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Part of the book series: The Families and Genera of Vascular Plants ((FAMILIES GENERA,volume 13))

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Abstract

Compared to many other angiosperms, the grasses are not noted for the diversity of their secondary compounds. However, as indicated below, this may simply reflect lack of investigation. A wide range of secondary compounds is reported, but in general the data come from a handful of taxa that are particularly important for grazing or field crops; the taxonomic distribution of most compounds is thus largely unknown. Secondary compounds may be produced by roots or by above ground tissue, and production may be constitutive, or be triggered by herbivore attack, or be produced in response to the presence of particular bacteria or fungi. Of the 2400 species in a database of plants with pest-control properties (Grainge and Ahmed 1988), about 50 are grasses; documentation of the chemicals produced by these plants and their effects on other organisms varies considerably in quality. Compounds produced in response to pathogens are sometimes called phytoalexins, a term that refers to their inducibility rather than their chemical composition. A number of grass species harbor fungal endophytes that produce secondary compounds that serve as plant defense; in this case the defense compound is in fact a product of the fungus rather than the plant. Finally, cell walls in the grasses have a distinctive chemical composition; whether it is adaptive in any way is unknown. The material presented here is not intended to be a comprehensive review, but will provide some hint of the phytochemical diversity to be explored in the family.

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References

  • Bais, H.P., Weir, T.L., Perry, L.G., Gilroy, S., Vivanco, J.M. 2006. The role of root exudates in rhizosphere interactions with plants and other organisms. Ann. Rev. Plant Biol. 57: 233–266.

    Article  CAS  Google Scholar 

  • Belz, R.G. 2007. Allelopathy in crop/weed interactions. Pest Manag. Sci. 63: 308–326.

    Article  CAS  PubMed  Google Scholar 

  • Bertin, C., Weston, L.A., Huang, T., Jander, G., Owens, T., Meinwald, J., Schroeder, F.C. 2007. Grass roots chemistry: meta-tyrosine, an herbicidal nonprotein amino acid. Proc. Natl. Acad. Sci. 104: 16964–16969.

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  • Chagonda, L.S., Makanda, C., Chalchat, J.-C. 2000. The essential oils of wild and cultivated Cymbopogon validus (Stapf) Stapf ex Burtt Davy and Elionurus muticus (Spreng.) Kunth from Zimbabwe. Flavour Fragrance J. 15: 100–104.

    Article  CAS  Google Scholar 

  • Chen, W., Viljoen, A.M. 2010. Geraniol - a review of a commercially important fragrance material. South Afr. J. Bot. 76: 643–651.

    Article  CAS  Google Scholar 

  • Chong, J., Poutaraud, A., Hugueney, P. 2009. Metabolism and roles of stilbenes in plants. Plant Sci. 177: 143–155.

    Article  CAS  Google Scholar 

  • Comfort, N.C. 2001. The tangled field: Barbara McClintock’s search for the patterns of genetic control. Cambridge, Massachusetts: Harvard University Press.

    Google Scholar 

  • Culvenor, R.A., Reed, K.F.M., McDonald, S.E. 2005. Comparative levels of dimethyltryptamine- and tyramine-related alkaloid toxins in Australian cultivars and some wild populations of Phalaris aquatica. Aust. J. Agric. Res. 56: 1395–1403.

    Article  CAS  Google Scholar 

  • Czarnota, M.A., Paul, R.N., Dayan, F.E., Nimbal, C.I., Weston, L.A. 2001. Mode of action, localization of production, chemical nature, and activity of sorgoleone: a potent PSII inhibitor in Sorghum spp. root exudate. Weed Technol. 15: 813–825.

    Article  CAS  Google Scholar 

  • Czarnota, M.A., Paul, R.N., Weston, L.A., Duke, S.O. 2003. Anatomy of sorgoleone-secreting root hairs of Sorghum species. Int. J. Plant Sci. 164: 861–866.

    Article  Google Scholar 

  • Darbyshire, S.J., Pavlick, L.E. 2007. Festuca L. In: Barkworth, M.E., Capels, K.M., Long, S., Anderton, L.K., Piep, M.B. (eds.) Flora of North America north of Mexico. Vol. 24. Magnoliophyta: Commelinidae (in part): Poaceae, part 1. New York: Oxford University Press. pp. 389–443

    Google Scholar 

  • Del Giudice, L., Massardo, D.R., Pontieri, P., Bertea, C.M., Mombello, D., Carata, E., Tredici, S.M., Tala, A., Mucciarelli, M., Groudeva, V.I., De Stefano, M., Vigliotta, G., Marrei, M.E., Alifano, P. 2008. The microbial community of vetiver root and its involvement into essential oil biogenesis. Environ. Microbiol. 10: 2824–2841.

    Article  PubMed  Google Scholar 

  • Dick, R., Rattei, T., Haslbeck, M., Schwab, W., Gierl, A., Frey, M. 2012. Comparative analysis of benzoxazinoid biosynthesis in monocots and dicots: independent recruitment of stabilization and activation functions. Plant Cell 24: 915–928.

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  • Duke, S.O. 2007. The emergence of grass root chemical ecology. Proc. Natl. Acad. Sci. 104: 16729–16730.

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  • Edgar, J.A. 1994. Toxins in temperate grasses - implications and solutions. N. Z. J. Agric. Res. 37: 341–347.

    Article  Google Scholar 

  • Escribano-Bailón, M.T., Santos-Buelga, C., Rivas-Gonzalo, J.C. 2004. Anthocyanins in cereals. J. Chromatog. A 1054: 129–141.

    Article  Google Scholar 

  • Field, B., Osbourn, A.E. 2008. Metabolic diversification - independent assembly of operon-like gene clusters in different plants. Science 320: 543–547.

    Article  CAS  PubMed  Google Scholar 

  • Fossen, T., Slimestad, R., Øvstedal, D.O., Andersen, Ø.M. 2002. Anthocyanins of grasses. Biochem. Syst. Ecol. 30: 855–864.

    Article  CAS  Google Scholar 

  • Gibson, D.J. 2009. Grasses and grassland ecology. New York: Oxford University Press.

    Google Scholar 

  • Glinwood, R., Pettersson, J., Ahmed, E., Ninkovic, V., Birkett, M., Pickett, J. 2003. Change in acceptability of barley plants to aphids after exposure to allelochemicals from couch-grass (Elytrigia repens). J. Chem. Ecol. 29: 261–274.

    Article  CAS  PubMed  Google Scholar 

  • Gorz, H.J., Haskins, F.A., Dam, R., Vogel, K.P. 1979. Dhurrin in Sorghastrum nutans. Phytochemistry 18: 2024.

    Article  CAS  Google Scholar 

  • Grainge, M., Ahmed, S. 1988. Handbook of plants with pest-control properties. New York: Wiley.

    Google Scholar 

  • Grimmett, R.E., Waters, D.F. 1943. A fluorescent alkaloid in ryegrass (Lolium perenne L.) II. Extraction from fresh ryegrass and separation from other bases. N. Z. J. Sci. Technol. Sect. B 24: 151–155.

    Google Scholar 

  • Grotewold, E. (ed.) 2006. The science of flavonoids. New York: Springer.

    Google Scholar 

  • Grün, S., Frey, M., Gierl, A. 2005. Evolution of the indole alkaloid biosynthesis in the genus Hordeum: Distribution of gramine and DIBOA and isolation of the benzoxazinoid biosynthesis genes from Hordeum lechleri. Phytochemistry 66: 1264–1272.

    Article  PubMed  Google Scholar 

  • Harborne, J.B., Williams, C.A. 1987. Flavonoid patterns of grasses. In: Soderstrom, T.R., Hilu, K.W., Campbell, C.S., Barkworth, M.E. (eds.) Grass systematics and evolution. Washington, DC: Smithsonian Institution Press. pp. 107–113

    Google Scholar 

  • Harborne, J.B., Williams, C.A. 2000. Advances in flavonoid research since 1992. Phytochemistry 55: 481–504.

    Article  CAS  PubMed  Google Scholar 

  • Hasegawa, M., Mitsuhara, I., Seo, S., Imai, T., Koga, J., Okada, K., Yamane, H., Ohashi, Y. 2010. Phytoalexin accumulation in the interaction between rice and the blast fungus. Mol. Plant-Microbe Interact. 23: 1000–1011.

    Article  CAS  PubMed  Google Scholar 

  • Haskins, F.A., Gorz, H.J. 1985. Dhurrin and p-hydroxybenzaldehyde in seedlings of various Sorghum species. Phytochemistry 24: 597–598.

    Article  CAS  Google Scholar 

  • Inda, L.A., Segarra-Moragues, J.G., Müller, J., Peterson, P.M., Catalán, P. 2008. Dated historical biogeography of the temperate Loliinae (Poaceae, Pooideae) grasses in the northern and southern hemispheres. Mol. Phyl. Evol. 46: 932–957.

    Article  CAS  Google Scholar 

  • Ishihara, A., Hashimoto, Y., Miyagawa, H., Wakasa, K. 2008. Induction of serotonin accumulation by feeding of rice striped stem borer in rice leaves. Plant Signaling Behav. 3: 714–716.

    Article  Google Scholar 

  • Jensen, K., Osmani, S.A., Hamann, T., Naur, P., Møller, B.L. 2011. Homology modeling of the three membrane proteins of the dhurrin metabolon: catalytic sites, membrane surface association and protein-protein interactions. Phytochemistry 72: 2113–2123.

    Article  CAS  PubMed  Google Scholar 

  • Joy, R.J. Undated. “Sunshine” Vetivergrass Chrysopogon zizanioides (L.) Roberty. USDA-NRCS Plant Guide.

    Google Scholar 

  • Khan, Z.R., Midega, C.A.O., Bruce, T.J.A., Hooper, A.M., Pickett, J.A. 2010. Exploiting phytochemicals for developing a ‘push-pull’ crop protection strategy for cereal farmers in Africa. J. Exp. Bot. 61: 4185–4196.

    Article  CAS  PubMed  Google Scholar 

  • Kobayashi, T., Nishizawa, N.K. 2012. Iron uptake, translocation, and regulation in higher plants. Ann. Rev. Plant Biol. 63: 131–152.

    Article  CAS  Google Scholar 

  • Kong, C., Liang, W., Xu, X., Hu, F., Wang, P., Jiang, Y. 2004. Release and activity of allelochemicals from allelopathic rice seedlings. J. Agric. Food Chem. 52: 2861–2865.

    Article  CAS  PubMed  Google Scholar 

  • Koulman, A., Seeliger, C., Edwards, P.J.B., Fraser, K., Simpson, W., Johnson, L., Cao, M., Rasmussen, S., Lane, G.A. 2008. E/Z-Thesinine-O-4′-alpha-rhmanoside, pyrrolizidine conjugates produced by grasses (Poaceae). Phytochemistry 69: 1927–1932.

    Article  CAS  PubMed  Google Scholar 

  • Larsson, K.A.E., Zetterlund, I., Delp, G., Jonsson, L.M.V. 2006. N-methyltransferase involved in gramine biosynthesis in barley: cloning and characterization. Phytochemistry 67: 2002–2008.

    Article  CAS  PubMed  Google Scholar 

  • Larsson, K.A.E., Saheed, S.A., Gradin, T., Delp, G., Karpinska, B., Botha, C.E.J., Jonsson, L.M.V. 2011. Differential regulation of 3-aminomethylindole/N-methyl-3-aminomethylindole N-methyltransferase and gramine in barley by both biotic and abiotic stress. Plant Physiol. Biochem. 49: 96–102.

    Google Scholar 

  • Ma, J.F. 2005. Plant root responses to three abundant soil minerals: silicon, aluminum and iron. Crit. Rev. Plant Sci. 24: 267–281.

    Article  CAS  Google Scholar 

  • Maffei, M. 2002. Introduction to the genus Vetiveria. In: Maffei, M. (ed.) The genus Vetiveria. London: Taylor & Francis.

    Chapter  Google Scholar 

  • McMullen, M.D., Frey, M., Degenhardt, J. 2009. Genetics and biochemistry of insect resistance in maize. In: Bennetzen, J.L., Hake, S.C. (eds.) Handbook of Maize: Its Biology. New York: Springer. pp. 271–289

    Chapter  Google Scholar 

  • Mevy, J.P., Bessiere, J.-M., Dherbomez, M., Viano, J. 2002. Composition and some biological activities of the essential oils from an African pasture grass: Elionurus elegans Kunth. J. Agric. Food Chem. 50: 4240–4243.

    Article  CAS  PubMed  Google Scholar 

  • Morohashi, K., Casas, M.I., Ferreyra, L.F., Mejia-Guerra, M.K., Pourcel, L., Yilmaz, A., Feller, A., Carvalho, B., Emiliani, J., Rodriguez, E., Pellegrinet, S., McMullen, M., Casati, P., Grotewold, E. 2012. A genome-wide regulatory framework identifies maize Pericarp Color1 controlled genes. Plant Cell 24: 2745–2764.

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  • Murata, Y., Ma, J.F., Yamaji, N., Ueno, D., Nomoto, K., Iwashita, T. 2006. A specific transporter for iron(III)-phytosiderophore in barley roots. Plant J. 46: 563–572.

    Google Scholar 

  • Nielsen, K.A., Tattersall, D.B., Jones, P.R., Møller, B.L. 2008. Metabolon formation in dhurrin biosynthesis. Phytochemistry 69: 88–98.

    Article  CAS  PubMed  Google Scholar 

  • Osbourn, A.E. 2003. Saponins in cereals. Phytochemistry 62: 1–4.

    Article  CAS  PubMed  Google Scholar 

  • Papadopoulou, K., Melton, R.E., Leggett, M., Daniels, M.J., Osbourn, A.E. 1999. Compromised disease resistance in saponin-deficient plants. Proc. Natl. Acad. Sci. 96: 12923–12928.

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  • Paterson, A.H., Bowers, J.E., Bruggmann, R., Dubchak, I., Grimwood, J., Gundlach, H., Haberer, G., Hellsten, U., Mitros, T., Poliakov, A., Schmutz, J., Spannagl, M., Tang, H., Wang, X., Wicker, T., Bharti, A.K., Chapman, J., Feltus, F.A., Gowik, U., Grigoriev, I.V., Lyons, E., Maher, C.A., Martis, M., Narechania, A., Otillar, R.P., Penning, B.W., Salamov, A.A., Wang, Y., Zhang, L., Carpita, N.C., Freeling, M., Gingle, A.R., Hash, C.T., Keller, B., Klein, P., Kresovich, S., McCann, M.C., Ming, R., Peterson, D.G., Mehboob-ur-Rahman, Ware, D., Westhoff, P., Mayer, K.F.X., Messing, J., Rokhsar, D.S. 2009. The Sorghum bicolor genome and the diversification of grasses. Nature 457: 551–556.

    Google Scholar 

  • Peters, R.J. 2006. Uncovering the complex metabolic network underlying diterpenoid phytoalexin biosynthesis in rice and other cereal crop plants. Phytochemistry 67: 2307–2317.

    Article  CAS  PubMed  Google Scholar 

  • Peters, R.J. 2010. Two rings in them all: the labdane-related diterpenoids. Nat. Prod. Rep. 27: 1521–1530.

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  • Poulton, J.E. 1990. Cyanogenesis in plants. Plant Phys. 94: 401–405.

    Article  CAS  Google Scholar 

  • Prasad, K.V.S.K., Song, B.-H., Olson-Manning, C., Anderson, J.T., Lee, C.-R., Schranz, M.E., Windsor, A.J., Clauss, M.J., Manzaneda, A.J., Naqvi, I., Reichelt, I.M., Gershenzon, J., Rupasinghe, S.G., Schuler, M.A., Mitchell-Olds, T. 2012. A gain-of-function polymorphism controlling complex traits and fitness in nature. Science 337: 1081–1084.

    Article  CAS  PubMed  Google Scholar 

  • Prashar, A., Hili, P., Veness, R.G., Evans, C.S. 2003. Antimicrobial action of palmarosa oil (Cymbopogon martinii) on Saccharomyces cerevisiae. Phytochemistry 63: 569–575.

    Article  CAS  PubMed  Google Scholar 

  • Qi, X., Bakht, S., Leggett, M., Maxwell, C., Melton, R., Osbourn, A. 2004. A gene cluster for secondary metabolism in oat: implications for the evolution of metabolic diversity in plants. Proc. Natl. Acad. Sci. USA 101: 8233–8238.

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  • Rodríguez Quintanilla, R., Ruiz Nova, C., Arias Moyano, G., Castro Salazar, H., Martínez, J., Stashenko, E. 2012. Comparative study of the essential oil compositions of four Cymbopogon (Poaceae) species grown in Colombia. Bol. Latinamer. Caribe Plantas Medicin. Aromat. 11: 77–85.

    Google Scholar 

  • Römheld, V., Marschner, H. 1986. Evidence for a specific uptake system for iron phytosiderophores in roots of grasses. Plant Phys. 80: 175–180.

    Article  Google Scholar 

  • Schaaf, G., Ludewig, U., Erenoglu, B.E., Mori, S., Kitahara, T., Wiren, N.V. 2004. ZmYs1 functions as a proton-coupled symporter for phytosiderophore- and nicotianamine-chelated metals. J. Biol. Chem. 279: 9091–9096.

    Article  CAS  PubMed  Google Scholar 

  • Schardl, C.L., Leuchtmann, A., Chung, K.-R., Penny, D., Siegel, M.R. 1997. Coevolution by common descent of fungal symbionts (Epichloë spp.) and grass hosts. Mol. Biol. Evol. 14: 133–143.

    Article  CAS  Google Scholar 

  • Schardl, C.L., Leuchtmann, A., Spiering, M.J. 2004. Symbioses of grasses with seedborne fungal endophytes. Ann. Rev. Plant Biol. 55: 315–340.

    Article  CAS  Google Scholar 

  • Schardl, C.L., Grossman, R.B., Nagabhyru, P., Faulkner, J.R., Mallik, U.P. 2007. Loline alkaloids: currencies of mutualism. Phytochemistry 68: 980–996.

    Article  CAS  PubMed  Google Scholar 

  • Selmar, D., Irandoost, Z., Wray, V. 1996. Dhurrin-6′-glucoside, a cyanogenic diglucoside from Sorghum bicolor. Phytochemistry 43: 569–572.

    Article  CAS  PubMed  Google Scholar 

  • Shimura, K., Okada, A., Okada, K., Jikumaru, Y., Ko, K.-W., Toyomasu, T., Sassa, T., Hasegawa, M., Kodama, O., Shibuya, N., Koga, J., Nojiri, H., Yamane, H. 2007. Identification of a biosynthetic gene cluster in rice for momilactones. J. Biol. Chem. 282: 34013–34018.

    Article  CAS  PubMed  Google Scholar 

  • Sicker, D., Frey, M., Schulz, M., Gierl, A. 2000. Role of natural benzoxazinones in the survival strategy of plants. Int. Rev. Cytol. 198: 319–346.

    Article  CAS  PubMed  Google Scholar 

  • Spatafora, J.W., Sung, G.-H., Sung, J.-M., Hywel-Jones, N.L., White, Jr., J.F. 2007. Phylogenetic evidence for an animal pathogen origin of ergot and the grass endophytes. Mol. Ecol. 16: 1701–1711.

    Article  CAS  PubMed  Google Scholar 

  • Sue, M., Nakamura, C., Nomura, T. 2011 Dispersed benzoxazinone gene cluster: molecular characterization and chromosomal localization of glucoxyltransferase and glucosidase genes in wheat and rye. Plant Phys. 157: 985–997.

    Article  CAS  Google Scholar 

  • Tanaka, Y., Sasaki, N., Ohmiya, A. 2008. Biosynthesis of plant pigments: anthocyanins, betalains and carotenoids. Plant J. 54: 733–749.

    Article  CAS  PubMed  Google Scholar 

  • Tattersall, D.B., Bak, S., Jones, P.R., Olsen, C.E., Nielsen, J.K., Hansen, M.L., Høj, P.B., Møller, B.L. 2001. Resistance to an herbivore through engineered cyanogenic glucoside synthesis. Science 293: 1826–1828.

    Article  CAS  PubMed  Google Scholar 

  • Toyomasu, T., Kagahara, T., Okada, K., Koga, J., Hasegawa, M., Mitsuhashi, W., Sassa, T., Yamane, H. 2008. Diterpene phytoalexins are biosynthesized in and exuded from the roots of rice seedings. Biosci. Biotech. Biochem. 72: 562–567.

    Article  CAS  Google Scholar 

  • Ueno, D., Rombola, A.D., Iwashita, T., Nomoto, K., Ma, J.F. 2007. Identification of two novel phytosiderophores secreted by perennial grasses. New Phytol. 174: 304–310.

    Article  CAS  PubMed  Google Scholar 

  • Umemura, K., Ogawa, N., Shimura, M., Koga, J., Usami, H., Kono, T. 2003. Possible role of phytocassane, rice phytoalexin, in disease resistance of rice against blast fungus Magnaporthe grisea. Biosci. Biotech. Biochem. 67: 899–902.

    Article  CAS  Google Scholar 

  • White, Jr., J.F., Bacon, C.W., Hywel-Jones, N.L., Spatafora, J.W. 2003. Historical perspecitives: human interactions with clavicipitalean fungi. In: White, Jr., J.F., Bacon, C.W., Hywel-Jones, N.L., Spatafora, J.W. (eds.) Clavicipitalean fungi: evolutionary biology, chemistry, biocontrol, and cultural impacts. New York: Marcel Dekker, Inc. pp. 1–14

    Chapter  Google Scholar 

  • Xiao, Y., Wang, Q., Erb, M., Turlings, T.C.J., Ge, L., Hu, L., Li, J., Han, X., Zhang, T., Lu, J., Zhang, G., Lou, Y. 2012. Specific herbivore-induced volatiles defend plants and determine insect community composition in the field. Ecol. Lett. 15: 1130–1139.

    Article  CAS  PubMed  Google Scholar 

  • Xu, M., Galhano, R., Wiemann, P., Bueno, E., Tiernan, M., Wu, W., Chung, I.-M., Gershenzon, J., Tudzynski, B., Sesma, A., Peters, R.J. 2012. Genetic evidence for natural product-mediated plant-plant allelopathy in rice (Oryza sativa). New Phytol. 193: 570–575.

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  • Xuan, T.D., Chung, I.M., Khanh, T.D., Tawata, S. 2006. Identification of phytotoxic substances from early growth of barnyard grass (Echinochloa crusgalli) root exudates. J. Chem. Ecol. 32: 895–906.

    Article  CAS  PubMed  Google Scholar 

  • Yu, C.K.Y., Springob, K., Schmidt, J., Nicholson, R.L., Chu, I.K., Yip, W.K., Lo, C. 2005. A stilbene synthase gene (SbSTS1) is involved in host and nonhost defense responses in sorghum. Plant Phys. 138: 393–401.

    Article  CAS  Google Scholar 

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Kellogg, E.A. (2015). Phytochemistry. In: Flowering Plants. Monocots. The Families and Genera of Vascular Plants, vol 13. Springer, Cham. https://doi.org/10.1007/978-3-319-15332-2_8

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