Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets

Methyl eugenol (ME) is a naturally occurring compound found in herbs and spices (e.g., basil, tarragon, black pepper, nutmeg, and anise), fruits

(e.g., bananas and oranges), and a number of essential oils including rose oil.Methyl eugenol (ME) is present as a component of leaf and floral essential

oils from many plant species. Methyl eugenol (ME) is also a naturally occurring carcinogenic compound found in a number of essential oils including rose

oil distilled from Rosa damascena Mill flowers. Methyl eugenol (ME) is a powerful attractant for mature males of B. dorsalis, and has been widely used for

detecting, luring and eradicating B. dorsalis populations worldwide. The presence of methyl eugenol in the oil and difficulty experienced in its separation made this, otherwise

high yielding cultivar, rather less attractive.

Methyleugenol (4-allyl-1,2-dimethoxybenzene) is also a naturally occurring constituent of the essential oils of a number of plants It is present in, for

instance, basil, nutmeg, tarragon, star anise, lemongrass, pimento and fennel.

Methyl eugenol (ME) is a plant phenylpropanoid found in various plant oils, whose metabolites exhibit pheromonal properties and has been largely used as a

sexual lure in detecting, controlling, and eradicating male B. dorsalis populations worldwide.

1 Groh I A M, Rudakovski O, Gründken M, et al. Methyleugenol and oxidative metabolites induce DNA damage and interact with human topoisomerases[J]. Archives of toxicology, 2016, 90(11): 2809-2823.

2 Carlini E A, Dallmeier K, Zelger J L. Methyleugenol as a surgical anesthetic in rodents[J]. Experientia, 1981, 37(6): 588-589.

3 Zhu T, Yan Y, Deng S, et al. Methyleugenol counteracts anorexigenic signals in association with GABAergic inhibition in the central amygdala[J]. Neuropharmacology, 2018, 141: 331-342.

4 Williams G M, Iatropoulos M J, Jeffrey A M, et al. Methyleugenol hepatocellular cancer initiating effects in rat liver[J]. Food and chemical toxicology, 2013, 53: 187-196.

5 Wee S L, Tan K H, Nishida R. Pharmacophagy of methyl eugenol by males enhances sexual selection of Bactrocera carambolae[J]. Journal of Chemical Ecology, 2007, 33(6): 1272-1282.

6 Choudhary D K, Kaul B L. Radiation induced methyl-eugenol deficient mutant ofCymbopogon flexuosus (Nees ex Steud) Wats[J]. Proceedings of the Indian Academy of Sciences-Section B. Part2, Plant Sciences, 1979, 88(3): 225-228.

7 Yano S, Suzuki Y, Yuzurihara M, et al. Antinociceptive effect of methyleugenol on formalin-induced hyperalgesia in mice[J]. European journal of pharmacology, 2006, 553(1-3): 99-103.

8 Zheng W, Zhu C, Peng T, et al. Odorant receptor co-receptor Orco is upregulated by methyl eugenol in male Bactrocera dorsalis (Diptera: Tephritidae)[J]. Journal of insect physiology, 2012, 58(8): 1122-1127.

9 Imai T, Masuda R. Insecticidal activities of methyleugenol and β-asarone, from the herbal medicines Saishin and Sekishōkon, and other alkoxy-propenyl-benzene derivatives against the cigarette beetle Lasioderma serricorne (Coleoptera: Anobiidae)[J]. Applied entomology and zoology, 2017, 52(2): 183-188.

10 Hee A K W, Tan K H. Male sex pheromonal components derived from methyl eugenol in the hemolymph of the fruit fly Bactrocera papayae[J]. Journal of chemical ecology, 2004, 30(11): 2127-2138.

11 Lahlou S, Figueiredo A F, Magalhães P J C, et al. Cardiovascular effects of methyleugenol, a natural constituent of many plant essential oils, in normotensive rats[J]. Life sciences, 2004, 74(19): 2401-2412.

12 ul Haq I, Cáceres C, Meza J S, et al. Different methods of methyl eugenol application enhance the mating success of male Oriental fruit fly (Dipera: Tephritidae)[J]. Scientific reports, 2018, 8(1): 6033.

13 Wang Z J, Tabakoff B, Levinson S R, et al. Inhibition of Na v 1.7 channels by methyl eugenol as a mechanism underlying its antinociceptive and anesthetic actions[J]. Acta Pharmacologica Sinica, 2015, 36(7): 791.

14 Tan K H. Behaviour and chemical ecology of Bactrocera flies[C]//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. Penerbit Universiti Sains Malaysia, 2000: 647-656.

15 Tan K H, Nishida R, Toong Y C. Floral synomone of a wild orchid, Bulbophyllum cheiri, lures Bactrocera fruit flies for pollination[J]. Journal of Chemical Ecology, 2002, 28(6): 1161-1172.

16 Tan K H, Tan L T, Nishida R. Floral phenylpropanoid cocktail and architecture of Bulbophyllum vinaceum orchid in attracting fruit flies for pollination[J]. Journal of chemical ecology, 2006, 32(11): 2429-2441.

17 Rusanov K, Kovacheva N, Rusanova M, et al. Reducing methyl eugenol content in Rosa damascena Mill rose oil by changing the traditional rose flower harvesting practices[J]. European Food Research and Technology, 2012, 234(5): 921-926.

18 Ding W, Levy D D, Bishop M E, et al. Methyleugenol genotoxicity in the Fischer 344 rat using the comet assay and pathway-focused gene expression profiling[J]. Toxicological Sciences, 2011, 123(1): 103-112.

19 Jeurissen S M F, Bogaards J J P, Boersma M G, et al. Human cytochrome P450 enzymes of importance for the bioactivation of methyleugenol to the proximate carcinogen 1 ‘-hydroxymethyleugenol[J]. Chemical research in toxicology, 2006, 19(1): 111-116.

20 Burkey J L, Sauer J M, McQueen C A, et al. Cytotoxicity and genotoxicity of methyleugenol and related congeners—a mechanism of activation for methyleugenol[J]. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis, 2000, 453(1): 25-33.

21 Randerath K, Haglund R E, Phillips D H, et al. 32 P-post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. I. Adult female CD-1 mice[J]. Carcinogenesis, 1984, 5(12): 1613-1622.

22 Nishida, R., Tan, K.H., Serit, M., Lajis, N.H., Sukari, A.M., Takahashi, S., Fukami, H., 1988. Accumulation of phenylpropanoids in the rectal glands of males of the oriental fruit fly, Dacus dorsalis. Experientia 44, 534–536.

23 "Tan, K.H., Nishida, R., 1996. Sex pheromone and mating competition after methyl

eugenol consumption in the Bactrocera dorsalis complex. In: McPheron, B.A.,

Steck, G.J. (Eds.), Fruit Fly Pests—A World Assessment of their Biology and

Management. St. Lucie Press, Delray Beach, pp. 147–153."

24 Metcalf, R.L., 1990. Chemical ecology of Dacinae fruit flies (Diptera: Tephritidae). Annals of the Entomological Society of America 83, 1017–1030.

25 Steiner, L.F., Mitchell, W.C., Harris, E.J., Kozuma, T.T., Fujimotom, S., 1965. Oriental fruit flyeradicationbymaleannihilation. Journal of EconomicEntomology58,961–964.

26 Koyama, J., Teruya, T., Tanaka, K., 1984. Eradication of the oriental fruit fly (Diptera: Tephritidae) from the Okinawa Islands by a male annihilation method. of Economic Entomology 77, 468–472.Journal

27 Anand A K, Mohan M, Haider S Z, et al. Essential oil composition and antimicrobial activity of three Ocimum species from Uttarakhand (India)[J]. Int. J. Pharm. Pharm. Sci, 2011, 3(3): 223-225.

28 Jiang Y, Gong N N, Hu X S, et al. Molecular profiling of activated olfactory neurons identifies odorant receptors for odors in vivo[J]. Nature neuroscience, 2015, 18(10): 1446.

29 De Vincenzi M, Silano M, Maialetti F, et al. Constituents of aromatic plants: II. Estragole[J]. Fitoterapia, 2000, 71(6): 725-729.

30 Spenkelink B, Rachmawati N, Boersma M G, et al. Physiologically based biokinetic model of bioactivation and detoxification of the alkenylbenzene methyleugenol in rat[J]. Toxicology in vitro, 2011, 25(1): 267-285.