Sex attractant pheromone from the rice stalk stink bug, Tibraca limbativentris stal
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- Authors:
- BORGES, Miguel
BIRKETT, Michael
ALDRICH, Jeffrey R
OLIVER, James E
CHIBA, Mitsuo
MURATA, Yasuhiro
LAUMANN, Raul A
BARRIGOSSI, José Alexandre
PICKETT, John A
MORAES, Maria C. B - Author Affiliations:
- Embrapa Genetic Resources and Biotechnology, Cx. Postal: 02372, Cep.: 70849-970, Brasília, DF, Brazil
Biological Chemistry Division, Rothamsted Research, Harpenden, Herts AL5 2JQ, United Kingdom
USDA-ARS Chemicals Affecting Insect Behavior Laboratory, BARC-West, B-007, Room 301, 10300 Baltimore Avenue, Beltsville, MD 20705, United States
Fuji Flavor Co. Ltd., 3-5-8 Midorigaoka, Hamura City, Tokyo 205-8503, Japan
Embrapa Rice and Beans, Cx. Postal: 179, Cep.: 75375-000, Goiânia, GO, Brazil - Source:
- Journal of chemical ecology. 32(12):2749-2761
- Publication Date:
- 2006-01-01
- Language:
- English
- Abstract:
- The male-produced sex pheromone from the Brazilian rice stalk stink bug Tibraca limbativentris is reported. Olfactometer bioassays with sexually mature males and females showed that males attracted females, which suggests that males release a sex pheromone. Males were not attracted to either sex, nor were females attractive to conspecific females. Attraction of the females to males was highest at night. The headspace volatiles collected from male and female bugs were analyzed by gas chromatography (GC) and GC-mass spectrometry. Two male-specific compounds were identified as isomers of 1 'S'-zingiberenol, whereas a series of defensive compounds were identified in extracts from both sexes. Zingiberenol has three chiral centers, and the nonselective syntheses used produced two groups of isomers, zingiberenol I containing four isomers, namely (1RS,4RS, 1 'R)-4-( 1 ',5'-dimethylhex-4'-enyl)-1-methylcyclohex-2-en-1-ol, and zingiberenol II containing the other four isomers, namely (1RS,4RS,1'S)-4-(l',5'-dimethylhex-4'-enyl)-1-methylcyclohex-2-en-1-ol. Both groups of stereoisomers were more attractive than hexane controls. The absolute configuration of the insect-produced pheromonal components remains to be elucidated, but the 1'S' stereochemistry was established for at least one of the isomers.
- Notes:
- Animal, vegetal and microbial ecology
- Subjects:
- Ecology
Ecologie
Environment
Environnement
Sciences biologiques et medicales
Biological and medical sciences
Sciences biologiques fondamentales et appliquees. Psychologie
Fundamental and applied biological sciences. Psychology
Ecologie animale, vegetale et microbienne
Animal, plant and microbial ecology
Ecologie animale et végétale
Animal and plant ecology
Autoécologie
Autoecology
Animaux
Animals
Protozoa. Invertebrata
Arthropoda
Composé sémiochimique
Semiochemicals
Heteroptera
Insecta
Invertebrata
Pentatomidae
Allomone
Alomona
Analyse chimique
Chemical analysis
Análisis químico
Attractif
Attractant
Atractivo
Mâle
Male
Macho
Phéromone sexuelle
Sex pheromone
Feromona sexual
Structure chimique
Chemical structure
Estructura química
Tibraca limbativentris
(1RS, 4RS, 1'5)-4-(1', 5'-dimethylhex-4'-enyl)- 1-methylcyclohex-2-en-1-ol
Semiochemical
allomone
zingiberenol - Format:
- Academic Journal
- Database:
- PASCAL Archive
- Journal:
- Journal of chemical ecology
- Volume:
- 32
- Issue:
- 12
- Page Start:
- 2749
- Page Count:
- 13
- ISSN:
- 00980331
- Publisher:
- New York, NY: Springer, 2006.
- Document Type:
- Article
- Physical Description:
- print, 1 p.1/4
