Sequestration of 3-oxygenated α-ionone derivatives in the male rectal gland of the solanaceous fruit fly, Bactrocera latifrons

Entomologia Experimentalis et Applicata

Volumn 131, Issue 1, 2009, Pages 85-92

  Nishida, Ritsuo ^a   Enomoto, Hiroshi ^a   Shelly, Todd E ^b   Ishida, Tatsuaki ^c  

^a KYOTO UNIVERSITY   (Japan)

^b UNITED STATES DEPARTMENT OF AGRICULTURE   (United States)

^c NATIONAL VETERINARY ASSAY LABORATORY   (Japan)

Author keywords

ionone analog; 3 hydroxy ionone; 3 oxo ionol; Biotransformation; Diptera; Eggplant; Male attractant; Phagostimulant; Pheromone; Solanaceae; Tephritidae

Indexed keywords

BIOTRANSFORMATION; CONSPECIFIC; CULTIVAR; DICOTYLEDON; FEEDING BEHAVIOR; FLY; SEX PHEROMONE;

BACTROCERA LATIFRONS; CAPSICUM FRUTESCENS; DIPTERA; MAGNOLIOPHYTA; SOLANACEAE; SOLANUM MELONGENA; TEPHRITIDAE;

EID: 61849136598     PISSN: 00138703     EISSN: 15707458     Source Type: Journal    
DOI: 10.1111/j.1570-7458.2009.00835.x     Document Type: Article

References (42)

1. Aubert C, Ambid C, Baumes R Guenata Z (2003) Investigation of bound aroma constituents of yellow-fleshed nectarines (Prunus persica L. cv. Springbright). Changes in bound aroma profile during maturation. Journal of Agricultural and Food Chemistry 51 : 6280 6286.
2. Avery JW, Liquido N, Cunningham RT, Leonhardt BA Waters ILM (1996) Volatile components of rectal glands of the Malaysian fruit fly Bactrocera latifrons (Diptera: Tephritidae). Journal of the American Chemical Society 211 : 102.
3. Boulanger R Crouzet J (2001) Identification of the aroma components of acerola (Malphigia glabra L.): free and bound flavour compounds. Food Chemistry 74 : 209 216.
4. Cutillo F, D'Abrosca B, DellaGreca M, Fiorentino A Zarrelli A (2006) Terpenoids and phenol derivatives from Malva silvestris. Phytochemistry 67 : 481 485.
5. D'Abrosca B, DellaGreca M, Fiorentino A, Monaco P, Oriano P Temussi F (2004) Structure elucidation and phytotoxicity of C13 nor-isoprenoids from Cestrum parqui. Phytochemistry 65 : 497 505.
6. DellaGreca M, Di Marino C, Zarrelli A D'Abrosca B (2004) Isolation and phytotoxicity of apocarotenoids from Chenopodium album. Journal of Natural Products 67 : 1492 1495.
7. Flath RA, Cunningham RT, Liquido NJ McGovern TP (1994) Alpha-ionol as attractant for trapping Bactrocera latifrons (Diptera: Tephritidae). Journal of Economic Entomology 87 : 1470 1476.
8. Hee AKW Tan KH (1998) Attraction of female and male Bactrocera papayae to conspecific males fed with methyl eugenol and attraction of females to male sex pheromone components. Journal of Chemical Ecology 24 : 753 764.
9. Herderich M, Neubert C, Winterhalter P, Schreier P Skouroumounis GK (1992) Identification of C13-norisoprenoid flavor precursors in starfruit (Averrhoa carambola L.). Flavour Fragrance Journal 7 : 179 185.
10. Humpf HU Schreier P (1991) Bound aroma compounds from the fruit and the leaves of blackberry (Rubus laciniata L.). Journal of Agricultural and Food Chemistry 39 : 1830 1832.
11. Iijima T, Yaoita Y Kikuchi M (2003) Constituents of Erigeron annuus, Erigeron philadelphicus and Erigeron sumatrensis. Natural Medicines 57 : 75.
12. Ishida T, Enomoto H Nishida R (2008) New attractants for males of the solanaceous fruit fly Bactrocera latifrons. Journal of Chemical Ecology 34 : 1532 1535.
13. Lalel HJD, Singh Z Tan SC (2003) Glycosidically-bound aroma volatile compounds in the skin and pulp of 'Kensington Pride' mango fruit at different stages of maturity. Postharvest Biology and Technology 29 : 205 218.
14. Little HF (1992) Fine structure of presumed pheromone glands of Dacus cucurbitae and D. latifrons (Diptera: Tephritidae). Annals of Entomological Society of America 85 : 326 330.
15. Machida K Kikuchi M (1996) Norisoprenoids from Viburnum dilatatum. Phytochemistry 41 : 1333 1336.
16. Marlatt C, Ho CT Chien M (1992) Studies of aroma constituents bound as glycosides in tomato. Journal of Agricultural and Food Chemistry 40 : 249 252.
17. McQuate GT, Keun YS, Sylva CD, Li QX Jang EB (2004) Active ingredients in cade oil that synergize attractiveness of α-ionol to male Bactrocera latifrons (Diptera: Tephritidae). Journal of Economic Entomology 97 : 862 870.
18. McQuate GT, Bokonon-Ganta AH, Jang EB Messing RH (2008) Age-related responsiveness of male Bactrocera latifrons (Diptera: Tephritidae) to α-ionol 1 cade oil relative to age of sexual maturity. International Journal of Tropical Insect Science 28 : 12 18.
19. Metcalf RL Metcalf ER (1992) Plant Kairomones in Insect Ecology and Control. Chapman & Hall, New York, NY, USA.
20. Nishida R Fukami H (1990) Sequestration of distasteful compounds by some pharmacophagous insects. Journal of Chemical Ecology 16 : 151 164.
21. Nishida R, Tan KH, Serit M, Lajis NH, Sukari AM et al 1988) Accumulation of phenylpropanoids in the rectal glands of males of the Oriental fruit fly, Dacus dorsalis. Experientia 44 : 534 536.
22. Nishida R, Iwahashi O Tan KH (1993) Accumulation of Dendrobium superbum (Orchidaceae) flower fragrance in the rectal glands by males of the melon fly, Dacus cucurbitae (Tephritidae). Journal of Chemical Ecology 19 : 713 722.
23. Nishida R, Tan KH, Wee SL, Hee AKW Toong YC (2004) Phenylpropanoids in the fragrance of the fruit fly orchid, Bulbophyllum cheiri, and their relationship to the pollinator, Bactrocera papayae. Biochemical Systematics and Ecology 32 : 245 252.
24. Pabst A, Barron D, Semon E Schreier P (1992) Two diastereomeric 3-oxo-α-ionol β-D-glucosides from raspberry fruit. Phytochemistry 31 : 1649 1652.
25. Pei YG, Wu QX Shi YP (2007) Triterpenoids and other constituents from Euphorbia humifusa. Journal of Chinese Chemical Society (Taipei, Taiwan) 54 : 1565 1572.
26. Sakho M, Chassagne D Crouzet J (1997) African mango glycosidically bound volatile compounds. Journal of Agricultural and Food Chemistry 45 : 883 888.
27. Schwab W, Mahr C Schreier P (1989) Studies on the enzymic hydrolysis of bound aroma components from Carica papaya fruit. Journal of Agricultural and Food Chemistry 37 : 1009 1012.
28. Sokal R Rohlf F (1995) Biometry, 3rd edn. Freeman, New York, NY, USA.
29. Strauss CR, Wilson B Williams PJ (1987) 3-Oxo-α-ionol, vomifoliol and roseoside in Vitis vinifera fruit. Phytochemistry 26 : 1995 1997.
30. Suárez M, Duque C, Wintoch H Schreier P (1991) Glycosidically bound aroma compounds from the pulp and the peelings of lulo fruit (Solanum vestissimum D.). Journal of Agricultural and Food Chemistry 39 : 1643 1645.
31. Tan KH Nishida R (1995) Incorporation of raspberry ketone in the male rectal glands of the Queensland fruit fly, Bactrocera tryoni Froggatt (Diptera: Tephritidae). Applied Entomology and Zoology 30 : 494 497.
32. Tan KH Nishida R (1998) Ecological significance of male attractant in the defense and mating strategies of the fruit fly Bactrocera papayae. Entomologia Experimentalis et Applicata 89 : 155 158.
33. Tan KH Nishida R (2000) Mutual reproductive benefits between a wild orchid, Bulbophyllum patens, and Bactrocera fruit flies via a floral synomone. Journal of Chemical Ecology 26 : 533 546.
34. Tan KH Nishida R (2007) Zingerone in floral synomone of Bulbophyllum baileyi (Orchidaceae) attracts Bactrocera fruit fly during pollination. Biochemical Systematics and Ecology 35 : 334 341.
35. Vargas RI Nishida T (1985) Survey for Dacus latifrons (Diptera: Tephritidae). Journal of Economic Entomology 78 : 1311 1314.
36. Vargas RI, Walsh WA, Kanehisa D, Jang EB Armstrong JW (1997) Demography of four Hawaiian fruit flies (Diptera: Tephritidae) reared at five constant temperatures. Annals of the Entomological Society of America 90 : 162 168.
37. Wee SL Tan KH (2001) Allomonal and hepatotoxic effects following methyl eugenol consumption in Bactrocera papayae male against Gekko monarchus. Journal of Chemical Ecology 27 : 953 964.
38. Wee SL, Tan KH Nishida R (2007) Pharmacophagy of methyl eugenol by males enhances sexual selection of Bactrocera carambolae. Journal of Chemical Ecology 33 : 1272 1282.
39. Winterhalter P (1990) Bound terpenoids in the juice of the purple passion fruit (Passiflora edulis Sims). Journal of Agricultural and Food Chemistry 38 : 452 455.
40. Winterhalter P Schreier P (1988) Free and bound C13 norisoprenoids in quince (Cydonia oblonga, Mill.) fruit. Journal of Agricultural and Food Chemistry 36 : 1251 1256.
41. Yamazaki Y, Hayashi Y, Arita M, Hieda T Mikami Y (1988) Microbial conversion of α-ionone, α-methylionone, and α-isomethylionone. Applied Environmental Microbiology 54 : 2354 2360.
42. Zhang H, Fletcher MT, Avery JW Kitching W (1997) A suite of odd and even carbon-numbered spiroacetals in Bactrocera latifrons. Synthesis and stereochemistry. Tetrahedron Letters 38 : 3477 3478.