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
Embrapa Genetic Resources and Biotechnology, Cx. Postal: 02372, Cep.: 70849-970, Brasília, DF, Brazil.
J Chem Ecol. 2006 Dec;32(12):2749-61. doi: 10.1007/s10886-006-9197-6.
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-(1',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.
报道了巴西稻茎蝽Tibraca limbativentris雄性产生的性信息素。对性成熟的雄性和雌性进行的嗅觉仪生物测定表明，雄性吸引雌性，这表明雄性释放性信息素。雄性对任何性别都没有吸引力，雌性对同种雌性也没有吸引力。雌性对雄性的吸引力在夜间最高。通过气相色谱（GC）和GC-质谱对从雄性和雌性虫子收集的顶空挥发物进行了分析。鉴定出两种雄性特异性化合物为1'S-姜烯醇的异构体，而在两性提取物中均鉴定出一系列防御性化合物。姜烯醇有三个手性中心，所采用的非选择性合成产生了两组异构体，姜烯醇I包含四种异构体，即(1RS,4RS,1'R)-4-(1',5'-二甲基己-4'-烯基)-1-甲基环己-2-烯-1-醇，姜烯醇II包含另外四种异构体，即(1RS,4RS,1'S)-4-(1',5'-二甲基己-4'-烯基)-1-甲基环己-2-烯-1-醇。两组立体异构体都比己烷对照更具吸引力。昆虫产生的信息素成分的绝对构型仍有待阐明，但至少有一种异构体确定为1'S立体化学。
