메뉴 건너뛰기




Volumn 259, Issue 1-2, 1999, Pages 175-180

Biosynthesis of scarab beetle pheromones: Enantioselective 8- hydroxylation of fatty acids

Author keywords

Anomala cuprea; Anomala osakana; Buibuilactone; Japonilure

Indexed keywords

PHEROMONE;

EID: 0033556087     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1327.1999.00018.x     Document Type: Article
Times cited : (22)

References (36)
  • 1
    • 0001864237 scopus 로고
    • Pheromone biosynthesis in lepidopterans: Desaturation and chain shortening
    • (Prestwich, G.D. & Blomquist. G.J., eds), Academic Press, New York
    • Bjostad, L.B., Wolf, W.A. & Roelofs, W.L. (1987) Pheromone biosynthesis in lepidopterans: desaturation and chain shortening. In Pheromone Biochemistry (Prestwich, G.D. & Blomquist. G.J., eds), pp. 77-120. Academic Press, New York.
    • (1987) Pheromone Biochemistry , pp. 77-120
    • Bjostad, L.B.1    Wolf, W.A.2    Roelofs, W.L.3
  • 2
    • 0002540084 scopus 로고    scopus 로고
    • Control of pheromone production in moths
    • (Cardé, R.T. & Minks, A.K., eds), Chapman and Hall, New York
    • Raina, A.K. (1997) Control of pheromone production in moths. In Insect Pheromone Research. New Directions (Cardé, R.T. & Minks, A.K., eds), pp. 21-30. Chapman and Hall, New York.
    • (1997) Insect Pheromone Research. New Directions , pp. 21-30
    • Raina, A.K.1
  • 4
    • 0026668337 scopus 로고
    • Biosynthesis and endocrine control. Of the production of the German cockroach sex pheromone 3,11-dimethylnonacosan-3-one
    • Chase, J., Touhara, K., Prestwich, G.D., Schal, C. & Blomquist, G.J. (1992) Biosynthesis and endocrine control. of the production of the German cockroach sex pheromone 3,11-dimethylnonacosan-3-one. Proc. Natl Acad. Sci. USA 89, 6050-6054.
    • (1992) Proc. Natl Acad. Sci. USA , vol.89 , pp. 6050-6054
    • Chase, J.1    Touhara, K.2    Prestwich, G.D.3    Schal, C.4    Blomquist, G.J.5
  • 5
    • 0029887613 scopus 로고    scopus 로고
    • Transformation of presumptive precursors to frontalin and exo-brevicomin by bark beetles and the West Indian sugarcane weevil (Coleoptera)
    • Perez, A.L., Gries, R., Gries, G. & Oehlschlager, A.C. (1996) Transformation of presumptive precursors to frontalin and exo-brevicomin by bark beetles and the West Indian sugarcane weevil (Coleoptera). Bioorg. Med. Chem. 4, 445-450.
    • (1996) Bioorg. Med. Chem. , vol.4 , pp. 445-450
    • Perez, A.L.1    Gries, R.2    Gries, G.3    Oehlschlager, A.C.4
  • 6
    • 0029912943 scopus 로고    scopus 로고
    • Polyketide origin of pheromones of carpophilus davidsoni and C. mutilatus (Coleoptera: Nitidulidae)
    • Bartelt, R.J. & Weisleder, D. (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
  • 8
    • 0014958519 scopus 로고
    • Sex attractant of the grass grab beetle
    • Henzell, R.F. & Lowe, M.D. (1970) Sex attractant of the grass grab beetle. Science 168 1005-1006.
    • (1970) Science , vol.168 , pp. 1005-1006
    • Henzell, R.F.1    Lowe, M.D.2
  • 9
    • 0029830814 scopus 로고    scopus 로고
    • Aggregation of the scarab beetle Holotrichia consanguinea in response to female-released pheromone suggests secondary function hypothesis for semiochemical
    • Leal, W.S., Yadava, C.P.S. & Vijayvergia, J.N. (1996) Aggregation of the scarab beetle Holotrichia consanguinea in response to female-released pheromone suggests secondary function hypothesis for semiochemical. J. Chem. Ecol. 22, 1557-1566.
    • (1996) J. Chem. Ecol. , vol.22 , pp. 1557-1566
    • Leal, W.S.1    Yadava, C.P.S.2    Vijayvergia, J.N.3
  • 12
    • 0002911294 scopus 로고    scopus 로고
    • Evolution of sex pheromone communication in plant-feeding scarab beetles
    • (Cardé, R.T. & Minks, A.K., eds), Chapman and Hall, New York
    • Leal, W.S. (1997) Evolution of sex pheromone communication in plant-feeding scarab beetles. In Insect Pheromone Research. New Directions (Cardé, R.T. & Minks, A.K., eds), pp. 505-513. Chapman and Hall, New York.
    • (1997) Insect Pheromone Research. New Directions , pp. 505-513
    • Leal, W.S.1
  • 13
    • 0025987753 scopus 로고
    • (R,Z)-5-(-)-(Oct-1-enyl)oxacyclopentan-2-one the sex pheromone of the scarab beetle anomala cuprea
    • Leal, W.S. (1991) (R,Z)-5-(-)-(Oct-1-enyl)oxacyclopentan-2-one the sex pheromone of the scarab beetle Anomala cuprea. Naturwissenschaften 78, 521-523.
    • (1991) Naturwissenschaften , vol.78 , pp. 521-523
    • Leal, W.S.1
  • 14
    • 0017737061 scopus 로고
    • Identification of the female Japanese beetle sex pheromone: Inhibition of male response by an enantiomer
    • Tumlinson, J.H., Klein, M.G., Doolittle, R.E., Ladd, T.L. & Proveaux, A.T. (1977) Identification of the female Japanese beetle sex pheromone: inhibition of male response by an enantiomer. Science 197, 789-792.
    • (1977) Science , vol.197 , pp. 789-792
    • Tumlinson, J.H.1    Klein, M.G.2    Doolittle, R.E.3    Ladd, T.L.4    Proveaux, A.T.5
  • 15
    • 0029861710 scopus 로고    scopus 로고
    • Chemical communication in scarab beetles: Reciprocal behavioral agonist-antagonist activities of chiral pheromones
    • Leal, W.S. (1996) Chemical communication in scarab beetles: reciprocal behavioral agonist-antagonist activities of chiral pheromones. Proc. Natl Acad. Sci. USA 93, 12112-12115.
    • (1996) Proc. Natl Acad. Sci. USA , vol.93 , pp. 12112-12115
    • Leal, W.S.1
  • 16
    • 0013541202 scopus 로고    scopus 로고
    • Interaction of PBAN with biosynthethic enzymes
    • (Cardé, R.T. & Minks, A.K., eds), Chapman and Hall, New York
    • Roelofs, W.L. & Jurenka, R.A. (1997) Interaction of PBAN with biosynthethic enzymes. In Insect Pheromone Research. New Directions (Cardé, R.T. & Minks, A.K., eds), pp. 42-45. Chapman and Hall, New York.
    • (1997) Insect Pheromone Research. New Directions , pp. 42-45
    • Roelofs, W.L.1    Jurenka, R.A.2
  • 17
    • 85008067914 scopus 로고
    • Rearing method for the production of successive generations of anomala cuprea hope (Coleoptera: Scarabaeidae)
    • [in Japanese]
    • Hatsukade, M., Yamada, K. & Iizuka, Y. (1984) Rearing method for the production of successive generations of Anomala cuprea Hope (Coleoptera: Scarabaeidae). Jpn. J. Entomol. Zool. 28, 14-19[in Japanese].
    • (1984) Jpn. J. Entomol. Zool. , vol.28 , pp. 14-19
    • Hatsukade, M.1    Yamada, K.2    Iizuka, Y.3
  • 18
    • 0000674547 scopus 로고    scopus 로고
    • (R,Z)-7,15-hexadecadien-4-olide, sex pheromone of the yellowish elongate chafer
    • Leal, W.S., Kuwahara, S., Ono, M. & Kubota, S. (1996) (R,Z)-7,15-Hexadecadien-4-olide, sex pheromone of the yellowish elongate chafer, Heptophylla picea. Bioorg. Med. Chem. 4, 315-321.
    • (1996) Heptophylla Picea. Bioorg. Med. Chem. , vol.4 , pp. 315-321
    • Leal, W.S.1    Kuwahara, S.2    Ono, M.3    Kubota, S.4
  • 19
    • 0000647632 scopus 로고
    • Identification and synthesis of new γ-lactones from tuberose absolute (polianthes tuberosa)
    • Maurer, B. & Hauser, A. (1982) Identification and synthesis of new γ-lactones from tuberose absolute (Polianthes tuberosa). Helv. Chim. Acta 65, 462-476.
    • (1982) Helv. Chim. Acta , vol.65 , pp. 462-476
    • Maurer, B.1    Hauser, A.2
  • 20
    • 0030969615 scopus 로고    scopus 로고
    • Localization and morphology of sex pheromone glands in scarab beetles
    • Tada, S. & Leal, W.S. (1997) Localization and morphology of sex pheromone glands in scarab beetles, J. Chem. Ecol. 23, 903-915.
    • (1997) J. Chem. Ecol. , vol.23 , pp. 903-915
    • Tada, S.1    Leal, W.S.2
  • 21
    • 0030018325 scopus 로고    scopus 로고
    • Use of deuterium kinetic isotope effect to probe the cryptoregiochemistry of Δ9 desaturation
    • Buist, P.H. & Behrouzian, B. (1996) Use of deuterium kinetic isotope effect to probe the cryptoregiochemistry of Δ9 desaturation. J. Am. Chem. Soc. 118, 6295-6296.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 6295-6296
    • Buist, P.H.1    Behrouzian, B.2
  • 22
    • 0027974788 scopus 로고
    • The scarab beetle anomala albopilosa sakishimana utilizes the same sex pheromone blend as a closely related and geographically isolated species, anomala cuprea
    • Leal, W.S., Kawamura, F. & Ono, M. (1994) The scarab beetle Anomala albopilosa sakishimana utilizes the same sex pheromone blend as a closely related and geographically isolated species, Anomala cuprea. J. Chem. Ecol. 20, 1667-1676.
    • (1994) J. Chem. Ecol. , vol.20 , pp. 1667-1676
    • Leal, W.S.1    Kawamura, F.2    Ono, M.3
  • 23
    • 0000710779 scopus 로고
    • Biosynthesis of pheromones and endocrine regulation of pheromone production in Coleoptera
    • (Prestwich, G.D. & Blomquist, G.J., eds), Academic Press, New York
    • Vanderwel, D. & Oehlschlager, A.C. (1987) Biosynthesis of pheromones and endocrine regulation of pheromone production in Coleoptera. In Pheromone Biochemistry (Prestwich, G.D. & Blomquist, G.J., eds), pp. 175-215. Academic Press, New York.
    • (1987) Pheromone Biochemistry , pp. 175-215
    • Vanderwel, D.1    Oehlschlager, A.C.2
  • 25
    • 0028335991 scopus 로고
    • Oxygenation of polyunsaturated fatty acids by cytochrome P450 monooxygenases
    • Oliw, E.H. (1994) Oxygenation of polyunsaturated fatty acids by cytochrome P450 monooxygenases. Prog. Lipid Res. 33, 329-354.
    • (1994) Prog. Lipid Res. , vol.33 , pp. 329-354
    • Oliw, E.H.1
  • 26
    • 0029998979 scopus 로고    scopus 로고
    • Caste-selective pheromones biosynthesis in honeybees
    • Plettner, E., Slessor, K.N., Winston, M.L. & Oliver, J.E. (1996) Caste-selective pheromones biosynthesis in honeybees. Science 271, 1851-1853.
    • (1996) Science , vol.271 , pp. 1851-1853
    • Plettner, E.1    Slessor, K.N.2    Winston, M.L.3    Oliver, J.E.4
  • 27
    • 0029126780 scopus 로고
    • An oleate 12-hydroxylase from ricinus communis L. is a fatty acyl desaturase homolog
    • van de Loo, F.J., Broun, P., Turner, S. & Somerville, C. (1995) An oleate 12-hydroxylase from Ricinus communis L. is a fatty acyl desaturase homolog. Proc. Natl Acad. Sci. USA 92, 6743-6747.
    • (1995) Proc. Natl Acad. Sci. USA , vol.92 , pp. 6743-6747
    • Van de Loo, F.J.1    Broun, P.2    Turner, S.3    Somerville, C.4
  • 28
    • 0001327107 scopus 로고
    • Metabolism of hydroxy fatty acids: II. Intermediates of the oxidative breakdown of ricinoleic acid by genus candida
    • Okui, S., Uchiyama, M. & Mizugaki, M. (1963) Metabolism of hydroxy fatty acids: II. Intermediates of the oxidative breakdown of ricinoleic acid by genus Candida. J. Biochem. 54, 536-540.
    • (1963) J. Biochem. , vol.54 , pp. 536-540
    • Okui, S.1    Uchiyama, M.2    Mizugaki, M.3
  • 29
    • 0000273385 scopus 로고    scopus 로고
    • Biosynthesis of (R)-γ-decanolactone in the yeast sporobolomyces odorus
    • Haffner, T. & Tressl, R. (1996) Biosynthesis of (R)-γ-decanolactone in the yeast Sporobolomyces odorus. J. Agric. Food Chem. 44, 1218-1223.
    • (1996) J. Agric. Food Chem. , vol.44 , pp. 1218-1223
    • Haffner, T.1    Tressl, R.2
  • 30
    • 0029765448 scopus 로고    scopus 로고
    • Production, identification, and toxicity of γ-decalactone and 4-hydroxydecanoic acid from sporidiobolus spp
    • Feron, G., Dufosse, L., Pierard, E., Bonnarme, P., Le Quere, J.-L. & Spinnler, H.-E. (1996) Production, identification, and toxicity of γ-decalactone and 4-hydroxydecanoic acid from Sporidiobolus spp. Appl. Environ. Microbiol. 62, 2826-2831.
    • (1996) Appl. Environ. Microbiol. , vol.62 , pp. 2826-2831
    • Feron, G.1    Dufosse, L.2    Pierard, E.3    Bonnarme, P.4    Le Quere, J.-L.5    Spinnler, H.-E.6
  • 31
    • 0022550584 scopus 로고
    • Thallophytic allelophathy: Isolation and identification of laetisaric acid
    • Bowers, W.S., Hoch, H.C., Evans, P.H. & Katayama, M. (1986) Thallophytic allelophathy: isolation and identification of laetisaric acid. Science 232, 105-106.
    • (1986) Science , vol.232 , pp. 105-106
    • Bowers, W.S.1    Hoch, H.C.2    Evans, P.H.3    Katayama, M.4
  • 32
    • 0026664198 scopus 로고
    • A linoleic acid (8R)-dioxygenase and hydroperoxide isomerase of the fungus Gaeumannomyces graminis
    • Brodowsky, I.D., Hamberg, M. & Oliw, E.H. (1992) A linoleic acid (8R)-dioxygenase and hydroperoxide isomerase of the fungus Gaeumannomyces graminis. J. Biol. Chem. 267, 14738-14745.
    • (1992) J. Biol. Chem. , vol.267 , pp. 14738-14745
    • Brodowsky, I.D.1    Hamberg, M.2    Oliw, E.H.3
  • 33
    • 84987262300 scopus 로고
    • Über die biosynthese von γ-dodecanolacton in reifenden früchten aroma-komponenten der erdbeere (fragaria ananassa) und des pfirsichs (prunus persica)
    • Schoettler, M. & Boland, W. (1995) Über die Biosynthese von γ-Dodecanolacton in reifenden Früchten Aroma-Komponenten der Erdbeere (Fragaria ananassa) und des Pfirsichs (Prunus persica). Helv. Chim. Acta 78, 847-856.
    • (1995) Helv. Chim. Acta , vol.78 , pp. 847-856
    • Schoettler, M.1    Boland, W.2
  • 34
    • 3142556294 scopus 로고    scopus 로고
    • Biosynthesis of dodecano-4-lactone in ripening fruits: Crucial role of an epoxide-hydrolase in enantioselective generation of aroma components of the nectarine (prunus persica var. nucipersica) and the strawberry (fragaria ananassa)
    • Schöttler, M. & Boland, W. (1996) Biosynthesis of dodecano-4-lactone in ripening fruits: crucial role of an epoxide-hydrolase in enantioselective generation of aroma components of the nectarine (Prunus persica var. nucipersica) and the strawberry (Fragaria ananassa). Helv. Chim. Acta 79, 1488-1496.
    • (1996) Helv. Chim. Acta , vol.79 , pp. 1488-1496
    • Schöttler, M.1    Boland, W.2
  • 35
    • 0029954096 scopus 로고    scopus 로고
    • Biosynthesis of δ-jasmin lactone (=(Z)-dec-7-eno-5-lactone) and (Z,Z)-dodeca-6,9-dieno-4-lactone in the yeast sporobolomyces odorus
    • Haffner, T., Nordsieck, A. & Tressl, R. (1996) Biosynthesis of δ-jasmin lactone (=(Z)-dec-7-eno-5-lactone) and (Z,Z)-dodeca-6,9-dieno-4-lactone in the yeast Sporobolomyces odorus. Helv. Chim. Acta 79, 2088-2099.
    • (1996) Helv. Chim. Acta , vol.79 , pp. 2088-2099
    • Haffner, T.1    Nordsieck, A.2    Tressl, R.3
  • 36
    • 85008744048 scopus 로고
    • Methyl (Z)-5-tetradecenoate: Sex attractant of the soybean beetle, anomala rufocuprea motschulsky (Coleoptera: Scarabaeidae)
    • Tamaki, Y., Sugie, H. & Noguchi, H. (1985) Methyl (Z)-5-tetradecenoate: sex attractant of the soybean beetle, Anomala rufocuprea Motschulsky (Coleoptera: Scarabaeidae). Appl. Entomol. Zool. 20, 359-361.
    • (1985) Appl. Entomol. Zool. , vol.20 , pp. 359-361
    • Tamaki, Y.1    Sugie, H.2    Noguchi, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.