메뉴 건너뛰기




Volumn 54, Issue 8, 2006, Pages 2921-2925

Insecticidal activity of paraherquamides, including paraherquamide H and paraherquamide I, two new alkaloids isolated from Penicillium cluniae

Author keywords

Brevianamides; Diketopiperazines; Insecticide activity; Marcfortines; Oncopeltus fasciatus; Paraherquamide H; Paraherquamide I; Paraherquamides; Penicillium cluniae

Indexed keywords

INDOLIZINE DERIVATIVE; INSECTICIDE; PARAHERQUAMIDE; SPIRO COMPOUND; VM 55596;

EID: 33646508518     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0530998     Document Type: Article
Times cited : (41)

References (34)
  • 1
    • 0019352244 scopus 로고
    • The structure of paraherquamide, a toxic metabolite from Penicillium paraherquei
    • Yamazaki, M.; Okuyama, E. The structure of paraherquamide, a toxic metabolite from Penicillium paraherquei. Tetrahedron Lett. 1981, 22, 135-136.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 135-136
    • Yamazaki, M.1    Okuyama, E.2
  • 2
    • 0025146733 scopus 로고
    • Novel antinematodal and antiparasitic agents from Penicillium charlesii. I. Fermentation, isolation and biological activity
    • Ondeyka, J. G.; Goegelman, R. T.; Schaeffer, J. M.; Kelemen, L.; Zitano, L. Novel antinematodal and antiparasitic agents from Penicillium charlesii. I. Fermentation, isolation and biological activity. J. Antibiot. 1990, 43, 1375-1379.
    • (1990) J. Antibiot. , vol.43 , pp. 1375-1379
    • Ondeyka, J.G.1    Goegelman, R.T.2    Schaeffer, J.M.3    Kelemen, L.4    Zitano, L.5
  • 3
    • 0025010854 scopus 로고
    • Novel antinematodal and antiparasitic agents from Penicillium charlesii. II. Structure determination of paraherquamides B, C, D, E, F, and G
    • Liesch, J. M.; Wichmann, C. F. Novel antinematodal and antiparasitic agents from Penicillium charlesii. II. Structure determination of paraherquamides B, C, D, E, F, and G. J. Antibiot. 1990, 43, 1380-1386.
    • (1990) J. Antibiot. , vol.43 , pp. 1380-1386
    • Liesch, J.M.1    Wichmann, C.F.2
  • 5
    • 0029880010 scopus 로고    scopus 로고
    • Metabolites from an Antarctic sponge-associated bacterium, Pseudomonas aeruginosa
    • Jayatilake, G. S.; Thornton, M. P.; Leonard, A. C.; Grimwade, J. E.; Baker, B. J. Metabolites from an Antarctic sponge-associated bacterium, Pseudomonas aeruginosa. J. Nat. Prod. 1996, 59, 293-296.
    • (1996) J. Nat. Prod. , vol.59 , pp. 293-296
    • Jayatilake, G.S.1    Thornton, M.P.2    Leonard, A.C.3    Grimwade, J.E.4    Baker, B.J.5
  • 8
    • 0015861423 scopus 로고
    • Production, isolation, and preliminary toxicity studies of brevianamide A from cultures of Penicillium viridicatum
    • Wilson, B. J.; Yang, D. T. C.; Harris, T. M. Production, isolation, and preliminary toxicity studies of brevianamide A from cultures of Penicillium viridicatum. Appl. Microbiol. 1973, 26, 633-635.
    • (1973) Appl. Microbiol. , vol.26 , pp. 633-635
    • Wilson, B.J.1    Yang, D.T.C.2    Harris, T.M.3
  • 9
    • 0000775710 scopus 로고
    • Studies in relation to biosynthesis - XLIV. Structural elucidations of brevianamides-B, -C, -D and -F
    • Birch, A. J.; Russell, R. A. Studies in relation to biosynthesis - XLIV. Structural elucidations of brevianamides-B, -C, -D and -F. Tetrahedron 1972, 28, 2999-3008.
    • (1972) Tetrahedron , vol.28 , pp. 2999-3008
    • Birch, A.J.1    Russell, R.A.2
  • 10
    • 37049093393 scopus 로고
    • Isolation and Structure (X-ray analysis) of marcfortine A, a new alkaloid from Penicillium roqueforti
    • Polonsky, J.; Merrien M.-A.; Prangé, T.; Pascard, C.; Moreau, S. Isolation and Structure (X-ray analysis) of marcfortine A, a new alkaloid from Penicillium roqueforti. J. Chem. Soc. Chem. Comm. 1980, 601-602.
    • (1980) J. Chem. Soc. Chem. Comm. , pp. 601-602
    • Polonsky, J.1    Merrien, M.-A.2    Prangé, T.3    Pascard, C.4    Moreau, S.5
  • 12
    • 0029856862 scopus 로고    scopus 로고
    • Sclerotiamide: A new member of the paraherquamide class with potent antiinsectan activity from the sclerotia of Aspergillus sclerotiorum
    • Whyte, A. C.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. Sclerotiamide: A new member of the paraherquamide class with potent antiinsectan activity from the sclerotia of Aspergillus sclerotiorum. J. Nat. Prod. 1996, 59, 1093-1095.
    • (1996) J. Nat. Prod. , vol.59 , pp. 1093-1095
    • Whyte, A.C.1    Gloer, J.B.2    Wicklow, D.T.3    Dowd, P.F.4
  • 13
    • 0030806639 scopus 로고    scopus 로고
    • Novel anthelmintic metabolites from an Aspergillus species; the aspergillimides
    • Banks, R. M.; Blanchflower, S. E.; Everett J. R.; Manger, B. R.; Reading, C. Novel anthelmintic metabolites from an Aspergillus species; the aspergillimides. J. Antibiot. 1997, 50, 840-846.
    • (1997) J. Antibiot. , vol.50 , pp. 840-846
    • Banks, R.M.1    Blanchflower, S.E.2    Everett, J.R.3    Manger, B.R.4    Reading, C.5
  • 14
    • 0030761748 scopus 로고    scopus 로고
    • Asperparaline A, a new paralytic alkaloid from Aspergillus japonicus JV-23
    • Hayashi, H.; Nishimoto, U.; Nozaki, H. Asperparaline A, a new paralytic alkaloid from Aspergillus japonicus JV-23. Tetrahedron Lett. 1997, 38, 5655-5658.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 5655-5658
    • Hayashi, H.1    Nishimoto, U.2    Nozaki, H.3
  • 15
    • 0033630154 scopus 로고    scopus 로고
    • New paralytic alkaloids, asperparalines A, B, and C, from Aspergillus japonicus JV-23
    • Hayashi, H.; Nishimoto, U.; Akiyama, K.; Nozaki, H. New paralytic alkaloids, asperparalines A, B, and C, from Aspergillus japonicus JV-23. Biosci., Biotechnol., Biochem. 2000, 64, 111-115.
    • (2000) Biosci., Biotechnol., Biochem. , vol.64 , pp. 111-115
    • Hayashi, H.1    Nishimoto, U.2    Akiyama, K.3    Nozaki, H.4
  • 16
    • 33646533555 scopus 로고    scopus 로고
    • Avrainvillamide, a cytotoxic marine natural product, and the derivatives. U.S. Patent 6,066,635, 2000
    • Fenical, W.; Jensel, P. R.; Cheng, X. C. Avrainvillamide, a cytotoxic marine natural product, and the derivatives. U.S. Patent 6,066,635, 2000.
    • Fenical, W.1    Jensel, P.R.2    Cheng, X.C.3
  • 17
    • 33646528877 scopus 로고    scopus 로고
    • Derivatives of paraherquamide isolated from a fermentation broth active as antiparasitic agents. U.S. Patent 4,873,247, Oct. 10, 1989
    • Goegeman, R.; Ondeyka, J. Derivatives of paraherquamide isolated from a fermentation broth active as antiparasitic agents. U.S. Patent 4,873,247, Oct. 10, 1989.
    • Goegeman, R.1    Ondeyka, J.2
  • 19
    • 33646514858 scopus 로고    scopus 로고
    • Paraherquamide derivatives, precursor thereof, processes for their preparation, microorganism used and their use as antiparasitic agents. Patent WO 92/22555, 1992
    • Banks, R. M.; Blanchflower, S. E.; Reading, C. Paraherquamide derivatives, precursor thereof, processes for their preparation, microorganism used and their use as antiparasitic agents. Patent WO 92/22555, 1992.
    • Banks, R.M.1    Blanchflower, S.E.2    Reading, C.3
  • 20
    • 33646520106 scopus 로고    scopus 로고
    • Marcfortine/paraherquamide derivatives useful as antiparasitic agents. Patent WO 93/10120, 1993
    • Lee, B. H.; Taylor, R. N.; Whaley, H. A.; Nelson, S. J.; Marshall, V. P. Marcfortine/paraherquamide derivatives useful as antiparasitic agents. Patent WO 93/10120, 1993.
    • Lee, B.H.1    Taylor, R.N.2    Whaley, H.A.3    Nelson, S.J.4    Marshall, V.P.5
  • 21
    • 33646496355 scopus 로고    scopus 로고
    • Antiparasitic marcfortines and paraherquamides. U.S. Patent 5,703,078, 1997
    • Lee, B. H.; Clothier, M. F. Antiparasitic marcfortines and paraherquamides. U.S. Patent 5,703,078, 1997.
    • Lee, B.H.1    Clothier, M.F.2
  • 22
    • 0030020574 scopus 로고    scopus 로고
    • Stereo-controlled total synthesis of (+)-paraherquamide B
    • Cushing, T. D.; Sanz-Cervera, J. F.; Williams, R. M. Stereo-controlled total synthesis of (+)-paraherquamide B. J. Am. Chem. Soc. 1996, 118, 557-579.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 557-579
    • Cushing, T.D.1    Sanz-Cervera, J.F.2    Williams, R.M.3
  • 23
    • 0034679469 scopus 로고    scopus 로고
    • Asymmetric, stereo-controlled total synthesis of paraherquamide A
    • Williams, R. M.; Cao, J.; Tsujishima, H. Asymmetric, stereo-controlled total synthesis of paraherquamide A. Angew. Chem. Int. Ed. 2000, 39, 2540-2544.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 2540-2544
    • Williams, R.M.1    Cao, J.2    Tsujishima, H.3
  • 24
    • 0034830338 scopus 로고    scopus 로고
    • Studies on the biosynthesis of paraherquamide: Concerning the mechanism of the oxidative cyclization of L-isoleucine to β-methylproline
    • Stocking, E. M.; Martinez, R. A.; Silks, L. A.; Sanz-Cervera, J. F.; Williams, R. M. Studies on the biosynthesis of paraherquamide: Concerning the mechanism of the oxidative cyclization of L-isoleucine to β-methylproline. J. Am. Chem. Soc. 2001, 123, 3391-3392.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3391-3392
    • Stocking, E.M.1    Martinez, R.A.2    Silks, L.A.3    Sanz-Cervera, J.F.4    Williams, R.M.5
  • 25
    • 0037139572 scopus 로고    scopus 로고
    • Asymmetric total synthesis of (-)-VM55599: Establishment of the absolute steroechemistry and biogenetic implications
    • Sanz-Cervera, J. F.; Williams, R. M. Asymmetric total synthesis of (-)-VM55599: Establishment of the absolute steroechemistry and biogenetic implications. J. Am. Chem. Soc. 2002, 124, 2556-2559.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 2556-2559
    • Sanz-Cervera, J.F.1    Williams, R.M.2
  • 27
    • 0037326264 scopus 로고    scopus 로고
    • Paraherquamides, brevianamides, and asperparalines: Laboratory synthesis and biosynthesis. An interim report
    • Williams, R. M.; Cox, R. J. Paraherquamides, brevianamides, and asperparalines: Laboratory synthesis and biosynthesis. An interim report. Acc. Chem. Res. 2003, 36, 127-139.
    • (2003) Acc. Chem. Res. , vol.36 , pp. 127-139
    • Williams, R.M.1    Cox, R.J.2
  • 28
    • 2342464084 scopus 로고    scopus 로고
    • Concise synthesis of the core bicyclo[2,2,2]diazaoctane ring common to asperparaline, paraherquamide, and stephacidin alkaloids
    • Adams, L. A.; Gray, C. R.; Williams, R. M. Concise synthesis of the core bicyclo[2,2,2]diazaoctane ring common to asperparaline, paraherquamide, and stephacidin alkaloids. Tetrahedron Lett. 2004, 45, 4489-4493.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 4489-4493
    • Adams, L.A.1    Gray, C.R.2    Williams, R.M.3
  • 29
    • 0006557573 scopus 로고
    • Oncopeltus fasciatus: A research animal
    • Feir, D., Oncopeltus fasciatus: A research animal. Annu. Rev. Entomol. 1974, 19, 81-96.
    • (1974) Annu. Rev. Entomol. , vol.19 , pp. 81-96
    • Feir, D.1
  • 30
    • 0004116672 scopus 로고    scopus 로고
    • Cambridge University Press: Cambridge, U.K.
    • Finney, D. J. Probit Analysis; Cambridge University Press: Cambridge, U.K.
    • Probit Analysis
    • Finney, D.J.1
  • 31
    • 0041125709 scopus 로고
    • Chemical modification of paraherquamide. 1. Unusual reactions and absolute sterochemistry
    • Blizzard, T. A.; Marino, G.; Mrozik, H.; Fisher, M. H.; Hoogsteen, K.; Springer, J. P. Chemical modification of paraherquamide. 1. Unusual reactions and absolute sterochemistry. J. Org. Chem. 1989, 54, 2657-2663.
    • (1989) J. Org. Chem. , vol.54 , pp. 2657-2663
    • Blizzard, T.A.1    Marino, G.2    Mrozik, H.3    Fisher, M.H.4    Hoogsteen, K.5    Springer, J.P.6
  • 32
    • 0000127604 scopus 로고    scopus 로고
    • Ligands of the nicotinic acetylcholine receptor as insecticides
    • Nauen, R.; Ebbinghaus, U.; Tietjen, K. Ligands of the nicotinic acetylcholine receptor as insecticides. Pestic. Sci. 1999, 55, 566-614.
    • (1999) Pestic. Sci. , vol.55 , pp. 566-614
    • Nauen, R.1    Ebbinghaus, U.2    Tietjen, K.3
  • 34
    • 0036720920 scopus 로고    scopus 로고
    • Paraherquamide and 2-deoxy-paraherquamide distinguish cholinergic receptor subtypes in Ascaris muscle
    • Erratum in J. Pharmacol. Exp. Ther. 2002, 302, 888
    • Robertson, A. P.; Clark, C. L.; Burns, T. A.; Thompson, D. P.; Geary T. G.; Trailovic, S. M.; Martin, R. J. Paraherquamide and 2-deoxy-paraherquamide distinguish cholinergic receptor subtypes in Ascaris muscle. J. Pharmacol. Exp. Ther. 2002, 302, 853-860. Erratum in J. Pharmacol. Exp. Ther. 2002, 302, 888.
    • (2002) J. Pharmacol. Exp. Ther. , vol.302 , pp. 853-860
    • Robertson, A.P.1    Clark, C.L.2    Burns, T.A.3    Thompson, D.P.4    Geary, T.G.5    Trailovic, S.M.6    Martin, R.J.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.