메뉴 건너뛰기




Volumn 31, Issue 6, 2005, Pages 1381-1400

4,8-Dimethyldecanal, the aggregation pheromone of Tribolium castaneum, is biosynthesized through the fatty acid pathway

Author keywords

2 octynoic acid; 4,8 dimethyldecanal; Aggregation pheromone; Biosynthesis; Fatty acid pathway; JH III; Mevastatin; Red flour beetle; Tenebrionidae; Tribolium castaneum

Indexed keywords

2 OCTYNOIC ACID; 2-OCTYNOIC ACID; 4,8 DIMETHYLDECANAL; 4,8-DIMETHYLDECANAL; ACETIC ACID DERIVATIVE; ALDEHYDE; CARBON; COMPACTIN; DEUTERIUM; DRUG DERIVATIVE; ESTER; FATTY ACID; JUVENILE HORMONE III; MEVALONIC ACID; MEVALONOLACTONE; MEVINOLIN; MONOUNSATURATED FATTY ACID; PHEROMONE; PROPIONIC ACID DERIVATIVE; SESQUITERPENE;

EID: 20544455658     PISSN: 00980331     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10886-005-5292-3     Document Type: Article
Times cited : (17)

References (44)
  • 1
    • 0041707794 scopus 로고    scopus 로고
    • Frontalin: De novo biosynthesis of an aggregation pheromone component by Dendroctonus spp. bark beetles (Coleoptera: Scolytidae)
    • L. S. Barkawi W. Francke G. J. Blomquist S. J. Seybold 2003 Frontalin: De novo biosynthesis of an aggregation pheromone component by Dendroctonus spp. bark beetles (Coleoptera: Scolytidae) Insect Biochem. Mol. Biol. 33 773 788
    • (2003) Insect Biochem. Mol. Biol. , vol.33 , pp. 773-788
    • Barkawi, L.S.1    Francke, W.2    Blomquist, G.J.3    Seybold, S.J.4
  • 2
    • 0029912943 scopus 로고    scopus 로고
    • Polyketide origin of pheromones of Carpophilus davidsoni and C. mutilatus (Coleoptera: Nitidulidae)
    • R. J. Bartelt D. Weisleder 1996 Polyketide origin of pheromones of Carpophilus davidsoni and C. mutilatus (Coleoptera: Nitidulidae) Bioorg. Med. Chem. 4 429 438
    • (1996) Bioorg. Med. Chem. , vol.4 , pp. 429-438
    • Bartelt, R.J.1    Weisleder, D.2
  • 3
    • 0000943956 scopus 로고
    • A facile removal of the tetrahydropyranyl protecting group from alcohol derivatives
    • R. Beier B. P. Mundy 1979 A facile removal of the tetrahydropyranyl protecting group from alcohol derivatives Synth. Commun. 9 271 273
    • (1979) Synth. Commun. , vol.9 , pp. 271-273
    • Beier, R.1    Mundy, B.P.2
  • 4
    • 0016281931 scopus 로고
    • Incorporation and dilution values-their calculation in mass spectrally assayed stable isotope labeling experiments
    • I. M. Campbell 1974 Incorporation and dilution values-their calculation in mass spectrally assayed stable isotope labeling experiments Bioorg. Chem. 3 386 387
    • (1974) Bioorg. Chem. , vol.3 , pp. 386-387
    • Campbell, I.M.1
  • 5
    • 0026668337 scopus 로고
    • Biosynthesis and endocrine control of the production of the German cockroach sex pheromone 3,11-dimethylnonacosan-2-one
    • J. Chase K. Touhara G. D. Prestwich C. Schal G. J. Blomquist 1992 Biosynthesis and endocrine control of the production of the German cockroach sex pheromone 3,11-dimethylnonacosan-2-one Proc. Natl. Acad. Sci. U.S.A. 89 6050 6054
    • (1992) Proc. Natl. Acad. Sci. U.S.A. , vol.89 , pp. 6050-6054
    • Chase, J.1    Touhara, K.2    Prestwich, G.D.3    Schal, C.4    Blomquist, G.J.5
  • 6
    • 0001763503 scopus 로고
    • Effect of juvenile hormone analog, fenoxycarb, on pheromone production by Ips paraconfusus (Coleoptera: Scolytidae)
    • N. M. Chen J. H. Borden H. D. Pierce Jr 1988 Effect of juvenile hormone analog, fenoxycarb, on pheromone production by Ips paraconfusus (Coleoptera: Scolytidae) J. Chem. Ecol. 14 1087 1098
    • (1988) J. Chem. Ecol. , vol.14 , pp. 1087-1098
    • Chen, N.M.1    Borden, J.H.2    Pierce Jr., H.D.3
  • 8
    • 0017043554 scopus 로고
    • Competitive inhibition of 3-hydroxy-3-methylglutaryl coenzyme a reductase by ML-36A and ML-236B fungal metabolites, having hypocholesterolemic activity
    • A. Endo M. Kuroda K. Tanzawa 1976 Competitive inhibition of 3-hydroxy-3-methylglutaryl coenzyme A reductase by ML-36A and ML-236B fungal metabolites, having hypocholesterolemic activity FEBS Lett. 72 323 326
    • (1976) FEBS Lett. , vol.72 , pp. 323-326
    • Endo, A.1    Kuroda, M.2    Tanzawa, K.3
  • 9
    • 34250240416 scopus 로고
    • Sexually dimorphic setiferous sex patch in the male red flour beetles Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae): site of aggregation pheromone production
    • D. L. Faustini W. E. Burkholder R. J. Laub 1981 Sexually dimorphic setiferous sex patch in the male red flour beetles Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae): site of aggregation pheromone production J. Chem. Ecol. 7 465 480
    • (1981) J. Chem. Ecol. , vol.7 , pp. 465-480
    • Faustini, D.L.1    Burkholder, W.E.2    Laub, R.J.3
  • 10
    • 0022375574 scopus 로고
    • Inactivation of general acyl-CoA dehydrogenase from pig kidney by 2-alkynoyl coenzyme a derivatives: Initial aspects
    • K. Freund J. Mizzer W. Dick C. Thorpe 1985 Inactivation of general acyl-CoA dehydrogenase from pig kidney by 2-alkynoyl coenzyme A derivatives: Initial aspects Biochemistry 24 5996 6002
    • (1985) Biochemistry , vol.24 , pp. 5996-6002
    • Freund, K.1    Mizzer, J.2    Dick, W.3    Thorpe, C.4
  • 11
    • 0042822513 scopus 로고
    • Selective epoxidation of terminal double bonds: 10,11-Epoxyfarnesyl acetate
    • Wiley New York
    • R. P. Hanzlik 1988 Selective epoxidation of terminal double bonds: 10,11-Epoxyfarnesyl acetate W. E. Noland Organic Syntheses Coll. Vol. 6 Wiley New York 560 564
    • (1988) Organic Syntheses Coll. Vol. 6 , pp. 560-564
    • Hanzlik, R.P.1    Noland, W.E.2
  • 14
    • 0032890916 scopus 로고    scopus 로고
    • Biosynthesis of 4-methyl-1-nonanol: Female-produced sex pheromone of the yellow mealworm beetle, Tenebrio molitor (Coleoptera: Tenebrionidae)
    • N. Islam R. Bacala A. Moore D. Vanderwel 1999 Biosynthesis of 4-methyl-1-nonanol: Female-produced sex pheromone of the yellow mealworm beetle, Tenebrio molitor (Coleoptera: Tenebrionidae) Insect Biochem. Mol. Biol. 29 201 208
    • (1999) Insect Biochem. Mol. Biol. , vol.29 , pp. 201-208
    • Islam, N.1    Bacala, R.2    Moore, A.3    Vanderwel, D.4
  • 15
    • 0028801605 scopus 로고
    • Regulation and biosynthesis of pheromone components in the double spined bark beetle Ips duplicatus (Coleoptera: Scolytidae)
    • P. Ivarsson G. Birgersson 1995 Regulation and biosynthesis of pheromone components in the double spined bark beetle Ips duplicatus (Coleoptera: Scolytidae) J. Insect Physiol. 41 840 843
    • (1995) J. Insect Physiol. , vol.41 , pp. 840-843
    • Ivarsson, P.1    Birgersson, G.2
  • 16
    • 0000353385 scopus 로고
    • Demonstration of de novo pheromone biosynthesis in Ips duplicatus (Coleoptera: Scolytidae): Inhibition of ipsdienol and E-myrcenol production by compactin
    • P. Ivarsson F. Schlyter G. Birgersson 1993 Demonstration of de novo pheromone biosynthesis in Ips duplicatus (Coleoptera: Scolytidae): Inhibition of ipsdienol and E-myrcenol production by compactin Insect Biochem. Mol. Biol. 23 655 662
    • (1993) Insect Biochem. Mol. Biol. , vol.23 , pp. 655-662
    • Ivarsson, P.1    Schlyter, F.2    Birgersson, G.3
  • 19
    • 10344258650 scopus 로고    scopus 로고
    • Deuterated analogues of 4,8-dimethyldecanal, the aggregation pheromone of Tribolium castaneum: Synthesis and pheromonal activity
    • J. Kim S. Matsuyama T. Suzuki 2004 Deuterated analogues of 4,8-dimethyldecanal, the aggregation pheromone of Tribolium castaneum: synthesis and pheromonal activity J. Label. Compd. Radiopharm. 47 921 934
    • (2004) J. Label. Compd. Radiopharm. , vol.47 , pp. 921-934
    • Kim, J.1    Matsuyama, S.2    Suzuki, T.3
  • 22
    • 0020383110 scopus 로고
    • Compactin inhibits insect HMG-CoA reductase and juvenile hormone biosynthesis
    • D. Monger W. A. Lim F. J. Kézdy J. H. Law 1982 Compactin inhibits insect HMG-CoA reductase and juvenile hormone biosynthesis Biochem. Biophys. Res. Commun. 105 1374 1380
    • (1982) Biochem. Biophys. Res. Commun. , vol.105 , pp. 1374-1380
    • Monger, D.1    Lim, W.A.2    Kézdy, F.J.3    Law, J.H.4
  • 23
    • 0001422786 scopus 로고    scopus 로고
    • Synthesis of 2-polyprenyl-substituted polyprenols and their conversion into phosphates
    • H. Nagano T. Nagasawa M. Sakuma 1997 Synthesis of 2-polyprenyl- substituted polyprenols and their conversion into phosphates Bull. Chem. Soc. Jpn. 70 1969 1976
    • (1997) Bull. Chem. Soc. Jpn. , vol.70 , pp. 1969-1976
    • Nagano, H.1    Nagasawa, T.2    Sakuma, M.3
  • 24
    • 0033605188 scopus 로고    scopus 로고
    • Synthesis of 6-(poly)prenyl-substituted polyprenols and their phosphates
    • H. Nagano E. Nakanishi S. Takajo M. Sakuma K. Kudo 1999 Synthesis of 6-(poly)prenyl-substituted polyprenols and their phosphates Tetrahedron 55 2591 2608
    • (1999) Tetrahedron , vol.55 , pp. 2591-2608
    • Nagano, H.1    Nakanishi, E.2    Takajo, S.3    Sakuma, M.4    Kudo, K.5
  • 26
    • 0022621896 scopus 로고
    • Enhanced production of aggregation pheromones in four stored-product coleopterans feeding on methoprene-treated oats
    • A. M. Pierce H. D. Pierce Jr J. H. Borden A. C. Oehlschlager 1986 Enhanced production of aggregation pheromones in four stored-product coleopterans feeding on methoprene-treated oats Experientia 42 164 165
    • (1986) Experientia , vol.42 , pp. 164-165
    • Pierce, A.M.1    Pierce Jr., H.D.2    Borden, J.H.3    Oehlschlager, A.C.4
  • 27
    • 0032421114 scopus 로고    scopus 로고
    • The femoral setiferous glands of Tribolium castaneum males and production of the pheromone 4,8-dimethyldecanal
    • M. C. B. Qazi C. R. B. Boake S. M. Lewis 1998 The femoral setiferous glands of Tribolium castaneum males and production of the pheromone 4,8-dimethyldecanal Entomol. Exp. Appl. 89 313 317
    • (1998) Entomol. Exp. Appl. , vol.89 , pp. 313-317
    • Qazi, M.C.B.1    Boake, C.R.B.2    Lewis, S.M.3
  • 28
    • 0001133509 scopus 로고
    • 14C using alkyl phosphates
    • 14C using alkyl phosphates J. Am. Chem. Soc. 72 2299 2317
    • (1950) J. Am. Chem. Soc. , vol.72 , pp. 2299-2317
    • Ropp, G.A.1
  • 31
    • 0001506063 scopus 로고
    • 4,8-Dimethyldecanal: The aggregation pheromone of the flour beetles, Tribolium castaneum and T. confusum (Coleoptera: Tenebrionidae)
    • T. Suzuki 1980 4,8-Dimethyldecanal: The aggregation pheromone of the flour beetles, Tribolium castaneum and T. confusum (Coleoptera: Tenebrionidae) Agric. Biol. Chem. 44 2519 2520
    • (1980) Agric. Biol. Chem. , vol.44 , pp. 2519-2520
    • Suzuki, T.1
  • 32
    • 85008074636 scopus 로고
    • (4R,8R)-()-4,8-Dimethyldecanal: The natural aggregation pheromone of the red flour beetle, Tribolium castaneum (Coleoptera: Tenebrionidae)
    • T. Suzuki K. Mori 1983 (4R,8R)-()-4,8-Dimethyldecanal: the natural aggregation pheromone of the red flour beetle, Tribolium castaneum (Coleoptera: Tenebrionidae) Appl. Entomol. Zool. 18 134 136
    • (1983) Appl. Entomol. Zool. , vol.18 , pp. 134-136
    • Suzuki, T.1    Mori, K.2
  • 33
    • 85011189151 scopus 로고
    • Aggregation pheromone of Tribolium freemani Hinton (Coleoptera, Tenebrionidae): I. Identification of the aggregation pheromone
    • T. Suzuki H. Nakakita Y. Kuwahara 1987 Aggregation pheromone of Tribolium freemani Hinton (Coleoptera, Tenebrionidae): I. Identification of the aggregation pheromone Appl. Entomol. Zool. 22 340 347
    • (1987) Appl. Entomol. Zool. , vol.22 , pp. 340-347
    • Suzuki, T.1    Nakakita, H.2    Kuwahara, Y.3
  • 34
    • 85008067231 scopus 로고
    • A sex attractant of the yellow mealworm, Tenebrio molitor L., and its role in mating behaviour
    • Y. Tanaka H. Honda K. Ohsawa I. Yamamoto 1986 A sex attractant of the yellow mealworm, Tenebrio molitor L., and its role in mating behaviour J. Pestic. Sci. 11 49 55
    • (1986) J. Pestic. Sci. , vol.11 , pp. 49-55
    • Tanaka, Y.1    Honda, H.2    Ohsawa, K.3    Yamamoto, I.4
  • 35
    • 84996043849 scopus 로고
    • Absolute configuration of 4-methyl-1-nonanol, a sex attractant of the yellow mealworm, Tenebrio molitor L
    • Y. Tanaka H. Honda K. Ohsawa I. Yamamoto 1989 Absolute configuration of 4-methyl-1-nonanol, a sex attractant of the yellow mealworm, Tenebrio molitor L J. Pestic. Sci. 14 197 202
    • (1989) J. Pestic. Sci. , vol.14 , pp. 197-202
    • Tanaka, Y.1    Honda, H.2    Ohsawa, K.3    Yamamoto, I.4
  • 36
    • 4544232906 scopus 로고    scopus 로고
    • Revision of the structure of the major aggregation pheromone of the broad-horned flour beetle (Gnatocerus cornutus) to (1S,4R,5R)-alpha-acoradiene by its synthesis
    • T. Tashiro S. Kurosawa K. Mori 2004 Revision of the structure of the major aggregation pheromone of the broad-horned flour beetle (Gnatocerus cornutus) to (1S,4R,5R)-alpha-acoradiene by its synthesis Biosci. Biotechnol. Biochem. 68 663 670
    • (2004) Biosci. Biotechnol. Biochem. , vol.68 , pp. 663-670
    • Tashiro, T.1    Kurosawa, S.2    Mori, K.3
  • 37
    • 0032051787 scopus 로고    scopus 로고
    • Identification of (+)-acoradiene as an aggregation pheromone for Gnatocerus cornutus (F.) (Coleoptera: Tenebrionidae)
    • S. Tebayashi N. Hirai T. Suzuki S. Matsuyama H. Nakakita T. Nemoto H. Nakanishi 1998a Identification of (+)-acoradiene as an aggregation pheromone for Gnatocerus cornutus (F.) (Coleoptera: Tenebrionidae) J. Stored Prod. Res. 34 99 106
    • (1998) J. Stored Prod. Res. , vol.34 , pp. 99-106
    • Tebayashi, S.1    Hirai, N.2    Suzuki, T.3    Matsuyama, S.4    Nakakita, H.5    Nemoto, T.6    Nakanishi, H.7
  • 38
    • 0039394754 scopus 로고    scopus 로고
    • α-Cedren-14-al: Minor aggregation pheromone component of Gnatocerus cornutus (F.) (Coleoptera: Tenebrionidae)
    • S. Tebayashi N. Hirai T. Suzuki S. Matsuyama H. Nakakita T. Nemoto H. Nakanishi 1998b α-Cedren-14-al: minor aggregation pheromone component of Gnatocerus cornutus (F.) (Coleoptera: Tenebrionidae) J. Pestic. Sci. 23 402 406
    • (1998) J. Pestic. Sci. , vol.23 , pp. 402-406
    • Tebayashi, S.1    Hirai, N.2    Suzuki, T.3    Matsuyama, S.4    Nakakita, H.5    Nemoto, T.6    Nakanishi, H.7
  • 41
    • 0000710779 scopus 로고
    • Biosynthesis of pheromones and endocrine regulation of pheromone production in Coleoptera
    • Academic Press Orlando, FL
    • D. Vanderwel A. C. Oehlschlager 1987 Biosynthesis of pheromones and endocrine regulation of pheromone production in Coleoptera G. D. Prestwich G. J. Blomquist Pheromone Biochemistry Academic Press Orlando, FL 175 215
    • (1987) Pheromone Biochemistry , pp. 175-215
    • Vanderwel, D.1    Oehlschlager, A.C.2    Prestwich, G.D.3    Blomquist, G.J.4
  • 42
  • 44
    • 1242299612 scopus 로고    scopus 로고
    • Sex pheromone biosynthesis in the pine caterpillar moth, Dendrolimus punctatus (Lepidoptera: Lasiocampidae): pathway leading to Z5-monoene and 5,7-conjugated diene components
    • C.-H. Zhao R. O. Adlof C. Löfstedt 2004 Sex pheromone biosynthesis in the pine caterpillar moth, Dendrolimus punctatus (Lepidoptera: Lasiocampidae): pathway leading to Z5-monoene and 5,7-conjugated diene components Insect Biochem. Mol. Biol. 34 261 271
    • (2004) Insect Biochem. Mol. Biol. , vol.34 , pp. 261-271
    • Zhao, C.-H.1    Adlof, R.O.2    Löfstedt, C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.