Abstract
Many metabolites are produced in small quantities by a limited number of species and do not appear to be essential for the growth and reproduction of the producing organisms. These compounds have been termed secondary metabolites. The interrelationship between primary metabolism and biosynthesis of some secondary metabolites is given in Fig. 9-1. All secondary metabolites are derived from intermediates of primary metabolism. Thus, biosynthetic pathways of secondary metabolites are extensions and branches of primary pathways. Consequently, the distinction between primary and secondary metabolism is not always clear. For example, terpenoid phytoalexins are generally considered to be secondary metabolites, yet they are synthesized via the same pathways from which many essential metabolites are derived. These metabolites include membrane sterols and growth regulators like gibberellins and abscisic acid.
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References
Adesanya SA, Ogundana SK, Roberts MF (1989) Dihydrostilbene phytoalexins from Dioscorea bulbifera and D. dumentorum. Phytochemistry 28: 773–774
Adrian M, Jeandet P, Bessis R, Joubert JM (1996) Induction of phytoalexin (resveratrol) synthesis in grapevine leaves treated with aluminum chloride (AICI3). J Agric Food Chem 44: 1979–1981
Afek U, Sztejnberg A (1988) Accumulation of scoparone, a phytoalexin associated with resistance of citrus to Phytophthora citrophthora. Phytopathology 78: 1678–1682
Afek U, Sztejnberg A (1993) Temperature and gamma irradiation effects on scoparone, a citrus phytoalexin conferring resistance to Phytophthora citrophthora. Phytopathology 83: 753–758
Afek U, Sztejnberg A (1995) Scoparone (6,7-dimethoxycoumarin), a Citrus phytoalexin involved in resistance to pathogens. In Daniel M, Purkayastha RP (eds) Handbook of phytoalexin metabolism and action. Macel Dekker, New York, pp 263–286
Afek U, Carmeli S, Aharoni N (1995) Columbianetin, a phytoalexin associated with celery resistance to pathogens during storage. Phytochemistry 39: 1347–1350
Akatsuka T, Kodama O, Kato H, Kono Y, Takeuchi S (1983) 3-Hydroxy-7-oxo-sandraracopimaradiene (oryzalexin A), a new phytoalexin isolated from rice blast leaves. Agric Biol Chem 47: 445–447
Alami I, Clérivet A, Naji M, Van Munster M, Macheix JJ (1999) Elicitation of Platanus x acerifolia cell suspension cultures induces the synthesis of xanthoarnol, a dihydrofuranocoumarin phytoalexin. Phytochemistry 51: 733–736
Al-Douri NA, Dewick PM (1986) Biosynthesis of the furanoacetylene phytoalexin wyerone in Vicia faba. Z Naturforsch 41c: 34–38
Allen EH, Thomas CA (1971 a) Trans-trans-3,1 I-tridecadiene-5,7,9-triyne-1,2-diol, an antifungal polyacetylene from diseased safflower (Carthamus linctorius). Phytochemistry 10: 1579–1582
Allen EH, Thomas CA (197 1 b) A second antifungal polyacetylene from Phytophthora-infected safflower. Phytopathology 61: 1107–1109
Ames BN, Gold LS (1989) Pesticides, risk and applesauce. Science 244: 755–757
Amin M, Kurosaki F, Nishi A (1988) Carrot phytoalexin alters the membrane permeability of Candida albicans and multilamellar liposomes. Gen J Microbiol 134: 241–246
Anderson AJ (1989) The biology of glycoproteins as elicitors. In: Kosuge T, Nester EW (eds) Plant-microbe interactions, vol 3. McGraw-Hill, New York, pp 87–130
Arase S, Yoshiura Y, Ozoe Y, Honda Y, Nozu M (1996) Production of a phytoalexin, sakuranetin, in the Sekiguchi lesion on rice cv. Sekiguchi-asahi. Ann Phytopathol Soc Japan 62: 408–410
Ayer WA, Craw PA, Ma Y-T, Miao S (1992) Synthesis of camalexin and related phytoalexins. Tetrahedron 48: 2919–2924
Ayers AR, Ebel.1, Valent B, Albersheim P (1976a) Host-pathogen interactions. X. Fractionation and biological activity of an elicitor isolated from the mycelial walls of Phytophthora megasperma var. sojae. Plant Physiol 57: 760–765
Ayers AR, Valent B, Ebel J, Albersheim P (1976b) Host-pathogen interactions. XI. Composition and structure of wall-released elicitor fractions. Plant Physiol 57: 766–774
Ayers AR, Ebel J, Finelli F, Berger N, Albersheim P (1976c) Host-pathogen interactions. IX. Quantitative assays of elicitor activity and characterization of the elicitor present in the extracellular medium of cultures of Phytophthora megasperma var. sojae. Plant Physiol 57: 751–759
Bailey JA (1973) Production of antifungal compounds in cowpea (Vigna sinensis) and pea (Pisum sativum) after virus infection. J Gen Microbiol 75: 119–123
Bailey IA, Burden RS (1973) Biochemical changes and phytoalexin accumulation in Phaseolus vulgaris following cellular browning caused by tobacco necrosis virus. Physiol Plant Pathol 3: 171–177
Bailey JA, Mansfield JW (1982) Phytoalexins. John Wiley and Sons, New York, 334 pp
Bailey JA, Burden RS, Vincent GG (1975) Capsidiol: an antifungal compound produced in Nicotiana tabacum and N. clevelandii following infection with tobacco necrosis virus. Phytochemistry 14: 597
Bailey JA, Burden RS, Mynett A, Brown C (1977) Metabolism of phaseol lin by Septoria nodorum and other non-pathogens of Phaseolus vulgaris. Phytochemistry 16: 1541–1544
Barz W, Mackenbrock U (1994) Constitutive and elicitation induced metabolism of isoflavones and pterocarpans in chickpea (Cicer arietinum) cell suspension cultures. Plant Cell, Tissue and Organ Culture 38: 199–211
Barz W, Bless W, Daniel S, Gunia W, Hinderer W, Jaques U, Kessmann H, Meier D, Tiemann K, Wittkampf U (1989) Elicitation and suppression of isoflavones and pterocarpan phytoalexins in chickpea (Cicer arietinum) cell cultures. In: Kurz WGW (ed) Primary and secondary metabolism of plant cell cultures II. Springer-Verlag, Berlin, pp 208–218
Beier RC, Oertli EH (1983) Psoralen and other linear furocoumarins as phytoalexins in celery. Phytochemistry 22: 2595–2597
Bell AA, Stipanovic RD, Zhang J, Mace ME, Reibenspies JH (1998) Identification and synthesis of trinorcadalene phytoalexins formed by Hibiscus cannabinus. Phytochemistry 49: 431–440
Benedict CR, Alchanati 1, Harvey PJ, Liu JG, Stipanovic RD, Bell AA (1995) The enzymatic formation of S-cadinene from farnesyl diphosphate in extracts of cotton. Phytochemistry 39: 327–331
Bennett MH, Gallagher MDS, Bestwick CS, Rossiter JT, Mansfield JW (1994) The phytoalexin response of lettuce to challenge by Botrytis cinerea, Bremia lactucae and Pseudomonas syringae pv. phaseolicola. Physiol Mol Plant Pathol 44: 321–333
Bestwick L, Bennett MH, Mansfield JW, Rossiter JT (1995) Accumulation of the phytoalexin lettucenin A and changes in 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in lettuce seedlings with the red spot disorder. Phytochemistry 39: 775–777
Biggs DR (1975) Post-infectional compounds from the French bean, Phaseolus vulgaris: isolation and identification ofgenistein and 2’,4’,5,7-tetrahydroxyisotlavone. Aust J Chem 28: 1389–1392
Binks RH, Greenham JR, Luis JG, Gowen SR (1997) A phytoalexin from roots of Musa acuminata var. Pisang sipulu. Phytochemistry 45: 47–49
Blein J-P, Milat M-L, Ricci P (1991) Responses of cultured tobacco cells to cryptogein, a proteinaceous elicitor from Phytophthora cryptogea. Possible plasmalemma involvement. Plant Physiol 95: 486–491
Bless W, Barz W (1988) Isolation of pterocarpan synthase, the terminal enzyme of pterocarpan phytoalexin biosynthesis in cell suspension cultures of Cicer arietinum. FEBS Lett 235: 47–50
Bloch CB, De Wit PJGM, Kuc J (1984) Elicitation of phytoalexins by arachidonic and eicosapentaenoic acids: a host survey. Physiol Plant Pathol 25: 199–208
Blount JW, Dixon RA, Paiva NL (1992) Stress responses in alfalfa (Medicago sativa L.) XVI. Antifungal activity of medicarpin and its biosynthetic precursors; implications for the genetic manipulation of stress metabolites. Physiol Mol Plant Pathol 41: 333–349
Bonde MR, Miller RL, Ingham.1L (1973) Induction and identification of sativan and vestitol as two phytoalexins from Lotus corniculatus. Phytochemistry 12: 2957–2959
Bostock RM, Kué JA, Laine RA (1981) Eicosapentaenoic and arachidonic acids from Phytophthora infestans elicit fungi toxic sesquiterpenes in the potato. Science 212: 67–69
Boydston R, Paxton JD, Koeppe DE (1983) Glyceollin: A site-specific inhibitor of electron transport in isolated soybean mitochondria. Plant Physiol 72: 151–155
Bruegger BB, Keen NT (1979) Specific elicitor of glyceollin accumulation in the Pseudomonas glycinea-soybean host-parasite system. Physiol Plant Pathol 15: 43–51
Brindle PA, Kuhn Pi, Threlfall DR (1988) Biosynthesis and metabolism of sesquiterpenoid phytoalexins and triterpenoids in potato cell suspension cultures. Phytochemistry 27: 133–150
Brinker AM, Seigler DS (1991) Isolation and identification of piceatannol as a phytoalexin from sugarcane. Phytochemistry 30: 3229–3232
Brinker AM, Seigler DS (1993) Time course of piceatannol accumulation in resistant and susceptible sugarcane stalks after inoculation with Colletotrichum falcatum. Physiol Mol Plant Pathol 42: 169–176
Brooks CJW, Watson DG (1991) Terpenoid phytoalexins. Nat Prod Rep 8: 367–389
Browne LM, Conn KL, Ayer WA, Tewari JP (1991) The camalexins: New phytoalexins produced in the leaves of Camelina sativa ( Cruciferae ). Tetrahedron 47: 3909–3914
Bruce RJ, West CA (1982) Elicitation of casbene synthetase activity in castor bean. The role of pectic fragments of the plant cell wall in elicitation by a fungal endopolygalacturonase. Plant Physiol 69: 1181–1188
Burden RS, Bailey JA (1975) Structure of the phytoalexin from soybean. Phytochemistry 14: 1389–1390
Burden RS, Kemp MS (1983) (-)-7-Hydroxycalamenene, a phytoalexin from Tilia europea. Phytochemistry 22: 1039–1040
Burden RS, Kemp MS (1984) Sesquiterpene phytoalexins from Ulmus glabra. Phytochemistry 23: 383–385
Burden RS, Bailey JA, Dawson GW (1972) Structures of three new isoflavanoids from Phaseolus vulgaris infected with tobacco necrosis virus. Tetrahedron Lett 4175–4178
Burden RS, Bailey JA, Vincent GG (1974) Metabolism of phaseollin by Colletotrichum lindeniuthianum. Phytochemistry 18: 1789–1791
Burden RS, Bailey JA, Vincent GG (1975) Glutinosone, a new antifungal sesquiterpene from Nicotiana glutinosa infected with tobacco mosaic virus. Phytochemistry 14: 221–223
Burden RS, Kemp MS, Wiltshire CW (1984) Isolation and structure determination of cotonefuran, an induced antifungal dibenzofuran from Cotoneaster lactea W. W. Sm. J Chem Soc Perkin Trans 1.1445–1448
Burden RS, Rowell PM, Bailey JA, Loeffler RST, Kemp MS, Brown CA (1985) Debneyol, a fungicidal sesquiterpene from TNV infected Nicotiana debneyi. Phytochemistry 24: 2191–2194
Burden RS, Loeffler RST, Rowell PM, Bailey JA, Kemp MS (1986) Cyclodebneyol, a fungitoxic sesquiterpene from TNV infected Nicotiana debneyi. Phytochemistry 25: 1607–1608
Cartwright DW, Langcake P, Pryce RJ, Leworthy DP, Ride JP (1981) Isolation and characterization of two phytoalexins from rice as momilactones A and B. Phytochemistry 20: 535–537
Chappell J. Nable R (1987) Induction of sesquiterpenoid biosynthesis in tobacco cell suspension cultures by fungal elicitor. Plant Physiol 85: 469–473
Chen Z-Y, Chen Y, Heinstein P, Davisson VJ (1995) Cloning, expression, and characterization of (+)-S-cadinene synthase: a catalyst for cotton phytoalexin biosynthesis. Arch Biochem Biophys 324: 255–266
Cheony.1J, Hahn MG (1991) A specific, high-affinity binding site for the hepta-ß-glucoside elicitor exists in soybean membranes. Plant Cell 3: 137–147.
Cheony J-J, Birberg W, Fügedi P, Pilotti A, Garegg PJ, Hong N, Ogawa T, Hahn MG (1991) Structure-activity relationships of oligo-ß-glucoside elicitors of phytoalexin accumulation in soybean. Plant Cell 3: 127–136
Clemens S, Hinderer W, Wittkampf U, Barz W (1993) Characterization of cytochrome P450-dependent isoflavone hydroxylases from chickpea. Phytochemistry 32: 653–657
Clérivet A, Alami I (1999) Effects of jasmonic acid and of an elicitor from Ceratocystis fimbriata f.sp. platani on the accumulation of phytoalexins in leaves of susceptible and resistant plane trees. Plant Sci 148: 105–110
Coleman M.1, Mainzer J, Dickerson AG (1992) Characterization of a fungal glycoprotein that elicits a defence response in French bean. Physiol Mol Plant Pathol 40: 333–351
Condon P, Kue J (1962) Confirmation of the identity of a fungitoxic compound produced by carrot root tissue. Phytopathology 52: 182–183
Cooksey CJ, Garratt PJ, Dahiya JS, Strange RN (1983) Sucrose: a constitutive elicitor of phytoalexin synthesis. Science 220: 1398–1400
Côté F, Cheong J-J, Alba R, Hahn MG (1995) Characterization of binding proteins that recognize oligoglucoside elicitors of phytoalexin synthesis in soybean. Physiol Plant 93: 401–410
Coxon DT, Price KR, Howard B, Osmon SF, Kalan EB, Zacharius RM (1974) Two new vetispirane derivatives: stress metabolites from potato (Solanum tuberosum) tubers. Tetrahedron Lett 2921–2924
Coxon DT, Price KR, Howard B, Curtis RF (1977) Metabolites from microbially infected potato. Part I. Structure of phytuberin. J Chem Soc Perkin 53–59
Coxon DT, O’Neil TM, Mansfield JW, Porter AEA (1980) Identification of three hydroxyflavan phytoalexins from daffodil bulbs. Phytochemistry 19: 889–891
Crombie L, Mistry J (1990) The phytoalexins of oat leaves: 4H-3,1-benzoxazin-4-ones or amides? Tetrahedron Lett 31: 2647–2648
Cruickshank IAM (1962) Studies on Phytoalexins. IV. The antimicrobial spectrum ofpisatin. Aust J Biol Sci 15: 147–159
Cruickshank IAM, Perrin DR (1968) The isolation and partial characterization of monilicolin A, a polypeptide with phaseollin-inducing activity from Monilinia fructicola. Life Sci 7 (11): 449–458
Dahiya JS, Rimmer SR (1988) Phytoalexin accumulation in tissues of Brassica napus inoculated with Leptosphaeria maculans. Phytochemistry 27: 3105–3107
Daniel M, Purkayastha RP (1995) Handbook of phytoalexin metabolism and action. Macel Dekker, New York, 615 pp
Daniel S, Tiemann K, Wittkampf U, Bless W, Hinderer W, Barz W (1990) Elicitor-induced metabolic changes in cell cultures of chickpea (Cicer arietinum L.) cultivars resistant and susceptible to Ascochyta rabiei. I. Investigations of enzyme activities involved in isoflavone and pterocarpan phytoalexin biosynthesis. Planta 182: 270–278
Darvill AG, Albersheim P (1984) Phytoalexins and their elicitors–A defense against microbial infection in plants. Annu Rev Plant Physiol 35: 243–275
Darvill A, Augur C, Bergmann C, Carlson RW, Cheong J-J, Eberhard S, Hahn MG, Ló V-M, Marfà V, Meyer B, Mohnen D, O’Neill MA, Spiro MD, Van Halbeek H, York WS, Albersheim P (1992) Oligosaccharins–oligosaccharides that regulate growth, development and defence responses in plants. Glycobiology 2: 181–198
Davila-Huerta G, Hamada H, Davis GD, Stipanovic RD, Adams CM, Essenberg M (1995) Cadinane-type sesquiterpenes induced in Gossypium cotyledons by bacterial inoculation. Phytochemistry 39: 531–536
Davis GD, Essenberg M (1995) (+)-ô-Cadinene is a product of sesquiterpene cyclase activity in cotton. Phytochemistry 39: 553–367
Davis KR, Lyon CD, Darvill AG, Albersheim P (1984) Host-parasite interactions. XXV. Endopolygalacturonic acid lyase from Erwinia carotovora elicits phytoalexin accumulation by releasing plant cell wall fragments. Plant Physiol 74: 52–60
Davis KR, Darvill AG, Albersheim P (1986) Host-pathogen interactions. XXX. Characterization of elicitors of phytoalexin accumulation in soybean released from soybean cell walls by endopolygalacturonic acid lyase. Z. Naturforsch. 41c: 39–48.
Denny TP, VanEtten HD (1981) Tolerance by Nectria haematococca MP VI of the chickpea (Cicera arietinum) phytoalexins medicarpin and maackiain. Physiol Plant Pathol 19: 419–437
Dercks W, Creasy LL (1989) The significance of stilbene phytoalexins in the Plasmopara viticolagrapevine interaction. Physiol Mol Plant Pathol 34: 189–202
Desjardins AE, Gardner HW (1989) Genetic analysis in Gibberella pulicaris: Rishitin tolerance, rishitin metabolism, and virulence on potato tubers. Mol Plant-Microbe Interact 2: 26–34
Desjardins AE, Gardner HW (1991) Virulence of Gibberella pulicaris on potato tubers and its relationship to a gene for rishitin metabolism. Phytopathology 81: 429–435
Desjardins AE, VanEtten HD (1986) Partial purification of pisatin demethylase, a cytochrome P-450 from the pathogenic fungus Nectria haematococca. Arch Microbiol 144: 84–90
Desjardins AE, Gardner H W, Plattner RD (1989) Detoxification of the potato phytoalexin lubimin by Gibberella pulicaris. Phytochemistry 28: 431–437
Devys M, Barbier M, Loiselet I, Rouxel T, Sarniguet A, Kollmann A, Bousquet J-F (1988) Brassilexin, a novel sulphur-containing phytoalexin from Brassica juncea L. ( Cruciferae ). Tetrahedron Lett 29: 6447–6448
Devys M, Barbier M, Kollmann A, Rouxel T, Bousquet J-F (1990) Cyclobrassinin sulphoxide, a sulphur-containing phytoalexin from Brassica juncea. Phytochemistry 29: 1087–1088
Dewick PM (I 975) Pterocarpan biosynthesis: chalcone and isoflavone precursors of demethylhomopterocarpin and maackiain in Trifolium pratense. Phytochemistry 14:979–982
Dewick PM (1977) Biosynthesis of pterocarpan phytoalexins in Trifolium pratense. Phytochemistry 16: 93–97
Dewick PM, Martin M (1979) Biosynthesis of pterocarpan and isoflavan phytoalexins in Medicago sativa: the biochemical interconversion of pterocarpans and 2’-hydroxyisoflavans. Phytochemistry 18: 591–596
Dewick PM, Steele MJ (1982) Biosynthesis of the phytoalexin phaseollin in Phaseolus vulgaris. Phytochemistry 21: 1599–1603
De Wit PJGM, Kodde E(1981)lnduction of polyacetylenic phytoalexins in Lycopersicon esculentum after inoculation with Cladosporium fulvum. Physiol Plant Pathol 18: 143–148
De Wit PJGM, Roseboom PHM (1980) Isolation, partial characterization and specificity of glycoprotein elicitors from culture filtrates, mycelium and cell walls of Cladosporium fulvum (syn. Fulvia fulva). Physiol Plant Pathol 16: 391–408
De Wit-Elshove A (1969) The role of pisatin in the resistance of pea plants–some further experiments on the breakdown of pisatin. Neth J Plant Pathol 75: 164–168
Dillon VM, Overton J, Grayer RJ, Harborne JB (1997) Differences in phytoalexin response among rice cultivars of different resistance to blast. Phytochemistry 44: 599–603
Dixon RA, Fuller KW (1977) Characterization of components from culture filtrates of Botrytis cinerea which stimulate phaseollin biosynthesis in Phaseolusvulgaris cell suspension cultures. Physiol Plant Pathol 11: 287–296
Dixon RA, Jennings AC, Davies LA, Gerrish C, Murphy DL (1989) Elicitor-active components from French bean hypocotyls. Physiol Mol Plant Pathol 34: 99–115
Dmitriev AP, Tverskoy LA, Kozlovsky AG, Grodzinsky DM (1990) Phytoalexins from onion and their role in disease resistance. Physiol Mol Plant Pathol 37: 235–244
Dudley MW, Dueber MT, West CA (1986a) Biosynthesis of the macrocyclic diterpene casbene in castor bean (Ricinus communis L.) seedlings. Changes in enzyme levels induced by fungal infection and intracellular localization of the pathway. Plant Physiol 81: 335–342
Dudley MW, Dueber MT, West CA (1986b) Biosynthesis of the macrocyclic diterpene casbene in castor bean (Ricinus communis L.) seedlings. The purification and properties of farnesyl transferase from elicited seedlings. Plant Physiol 81: 343–348
Dumas MT, Strunz GM, Hubbes M, Jeng RS (1983) Isolation and identification of six mansonones from Ulmus americana infected with Ceratocystis ulmi. Experientia 39: 1089–1090
Ebel J (1986) Phytoalexin synthesis: The biochemical analysis of the induction process. Annu Rev Phy to path o l 24: 235–264
Ebel J, Schmidt WE, Loyal R (1984) Phytoalexin synthesis in soybean cells: Elicitor induction of phenylalanine ammonia-lyase and chalcone synthase mRNAs and correlation with phytoalexin accumulation. Arch Biochem Biophys 232: 240–248
Ebel J, Stab MR, Schmidt WE (1985) Induction of enzymes of phytoalexin synthesis in soybean cells by fungal elicitor. In: Neumann K-H, Barz W, Reinhard E (eds) Primary and Secondary Metabolism of Plant Cell Cultures. Springer-Verlag, Berlin, pp 247–254
Echeverri F, Torres F, Quinones W, Cardona G, Archbold R, Roldan J, Brito 1, Luis JG, Lahlou E-H (1997) Danielone, a phytoalexin from papaya fruit. Phytochemistry 44: 255–256
Eldon S, Hillocks RJ (1996)The effect of reduced phytoalexin production on the resistance of upland cotton (Gossypium hirsutum) to Verticillium and Fusarium wilts. Ann Appl Biol 129: 217–225
Elgersma DM, Liem JI (1989) Accumulation of phytoalexins in susceptible and resistant nearisogenic lines of tomato infected with Verticillium albo-atrum and Fusarium oxysporum f. sp. lycopersici. Physiol Mol Plant Pathol 34: 545–555
Elliger CA, Halloin JM (1994) Phenolics induced in Beta vulgaris by Rhizoctonia solani infection. Phytochemistry 37: 691–693
Enkerli J, Bhatt G, Covert SF (1998) Maackiain detoxification contributes to the virulence of Nectria haematococca MP VI on chickpea. Mol Plant-Microbe Interact 11: 317–326
Essenberg M, Pierce ML (1995) Sesquiterpenoid phytoalexins synthesized in cotton leaves and cotyledons during the hypersensitive response to Xanthomonas campestris pv. malvacearum. In: Daniel M, Purkayastha RP (eds) Handbook of phytoalexin metabolism and action. Marcel Dekker, New York, pp 183–198
Facchini PJ, Chappell J (1992) Gene family for an elicitor-induced sesquiterpene cyclase in tobacco. Proc Natl Acad Sci USA 89: 11088–11092
Fagboun DE, Ogundana SK, Adesanya SA, Roberts MF (1987) Dihydrostilbene phytoalexins from Dioscorea rotundata. Phytochemistry 26: 3187–3189
Farmer EE, Helgeson JP (1987) An extracellular protein from Phytophthora parasitica var. nicotianae is associated with stress metabolite accumulation in tobacco callus. Plant Physiol 85: 733–740
Favaron F, Alghisi P, Marciano P, Magro P (1988) Polygalacturonase isozymes and oxalic acid produced by Sclerotinia sclerotiorum in soybean hypocotyls as elicitors of glyceollin. Physiol Mol Plant Pathol 33: 385–395
Fawcett CH, Firn RD, Spence DM (1971) Wyerone increase in leaves of broad bean ( Vicia faba L.) after infection by Botrytis fabae. Physiol Plant Pathol 1: 163–166
Fliegmann J, Schroder G, Schanz S, Britsch L, Schroder J (1992) Molecular analysis of chalcone and dihydropinosylvin synthase from Scots pine (Pinus sylvestris), and differential regulation of these and related enzyme activities in stressed plants. Plant Mol Biol 18: 489–503
Fuchs A, de Vries FW, Platero Sanz M (1980) The mechanism of pisatin degradation by Fusarium oxysporum f. sp. pisi. Physiol Plant Pathol 16: 119–133
Fügedi P, Birberg W, Garegg PJ, Pilotti A (1987) Syntheses of a branched heptasaccharide having phytoalexin-elicitor activity. Carbohydr Res 164: 297–312
Fügedi P, Garegg PJ, Kvarnström I, Svansson L (1988) Synthesis of a heptasaccharide, structurally related to the phytoelicitor active glucan of Phytophthora megasperma f. sp. glycinea. J Carbohydr Chem 7: 389–397
Garcia D, Sanier C, Macheix JJ, D’Auzac.I (1995) Accumulation of scopoletin in Hevea brasiliensis infected by Microcyclus ulei (P. Henn.) V. ARX and evaluation of its fungitoxicity for three leaf pathogens of rubber tree. Physiol Mol Plant Pathol 47: 213–223
Gardner HW, Desjardins AE, McCormick SP, Weisleder D (1994) Detoxification of the potato phytoalexin rishitin by Gibberella pulicaris. Phytochemistry 37: 1001–1005
Gardner HW, Desjardins AE, Weisleder D, Plattner RD (1988) Biotransformation of the potato phytoalexin, lubimin, by Gibberella pulicaris. Identification of major products. Biochim Biophys Acta 966: 347–356
Gehlert R, Schöppner A, Kindl H (1990) Stilbene synthase from seedlings of Pinus sylvestris: purification and induction in response to fungal infection. Mol Plant-Microbe Interact 3: 444–449
Geigert J, Stermitz FR, Johnson G, Maag DD. Johnson DK (1973) Two phytoalexins from sugarbeet (Beta vulgaris) leaves. Tetrahedron 29:2703–2706
Giannini JL, Holt JS, Briskin DP (1988) Isolation of sealed plasma membrane vesicles from Phytophthora megasperma f. sp. glycinea. H. Partial characterization of Ca’ transport and glyceollin effect. Arch Biochem Biophys 266: 644–649
Giannini.1L, Holt JS, Briskin DP (1990) The effect of glyceollin on proton leakage in Phytophthora megasperma f. sp. glycinea plasma membrane and red beet tonoplast vesicles. Plant Sci 68: 39–45
Giannini JL, Halvorson JS, Spessard GO (1991a) High yield isolation and effect on proton leakage of glyceollins I and III. Phytochemistry 30: 3233–3236
Giannini JL, Holt JS, Briskin DP (1991b) The effect of glyceollin on soybean (Glycine max L.) tonoplast and plasma membrane vesicles. Plant Sci 74: 203–211
Giannini JL, Nelson M, Spessard GO (1995) The effect of rishitin on potato tonoplast vesicle and vacuole proton transport. Phytochemistry 40: 1655–1658
Glazebrook J, Ausubel FM (1994) Isolation of phytoalexin-deficient mutants of Arabidopsis thaliana and characterization of their interactions with bacterial pathogens. Proc Natl Acad Sci USA 91: 8955–8959
Glazener JA, Wouters CH (1981)Detection of rishitin in tomato fruits after infection with Botrytis cinerea. Physiol Plant Pathol 19: 243–248
Glocker MO, Su H, Deinzer ML (1993) Structure elucidation of hop plant (Humulus lupulus) phytoalexin elicitors by fast atom bombardment mass spectrometry. J Agri Food Chem 41: 1558–1565
Görge E, Werner D (1991) Degradation of wyerone, the phytoalexin of Faba bean by Rhizobium leguminosarum. Curr Microbiol 23: 153–157
Goy PA, Signer H, Reist R, Aichholz R, Blum W, Schmidt E, Kessmann H (1993) Accumulation of scopoletin is associated with the high disease resistance of the hybrid Nicotiana glutinosa x Nicotiana debneyi. Planta 191: 200–206
Graham TL, Graham MY (1991) Glyceollin elicitors induce major but distinctly different shifts in isoflavonoid metabolism in proximal and distal soybean cell populations. Mol Plant-Microbe Interact 4: 60–68
Graham TL, Kim JE, Graham MY (1990) Role of constitutive isoflavone conjugates in the accumulation of glyceollin in soybean infected with Phytophthora megasperma. Mol Plant-Microbe Interact 3: 157–166
Grayer RJ, Harborne JB (1994) A survey of antifungal compounds from higher plants, 1982–1993. Phytochemistry 37: 19–42
Grayer RJ, Kokubun T (2001) Plant-fungal interactions: the search for phytoalexins and other antifungal compounds from higher plants. Phytochemistry 56: 253–263
Grisebach H, Edelmann L, Fischer D, Kochs G, Welle R (1989) Biosynthesis of phytoalexins and nod-gene inducing isoflavones in soybean. In Lugtenberg BJJ (ed) Signal molecules in plants and plant-microbe interactions. Springer-Verlag, Berlin, pp 57–64
Gross D (1993) Phytoalexins of the Brassicaceae. J Plant Dis Protect 100: 433–442
Gunia W, Hinderer W, Wittkampf U, Barz W (1991) Elicitor induction of cytochrome P-450 monooxygenases in cell suspension cultures of chickpea (Citer arietinum L.) and their involvement in pterocarpan phytoalexin biosynthesis. Z Naturforsch 46c: 58–66
Guo L, Paiva NL (1995) Molecular cloning and expression of alfalfa (Medicago sativa L.) vestitone reductase, the penultimate enzyme in medicarpin biosynthesis. Arch Biochem Biophys 320: 353–360
Guo L, Dixon RA, Paiva NL (1994) Conversion of vestitone to medicarpin in alfalfa (Medicago sativa) is catalyzed by two independent enzymes. J Biol Chem 269: 22372–22378
Gustine DL (1987) Induction of medicarpin biosynthesis in Ladino clover callus by p-chloromercuribenzoic acid is reversed by dithiothreitol. Plant Physiol 84: 3–6
Gutierrez M-C, Parry A, Tena M, Jorrin J, Edwards R (1995) Abiotic elicitation of coumarin phytoalexins in sunflower. Phytochemistry 38: 1185–1191
Hadwiger LA, Ogawa T, Kuyama H (1994) Chitosan polymer sizes effective in inducing phytoalexin accumulation and fungal suppression are verified with synthesized oligomers. Mol Plant-Microbe Interact 7: 531–533
Hagmann M-L, Heller W, Grisebach H (1984) Induction of phytoalexin synthesis in soybean. Stereospecific 3,9-dihydroxypterocarpan 6a-hydroxylase from elicitor-induced soybean cell cultures. Eur J Biochem 142: 127–131
Hahn MG, Bonhoff A, Grisebach H (1985) Quantitative localization of the phytoalexin glyceollin I in relation to fungal hyphae in soybean roots infected with Phytophthora megasperma f. sp. glycinea. Plant Physiol 77: 591–601
Hahn MG, Bucheli P, Cervone F, Doares SH, O’Neil RA, Darvill A, Albersheim P (1989) The roles of cell wall constituents in plant-pathogen interactions. In: Kosuge T, Nester EW (eds) Plant-Microbe Interactions. Molecular and Genetic Perspectives, vol 3. McGraw Hill Publ, New York, pp 131–181
Hain R, Bieseler B, Kindl H, Schröder G, Stöcker R (1990) Expression of a stilbene synthase gene in Nicotiana tabacum results in synthesis of the phytoalexin resveratrol. Plant Miol Biol 15: 325–335
Hain R, Reif H-J, Krause E, Langebartels R, Kindl H, Vornam B, Wiese W, Schmelzer E, Schreier PH, Stöcker RH, Stenzel K (1993) Disease resistance results from foreign phyto-alexin expression in a novel plant. Nature 361: 153–156
Ham K-S, Kauffmann S, Albersheim P, Darvill AG (1991) Host-pathogen interactions XXXIX. A soybean pathogenesis-related protein with ß-1,3-glucanase activity releases phytoalexin elicitor-active heat-stable fragments from fungal walls. Mol Plant-Micbrobe Interact 4: 545–552
Hamdan MAMS, Dixon RA (1987a) Fractionation and properties of elicitors of the phenylpropanoid pathway from culture filtrates of Colletotrichum lindemuthianum. Physiol Mol Plant Pathol 31: 91–103
Hamdan MAMS, Dixon RA (1987b) Differential patterns of protein synthesis in bean cells exposed to elicitor fractions from Colletotrichum lindemuthianum. Physiol Mol Plant Pathol 31: 105–121
Hamerski D, Beier RC, Kneusel RE, Matern U, Himmelspach K (1990) Accumulation of coumarins in elicitor-treated cell suspension cultures of Animi majus. Phytochemistry 29: 1137–1142
Hammerschmidt R (1999) Phytoalexins: What have we learned after 60 years? Annu Rev Phytopathol 37: 285–306
Hammerschmidt R, Kue J (1979) Isolation and identification of phytuberin from Nicotiana tabacum previously infiltrated with an incompatible bacterium. Phytochemistry 18: 874–875
Hanawa F, Kanauchi M, Tahara S, Mizutani J (1994) Lettucenin A as a phytoalexin of dandelion and its elicitation in dandelion cell cultures. J Fac Agri Hokkaido Univ 66: 151–162
Harborne JB (1990) Role of secondary metabolites in chemical defence mechanisms in plants.Pages 126–139 in Bioactive Compounds from Plants. Ciba foundation Symposium 154
Harborne JB (1999) The comparative biochemistry of phytoalexin induction in plants. Biochem Syst Ecol 27: 335–367
Hardegger E, Schellenbaum M, Corrodi H (1963) Welkstoffe and Antibiotika. Uber induzierte Abwehrstoffe bei Orchideen II. HeIv Chim Acta 46: 1171–1180
Harding VK, Heale JB (1980) Isolation and identification of the antifungal compounds accumulating in the induced resistance response of carrot slices to Botrytis cinerea. Physiol Plant Pathol 17: 277–289
Hargreaves JA, Mansfiled JW, Coxon DT (1976a) Identification of medicarpin as a phytoalexin in the broad bean plant (Vicia faba L.). Nature 262: 318–319
Hargreaves JA, Mansfiled JW, Coxon DT, Price KR (1976b) Wyerone epoxide as a phytoalexin in Vicia faba and its metabolism by Botrytis cinerea and B. fabae in vitro. Phytochemistry 15: 1119–1121
Hartmann G, Nienhaus F (1974) The isolation of xanthoxylin from the bark of Phytophthora-and Hendersonula-infected Citrus Limon and its fungitoxic effect. Phytopathol Z 81: 97–113
Heinstein P (1985) Stimulation of sesquiterpene aldehyde formation in Gossypium arboreum cell suspension cultures by conidia of Verticillium dahliae. J Nat Prod 48: 907–915
Henfling JWDM, Bostock R, Kuc J (1980) Effect of abscisic acid on rishitin and lubimin accumulation and resistance to Phytophthora infestans and Cladosporium cucumerinum in potato tuber slices. Phytopathology 70: 1074–1078
Higgins VJ, Stoessl A, Heath MC (1974) Conversion of phaseollin to phaseollinisoflavan by Stemphylium botryosum. Phytopathology 64: 105–107
Hildenbrand S, Ninnemann H (1994) Kinetics of phytoalexin accumulation in potato tubers of different genotypes infected with Erwinia carotovora ssp. atroseptica. Physiol Mol Plant Pathol 44: 335–347
Hipskind JD, Hanau R, Leite B, Nicholson RL (1990) Phytoalexin accumulation in sorghum: identification of an apigeninidin acyl ester. Physiol Mol Plant Pathol 36: 381–396
Höhl B, Barz W (1987) Partial characterization of an enzyme from the fungus Ascochyta rabiei for the reductive cleavage of pterocarpan phytoalexins to 2’-hydroxysioflavans. Z Naturforsch 42c: 897–901
Hoppe HH, Hümme B, Heitefuss R (1980) Elicitor induced accumulation of phytoalexins in healthy and rust infected leaves of Phaseolus vulgaris. Phytopathol Z 97: 85–88
Hoshino T, Chida M, Yamaura T, Yoshizawa Y, Mizutani J (1994) Phytoalexin induction in green pepper cell cultures treated with arachidonic acid. Phytochemistry 36: 1417–1419
Hoshino T, Yamaura T, Imaishi H, Chida M, Yoshizawa Y, Higashi K, Ohkawa H, Mizutani J (1995) 5-epi-Aristolochene 3-hydroxylase from green pepper. Phytochemistry 38: 609–613
Hrazdina G, Borejsza-Wysocki W, Lester C (1997) Phytoalexin production in an apple cultivar resistant to Venturia inaequalis. Phytopathology 87: 869–876
Huang J-S, Barker KR (1991) Glyceollin 1 in soybean-cyst nematode interactions. Spatial and temporal distribution in roots of resistant and susceptible soybeans. Plant Physiol 96: 1302–1307
Ingham JL (1976a) Induced isoflavonoids from fungus-infected stems of pigeon pea (Cajamus cajan). Z Naturforsch. 31c: 504–508
Ingham JL (1976b) Induced and constitutive isotavonoids from stems of chickpeas (Cicer arietinum L.) inoculated with spores of Helminthosporium carbonum Ullstrup. Phytopathol Z 87: 353–367
Ingham JL (1979) Isoflavonoid phytoalexins of the genus Medicago. Biochem Syst Evol 7: 29–34
Ingham JL (1982) Phytoalexins from the leguminosae. In: Bailey JA, Mansfield JW (eds) Phytoalexins. John Wiley and Sons, New York, pp 21–80
Ingham JL (1990) A further investigation of phytoalexin formation in the genus Trifolium. Z Naturforsch 45c: 829–834
Ingham JL, Dewick PM (1979) A new isoflavan phytoalexin from leaflets of Lotus hispidus. Phytochemistry 18: 1711–1714
Ingham JL, Miller RL (1973) Sativin: an induced isoflavan from the leaves of Medicago sativa L. Nature 242: 125–126
Ingham JL, Keen NT, Mulheirn L.1, Lyne RL (1981) Inducibly-formed isoflavonoids from leaves of soybean (Glycine max). Phytochemistry 20: 795–798
Inoue H, Oha K, Ando M, Uritani 1 (1984) Enzymatic reduction of dehydro-ipomeamarone to ipomeamarone in sweet potato root tissue infected by Ceratocystis fimbriata. Physiol Plant Pathol 25: 1–8
Ishihara A, Ohtsu Y, Iwamura H (1999) Biosynthesis of oat avenanthramide phytoalexins. Phytochemistry 50: 237–242
Jadhav SJ, Mazza G, Salunkhe DK (1991) Terpenoid phytoalexins in potatoes: A review. Food Chem 41: 195–217
Jin DF, West CA (1984) Characteristics of galacturonic acid oligomers as elicitors of casbene synthetase activity in castor bean seedlings. Plant Physiol 74: 989–992
Johnson C, Brannon DR, Kuc J (1973) Xanthotoxin: a phytoalexin of Pastinaca saliva root. Phytochemistry 12: 2961–2962
Johnson G, Maag DD, Johnson DK, Thomas RD (1976) The possible role of phytoalexins in the resistance of sugarbeet (Beta vulgaris) to Cercospora beticola. Physiol Plant Pathol 8: 225–230
Kaplan DT, Keen NT, Thomason B (1980) Association of glyceollin with the incompatible response of soybean roots to Meloidogyne incognita. Physiol Plant Pathol 16: 309–318
Kato H, Kodama O, Akatsuka T (1993) Oryzalexin E, a diterpene phytoalexin from UV-irradiated rice leaves. Phytochemistry 36: 299–301
Kato H, Kodama O, Akatsuka T (1994) Oryzalexin F, a diterpene phytoalexin from UV-irradiated rice leaves. Phytochemistry 36: 299–301
Kato H, Kodama O, Akatsuka T (1995) Characterization of an inducible P450 hydroxylase involved in the rice diterpene phytoalexin biosynthesis pathway. Arch Biochem Biophys 316: 707–712
Kato N, Imaseki H, Nakashima N, Uritani 1 (1971) Structure of a new sesquiterpenoid, ipomeamaronol, in diseased sweet potato root tissue. Tetrahed Lett 843–846
Katsui N, Murai A, Takasugi M, Imaizumi K, Masamune T (1968) The structure of rishitin, a new antifungal compound from diseased potato tubers. J Chem Soc Chem Commun 43–44
Katsui N, Matsunaga A, Imaizumi K, Masamune T, Tomiyama K (1971) The structure and synthesis of rishitinol, a new sesquiterpene alcohol from diseased potato tubers. Tetrahed Lett 83–86
Katsui N, Matsunaga A, Masamune T (1974) The structure of lubimin and oxylubimin, antifungal metabolites from diseased potato tubers. Tetrahed Lett 4483–4486
Keen NT (1972) Accumulation of wyerone in broad bean and demethylhomopterocarpin in jack bean after inoculation with Phytophthora megasperma var. sojae. Phytopathology 62: 1365–1366
Keen NT (1975a) Specific elicitors of plant phytoalexin production: determinants of race specificity in pathogens? Science 187: 74–75
Keen NT (1975b) The isolation of phytoalexins from germinating seeds of Cicer arietinum, Vigna sinensis, Arachis hypogaea, and other plants. Phytopathology 65: 91–92
Keen NT, Kennedy BW (1974) Hydroxyphaseollin and related isoflavonoids in the hyper-sensitive resistance reaction of soybeans to Pseudomonas glycinea. Physiol Plant Pathol 4: 173–185
Keen NT, Zaki Al, Sims JJ (1972) Biosynthesis of hydroxyphaseollin and related isoflavanoids in disease-resistant soybean hypocotyls. Phytochemistry 11: 1031–1039
Keen NT, Yoshikawa M, Wang MC (1983) Phytoalexin elicitor activity of carbohydrates from Phytophthora megasperma f. sp. glycinea and other sources. Plant Physiol 71: 466–471
Kemp MS, Burden RS (1984) Isolation and structure determination of y-pyrufura, a thrid induced antifungal dibenzofuran from the wood of Pyrus communis L. infected with Chondrostereum purpureum (Pers. ex Fr.) Pouzar. J Chem Soc Perkin Trans 1: 1441–1443
Kemp MS, Burden RS, Loeffler RST (1983) Isolation, structure determination, and total synthesis of the dibenzofurans a-and 13-pyrufuran, new phytoalexins from the wood of Pyrus communis L. J Chem Soc Perkin Trans I: 2267–2272
Kendra DF, Hadwiger, LA (1984) Characterization of the smallest chitosan oligomer that is maximally antifungal to Fusarium solani and elicits pisatin formation in Pisum sativum. Exp Mycol 8: 276–281
Kessmann H, Edwards R, Geno PW, Dixon, RA (1990) Stress responses in alfalfa (Medicago sativa L.). V. Constitutive and elicitor-induced accumulation of isoflavonoid conjugates in cell suspension cultures. Plant Physiol 94: 227–232
Kistler HC, VanEtten HD (1981) Phaseollin metabolism and tolerance in Fusarium solani f. sp. phaseoli. Physiol Plant Pathol 19: 257–271
Kobayashi A, Akiyama K, Kawazu K (1994) Partially N-deacetylated chitin fragments are strong elicitors for (+)-pisatin induction in epicotyls of pea. Z Naturforsch 49c: 302–308
Kochs G, Grisebach, H (1989) Phytoalexin synthesis in soybean: Purification and reconstitution of cytochrome P450 3,9-dihydroxypterocarpan 6a-hydroxylase and separation from cytochrome P450 cinnamate 4-hydroxylase. Arch Biochem Biophs 273: 543–553
Kochs G, Werck-Reichhard D, Grisebach H (1992) Further characterization of cytochrome P450 involved in phytoalexin synthesis in soybean: cytochrome P450 cinnamate 4-hydroxylase and 3,9-dihydroxypterocarpan 6a-hydroxylase. Arch Biochem Biophys 293: 187–194
Kodama O. Li WX, Tamogami S, Akatsuka T (1992a) Oryzalexin S, a novel stemarane-type diterpene rice phytoalexin. Biosci Biotehnol Biochem 56: 1002–1003
Kodama O, M iyakawa.1, Akatsuka T, Kiyosawa S (1992b) Sakuranetin, a flavanone phytoalexin from ultraviolet-irradiated rice leaves. Phytochemistry 31: 3807–3809
KogaJ, Shimura M, Oshima K, Ogawa N, Yamauchi T, Ogasawara N (1995) Phytocassanes A, B, C, and D, novel diterpen phytoaleixns from rice, Oryza sativa L. Tetrahedron 51: 7907–7918
Koga J, Ogawa N, Yamauchi T, Kikuchi M, Ogasawara N, Shimura M (1997) Functional moiety for the antifungal activity of phytocassane E, a diterpene phytoalexin from rice. Phytochemistry 44: 249–253
Koga J, Yamauchi T, Shimura M, Ogawa N, Oshima K, Umemura K, Kikuchi M, Ogasawara N (1998) Cerebrosides A and C, sphingolipid elicitors of hypersensitive cell death and phytoalexin accumulation in rice plants. J. Biol. Chem. 273: 31985–31991
Kokubun T, Harbome JB (1995) Phytoalexin induction in the sapwood of plants of the Maloideae (Rosaceae): biphenyls or dibenzofurans. Phytochemistry 40: 1649–1654
Kokubun T, Harborne JB, Eagles J (1994) 2’,6’-Dihydroxy-4’-methoxyacetophenone, a phytoalexin from the roots of Sanguisorba minor. Phytochemsitry 35: 331–333
Kokubun T, Harborne JB, Eagles J, Waterman PG (1995a) Dibenzofuran phytoalexins from the sapwood of Cotoneaster acutifolius and five related species. Phytochemistry 38: 57–60
Kokubun T, Harborne JB, Eagles J, Waterman PG (1995b) Dibenzofuran phytoalexins from the sapwood tissue ofPhotinia, Pyracantha and Crataegus species. Phytochemistry 39: 1033–1037
Komae K, Komae A, Misaki A (1990) A 4,5-unsaturated low molecular oligo-galacturonide as a potent phytoalexin-elicitor isolated from polygalacturonide of Ficus awkeotsang. Agri Biol Chem 54: 1477–1484
Kombrink E, Hahlbrock K (1986) Responses of cultured parsley cells to elicitors from phytopathogenic fungi. Timing and dose dependency of elicitor-induced reactions. Plant Physiol 81: 216–221
Kubota T, Matsuura T (1953) Chemical studies on the black rot disease of sweet potato. V. Chemical constitution of ipomeamarone. J Chem Soc Japan 74: 248–251
Kuc J (1982) Phytoalexins from the Solanaceae. In Bailey JA, Mansfiled JW (eds) Phytoalexins. John Wiley and Sons, New York, pp 81–105
Kuc J (1995) Phytoalexins, stress metabolism, and disease resistance in plants. Annu Rev Phytopathol 33: 275–297
Kupidlowska E, Dobrzynska K, Parys E, Zobel AM (1994) Effect of coumarin and xanthotoxin on mitochondria] structure, oxygen uptake, and succinate dehydrogenase activity in onion root cells. J Chem Ecol 20: 2471–2480
Kurosaki F (1994) Regulation of biosynthesis of carrot phytoalexin 6-methoxymellein. Phytochemistry 37: 727–730
Kurosaki F, Nishi A (1991) Comparison of enzyme activities involved in the biosynthesis of carrot phytoalexin 6-methoxymellein. Phytochemistry 30: 1823–1825
Kurosaki F, Kizawa Y, Nishi A (1989) Derailment product in NADPH-dependent synthesis of a dihydroisocoumarin 6-hydroxymellein by elicitor-treated carrot cell extracts. Eur J Biochem 185: 85–89
Lackner M (1990) Secondary metabolism in microorgnisms, plants, and animals. Springer-Verlag, Berlin
Langcake P, Pryce RJ (1977) A new class of phytoalexins from grapevines. Experientia 33: 151–152
Lange BM, Trost M, Heller W, Langebartels C, Sandermann H.Jr (1994) Elicitor-induced formation of free and cell-wall-bound stilbenes in cell-suspension cultures of Scots pine (Pinus sylvestris L.). Planta 194: 143–148
Latunde-Dada AO, Dixon RA, Lucas JA (1987) Induction of phytoalexin biosynthetic enzymes in resistant and susceptible lucerne callus lines infected with Verticillium albo-atrum. Physiol Mol Plant Pathol 31: 15–23
Lee S-C, West CA (1981) Polygalacturonase from Rhizopus stolonifer is an elicitor of casbene synthase activity in Castor bean (Rhicinus communis L.) seedlings. Plant Physiol 67: 633–639
Li D, Chung K-R, Smith DA, Schardl CL (1995) The Fusarium solani gene encoding kievitone hydratase, a secreted enzyme that catalyzes detoxification of a bean phytoalexin. Mol Plant-Microbe Interact 8: 388–397
Liswidowati, Melchior F, Hohmann F, Schwer B, Kindl H (1991) Induction of stilbene synthase by Botrytis cinerea in cultured grapevine cells. Planta 183: 307–314
Longland AC, Slusarenko AJ, Friend J (1987) Arachidonic and linoleic acids elicit isoflavonoid phytoalexin accumulatiuon in Phaseolus vulgaris ( French bean ). J Phytopathol 120: 289–297
Lucy MC, Matthews PS, VanEtten HD (1988) Metabolic detoxification of the phytoalexins maackiain and medicarpin in Nectria haematococca field isolates: relationship to virulence on chickpea. Physiol Mol Plant Pathol 33: 187–199
Luis JG, Echeverri F, Quinones W, Brito I, López M, Torres F, Cardona G, Aguiar Z, Pelaez C, Rojas M (1993) lrenolone and emenolone: two new types of phytoalexin from Musa paradisiaca. J Org Chem 58: 4306–4308
Luis JG, Quinones W, Echeverri F, Grillo TA, Kishi MP, Garcia-Garcia F, Torres F, Cardona G (1996) Musanolones: four 9-phenylphenalenones from rhizomes of Musa acuminala. Phytochemistry 41: 753–757
Lyne RL, Mulheirn L.I, Leworthy DP (1976) New pterocarpinoid phytoalexins of soybean. J Chem Soc Chem commun 497–498
Lyon FM, Wood RKS (1975) Production of phaseollin, coumestrol and related compounds in bean leaves inoculated with Pseudomonas spp. Physiol Plant Pathol 6: 117–124
Lyon GD (1980) Evidence that the toxic effect of rishitin may be due to membrane damage. J Expt Bot 31: 957–966
Mace ME, Stipanovic RD (1995) Mode of action of the phytoalexin desoxyhemigossypol against the wilt pathogen, Verticillium dahliae. Pesticide Biochem Physiol 53: 205–209
Mackenbrock U, Barz W (1991) Elicitor-induced formation of pterocarpan phytoalexins in chickpea Cicer arietinum L.) cell suspension cultures from constitutive isoflavone conjugates upon inhibition of phenylalanine ammonia lyase. Z Naturforsch 46c: 43–50
Mackenbrock U, Gunia W, Barz W (1993) Accumulation and metabolism of medicarpin and maackiain malonylglucosides in elicited chickpea (Cicer arietinum L.) cell suspension cultures. J Plant Physiol 142: 385–391
Madar Z, Solel Z, Riov J, Sztejnberg A (1995a) Phytoalexin production by cypress in response to infection by Diplodia pinea f sp. cupressi and its relation to water stress. Physiol Mol Plant Pathol 47: 29–38
Madar Z,Gottlieb HE, Cojocaru M, Riov J, Sold Z, Sztejnberg A (1995b) Antifungal terpenoids produced by cypress after infection by Diplodia pinea f. sp. cupressi. Phytochemistry 38:351–354
Maloney AP, VanEtten HD (1994) A gene from the fungal plant pathogen Nectria haematococca that encodes the phytoalexin-detoxifying enzyme pisatin demethylase defines a new cytochrome P450 family. Mol Gen Genet 243: 506–514
Mansfield JW. Porter AEA, Smallman RV (1980) Dihydrowyerone derivatives as components of the furanoacetylenic phytoalexin response of tissues of Vicia faba. Phytochemistry 19: 1057–1061
Marinelli F, Gregoria SD, Ronchi VN (1991) Phytoalexin production and cell death in elicited carrot cell suspension cultures. Plant Sci 77: 261–266
Marinelli F, Ronchi VN, Salvador P (1994) Elicitor induction of enzyme activities and 6-methoxymellein production in carrot cell suspension culture. Phytochemistry 35: 1457–1460
Marshall PS, Harborne JB, King GS (1987) A spiroketalenol ether phytoalexin from infected leaves and stems of Coleostephus myconis. Phytochemistry 26: 2493–2494
Mau CJD, West CA (1994) Cloning of casbene synthase cDNA: Evidence for conserved structural features among terpenoid cyclases in plants. Proc Natl Acad Sci USA 91: 8497–8501
Mayama S, Tani T, Ueno T, Hirabayashi K, Nakashima T, Fukami H, Mizuno Y, Inci H (1981) Isolation and structure elucidation of genuine oat phytoalexin, avenalumin I. Tetrahedron Lett 22: 2103–2106
Melchior F, Kind H (1991) Coordinate-and elicitor-dependent expression of stilbene synthase and phenylalanine ammmonia-lyase genes in Vitis cv. Optima. Arch Biochem Biophys 288: 552–557
Miao VPW, VanEtten HD (1992a) Three genes for metabolism of the phytoalexin maackiain in the plant pathogen Nectria haematococca: meiotic instability and relationship to a new gene for pisatin demethylase. Appl Environ Microbiol 58: 801–808
Miao VPW, VanEtten HD (1992b) Genetic analysis of the role of phytoalexin detoxification in virulence of the fungus Nectria haematococca on chickpea (Cicer arietinum). Appl Environ Microbiol 58: 809–814
Mieth H, Speth V, Ebel J (1986) Phytoalexin production by isolated soybean protoplasts. Z Naturforsch 41c: 193–201
Milat M-L, Ricci P, Bonnet P, Blein J-P (1991) Capsidiol and ethylene production by tobacco cells in response to cryptogein, an elicitor from Phytophthora cryptogea. Phytochemistry 30: 2171–2173
Miyagawa H, Ishihara A, Kuwahara Y, Ueno T, Mayama S (1996) A stress compound in oats induced by victorin, a host-specific toxin from Helminthosporium victoriae. Phytochemistry 41: 1473–1475
Miyakodo M. Watanabe K, Ohno N, Nonaka F, Morita A (1985) Isolation and structure determination of eriobofuran, a new dibenzofuran phytoalexin from leaves of loquat, Eriobotrya japonica L. J Pesticide Sci 10: 101–106
Modafar CE, Clerivet A, Fleuriet A, Macheix JJ (1993) Inoculation of Platanus acerifolia with Ceratocystis fimbriata f. sp. platani induces scopoletin and umbelliferone accumulation. Phytochemistry 34: 1271–1276
Moesta P, Grisebach H (1982) L-2-Aminooxy-3-phenylpropionic acid inhibits phytoalexin accumulation in soybean with concomitant loss of resistance against Phytophthora mega-sperma f. sp. glycinea. Physiol Plant Pathol 21: 65–70
Moesta P, West CA (1985) Casbene synthetase: Regulation of phytoalexin biosynthesis in Ricinus communis L. seedlings. Arch Biochem Biophys 238: 325–333
Monde K, Katsui N, Shirata A, Takasugi M (1990a) Brassicanals A and B, novel sulphur-containing phytoalexins from th cabbage Brassica campestris L. ssp. pekinensis. Chem Lett 209–210
Monde K, Oya T, Shirata A, Takasugi M (1990b) A guaianolide phytoalexin, cichoralexin, from Cichorium intybus. Phytochemistry 29: 3449–3451
Monde K, Sasaki K, Shirata A, Takasugi M (1990e) 4-Methoxybrassinin, a sulphur-containing phytoalexin from Brassica oleracea. Phytochemistry 29: 1499–1500
Monde K, Sasaki K, Shirata A, Takasugi M (1991) Brassicanal C and two dioxindoles from cabbage. Phytochemistry 30: 2915–2917
Monde K, Kishimoto M, Takasugi M (1992) Yurinelide, a novel 3-benzylidene-1,4-bezodioxin2(3H)-one phytoalexin from Lillian maximowiczii. Tetrahedron Lett 33: 5395–5398
Monde K, Takasugi M, Ohnishi T (1994a) Biosynthesis of cruciferous phytoalexins. J Am Chem Soc 116: 6650–6657
Monde K, Tamura K, Takasugi M, Kobayashi K, Somei M (1994b) Dehydro-4-methoxycyclobrassinin, a sulfur-containing phytoalexin isolated from turnip Brassica campestris ssp. rapa. Heterocycles 38: 263–267
Monde K, Takasugi M, Shirata A (1995) Three sulphur-containing stress metabolites from Japanese radish. Phytochemistry 39: 581–586
Monden T, Toida T, Nakamura H, Sato N, Murai A (1995) Isolation of an endogenous elicitor induced by hydrogen peroxide from potato. Chem Lett 173–174
Müller KO, Börger H (1940) Experimentel le Untersuchungen über die Phytophthora-resistenz der Kartoffel. Arb Biol Anst Reichsanst (Berlin) 23: 189–231
Murai A, Sato K, Hasegawa T (1995) Implicit role of hydrogen peroxide on phytoalexin production in higher plants. Chem Lett 883–884
Mwangi LM, Lin D, Rubbers M (1990) Chemical factor in Pinus strobus inhibitory to Armillaria ostoyae. Eur J For Pathol 20: 8–14
Nicholson RL, Kollipara SS, Vincent JR, Lyons PC, Cadena-Gomez G (1987) Phytoalexin synthesis by the sorghum mesocotyl in response to infection by pathogenic and non-pathogenic fungi. Proc Natl Acad Sci USA 84: 5520–5524
Niemann GJ (1993) The anthranilamide phytoalexins of the Caryophyllaceae and related compounds. Phytochemistry 34: 319–328
Niemann GJ, Liem J, van der Kerk-van Hoof A, Niessen WMA (1992) Phytoalexins, benzoxazinones, N-aroylanthranilates and N-aroylanilines, from Fusariunrinfected carnation stems. Phytochemistry 31: 3761–3767
Nothnagel EA, McNeil M, Albersheim P, Dell A (1983) Host-pathogen interactions. XXII. A galacturonic acid oligosaccharide from plant cell walls elicits phytoalexins. Plant Physiol 71: 916–926
Ôba K, Oga K, Uritani I (1982) Metabolism of ipomeamarone in sweet potato root slices before and after treatment with mercuric chloride or infection with Ceratocystis fambriata. Phytochemistry 21: 1921–1925
Oguni IU, Uritani I (1974) Dehydroipomeamarone from infected 1pomoea batatas root tissue. Phytochemistry 13: 521–522
PaivaNL, Edwards R, Sun Y, Hrazdina G, Dixon RA (1991) Stress responses in alfalfa (Medicago sativa L.) 11. Molecular cloning and expression of alfalfa isoflavone reductase, a key enzyme of isoflavonoid phytoalexin biosynthesis. Plant Mol Biol 17: 653–667
Parker JE, Schulte W, Hahlbrock K, Scheel D (1991) An extracellular glycoprotein from Phytophthora megasperma f. sp. glycinea elicits phytoalexin synthesis in cultured parsley cells and protoplasts. Mol Plant-Microbe Interact 4: 19–27
Parniske M, Ahlborn B, Werner D (1991) Isoflavonoid-inducible resistance to the phytoalexin glyceollin in soybean rhizobia. J Bacteriol 173: 3432–3439
Paxton JD (1981) Phytoalexins–A new working redefinition. Phytopathol Z 101: 106–109
Pedras MSC, Khan AQ (1996) Biotransformation of the Brassica phytoalexin brassicanal A by the blackleg fungus. J Agri Food Chem 44: 3403–3407
Pedras MSC, Khan AQ (1997)Unprecedented detoxification of the cruciferous phytoalexin camalexin by a root phytopathogen. Bioorg Med Chem Lett 7: 2255–2260
Pedras MSC, Khan AQ (2000) Biotransformation of the phytoalexin camalexin by the phytopathogen Rhizoctonia solani. Phytochemistry 53: 59–69
Pedras MSC, Smith KC (1997) Sinalexin, a phytoalexin from white mustard elicited by destruxin B and Alternaria brassicae. Phytochemistry 46: 833–837
Pedras MSC, Taylor JL (1993) Metabolism of the phytoalexin brassinin by the “blackleg” fungus. J Nat Prod 56: 731–738
Pedras MSC, Zaharia IL (2000) Sinalbins A and B, phytoalexins from Sinapis alba: elicitation, isolation, and synthesis. Phytochemistry 55: 213–216
Pedras MSC, Sorensen JL, Okanga FI, Zaharia IL (1999) Wasalexins A and B, new phytoalexins from wasabi: isolation, synthesis, and antifungal activity. Bioorg Med Chem Lett 9: 3015–3020
Pedras MSC, Okanga FI, Zaharia IL, Khan AQ (2000) Phytoalexins from crucifers: synthesis, biosynthesis, and biotransformation. Phytochemistry 53: 161–176
Perrin DR (1964) The structure of phaseolin. Tetrahedron Lett 29–35
Perrin DR, Bottomley W (1962) Studies on phytoalexins. V. The structure of pisatin from Pisum sativum L. J Amer Chem Soc 84: 1919–1922
Perrin DR, Whittle CP, Batterham TJ (1972) The structure of phaseollidin. Tetrahedron Lett 1673–1676
Pezet R (1998) Purification and characterization of a 32-kDa laccase-like stilbene oxidase produced by Botrytis cinerea Pers.:Fr. FEMS-Microbiol Lett 167: 203–208
Pezet R, Pont V, Hoang-Van K (1991) Evidence for oxidative detoxication of pterostilbene and resveratrol by a laccase-like stilbene oxidase produced by Botrytis cinerea. Physiol Mol Plant Pathol 39: 441–450
Platero Sanz M, Fuchs A (1978) Degradation of pisatin, an antimicrobial compound produced by Pisun2 sativum L. Phytopathol Medit 17: 14–17
Preisig CL, Kuc JA (1985) Arachidonic acid-related elicitors of the hypersensitive response in potato and enhancement of their activities by glucans from Phytophthora infestans ( Mont.) de Bary. Arch Biochem Biophys 236: 379–389
Preisig CL, Matthews DE, VanEtten HD (1989) Purification and characterization ofS-adenosyl-Lmethionine:6a-hydroxymaackiain 3-O-methyltransferase from Pisum sativum. Plant Physiol 91: 559–566
Preisig CL, Bell JN, Sun Y, Hrazdina G, Matthews DE, VanEtten HD (1990) Biosynthesis of the phytoalexin pisatin. Isoflavone reduction and further metabolism of the product sophorol by extracts of Pisum sativum. Plant Physiol 94: 1444–1448
Preisig CL, VanEtten HD, Moreau RA (1991) Induction of 6a-hydroxymaackiain 3–0-methyltransferase and phenylalanine ammonia-Iyase mRNA translational activities during the biosynthesis of pisatin. Arch Biochem Biophys 290: 468–473
Proctor RH, Guries RP, Smalley EB (1994) Lack of association between tolerance to the elm phytoalexin mansonone E and virulence in Ophiostoma novo-ulmi. Can J Bot 72: 1355–1364
Pueppke SG, VanEtten HD (1974) Pisatin accumulation and lesion development in peas infected with Aphanomyces euteiches, Fusarium solani f. sp. pisi, or Rhizoctonia solani. Phytopathology 64: 1433–1440
Pueppke SG, VanEtten HD (1975) Identification of three new pterocarpans from Pisum sativum infected with Fusarium solani f. sp. pisi. J Chem Soc Perkin Trans 1: 946–948
Rakwal R, Agrawal GK, Yonekura M, Kodama 0 (2000) Naringenin 7–0-methyltransferase involved in the biosynthesis of the flavanone phytoalexin sakuranetin from rice (Oryza sativa L.). Plant Sci 155: 213–221
Ralton JE, Howlett BJ, Clarke AE (1988) Interaction of cowpea with Phytophthora vignae: inheritance of resistance and production of phenylalanine ammonia-Iyase as a resistance response. Physiol Mol Plant Pathol 32: 89–103
Reimmann C, VanEtten HD (1994) Cloning and characterization of the PDA6–1 gene encoding a fungal cytochrome P-450 which detoxifies the phytoalexin pisatin from garden pea. Gene 146: 221–226
Reinecke T, Kindl H (1994a) Inducible enzymes of the 9,10-dihydro-phenanthrene pathway. Sterile orchid plants responding to fungal infection. Mol Plant-Microbe Interact 7: 449–454
Reinecke T, Kindl H (1994b) Characterization of bibenzyl synthase catalysing the biosynthesis of phytoalexins of orchids. Phytochemistry 35: 63–66
Ren Y-Y, West CA (1992) Elicitation of diterpene biosynthesis in rice (Oryza sativa L.) by chitin. Plant Physiol 99: 1169–1178
Rhodes MJC (1994) Physiological roles for secondary metabolites in plants: some progress, many outstanding problems. Plant Mol Biol 24: 1–20
Rich JR, Keen NT, Thomason IJ (1977) Association of coumestans with the hypersensitivity of lima bean roots to Pratylenchus scribneri. Physiol Plant Pathol 10: 105–116
Robeson DJ, Ingham JL (1979) New pterocarpan phytoalexins from Lathyrus nissolia. Phytochemistry 18: 1715–1717
Robeson DJ, Ingham JL, Harborne JB (1980) Identification of two chromone phytoalexins in the sweet pea, Lathyrus odoratus. Phytochemistry 19: 2171–2173
Rogers EE, Glazebrook J, Ausubel FM (1996) Mode of action of the Arabidopsis thaliana phytoalexin camalexin and its role in Arabidopsis-pathogen interactions. Mol Plant-Microbe Interact 9: 748–757
Rosenkranz HS, Klopman G (1990) The structural basis of the carcinogenic and mutagenic potentials of phytoalexins. Mutation Res 245: 51–54
Rouxel T, Kollmann A, Boulidard L, Mithen R (1991) Abiotic elicitation of indole phytoalexins and resistance to Leptosphaeria maculans within Brassiceae. Planta 184: 271–278
Rouxel T, Kollman A, Balesdent M-H (1995) Ihytoalexins from the crucifers. In: Daniel M, Purkayastha RP (eds) Handbook of phytoalexin metabolism and action. Macel Dekker, New York, pp 229–261
Saad I, Diaz E, Chavez I, Reyes-Chilpa R, Rubluo A, Jiménez-Estrada M (2000) Antifungal monoterpene production in elicited cell suspension cultures of Piqueria trinervia. Phytochemistry 55: 51–57
Sato N, Tomiyama K, Katsui N (1968) Isolation of rishitin from tomato plants. Ann Phytopathol Soc Japan 34: 344–345
Scala F, Matthews DE, Costa M, VanEtten HD (1988) Immunochemical relatedness of fungal NADPH-cytochrome P-450 reductase and their ability to reconstitute pisatin demethylase activity. Expt Mycol 12: 377–385
Schanz S, Schröder G, Schröder J (1992) Stilbene synthase from Scots pine (Pinus sylvestres). FEBS Lett 313: 71–74
Schneider JA, Nakanishi K (1983) A new class of sweet potato phytoalexins. J Chem Soc Chem Commun 353–355
Schneider JA, Yoshihara K, Nakanishi K (1983)The absolute configuration of (+)-ipomeamarone. J Chem Soc Chem Commun 352–353
Schneider JA, Lee J, Yoshihara K, Mizukawa K, Nakanishi K (1984a) Biosynthetic studies of ipomeamarone. J Chem Soc Chem Commun 372–374
Schneider JA, Lee J, Naya Y, Nakanishi K, Oba K, Uritani I (1984b) The fate of the phytoalexin ipomeamarone: furanoterpenes and butenolides from Ceratocystis fimbriata-infected sweet potatoes. Phytochemistry 23: 759–764
Schröder J, Lanz T, Schröder G (1990) Genes for biosynthesis of stilbene-type phytoalexins. In: Lamb CJ, Beachy RN (eds) Plant gene transfer. Alan R. Liss, New York, pp 311–318
Schutt C, Netzly D (1991) Effect of apiforol and apigeninidin on growth of selected fungi. J Chem Ecol 17: 2261–2266
Seifert K, Härtling S, Porzel A, Johne S, Krauß G (1993) Phytoalexin accumulation in Orni-thopus sativus as a response to elicitor treatment. Z Naturforsch 48c: 550–555
Sharon A, Ghirlando R, Gressel J (1992) Isolation, purification, and identification of2-(p-hydroxyphenoxy)-5,7-dihydroxychromone: A fungal-induced phytoalexin from Cassia obtusifolia. Plant hysiol 98: 303–308
Sharp JK, McNeil M, Albersheim P (1984a) The primary structures of one elicitor-active and seven elicitor-inactive hexa(ß-D-glucopyranosyl)-D-glucitol isolated from the mycelial walls of Phytophthora megasperma f. sp. glycinea. J Biol Chem 259: 11321–11336
Sharp JK, Valent B, Albersheim P (1984b) Purification and partial characterization of a ß-glucan fragment that elicits phytoalexin accumulation in soybean. J Biol Chem 259: 11312–11320
Sharp JK, Albersheim P, Ossowski P, Pilotti A, Garegg PJ, Lindberg B (1984e) Comparison of the structure and elicitor activities of a synthetic and a mycelial-wall-derived hexa(ß-Dglucopyranosyl)-D-glucitol. J Biol Chem 259: 11341–11345
Sitton D, West CA (1975) Casbene: an antifungal diterpene produced in cell-free extracts of Ricinus communis seedlings. Phytochemistry 14: 1921–1925
Smith CJ (1996) Accumulation of phytoalexins: defence mechanism and stimulus response system. New Phytol 132: 1–45
Smith DA, VanEtten HD, Serum JW, Jones TM, Bateman DF, Williams TH, Coffen DL (1973) Confirmation of the structure of kievitone, an antifungal isoflavanone isolated from Rhizoctonia-infected bean tissues. Physiol Plant Pathol 3: 293–297
Smith DG, McInnes AG, Higgins VJ, Miller RL (1971) Nature of the phytoalexin produced by alfalfa in response to fungal infection. Physiol Plant Pathol 1: 41–44
Snyder BA, Nicholson RL (1990) Synthesis of phytoalexins in sorghum as a site-specific response to fungal ingress. Science 248: 1637–1639
Soby S, Bates R, VanEtten HD (1997) Oxidation of the phytoalexin maackiain to 6,6a-dihydroxymaackiain by Colletotrichum gloeosporioides. Phytochemistry 45: 925–929
Sotheeswaran S, Pasupathy V (1993) Distribution of resveratrol oligomers in plants. Phytochemistry 32: 1083–1092
Spessard GO, Hanson C, Halvorson JS, Giannini JL (1994) Effects of phaseollin on membrane leakage in red beet vacuoles and tonoplast vesicles. Phytochemistry 35: 43–47
Stelzig DA, Allen RD, Bhatia SK (1983) Inhibition of phytoalexin synthesis in arachidonic acid-stressed potato tissue by inhibitors of lipoxygenase and cyanide-resistant respiration. Plant Physiol 72: 746–749
Stermer BA, Bostock RM (1987) Involvement of 3-hydroxy-3-methylglutaryl coenzyme A reductase in the regulation of sesquiterpenoid phytoalexin synthesis in potato. Plant Physiol 84: 404–408
Stoessl A, Unwin CH, Ward EWB (1972) Post-infectional inhibitors from plants. I. Capsidiol, an antifungal compound from Capsicum frutescens. Phytopathol Z 74: 141–152
Stoessl A, Unwin CH, Ward EWB (1973) Post-infectional fungus inhibitors from plants. Fungal oxidation of capsidiol in pepper fruits. Phytopathology 63: 1225–1231
Strange RN, Subba Rao PV (1994) The phytoalexin response of groundnut and its role in disease resistance. Oléagineux 49: 227–233
Sugimura T, Koguro K, Tai A (1993) Total syntheses of (+)-ipomeamarone and (-)-ngaione. Tetrahedron Lett 34: 509–512
Sulistyowati L, Keane PJ, Anderson JW (1990) Accumulation of the phytoalexin, 6,7-dimethoxycoumarin in roots and stems of citrus seedlings following inoculation with Phytophthora citrophthora. Physiol Mol Plant Pathol 37: 451–461
Sun TJ, Melcher U, Essenberg M (1988) Inactivation of cauliflower mosaic virus by a photoactivatable cotton phytoalexin. Physiol Mol Plant Pathol 33: 115–126
Sun TJ, Essenberg M, Melcher U (1989) Photoactivated DNA nicking, enzyme inactivation, and bacterial inhibition by sesquiterpenoid phytoalexins from cotton. Mol Plant-Microbe Interact 2: 139–147
Takasugi M, Katsui N (1986) A biphenyl phytoalexin from Cercidiphyllum japonicum. Phytochemistry 25: 2751–2752
Takasugi M, Nagao S, Masamune T, Shirata A, Takahashi K (1978a) Structure of moracin A and B, new phytoalexins from diseased mulberry. Tetrahedron Lett. 797–798
Takasugi M, Nagao S, Ueno S, Masamune T, Shirata A, Takahashi K (1978b) Moracin C and D, new phytoalexins from diseased mulberry. Chem Lett 1239–1240
Takasugi M, Nagao S, Masamune T, Shirata A, Takahashi K (1979) Structures of moracin E, F. G, and H, new phytoalexins from diseased mulberry. Tetrahedron Lett 4675–4678
Takasugi M, Okinaka S, Katsui N, Masamune T, Shirata A, Ohuchi M (1985) Isolation and structure of lettucenin A, a novel guaianolide phytoalexin from Lactuca sativa var. capitata (Compositae).J Chem Soc Chem Commun 621–622
Takasugi M, Katsui N. Shirata A (1986) Isolation of three novel sulphur-containing phytoalexins from the Chinese cabbage Brassica campestris L. ssp. pekinensis (Cruciferae). 1 Chem Soc Chem Commun 1077–1078
Takasugi M, Monde K, Katsui N, Shirata A (1987a) Spirobrassinin, a novel sulfur-containing phytoalexin from the daikon Rapharus sativus L. var. hortensis ( Cruciferae ). Chem Lett 1631–1632
Takasugi M, Kawashima S, Monde K, Katsui N, Masamune T, Shirata A (1987b) Antifungal compounds from Dioscorea batatas inoculated with Pseudomonas cichorii. Phytochemistry 26: 371–375
Takasugi M, Monde K, Katsui N, Shirata A (1988) Novel sulfur-containing phytoalexins from the Chinese cabbage Brassica campestris L. ssp. pekinensis ( Cruciferae ). Bull Chem Soc Japan 61: 285–289
Takeda T, Kanemitsu T, Ishiguro M, Ogihara Y, Matsubara M (1994) Synthesis of a glycopeptide with phytoalexin elicitor activity. 1. Syntheses of a triglycosyl L-serine and a triglycosyl LSERYL-t,-PROLINE dipeptide. Carbohydr Res 256: 59–69
Tal B, Robeson DJ (1986a) The induction, by fungal inoculation, of ayapin and scopoletin biosynthesis in Helianthus annuus. Phytochemistry 25: 77–79
Tal B, Robeson DJ (1986b) The metabolism of sunflower phytoalexins ayapin and scopoletin. Plant-fungus interactions. Plant Physiol 82: 167–172
Tamogami S, Kodama 0 (2000) Coronatine elicits phytoalexin production in rice leaves (Oryza sativa L.) in the same manner as jasmonic acid. Phytochemistry 54: 689–694
Tamogami S, Mitani M, Kodama O, Akatsuka T (1993) Oryzalexin S structure: A new stemaranetype rice phytoalexin and its biogenesis. Tetrahedron 49: 2025–2032
Tamogami S, Kodama O, Hirose K, Akatsuka T (1995) Pretilachlor [2-chloro-N-(2,6-diethylphenyl-N-(2-propoxyethyl)acetamidej-and butachlor [N-butoxymethyl)-2-chloro-N-(2,6diethylphenyl)-acetamide]-induced accumulation of phytoalexin in rice (Oryza saliva) plants. J Agric Food Chem 43: 1695–1697
Tenhaken R, Salmen HC, Barz W (1991) Purification and characterization of pterocarpan hydroxylase, a flavoprotein monooxygenase from the fungus Ascochyta rabiei involved in pterocarpan phytoalexin metabolism. Arch Microbiol 155: 353–359
Thomzik JE, Stenzel K, Stoecker R, Schreier PH, Hain R, Stahl DJ (1997) Synthesis of a grapevine phytoalexin in transgenic tomatoes (Lycopersicon esculentuur Mill.) conditions resistance against Phytophthora infestans. Physiol Mol Plant Pathol 51: 265–278
Threlfall DR. Whitehead IM (1991) Terpenoid phytoalexins: aspects of biosynthesis, catabolism, and regulation. In: Harborne JB, Tomas-Barberan FA (eds) Ecological chemistry and biochemistry of plant terpenoids. Clarendon Press, Oxford, pp 159–208
Tiemann K, Hinderer W, Barz W (1987) Isolation of NADPH:isoflavone oxidoreductase, a new enzyme of pterocarpan phytoalexin biosynthesis in cell suspension cultures of Cicer arietinum. FEBS Lett 213: 324–328
Tiemann K, Inzé D, Van Montagu M, Barz W (1991) Pterocarpan phytoalexin biosynthesis in elicitor-challenged chickpea (Cicer arietinum L.) cell cultures. Purification, characterization and cDNA cloning of NADPH:isoflavone oxidoreductase. Eur J Biochem 200: 751–757
Tjamos EC, Kué.IA (1982) Inhibition of steroid glycoalkaloid accumulation by arachidonic and eicosapentaenoic acids in potato. Science 217: 542–544
Tomiyama K, Ishizaka N, Sato N, Masamune T, Katsui N (1968) Rishitin, a phytoalexin-like substance, its role in the defense reaction of potato tubers to infection. In: Hirai T (ed) Biochemical regulation in diseased plants or injury. Phytopathol Soc Jpn, Tokyo, pp 287–292
Tsuji J, Jackson EP, Gage DA, Hammerschmidt R, Somerville SC (1992) Phytoalexin accumulation in Arabidopsis thaliana during the hypersensitive reaction to Pseudomonas syringae pv. syringae. Plant Physiol 98: 1304–1309
Tsuji J, Zook M, Somerville SC, Last RL, Hammerschmidt R (1993) Evidence that tryptophan is not a direct biosynthetic intermediate of camalexin in Arabidopsis thaliana. Physiol Mol Plant Pathol 43: 221–229
Turbek CS, Li DL, Choi GH, Schardl CL, Smith DA (1990) Induction and purification ofkievitone hydratase from Fusarium solani f. sp. phaseoli. Phytochemistry 29: 2841–2846
Uegaki R, Fujimori T, Kubo S, Kato K (1981) Sesquiterpenoid stress compounds from Nicotiana species. Phytochemistry 20: 1567–1568
Uegaki R, Kubo S, Fujimori T (1988) Stress compounds in the leaves of Nicotiana undulata induced by TMV inoculation. Phytochemistry 27: 365–368
Urech J, Fechtig B, Nuesch J, Vischer E (1963) Hircinol, eine antifungisch wirksame Substanz aus Knollen von Loroglossum hircinum ( L.) Rich. HeIv Chim Acta 46: 2758–2766
VanEtten HD, Pueppke SG (1976) Isoflavonoid phytoalexins. In: Friend J, Threlfall DR (eds) Biochemical aspects of plant-parasite relationships. Academic Press, New York, pp 239–289
VanEtten HD, Matthews PS, Tegtmeier KJ, Dietert MF, Stein JI (1980) The association of pisatin tolerance and demethylation with virulence on pea in Nectria haematococca. Physiol Plant Pathol 16: 257–268
VanEtten HD, Matthews DE, Matthews PS (1989) Phytoalexin detoxification: importance for pathogenicity and practical implications. Annu Rev Phytopathol 27: 143–164
Van der Heijden R, Threlfall DR, Verpoorte R, Whitehead IM (1989) Regulation and enzymology of pentacyclic triterpenoid phytoalexin biosynthesis in cell suspension cultures of Tabernaemontana divaricata. Phytochemistry 28: 2981–2988
Van den Heuvel J, VanEtten HD, Serum JW, Coffen DL, Williams TH (1974) Identification of lahydroxyphaseol lone, a phaseollin metabolite produced by Fusarium solani. Phyto-chemistry 13: 1129–1131
Vernenghi A, Ramiandrasoa F, Chuilon S, Ravise A (1987) Citrus phytoalexins: seselin biological activity and in vitro synthesis stimulation. Fruits 42: 103–111
Vögeli U, Chappell J (1988) Induction of sesquiterpene cyclase and suppression of squalene activities in plant cell cultures treated with fungal elicitor. Plant Physiol 88: 1291–1296
Vögeli U, Freeman JW, Chappell J (1990) Purification and characterization of an inducible sesquiterpene cyclase from elicitor-treated tobacco cell suspension cultures. Plant Physiol 93: 182–187
Volpin H, Phillips DA, Okon Y, Kapulnik Y (1995) Suppression of an isoflavonoid phytoalexin defense response in mycorrhizal alfalfa roots. Plant Physiol 108: 1449–1454
Ward EWB, Unwin CH, Stoessl A (1975a) Loroglossol: an orchid phytoalexin. Phytopathology 65: 632–633
Ward EWB, Unwin CH, Hill J, Stoessl A (1975b) Sesquiterpenoid phytoalexins from fruits of eggplants. Phytopathology 675: 859–863
Ward EWB, Stoessl A, Stothers JB (1977) Metabolism of the sesquiterpenoid phytoalexins capsidiol and rishitin to their 13-hydroxy derivatives by plant cells. Phytochemistry 16: 2024–2025
Ward EWB, Cahill DM, Bhattacharyya MK (1989) Abscisic acid suppression of phenylalanine ammonia-lyase activity and mRNA, and resistance of soybeans to Phytophthora megasperma fsp. glycinea. Plant Physiol 91: 23–27
Watanabe K, Ishiguri Y, Nonaka F, Morita A (1982) Isolation and identification of aucuparin as a phytoalexin from Eriobotrya japonica. Agric Biol Chem 46: 567–568
Watanabe K, Widyastuti SM, Nonaka F (1990) Two biphenyl compounds from Rhaphiolepsis umbellata as its phytoalexin. Agric Biol Chem 54: 1861–1862
Weidemann C, Tenhaken R, Höhl U, Barz W (1991) Medicarpin and maackiain 3-O-glucoside-6’O-malonate conjugates are constitutive compounds in chickpea (Cier arietinum L.) cell cultures. Plant Cell Reptr 10: 371–374
Weinstein LI, Hahn MG, Albersheim P (1981) Host-pathogen interactions: XVIII. Isolation and biological activity of glycinol, a pterocarpan phytoalexin synthesized by soybeans. Plant Physiol 68: 358–363
Weissenborn DL, Denbow CJ, Laine M, Lang SS, Yang Z, Yu X, Cramer CL (1995) HMG-CoA reductase and terpenoid phytoalexins: Molecular specialization within a complex pathway. Physiol Plant 93: 393–400
Welle R, Grisebach H (1988a) Induction of phytoalexin synthesis in soybean: Enzymatic cyclization ofprenylated pterocarpans to glyceollin isomers. Arch Biochem Biophys 263: 191–198
Welle R, Grisebach H (1988b) Isolation of a novel NADPH-dependent reductase which coacts with chalcone synthase in the biosynthesis of 6’-deoxychalcone. FEES Lett 236: 221–225
Welle R, Grisebach H (1989) Phytoalexin synthesis in soybean cells: Elicitor induction of reductase involved in biosynthesis of 6’-deoxychalcone. Arch Biochem Biophys 272: 97–102
Welle R, Grisebach H (1991) Properties and solubilization ofthe prenyltransferase of iso-flavonoid phytoalexin biosynthesis in soybean. Phytochemistry 30: 479–484
Welle R, Schröder J (1992) Expression cloning in Escherichia coli and preparative isolation of the reductase coacting with chalcone synthase during the key step in the biosynthesis of soybean phytoalexin. Arch Biochem Biophys 293: 377–381
Weltring K-M, Schaub H-P, Barz W (1995) Metabolism of pisatin stereoisomers by Ascochyta rabiei strains transformed with the pisatin demethylase gene of Nectria haematococca MP VI. Mol Plant-Microbe Interact 8: 499–505
West,CA, Lois AF, Wickham KA, Ren Y-Y (1990) Diterpenoid phytoalexins: Biosynthesis and regulation. Recent Advances in Phytochemistry 24: 219–248
Whitehead IM, Threlfall DR, Ewing DF (1987) cis-9, I 0-Dihydrocapsenone: a possible catabolite of capsidiol from cell suspension cultures of Capsicum annuum. Phytochemistry 26: 1367–1369
Whitehead IM, Ewing DF, Threlfall DR (1988) Sesquiterpenoids related to the phytoalexin debneyol from elicited cell suspension cultures of Nicotiana tabacum. Phytochemistry 27: 1365–1370
Whitehead IM, Threlfall DR, Ewing DF (1989) 5-epi-Aristolochene is a common precursor of the sesquiterpenoid phytoalexins capsidiol and debneyol. Phytochemistry 28: 775–779
Whitehead IM, Atkinson AL, Threlfall DR (1990) Studies on the biosynthesis and metablism of the phytoalexin lubimin and related compounds in Datura stramonium L. Planta 182: 81–88
Wichkam KA, West CA (1992) Biosynthesis of rice phytoalexins: identification of putative diterpene hydrocarbon precursors. Arch Biochem Biophys 293: 320–332
Widyastuti SM, Nonaka F, Watanabe K, Sako N, Tanaka K (1992) Isolation and characterization of two aucuparin-related phytoalexins from Photinia glabra Maxim. Ann Phytopathol Soc Japan 58: 228–233
Woodward MD (1979a) Phaseoluteone and other 5-hydroxyisoflavonoids from Phaseolus vulgaris. Phytochemistry 18: 363–365
Woodward MD (1979b) New isoflavonoids related to kievitone from Phaseolus vulgaris. Phytochemistry 18: 2007–2010
Woodward MD (1980) Phaseollin formation and metabolism in Phaseolus vulgaris. Phytochemistry 19: 921–927
Wu Q, Presig CL, Vanetten HD (1997) Isolation of the cDNAs encoding (+)6a-hydroxymaackiain 3-O-methyltransferase, the terminal step for the synthesis of the phytoalexin pisatin in Pisum sativum. Plant Mol Biol 35: 551–560
Yajima A, Mori K (2000) Absolute configuration of phytocassanes as proposed on the basis of the CD spectrum of synthetic (+)-2-deoxyphytocassane A. Tetrahedron Lett 41: 351–354
Yamada A, Shibuya N, Kodama O, Akatsuka T (1993) Induction of phytoalexin formation in suspension-cultured rice cells by N-acetylchitooligosaccahrides. Biosci Biotech Biochem 57: 405–409
Yang D, Hubbes Mir, Jeng RS, Hubbes M (1994) A glycoprotein isolated from culture filtrates of Ophiostoma ulmi as a mansonone-inducing elicitor on elm callus. Mycol Res 98: 295–300
Yang Z, Park H, Lacy Gli, Cramer CL (1991) Differential activation of potato 3-hydroxy-3methylglutaryl coenzyme A reductase genes by wounding and pathogen challenge. Plant Cell 3: 397–405
Yoshikawa M, Onoe T, Masago H, Sagawa H (1987) Ultrastructural in situ evidence for the role of glyceollin in the expression of soybean resistance to fungal infection. Ann Phytopathol Soc Japan 53: 227–241
Yoshikawa M, Tsuda M, Takeuchi Y (1993) Resistance to fungal diseases in transgenic tobacco plants expressing the phytoalexin elicitor-releasing factor, 3- l,3-endogiucanase, from soybean. Natu rwi ssensch. 80: 417–420
Yoshizawa Y, Yamaura T, Kawaii S, Hoshino T, Mizutani J (1994) Incorporation of 13C-labelled 5-epi-aristolochene into capsidiol in green pepper seedlings. Biosci Biotech Biochem 58: 304–308
Zhang J, Mace ME, Stipanovic RD, Bell AA (1993) Production and fungitoxicity of the terpenoid phytoalexin in cotton inoculated with Fusarium oxysporum f. sp. vasinfectum. J Phytopathol 139: 247–252
Zhao J, Last RL (1996) Coordinate regulation of the tryptophan biosynthetic pathway and indolic phytoalexin accumulation in Arabidopsis. Plant Cell 8: 2235–2244
Zook M, Hammerschmidt (1997) Origin of the thiazole ring of camalexin, a phytoalexin from Arabidopsis thaliana. Plant Physiol 113: 463–468
Zook MN, Kue JA (1991) Induction of sesquiterpene cyclase and suppression of squalene synthase activity in elicitor-treated or fungal-infected potato tuber tissue. Physiol Mol Plant Pathol 39: 377–390
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Huang, JS. (2001). Accumulation of Phytoalexins as a Resistance Mechanism. In: Plant Pathogenesis and Resistance. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-2687-0_9
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DOI: https://doi.org/10.1007/978-94-017-2687-0_9
Publisher Name: Springer, Dordrecht
Print ISBN: 978-90-481-5750-1
Online ISBN: 978-94-017-2687-0
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