Bombykol

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]

Bombykol

Names
Preferred IUPAC name (10E,12Z)-Hexadeca-10,12-dien-1-ol
Identifiers
CAS Number	765-17-3 Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:41200 Y
ChemSpider	392860 Y
PubChem CID	445128
UNII	LZT8R8TVZ7 Y
CompTox Dashboard (EPA)	DTXSID00894769
InChI 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+ Y Key: CIVIWCVVOFNUST-SCFJQAPRSA-N Y 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
SMILES CCC/C=C\C=C\CCCCCCCCCO OCCCCCCCCC\C=C\C=C/CCC
Properties
Chemical formula	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). Y verify (what is YN ?) Infobox references

Biosynthesis of bombykol starting from palmitoyl-CoA

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][10]

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. Bibcode:1984AppEZ..19..400K. 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. Bibcode:1984AppEZ..19..265K. 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: 71–83. doi:10.1515/bchm2.1961.324.1.71. PMID 13689417.
4. "Molecule of the Week". American Chemical Society. 2004. Archived from the original on August 7, 2004. Retrieved March 2, 2013.
5. Leal, Walter S. (2005). "Pheromone Reception". In Schulz, Stefan (ed.). The Chemistry of Pheromones and Other Semiochemicals II. Topics in Current Chemistry. Vol. 240. Springer. pp. 1–36. doi:10.1007/b98314. 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. doi:10.1271/bbb1961.52.473.
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". Proceedings of the National Academy of Sciences. 101 (23): 8631–6. Bibcode:2004PNAS..101.8631M. doi:10.1073/pnas.0402056101. PMC 423246. PMID 15173596.
9. Zhang, SD; Li, X; Bin, Z; Du, MF; Yin, XM; An, SH (2014). "Molecular identification of a pancreatic lipase-like gene involved in sex pheromone biosynthesis of Bombyx mori". Insect Science. 21 (4): 459–68. Bibcode:2014InsSc..21..459Z. doi:10.1111/1744-7917.12053. PMID 23955937. S2CID 23364842.
10. 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". Frontiers in Endocrinology. 2: 92. doi:10.3389/fendo.2011.00092. PMC 3355880. PMID 22649392.
11. Matsumoto, S; Ozawa, R; Uchiumi, K; Kurihara, M (1996). "Cell-free production of the silkworm sex pheromone bombykol". Bioscience, Biotechnology, and Biochemistry. 60 (2): 369–73. doi:10.1271/bbb.60.369. PMID 9063992.