Abstract
Plants are an extremely rich source of diverse organic compounds which are antifungal. In general, the interest in such antifungal compounds depends upon the concentration required for activity and the biological spectrum of activity. Some of the compounds are preformed and are located in external plant tissues, i.e., bark, peel, and cuticle; others are located throughout the plant, often in vacuoles; and still others are produced by plants in response to physiological stress or infection. In the latter group are the phytoalexins, low molecular weight organic compounds produced by plants in response to infection or stress and localized at the site of infection or stress. This group of compounds is usually lipophilic and includes compounds as diverse as simple phenols, flavonoids, isoflavonoids, coumarins, isocoumarins, sesquiterpenoids, polyenes, stilbenes, furanoterpenoids, and derivatives of these compounds. The levels of still another group of antifungal compounds are enhanced locally and systemically after infection or stress and a second infection often markedly enhances their levels. These are high molecular weight and include chitinases, ß-l,3-glucanases, and thionins. A group of compounds, not directly antifungal, are the structural biopolymers which are localized at sites of infection or stress and which restrict fungal development in plants by forming barriers to fungal development, e.g., lignin, callóse, and hydroxyproline-rich glycoproteins. Even compounds in vacuoles, which would not contact fungi in intact plant cells, can be liberated when cells collapse.
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References
Akazawa, T., 1960. Chromatographic isolation of pure ipomeamarone and reinvestigation of its chemical properties, Archives Biochemistry Acta, 90:82–89.
Akazawa, T., and Wada, K., 1961, Analytical study of ipomeamarone and chlorogenic acid alterations in sweet potato roots infected by Ceratocystis fimbriata, Plant Physiology, 36:139–144.
Allen, E., and Kuc, J., 1968, α-Solanine and α-chaconine as fungitoxic compounds in extracts of Irish potato tubers, Phytopathology, 58:776–781.
Allen, E., and Thomas, C., 1971a, Trans-trans-3,11ridecadiene-5,7,9-triyne-12-diol, an antifungal polyacetylene from diseased safflower (Carthamus tinctorius), Phytochemistry, 10:1579–1582.
Allen, E., and Thomas, C., 1971b, Time course of safynol accumulation in resistant and susceptible safflower infected with Phytophthora drechsleri, Physiological Plant Pathology, 1:235–240.
Allen, E., and Thomas C., 1971c, A second antifungal polyacetylene from Phytophthora-infected safflower, Phytopathology, 6:1107–1109.
Angelí, H. R., Walker, J. C., and Link, K. P., 1930, The relation of protocatechuic acid to disease resistance in onion, Phytopathology, 20:431–438.
Bell, A. A., 1981, Biochemical mechanisms of disease resistance, Annual Review of Plant Physiology, 32:21–81.
Bostock, R. M., Kuc, J., and Laine, R. A., 1981, Eicosapentaenoic and arachidonic acids from Phytophthora infestans elicit fungitoxic sesquiterpenes in potato, Science, 212:67–69.
Bostock, R. M., Laine, R. A., and Kuc, J., 1982, Factors affecting elicitation of sesquiterpenoid phytoalexin accumulation by eicosapentaenoic and arachidonic acids in potato, Plant Physiology, 70:1417–1424.
Burden, R. S., Rowell, P. M., and Bailey, J. A., 1985, Debneyol, a fungicidal sesquiterpene from TNV-infected Nicotiana debneyi, Phytochemistry, 24:2191–2194.
Cartwright, D., Langcake, P., Price, R., Leworthy, D., and Ride, J., 1981, Isolation and characterization of phytoalexins from rice as momilactones A and B, Phytochemistry, 20:535–537.
Chalutz, E., De Vay, J., and Maxie, E., 1969, Ethylene-induced isocoumarin formation in carrot root tissue, Plant Physiology, 44:235–241.
Condon, P., and Kuc, J., 1960, Isolation of a fungitoxic compound from carrot root tissue inoculated with Ceratocystis fimbriata, Phytopathology, 50:267–270.
Condon, P., and Kuc, J., 1962, Confirmation of the identity of a fungitoxic compound produced by carrot root tissue, Phytopathology, 52:182–183.
Condon, P., Kuc, J., and Draudt, H., 1963, Production of 3-methyl-6-methoxy-8-hydroxy-3,4-dihydroisocoumarin by carrot root tissue, Phytopathology, 53:1244–1250.
Coxon, D., Curtis, R., Price, K., and Levett, G., 1973, Abnormal metabolites produced by Daucus carota roots stored under conditions of stress, Phytochemistry, 12:1881–1885.
Coxon, D.T., 1982, Phytoalexins from other families, p. 106–132, in: “Phytoalexins,” J. A. Bailey and J. W. Mansfield, eds., Blackie, Glasgow, London.
Cruickshank, I. A. M., 1963, Phytoalexins, Annual Review of Phytopathology, 1:351–374.
Cruickshank, I., Perrin, D., and Mandryk, M., 1977, Fungitoxicity of duvatrienediols associated with the cuticular wax of tobacco leaves, Phytopathology Zeitschrift, 90:243–249.
Dean, R., and Kuc, J., 1987, Immunization against disease: The plant fights back, p. 383–410, in: “Fungal Infection of Plants,” G. F. Pegg and P. G. Ayres, eds., Cambridge University Press, Cambridge, Massachusetts.
Defago, G., 1982, Genetic analysis of tomatin resistance and pathogenicity of Fusarium solani mutants, p. 324–325, in: “Active Defense Mechanisms in Plants,” R. K. S. Wood, ed., Plenum Press, New York, London.
Dixon, R. and Lamb, C., 1990, Molecular communication in interactions between plants and microbial pathogens, Annual Review of Plant Physiology, 41:339–367.
Doke, N., 1983, Involvement of superoxide anion generation in the hypersensitive response of potato tubers inoculated with Phytophthora infestons and to the hyphal wall components, Physiological Plant Pathology, 23:345–357.
Doke, N., 1985, NADPH-dependent O2” generation in membrane fractions isolated from wounded potato tubers inoculated with Phytophthora infestons, Physiological Plant Pathology, 27:311–322.
Doke, N., Tomiyama, N., and Furuichi, N., 1982, Elicitation and suppression of the hypersensitive response in host-parasite specificity, p. 79–96, in: “Plant Infection: The Physiological and Biochemical Basis,” Y. Asada, W. Bushneil, S. Ouchi, and C. Vance, eds., Japan Scientific Society Press and Springer-Verlag, Tokyo, Berlin.
Doubrava, N., Dean, R., and Kuc, J., 1988, Induction of systemic resistance to anthracnose caused by Colletotrichum lagenarium in cucumber by oxalate and extracts from spinach and rhubarb leaves, Physiological Molecular Plant Pathology, 33:69–80.
Ebel, J., 1986, Phytoalexin synthesis: The biochemical analysis of the induction process, Annual Review of Phytopathology, 24:235–264.
Essenberg, M., Grover, P., and Cover, E., 1990, Accumulation of antibacterial sesquiterpenoids in bacterially inoculated Gossypium leaves and cotyledons, Phytochemistry (in press).
Farih, A., Tsao, P., and Menge, J., 1981, Fungitoxic activity of efosite aluminum on growth, sporulation and germination of Phytophthora parasitica and P. citrophthora, Phytopathology, 71:934–936.
Geigert, J., Stermitz, F., Johnson, G., Maag, D., and Johnson, D., 1973, Two phytoalexins from sugar beet (Beta vulgaris) leaves, Tetrahedron, 29:2703–2706.
Gottstein, D. and Kuc, J., 1989, Induction of systemic resistance to anthracnose in cucumber by phosphates, Phytopathology, 79:176–179.
Hardegger, E., Biland, H., and Corrodi, H., 1963, Synthese von 2,4-dimethoxy-6-hydroxyphenanthren und konstitution des orchinols, Helvetica Chimica Acta, 46:1354–1360.
Harding, V., and Heale, J., 1980, Isolation and identification of the antifungal compound accumulating in the induced resistance response of carrot slices to Botrytis cinerea, Physiological Plant Pathology, 17:277–289.
Hipskind, J., Hanau, R., Leite, B., and Nicholson, R., 1990, Phytoalexin accumulation in sorghum Identification of an apigeninidin acyl ester, Physiological Molecular Plant Pathology, 36:381–396.
Ingham, J. L., 1982, Phytoalexins from the Leguminosae, p. 21–80, in: “Phytoalexins,” J. A. Bailey and J. W. Mansfield, eds., Blackie, Glasgow, London.
Ishizaka, N., and Tomiyama, K., 1972, Effect of wounding or infection by Phytophthora infestons on the contents of terpenoids in potato tubers, Plant and Cell Physiology, 13:1053–1063.
Johnson, C., Brannon, D., and Kuc, J., 1973, Xanthotoxin: A phytoalexin of Pastinica sativa root, Phytochemistry, 12:2961–2962.
Johnson, G., and Schaal, L., 1952, Relation of chlorogenic acid to scab resistance in potatoes, Science, 115:627–629.
Johnson, G., and Schaal, L., 1955, The inhibitory effect of phenolic compounds on growth of Streptomyces scabies as related to the mechanisms of scab resistance, Phytopathology, 45:626–628.
Keene, C. K., and Wagner, G. J., 1985, Direct demonstration of duvatrienediol biosynthesis in glandular heads of tobacco trichomes, Plant Physiology, 79:1026–1032.
Kuc, J., 1957, A biochemical study of the resistance of potato tuber to attack by various fungi, Phytopathology, 47:676–680.
Kuc, J., 1972, Phytoalexins, Annual Review of Phytopathology, 10:207–232.
Kuc, J., 1982, Phytoalexins from the Solanaceae, p. 81–105, in: “Phytoalexins,” J. A. Bailey and J. W. Mansfield, eds., Blackie, Glasgow, London.
Kuc, J., 1983, Induced systemic resistance in plants to diseases caused by fungi and bacteria, p. 191–221, in: “The Dynamics of Host Defense,” J. Bailey and B. Deverall, eds., Academic Press, Sydney, Australia.
Kuc, J., 1987, Plant immunization and its applicability for disease control, p. 255–274, in: “Innovative Approaches to Plant Disease Control,” I. Chet, ed., John Wiley and Son, New York, New York.
Kuc, J., 1990a, Immunization for the control of plant disease, p. 355–373, in: “Biological Control of Soil Borne Plant Pathogens,” D. Hornby, ed., CAB International, Wallingford, United Kingdom.
Kuc, J., 1990b, A case for self defense in plants, Phytoparasitica, 18(1):3–7.
Kuc, J., and Caruso, F., 1977, Activated coordinated chemical defense against disease in plants, p. 78–89, in: “Host Resistance to Pests,” P. Hedin, ed., American Chemical Society Press, Washington, D.C.
Kuc, J., and Preisig, C., 1984, Fungal regulation of disease resistance mechanisms in plants, Mycologia, 76(5):767–784.
Kuc, J., and Rush, J., 1985, Phytoalexins, Archives of Biochemistry and Biophysics, 236:379–389.
Kuc, J., and Tuzun, S., 1983, Immunization for disease control in tobacco, Recent Advances in Tobacco Science, 9:179–213.
Langcake, P., 1981, Alternative chemical agents for controlling plant diseases, Philosophical Transactions of the Royal Society of London B Biological Sciences 295:83–101.
Langcake, P., Cornford, C., and Pryce, R., 1979, Identification of pterostilbene as a phytoalexin from Vitus vinifera leaves, Phytochemistry, 18:1025–1027.
Langcake, P., and Pryce, R., 1977a, A new class of phytoalexins from grapevines, Experientia, 33:151–152.
Langcake, P., and Pryce, R., 1977b, The production of resveratrol and the viniferins by grapevines in response to ultraviolet irradiation, Phytochemistry, 16:1193–1196.
Leppik, R., Holloman, D., and Bottomly, W., 1972, Quiesone: An inhibitor of germination of Peronospora tabacina conidia, Phytochemistry, 11:2055–2063.
Link, K. P., Dickson, A. D. and Walker, J. C., 1929, Further observations on the occurrence of protocatechuic acid in pigmented onion scales and its relation to disease resistance in the onion, Journal of Biological Chemistry, 84:719–725.
Link, K. P., and Walker, J. C., 1933, The isolation of catechol from pigmented onion scales and its significance in relation to disease resistance in onions, Journal of Biological Chemistry, 100:379–383.
Locci, R., and Kuc, J., 1967, Steroid glycoalkaloids as compounds produced by potato tubers under stress, Phytopathology, 57:1272–1273.
McKee, R., 1955, Host-parasite relationship in the dry rot disease of potatoes, Annals of Applied Biology, 43:147–148.
McKee, R., 1959, Factors affecting the toxicity of solanine and related alkaloids to Fusarium caeruleum, Journal of General Microbiology, 20:686–696.
Overeem, J. C., 1976, Pre-existing antimicrobial substances in plants and their role in disease resistance, p. 195–206, in: “Biochemical Aspects of Plant-Parasite Relationships,” J. Friend and D. R. Threlfall, eds., Academic Press, London, England.
Preisig, C., and Kuc, J., 1985, Arachidonic acid-related elicitors of the hypersensitive response in potato and enhancement of their activities by glucans from Phytophthora infestons, Archives of Biochemistry and Biophysics, 236:379–389.
Preisig, C. L., and Kuc, J., 1987, Phytoalexins, elicitors, enhancers, suppressors and other considerations in the regulation of R-gene resistance to Phytophthora infestons in potato, p. 203–221, in: “Biochemical and Molecular Determinants of Plant Diseases,” S. Nishimura, C. Vance, and N. Doke, eds., Japan Scientific Society Press, Tokyo.
Rao, N., and Kuc, J., 1991, Induced systemic resistance in plants, p. 347–362, in: “The Fungal Spore and Disease Initiation in Plants and Animals,” G. T. Cole and H. C. Hoch, eds., Plenum Press, New York, New York.
Rao, M. N., Siegel, M. R., Ferriss, R. S., Nesmith, W. C., Wiglesworth, M. D., Burton, H. R., Reuveni, M., Tuzun, S., and Kuc, J., 1989a, Relationships between susceptibility of field-grown burley tobacco to blue mold and contents of duvatrienediols, Phytopathology, 79:267–270.
Rao, M. N., Siegel, M. R., Nielsen, M. T., Wiglesworth, M. D., Burton, H. R., and Kuc, J., 1989b, Evaluation and induction of resistance to blue mold in tobacco genotypes differing in contents of duvatrienediols, Phytopathology, 79:271–275.
Reuveni, M., Tuzun, S., Cole, J., Siegel, M., and Kuc, J., 1986a, Removal of duvatriendiols from the surfaces of tobacco leaves increases their susceptibility to blue mold, Physiological Molecular Plant Pathology, 30:44–51.
Reuveni, M., Tuzun, S., Cole, J., Siegel, M., and Kuc, J., 1986b, The effects of plant age and leaf position on the susceptibility of tobacco to blue mold caused by Peronospora tabacina, Phytopathology, 76:455–458.
Salt, S., Tuzun, S., and Kuc, J., 1986, Effects of ß-ionone and abscisic acid on the growth of tobacco and resistance to blue mold, Physiological and Molecular Plant Pathology, 28:287–297.
Salt, S., Reuveni, M., and Kuc, J., 1988, Inhibition of Peronospora tabacina (blue mold of tobacco) and related plant pathogens in vitro and in vivo by esters of 3(R)-hydroxy-β-ionone, 42nd Tobacco Chemists Conference Proceedings, Tobacco Chemists Society, Lexington, Kentucky, p. 22.
Severson, R. F., Johnson, A. W., and Jackson, D. M., 1985, Cuticular constituents of tobacco: Factors affecting their production and their role in insect and disease resistance and smoke quality, Recent Advances in Tobacco Science, 11:105–174.
Shih, M. J., 1972, The accumulation of isoprenoids and phenols and their control as related to the interaction of potato (Solanum tuberosum) with Phytophthora infestons, Ph.D. Thesis, Purdue University, Lafayette, Indiana.
Shih, M., and Kuc, J., 1973, Incorporation of 14C from acetate and mevalonate into rishitin and steroid glycoalkaloids by potato slices inoculated with Phytophthora infestons, Phytopathology, 63:826–829.
Shih, M., and Kuc, J., 1974, α- and β-Solarmarine in Kennebec Solanum tuberosum leaves and aged tuber slices, Phytopathology, 13:997–1000.
Shih, M., Kuc, J., and Williams, E. B., 1973, Suppression of steroid glycoalkaloid accumulation as related to rishitin accumulation in potato tubers, Phytopathology, 63:821–826.
Sitton, D., and West, C., 1975, Casbene: An antifungal diterpene produced in cell-free extracts of Ricinus communis seedlings, Phytopathology, 14:1921–1925.
Smith, D., 1982, Toxicity of phytoalexins, p. 218–252, in: “Phytoalexins,” J. A. Bailey, and J. W. Mansfield, eds., Blackie, Glasgow, London.
Stoessl, A., 1982, Biosynthesis of phytoalexins, p. 133–180, in: “Phytoalexins,” J. A. Bailey and J. W. Mansfield, eds., Blackie, Glasgow, London.
Stoessl, A., 1983, Secondary plant metabolites in preinfectional and postinfectional resistance, p. 71–122, in: “The Dynamics of Host Defense,” J. A. Bailey and B. J. Deverall, eds., Academic Press, Sydney, Australia.
Sutton, D., 1979, Systemic cross protection in bean against Colletotrichum lindemuthianum, Australasia Plant Pathology, 8:4–5.
Takasugi, M., Nagao, S., Masamune, T., Shirata, A., and Takahashi, K., 1978, Structure of moracin A and B, new phytoalexins from diseased mulberry, Tetrahedron Letters, 34:797–798.
Tjamos, E. C., and Kuc, J., 1982, Inhibition of steroid glycoalkaloid accumulation by arachidonic and eicosapentaenoic acids in potato, Science, 217:542–544.
Tuzun, S., and Kuc, J., 1989, Induced systemic resistance to blue mold, p. 177–200, in: “Blue Mold of Tobacco,” W. E. McKeen, ed., American Phytopathological Society, St. Paul, Minnesota.
Tuzun, S., Nesmith, W., Ferriss, R., and Kuc, J., 1986, Effects of stem injections with Peronospora tabacina on growth of tobacco and protection against blue mold in the field, Phytopathology, 76:938–941.
Tuzun, S., Reuveni, M., Siegel, M., and Kuc, J., 1989, The effect of removing leaf surface components with acetone from immunized and nonimmunized resistant tobacco plants on their susceptibility to blue mold, Phytopathology, 79:1024–1027.
Tzeli, J., Melcher, U., and Essenberg, M., 1988, Inactivation of cauliflower mosaic virus by a photoactivatable cotton phytoalexin, Physiological Molecular Plant Pathology, 33:115–126.
Tzeli, J., Essenberg, M., and Melcher, U., 1989, Photoactivated DNA nicking, enzyme inactivation and bacterial inhibition by sesquiterpenoid phytoalexins from cotton, Molecular Plant-Microbe Interactions, 2:139–147.
Urech, J., Fesctig, B., Nuesch, J., and Vischer, E., 1963, Hircinol, eine antifungisch wirksame Substanz ans knollen von Loroglossum hircinum (L.) Rich, Helvetica Chimica Acta, 46:2758–2766.
Uritani, I., Uritani, M., and Yamada, H., 1960, Similar metabolic alterations induced in sweet potato by poisonous chemicals and by Ceratocystis fimbriata, Phytopathology, 50:30–34.
VanEtten, H., Matthews, D., and Matthews, P., 1989, Phytoalexin detoxification Importance for pathogenicity and practical implications, Annual Review of Phytopathology, 27:143–164.
Zook, M., and Kuc, J., 1990, Elicitation of sesquiterpenoid cyclase and suppression of squalene synthetase activity in potato tuber tissue, Phytopathology, 80:1009 (Abstract).
Zook, M., Rush, J., and Kuc, J., 1987, A role for Ca2+ in the elicitation of rishitin and lubimin accumulation in potato tuber tissue, Plant Physiology, 84:520–525.
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Kuc, J. (1992). Antifungal Compounds from Plants. In: Nigg, H.N., Seigler, D. (eds) Phytochemical Resources for Medicine and Agriculture. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-2584-8_7
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