The effect of stereochemistry on the biological activity of natural phytotoxins, fungicides, insecticides and herbicides

Chirality

Volumn 25, Issue 2, 2013, Pages 59-78

  Evidente, Antonio ^a   Cimmino, Alessio ^a   Andolfi, Anna ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

fungicides; herbicides; insecticides; phytotoxins; relative and or absolute configuration; structure activity relationships

Indexed keywords

FUNGICIDE; HERBICIDE; INSECTICIDE; ISOFLAVONOID; MEDICARPIN; PLANT TOXIN; POLYPHENOL; SOYASAPOGENOL B;

ANTIFUNGAL ACTIVITY; ASPERGILLUS; BIOLOGICAL ACTIVITY; BIOLOGICAL PEST CONTROL; BOTRYTIS FABAE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; CONFORMATION; CROP MANAGEMENT; CROP PEST; ENANTIOMER; ENDOPHYTE; FUNGAL PLANT DISEASE; GALACTOMYCES GEOTRICHUM; GERMINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MONOCOT; NONHUMAN; PLANT ROOT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; REVIEW; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; TRICHODERMA VIRIDE; X RAY CRYSTALLOGRAPHY;

ANTIFUNGAL AGENTS; BIOLOGICAL PRODUCTS; HERBICIDES; INSECTICIDES; PESTICIDES; PLANTS; STEREOISOMERISM;

EID: 84872840614     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22124     Document Type: Review

References (140)

1. Strobel GA,. Phytotoxins. Ann Rev Biochem 1982; 51: 309-333.
2. Graniti A, Durbin RD, Ballio A,. Phytotoxins and plant pathogenesis. NATO ASI Series, Series H, Vol. 27. Berlin: Springer-Verlag; 1989. p 508.
3. Ballio A, Graniti A,. Phytotoxins and their involvement in plant disease. Experientia 1991; 47: 751-826.
4. Evidente A,. Bioactive metabolites from phytopathogenic fungi and bacteria. In:, Pandalai SG, editor. Recent research developments in phytochemistry. Trivandrum (India): Research Signpost; 1997. p 255-292.
5. Evidente A, Motta A,. Phytotoxins from fungi pathogenic for agrarian, forestal and weedy plants. In:, Tringali C, editor. Bioactive compounds from natural sources. London: Taylor & Francis; 2001. p 473-525.
6. Rimando AM, Duke OS,. Natural products for pest management. In:, Rimando AM, Duke OD, editors. Natural products for pest management. ACS Symposium Series 927. Washington DC: Oxford University Press; 2006. p 2-23.
7. Evidente A,. Chemical and biological characterization of toxins produced by weed pathogenic fungi as potential natural herbicides. In:, Rimando AM, Duke OD, editors. Natural products for pest management. ACS Symposium Series 927. Washington, DC: Oxford University Press; 2006. p 62-75.
8. Evidente A, Abouzeid M,. Characterization of phytotoxins from phytopathogenic fungi and their potential use as herbicides in integrated crop management. In:, Singh HP, Batish DR, Kholi RK, editors. Handbook of sustainable weed management. New York: The Harworth Press Inc; 2006. p 507-532.
9. Evidente A, Andolfi A, Cimmino A,. Fungal phytotoxins for control of Cirsium arvense and Sonchus arvensis. Pest Technol 2011; 5: 1-17.
10. Gullan PG, Cranston PS,. The insects: an outline of entomology. Oxford: Blackwell; 2005.
11. De Lucia EH, Casteel CL, Nabity PD, O'Neill BF,. Insects take a bigger bite out in a warmer, higher carbon dioxide world. Proc Natl Acad Sci U S A 2008; 50: 2943-2945.
12. Inbar M, Gerling D,. Plant-mediated interactions between whiteflies, herbivores, and natural enemies. Ann Rev Entomol 2008; 53: 431-448.
13. Strobel GA, Sugawara F, Clardy J,. Phytotoxins from plant pathogens of weedy plants. In:, Waller GR, editor. Allelochemicals: role in agriculture and forestry. ACS Symposium Series 330. Washington, DC: American Chemical Society; 1987. p 516-523.
14. Duke SO, Baerson SR, Dayan E, Rimando AM, Scheffler BE, Tellez MR, Wedge DE, Schrader KK, Akey DH, Arthur FH, De Lucca AJ, Gibson DM, Harrison HF Jr, Peterson K, Gealy DR, Tworkoski T, Wilson CL, Morris JB,. United States Department of Agriculture-Agriculture Research Service research on natural products for pest management. Pest Manag Sci 2003; 59: 708-717.
15. Opender K,. Natural products leads as anti-insect compounds. Prospects for biotechnology. In:, Ananthakrishnan TN, editor. Biotechnological prospective in chemical ecology of insects. New Delhi: Oxford & IBH Publishing Co. Ltd., 1996. p 15-27.
16. Santino A, Poltronieri P, Mita G,. Advances on plant products with potential to control toxigenic fungi: a review. Food Addit Contam 2005; 22: 389-395.
17. Evidente A,. New fungal metabolites, as antifungal, herbicides and insecticides for biocontrol of agrarian plants pests. In:, Gupta VK, editor. Comprehensive bioactive natural products, Vol. 1. Houston: Studium Press LLC; 2010. p 333-339.
18. Denman S, Crous PW, Taylor JE, Kang JC, Pasco I, Wingfield MJ,. An overview of the taxonomic history of Botryosphaeria, and a re-evaluation of its anamorphs based on morphology and ITS rDNA phylogeny. Stud Mycol 2000; 45: 129-140 (and references therein cited).
19. Van Niekerk JM, Fourie PH, Halleen F, Crous PW,. Botryosphaeria spp. as grapevine trunk disease pathogens. Phytopathol Mediterr 2006; 45 suppl: S43-S54.
20. Evidente A, Punzo B, Andolfi A, Cimmino A, Melck D, Luque J,. Lypophilic phytotoxins produced by Neofusicoccum parvum, a grapevine canker agent. Phytopathol Mediterr 2010; 49: 74-79.
21. Cabras A, Mannoni MA, Serra S, Andolfi A, Fiore M,. Occurrence, isolation and biological activity of phytotoxic metabolites produced in vitro by Sphaeropsis sapinea, pathogenic of Pinus radiata. Eur J Plant Pathol 2006; 115: 187-193.
22. Turner WB, Aldridge DC,. Fungal metabolites II. London: Academic Press; 1983. p 82-109.
23. Camarda L, Merlini L, Nasini G,. Metabolites of Cercospora. Taiwapyrone, an α-pyrone of unusual structure from Cercospora taiwanensis. Phytochemistry 1976; 15: 537-539.
24. Venkatsubbaiah P, Chilton WS,. Phytotoxins of Botryospheria obtuse. J Nat Prod 1990; 53: 1628-1630.
25. Arakawa H, Torimoto M, Masu Y,. Bestimmung der absoluten Konfiguration von Agrimonolid und Mellein. Liebigs Ann Chem 1969; 728: 152-157.
26. Horeau A, Kagan HB,. Détermination des configurations par "dédoublement partiel"-III. Alcools stéroides. Tetrahedron 1964; 20: 2431-2441.
27. 2HN.M.R. Spectroscopy to determine the origin of the C-4 hydroxy group. J Chem Soc Chem Commun 1987; 586-587.
28. Devys M, Barbier M, Bousquet JF, Kollmann A,. Isolation of the new (-)-(3R,4S)-4-hydroxymellein from the fungus Septoria nodorum Berk. Z Naturforsch C 1992; 47: 779-881.
29. Kron K, Koch I, Elsässer B, Flörke U, Schulz B, Draeger S, Piscitelli G, Antus S, Kurtán T,. Bioactive natural products from the endophytic fungus Ascochyta sp. from Meliotus dentatus-Configurational assignment by solid-state CD and TDDFT calculations. Eur J Org Chem 2007; 1123-1129.
30. Andolfi A, Mugnai L, Luque J, Surico G, Cimmino A, Evidente A,. Phytotoxins produced by fungi associated with grapevine trunk disease. Toxins 2011; 3: 1569-1605.
31. Cimmino A, Villages-Fernández AM, Andolfi A, Melck D, Rubiales D, Evidente A,. Botrytone, a new naphthalenone pentaketide produced by Botrytis fabae, the causal agent of chocolate spot disease on Vicia faba. J Agric Food Chem 2011; 59: 2901-2906.
32. Liu Q, Zhao P, Li X-C, Jacob MR, Yang C-R, Zhang Y-J,. New-tetralone galloylglucosides from fresh pericarps of Juglans sigillata. Helv Chim Acta 2010; 93: 265-271.
33. Min BS, Nakamura N, Miyashiro H, Kim YH, Hattori M,. Inhibition of human immunodeficient virus type 1 reverse transcriptase and ribonuclease H activities by constituents of Juglans mandshurica. Chem Pharm Bull 2000; 48: 194-200.
34. Liu L, Li W, Koike K, Zhang S, Nikaido T,. New α-tetralonyl glucoside from the fruit of Juglans mandhurica. Chem Pharm Bull 2004; 52: 566-569.
35. Fujimoto Y, Yokoyama E, Takahashi T, Uzawa J, Morooka N, Tsunoda H, Tarsuo T,. Studies on the metabolites of Penicillium diversum var. aurem. I. Chem Pharm Bull 1986; 34: 1497-1500.
36. Bürki N, Michel A, Tabacchi R,. Naphthalenones and isocoumarins of the fungus Ceratocystis fimbriata f. sp. platani. Phytopathol Mediterr 2003; 42: 191-198 (and references therein cited).
37. Hoss R, Helbig J, Bochow H,. Function of host fungal metabolites in resistance response of banana and plantain in the Black sigatoka disease pathosystem (Musa spp.- Mycosphaerella fijiensis). J Phytopathol 2000; 148: 387-394 (and references therein cited).
38. Ayer WA, Trifonov LS, Hutchison LJ, Chakravarty P,. Metabolites from a wood-inhabiting cup fungus, Ursula craterium. Nat Prod Lett 2000; 14: 405-410.
39. Fujimoto Y, Satoh M,. Studies on the metabolites of Penicillium diversum var. aureum. II. Synthesis and cytotoxic activity of trihydroxytetralones. Chem Pharm Bull 1986; 34: 4540-4544.
40. Evidente A, Superchi S, Cimmino A, Mazzeo G, Mugnai L, Rubiales D, Andolfi A, Villegas-Fernández AM,. Regiolone and isosclerone, two enantiomeric phytotoxic naphthalenone pentaketides: computational assignment of absolute configuration and its relationship with phytotoxic activity. Eur J Org Chem 2011; 5564-5570 (and references therein cited).
41. Berova N, Nakanishi K,. Exciton chirality method: principles and applications. In, Berova N, Nakanishi K, Woody RW, editors. Circular dichroism: principles and applications, 2nd ed. New York: Wiley-VCH; 2000; 337-382.
42. Morita T, Aoki H,. Isosclerone, a new metabolite of Sclerotinia sclerotiorum (lib.) De Bary. Agr Biol Chem 1974; 38: 1501-1505.
43. Talapatra SK, Karmacharya B, De SC, Talapatra B,. (-)-regiolone, an α-tetralone from Juglans regia: structure, stereochemistry and conformation. Phytochemistry 1988; 27: 3929-3932.
44. Lee C, Yang W, Parr RG,. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 1988; 37: 785-789.
45. Becke AD,. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 1993; 98: 5648-5652.
46. Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ,. Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J Phys Chem 1994; 98: 11623-11627.
47. Ge HM, Zhu CH, Shi DH, Zhang LD, Xie DQ, Yang J, Ng SW, Tan RX,. ChemInform abstract: hopeahainol A: an acetylcholinesterase inhibitor from Hopea hainanensis. Chem Eur J 2008; 14: 376-381.
48. Xu DQ, Wang YF, Luo SP, Zhang S, Zhong AG, Chen H, Xu ZY,. A novel enantioselective catalytic tandem oxa-Michael/Henry reaction: one-pot organocatalytic asymmetric synthesis of 3-nitro-2H-chromenes. Adv Synth Catal 2008; 350: 2610-2616.
49. Gioia C, Fini F, Mazzanti A, Bernardi L, Ricci A,. Organocatalytic asymmetric formal [3 + 2] cycloaddition with in situ-generated N-carbamoyl nitrones. J Am Chem Soc 2009; 131: 9614-9615.
50. Hussain H, Akhtar N, Draeger S, Schulz B, Pescitelli G, Salvadori P, Antus S, Kurtan T, Khron K,. New bioactive 2,3-epoxycyclohexenes and isocoumarins from the endophytic fungus Phomopsis sp. from Laurus azorica. Eur J Org Chem 2009; 749-756.
51. Machida K, Matsuoka E, Kasahara T, Kikuchi M,. Studies on the constituents of Juglans species. I. Structural determination of (4S)- and (4R)-4-hydroxy-α-tetralone derivatives from the fruit of Juglans mandshrica Maxim. var. sieboldiana Makino. Chem Pharm Bull 2005; 53: 934 Laurus Azorica 937.
52. Moscowitz A,. Action of light and organic crystals. In:, Sinanoglu O, editor. Modern quantum chemistry, Part III. London: Academic Press; 1965. p 31.
53. Harrison JG,. The biology of Botrytis spp. on Vicia beans and chocolate spot disease-a review. Plant Pathol 1988; 37: 168-201.
54. Staats M, van Baarlen P, van Kan JAL,. Molecular phylogeny of the plant pathogenic genus Botrytis and the evolution of host specificity. Mol Biol Evol 2005; 22: 333-346.
55. Evidente A, Andolfi A, Cimmino A,. Relationships between the stereochemistry and biological activity of fungal phytotoxins. Chirality 2011; 23: 674-693.
56. Choi EM, Hwang JK,. Antiinflammatory, analgesic and antioxidant activities of the fruit of Foeniculum vulgare. Fitoterapia 2004; 75: 557-565.
57. Rodeva R, Gabler J,. Umbel browning and stem necrosis: a new disease of fennel in Bulgaria. J Phytopathol 2010; 159: 184-187.
58. Nair MSR, Carey ST,. Metabolites of pyrenomycetes II: nectriapyrone, an antibiotic monoterpenoid. Tetrahedron Lett 1975; 19: 1655-1658.
59. Evidente A, Rodeva R, Andolfi A, Stoyanova Z, Perrone C, Motta A,. Phytotoxic polyketides produced by Phomopsis foeniculi, a strain isolated from diseased Bulgarian fennel. Eur J Plant Pathol 2011; 130: 173-182 (and references therein cited).
60. Guimaraes DO, Borges WS, Kawano CY, Ribeiro PH, Goldman GH, Nomizo A, Thiemann OH, Oliva G, Lopes NP, Pupo MT,. Biological activities from extracts of endophytic fungi isolated from Viguiera arenaria and Tithonia diversifolia. FEMS Immun Med Microbiol 2008; 52: 34-144.
61. Lee IK, Yun BS, Oh S, Kim YH, Lee MK, Yoo ID,. 5-Methylmellein and nectriapyrone, two new monoamine oxidase inhibitors. Med Sci Res 1999; 27: 463-465.
62. Thines E, Anke H, Sterner O,. Scytalols A, B, C, and D and other modulators of melanin biosynthesis from Scytalidium sp. 36-93. J Antibiot 1998; 51: 387-393.
63. Stoessl A,. Some metabolites of Alternaria solani. Can J Chem 1969; 47: 767-776.
64. Becker AM, Rickards RW, Schmalzl KJ, Yick HC,. Metabolites of Dactylaria lutea. The structures of dactylariol and the antiprotozoal antibiotic dactylarin. J Antibiot 1978; 31: 324-329.
65. 2Hnmr studies. Can J Chem 1983; 61: 372-377.
66. Holler U, Gloer JB, Wicklow DT,. Biologically active polyketide metabolites from an undetermined fungicolous hyphomycete resembling Cladosporium. J Nat Prod 2002; 65: 876-882.
67. Suemitsu R, Nakajima M, Hiura M,. Studies on the metabolic products of Macrosporium porri Elliott. Part III. Structure of macrosporin. Bull Agric Chem Soc Japan 1959; 23: 547-551.
68. Evidente A, Lanzetta R, Abouzeid MA, Corsaro MM, Mugnai L, Surico G,. Foeniculoxin, a new phytotoxic geranylhydroquinone from Phomopsis foeniculi. Tetrahedron 1994; 50: 10371-10378.
69. Corsaro MM, De Castro C, Evidente A, Lanzetta R, Molinaro A, Mugnai L, Parrilli M, Surico G,. Chemical structure of two phytotoxic exopolysaccharides produced by Phomopsis foeniculi. Carbohydr Res 1998; 308: 349-357.
70. Vurro M, Evidente A, Andolfi A, Zonno MC, Giordano F, Motta A,. Brefeldin A and α,β-dehydrocurvularin, two phytotoxins from Alternaria zinniae, a biocontrol agent of Xanthium occidentale. Plant Sci 1988; 138: 67-79.
71. Evidente A, Andolfi A, Cimmino A, Vurro M, Fracchiolla M, Charudattan R,. Herbicidal potential of ophiobolins produced by Drechslera gigantea. J Agric Food Chem 2006; 54: 1779-1783.
72. Sparapano L, Bruno G, Fierro O, Evidente A,. Studies on structure-activity relationships of sphaeropsidins A-F, phytotoxins produced by Sphaeropsis sapinea f. sp. cupressi. Phytochemistry 2004; 65: 189-198.
73. Evidente A, Fiore M, Bruno G, Sparapano L, Motta A,. Chemical and biological characterization of sapinopyridione, a phytotoxic 3,3,6-trisubstituted-2,4-pyridione produced by Sphaeropsis sapinea, a toxigenic pathogen of native and exotic conifers, and its derivatives. Phytochemistry 2006; 67: 1019-1028.
74. Yürüt HA, Erkal Ã, Gürer M,. Hazelnut diseases in Bolu, Zonguldak and Bartin. Proceedings of the 9th Congress of the Mediterranean Phytopathological Union, Turkish Phytopathological Society Publications, No.7, Kuşadasi-Aydin, Turkey; 1994. p 417-419.
75. Turkkan M, Andolfi A, Zonno MC, Erper I, Perrone C, Cimmino A, Vurro M, Evidente A,. Phytotoxins produced by Pestalotiopsis guepinii, the causal agent of hazelnut twig blight. Phytopathol Mediterr 2011; 50: 154-158 (and references therein cited).
76. Venkatasubbaiah P, van Dyke CG, Chilton WS,. Phytotoxins produced by Pestalotiopsbox drawings light down and lefts oenotherae, a pathogen of evening primrose. Phytochemistry 1991; 30: 1471-1474.
77. Evidente A, Masi M, Linaldedu BT, Franceschini A, Scanu B, Cimmino A, Andolfi A, Motta A, Maddau L,. Afritoxinones A and B, dihydrofuropyran-2-ones produced by Diplodia africana the causal agent of branch dieback on Juniperus phoenicea. Phytochemistry 2012; 77: 245-250.
78. Pinkerton F, Strobel G,. Serinol as an activator of toxin production in attenuated cultures of Heminthosporium sacchari. Proc Natl Acad Sci U S A 1976; 73: 4007-4011.
79. Evidente A, Zonno MC, Andolfi A, Troise C, Cimmino A, Vurro M,. Phytotoxic α-pyrones produced by Pestalotiopsis guepinii, the causal agent of hazelnut twig blight. J Antibiot 2012; 1-4 (and references therein cited).
80. Kimura Y, Mcgahren WJ, Suzuki A, Tamura S,. Structure of a new fungal pyrone from an unidentified Penicillium sp. Agric Biol Chem 1978; 42: 1625-1626.
81. 13C NMR spectra of pestalotin and its analogues. Agric Biol Chem 1980; 44: 451-452 (and references therein cited).
82. Ohtani I, Kusumi T, Kashman Y, Kakisawa H,. New bioactive triterpenoids from Melia volkensi. J Am Chem Soc 1991; 113: 4092-4096.
83. Marras F, Maddau L, Franceschini A, Corda P, Bottalico A,. Screening of antagonistic fungal strains for biological control of Sclerotium and Sclerotinia crown and stem rot of artichoke. Proceedings of the 9th Congress of the Mediterranean Phytopathological Union, Kusadasi-Aydin, Turkey; 1994. p 197-199.
84. Spiga D, Marras F, Maddau L, Franceschini A, Corda P,. Prove preliminari di lotta contro il "Marciume del colletto" del carciofo da Sclerotium rolfsii mediante Trichoderma viride. Notiziario sulla Protezione delle Piante 1998; 8: 173-179.
85. Mannina L, Segre AL, Ritieni A, Fogliano V, Vinale F, Randazzo G, Maddau L, Bottalico A,. A new fungal growth inhibitor from Trichoderma viride. Tetrahedron 1997; 53: 3135-3144.
86. Cooney JM, Denis RL, Poole PR, Whitaker G,. Microbial transformation of the Trichoderma metabolites 6-n-pentyl-2H-pyran-2-one. J Nat Prod 1997; 60: 1242-1244.
87. Evidente A, Cabras A, Maddau L, Serra S, Andolfi A, Motta A,. Viridepyronone, a new antifungal 6-substituted 2H-pyran-2-one produced by Trichoderma viride. J Agr Food Chem 2003; 51: 6957-6969.
88. Evidente A, Cabras A, Maddau L, Marras F, Andolfi A, Melck D, Motta A,. Viridenepoxydiol a new pentasubstituted oxiranyldecene produced by Trichoderma viride. J Agric Food Chem 2006; 54: 6588-6592.
89. Matsumori N, Kaneno D, Murata M, Nakamura H, Tachibana K,. Stereochemical determination of acyclic structures based on carbon-proton spin-coupling constants. A method of configurational analysis for natural products. J Org Chem 1999; 64: 866-876.
90. Mangoni A, Esposito V, Randazzo A,. Configuration assignment in small organic molecules via residual dipolar couplings. Chem Commun 2003; 154-155.
91. Moreno-Manas M, Pleixats R,. Dehydroacetic acid, triacetic acid lactone and related pyrones. In:, Katritzky AR, editor. Advances in heterocyclic chemistry, Vol. 53. San Diego, CA: Academic Press; 1992. p 1-84 (and references therein cited).
92. Tanaka Y, ̄Omura S,. Agroactive compounds of microbial origin. Ann Rev Microbiol 1993; 47: 57-87.
93. Ganassi S, De Cristofaro A, Grazioso P, Altomare C, Logrieco A, Sabatini MA,. Detection of fungal metabolites of various Trichoderma species by the aphid Schizaphis graminum. Entomol Exp Appl 2007; 122: 77-86 (and references therein cited).
94. Evidente A, Ricciardiello G, Andolfi A, Sabatini MA, Ganassi S, Altomare C, Favilla M, Melck D,. Citrantifidiene and citrantifidiol: bioactive metabolites produced by Trichoderma citrinoviride with potential antifeedant activity toward aphids. J Agric Food Chem 2008; 56: 3569-3573 (and references therein cited).
95. Nagano H, Tori M, Shiota M, De Pascual TJ,. 400 MHz proton nuclear magnetic resonance study of magydardienediol, a diterpene from Magydaris panacifolia. Bull Chem Soc Japan 1984; 57: 2971-2975.
96. Evidente A, Andolfi A, Cimmino A, Ganassi S, Altomare C, Favilla M, De Cristofaro A, Vitagliano S, Sabatini MA,. Bisorbicillinoids produced by the fungus Trichoderma citrinoviride affect feeding preference of the aphid Schizaphis graminum. J Chem Ecol 2009; 35: 533-541.
97. Sperry S, Samuels GJ, Crews P,. Vertinol polyketides from the saltwater culture of the fungus Trichoderma longibrachiatum separated from a Haliclona marine sponge. J Org Chem 1998; 63: 10011-10014.
98. Shirota O, Pathak V, Hossain CF, Sekita S, Takatori K, Satake M,. Structural elucidation of trichotetronines: polyketides possessing a bicyclo[2.2.2]octane skeleton with tetronic acid moiety isolated from Trichoderma sp. J Chem Soc Perkin Trans I 1997; 2961-2964.
99. Liu W, Gu Q, Zhu W, Cui C, Fan G,. Dihydrotrichodimerol, and tetrahydrotrichodimerol, two new bisorbicillinoids, from a marine-derived Penicillium terrestre. J Antibiot 2005; 58: 621-624.
100. Mosmann T,. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65: 55-63.
101. Maskey RP, Grun-Wollny I, Laatsgh H,. Sorbicillin analogues and related dimeric compounds from Penicillium notatum. J Nat Prod 2005; 68: 865-870 (and references therein cited).
102. Gao Q, Leet JE, Thomas ST, Matson JA,. Crystal structure of trichodimerol. J Nat Prod 1995; 58: 1817-1821.
103. Saidou Balde E, Andolfi A, Bruyère C, Cimmino A, Lamoral-Theys D, Vurro M, Van Damme M, Altomare C, Mathieu V, Kiss R, Evidente A,. Investigation of fungal secondary metabolites with potential anticancer activity. J Nat Prod 2010; 73: 969-971.
104. Holm LG, Pluckett DL, Pancho JV, Herberger JP,. The world's worst weeds (distribution and biology). Honolulu: University Press of Hawaii; 1977. p 84-91.
105. Naylor RE,. Weed management handbook. Oxford: Blackwell Publishing; 2002.
106. Chandramohan S, Charudattan R,. Control of seven grasses with a mixture of three fungal pathogens with restricted host range. Biol Control 2001; 22: 246-255.
107. Kastanias MA, Tokousbalides MC,. Herbicidal potential of pyrenophorol isolated from a Drechslera avenae pathotype. Pest Manag Sci 2000; 56: 227-232 (and references therein cited).
108. Evidente A, Andolfi A, Vurro M, Fracchiolla M, Zonno MC, Motta A,. Drazepinone, a tetrasubstituted tetrahydronaphthofuroazepinone with herbicidal activity produced by Drechslera siccans Phytochemistry 2005; 66: 715-721.
109. Baudoin O, Cesario M, Guénard D, Guéritte F,. Application of the palladium-catalyzed borylation/suzuki coupling (BSC) reaction to the synthesis of biologically active biaryl lactams. J Org Chem 2002; 67: 1199-1207 (and references therein cited).
110. Sivanesan A,. IMI descriptions of fungi and bacteria no. 1123. Drechslera gigantea. Mycopathologia 1992; 119: 49-50.
111. Chandramohan S, Charudattan R, Sonoda R, Singh M,. Field evaluation of a fungal pathogen mixture for the control of seven weedy grasses. Weed Sci 2002; 50: 204-213.
112. Kenfield D, Bunkers G, Wu YH, Strobel G, Sugawara F, Hallock Y, Clardy J,. Gigantenone, a novel sesquiterpene phytormone mimic. Experientia 1989; 45: 900-902.
113. Au TK, Chick WSH, Leung PC,. The biology of ophiobolins. Life Sci 2000; 67: 733-742 (and references therein cited).
114. Evidente A, Andolfi A, Cimmino A, Vurro M, Fracchiolla M, Charudattan R, Motta A,. Ophiobolin E and 8-epi-ophiobolin J by Drechslera gigantea, potential mycoherbicides of weedy grasses. Phytochemistry 2006; 67: 2281-2287.
115. 25 terpenoides. The crystal structure of ophiobolin methoxybromide. Acta Cryst B24 1968; 1293-1303.
116. Anastasia M, Fiecchi A, Galli Kienle M, Scala A, Bolognesi M, Rossi G,. Proceedings of 11th IUPAC International Symposium on the Chemistry of Natural Products; 1978. p 108-111.
117. Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG, Taylor R. J Chem Soc Perkin Trans 2 1987; S1-S19.
118. Andolfi A, Evidente A, Santini A, Tuzi A,. Ophiobolin A. Acta Crystallograph Sect E Struct Rep 2006; 62: 2195-2197.
119. Evidente A, Punzo B, Andolfi A, Berestetskiy A, Motta A,. Alternethanoxins A and B, polycyclic ethanones produced by Alternaria sonchi, potential mycoherbicides for Sonchus arvensis biocontrol. J Agr Food Chem 2009; 57: 6656-6660.
120. Cimmino A, Andolfi A, Berestetskiy A, Evidente A,. Production of phytotoxins by Phoma exigua var. exigua, a potential mycoherbicide against perennial thistles. J Agr Food Chem 2008; 56: 6304-6309 (and references therein cited).
121. Evidente A, Cimmino A, Andolfi A, Berestetskiy A, Motta A,. Phomachalsins A-D, 26-ox[16] and [15]cytochalasans produced by Phoma exigua var. exigua, a potential mycoherbicide for Cirsium arvense biocontrol. Tetrahedron 2011; 67: 1557-1563.
122. Schneeweiss GM, Colwell A, Park JM, Jang CG, Stuessy TF,. Phylogeny of holoparasitic Orobanche (Orobanchaceae) inferred from nuclear ITS-sequences. Mol Phylogenet Evol 2004; 30: 465-478.
123. Joel DM, Hershenhorn Y, Eizenberg H, Aly R, Ejeta G, Rich PJ, Ranson JK, Sauerborn J, Rubiales D,. Biology and management of weedy root parasites. In:, Janik J, editor. Horticultural review. New York: Wiley; 2007. p 267-350 (and references therein cited).
124. Rubiales D, Sadiki M, Román B,. First report of Orobanche foetida on common vetch (Vicia sativa) in Morocco. Plant Dis 2005; 89: 528-528.
125. Yoneyama K, Awad AA, Xie X, Yoeyama K, Takeuchi Y,. Strigolactones as germination stimulants for root parasitic plants. Plant Cell Physiol 2010; 51: 1095-1103.
126. Evidente A, Fernández-Aparicio M, Cimmino A, Rubiales D, Andolfi A, Motta A,. Peagol and peagoldione, two new strigolactone like metabolites isolated from pea root exudates. Tetrahedron Lett 2009; 50: 6955-6958.
127. Johnson A, Rosebery G, Parker CA,. A novel approach to Striga and Orobanche control using synthetic germination stimulant. Weed Res 1976; 16: 223-227.
128. Dewick PM,. Medicinal natural products. Chichester: John Wiley & Sons Ltd; 1997. p 109-151.
129. Evidente A, Cimmino A, Fernández-Aparicio M, Andolfi A, Rubiales D, Motta A,. Polyphenols, including the new peapolyphenols A-C, from root exudates stimulate Orobanche foetida seed germination. J Agric Food Chem 2010; 58: 2902-2907.
130. Rafi MM, Vastano BC, Zhu N, Ho CT, Ghai G, Rosen RT, Galo MA, Di Paola RS,. Novel polyphenol molecule isolated from licorice root (Glycyrrhiza glabra) induces apoptosis, G2/M cell cycle arrest, and Bcl-2 phosphorylation in tumor cell lines. J Agric Food Chem 2002; 50: 677-684.
131. Lu F, Xu X,. Studies on flavonoids of Oxytropis falcata. Zhongguo Zhongyao Zazhi (China J Chin Mat Med) 2007; 32: 318-320. CAN 149:231825 AN 2008:34811.
132. Rubiales D, Fernández-Aparicio M, Pérez-de-Luque A, Prats E, Castillejo MA, Sillero J, Rispail N, Fondevilla S,. Breeding approaches for crenate broomrape (Orobanche crenata) management in pea (Pisum sativum). Pest Manag Sci 2009; 65: 553-559.
133. Osbourn AE, Lanzotti V,. Plant-derived natural products-Synthesis, function, and application. Dordrecht: Springer; 2009.
134. Evidente A, Capasso R, Motta A, Andolfi A, Vurro M, Zonno MC, Bottalico A,. Toxic metabolites from phytopathogenic Ascochyta species. Boll Chim Farm 1996; 135: 552-555.
135. Evidente A, Cimmino A, Fernandez-Aparicio M, Rubiales D, Andolfi A, Melck D,. Soyasapogenol B and trans-22-dehydrocampesterol from common vetch (Vicia sativa L.) root exudates stimulate broomrape seed germination. Pest Manag Sci 2011; 67: 1015-1022.
136. 1H-NMR spectra of soyasapogenol B. J Nat Prod 1990; 53: 298-302.
137. Giner JL, Zhao H, Beach DH, Parish ED, Jayasimhulu K, Kaneshiro ES,. Comprehensive and definitive structural identities of Pneumocystis carini sterols. J Lipid Res 2002; 43: 1114-1123 (and references therein cited).
138. Macias FA, Simonet AM, Galindo JCG,. Bioactive steroids and triterpenes from Melilotus messanensis and their allelopathic potential. J Chem Ecol 1997; 23: 1781-1803.
139. Ding PL, Hou AJ, Chen DF,. Three new isoprenylated flavonoids from the roots of Sophora flavescens. J Asia Nat Prod Res 2005; 7: 237-243.
140. Fernández-Aparicio M, Sillero JC, Rubiales D,. Resistance to broomrape species (Orobanche spp.) in common vetch (Vicia sativa L.). Crop Prot 2009; 28: 7-12.