Parcoblattalactone.

NMR of compound 1 purified from an extract of the sex pheromone glands of P. lata virgin females. (Top) Olefinic region (Left) and homo decoupling experiment with both sets of protons 6 and 10 decoupled simultaneously (Right). (Middle) Natural compound, (Bottom) Synthetic parcoblattalactone.

Unusual macrocyclic lactone sex pheromone of Parcoblatta lata, a primary food source of the endangered red-cockaded woodpecker

1. Dorit Eliyahua,b12, 
2. Satoshi Nojimaa,b13, 
3. Richard G. Santangeloa,b, 
4. Shannon Carpenterc4,
5. Francis X. Websterc, 
6. David J. Kiemlec, 
7. Cesar Gemenoa,b5, 
8. Walter S. Leald, and 
9. Coby Schala,b,6

Author Affiliations

1. aDepartment of Entomology and
2. bW. M. Keck Center for Behavioral Biology, North Carolina State University, Raleigh, NC 27695;
3. cDepartment of Chemistry, College of Environmental Science and Forestry, State University of New York, Syracuse, NY 13210; and
4. dDepartment of Entomology, University of California, Davis, CA 95616
5. E-mail: coby_schal@ncsu.edu.

http://www.pnas.org/content/109/8/E490

(Z,Z)-3,10-Dodecadienolide
Formula:	C12H18O2
CAS#:
MW:	194.27

Parcoblattalactone is a macrocyclic lactone deriving from a 12-carbon fatty acid hydroxylated in position w. This compound is a sex pheromone of the insectParcoblatta lata, which represents the most abundant arthropod biomass in the pine forests of the southeastern United States (Eliyahu D et al., PNAS, 2012, 109, 490-6). This pheromone will be used for monitoring populations of insects that comprise an important food source for endangered bird species.

Parcoblattalactone

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Fig. 2.

Identification of ascr#1 and dhas#18 as sex pheromones in P. redivivus. (A) Activity-guided fractionation of P. redivivus WW. (B) 1H NMR spectra of isolated natural dhas#18 (red), synthetic dhas#18 (green), and a mixture of natural and synthetic samples (blue). (C) dqf-COSY spectrum of isolated dhas#18. (D) Section of the dqf-COSY spectrum in C showing cross-peaks diagnostic of the ascarylose ring (black boxes) and the highly functionalized side chain (yellow boxes). (E) Synthesis of dhas#18. a, 1. TiCl4, 2. allylSn(PPh3); b, vinylmagnesium bromide, Me2S-CuBr, tetrahydrofuran (THF); c, BzCl, pyridine; d, t-butyldimethylsilyl chloride (TBDMSCl), imdidazole, dichloromethane (DCM); e, Grubbs II, 1,4-benzochinone, DCM; f, H2, Pd/C, EtOH; g, trimethylsilyl triflate (TMSOTf), DCM; h, aqueous LiOH, THF, dioxane.

http://www.pnas.org/content/109/51/20949.long

Nematodes use an extensive chemical language based on glycosides of the dideoxysugar ascarylose for developmental regulation (dauer formation), male sex attraction, aggregation, and dispersal. However, no examples of a female- or hermaphrodite-specific sex attractant have been identified to date. In this study, we investigated the pheromone system of the gonochoristic sour paste nematode Panagrellus redivivus, which produces sex-specific attractants of the opposite sex. Activity-guided fractionation of the P. redivivusexometabolome revealed that males are strongly attracted to ascr#1 (also known as daumone), an ascaroside previously identified from Caenorhabditis elegans hermaphrodites. Female P. redivivus are repelled by high concentrations of ascr#1 but are specifically attracted to a previously unknown ascaroside that we named dhas#18, a dihydroxy derivative of the known ascr#18 and an ascaroside that features extensive functionalization of the lipid-derived side chain. Targeted profiling of the P. redivivusexometabolome revealed several additional ascarosides that did not induce strong chemotaxis. We show that P. redivivus females, but not males, produce the male-attracting ascr#1, whereas males, but not females, produce the female-attracting dhas#18. These results show that ascaroside biosynthesis in P. redivivus is highly sex-specific. Furthermore, the extensive side chain functionalization in dhas#18, which is reminiscent of polyketide-derived natural products, indicates unanticipated biosynthetic capabilities in nematodes.

Sex-specific mating pheromones in the nematodePanagrellus redivivus

1. Andrea Choea,1, 
2. Tatsuji Chumanb,1, 
3. Stephan H. von Reussc,1,2, 
4. Aaron T. Dosseyb,1,3, 
5. Joshua J. Yimc,
6. Ramadan Ajredinib, 
7. Adam A. Kolawaa, 
8. Fatma Kapland,4, 
9. Hans T. Albornd, 
10. Peter E. A. Teald,
11. Frank C. Schroederc, 
12. Paul W. Sternberga,5, and 
13. Arthur S. Edisonb,5

Author Affiliations

1. aThe Howard Hughes Medical Institute and Biology Division, California Institute of Technology, Pasadena, CA 91125;
2. bDepartment of Biochemistry and Molecular Biology and National High Magnetic Field Laboratory, University of Florida, Gainesville, FL 32610-0245;
3. cBoyce Thompson Institute and Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY 14853; and
4. dCenter for Medical, Agricultural and Veterinary Entomology, US Department of Agriculture—Agricultural Research Service, Gainesville, FL 32608

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