Bioactive substances from insect pathogenic fungi

Accounts of Chemical Research

Volumn 38, Issue 10, 2005, Pages 813-823

  Isaka, Masahiko ^a   Kittakoop, Prasat ^a   Kirtikara, Kanyawim ^a   Hywel Jones, Nigel L ^a   Thebtaranonth, Yodhathai ^a  

^a NATIONAL SCIENCE AND TECHNOLOGY DEVELOPMENT AGENCY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ANTIPARASITIC AGENT; FUNGAL PROTEIN;

ANIMAL; ARTICLE; CHEMISTRY; DRUG INDUSTRY; FUNGUS; INSECT; METHODOLOGY; MICROBIOLOGY; THAILAND;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIPARASITIC AGENTS; CHEMISTRY, PHARMACEUTICAL; DRUG INDUSTRY; FUNGAL PROTEINS; FUNGI; INSECTS; THAILAND;

EID: 27644566697     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar040247r     Document Type: Article

References (68)

1. Hawksworth, D. L.; Rossman, A. Y. Where Are All the Undescribed Fungi. Phytopathology 1997, 87, 888-891.
2. Steinkraus, D. C.; Whitfield, J. B. Chinese Caterpillar Fungus and World Record Runners. Am. Entomol. 1994, 40, 235-239.
3. McCoy, C. W. Entomogenous Fungi as Microbial Pesticides. New Directions in Biological Control; Liss, A. R., Ed.; New York, 1990; pp 139-159.
4. Samson, R. A.; Evans, H. C.; Latge, J.-P. Atlas of Entomopathogenic Fungi; Springer: Heidelberg, Germany, 1988.
5. Hajek, A. E.; St Leger, R. J. Interactions Between Fungal Pathogens and Insect Hosts. Annu. Rev. Entomol. 1994, 39, 293-322.
6. Griesch, J.; Vilcinskas, A. Proteases Released by Entomopathogenic Fungi Impair Phagocytic Activity, Attachment and Spreading of Plasmatocytes Isolated from Haemolymph of the Greater Wax Moth Galleria mellonella. Biocontrol Sci. Technol. 1998, 8, 517-531.
7. Vey, A.; Matha, V.; Dumas, C. Effects of the Peptide Mycotoxin Destruxin E on Insect Haemocytes and on Dynamics and Efficiency of the Multicellular Immune Reaction. J. Invertebr. Pathol. 2002, 80, 177-187.
8. Hywel-Jones, N. L. The Importance of Invertebrate-Pathogenic Fungi from the Tropics. Trop. Mycol. 2002, 133-144.
9. Hywel-Jones, N. L. Cordyceps nutans and Its Anamorph a Pathogen of Hemipteran Bugs in Thailand. Mycol. Res. 1995, 99, 724-726.
10. Hywel-Jones, N. L. Cordyceps myrmecophila-Like Fungi Infecting Ants in the Leaf Litter of Tropical Forest in Thailand. Mycol. Res. 1996, 100, 613-619.
11. Evans, H. C.; Samson, R. A. Cordyceps Species and Their Anamorphs Pathogenic on Ants (Formicidae) in Tropical Forest Ecosystems. 2. The Camponotus (Formicinae) Complex. Trans. Br. Mycol. Soc. 1984, 82, 127-150.
12. Hywel-Jones, N. L. Cordyceps sphecocephala and a Hymenostilbe sp. Infecting Wasps and Bees in Thailand. Mycol. Res. 1995, 99, 154-158.
13. Mains, E. B. North American Entomogenous Species of Cordyceps. Mycologia 1958, 50, 169-222.
14. Hywel-Jones, N. L. The Relationship Between the Entomopathogenic Fungal Genera Cordyceps and Beauveria. Laimburg J. 2004, 1, 299-304.
15. Zhu, J.-S.; Halpern, G. M.; Jones, K. The Scientific Rediscovery of an Ancient Chinese Herbal Medicine: Cordyceps sinensis Part I. J. Altern. Complement. Med. 1998, 4, 289-303.
16. Zhu, J.-S.; Halpern, G. M.; Jones, K. The Scientific Rediscovery of an Ancient Chinese Herbal Medicine: Cordyceps sinensis Part II. J. Altern. Complement. Med. 1998, 4, 429-457.
17. Chen, Y. Q.; Hu, B.; Xu, F.; Zhang, W.; Zhou, H.; Qu, L. H. Genetic Variation of Cordyceps sinensis, a Fruit-Body-Producing Entomopathogenic Species from Different Geographical Regions in China. FEMS Microbiol. Lett. 2004, 230, 153-158.
18. Yamaguchi, Y.; Kagota, S.; Nakamura, K.; Shinozuka, K.; Kunitomo, M. Antioxidant Activity of the Extracts from Fruiting Bodies of Cultured Cordyceps sinensis. Phytother. Res. 2000, 14, 647-649.
19. Kuo, Y. C.; Tsai, W. J.; Wang, J. Y.; Chang, S. C.; Lin, C. Y.; Shiao, M. S. Regulation of Bronchoalveolar Lavage Fluids Cell Function by the Immunomodulatory Agents from Cordyceps sinensis. Life Sci. 2001, 68, 1067-1082.
20. Kiho, T.; Ookubo, K.; Usui, S.; Ukai, S.; Hirano, K. Structural Features and Hypoglycemic Activity of a Polysaccharide (CS-F10) from the Cultured Mycelium of Cordyceps sinensis. Biol. Pharm. Bull. 1999, 22, 966-970.
21. Chiou, W. F.; Chang, P. C.; Chou, C. J.; Chen, C. F. Protein Constituent Contributes to the Hypotensive and Vasorelaxant Activities of Codyceps sinensis. Life Sci. 2000, 66, 1369-1376.
22. Chen, Y. J.; Shiao, M. S.; Lee, S. S.; Wang, S. Y. Effect of Cordyceps sinensis on the Proliferation and Differentiation of Human Leukemic U937 Cells. Life Sci. 1997, 60, 2349-2359.
23. Bok, J. W.; Lermer, L.; Chilton, J.; Klingeman, H. G.; Towers, G. H. N. Antitumor Sterols from the Mycelia of Cordyceps sinensis. Phytochemistry 1999, 51, 891-898.
24. Kiho, T.; Tabata, H.; Ukai, S.; Hara, C. A Minor, Protein-Containing Galactomannan from a Sodium Carbonate Extract of Cordyceps sinensis. Carbohydr. Res. 1986, 156, 189-198.
25. Cross, B. E.; Edinberry, M. N.; Turner, W. B. Three Pyranonaphthazarin Pigments from Gnomonia erythrostoma. J. Chem. Soc. 1970, 209.
26. Cross, B. E.; Zammitt, L. J. Pigments of Gnomonia erythrostoma. Part II. Epierythrostominol and Epideoxyerythrostominol. J. Chem. Soc., Perkin Trans. 1 1973, 2975-2976.
27. Kittakoop, P.; Punya, J.; Kongsaeree, P.; Lertwerawat, Y.; Jintasirikul, A.; Tanticharoen, M.; Thebtaranonth, Y. Bioactive Naphthoquinones from Cordyceps unilateralis. Phytochemistry 1999, 52, 453-457.
28. Unakul, P.; Wongsa, P.; Kittakoop, P.; Intamas, S.; Srikitikulchai, P.; Tanticharoen, M. Production of Red Pigments by Insect Pathogenic Fungus Cordyceps unilateralis BCC 1869. J. Ind. Microbiol. Biotechnol. 2005, in press.
29. Isaka, M.; Tanticharoen, M.; Kongsaeree, P.; Thebtaranonth, Y. Structures of Cordypyridones A-D, Antimalarial N-Hydroxy- and N-Methoxy-2-pyridones from the Insect Pathogenic Fungus Cordyceps nipponica. J. Org. Chem. 2001, 66, 4803-4808.
30. Cai, P.; Smith, D.; Cunningham, B.; Brown-Shimer, S.; Katz, B.; Pearce, C.; Venables, D.; Houck, D. 8-Methyl-Pyridoxatin: A Novel N-Hydroxy Pyridone from Fungus OS-F61800 That Induces Erythropoietin in Human Cells. J. Nat. Prod. 1999, 62, 397-399.
31. Hywel-Jones, N. L. Cordyceps khaoyaiensis and C. pseudomilitaris, Two New Pathogens of Lepidopteran Larvae from Thailand. Mycol. Res. 1994, 98, 939-942.
32. Isaka, M.; Tanticharoen, M.; Thebtaranonth, Y. Cordyanhydrides A and B. Two Unique Anhydrides from the Insect Pathogenic Fungus Cordyceps pseudomilitaris BCC 1620. Tetrahedron Lett. 2000, 41, 1657-1660.
33. Jaturapat, A.; Isaka, M.; Hywel-Jones, N. L.; Lertwerawat, Y.; Kamchonwongpaisan, S.; Kirtikara, K.; Tanticharoen, M.; Thebtaranonth, Y. Bioxanthracenes from the Insect Pathogenic Fungus Cordyceps pseudomilitaris BCC1620. I. Taxonomy, Fermentation, Isolation, and Antimalarial Activity. J. Antibiot. 2001, 54, 29-35.
34. Isaka, M.; Kongsaeree, P.; Thebtaranonth, Y. Bioxanthracenes from the Insect Pathogenic Fungus Cordyceps pseudomilitaris BCC 1620. II. Structure Elucidation. J. Antibiot. 2001, 54, 36-43.
35. Toki, S.; Ando, K.; Yoshida, M.; Kawamoto, I.; Sano, H.; Matsuda, Y. ES-242-1, a Novel Compound from Verticillium sp., Binds to a Site on N-Methyl-D-aspartate Receptor That Is Coupled to the Channel Domain. J. Antibiot. 1992, 45, 88-93.
36. Toki, S.; Ando, K.; Kawamoto, I.; Sano, H.; Yoshida, M.; Matsuda, Y. ES-242-2, 3, 4, 5, 6, 7, and 8, Novel Bioxanthracenes Produced by Verticillium sp., Which Act on the N-Methyl-D-Aspatate Receptor. J. Antibiot. 1992, 45, 1047-1054.
37. Tatsuta, K.; Yamazaki, T.; Mase, T.; Yoshimoto, T. The First Total Synthesis of a Bioxanthracene (-)-ES-242-4, an N-Methyl-D-aspartate Receptor Antagonist. Tetrahedron Lett. 1998, 39, 1771-1772.
38. Tatsuta, K.; Nagai, T.; Mase, T.; Yamazaki, T.; Tamura, T. Synthesis of an N-Methyl-D-aspartate Receptor Antagonist, ES-242-5, and its Analogs. J. Antibiot. 1999, 52, 422-425.
39. Tatsuta, K.; Nagai, T.; Mase, T.; Tamura, T.; Nakamura, H. Absolute and Atropisomeric Structure of ES-242s, N-Methyl-D-aspartate Receptor Antagonists. J. Antibiot. 1999, 52, 433-436.
40. Seephonkai, P.; Isaka, M.; Kittakoop, P.; Trakulnaleamsai, S.; Rattanajak, R.; Tanticharoen, M.; Thebtaranonth, Y. A New Tropolone from the Insect Pathogenic Fungus Cordycep sp. BCC 1681. J. Antibiot. 2001, 54, 751-752.
41. Kikuchi, H.; Takahashi, N.; Oshima, Y. Novel Aromatics Bearing 4-Methylglucose Unit Isolated from the Oriental Crude Drug Bombyx Batryticatus. Tetrahedron Lett. 2004, 45, 367-370.
42. Suzuki, A.; Kanaoka, M.; Isogai, A.; Murakoshi, S.; Ichinoe, M.; Tamura, S. Bassianolide, a New Insecticidal Cyclodepsipeptide from Beauveria bassiana and Verticillium lecanii. Tetrahedron Lett. 1977, 18, 2167-2170.
43. Namatame, I.; Tomoda, H.; Ishibashi, S.; Omura, S. Antiatherogenic Activity of Fungal Beauveriolides, Inhibitors of Lipid Droplet Accumulation in Macrophages. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 737-742.
44. Kikuchi, H.; Miyagawa, Y.; Nakamura, K.; Sahashi, Y.; Inatomi, S.; Oshima, Y. A Novel Carbon Skeletal Trichothecane, Tenuipesine A, Isolated from an Entomopathogenic Fungus, Paecilomyces tenuipes. Org. Lett. 2004, 6, 4531-4533.
45. Kikuchi, H.; Miyagawa, Y.; Sahashi, Y.; Inatomi, S.; Haganuma, A.; Nakahata, N.; Oshima, Y. Novel Spirocyclic Trichothecanes, Spirotenuipesine A and B, Isolated from Entomopathogenic Fungus, Paecilomyces tenuipes. J. Org. Chem. 2004, 69, 352-356.
46. Nilanonta, C.; Isaka, M.; Kittakoop, P.; Palittapongarnpim, P.; Kamchonwongpaisan, S.; Pittayakhajonwut, D.; Tanticharoen, M.; Thebtaranonth, Y. Antimycobacterial and Antiplasmodial Cyclodepsipeptides from the Insect Pathogenic Fungus Paecilomyces tenuipes BCC1614. Planta Med. 2000, 66, 756-758.
47. Hamil, R. L.; Higgens, C. E.; Boaz, H. E.; Gorman, M. The Structure of Beauvericin, a New Depsipeptide Antibiotic Toxic to Artemia salina. Tetrahedron Lett. 1969, 4255-4258.
48. Gupta, S.; Montllor, C.; Hwang, Y.-S. Isolation of Novel Beauvericin Analogues from the Fungus Beauveria bassiana. J. Nat. Prod. 1995, 58, 733-738.
49. Peeters, H.; Zocher, R.; Madry, N.; Kleinkauf, H. Incorporation of Radioactive Precursors into Beauvericin Produced by Paecilomyces fumoso-roseus. Phytochemistry 1983, 22, 1719-1720.
50. Peeters, H.; Zocher, R.; Madry, N.; Oelrichs, P. B.; Kleinkauf, H.; Kraepelin, G. Cell-free Synthesis of the Depsipeptide Beauvericin. J. Antibiot. 1983, 36, 1762-1766.
51. Nilanonta, C.; Isaka, M.; Kittakoop, P.; Trakulnaleamsai, S.; Tanticharoen, M.; Thebtaranonth, Y. Precursor-Directed Biosynthesis of Beauvericin Analogs by the Insect Pathogenic Fungus Paecilomyces tenuipes BCC 1614. Tetrahedron 2002, 58, 3355-3360.
52. Nilanonta, C.; Isaka, M.; Chanphen, R.; Thong-orn, N.; Tanticharoen, M.; Thebtaranonth, Y. Unusual Enniatins Produced by the Insect Pathogenic Fungus Verticillium hemipterigenum: Isolation and Studies on Precursor-directed Biosynthesis. Tetrahedron 2003, 59, 1015-1020.
53. Mikawa, T.; Chiba, N.; Ogishi, H.; Gomi, S.; Miyaji, S.; Sezaki, M. Jpn. Kokai Tokyo Koho 1991, JP 02229177-A2; Chem. Abstr. 1991, 114, 22748k.
54. Supothina, S.; Isaka, M.; Kirtikara, K.; Tanticharoen, M.; Thebtaranonth, Y. Enniatin Production by the Entomopathogenic Fungus Verticillium hemipterigenum BCC 1449. J. Antibiot. 2004, 57, 732-738.
55. 2, and N: Novel Hydroxy Analogs. Helv. Chim. Acta 2004, 87, 2066-2073.
56. Nilanonta, C.; Isaka, M.; Kittakoop, P.; Saenboonrueng, J.; Rukachaisirikul, V.; Kongsaeree, P.; Thebtaranonth, Y. New Diketopiperazines from the Entomopathogenic Fungus Verticillium hemipterigenum BCC 1449. J. Antibiot. 2003, 56, 647-651.
57. Isaka, M.; Palasarn, S.; Rachtawee, P.; Vimuttipong, S.; Kongsaeree, P. Unique Diketopiperazine Dimers from the Insect Pathogenic Fungus Verticillium hemipterigenum BCC 1449. Org. Lett. 2005, 7, 2257-2260.
58. Seephonkai, P.; Isaka, M.; Kittakoop, P.; Boonudomlap, U.; Thebtaranonth, Y. A Novel Ascochlorin Glycoside from the Insect Pathogenic Fungus Verticillium hemipterigenum BCC 2370. J. Antibiot. 2004, 57, 10-16.
59. Vongvanich, N.; Kittakoop, P.; Isaka, M.; Trakulnaleamsai, S.; Vimuttipong, S.; Tanticharoen, M.; Thebtaranonth, Y. Hirsutellide A, a New Antimycobacterial Cyclohexadepsipeptide from the Entomopathogenic Fungus Hirsutella kobayasii. J. Nat. Prod. 2002, 65, 1346-1348.
60. Isaka, M.; Rugseree, N.; Maithip, P.; Kongsaeree, P.; Prabpai, S.; Thebtaranonth, Y. Hirsutellones A-E, Antimycobacterial Alkaloids from the Insect Pathogenic Fungus Hirsutella nivea BCC2594. Tetrahedron Lett. 2005, 61, 5577-5583.
61. Hasegawa, A.; Koizumi, F.; Takahashi, Y.; Ando, K.; Ogawa, T.; Hara, M.; Yoshida, M. 43rd Symposium on the Chemistry of Natural Products, Symposium Papers; Osaka, Japan, 2001; pp 467-472.
62. He, H.; Yang, H. Y.; Bigelis, R.; Solum, E. H.; Greenstein, M.; Carter, G. T. Pyrrocidines A and B, New Antibiotics Produced by a Filamentous Fungus. Tetrahedron Lett. 2002, 43, 1633-1636.
63. Boonphong, S.; Kittakoop, P.; Isaka, M.; Palittapongarnpim, P.; Jaturapat, A.; Danwisetkanjana, K.; Tanticharoen, M.; Thebtaranonth, Y. A New Antimycobacterial; 3β-Acetoxy-15α,22-dihydroxyhopane, from the Insect Pathogenic Fungus Aschersonia tubulata. Planta Med. 2001, 67, 279-281.
64. Watts, P.; Kittakoop, P.; Veeranondha, S.; Wanasith, S.; Thongwichian, R.; Saisaha, P.; Intamas, S.; Hywel-Jones, N. L. Cytotoxicity Against Insect Cells of Entomopathogenic Fungi of the Genera Hypocrella (Anamorph Aschersonia): Possible Agents for Biological Control. Mycol. Res. 2003, 107, 581-586.
65. Sakurai, N.; Akatsuka, H.; Mizukami, J.; Nishio, M.; Kono, J. RANKL (Receptor Activator of NF-κB Ligand) Antagonists Manufacture with Ceuthospora, JP2004075625.
66. Desjardins, R. E.; Canfield, C. J.; Haynes, J. D.; Chulay, J. D. Quantitative Assessment of Antimalaria Activity in Vitro by a Semiautomated Microdilution Technique. Antimicrob. Agents Chemother. 1979, 16, 710-718.
67. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenny, S.; Boyd, M. R. New Colorimetric Cytotoxicity Assay for Anti-cancer Drug Screening. J. Natl. Cancer Inst. 1990, 82, 1107-1112.
68. Collins, L.; Franzblau, S. G. Microplate Alamar Blue Assay Versus BACTEC 460 System for High-Throughput Screening of Compounds Against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob. Agents Chemother. 1997, 41, 1004-1009.