Plant Growth Regulation

, Volume 68, Issue 2, pp 171–175 | Cite as

Organ-specific-active allelopathic substance in red pine needles

  • Hisashi Kato-Noguchi
  • Yoshiko Fushimi
  • Fukiko Kimura
  • Maho Morita
  • Kiyotake Suenaga
Original Paper


An organ-specific-growth inhibitory substance was isolated from an aqueous methanol extract of red pine needles and determined by spectral data as 1-mono(16-hydroxyhexadecanoyl)glycerol. This substance inhibited root growth of cress (Lepidium sativum L.) and barnyard grass (Echinochloa crus-galli (L.) Beauv) seedlings at concentrations greater than 0.01 and 0.03 μM, respectively. The concentrations required for 50 % growth inhibition on roots of cress and barnyard grass were 0.16 and 3.4 μM, respectively. However, the inhibitory activity of the substance on shoots of cress and barnyard grass was very weak. The endogenous concentration of 1-mono(16-hydroxyhexadecanoyl)glycerol in the pine needles was 4.6 μmol kg−1. Two related compounds, 1-monohexadecanoylglycerol and 16-hydroxyhexadecanlic acid had no activity up to 1,000 μM on cress roots and shoots. The effectiveness of 1-mono(16-hydroxyhexadecanoyl)glycerol on root growth inhibition and the occurrence of 1-mono(16-hydroxyhexadecanoyl)glycerol in pine needles suggest the substance may play an important role in the allelopathy of red pine. Root-specific-growth-inhibition by the substance may be one of the strategies for red pine to compete with neighboring plants for nutrients and space because root growth of competitive plants may be very important for their whole plant development.


Allelopathy Phytoalexin Pinaceae Pine forest Growth inhibitor 


  1. Bais HP, Weir TL, Perry LG, Gilroy S, Vivanco JM (2006) The role of root exudates in rhizosphere interactions with plants and other organisms. Annu Rev Plant Biol 57:233–266PubMedCrossRefGoogle Scholar
  2. Belz RG (2007) Allelopathy in crop/weed interactions—an update. Pest Manag Sci 63:308–326PubMedCrossRefGoogle Scholar
  3. Caboun V (2006) Tree-tree allelopathic interactions in middle European forests. Allelopathy J 17:17–31Google Scholar
  4. Chu-Chou M (1978) Effects of root residues on growth of Pinus radiata seedlings and a mycorrhizal fungus. Ann Appl Biol 90:407–416CrossRefGoogle Scholar
  5. Dayan FE, Duke SO (2009) Biological activity of allelochemicals. In: Osbourn AE, Lanzotti V (eds) Plant-derived natural products: synthesis, function, and application. Springer, New York, pp 361–384CrossRefGoogle Scholar
  6. Duke SO, Dayan FE, Romagni JG, Rimando AM (2000) Natural products as sources of herbicide, current status and future trends. Weed Res 40:99–111CrossRefGoogle Scholar
  7. Einhellig FA (1999) An integrated view of allelochemicals amid multiple stresses. In: Inderjit, Dakshini KMM, Foy CL (eds) Principals and practices in plant ecology: allelochemical interactions. CRC Press, Boca Raton, pp 479–494Google Scholar
  8. Fernandez C, Lelong B, Vila B, Mévy JP, Robles C, Greff S, Dupouyet S, Bousquet-Mélou A (2006) Potential allelopathic effect of Pinus halepensis in the secondary succession: an experimental approach. Chemoecology 16:97–105CrossRefGoogle Scholar
  9. Fernandez C, Voiriota S, Mévya JP, Vilaa B, Ormeñoa B, Dupouyeta S, Bousquet-Méloua A (2008) Regeneration failure of Pinus halepensis Mill.: the role of autotoxicity and some abiotic environmental parameters. For Ecol Manag 255:2928–2936CrossRefGoogle Scholar
  10. Graça J, Schreiber L, Rodrigues J, Pereira H (2002) Glycerol and glyceryl esters of ω-hydroxyacids in cutins. Phytochemistry 61:205–215PubMedCrossRefGoogle Scholar
  11. Harris MR, Lamb D, Erskine PD (2003) An investigation into the possible inhibitory effects of white cypress pine (Callitris glaucophylla) litter on the germination and growth of associated ground cover species. Aust J Bot 51:93–102CrossRefGoogle Scholar
  12. Inderjit (1996) Plant phenolics in allelopathy. Bot Rev 62:186–202Google Scholar
  13. Jia L, Zhai M, Feng C (2003) Effects of allelopathic substances on the growth and photosynthesis of Pinus tabulaeformis seedlings. J Beijing For Univ 25:6–10Google Scholar
  14. Kato-Noguchi H, Fushimi Y, Shigemori H (2009) An allelopathic substance in red pine needles (Pinus densiflora). J Plant Physiol 166:442–446PubMedCrossRefGoogle Scholar
  15. Kato-Noguchi H, Fushimi Y, Tanaka Y, Teruya T, Suenaga K (2011) Allelopathy of red pine: isolation and identification of an allelopathic substance in red pine needles. Plant Growth Regul 65:299–304CrossRefGoogle Scholar
  16. Kil BS, Yim YJ (1983) Allelopathic effects of Pinus densiflora on undergrowth of red pine forest. J Chem Ecol 9:1135–1151CrossRefGoogle Scholar
  17. Kim KW, Kim KU (2000) Searching for rice allelochemicals. In: Kim KU, Shin DH (eds) Rice allelopathy. Kyungpook National University, Korea, pp 83–95Google Scholar
  18. Lee IK, Monsi M (1963) Ecological studies on Pinus densiflora forest 1. Effects of plant substances on the floristic composition of the undergrowth. Bot Mag 76:400–413Google Scholar
  19. Lodhi MAK, Killingbeck KT (1982) Effects of pine-produced chemicals on selected understory species in a Pinus ponderosa community. J Chem Ecol 8:275–283CrossRefGoogle Scholar
  20. Nektarios PA, Economou G, Avgoulas C (2005) Allelopathic effects of Pinus halepensis needles on turfgrasses and biosensor plants. HortSci 40:246–250Google Scholar
  21. Node M, Tomita-Yokotani K, Suzuki T, Kosemura S, Hirata H, Hirata K, Nawamaki T, Yamamura S, Hasegawa K (2003) Allelopathy of pinecone in Japanese red pine tree (Pinus densiflora Sieb. et Zucc.). Weed Biol Man 3:111–116CrossRefGoogle Scholar
  22. Putnam AR (1988) Allelochemicals from plants as herbicides. Weed Technol 2:510–518Google Scholar
  23. Rice EL (1984) Allelopathy, 2nd edn. Academic Press, OrlandoGoogle Scholar
  24. Rimando AM, Duke SO (2003) Studies on rice allelochemicals. In: Smith CW, Dilday RH (eds) Rice; origin, history, technology and production. Wiley, New York, pp 221–244Google Scholar
  25. Romagni JG, Allen SN, Dayan FE (2000) Allelopathic effects of volatile cineoles on two weedy plant species. J Chem Ecol 26:303–313CrossRefGoogle Scholar
  26. Seigler DS (1996) Chemistry and mechanisms of allelopathic interactions. Agron J 88:876–885CrossRefGoogle Scholar
  27. Son DS, Eon TJ, Seo JD, Lee SR (1996) A study on resistant substance to pine needle gall midge among phenolic compounds in pine needles. J Korean Forry Soc 85:372–380Google Scholar

Copyright information

© Springer Science+Business Media B.V. 2012

Authors and Affiliations

  • Hisashi Kato-Noguchi
    • 1
  • Yoshiko Fushimi
    • 1
  • Fukiko Kimura
    • 1
  • Maho Morita
    • 2
  • Kiyotake Suenaga
    • 2
  1. 1.Department of Applied Biological Science, Faculty of AgricultureKagawa UniversityMikiJapan
  2. 2.Department of Chemistry, Faculty of Science and TechnologyKeio UniversityKohokuJapan

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