The destruxins: Synthesis, biosynthesis, biotransformation, and biological activity

Phytochemistry

Volumn 59, Issue 6, 2002, Pages 579-596

  Pedras, M Soledade C ^a   Irina Zaharia, L I ^a   Ward, Dale E ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; CYCLOPEPTIDE; DEPSIPEPTIDE; DESTRUXIN A; DESTRUXIN B; ENZYME INHIBITOR; HERBICIDE; INSECTICIDE; 2 HYDROXYACID; AMINO ACID; DESTRUXIN; DESTRUXIN DERIVATIVE; UNCLASSIFIED DRUG; VIRULENCE FACTOR;

ANIMAL; BIOSYNTHESIS; BIOTRANSFORMATION; CHEMISTRY; FUNGUS; HUMAN; METABOLISM; REVIEW; SYNTHESIS; AMINO ACID ANALYSIS; CHEMICAL STRUCTURE; DRUG ACTIVITY; EPIDEMIC; FUNGUS ISOLATION; INSECT CONTROL; INSECTICIDAL ACTIVITY; ISOLATION PROCEDURE; METABOLITE; METHYLATION; NONHUMAN; OOSPORA DESTRUCTOR; OOSPORE; PEPTIDE SYNTHESIS; PHYTOCHEMISTRY; PHYTOTOXICITY; PROTEIN STRUCTURE; SPECIES IDENTIFICATION; VIRULENCE;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; BIOTRANSFORMATION; DEPSIPEPTIDES; ENZYME INHIBITORS; FUNGI; HERBICIDES; HUMANS; INSECTICIDES; PEPTIDES, CYCLIC;

FUNGI; INSECTA; OOSPORA;

EID: 0037086124     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(02)00016-X     Document Type: Review

References (107)

1. Ultrastructural changes in Brassica leaves caused by Alternaria brassicae and destruxin B
2. Antifeedant properties of destruxins and their potential use with the entomogenous fungus Metarrhizium anisopliae for improved control of crucifer pests
3. Synthesis and biological evaluation of destruxin A and related analogues
4. Metabolites produced by Alternaria brassicae, the black spot pathogen of canola. Part 1. The phytotoxic components
5. Cloning and sequence analysis of an intron-containing domain from a peptide synthase-encoding gene of the entomopathogenic fungus Metarrhizium anisopliae
6. Purification, chemical characterization and host-specificity of the toxin produced by Alternaria brassicae
7. A note on phytotoxicity of homodestruxin B, a compound produced by Alternaria brassicae
8. Effects of efrapeptin and destruxin, metabolites of entomogenous fungi, on the hydrolytic activity of a vacuolar type ATPase identified on the brush border membrane vesicles of Galleria mellonella midgut and on plant membrane bound hydrolytic enzymes
9. Susceptibility of spruce budworm. Choristoneura fumiferana clemens, to destruxins, cyclodepsipeptidic mycotoxins of Metarrhizium anisopliae
10. Phytotoxicity of destruxin B and its possible role in the pathogenesis of Alternaria brassicae
11. HPLC purification of destruxins produced by Alternaria brassicae in culture and leaves of Brassica napus
12. Destruxin-A4 chlorohydrin, a novel destruxin from fungus OS-F68576: Isolation, structure determination, and biological activity as an inducer of erythropoietin
13. Synthesis and biological activity of a destruxin analogue: D-Lac-6 destruxin E
14. Destruxin analogues: Depsi peptidic bond replacement by amide bond
15. Destruxin analogs: Variations of the α-hydroxy acid side chain
16. Natural cyclopeptides as leads for novel pesticides: Tentoxin and destruxin
17. Pseudodestruxins A and B: New cyclic depsipeptides from the Coprophilous fungus Nigrosabulum globosum
18. The novel desmethyldestruxin B, from Metarrhizium anisopliae, that suppresses hepatitis B virus surface antigen production in human hepatoma cells
19. Suppressive effects of destruxin B on hepatitis B virus surface antigen gene expression in human hepatoma cells
20. Purification and quantification of destruxins A and B from Metarrhizium anisopliae
21. Direct in vitro and in vivo monitoring of destruxins metabolism in insects using internal surface reversed-phase high-performance liquid chromatography. I. Behaviour of E destruxin in locusts
22. Direct injection onto the HPLC column for monitoring the behaviour of xenobiotics in biological media. II. Behaviour of cymoxanil in fungus and locust and of E-destruxin in locust
23. Activity of natural toxins against the silverleaf white fly, Bemisia argentifolii, using a novel feeding bioassay system
24. Insecticidal and cytotoxic effects of natural and hemisynthetic destruxins
25. Effects of destruxins, cyclic depsipeptide mycotoxins, on calcium balance and phosphorylation of intracellular proteins in lepidopteran cell lines
26. Comparative study of the cytological aspects of the mode of action of destruxins and other peptidic fungal metabolites on target epithelial cells
27. Purification and characterization of roseotoxin B, a toxic cyclodepsipeptide from Trichothecium roseum
28. Effect of destruxins A, B, and E on the pathogenesis of Metarrhizium anisopliae in larvae of the Coleoptera scarabaeidae
29. Relative toxicity of destruxin E to the lepidopteran Galleria mellonella larvae
30. Toxicity and pathogenicity testing of the insect pest control fungus Metarrhizium anisopliae
31. The use of entomogenous fungi for pest control and the role of toxins in pathogenesis
32. Insecticidal cyclodepsipeptides from Metarrhizium anisopliae
33. Preparative isolation of destruxins from Metarrhizium anisopliae by high performance liquid chromatography
34. Molecular conformation of destruxin A
35. Studies of host specificity and potential use for in vitro selection of destruxin B from Alternaria brassicae Berk. (Sacc)
36. Determination of destruxins, cyclic peptide toxins, produced by different strains of Metarhizium anisopliae and their mutants induced by ethyl methane sulfonate and ultraviolet using HPLC method
37. Metabolites of A and E destruxins in Galleria mellonella larvae using negative-ion fast-atom bombardment mass spectrometry
38. Behaviour of diastereoisomers of synthetic analogues of destruxin using high performance liquid chromatography and fast-atom bombardment mass spectrometry
39. Chemical synthesis of natural product peptides: Coupling methods for the incorporation of noncoded amino acids into peptides
40. Inhibitory effects of cyclodepsipeptides, destruxins, from the fungus Metarrhizium anisopliae, on cellular immunity in insects
41. Dihydrodestruxin A: A natural destruxin from Metarrhizium anisopliae
42. Detoxification of destruxins in Galleria mellonella L. larvae
43. Biosynthesis of destruxins
44. I a cyclopeptide from the fungus Metarrhizium anisopliae
45. Rapid screening of destruxins by liquid chromatography-mass spectrometry
46. The production of destruxins by the entomogenous fungus Metarrhizium anisopliae var. major
47. Isolation and characterization of two novel nematicidal depsipeptides from an imperfect fungus, strain D1084
48. The role of destruxins in the pathogenicity of Metarrhizium anisopliae for three species of insect
49. Toxic substances to insects, produced by Aspergillus ochraceus and Oospora destructor
50. Studies on the new toxic substances to insects, destruxin A and B, produced by Oospora destructor
51. New destruxins from the entomopathogenic fungus Aschersonia sp
52. Total synthesis of destruxin B
53. Sequencing of cyclodepsipeptides (destruxins) and biological behaviour using HPLC and FAB-desorptiontandem MS
54. Direct determination of the sequence of destruxins (cyclodepsipeptides) using negative-ion fast-atom bombardment mass spectrometry
55. Desorption of ions from locust tissues. I. Behaviour of E-destruxin using positive-ion fast atom bombardment mass spectrometry
56. Sequencing of cyclodepsipeptides (destruxins) using positive fast atom bombardment desorption tandem mass spectrometry
57. Desorption of ions from locust tissues. II. Metabolites of E-destruxin using negative-ion fast atom bombardment mass spectrometry
58. Synthesis of a cyclohexadepsipeptide, protodestruxin
59. Cyclic peptides. II. Synthesis of a cyclodepsipeptide, Protodestruxin
60. Non-extractive metabolism study of E and A destruxins in the locust, Locusta migratoria L. III. Direct high-performance liquid chromatographic analysis and parallel fast atom bombardment mass spectrometric monitoring
61. Gas-phase reactivity of protonated cyclodepsipeptidic toxins: The study of a systematic fragmentation pathway under fast-atom bombardment desorption
62. Desorption of ions from locust tissues. III. Study of a metabolite of A-destruxin using fast-atom bombardment linked-scan mass spectrometry
63. Studies on the dynamics of the production of destruxins by Metarrhizium anisopliae. Direct high-performance liquid chromatographic and fast atom bombardment mass spectrometric analysis correlated with biological activity tests
64. Cytotoxicity of cyclodepsipeptides on murine lymphocytes and on L 1210 leukemia cells
65. +-translocating ATPase
66. Conformational studies of destruxins, insecticidal cyclodepsipeptides
67. Cytometric study of the effects of destruxin E on mouse leukemia cells
68. In vitro effect of fungal cyclodepsipeptides on leukemic cells: Study of destruxins A, B and E
69. Depsipeptides from Metarrhizium anisopliae
70. Sinalexin, a phytoalexin from white mustard elicited by destruxin B and Alternaria brassicae
71. Metabolism of the host-selective toxins destruxin B and homodestruxin B: Probing a plant disease resistance trait
72. Vital staining of plant cell suspension cultures: Evaluation of the phytotoxic activity of the phytotoxins phomalide and destruxin B
73. Comparison of the phytotoxic activity of the phytotoxin destruxin B and four natural analogs
74. In planta sequential hydroxylation and glycosylation of a fungal phytotoxin: Avoiding cell death and overcoming the fungal invader
75. Susceptibility of the onion maggot, Delia antiqua (Diptera: Anthomyiidae) to the mycotoxin destruxin E
76. Contact toxicity of the mycotoxin destruxin E to Empoasca vitis (Göthe) (Hom., Cicadellidae)
77. Liquid chromatography-electrospray time-of-flight mass spectrometry for on-line accurate mass determination and identification of cyclodepsipeptides in a crude extract of the fungus Metarrhizium anisopliae
78. Antiviral activity of a mycotoxin. Study of the toxin of the hyphomycete Metarrhizium anisopliae (Metsch) Sorok in cell culture
79. Effects of mycotoxins on invertebrate cells in vitro
80. NMR studies of the conformation of destruxin A in water and in acetonitrile
81. Relative oral toxicity of destruxins A, B and E to Musca domestica larvae
82. Toxic and repulsive effects of spray, 'per os' and systemic applications of destruxin E to aphids
83. Toxins from the entomogenous fungus Metarrhizium anisopliae. 2) Symptoms and detection in moribund hosts
84. Application of reversed-phase HPLC in separation and detection of the cyclodepsipeptide toxins produced by the entomopathogenic fungus Metarrhizium anisopliae
85. The role of destruxins in the pathogenicity of 3 strains of Metarrhizium anisopliae for the tobacco hornworm Manduca Sexta
86. Calcium channel activation of insect muscle by destruxins, insecticidal compounds produced by the entomopathogenic fungus Metarrhiziumium anisopliae
87. Pollen selection for Alternaria resistance in oilseed brassicas: Responses of pollen grains and leaves to a toxin of A. brassicae
88. Structure and conformation of roseotoxin B
89. Crystal and molecular structure of destruxin B
90. Suppressive effects of metabolites from Alternaria brassicae on the hepatitis B surface antigen
91. Structural elucidation of destruxin A
92. Isolation and structure elucidation of three new insecticidal cyclodepsipeptides, destruxins C and D and desmethyldestruxin B, produced by Metarrhizium anisopliae
93. Detection of destruxins in silkworm larvae infected with Metarrhizium anisopliae
94. Isolation and structure of protodestruxin from Metarrhizium anisopliae
95. The structure of destruxin B, a toxic metabolite of Oospora destructor
96. Phytotoxins produced by Alternaria brassicae and bioassay of destruxin B
97. +-ATPase inhibitors on CTL-mediated cytotoxicity
98. Roseocardin, a novel cardiotonic cyclodepsipeptide from Trichothecium roseum TT103
99. Non-cyclic AMP-dependent, positive inotropic cyclodepsipeptides with negative chronotropy
100. Metabolites of Ophiosphaerella herpotricha, a cause of spring dead spot of bermuda grass
101. Immunodepressive effect of fungal toxins: Inhibition of the reaction of multicellular encapsulation by the destruxins
102. Mechanisms of insecticidal activity of a mycotoxin, destruxin E, on dipteran pathogen vectors and disseminators
103. New destruxins from the entomopathogenic fungus Metarrhizium anisopliae
104. Probing host-selective phytotoxicity: Synthesis of natural analogs of the host-selective toxin destruxin B
105. Synthesis of the host-selective phytotoxin destruxin B. Avoiding diketopiperazine formation from an N-methyl amino acid dipeptide by use of the Bochydrazide derivative
106. Study of structure-activity correlation in destruxins, a class of cyclodepsipeptides possessing suppressive effect on the genyeration of hepatitis B virus surface antigen in human hepatoma cells