Simple synthesis of mite pheromone β-acaridial and its analogs in the secretion of caloglyphus polyphyllae (acari: Acaridae)

Bioscience, Biotechnology and Biochemistry

Volumn 67, Issue 8, 2003, Pages 1732-1736

  Shimizu, Nobuhiro ^a   Mori, Naoki ^a   Kuwahara, Yasumasa ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Astigmata; Caloglyphus polyphyllae; (Z) acaridial; acaridial; acariolal

Indexed keywords

ACARI; ACARIDAE; ASTIGMATA; CALOGLYPHUS;

ALDEHYDE; AMINOALCOHOL; BETA ACARIDIAL; BETA-ACARIDIAL; SEX PHEROMONE;

ACARI; ANIMAL; ARTICLE; CHEMISTRY; GAS CHROMATOGRAPHY; OXIDATION REDUCTION REACTION; PHYSIOLOGY; SECRETION; STEREOISOMERISM; SYNTHESIS;

ACARI; ALDEHYDES; AMINO ALCOHOLS; ANIMALS; CHROMATOGRAPHY, GAS; OXIDATION-REDUCTION; SEX ATTRACTANTS; STEREOISOMERISM;

EID: 2442616290     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.67.1732     Document Type: Article

References (18)

1. Leal, W. S., Kuwahara, Y., and Suzuki, T., 2(E)-(4-Methyl-3-pentenylidene)-butanedial, b-acaridial: a new type of monoterpene from the mold mite, Tyrophagus putrescentiae (Acarina, Acaridae). Agric. Biol. Chem., 53, 875-878 (1989).
2. Suzuki, T., Haga, K., Leal, W. S., Kodama, S., and Kuwahara, Y., Secretion of thrips, IV. Identification of b-acaridial from three gall-forming thrips (Thysanoptera: Phlaeothripidae). Appl. Entomol. Zool., 24, 222-228 (1989).
3. Leal, W. S., Kuwahara, Y., Suzuki, T., and Kurosa, K., b-Acaridial, the sex pheromone of the acarid mite Caloglyphus polyphyllae. Pheromone study of acarid mites, XXI. Naturwissenschaften, 76, 332-333 (1989).
4. Shimizu, N., Mori, N., and Kuwahara, Y., Aggregation pheromone activity of the female sex pheromone, b-acaridial, in Caloglyphus polyphyllae (Acari: Acaridae). Biosci. Biotechnol. Biochem., 65, 1724-1728 (2001).
5. Noguchi, S., Mori, N., Kurosa, K., and Kuwahara, Y., Chemical ecology of astigmatid mites, XLIX. b-acaridial [2(E)-(4-methyl-3-pentenylidene)-butanedi-al], the alarm pheromone of Tyrophagus longior Gervais (Acarina: Acaridae). Appl. Entomol. Zool., 33, 53-57 (1998).
6. Kuwahara, Y., Chemical ecology of astigmatid mites. In “Environmental Entomology” (in Japanese), eds. Hidaka, T., Matsumoto, Y., Honda, K., and Tatsuki, S., University of Tokyo Press, Tokyo, pp. 380-393 (1999).
7. Kubo, I., Miura, I., Pettei, J. M., Lee, W. Y., Pilkiewicz, F., and Nakanishi, K., Muzigadial and warburganal, potent antifungal antiyeast, and African army worm antifeedant agents. Tetrahedron Lett., 18, 4553-4556 (1977).
8. Barrero, A. F., Manzaneda, E. A., Altarejos, J., Salido, S., Ramos, J. M., Simmonds, M. S. J., and Blaney, W. M., Synthesis of biologically active drimanes and homodrimanes from (-)-sclareol. Tetrahedron, 51, 7435-7450 (1995).
9. Kuwahara, Y., Leal, W. S., Suzuki, T., Maeda, M., and Masutani, T., Antifungal activity of Caloglyphus polyphyllae sex pheromone and other mite exudates. Pheromone study on astigmatid mites, XXIV. Naturwissenschaften, 76, 578-579 (1989).
10. Julia, M., Julia, S., and Guegan, R., Preparation de composes terpeniques ed t apparentes, a partir de methyl cyclopropyl cetone. Bull. Chim. Fr., I960, 1072-1079 (1960).
11. Shimizu, N., Tarui, H., Mori, N., Nishida, R., and Kuwahara, Y., (E)-2-(2-Hydroxyethylidene)-6-methyl-5-heptenal (a-acariolal) and (E)-2-(2-hydrox-yethyl)-6-methyl-2,5-heptadienal (b-acariolal), two new types of isomeric monoterpenes from Caloglyphus polyphyllae (Acari: Acaridae). Biosci. Biotechnol. Biochem., 67, 308-313 (2003).
12. Jallali-Naini, M., Boussac, G., Lemaitre, P., Larche-veque, M., Guillerm, D., and Lallemand, J.-Y., Efficient total synthesis of polygodial and drimenin. Tetrahedron Lett., 22, 2995-2998 (1981).
13. Dess, D. B., and Martin, J. C., A useful 12-I-5 tria-cetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species. J. Am. Chem. Soc., 113, 7277-7287 (1991).
14. Ireland, R. E., and Liu, L., An improved procedure for the preparation of the Dess-Martin periodinane. J. Org. Chem., 58, 2899 (1993).
15. Frigerio, M., Santagostino, M., and Sputore, S., A user-friendly entry to 2-iodoxybenzoic acid (IBX). J. Org. Chem., 64, 4537-4538 (1999).
16. Bestmann, H. J., Stransky, W., and Vostrowsky, O., Reaktionen mit phosphinalkylenen, XXXIII. Darstellung lithiumsalzfreier ylidlosungen mit natrium-bis(trimethylsilyl)amide als base. Chem. Ber., 109, 1694-1700 (1976).
17. Shimizu, N., Mori, N., and Kuwahara, Y., Identification of a new hydrocarbon (Z, Z)-1,6,9-hep-tadecatriene as the secretory component of Caloglyphus polyphyllae (Astigmata: Acaridae). Biosci. Biotechnol. Biochem., 63, 1478-1480 (1999).
18. Matsumoto, K., Studies on the environmental factors for the breeding of grain mites, VI. Digestive enzymes of the grain mites Carpoglyphus lactis, Aleuroglyphus ovatus and Tyrophagus dimidiatus. Jap. J. Sanit. Zool., 16, 86-89 (1965)