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Neofunctionalization in an ancestral insect desaturase lineage led to rare Delta(6) pheromone signals in the Chinese tussah silkworm

Wang, Hong-Lei LU ; Liénard, Marjorie LU ; Zhao, Cheng-Hua; Wang, Chen-Zhu and Löfstedt, Christer LU (2010) In Insect Biochemistry and Molecular Biology 40. p.742-751
Abstract
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 Delta(6) and Delta(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 Delta(6) and Delta(11)... (More)
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 Delta(6) and Delta(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 Delta(6) and Delta(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 Delta(6) desaturase involved in insect mate communication. The occurrence of this novel Delta(6) desaturase function is consistent with an evolutionary scenario involving neo-functionalization of an ancestral desaturase belonging to a gene lineage different from the Delta11-desaturases commonly involved in moth pheromone biosynthesis. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Insect Biochemistry and Molecular Biology
volume
40
pages
742 - 751
publisher
Elsevier
external identifiers
  • wos:000283390300005
  • scopus:77956995083
ISSN
1879-0240
DOI
10.1016/j.ibmb.2010.07.009
project
Evolutionary mechanisms of pheromone divergence in Lepidoptera
The insect pheromone brewery
language
English
LU publication?
yes
id
7ece67a0-23e4-4e60-b548-b3162d208642 (old id 1665488)
date added to LUP
2010-09-09 14:09:18
date last changed
2018-05-29 12:16:15
@article{7ece67a0-23e4-4e60-b548-b3162d208642,
  abstract     = {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 Delta(6) and Delta(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 Delta(6) and Delta(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 Delta(6) desaturase involved in insect mate communication. The occurrence of this novel Delta(6) desaturase function is consistent with an evolutionary scenario involving neo-functionalization of an ancestral desaturase belonging to a gene lineage different from the Delta11-desaturases commonly involved in moth pheromone biosynthesis.},
  author       = {Wang, Hong-Lei and Liénard, Marjorie and Zhao, Cheng-Hua and Wang, Chen-Zhu and Löfstedt, Christer},
  issn         = {1879-0240},
  language     = {eng},
  pages        = {742--751},
  publisher    = {Elsevier},
  series       = {Insect Biochemistry and Molecular Biology},
  title        = {Neofunctionalization in an ancestral insect desaturase lineage led to rare Delta(6) pheromone signals in the Chinese tussah silkworm},
  url          = {http://dx.doi.org/10.1016/j.ibmb.2010.07.009},
  volume       = {40},
  year         = {2010},
}