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Bombykol

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Bombykol
Names
IUPAC name
(10E,12Z)-hexadeca-10,12-dien-1-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C16H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h4-7,17H,2-3,8-16H2,1H3/b5-4-,7-6+ checkY
    Key: CIVIWCVVOFNUST-SCFJQAPRSA-N checkY
  • InChI=1/C16H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h4-7,17H,2-3,8-16H2,1H3/b5-4-,7-6+
    Key: CIVIWCVVOFNUST-SCFJQAPRBG
  • CCC/C=C\C=C\CCCCCCCCCO
  • OCCCCCCCCC\C=C\C=C/CCC
Properties
C16H30O
Molar mass 238.415 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Bombykol is a pheromone released by the female silkworm moth to attract mates. It is also the sex pheromone in the wild silk moth (Bombyx mandarina).[1][2] Discovered by Adolf Butenandt in 1959, it was the first pheromone to be characterized chemically.[3] Minute quantities of this pheromone can be used per acre of land to confuse male insects about the location of their female partners. It can thus serve as a lure in traps to remove insects effectively without spraying crops with large amounts of pesticides. Butenandt named the substance after the moth's Latin name Bombyx mori.[4]

In vivo it appears that bombykol is the natural ligand for a pheromone binding protein, BmorPBP, which escorts the pheromone to the pheromone receptor.[5]

Biosynthesis

Bombykol is known to be derived from acetyl-CoA via the C-16 fatty acyl palmitoyl-CoA.[6] Palmitoyl-CoA is converted to bombykol in steps that involve desaturation and reductive modification of the carbonyl carbon.[7] Compared to other Type I pheromones, bombykol biosynthesis does not need chain-shortening or any other kind of modification of the terminal hydroxyl group.

A desaturase enzyme encoded by the gene Bmpgdesat1 (Desat1), produces the monoene (11Z)-hexadecenoyl-CoA as well as the diene (10E,12Z)-10,12-hexadecadienoyl-CoA. This desaturase is the only enzyme necessary to catalyze these two consecutive desaturation steps.[8]

The bombykol acyl precursor (10E,12Z)-10,12-hexadecadienoate is primarily found as a triacylglycerol ester in the cytoplasmic lipid droplets of pheromone gland cells of the moth. And when the adult females emerge from their pupae, the neurohormone PBAN (pheromone biosynthesis-activating neuropeptide) start signaling events that help control the lipolysis of the stored triacylglycerols, releasing (10E,12Z)-10,12-hexadecadienoate for its final reductive modification.[9][10][11] The mechanism of the lipolytic release of (10E,12Z)-10,12-hexadecadienoate from triacylglycerols is not completely known but the candidate lipase-encoding genes have been identified.[9][12]

Biosynthesis of bombykol starting from palmitoyl-CoA

References

  1. ^ Kuwahara, Yasumasa (1984). "Flight Time of Bombyx mandarina Males to a Pheromone Trap Baited with Bombykol". Applied Entomology and Zoology. 19 (3): 400–401. doi:10.1303/aez.19.400.
  2. ^ Kuwahara, Yasumasa; Mori, Naoki; Yamada, Shigeki; Nemoto, Tadashi (1984). "Evaluation of Bombykol as the Sex Pheromone of Bombyx mandarina(Lepidoptera : Bombycidae)". Applied Entomology and Zoology. 19 (2): 265–267. doi:10.1303/aez.19.265.
  3. ^ Butenandt, A.; Beckamnn, R.; Hecker, E. (1961). "Über den Sexuallockstoff des Seidenspinners .1. Der biologische Test und die Isolierung des reinen Sexuallockstoffes Bombykol". Hoppe-Seyler's Zeitschrift für Physiologische Chemie. 324: 71. doi:10.1515/bchm2.1961.324.1.71.
  4. ^ "Molecule of the Week". American Chemical Society. 2004. Archived from the original on August 7, 2004. Retrieved March 2, 2013. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  5. ^ Leal, Walter S. (2005). "Pheromone Reception". In Schulz, Stefan (ed.). The Chemistry of Pheromones and Other Semiochemicals II. Springer. ISBN 9783540213086. Retrieved March 2, 2013.
  6. ^ Caspi et al, Nucleic Acids Research 42:D459-D471 2014.
  7. ^ Ando T, Hase T, Arima R, Uchiyama M (1988). "Biosynthetic pathway of bombykol, the sex pheromone of the female silkworm moth." Agricultural and Biological Chemistry 52(2);473-478.
  8. ^ Moto K, Suzuki MG, Hull JJ, Kurata R, Takahashi S, Yamamoto M, Okano K, Imai K, Ando T, Matsumoto S (2004). "Involvement of a bifunctional fatty-acyl desaturase in the biosynthesis of the silkmoth, Bombyx mori, sex pheromone." Proc Natl Acad Sci U S A 101(23);8631-6. PMID 15173596.
  9. ^ a b Zhang S, Li X, Bin Z, Du M, Yin X, An S (2013). "Molecular identification of a pancreatic lipase-like gene involved in sex pheromone biosynthesis of Bombyx mori." Insect Sci. PMID 23955937.
  10. ^ Ohnishi11: Ohnishi A, Kaji M, Hashimoto K, Matsumoto S (2011). "Screening for the Genes Involved in Bombykol Biosynthesis: Identification and Functional Characterization of Bombyx mori Acyl Carrier Protein." Front Endocrinol (Lausanne) 2;92. PMID 22649392.
  11. ^ Matsumoto S, Ozawa R, Uchiumi K, Kurihara M (1996). "Cell-free production of the silkworm sex pheromone bombykol." Biosci Biotechnol Biochem 60(2);369-73. PMID 9063992.
  12. ^ Ohnishi A, Kaji M, Hashimoto K, Matsumoto S (2011). "Screening for the Genes Involved in Bombykol Biosynthesis: Identification and Functional Characterization of Bombyx mori Acyl Carrier Protein." Front Endocrinol (Lausanne) 2;92. PMID 22649392
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