[en] The Chinese tussah silkworm, Antheraea pernyi (Lepidoptera: Saturniidae) produces a rare dienoic sex pheromone composed of (E,Z)-6,11-hexadecadienal, (E,Z)-6,11-hexadecadienyl acetate and (E,Z)-4,9-tetradecadienyl acetate, and for which the biosynthetic routes are yet unresolved. By means of gland composition analyses and in vivo labeling we evidenced that pheromone biosynthesis towards the immediate dienoic gland precursor, the (E,Z)-6,11-hexadecadienoic acid, involves desaturation steps with Δ(6) and Δ(11) regioselectivity. cDNA cloning of pheromone gland desaturases and heterologous expression in yeast demonstrated that the 6,11-dienoic pheromone is generated from two biosynthetic routes implicating a Δ(6) and Δ(11) desaturase duo albeit with an inverted reaction order. The two desaturases first catalyze the formation of the (E)-6-hexadecenoic acid or (Z)-11-hexadecenoic acid, key mono-unsaturated biosynthetic intermediates. Subsequently, each enzyme is able to produce the (E,Z)-6,11-hexadecadienoic acid by accommodating its non-respective mono-unsaturated product. Besides elucidating an unusually flexible pheromone biosynthetic pathway, our data provide the first identification of a biosynthetic Δ(6) desaturase involved in insect mate communication. The occurrence of this novel Δ(6) desaturase function is consistent with an evolutionary scenario involving neo-functionalization of an ancestral desaturase belonging to a gene lineage different from the Δ(11) desaturases commonly involved in moth pheromone biosynthesis.
Disciplines :
Biochemistry, biophysics & molecular biology
Author, co-author :
Wang, Hong-Lei ✱; Chemical Ecology and Ecotoxicology, Department of Biology, Lund University, SE-223 62 Lund, Sweden
Lienard, Marjorie ✱; Université de Liège - ULiège > GIGA > GIGA Molecular Biology of Diseases ; Chemical Ecology and Ecotoxicology, Department of Biology, Lund University, SE-223 62 Lund, Sweden
Zhao, Cheng-Hua; State Key Laboratory of Integrated Management of Pest Insects and Rodents, Institute of Zoology, Chinese Academy of Sciences, Beijing 100101, China
Wang, Chen-Zhu; State Key Laboratory of Integrated Management of Pest Insects and Rodents, Institute of Zoology, Chinese Academy of Sciences, Beijing 100101, China
Löfstedt, Christer; Chemical Ecology and Ecotoxicology, Department of Biology, Lund University, SE-223 62 Lund, Sweden
✱ These authors have contributed equally to this work.
Language :
English
Title :
Neofunctionalization in an ancestral insect desaturase lineage led to rare Δ6 pheromone signals in the Chinese tussah silkworm.
The authors are thankful towards Prof. Cai-Hong Wu (Peking University, China) for providing synthetic pheromone standards; Prof. Eric Hedenström and his group (Department of Natural Sciences, Engineering and Mathematics, Sundsvall, Sweden) for synthesizing the E6-16:Me, Prof. Zhong-Ning Zhang and Dr. Chao Che (Institute of Zoology, CAS, China) for assistance with chemical synthesis, Dr. Zeng-Liang Chen (Institute of Zoology, CAS, China) for assistance during insect collection and Jean-Marc Lassance (Department of Biology, Lund University, Sweden) for his advice. This study was financially supported by the Swedish research council (Vetenskapsrådet, project no. 621-2007-5659 ) and VR/SIDA Swedish Research Links (project no. 348-2005-6251 ), the National Basic Research Program of China (grant no. 2006CB102006 ) and the National Natural Science Foundation of China (grant no. 30621003 ).
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