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(1S,2R,4S,5S)-angelicoidenol-2-o-β-d-glucopyranoside—A moose deterrent compound in Scots pine (Pinus sylvestris L.)

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Abstract

Hydrophilic extracts of Scots pine (Pinus sylvestris L.) twigs have been investigated for palatability to moose in feeding experiments. The predominant repellent effect was observed from the 2-O-β-d-glucopyranoside of the monoterpene (1S,2R,4S,5S)-angelicoidenol. Of other isolated and tested substances, only taxifolin-3′-O-β-d-glucopyranoside had a deterring effect. One fraction-containing mainly aliphatic compounds-also had a strong effect, but the effect was lost after further fractionation. Tannin-containing fractions had no effect. Angelicoidenol glucoside has not previously been reported fromP. sylvestris. The results are discussed in view of phenols as defense compounds.

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References

  • Ahlén, I. 1968. Research on moose vegetation in Scandinavia, pp. 23–34,in Proceedings of the Fifth North American Moose Workshop, Keani, Alaska, 1968.

  • Ahlén, I. 1975. Winter habitats of moose and deer in relation to land and use in Scandinavia.Viltrevy (Swedish Wildlife) 9:170–192 (in Swedish).

    Google Scholar 

  • Allen, M.S., Darby, N., Salisbury, P., Sigurdson, E.R., andMoney, T. 1979. Chemical and microbiological remote functionalisation of (+)- and (−)-bornyl acetate.Can. J. Chem. 57:733–741.

    Google Scholar 

  • Anderson, R., andLundgren, L.N. 1988. Monoaryl and cyclohexanone glucosides from needles ofPinus sylvestris.Phytochemistry 27:559–562.

    Google Scholar 

  • Bryant, J.P., Wieland, G.D., Reichardt, P.B., Lewis, V.E., andMcCarthy, M.C. 1983. Pinosyivin methyl ether deters snowshoe hare feeding on green alder.Science 222:1023–1025.

    Google Scholar 

  • Cederlund, G., Ljungkvist, H., Markgrem, G., andStålfelt, F. 1980. Foods of moose and roe deers at Grismö in central Sweden. Results of ruman content analysis.Swed. Wildl. Res. 11:169–247.

    Google Scholar 

  • Clausen, T.P., Reichardt, P.B., andBryant, J.P. 1986. Pinosyivin and pinosyivin methyl ether as feeding deterrents in green alder.J. Chem. Ecol. 12:2117–2131.

    Google Scholar 

  • Danell, K., Gref, R., andYasdani, R. 1990. Effects of mono- and diterpenes in Scots pine needles on moose browsing.Scand. J. For. Res. 5:236–240.

    Google Scholar 

  • Dev, S. 1989. Isoprenoids, pp. 691–807,in J.W. Rowe, (ed.). Natural Products of Woody Plants II, Springer-Verlag, Berlin.

    Google Scholar 

  • Enzell, C., andTheander, O. 1962. The constituents of conifer needles II. Pinifolic acid, a new diterpene acid isolated fromPinus sylvestris L.Ada Chem. Scand. 16:607–614.

    Google Scholar 

  • Feeny, P. 1970. Seasonal changes in oak leaf tannins and nutrients as a cause of spring feeding by winter moth caterpillars.Ecology 51:565–581.

    Google Scholar 

  • Feeny, P. 1976. Plant apparancy and chemical defense.Recent Adv. Phytochem. 10:1–40.

    Google Scholar 

  • Fujioka, S., Kashara, F., andShiraki, M. 1988. Bornane derivates and pharmaceuticals containing them.Jpn. Kokai Tokkyo Koho Jp 63, 290,892;Chem. Abstr. 111:219268n.

    Google Scholar 

  • Gref, R. 1981. Variation in isoabienol content inPinus sylvestris needles.Can. J. Bot. 59:831–835.

    Google Scholar 

  • Gref, R. 1987. Resin acids and resistance ofPinus sylvestris to Melampsora pinitorqua.Eur. J. For. Pathol. 4–5:227–230.

    Google Scholar 

  • Gunawardana, Y.A.G.P., andCordell, G.A. 1988. (−)-5-exo-Hydroxyborneol: Isolation and NMR spectral assignments.J. Nat. Prod. 51:142–143.

    Google Scholar 

  • Gupta, R.J., andHaslam, E. 1981. Plant proanthocyanidins. Part 7. Prodelphinidins fromPinus sylvestris.J. Chem. Soc, Perkin Trans. 1:1148–1150.

    Google Scholar 

  • Häggman, J., andRousi, M. 1985. Relationship between the repellent substances of Scots pine and browsing by mountain hare.Aquilo, Ser. Bot. 23:69–74.

    Google Scholar 

  • Harborne, J. 1985. Phenolics and plant defence.Annu. Proc. Phytochem. Soc. Eur.25:393–408.

    Google Scholar 

  • Haslam, E. 1988. Plant polyphenols (syn. vegetable tannins) and chemical defense—a reappraisal.J. Chem. Ecol. 14:1789–1805.

    Google Scholar 

  • Haukioja, E., Huopalahti, R., Kotiahoja, J., andNygren, K. 1983. Millaisia männyntaimia hirvi suosii?Suom. Riista 30:22–27.

    Google Scholar 

  • Inoshiri, S., Saiki, M., Kohda, H., Otsuka, H., andYamasaki, K. 1988. Monoterpene glucosides fromBerchemia racemosa.Phytochemistry 27:2869–2871.

    Google Scholar 

  • Kamiya, S., Konishi, F., andEsaki, S. 1974. Structure and bitterness in flavanone glycosides.Agric. Biol. Chem. 38:1785–1790.

    Google Scholar 

  • Löyttiniemi, K. 1981. Nitrogen fertilization and nutrient contents in Scots pine in relation to browsing preference by moose (Alces alces).Folia For. 487:12–14.

    Google Scholar 

  • Löyttiniemi, K., andHiltonen, R. 1978. Monoterpenes in Scots pine in relation to browsing preference by moose (Alces alces L.).Silva Fenn. 12:85–87.

    Google Scholar 

  • Lundgren, L. 1987. Studies on low-molecular phenolic constituents in conifer needles. Thesis. Department of Chemistry, Swedish University of Agricultural Sciences, Upsala.

    Google Scholar 

  • Lundgren, L.N., andTheander, O. 1988.cis- andtrans-Dihydroquercetin glucosides in fiavonoids from needlesof Pinus sylvesris.Phytochemistry 27:829–832.

    Google Scholar 

  • Lundgren, L.N., Popoff, T., andTheander, O. 1982. Arylglycerol glucosides fromPinus sylvestris.Acta Chem. Scand. B 36:695–699.

    Google Scholar 

  • Mahmood, U., Singh, S.B., andThakur, R.S. 1983. Angelicoidenol, a bicyclic monoterpene from the seeds ofPleurospermeum angelicoides.Phytochemistry 22:774–776.

    Google Scholar 

  • Marquet, A., andGabard, J. 1967. Stéréochemie de quelques dérivés du campane.Bull. Chim. Soc. Fr. 00:128–129.

    Google Scholar 

  • Neimann, G.J. 1979. Some aspects of the chemistry ofPinaceae needles.Acta Bot. Neerl. 28:73–88.

    Google Scholar 

  • Niemann, G.J., andVan Genderen, H. 1980. Chemical relationship between Pineceae.Biochem. Syst. Ecol. 8:237–240.

    Google Scholar 

  • Niemelä, P., andDanell, K. 1988. Comparison of moose browsing on Scots pine (Pinus sylvestris) and lodgepole pine (P. contorta).J. Appl. Ecol. 25:761–775.

    Google Scholar 

  • Norin, T., 1972. Some aspects of the chemistry of order Pinales.Phytochemistry 11:1231–1242.

    Google Scholar 

  • Palo, T. 1984. Distribution of birch (Betula spp.), willow (Salix spp.), and poplar (Populus spp.) secondary metabolites and their potential role as chemical defense against herbivores.J. Chem. Ecol. 10:499–520.

    Google Scholar 

  • Popoff, T., andTheander, O. 1975. Two glycosides of a new dilignol fromPinus sylvestris.Phytochemistry 14:2065–2066.

    Google Scholar 

  • Popoff, T., andTheander, O. 1976. Phenolic glycosides fromPinus sylvestris L.Appl. Polym. Symp. 28:1341–1347.

    Google Scholar 

  • Popoff, T., andTheander, O. 1977. The constituents of conifer needles VI. Phenolic glycosides fromPinus sylvestris.Acta Chem. Scand. 31B:329–337.

    Google Scholar 

  • Robbins, C.T., Hanley, T.A., Hagerman, A., Hjeljord, O., Baker, D.L., Schwartz, C.C., andMautz, W. 1987. Role of tannins in defending plants against ruminants: Reduction in protein availability.Ecology 68:98–107.

    Google Scholar 

  • Strack, D., Heilemann, J., Wray, V., andDirks, H. 1989. Structures and accumulation patterns of soluble and insoluble phenolics from Norway spruce needles.Phytochemistry 28:2071–2078.

    Google Scholar 

  • Sunnerheim, K., Palo, R.T., Theander, O., andKnutsson, P.G. 1988. Chemical defense in birch. Platyphylloside: A phenol fromBetula pendula inhibiting digestibility.J. Chem. Ecol. 14:549–560.

    Google Scholar 

  • Sunnerheim-Sjöberg, K., andHämäläinen, M. 1992. Multivariate study of moose browsing on pines in relation to phenol pattern.J. Chem. Ecol. 18:659–672.

    Google Scholar 

  • Sunnerheim-Siöberg, K.,Eriksson, G.,Lundgren, L.N., andTheander, O. 1992. Inheritance of three flavonoid glucosides in needles ofPinus sylvestris L.Scand. J. For. Res. In press.

  • Sweeley, C., Bentley, R., Makita, M., andWells, W. 1963. Gas-liquid chromatography of trimethylsilyl derivatives of sugars and related substances.J. Am. Chem. Soc. 85:2497–2507.

    Google Scholar 

  • Theander, O. 1982. Hydrophilic extractives from the needles of Scots pine and Norway spruce.Sven. Papperstidn, 85:R64–68.

    Google Scholar 

  • Theander, O., andLundgren, L.N. 1989. Monoaryl natural products, pp. 369–399, in J.W. Rowe, (ed.). Natural Products of Woody Plants I. Springer-Verlag, Berlin.

    Google Scholar 

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  1. Department of Chemistry, Swedish University of Agricultural Sciences, P.O. Box 7015, S-750 07, Uppsala, Sweden

    Kerstin Sunnerheim-Sjöberg

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Sunnerheim-Sjöberg, K. (1S,2R,4S,5S)-angelicoidenol-2-o-β-d-glucopyranoside—A moose deterrent compound in Scots pine (Pinus sylvestris L.). J Chem Ecol 18, 2025–2039 (1992). https://doi.org/10.1007/BF00981925

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