Electrophysiological Responses of Bactrocera kraussi (Hardy) (Tephritidae) to Rectal Gland Secretions and Headspace Volatiles Emitted by Conspecific Males and Females
Abstract
:1. Introduction
2. Results
2.1. Analysis of Rectal Gland Extracts and Headspace Collections
2.2. Electrophysiology
3. Discussion
4. Materials and Methods
4.1. Insects
4.2. Rectal Gland Extraction
4.3. Headspace Collection
4.4. Analysis of Rectal Gland Extracts and Headspace Collections
4.5. Synthesis
4.5.1. General Procedure
4.5.2. Synthesis of N-(2-Methylbutyl)acetamide (3)
4.5.3. Synthesis of N-(3-Methylbutyl)acetamide (4)
4.5.4. Synthesis of 2,8-Dimethyl-1,7-dioxaspiro[5.5]undecane
4.5.5. Synthesis of 2-Ethyl-7-methyl-1,6-dioxaspiro[4.5]undecane (6)
4.5.6. Synthesis of 6-Oxanon-1-ol (11)
4.5.7. Synthesis of Propyl Dodecanoiate (15)
4.5.8. Synthesis of Ethyl (Z)-Hexadec-9-enoate (31)
4.5.9. Synthesis of Ethyl (E)-Octadec-9-enoate (34)
4.6. Electrophysiology
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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RI | Name | MW | Characteristic EI ions m/z (%) | FRG (%) | FHS (%) | MRG (%) | MHS (%) |
---|---|---|---|---|---|---|---|
1027 | 2-Ethyl-1-hexanol (1) | 130.2 | 112 (M–H2O, 2.1), 99 (β-cleavage product, 1.1), 98 (6.9), 83 (25.8), 70 (25.9), 69 (10.1), 57 (100), 56 (CH3CH2CH=CH2, 25.3) | ND | ND | 2.3 | 3.4 |
1073 | 2,7-Dimethyl-1,6-dioxaspiro[4.5]decane (2) | 170.1 | 170 (M+, 5.9), 126 (M–C2H4O,18.2), 101 ((C5H7O)=OH, 100), 98 ((C5H7O)=CH2, 90.5), 83 (33.6), 69 (23.6), 57 (28.1), 55 (44.1), 43 (43.0), 41 (25.5) | <1 | ND | <1 | ND |
1124 | N-(2-Methylbutyl)acetamide (3) | 129.1 | 129 (M+, 9.7), 100 (M–C2H5, 34.7), 73 (β-cleavage product, 43.2), 72 (β-cleavage product, 95.6), 60 (CH3C(OH)NH+, 61.3), 43 (100) | ND | ND | <1 | 5.1 |
1131 | N-(3-methylbutyl)acetamide (4) | 129.1 | 129 (M+, 4.5), 114 (M–CH3, 9.7), 86 (M–C3H7, 25.2), 73 (β-cleavage product, 85.7), 72 (β-cleavage product, 72.2), 60 (CH3C(OH)NH+, 36.5), 43 (100) | <1 | <1 | 2.2 | 44.3 |
1145 | (E,E)-2,8-Dimethyl-1,7-dioxaspiro[5.5]undecane (5) | 184.1 | 184 (M+, 8.6), 169 (M–CH3, 1.6), 140 (14.1), 125 (9.7), 115 (CH3(C5H7O)=OH, 92.2), 112 (CH3(C5H7O)=CH2, 100), 97 (73.0), 69 (50.9), 55 (67.0) | 7.6 | <1 | 85.6 | 45.1 |
1157 | 2-Ethyl-7-methyl-1,6-dioxaspiro[4.5]decane isomer 1 (6) | 184.1 | 184 (M+, 3.1), 155 (M–C2H5, 23.1), 140 (7.1), 115 (CH3(C5H7O)=OH, 100), 112 (CH3(C5H7O)=CH2, 60.2), 97 (69.4), 85 (60.5), 69 (48.7), 55 (68.5) | <1 | ND | <1 | ND |
1175 | Diethyl butanedioate (7) | 174.2 | 174 (M+, 0.7), 129 (M–OC2H5, 53.5), 128 (14.1), 101 (M–COOC2H5, 100), 73 (26.0), 74 (13.4), 55(32.6), 45 (18.5), 43 (10.1) | ND | ND | <1 | ND |
1178 | 2-Methyl-6-pentyl-3,4-dihydro-2H-pyran (8) | 168.3 | 168 (22.5), 125 (M–C3H7, 38.2), 112 (C7H12O, 100), 97 (30.2), 84 (19.5), 83 (31.8), 70 (24.6), 55 (65.8) | ND | ND | <1 | ND |
1218 | (E,Z)/(Z,E)-2,8-Dimethyl-1,7-dioxaspiro[5.5]undecane (9) | 184.1 | 184 (M+, 5.8), 169 (M–CH3, 1.8), 140 (5.7), 125 (5.9), 115 (CH3(C5H7O)=OH, 100), 112 (CH3(C5H7O)=CH2, 39.2), 97 (69.8), 69 (39.1), 55 (27.3) | <1 | ND | <1 | ND |
1233 | (E,E)-2-Ethyl-8-methyl-1,7-dioxaspiro[5.5]undecane (10) | 198.2 | 198 (M+, 9.3), 169 (M–C2H5, 11.2), 140 (12.9), 129 (CH3CH2(C5H7O)=OH+, 40.2), 126 (CH3CH2(C5H7O)=CH2, 30.0), 115 CH3(C5H7O)=OH, 87.7), 112 (CH3(C5H7O)=CH2, 83.0), 97 (58.4), 83 (55.5), 69 (67.7), 55 (100) | <1 | <1 | 2.7 | 2.1 |
1240 | 2-Ethyl-7-methyl-1,6-dioxaspiro[4.5]decane isomer 2 (11) | 184.1 | 184 (M+, 5.2), 155 (M–C2H5, 26.1), 140 (9.3), 115 (CH3(C5H7O)=OH, 100), 112 (CH3(C5H7O)=CH2, 49.2), 97 (76.1), 85 (35.7), 69 (49.3), 55 (41.8) | ND | ND | <1 | ND |
1270 | (Z,Z)-2,8-Dimethyl-1,7-dioxaspiro[5.5]undecane (12) | 184.1 | 184 (M+, 4.3), 169 (M–CH3, 2.8), 140 (3.9), 125 (6.5), 115 (CH3(C5H7O)=OH, 100), 112 (CH3(C5H7O)=CH2, 66.5), 97 (31.7), 69 (30.3), 55 (59.0) | <1 | ND | <1 | ND |
1278 | 6-Hexyl-2-methyl-3,4-dihydro-2H-pyran (13) | 182.2 | 182 (M+, 16.8), 125 (M–C4H9, 42.9), 112 (C7H12O, 100), 97 (38.9), 83 (42.9), 70 (31.7), 55 (64.9) | ND | ND | <1 | ND |
1319 | 2-Methyl-8-propyl-1,7-dioxaspiro[5.5]undecane (14) | 212.2 | 212 (M+, 9.0), 169 (M–C3H7, 17.2), 143 (C3H7(C5H7O)=OH+, 32.6), 140 (C3H7(C5H7O)=CH2, 40.5), 125 (M–C5H11O, 47.2), 115 (CH3(C5H7O)=OH, 100), 112 (CH3(C5H7O)=CH2, 78.2) 97 (76.3), 55 (51.4), 43 (49.0) | <1 | ND | <1 | ND |
1336 | 2,8-Dimethyl-1,7-dioxaspiro[5.5]undecan-3-ol (15) | 200.3 | 200 (M+, 3.2), 156 (34.2), 128 (5.9), 112 (CH3(C5H7O)=CH2, 100), 97 (28.6), 83 (31.2), 55 (23.9) | <1 | ND | <1 | ND |
1347 | 6-Oxononan-1-ol (16) | 158.2 | 158 (M+, 0.6), 140 (M–H2O, 1.4), 115 (9.4), 112 (2.9), 99 (3.6), 97 (20.2), 86 (33.1), 79 (9.6), 73 (12.7), 71 (67.1), 69 (64.0), 58 (53.2), 55 (29.9), 43 (100), 41 (66.8) | ND | ND | 4.9 | ND |
1524 | Methyl dodecanoate (17) | 214.2 | 214 (M+, 2.6), 183 (M–OCH3, 3.7), 171 (5.0), 143 (7.0), 129 (4.7), 87 (55.9), 74 (McLafferty rearrangement product, 100), 59 (COOCH3, 10.8), 55 (29.1) | <1 | <1 | ND | ND |
1558 | Dodecanoic acid (18) | 200.3 | 200 (M+, 12.0), 171 (M–C2H5, 12.1), 157 (M–C3H7, 27.3), 129 (M–C5H11, 41.0), 73 (HOCOC2H4, 96.8), 60 (CH3COOH, 100) | <1 | ND | ND | ND |
1594 | Ethyl dodecanoate (19) | 228.4 | 228 (M+, 2.8), 199 (M–C2H5, 1.9), 183 (M–OC2H5, 5.6), 157 (7.6), 101 (35.9), 88 (McLafferty rearrangement product, 100), 73 (COOC2H5, 20.7), 70 (21.8), 61 (14.9), 60 (13.7), 55 (27.0) | 39.1 | 70.2 | ND | ND |
1665 | Ethyl tridecanoate (20) | 242.2 | 242 (M+, 3.4), 213 (M–C2H5, 5.1), 197 (M–OC2H5, 2.1), 199 (12.4), 157 (13.7), 101 (59.3), 88 (McLafferty rearrangement product, 100), 73 (COOC2H5, 26.5), 57 (50.2), 55 (44.7) | <1 | <1 | ND | ND |
1689 | Propyl dodecanoate (21) | 242.2 | 242 (M+, 1.5), 201 (21.9), 199 (M–C3H7, 3.4), 183 (M–OC3H7, 25.8), 157 (6.3), 129 (9.3), 115 (16.9), 102 (McLafferty rearrangement product, 29.3), 87 (COOC3H7, 9.8), 61 (100), 59 (6.1), 55 (33.5) | <1 | <1 | ND | ND |
1725 | Methyl tetradecanoate (22) | 242.2 | 242 (M+, 2.9), 211 (M–OCH3, 1.2), 199 (5.8), 143 (7.5), 125 (7.3), 111 (19.2), 101 (5.0), 97 (32.3), 87 (47.2), 74 (McLafferty rearrangement product, 100), 59 (COOCH3, 8.6), 55 (66.7) | 4.1 | <1 | ND | ND |
1758 | Tetradecanoic acid (23) | 228.4 | 228 (M+, 22.5), 185 (M–C3H7, 32.3), 129 (M–C7H15, 54.7), 73 (HOCOC2H4, 100), 60 (CH3COOH, 94.2) | <1 | ND | ND | ND |
1782 | Ethyl (Z)-tetradec-9-enoate (24) | 254.2 | 254 (M+, 2.5), 209 (M–OC2H5, 6.0), 208 (M–C2H5OH, 7.1), 166 (8.4), 124 (10.3), 88 (McLafferty rearrangement product, 32.8), 73 (COOC2H5, 14.6), 69 (45.4), 55 (100) | <1 | <1 | ND | ND |
1795 | Ethyl tetradecanoate (25) | 256.4 | 256 (M+, 4.4), 211 (M–OC2H5, 6.0), 213 (5.8), 157 (10.1), 101 (46.2), 88 (McLafferty rearrangement product, 100), 73 (COOC2H5, 21.8), 70 (22.7), 55 (32.2) | 25.6 | 23.7 | ND | ND |
1846 | 3-Methylbutyl dodecanoate (26) | 270.5 | 270 (M+, 1.0), 201 (1.5), 183 (M–OC5H11, 4.3), 115 (COOC5H11, 2.0), 70 (100), 71(34.9), 55 (18.9), 43 (46.4) | <1 | <1 | ND | ND |
1906 | Methyl (Z)-hexadec-9-enoate (27) | 268.4 | 268 (M+, 3.5), 237 (M–OCH3, 9.1), 236 (M–CH3OH, 12.8), 194 (12.2), 152 (11.0), 96 (33.3), 74 (McLafferty rearrangement product, 53.7), 59 (COOCH3, 19.9), 55 (100) | <1 | ND | ND | ND |
1926 | Methyl hexadecanoate (28) | 270.3 | 270 (M+, 1.7), 227 (1.7), 143 (9.8), 87 (36.9), 74 (McLafferty rearrangement product, 100), 59 (COOCH3, 9.3), 55 (81.1) | <1 | ND | ND | ND |
1944 | (Z)-Hexadec-9-enoic acid (29) | 254.4 | 254 (M+, 3.2), 237 (M–OH, 3.7), 236 (M–OH2, 18.6), 194 (6.9), 152 (9.5), 97 (54.2), 55 (100) | <1 | ND | ND | ND |
1962 | Hexadecanoic acid (30) | 256.4 | 256 (M+, 22.5), 157 (M–C3H7, 30.7), 185 (M–C5H11, 22.2), 157 (M–C7H15, 22.1), 129 (M–C9H19, 52.1), 73 (HOCOC2H4, 100), 60 (CH3COOH, 91.1) | <1 | ND | ND | ND |
1975 | Ethyl (Z)-hexadec-9-enoate (31) | 282.3 | 282 (M+, 1.9), 237 (M–OC2H5, 10.1), 236 (M–C2H5OH, 10.7), 194 (10.0), 152 (8.8), 88 (McLafferty rearrangement product, 39.0), 73 (COOC2H5, 29.9), 69 (67.0), 55 (100) | 8.7 | <1 | ND | ND |
1984 | Ethyl (E)-hexadec-9-enoate (32) | 282.3 | 282 (M+, 6.8), 237 (M–OC2H5, 21.5), 236 (M–C2H5OH, 25.7), 194 (22.7), 152 (21.9), 88 (McLafferty rearrangement product, 100), 73 (COOC2H5, 15.5), 69 (26.2), 55 (100) | <1 | ND | ND | ND |
1994 | Ethyl hexadecanoate (33) | 284.3 | 284 (M+, 4.2), 241 (4.8), 157 (9.5), 101 (50.9), 255 (M–C2H5, 1.1), 239 (M–OC2H5, 3.9), 88 (McLafferty rearrangement product, 100), 73 (COOC2H5, 21.3), 55 (41.3), 43 (54.4) | 8.9 | <1 | ND | ND |
2141 | (Z)-Octadec-9-enoic acid (34) | 282.5 | 282 (M+, 2.9), 264 (M–OH, 16.7), 222 (6.7), 97 (67.1), 55 (100) | <1 | ND | ND | ND |
2170 | Ethyl (E)-octadec-9-enoate (35) | 310.3 | 310 (M+, 0.6), 265 (M–OC2H5, 6.8), 264 (M–C2H5OH, 10.0), 222 (7.3), 180 (7.1), 123 (9.5), 110 (16.7), 97 (38.5), 88 (McLafferty rearrangement product, 33.2), 83 (44.4), 73 (COOC2H5, 13.6), 69 (65.4), 55 (100), 43 (60.7), 41 (84.3) | 3.1 | ND | ND | ND |
2176 | Ethyl (Z)-octadec-9-enoate (36) | 310.3 | 310 (M+, 1.9), 265 (M–OC2H5, 5.4), 264 (M–C2H5OH, 8.3), 222 (7.1), 180 (7.2), 123 (7.9), 110 (12.5), 97 (37.4), 88 (McLafferty rearrangement product, 25.6), 83 (42.3), 73 (COOC2H5, 11.2), 69 (71.6), 55 (100), 43 (50.2), 41 (71.5) | 2.5 | ND | ND | ND |
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Noushini, S.; Park, S.J.; Perez, J.; Holgate, D.; Mendez, V.; Jamie, I.M.; Jamie, J.F.; Taylor, P.W. Electrophysiological Responses of Bactrocera kraussi (Hardy) (Tephritidae) to Rectal Gland Secretions and Headspace Volatiles Emitted by Conspecific Males and Females. Molecules 2021, 26, 5024. https://doi.org/10.3390/molecules26165024
Noushini S, Park SJ, Perez J, Holgate D, Mendez V, Jamie IM, Jamie JF, Taylor PW. Electrophysiological Responses of Bactrocera kraussi (Hardy) (Tephritidae) to Rectal Gland Secretions and Headspace Volatiles Emitted by Conspecific Males and Females. Molecules. 2021; 26(16):5024. https://doi.org/10.3390/molecules26165024
Chicago/Turabian StyleNoushini, Sally, Soo Jean Park, Jeanneth Perez, Danielle Holgate, Vivian Mendez, Ian M. Jamie, Joanne F. Jamie, and Phillip W. Taylor. 2021. "Electrophysiological Responses of Bactrocera kraussi (Hardy) (Tephritidae) to Rectal Gland Secretions and Headspace Volatiles Emitted by Conspecific Males and Females" Molecules 26, no. 16: 5024. https://doi.org/10.3390/molecules26165024