Geraniol dehydrogenase, the key enzyme in biosynthesis of the alarm pheromone, from the astigmatid mite Carpoglyphus lactis (Acari: Carpoglyphidae)

FEBS Journal

Volumn 275, Issue 11, 2008, Pages 2807-2817

  Noge, Koji ^a,b   Kato, Makiko ^a   Mori, Naoki ^a   Kataoka, Michihiko ^a   Tanaka, Chihiro ^a   Yamasue, Yuji ^a   Nishida, Ritsuo ^a   Kuwahara, Yasumasa ^a,c  

^a KYOTO UNIVERSITY   (Japan)

^b UNIVERSITY OF ARIZONA   (United States)

^c Ukyo ku   (Japan)

Author keywords

Alarm pheromone; Biosynthesis; Carpoglyphus lactis; Geraniol dehydrogenase; Monomeric alcohol dehydrogenase

Indexed keywords

ALCOHOL DEHYDROGENASE; AMINO ACID; GERANIOL DEHYDROGENASE; NEROL; NICOTINAMIDE ADENINE DINUCLEOTIDE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; PHEROMONE;

ACARI; AMINO ACID SEQUENCE; ARTICLE; BIOSYNTHESIS; CARPOGLYPHUS LACTIS; CHROMATOGRAPHY; CONTROLLED STUDY; ENZYME BINDING; ENZYME METABOLISM; ENZYME PURIFICATION; ENZYME SPECIFICITY; ENZYME STRUCTURE; ENZYME SYNTHESIS; MITE; MOLECULAR WEIGHT; NONHUMAN; NUCLEOTIDE SEQUENCE; PHYLOGENY; PRIORITY JOURNAL;

ALCOHOL DEHYDROGENASE; ALCOHOL OXIDOREDUCTASES; AMINO ACID SEQUENCE; ANIMALS; BASE SEQUENCE; KINETICS; MITES; MOLECULAR SEQUENCE DATA; MONOTERPENES; OXIDOREDUCTASES; OXYGEN; PHEROMONES; PROTEIN STRUCTURE, TERTIARY; SUBSTRATE SPECIFICITY; TERPENES; ZINC;

ACARI; CARPOGLYPHIDAE; CARPOGLYPHUS LACTIS; MAMMALIA;

EID: 43549089797     PISSN: 1742464X     EISSN: 17424658     Source Type: Journal    
DOI: 10.1111/j.1742-4658.2008.06421.x     Document Type: Article

References (45)

1. Butenandt A, Beckmann R, Stamm D Hecker E (1959) Über den Sexual-Lockstoff des Seidenspinners Bombyx mori. Reindarstellung und Konstitution. Z Naturforsch 14, 283 284.
2. Kuwahara Y (2004) Chemical ecology of astigmatid mites. In Advances in Insect Chemical Ecology (Cardé RT Millar JG, eds pp. 76 109. Cambridge University Press, Cambridge, UK.
3. Kuwahara Y, Matsumoto K Wada Y (1980) Pheromone study on acarid mite. IV. Citral: composition and function as an alarm pheromone and its secretory gland in four species of acarid mites. Jpn J Sanit Zool 31, 73 80.
4. Kuwahara Y, Koshii T, Okamoto M, Matsumoto K Suzuki T (1991) Chemical ecology on astigmatid mites. XXX. Neral as the alarm pheromone of Glycyphagus domesticus (De Geer) (Acarina, Glycyphagidae). Jpn J Sanit Zool 42, 29 32.
5. Kuwahara Y, Ibi T, Nakatani Y, Ryono A, Mori N, Sakata T, Okabe K, Tagami K Kurosa K (2001) Chemical ecology of astigmatid mites. LXI. Neral, the alarm pheromone of Schwiebea elongata (Acari: Acaridae). J Acarol Soc Jpn 10, 19 25.
6. Leal WS, Kuwahara Y, Suzuki T Kurosa K (1989) The alarm pheromone of the mite Suidasia medanensis Oudemans, 1924 (Acariformes, Suidasiidae). Agric Biol Chem 53, 2703 2709.
7. Shimizu N, Noge K, Mori N, Nishida R Kuwahara Y (2004) Chemical ecology of astigmatid mites. LXXIII. Neral as an alarm pheromone on the acarid mite, Oulenzia sp. (Astigmata: Winterschmidtiidae). J Acarol Soc Jpn 13, 57 64.
8. Nishimura K, Shimizu N, Mori N Kuwahara Y (2002) Chemical ecology of astigmatid mite. LXIV. The alarm pheromone neral functions as attractant in Schwiebea elongata (Banks) (Acari: Acaridae). Appl Entomol Zool 37, 13 18.
9. Hiraoka H, Mori N, Okabe K, Nishida R Kuwahara Y (2002) Chemical ecology of astigmatid mites. LXVII. Neral [3,7-dimethyl-(Z)-2,6-octadienal]: the female sex pheromone of an acarid mite, Histiogaster sp. (Acari: Acaridae). J Acarol Soc Jpn 11, 17 26.
10. Okamoto M, Matsumoto K, Wada Y Kuwahara Y (1981) Studies on antifungal effect of mite alarm pheromone citral. 2. Antifungal effect of the hexane extracts of the grain mites and some analogues of citral. Jpn J Sanit Zool 32, 265 270.
11. 13C incorporation into other opisthonotal gland exudates. J Pestic Sci 29, 27 32.
12. Noge K, Kato M, Iguchi T, Mori N, Nishida R Kuwahara Y (2005) Biosynthesis of neral in Carpoglyphus lactis (Acari: Carpoglyphidae) and detection of its key enzymes, geraniol dehydrogenase, by electrophoresis. J Acarol Soc Jpn 14, 75 81.
13. Sangwan RS, Singh-Sangwan N Luthra R (1993) Metabolism of acyclic monoterpenes: partial purification and properties of geraniol dehydrogenase from lemongrass (Cymbopogon flexuosus Stapt.) leaves. J Plant Physiol 142, 129 134.
14. Potty VH Bruemmer JH (1970) Oxidation of geraniol by an enzyme system from orange. Phytochemistry 9, 1003 1007.
15. Sekiwa-Iijima Y, Aizawa Y Kubota K (2001) Geraniol dehydrogenase activity related to aroma formation in ginger (Zingiber officinale Roscoe). J Agric Food Chem 49, 5902 5906.
16. Iijima Y, Wang G, Fridman E Pichersky E (2006) Analysis of the enzymatic formation of citral in the glands of sweet basil. Arch Biochem Biophys 448, 141 149.
17. 2. J Ferment Technol 53, 459 463.
18. Wolken WAM van der Werf MJ (2001) Geraniol biotransformation-pathway in spores of Penicillium digitatum. Appl Microbiol Biotechnol 57, 731 737.
19. Hatanaka A, Sekiya J Kajiwara T (1976) Subunit composition of alcohol dehydrogenase from Thea sinensis seeds and its substrate specificity for monoterpenes. Phytochemistry 15, 487 488.
20. Langston PJ, Pace CN Hart GE (1980) Wheat alcohol dehydrogenase isozymes. Plant Physiol 65, 518 522.
21. Atrian S Gonzàlez-Duarte R (1985) Purification and molecular characterization of alcohol dehydrogenase from Drosophila hydei: conservation in the biochemical features of the enzyme in several species of Drosophila. Biochem Genet 23, 891 911.
22. Moreno A Parés X (1991) Purification and characterization of a new alcohol dehydrogenase from human stomach. J Biol Chem 266, 1128 1133.
23. Kosjek B, Stampfer W, Pogorevc M, Goessler W, Faber K Kroutil W (2004) Purification and characterization of a chemotolerant alcohol dehydrogenase applicable to coupled redox reactions. Biotech Bioeng 86, 55 62.
24. Tsigos I, Velonia K, Smonou I Bouriotis V (1998) Purification and characterization of an alcohol dehydrogenase from the Antarctic psychrophile Moraxella sp. TAE123. Eur J Biochem 254, 356 362.
25. + oxidoreductase of Rauwolfia serpentina cells: the key enzyme in biosynthesis of monoterpene alcohols. J Biochem (Tokyo) 109, 341 347.
26. Wuryatmo E, Klieber A Scott ES (2003) Inhibition of citrus postharvest pathogens by vapor of citral and related compounds in culture. J Agric Food Chem 51, 2637 2640.
27. Suzuki T, Haga K, Tsutsumi T Matsuyama S (2004) Analysis of anal secretions from phlaeothripine thrips. J Chem Ecol 30, 409 423.
28. Baker FC, Mauchamp B, Tsai LW Schooley DA (1983) Farnesol and farnesal dehydrogenase(s) in corpora allata of the tobacco hornworm moth, Manduca sexta. J Lipid Res 24, 1586 1594.
29. Sperry AE Sen SE (2001) Farnesol oxidation in insects: evidence that the biosynthesis of insect juvenile hormone is mediated by a specific alcohol oxidase. Insect Biochem Mol Biol 31, 171 178.
30. + oxidoreductase from catmint (Nepeta racemosa). Arch Biochem Biophys 318, 105 112.
31. Inoue H, Tsuji H Uritani I (1984) Characterization and activity change of farnesol dehydrogenase in black rot fungus-infected sweet potato. Agric Biol Chem 48, 733 738.
32. Kleiner DE Johnston M (1985) Purification and properties of a secondary alcohol dehydrogenase from the parasitic protozoan Tritrichomonas foetus. J Biol Chem 260, 8038 8043.
33. Jörnvall H, Höög JO Persson B (1999) SDR and MDR: completed genome sequences show these protein families to be large, of old origin, and of complex nature. FEBS Lett 445, 261 264.
34. Jörnvall H, Persson B Jeffery J (1987) Characteristics of alcohol/polyol dehydrogenases. The zinc-containing long-chain alcohol dehydrogenases. Eur J Biochem 167, 195 201.
35. Flinta C, Persson B, Jörnvall H von Heijne G (1986) Sequence determinants of cytosolic N-terminal protein processing. Eur J Biochem 154, 193 196.
36. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram qualities of protein utilizing the principle of protein-dye binding. Anal Biochem 72, 248 254.
37. Hiraoka H, Noge K, Mori N, Okabe K, Tagami K, Nishida R Kuwahara Y (2003) Chemical ecology of astigmatid mites. LXXIV (4E)-Dehydrogeranial [(2E,4E)-3,7-dimethyl-2,4,6-octatrienal] as the alarm pheromone of acarid mite Histiogaster sp. A096 (Acari: Acaridae). Jpn J Environ Entomol Zool 14, 233 240.
38. Laemmli UK (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227, 680 685.
39. Honda K, Tsuboi H, Minetoki T, Nose H, Sakamoto K, Kataoka M Shimizu S (2005) Expression of the Fusarium oxysporum lactonase gene in Aspergillus oryzae: molecular properties of the recombinant enzyme and its application. Appl Microbiol Biotechnol 66, 520 526.
40. Takano Y, Kubo Y, Shimizu K, Mise K, Okuno T Furusawa I (1995) Structural analysis of PKS1, a polyketide synthase gene involved in melanin biosynthesis in Colletotrichum lagenarium. Mol Gen Genet 249, 162 167.
41. Yoshimi A, Tsuda M Tanaka C (2004) Cloning and characterization of the histidine kinase gene Dic1 from Cochliobolus heterostrophus that confers dicarboximide resistance and osmotic adaptation. Mol Gen Genomics 271, 228 236.
42. Noge K, Mori N, Tanaka C, Nishida R, Tsuda M Kuwahara Y (2005) Identification of astigmatid mites using the second internal transcribed spacer (ITS2) region and its application for phylogenetic study. Exp Appl Acarol 35, 29 46.
43. Thompson JD, Higgins DJ Gibson TJ (1994) Clustal W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res 22, 4673 4680.
44. Swofford DL (2002) PAUP* 4.0 Beta Version: Phylogenetic Analysis and Using Parsimony (and other methods). Sinauer Associates Inc., Sunderland, MA.
45. Felsenstein J (1985) Confidence limits on phylogenies: an approach using the bootstrap. Evolution 39, 783 791.