A review on natural phenylbutanoid attractants: Occurrence, distribution, and role in nature, especially in relation to Dacini fruit fly behavior and pollination.

Item request has been placed! ×
Item request cannot be made. ×
loading   Processing Request
  • Author(s): Tan KH;Tan KH; Nishida R; Nishida R
  • Source:
    Journal of chemical ecology [J Chem Ecol] 2024 Apr 22. Date of Electronic Publication: 2024 Apr 22.
  • Publication Type:
    Journal Article; Review
  • Language:
    English
  • Additional Information
    • Publication Information:
      Ahead of Print
    • Source:
      Publisher: Springer Country of Publication: United States NLM ID: 7505563 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1573-1561 (Electronic) Linking ISSN: 00980331 NLM ISO Abbreviation: J Chem Ecol Subsets: MEDLINE
    • Publication Information:
      Publication: New York, NY : Springer
      Original Publication: New York, Plenum Press.
    • Abstract:
      The natural occurrence, distribution (within a plant) and roles of four phenylbutanoid compounds (anisyl acetone, cue-lure, raspberry ketone and zingerone) are elucidated for the Asia-Pacific and Oceania regions. These phenylbutanoids may act individually or in combination to attract true fruit fly males belonging to a tribe Dacini of subfamily Dacinae (Diptera: Tepritidae). Of special interest are the mutualistic interactions between the Dacini fruit fly males and the tropical daciniphilous (attracting exclusively Dacini fruit flies) orchids - leading to cross pollination for the orchids and enchanced mating success for the flies. When offered to male flies, anisyl acetone and cue-lure are generally converted to raspberry ketone. Upon consumption, raspberry ketone and zingerone are individually sequestered in the male rectal (pheromonal) gland unchanged. Attracted male flies readily imbibe the phenylbutanoid(s) in the floral synomone to compliment the endogenously synthesized male sex pheromonal components - to enhance attraction of conspecific females during courtship as well as attract conspecific males to form 'leks'. The phenylbutanoid(s) may also act as an allomone to deter vertebrate predators, especially geckos, besides possessing antimicrobial and antioxidant activities. Cue-lure, raspberry ketone and zingerone are important attractants/lures used in pest surveillance and mass trapping under the integrated pest management (IPM) program against quarantine Dacini fruit fly pest species, particularly Bactrocera tryoni and Zeugodacus cucurbitae.
      (© 2024. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.)
    • References:
      Ahmad B, Rehman MU, Amin I, Arif A, Rasool S, Bhat SA, Afzal I, Hussain I, Bilal S, Mir MR (2015) A review on pharmacological properties of zingerone (4-(4-hydroxy-3-methoxyphenyl)-2-butanone. Sci World J 816364:6 https://doi.org/10.1155/2015/816364.
      Ahmad AF, Youssef MSH (2015) Chemical composition and bioactive properties of Illicium verum (star-anise) extracts – Prepared by different methods. J Chem Biol Physi Sci Sec A 5:1160–1170.
      Akiyama M, Murakami K, Ikeda M, Iwatsuki K, Wada A, Tokuno K, Onishi M, Iwabuchi H (2007) Analysis of the headspace volatiles of freshly brewed Arabica coffee using solid-phase microextraction. J Food Sci 72:C388–C396. (PMID: 1799563710.1111/j.1750-3841.2007.00447.x)
      Akiyama M, Murakami K, Hirano Y, Ikeda M, Iwatsuki K, Wada A, Tokuno K, Onishi M, Iwabuchi H (2008) Characterization of headspace aroma compounds of freshly brewed Arabaica coffees and studies on a characteristic aroma compound of Ethiopian coffee. J Food Sci 73:C335–C346. (PMID: 1857697810.1111/j.1750-3841.2008.00752.x)
      Attia RT, Abdel-Mottaleb Y, Abdallah DM, El-Abhar HS, El-Maraghy NN (2019) Raspberry ketone and Garcinia cambogia rebalanced disrupted insulin resistance and leptin signalling in rats fed high fat fructose diet. Biomed Pharmacother 110:500–509. (PMID: 3053023010.1016/j.biopha.2018.11.079)
      Ayinampudi SD, Domala R, Merugu R, Bathula S, Janaswamy MR (2012) New icetexane diterpenes with intestinal α-glucosidase inhibitory and free-radical scavenging activity isolated from Premna tomentosa roots. Fitoterapia 83:88–92. (PMID: 2200472610.1016/j.fitote.2011.09.018)
      Baek SW, Kim ER, Kim JW, Kim YC (2011) Chemical constituents of Abies koreana leaves with inhibitory activity against nitric oxide production in BV2 microglia cells. Nat Prod Sci 17:175–180.
      Baker R, Herbert RH, Lomer RA (1982) Chemical components of the rectal gland secretions of male Dacus cucurbitae, the melon fly. Experientia 38:232–233. (PMID: 10.1007/BF01945082)
      Bakthavatsalam N (2016) Semiochemicals. In: Ecofriendly Pest Managememt for Food Security, Omkar (ed.) Chapter 19, Elsevier. p 563-611.
      Baldwin IT, Preston C, Euler M, Gorham D (1977) Patterns and consequences of benzyl acetone floral emissions from Nicotiana attenuate plants. J Chem Ecol 23:2327–2343. (PMID: 10.1023/B:JOEC.0000006677.56380.cd)
      Barclay HJ, Hendrichs J (2014) Modelling Trapping of fruit flies for detection, suppression, or eradication. In: Shelly TE, Epsky N, Jang EB, Reyes-Flores J, Vargas RI (eds) Trapping and the Detection, Control, and Regulation of Tephritid Fruit Flies. Springer, New York, NY, pp 379–420. https://doi.org/10.1007/978-94-017-9193-9. (PMID: 10.1007/978-94-017-9193-9)
      Barthel WF, Green N, Keiser I, Steiner LF (1957) Anisylacetone, synthetic attractant for male melon fly. Science 126:654. (PMID: 10.1126/science.126.3275.654.a)
      Beekwilder J. Van, der Meer IM, Sibbbesen O, Broekgaarden M, Qvist I, Mikkelsen JD, Hall RD (2007) Microbial production of natural raspberry ketone. Biotechnol J 2:1270–1279. (PMID: 1772215110.1002/biot.200700076)
      Bellas TE, Fletcher BS (1979) Identification of the major components in the secretion from the rectal pheromone glands of the queensland fruit flies Dacus tryoni and Dacus neohumeralis (Diptera: Tephritidae). J Chem Ecol 5:796–803. (PMID: 10.1007/BF00986564)
      Bellik Y (2014) Total antioxidant activity and antimicrobial potency of the essential oil and oleoresin of Zingiber officinale Roscoe. Asian Pac. J. Trop. Med. 4:40–44. https://doi.org/10.1016/S2222-1808(14)60311-X. (PMID: 10.1016/S2222-1808(14)60311-X)
      Beroza M, Alexander BH, Steiner LF, Mitchell WC, Miyashita DH (1960) New synthetic lures for the male melon fly. Science 131:1044–1045. (PMID: 1780809810.1126/science.131.3406.1044)
      Borejsza-Wysocki W, Hrazdina G (1994) Biosynthesis of p-hydroxyphenylbutan-2-one in raspberry fruits and tissue cultures. Phytochemistry 35:673–678. (PMID: 10.1016/S0031-9422(00)90575-2)
      CDFA [California Department of Food and Agriculture] (2013) Insect trapping guide. Gilbert AJ, Bingham RR, Nicolas MA, Clark RA (eds). 13th edition. CDFA, Sacramento, CA, USA.
      Damodaram KJP, Kempraj V, Aurade RM, Venkataramanappa RK, Nandagopal B, Verghese A, Bruce T (2014) Oviposition site selection by Bactrocera dorsalis is mediated through an innate recognition template tuned to γ-octalactone. PLOS One 9:1–6.
      Deifel A (1989) 4-(4-Hydroxyphenyl)-2-butanone (raspberry ketone). Review of natural occurrence and biogenesis Z. Lebensm. Unters For 188:330–332. (PMID: 10.1007/BF01352391)
      Doorenweerd C, Leblanc L, Norrbom AL, San Jose M, Rubinoff D (2018) A global checklist for the 932 fruit fly species in the tribe Dacini (Diptera: Tephritidae). Zookeys 730:19–56. https://doi.org/10.3897/zookeys.730.21786. (PMID: 10.3897/zookeys.730.21786)
      Doorenweerd C, Ekayanti A, Rubinoff D (2020) The Dacini fruit fly fauna of Sulawesi fits Lydekker’s line but also supports Wallacea as a biogeographic region (Diptera, Tephritidae. Zookeys 973:103–122. https://doi.org/10.3897/zookeys.973.55327. (PMID: 10.3897/zookeys.973.55327331170607562968)
      Drew RAI (1974) The responses of fruit fly species (Diptera: Tephritidae) in the South Pacific area to male attractants. J Aust Entomol Soc 13:267–270. (PMID: 10.1111/j.1440-6055.1974.tb02206.x)
      Ebadollahi A, Sendi JJ, Aliakbar A, Razmjou J (2014) Chemical composition and acaricidal effects of essential oils of Foeniculum vulgare Mill. (Apiales: Apiaceae) and Lavandula angustifolia Miller (Lamiales: Lamiaceae) against Tetranychus urticae Koch (Acari: Tetranychidae). Psyche 2014:1-6 https://doi.org/10.1155/2014/424078.
      Ekanayake WMTD, Jayasundara MSH, Peek T, Clarke AR, Schutze MK (2017) The mating system of the true fruit fly Bactrocera tryoni and its sister species Bactrocera neohumeralis. Insect Sci 24:478–490. https://doi.org/10.1111/1744-7917.12337. (PMID: 10.1111/1744-7917.1233727006172)
      El-Baroty GS, El-Baky HA, Farag RS, Saleh MA (2010) Characterization of antioxidant and antimicrobial compounds of cinnamon and ginger essential oils. African J Biochem Res 4:167–174.
      Embong M, Hadziyev D, Molnar S (1977) Essential oils from spices grown in Alberta. Anise oil (Pimpinella anisum). Can J Plant Sci 57:681–688. (PMID: 10.4141/cjps77-100)
      FAO/IAEA (2018) Trapping guidelines for area-wide fruit fly programmes, Second edition. Enkerlin WR, Reyes-Flores J (eds). Rome, Italy. pp 65. Licence: CC BY-NC-SA 3.0 IGO.
      Fay HAC (2012) A highly effective and selective male lure for Bactrocera jarvisi (Tryon) (Diptera: Tephritidae). Aust J Entomol. 51:189–197. (PMID: 10.1111/j.1440-6055.2011.00847.x)
      Flath RA, Ohinata K (1982) Volatile components of the orchid Dendrobium superbum Rchb. f. J Agric Food Chem 30:841–842. (PMID: 10.1021/jf00113a011)
      Fletcher MT, Kitching W (1995) Chemistry of fruit flies. Chem Rev 95:789–828. https://doi.org/10.1021/cr00036a001. (PMID: 10.1021/cr00036a001)
      Frodin DG (2004) History and concepts of big plant genera. Taxon 53:753–776. (PMID: 10.2307/4135449)
      Fronza G, Fuganti C, Guillou C, Reniero F, Joulain D (1998) Natural abundance 2H nuclear magnetic resonance study of the origin of raspberry ketone. J Agr Food Chem 46:248–254. (PMID: 10.1021/jf970530n)
      Fronza G, Fuganti C, Pedrocchi-Fantoni G, Serra S, Zucchi G, Fauhl C, Guillou C, Reniero F (1999) Stable isotope characterization of raspberry ketone extracted from Taxus baccata and obtained by obtained by oxidation of the accompanying alcohol (betuligenol). J Agr Food Chem 47:1150–1155. (PMID: 10.1021/jf980717u)
      Hirvi T, Honkanen E (1984) The aroma of the fruit of sea Buckthorn, Hippophae rhamnoides L. Z. Lebensm. Unters For 179:387–388. (PMID: 10.1007/BF01043436)
      Hirvi T, Honkanen E, Pyysalo T (1981) The aroma of cranberries. (in German) Z Lebensm. Unters For 172:365–367. (PMID: 10.1007/BF01127665)
      Hokkanen E, Pyysalo T, Hirvi T (1980) The aroma of Finnish wild raspberies, Rubus idaeus L. Z. Lebensm. Unters For 171:180–182. (PMID: 10.1007/BF01042646)
      Hokkanen J, Mattila S, Jaakola L, Pirttilä AM, Tolonen A (2009) Identification of phenolic compounds from lingonberry (Vaccinium vitis-idaea L.), bilberry (Vaccinium myrtillus L.) and hybrid bilberry (Vaccinium x intermedium Ruthe L.) leaves. J Agr Food Chem 57:9437–47. (PMID: 10.1021/jf9022542)
      Iwahashi O, Majima T (1986) Lek formation and male-male competition in the melon fly, Dacus cucurbitae Coquillett (Diptera: Tephritidae). Appl Entomol Zool. 21:70–75. https://doi.org/10.1303/aez.21.70. (PMID: 10.1303/aez.21.70)
      Jakubas WJ, Shah PS, Mason JR (1992) Avian repellency of coniferyl and cinnamyl derivatives. Ecol Appl 2:147–156. (PMID: 2775920410.2307/1941771)
      Jang EB, Carvalo LAFN, Chen CC, Siderhurst MS (2017) Cucumber lure trapping of Zeugodacus cucurbitae (Diptera: Tephritidae) in Hawaii and Taiwan: Logevity and nontargets captures. J Econ Entomol 110:201–207. https://doi.org/10.1093/jee/tow268. (PMID: 10.1093/jee/tow26828025314)
      Katte T, Tan KH, Su ZH, Ono H, Nishida R (2020) Floral fragrances in two closely related fruit fly orchids, Bulbophyllum hortorum and B. macranthoides (Orchidaceae): assortments of phenylbutanoids to attract tephritid fruit fly males. Appl Entomol Zool 55:55–64. https://doi.org/10.1007/s13355-019-00653-x. (PMID: 10.1007/s13355-019-00653-x)
      Kempraj V, Park SJ, Taylor PW (2019) γ-Octalactone, an effective oviposition stimulant of Bactrocera tryoni. J Appl Entomol 143:1205–1209. (PMID: 10.1111/jen.12711)
      Khan MA, Manoukis NC, Osborne T, Barchia IM, Gurr GM, Reynolds OL (2017) Semiochemical mediated enhancement of males to complement sterile insect technique in management of the tephritid pest Bactrocera tryoni (Froggatt). Sci Rep-UK 7:13366 https://doi.org/10.1038/s41598-017-13843-w.
      Khan MAM, Deshpande NP, Shuttleworth LA, Osborne T, Collins D, Wilkins MR, Gurr GM, Reynolds OL (2021) Raspberry ketone diet supplement reduces attraction of sterile male Queensland fruit fly to cuelure by altering expression of chemoreceptor genes. Sci Rep-UK 11:17632 https://www.nature.com/articles/s41598-021-96778-7.
      Khoo CCH, Tan KH (2000) Attraction of both sexes of melon fly, Bactrocera cucurbitae to conspecifie males – a comparison after pharmacophagy of cue-lure and a new attractant – zingerone. Entomol Exp Appl 97:317–320. https://doi.org/10.1046/j.1570-7458.2000.00745.x. (PMID: 10.1046/j.1570-7458.2000.00745.x)
      Koeduka T, Watanabe B, Suzuki S, Hiratake J, Mano J, Yazaki K (2011) Characterization of raspberry ketone/zingerone synthase, catalyzing the alpha, beta-hydrogenation of phenylbutenones in raspberry fruits. Biochem Bioph Res Co 412:104–108. https://doi.org/10.1016/j.bbrc.2011.07.052. (PMID: 10.1016/j.bbrc.2011.07.052)
      Koeduka T, Takarada T, Fujii K, Sugiyama A, Yazaki K, Nishihara M, Matsui K (2021) Production of raspberry ketone by redirecting the metabolic flux to the phenylpropanoid pathway in tobacco plants. Metab Eng Co 13:e00180. (PMID: 10.1016/j.mec.2021.e00180)
      Krosch MN, Schutze MK, Armstrong KF, Graham GC, Yeates DK, Clarke AR (2012) A molecular phylogeny for the Tribe Dacini (Diptera: Tephritidae): Systemaatic and biogeographic implications. Mole Phylogenet Evol 64:512–523. https://doi.org/10.1016/j.ympev.2012.05.006. (PMID: 10.1016/j.ympev.2012.05.006)
      Kuba H, Sokei Y (1988) The production of pheromone clouds by spraying in the melon fly, Dacus cucurbitae Coquillett (Diptera: Tephritidae). J Ethol 6:105–110. (PMID: 10.1007/BF02350875)
      Kuba H, Koyama J, Prokopy RJ (1984) Mating behavior of wild melon flies, Dacus cucurbitae Coquillett (Diptera: Tephritidae) in a field cage. Appl Entomol Zool 19:367–373. (PMID: 10.1303/aez.19.367)
      Kumar G, Karthik L, Rao KB (2011) A review on pharmacological and phytochemical properties of Zingiber officinale Roscoe (Zingiberaceae). J Pharma Res 4:2963–2966.
      Kumaran N, Hayes RA, Clarke AR (2014a) Cue-lure but not zingerone make the sex pheromone of male Bactrocera tyoni (Tephritidae: Diptera) more attractive to females. J Insect Physiol 68:36–43. (PMID: 2501054910.1016/j.jinsphys.2014.06.015)
      Kumaran N, Prentis PJ, Mangalan KP, Schutze MK, Clarke AR (2014b) Sexual selection in true fruit flies (Diptera: Tephritidae): transcriptome and experimental evidences for phytochemicals increasing male competitive ability. Mol Ecol 23:4645–4657. https://doi.org/10.1111/mec.12880. (PMID: 10.1111/mec.1288025112896)
      Kumaran N, Van der Burg CA, Qin Y, Cameron SL, Clarke AR, Prentis PJ (2018) Plant-mediated female transcriptomic changes post-mating in a tephritid fruit fly Bactrocera tryoni. Genome Biol Evol 10:94–107. (PMID: 2922041810.1093/gbe/evx257)
      Larsen M, Poll L, Callesen O, Lewis M (1991) Relations between the content of aroma compounds and the sensory evaluation of 10 raspberry varieties (Rubus idaeus L). Acta Agr Scand 41:447–454. (PMID: 10.1080/00015129109439927)
      Leblanc L, Doorenweerd C, San Jose M, Pham HT, Rubinoff D (2018a) Descriptions of four new species of Bactrocera and new country records highlight the high biodiversity of fruit flies in Vietnam (Diptera, Tephritidae, Dacinae). Zookeys 197:87–110. (PMID: 10.3897/zookeys.797.29138)
      Leblanc L, Doorenweerd C, San Jose M, Sirisena UGAI, Hemachandra KS, Rubinoff D (2018b) Description of a new species of Dacus from Sri Lanka, and new country distribution records (Diptera, Tephritidae, Dacinae). Zookeys 795:105–114. (PMID: 10.3897/zookeys.795.29140)
      Leblanc L, Tsatsia F, Doorenweerd C (2021) Novel lures and COI sequences reveal cryptic new species of Bactrocera fruit flies in the Solomon Islands (Diptera, Tephritidae, Dacini). Zookeys 1057:49–103. (PMID: 34552368841702510.3897/zookeys.1057.68375)
      Lee J (2016) Further research on the biological activities and the safety of raspberry ketone is needed. NFS J 2:15–18. (PMID: 10.1016/j.nfs.2015.12.001)
      Lim SH, Choi C-I (2021) Potentials of raspberry ketone as a natural antioxidant. Antioxid 10:482. https://doi.org/10.3390/antiox10030482. (PMID: 10.3390/antiox10030482)
      Lin, Y.L. and Chow, C.J. 1984. Studies on the constituents of aerial parts of Scutellaria rivularis wall. Kuo Li Chung-Kuo 1 Yao Yen Chiu So Yen Chiu Pao Kao141–165.
      Manoukis NC, Jang EB (2013) The diurnal rhythmicity of Bactrocera cucurbitae (Diptera: Tephritidae) Attraction to cue-lure: insights from an interruptable lure and computer vision. Ann Entomol Soc Am 106:136–142. https://doi.org/10.1603/AN12095.
      Marco JA, Barbera O, Rodriguez S, Domingo C, Adell J (1988) Flavonoids and other phenolics from Artemisia hispanica. Phytochemistry 27:3155–3159. (PMID: 10.1016/0031-9422(88)80018-9)
      Meier M, Kohlrnberg B, Braun NA (2003) Isolation of anisyl acetone from Agrwood oil. J Essent Oil Res 15:54–56. (PMID: 10.1080/10412905.2003.9712266)
      Menon AN, Padmakumari KP, Kutty BS, Sumathikutty MA, Sreekumar MM, Arumugham C (2007) Effects of processing on the flavor compounds of Indian fresh ginger (Zingiber officinale Rosc.). J Essent Oil Res 19:105–110. (PMID: 10.1080/10412905.2007.9699240)
      Metcalf RL (1990) Chemical ecology of Dacinae fruit flies (Diptera: Tephritidae). Ann Entomol Soc Am 83:1017–1030. (PMID: 10.1093/aesa/83.6.1017)
      Milke L, Mutz M, Marienhagen J (2020) Synthesis of the character impact compound raspberry ketone and additional flavoring phenylbutanoids of biotechnological interest with Corynebacterium glutamicum. Microb Cell Fact 19:92. https://doi.org/10.1186/s12934-020-01351-y. (PMID: 10.1186/s12934-020-01351-y323169877175512)
      Mir SH, Mir GM (2016) Lekking behaviour and male-male rivalry in the melon fly Bactrocera cucurbitae (Coquillett) (Diptera: Tephritidae). J Insect Behav 29:379–384. (PMID: 10.1007/s10905-016-9568-y)
      Miyoshi T, Ito M, Kitayama T, Isomori S, Yamashita F (2013) Sedative effects of inhaled benzylacetone and structural features contributing to its activity. Biol Pharma Bull 36:1474–1481. https://doi.org/10.1248/bpb.b13-00250. (PMID: 10.1248/bpb.b13-00250)
      Monro J, Richardson NL (1969) Traps, male lures, and a warning system for Queensland fruit fly, Dacus tryoni (Frogg.) (Diptera, Trypetidae). Aust J Agr Res 20:325–338. (PMID: 10.1071/AR9690325)
      Morimoto C, Satoh Y, Hara M, Inoue S, Tsujitae T, Okuda H (2005) Anti-obese action of raspberry ketone. Life Sci 77:194–204. (PMID: 1586260410.1016/j.lfs.2004.12.029)
      Muryati M, Trisyono YA, Wijaksono W, Wahyono W (2017) Deterrent of Bactrocera carambolae resulted from eggs deposition on mango. Agrivita J Agr 39:201–213. https://doi.org/10.17503/agrivita.v39i2.1097. (PMID: 10.17503/agrivita.v39i2.1097)
      Nakahira M, Ono H, Wee SL, Tan KH, Nishida R (2018) Floral synomone diversification of Bulbophyllum sibling species (Orchidaceae) in attracting fruit fly pollinators. Biochem Syst Ecol 81:86–95. https://doi.org/10.1016/j.bse.2018.10.002. (PMID: 10.1016/j.bse.2018.10.002)
      Nakamori H, Soemori H (1985) Diurnal changes in the attraction of the melon fly, Dacus cucurbitae Coquillett (Diptera: Tephritidae), in different habitats. Japanese J Appl Entomol Zool 293:216–222 (in Japansese with English summary). (PMID: 10.1303/jjaez.29.216)
      Nishida R (2014) Chemical ecology of insect-plant interactions: Ecological significance of plant secondary metabolites. Biosci Biotechnol Bioch 78:1–13. (PMID: 10.1080/09168451.2014.877836)
      Nishida R, Fukami H (1990) Sequestration of distasteful compounds by some pharmacophagous insects. J Chem Ecol 16:151–164. https://doi.org/10.1007/BF01021276. (PMID: 10.1007/BF0102127624264904)
      Nishida R, Tan KH, Serit M, Lajis NH, Sukari AM, Takahashi S, Fukami H (1988) Accumulation of phenylpropanoids in the rectal glands of males of the Oriental fruit fly, Dacus dorsalis. Experentia 44:534–536. (PMID: 10.1007/BF01958941)
      Nishida R, Tan KH, Takahashi S, Fukami H (1990) Volatile components of male rectal glands of the melon fly, Dacus cucurbitae Coquillett (Diptera: Tephritidae). Appl Entomol Zool 25:105–112. https://doi.org/10.1303/aez.25.105. (PMID: 10.1303/aez.25.105)
      Nishida R, Iwahashi I, Tan KH (1993) Accumulation of Dendrobium (Orchidaceae) flower fragrance in the rectal glands by males of the melon fly, Dacus cucurbitae (Tephritidae). J Chem Ecol 19:713–722. https://doi.org/10.1007/BF00985003. (PMID: 10.1007/BF0098500324249012)
      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. Biochem Syst Ecol 32:245–252. https://doi.org/10.1016/S0305-1978(03)00179-0. (PMID: 10.1016/S0305-1978(03)00179-0)
      Nishida R, Tan KH (2016) Search for new fruit fly attractants from plants: a review, pp. 249–262. In: Sabater-Munoz B, Vera T, Pereira R, Orankanok W (eds.), Proceedings, 9th International Symposium on Fruit Flies of Economic Importance, Bangkok, Thailand.
      Nishida R, Howcroft N, Tan KH, Su Z-H, Ono H (2022) Floral synomone components of fruit fly-attracting orchids, Bulbophyllum sinapis and B. hahlianum, in Papua New Guinea. Biochem Syst Ecol 105. https://doi.org/10.1016/j.bse.2022.104481.
      Nordlund DA, Lewis WJ (1976) Terminology of chemical releasing stimuli in intraspecific and interspecific interactions. J Chem Ecol 2:211–220. (PMID: 10.1007/BF00987744)
      Ohinata K, Jacobson M, Kobayashi M, Chambers DL, Fujimoto MS, Higa H (1982) Oriental fruit fly and melon fly: Biology and chemical studies of smoke production by males. J Environ Sci Health A17:197–216.
      Oliver JE, Casana-Giner V, Jang EB, McQuate GT, Carvalho L (2002) Improved attractants for the melon fly, Bactrocera cucurbitae. Proceedings of 6th International Fruit Fly Symposium, Stellenbosch, South Africa. p 283-290.
      Ong PT, Hee AKW, Wee SL, Tan KH (2011) The attraction of flowers of Bulbophyllum section Sestochilus to Bactrocera fruit flies (Diptera: Tephritidae). Males Orchid J 8:93–102.
      Ono H, Hee AKW, Jiang HB (2021) Recent advancements in studies on chemosensory mechanisms underlying detection of semiochemicals in Dacini fruit flies of economic importance (Diptera; Tephritidae). Insects 12:106. https://doi.org/10.3390/insects12020106. (PMID: 10.3390/insects12020106335306227911962)
      Osoro EK, Yong ZH, Ndagijimanab A, Imbenzia PS (2013) A review on phenolic compounds in Illicium species and their pharmacological effects. Der Pharmacia Sinica 4:17–30.
      Park SJ, Siderhurst SM, Jamie I, Taylor PW (2016) Hydrolysis of Queensland fruit fly, Bactrocera tryoni (Froggatt), attractants: Kinetics and implications for biological activity. Austr J Chem 69:1162–1166. (PMID: 10.1071/CH16073)
      Park SJ, De Faveri SG, Cheesman J, Hanssen BL, Cameron DMS, Jamie IM, Taylor PM (2020) Zingerone in the flower of Passiflora maliformis attracts an Australian fruit fly, Bactrocera jarvisi (Tryon). Molecules 25:2877. https://doi.org/10.3390/molecules25122877. (PMID: 10.3390/molecules25122877325805217355451)
      Park SJ, Hanssen B, De Faveri S, Cheesman J, Royer J, Cameron D, Jamie J, Jamie I, Taylor P (2022) Plant-based attractant, zingerone and its analogs reveal structural requirements for attraction of Jarvis’s fruit fly. S9-0153 p. 166 Book of Abstract, 2022 ISCE-APACE Joint Meeting of the 3th Annual Meeting of the International Society of Chemical Ecology and the 11th Asia-Pacific Association of Chemical Ecologists Conference, Kuala Lumpur, Malaysia.
      Purnomo H, Jaya F, Widjanarko SB (2010) The effects of type and time of thermal processing on ginger (Zingiber officinale Roscoe) rhizome antioxidant compounds and its quality. Int Food Res J 17:335–347.
      Royer JE (2015) Responses of fruit flies (Tephritidae: Dacinae) to novel male attractants in north Queensland, Australia, and improved lures for some pest species. Austral Entomol 54:411–426. (PMID: 10.1111/aen.12141)
      Royer JE, Mayer DG (2018) Combining cue-lure and methyl eugenol in traps significantly decreases catches of most Bactrocera, Zeugodacus and Dacus Species (Diptera: Tephritidae: Dacinae) in Australia and Papua New Guinea. J Econ Entomol 111:298–303. https://doi.org/10.1093/jee/tox334. (PMID: 10.1093/jee/tox33429272411)
      Royer JE, De Faveri SG, Lowe GE, Wright CL (2014) Cucumber volatile blend, a promising female-bias for Bactrocera cucumis (French 1907) (Diptera: Tephritidae: Dacinae), a pest fruit fly that does not respond to male attractants. Austral Entomol 53:347–352. https://doi.org/10.1111/aen.12083. (PMID: 10.1111/aen.12083)
      Royer JE, Agovaua S, Bokosou J, Kurika K, Mararuai A, Mayer DG, Niangu B (2017) Responses of fruit flies (Diptera: Tephritidae) to new attractants in Papua New Guinea. Austral Entomol 57:40–49. https://doi.org/10.1111/aen.12269. (PMID: 10.1111/aen.12269)
      Royer JE, Mille C, Cazeres S, Brinon J, Mayer DG (2019) Isoeugenol, a more attractive male lure for the cue-lure-responsive pest fruit fly Bactrocera curvipennis (Diptera: Tephritidae: Dacinae), and new records of species responding to zingerone in New Caledonia. J Econ Entomol 112:1502–1507. https://doi.org/10.1093/jee/toz034. (PMID: 10.1093/jee/toz03430834933)
      Royer JE, Tan KH, Mayer DG (2020) Comparative trap catches of male Bactrocera, Dacus and Zeugodacus fruit flies (Diptera: Tephritidae) with four floral phenylbutanoid lures (anisyl acetone, cue-lure, raspberry ketone and zingerone) in Queensland. Australia Environ Entomol 49:815–822. https://doi.org/10.1093/ee/nvaa056. (PMID: 10.1093/ee/nvaa05632514581)
      Samadi Andzagi G, Yaghoubi H, Fardin M (2017) Investigation of compositions and effects of local herbal Silybum marianum and Foeniculum vulgare extractions on hospital acquired infections (HAI) and cell line of liver cancer (HepG2) by MTT assays. J Herb Drug 7:275–282.
      Scolari F, Valerio F, Benelli G, Papadopoulos NT, Vaníčková L (2021) Tephritid fruit fruit fly semiochemicals: Current knowledge and future perspectives. Insects 12:408 ( https://www.mdpi.com/2075-4450/12/5/408 ). (PMID: 33946603814726210.3390/insects12050408)
      Segura DF, Belliard SA, Vera MT, Bachmann GE, Ruiz MJ, Jofre-Bartud F, Fernandez PC, Lopez ML, Shelly TE (2018) Plant chemicals and the sexual behaviour of male Tephritid fruit flies. Ann Entomol Soc Am 111:239–264. https://doi.org/10.1093/aesa/say024. (PMID: 10.1093/aesa/say024)
      Shamshir RA, Wee SL (2019) Zingerone improves mating performance of Zeugodacus tau (Diptera: Tephritidae) through enhancement male courtship activity and sexual signaling. J Insect Physiol 119 https://doi.org/10.1016/j.jinsphys.2019.103949.
      Shelly TE (2010) Effects of methyl eugenol and raspberry ketone/cue lure on the sexual behavior of Bactrocera species (Diptera: Tephritidae). Appl Entomol Zool 45:349–361. (PMID: 10.1303/aez.2010.349)
      Shelly TE (2018) Sexual selection on leks: A fruit fly primer. J Insect Sci 18:1–16. https://doi.org/10.1093/jisesa/iey048. (PMID: 10.1093/jisesa/iey048)
      Shelly TE, Kaneshiro KY (1991) Lek behaviour of the oriental fruit fly in Hawaii. J Insect Behav 20:453–472. (PMID: 10.1007/s10905-007-9091-2)
      Shelly TE, Kurashima RS (2016) Mixing male lures results in an effective multispecies bait for trapping Bactrocera (Diptera: Tephritidae) fruit flies. Fla Entomol 99:318–320. https://doi.org/10.1653/024.099.0229. (PMID: 10.1653/024.099.0229)
      Shelly TE, Villalobos EM (1995) Cue lure and the mating behaviour of male melon flies (Diptera: Tephritidae). Fla Entomol 78:473–482. (PMID: 10.2307/3495532)
      Shelly T, Nishimoto J, Diaz A, Leathers J, War M, Shoemaker R, Al-Zubaidy M, Joseph D (2010) Capture probability of released males of two Bactrocera species (Diptera: Tephritidae) in detection traps in California. J Econ Entomol 103:2o42-2051 https://doi.org/10.1603/EC10153.
      Shelly T, Epsky N, Jang EB, Reyes-Flores J, Vargas R (2014) Trapping and the detection, control, and regulation of Tephritid fruit flies. Springer: Dordrecht Heidelberg, NY London, p 638. https://doi.org/10.1007/978-94-017-9193-9.
      Siderhurst MS, Park SJ, Buller CN, Jamie IM, Manoukis NC, Jang EB, Taylor PW (2016) Raspberry ketone trifluoroacetate, a new attractant for the Queensland fruit fly, Bactrocera tryoni (Froggatt). J Chem Ecol 42:156–162. (PMID: 2692234910.1007/s10886-016-0673-3)
      Singh G, Kapoor IPS, Singh P, de Heluani CS, de Lampasona MP, Catalan CAN (2008) Chemistry, antioxidant and antimicrobial investigations on essential oil and oleoresins of Zingiber officinale. Food Chem Toxicol 46:3295–3302 https://doi.org/10.1016/j.fct.2008.07.017 .
      Sota H, Yasuo T, Hideaki M, Taro I (2006) Study on the volatile compounds of various gingers. Koryo, Terupen oyobi Seiyu Kagaku ni kansuru Toronkai Koen Yoshishu 50:10–12 (in Japanese).
      Tan KH (2000a) Behaviour and chemical ecology of Bactrocera flies. In: Tan KH (ed.) Area-wide control of fruit flies and other insect pests. Joint proceedings of the international conference on area-wide control of insect pests, 28 May-2 June, 1998 and the Fifth International Symposium on Fruit Flies of Economic Importance, Penang, Malaysia, 1-5 June, 1998. p 647–656.
      Tan KH (2000b) Sex pheromone components in defense of melon fly, Bactrocera cucurbitae against Asian house gecko, Hemidactylus frenatus. J Chem Ecol 26:697–704. https://doi.org/10.1023/A:1005480206023. (PMID: 10.1023/A:1005480206023)
      Tan KH (2009) Fruit fly pests as pollinators of wild orchids. Orchid Digest 73:180–187.
      Tan KH, Lee SL (1982) Species diversity and abundance of Dacus (Diptera: Tephritidae) in five ecosystems of Penang, West Malaysia. Bull Entomol Res 72:709–716. https://doi.org/10.1017/S0007485300008737. (PMID: 10.1017/S0007485300008737)
      Tan KH, Nishida R (1995) Incorporation of raspberry ketone in the male rectal glands of the Queensland fruit fly, Bactrocera tryoni Froggatt (Diptera: Tephritidae). Appl Entomol Zool 30:494–497. https://doi.org/10.1303/aez.30.494. (PMID: 10.1303/aez.30.494)
      Tan KH, Nishida R (1996) Sex pheromone and mating competition after methyl eugenol comsumption in the Bactrocera dorsalis complex. In: McPheron BA, Steck GJ (eds) Fruit Fly Pests — A World Assessment of Their Biology and Management. St. Lucie Press, Florida, pp 147–153.
      Tan KH, Nishida R (2000) Mutual reproductive benefits between a wild orchid, Bulbophyllum patens, and Bactrocera fruit flies via a floral synomone. J Chem Ecol 26:533–546. https://doi.org/10.1023/A:1005477926244. (PMID: 10.1023/A:1005477926244)
      Tan KH, Nishida R, Toong YC (2002) Floral synomone of a wild orchid, Bulbophyllum cheiri, lures Bactrocera fruit flies for pollination. J Chem Ecol 28:1161–1172. https://doi.org/10.1023/A:1016277500007. (PMID: 10.1023/A:101627750000712184394)
      Tan KH, Tan LT, Nishida R (2006) Floral phenylpropanoid cocktail and architecture of Bulbophyllum vinaceum orchid in attracting fruit flies for pollination. J Chem Ecol 32:2429–2441. https://doi.org/10.1007/s10886-006-9154-4. (PMID: 10.1007/s10886-006-9154-417082990)
      Tan KH, Vermeulen JJ, Katte T, Ono H, Nishida R (2021) Diversification in both the floral morphology and chemistry in two daciniphilous orchid ecotypes in Borneo. Arthro-Plant Interact 15:447–455. https://doi.org/10.1007/s11829-021-09821-9. (PMID: 10.1007/s11829-021-09821-9)
      Tan KH, Ong PT, Tan LT (2023) Morphology and movement of Bulbophyllum hortorum (Orchidacea) flowers enable selection of optimal-sized Dacini fruit fly males. Arthropod-Plant Interact 17:647–660. https://doi.org/10.1007/s11829-023-09987-4. (PMID: 10.1007/s11829-023-09987-4)
      Tan KH, Nishida R (2005) Synomone or Kairomone? - Bulbophyllum apertum (Orchidaceae) flower releases raspberry ketone to attract Bactrocera fruit flies. J Chem Ecol 31:509-519 https://doi.org/10.1007/s10886-005-2023-8.
      Tan KH, Nishida R (2007) Zingerone in the floral synomone of Bulbophyllum baileyi (Orchidaceae) attracts Bactrocera fruit flies during pollination. Biochem Syst Ecol 35:334-341 https://doi.org/10.1016/j.bse.2007.01.013.
      Tan KH, Nishida R (2012) Methyl eugenol: its occurrence, distribution, and role in nature, especially in relation to insect behavior and pollination. J Insect Sci 12:56.
      Tan KH, Nishida R (2015) Pollination of bactrocerophilous Bulbophyllum orchids. In Elliott J, Kuraweil HF, O’Byrne P, Tan KW, van Schans AS, Wong SM, Yam TW (eds.). Proceedings of the 20th World Orchid Conference, Singapore, 201. p 273-279. https://www.researchgate.net/publication/275834142_Pollination_of_bactrocerophilous_Bulbophyllum_Orchids.
      Tan KH, Tan LT (2018) Movements of floral parts and roles of the tooth on column wall of Bulbophyllum praetervisum (Orchidaceae) flower for pollination by Dacini fruit flies (Diptera: Tephritidae). J Poll Ecol 24: 157-163. https://www.pollinationecology.org/index.php?journal=jpe&page=article&op=view&path%5B%5D=500.
      Tan KH, Nishida R, Jang EB, Shelly TE (2014) Pheromones, male lures, and trapping of tephritid fruit flies. In: Shelly TE, Epsky N, Jang EB, Reyes-Flores J, Vargas RI (eds.). Trapping and the Detection, Control, and Regulation of Tephritid Fruit Flies. Springer:New York, NY. p 15–74. https://doi.org/10.1007/978-94-017-9193-9.
      Tan, K.H. 1983. Response of Dacus (Diptera: Tephritidae) to Ocimum sanctum (Linn.) extracts and different synthetic attractants in Penang, Malaysia. In: Cavalloro R (ed.) Proceedings of the CEC/IOBC International Symposium, Athens, “Fruit flies of economic importance”. p 513–520.
      Thamrin S, Rauf A, Purwatiningsih, Ratna ES (2017) Identification of kairomonal compounds from host plants aattractive to melon fly, Zeugodacus cucurbitae (Coquillett) (Diptera: Tephritidae). J Enbtomol 14:216–227. (PMID: 10.3923/je.2017.216.227)
      Thuy DTT, Tran TT, Thuy TTT, Pham THM, Quoc TT, Pham QL, Duy CN, Long GB, Nyuyen QC (2019) Isolation process and compound identification of agarwood essential oils from Aquilaria crassna cultivated at three different locations in Vietnam. Processes 2019(7):432. https://doi.org/10.3390/pr7070432. (PMID: 10.3390/pr7070432)
      Vargas RI, Stark JD, Kido MH, Ketter HM, Whitehand LC (2000) Methyl eugenol and cue-lure traps for suppression of male oriental fruit flies and melon flies (Diptera: Tephritidae) in Hawaii: effects of lure mixtures and weathering. J Econ Entomol 93:81–87. (PMID: 1465851510.1603/0022-0493-93.1.81)
      Vargas RI, Shelly TE, Leblanc L, Piñero JC (2010) Recent advances in methyl eugenol and cue-lure technologies for fruit fly detection, monitoring, and control in Hawaii. Vitam Horm 83: 575-595 https://doi.org/10.1016/S0083-6729(10)83023-7 .
      Wee SL, Clarke A (2020) Male-lure type, lure dosage, and fly age at feeding all influence male mating success in Jarvis’ fruit fly. Sci Rep-UK 10:15004. https://doi.org/10.1038/s41598-020-72209-x. (PMID: 10.1038/s41598-020-72209-x)
      Wee SL, Tan KH (2001) Allomonal and hepatotoxic effects following methyl eugenol consumption in Bactrocera papayae male against Gekko monarchus. J Chem Ecol 27:953–964. https://doi.org/10.1023/A:1010387020135. (PMID: 10.1023/A:101038702013511471947)
      Wee SL, Tan KH, Nishida R (2007) Pharmacophagy of methyl eugenol by males enhances sexual selection of Bactrocera carambolae. J Chem Ecol 33:1272–1282. https://doi.org/10.1007/s10886-007-9295-0. (PMID: 10.1007/s10886-007-9295-017443401)
      Wee SL, Peek T, Clarke AR (2018) The responsiveness of Bactrocera jarvisi (Diptera: Tephritidae) to two naturally occurring phenylbutanoids, zingerone and raspberry ketone. J Insect Physiol 109:41–46. https://doi.org/10.1016/j.jinsphys.2018.06.004. (PMID: 10.1016/j.jinsphys.2018.06.00429890169)
      Wee SL, Royer JE, Herring J, Meyer DG, Tan KH (2020) Relative response of male Bactrocera frauenfeldi (Diptera: Tephritidae) to phenylbutanoid phytochemicals: implications for fruit fly control and plant-insect interactions. Chemoecology 30:305–314. https://doi.org/10.1007/s00049-020-00320-6. (PMID: 10.1007/s00049-020-00320-6)
      Winter M (1961) Odeur et constitution XIX. Sur des homologues et analogues de la p-hydroxyphényl-1-butanone-3 («cétone de framboise»). Helv Chim Acta 44:2110–2121. (PMID: 10.1002/hlca.19610440738)
      Yang JF, Yang CH, Chang HW, Yang CS, Wang SM, Hsieh MC, Chuang LY (2010) Chemical composition and antibacterial activities of Illicium verum against antibiotic-resistant pathogens. J Med Food 13:1254–1262. (PMID: 2082831610.1089/jmf.2010.1086)
      Yang CH, Chang FR, Chang HW, Wang SM, Hsieh MC, Chuang LY (2012) Investigation of the antioxidant activity of Illicium verum extracts. J Med Plants Res 6:314–324.
      Yu X, Cheng B (1986) Studies on the chemical constituents of the essential oil from Limnophila rugose. Acta Bot. Yunnan. 8:103–106.
      Zhang H (2014) Research progress in chemical synthesis of raspberry ketone. Acetaldehyde Acetic Acid Chemistry and Industry 16:12–19.
      Zhang YX, Li JS, Chen LH, Peng WW, Cai BC (2012) Simultaneous determination of five gingerols in raw and processed ginger by HPLC. Chinese Pharma J 47:471–474.
      Zorn H, Fischer-Zorn M, Berger RG (2003) A labeling study to elucidate the biosynthesis of 4-(4-hydroxyphenyl)-butan-2-one (raspberry ketone) by Nidula niveo-tomentosa. Appl Environ Microbiol 69:367–372. (PMID: 1251401715247610.1128/AEM.69.1.367-372.2003)
    • Contributed Indexing:
      Keywords: Anisyl acetone; Cue-lure; Dacini fruit flies; Daciniphilous orchids; Floral synomone; Raspberry ketone; Semiochemicals; Sexual reproduction; Zingerone
    • Publication Date:
      Date Created: 20240421 Latest Revision: 20240421
    • Publication Date:
      20240422
    • Accession Number:
      10.1007/s10886-024-01499-6
    • Accession Number:
      38644437