Introduction 1990 2007 Philanthus triangulum 1999 1990 1997 1999 1992 1996 1994 1995 1998 1995 1998 1999 2001 1999 2000 2006 2001 2007 2007a 2001 1994 1995 2001 2007a 2007 2007b 2006 Despite the advanced understanding of the function of the secretion of the PPG of female European beewolves, there has been no detailed investigation of its chemistry. Therefore, we analyzed the chemical composition by using combined gas chromatography-mass spectrometry (GC-MS), gas chromatography-Fourier transform infrared spectroscopy (GC-FTIR), fractionation, and derivatizations. Materials and Methods Sampling 2 2007 n 2007b Identification 1985 1994 1998 -1 -1 Data Handling and Statistical Analysis 1986 Z ij 10 Y ij Y j Z ij i j, Y ij i j g Y j j 2004 Results Identification and Analysis of Hydrocarbons in the PPG 1 1 N Z Z Z -1 cis 1994 Fig. 1 Philanthus triangulum a Z b Z 1 1  Table 1 Philanthus triangulum Peak no. RI Compound name Diagnostic MS ions 1 1400 a 198 2 1500 a 212 3 1600 a 226 4 1700 a 240 5 1710 X-Methylheptadecane – 6 1800 a 254 7 1814 X-Methyloctadecane – 8 1900 a 268 9 1906 Sesquiterpene 41, 69, 81, 93, 107, 120, 133, 222 10 2000 a 282 11 2080 Z a 222, 264, 296 12 2100 a 296 13 2200 a 310 14 2267 Δ-X-Tricosene 322 15 2273 Z a 322 16 2286 Δ-7-Tricosene 322 17 2300 a 324 18 2338 11-; 9-Methyltricosane 168/169, 196/197; 140/141, 224/225 19 2343 7-Methyltricosane 112/113, 252/253 20 2352 5-Methyltricosane 84/85, 280/281 21 2371 Δ-X-Tetracosene 336 22 2400 a 338 23 2436 Δ-14-Tricosen-6-one 99, 115, 127, 181, 265, 336 24 2464 Δ,Δ-X,Y-Pentacosadiene 348 25 2471 Z a 350 26 2492 Δ-Pentacosene 350 27 2500 a 352 28 2537 13-; 11-; 9-Methylpentacosane 196/197; 168/169, 224/225; 140/141, 252/253 29 2538 Δ-15-Tetracosen-7-one 94, 113, 141, 181, 195, 265, 350 30 2543 7- Methylpentacosane 112/113, 280/281 31 2554 Δ-16-Pentacosen-8-ol 67, 348 32 2572 Z 364 33 2600 a 366 34 2639 Δ-16-Pentacosen-8-one 127, 155, 195, 209, 265, 364 35 2668 Pentacosan-8-one 127, 143, 155, 267, 283, 366 36 2672 Z a 378 37 2700 a 380 38 2714 NI – 39 2735 13-; 11-; 9-Methylheptacosane 196/197, 224/225; 168/169, 252/253; 140/141, 280/281 40 2740 Δ-17-Heptacosen-9-one 141, 169, 209, 223, 265, 378 41 2800 a 394 42 2840 Δ-18-Heptacosen-10-one 155, 171, 183, 223, 237, 265, 392 43 2868 Heptacosan-10-one 127, 143, 155, 171, 267, 283, 295, 394 44 2872 Z 406 45 2900 a 408 46 2933 15-; 13-; 11-Methylnonacosane 224/225; 196/197, 252/253; 168/169, 280/281 47 3000 a 422 48 3076 Z 434 49 3100 a 436 50 3134 15-; 13-Methylhentriacontane 224/225, 252/253; 196/197, 280/281 51 3200 a 450 52 3275 Z 462 53 3300 a 464 RI X Y Δ NI a Identification of the Constituents in the Polar Fraction 2 1998 2003 m/z m/z 9 19 + m/z 17 33 + m/z 9 19 + 17 35 + + 2003 m/z 6 11 + 17 33 + + 2001 1998 1 Z Chemical Dimorphism 2 2 Z Z 2 df P 2 Fig. 2 N Philanthus triangulum Z 1986 Z ij 10 Y ij Y j Z ij i j, Y ij i j g Y j j Z  Table 2 P. triangulum Z Z a Compound name C25-type C27-type b P 1 Mean SD Mean SD Pent-Hept Heneicosane (12) 0.20 0.14 0.18 0.13 0.02 0.086 Docosane (13) 0.16 0.09 0.13 0.08 0.04 0.001 Tricosenes (14, 15, 16) 0.36 0.27 0.08 0.07 0.28 <0.001 Tricosane (17) 14.06 3.74 12.93 3.02 1.13 0.003 Methyltricosanes (18, 19, 20) 0.10 0.10 0.05 0.04 0.05 0.003 Tetracosene (21) 1.19 0.65 0.14 0.08 1.06 <0.001 Tetracosane (22) 0.17 0.10 0.14 0.07 0.02 0.003 Pentacosenes (25, 26) 77.48 7.96 8.29 5.50 69.19 <0.001 Pentacosane (27) 2.05 0.92 2.82 1.20 −0.78 0.335 Methylpentacosanes (28) 0.06 0.03 0.08 0.03 −0.02 0.704 Hexacosene (32) 0.13 0.05 1.62 0.72 −1.50 <0.001 Hexacosane (33) 0.05 0.03 0.05 0.02 0.00 0.067 16-Pentacosen-8-one (34) 1.13 0.73 0.25 0.15 0.88 <0.001 Heptacosene (36) 1.00 0.39 69.80 8.86 −68.80 <0.001 Heptacosane (37) 0.38 0.22 0.31 0.12 0.07 0.032 Octacosane (41) 0.03 0.03 0.03 0.02 0.00 0.182 18-Heptacosen-10-one (42) 1.02 5.18 1.73 0.75 −0.70 <0.001 Nonacosene (44) 0.04 0.06 0.95 0.43 −0.90 <0.001 Nonacosane (45) 0.30 0.30 0.32 0.11 −0.02 0.550 Hentriacontene (48) 0.01 0.04 0.04 0.02 −0.03 <0.001 Hentriacontane (49) 0.07 0.08 0.06 0.02 0.01 0.062 a N N P b Discussion The PPG secretion of beewolf females contains predominantly unbranched unsaturated long chain hydrocarbons (C23–C33, mainly either C25 or C27), smaller amounts of saturated hydrocarbons (C14–C33), and small or trace amounts of methylalkanes (C17–C31), unsaturated ketones (C23–C27), saturated ketones (C25, C27), a sesquiterpene, an unsaturated C18 methylester, and an unsaturated C25 alcohol. 2007 2001 2007a 2007 2007 2007a b 1982 2005 2007 1978 1996 2002 2003 2004 2003 1995 1998 Z Anoplophora malasiaca 2003 2007a 2003 2006 2007a 1997 2007 1999 2000 2002 Z Z 2002 2003 Z Z Z 1998 2000 2008 2001 2008 2003 2006 1972 1988 1995 2000 2003 2006 2005 2006 2006 2006 P. triangulum 2007