAS  Google Scholar 

  • PULLIN, A. S., and GILBERT, J. E. 1989. The stinging nettle, Urtica dioica, increases trichome density after herbivore and mechanical damage. Oikos 54:275–280.

    Article  Google Scholar 

  • RICE, R. L., LINCOLN, D. E., and LANGENHEIM, J. H. 1978. Palatability of monoterpenoid compositional types of Satureja douglasii to a generalist molluscan herbivore, Ariolimax dolichophallus. Biochem. Syst. Ecol. 6:45–53.

    Article  CAS  Google Scholar 

  • ROHWEDER, A. 1996. Meteora Panoramic Map. Karto Atelier, Forch, Switzerland. ISBN 3-906593-06-1.

    Google Scholar 

  • SJÖDIN, K., OERSSON, M., FÄLDT, J., EKBERG, I., and BORG-KARLSON, A.-K. 2000. Occurrence and correlations of monoterpenes hydrocarbon enantiomers in Pinus sylvestris and Picea abies. J. Chem. Ecol. 26:1701–1720.

    Article  Google Scholar 

  • STUTTE, H. L., and HASSE, D. 1986. Meteora, Greece: Climbing and Hiking. 2nd edn.Stutte, Wolfratshausen, Germany.

    Google Scholar 

  • SULLIVAN, J. B., RUMACK, B. H., THOMAS, H., PETERSON, R. G., and BRYSON, P. 1979. Pennyroyal oil poisoning and hepatotoxicity. J. Am. Med. Assoc. 242:2873–2874.

    Article  Google Scholar 

  • THORUP, I., WURTZEN, G., CARSTENSEN, J., and OLSEN, P. 1983. Short term toxicity study in rats dosed with pulegone and menthol. Toxicol. Lett. 19:207–210.

    Article  PubMed  CAS  Google Scholar 

  • TURNER, G. W., and CROTEAU, R. 2004. Organization of monoterpene biosynthesis in menthe. Immunocytochemical localization of geranyl diphosphate synthase, limonene-6-hydrozylase, isopiperitenol dehydrogenase, and pulegone reductase. Plant Physiol. 136:4215–4227.

    Article  PubMed  CAS  Google Scholar 

  • THOSS, V., O’REILLY-WAPSTRA, J., and IASON, G. R. 2007. Intra-specific and phenological variability in monoterpenes of Scots pine (Pinus sylvestris) foliage: implications for ecological research. J. Chem. Ecol. 33:477–491.

    Article  PubMed  CAS  Google Scholar 

  • VOIRIN, B., BRUN, N., and BAYET, C. 1990. Effects of daylength on the monoterpene composition of leaves of Mentha x piperita. Phytochemistry 29:749–755.

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We thank the rock climbers, notably Dietrich and Ursula Hasse, and Detlef Augustin for their guidance, both in locally facilitating the project and “hands on” leading on the rocks. The Macaulay Institute, Craigiebuckler, Aberdeen AB15 4QH, UK is acknowledged for access to analytical facilities.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Dietland Müller-Schwarze.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Müller-Schwarze, D., Thoss, V. Defense on the Rocks: Low Monoterpenoid Levels in Plants on Pillars Without Mammalian Herbivores. J Chem Ecol 34, 1377–1381 (2008). https://doi.org/10.1007/s10886-008-9543-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10886-008-9543-y

Keywords

Navigation