Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE (Open Access)

Floral constituents of the Australian tar tree, Semecarpus australiensis

Soo Jean Park https://orcid.org/0000-0002-5414-6772 A B * , Jodie Cheesman C , Donald N. S. Cameron A B , Stefano G. De Faveri C and Phillip W. Taylor A B
+ Author Affiliations
- Author Affiliations

A Applied BioSciences, Macquarie University, Sydney, 2109, Australia.

B Australian Research Council Centre for Fruit Fly Biosecurity Innovation, Macquarie University, North Ryde, NSW 2109, Australia.

C Horticulture and Forestry Science, Queensland Department of Agriculture and Fisheries, Mareeba, Qld, Australia.

* Correspondence to: soojean.park@mq.edu.au

Handling Editor: Charlotte Williams

Australian Journal of Chemistry 75(12) 945-952 https://doi.org/10.1071/CH22097
Submitted: 27 April 2022  Accepted: 22 September 2022   Published: 23 November 2022

© 2022 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND)

Abstract

Floral constituents of the Australian tar tree, Semecarpus australiensis, distributed in Melanesia and Northern Australia, were extracted with solvent, and analyzed by gas chromatography-mass spectrometry. The main constituents were 16- and 18-carbon fatty acids and their ethyl esters. Amongst the 67 identified compounds, zingerone was detected in minute quantity, providing the chemical basis for previous observations of fruit fly attraction to the flowers. The present study is the first to report the chemical profile of tar tree flowers.

Keywords: fatty acids, floral volatiles, fruit fly, GC-MS, isoeugenol, native cashew, salicylates, Tephritidae.


References

[1]  (a) K-H Tan, R Nishida, Mutual reproductive benefits between a wild orchid, Bulbophyllum patens, and Bactrocera fruit flies via a floral synomone. J Chem Ecol 2000, 26, 533.
         | Mutual reproductive benefits between a wild orchid, Bulbophyllum patens, and Bactrocera fruit flies via a floral synomone.Crossref | GoogleScholarGoogle Scholar |
      (b) K-H Tan, R Nishida, Synomone or kairomone? – Bulbophyllum apertum flower releases raspberry ketone to attract Bactrocera fruit flies. J Chem Ecol 2005, 31, 497.
         | Synomone or kairomone? – Bulbophyllum apertum flower releases raspberry ketone to attract Bactrocera fruit flies.Crossref | GoogleScholarGoogle Scholar |
      (c) K-H Tan, R Nishida, Y-C Toong, Floral synomone of a wild orchid, Bulbophyllum cheiri, lures Bactrocera fruit flies for pollination. J Chem Ecol 2002, 28, 1161.
         | Floral synomone of a wild orchid, Bulbophyllum cheiri, lures Bactrocera fruit flies for pollination.Crossref | GoogleScholarGoogle Scholar |
      (d) KH Tan, R Nishida, Zingerone in the floral synomone of Bulbophyllum baileyi (Orchidaceae) attracts Bactrocera fruit flies during pollination. Biochem Syst Ecol 2007, 35, 334.
         | Zingerone in the floral synomone of Bulbophyllum baileyi (Orchidaceae) attracts Bactrocera fruit flies during pollination.Crossref | GoogleScholarGoogle Scholar |
      (e) KH Tan, R Nishida, editors. Pollination of bactrocerophilous Bulbophyllum orchids. Proceedings of the 20th World Orchid Conference. Singapore: Singarpore Botanic Gardens; 2011.
      (f) KH Tan, LT Tan, R Nishida, Floral phenylpropanoid cocktail and architecture of Bulbophyllum vinaceum orchid in attracting fruit flies for pollination. J Chem Ecol 2006, 32, 2429.
         | Floral phenylpropanoid cocktail and architecture of Bulbophyllum vinaceum orchid in attracting fruit flies for pollination.Crossref | GoogleScholarGoogle Scholar |
      (g) T Katte, KH Tan, Z-H Su, H Ono, R Nishida, 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 2020, 55, 55.
         | Floral fragrances in two closely related fruit fly orchids, Bulbophyllum hortorum and B. macranthoides (Orchidaceae): assortments of phenylbutanoids to attract tephritid fruit fly males.Crossref | GoogleScholarGoogle Scholar |

[2]  (a) RAI Drew, The response of fruit fly species (Diptera: Tephritidae) in the South Pacific area to male attractants. Aust J Entomol 1974, 13, 267.
         | The response of fruit fly species (Diptera: Tephritidae) in the South Pacific area to male attractants.Crossref | GoogleScholarGoogle Scholar |
      (b) BS Fletcher, The biology of dacine fruit flies. Annu Rev Entomol 1987, 32, 115.
         | The biology of dacine fruit flies.Crossref | GoogleScholarGoogle Scholar |

[3]  (a) HAC Fay, A highly effective and selective male lure for Bactrocera jarvisi (Tryon) (Diptera: Tephritidae). Aust J Entomol 2012, 51, 189.
         | A highly effective and selective male lure for Bactrocera jarvisi (Tryon) (Diptera: Tephritidae).Crossref | GoogleScholarGoogle Scholar |
      (b) M Nakahira, H Ono, SL Wee, KH Tan, R Nishida, Floral synomone diversification of Bulbophyllum sibling species (Orchidaceae) in attracting fruit fly pollinators. Biochem Syst Ecol 2018, 81, 86.
         | Floral synomone diversification of Bulbophyllum sibling species (Orchidaceae) in attracting fruit fly pollinators.Crossref | GoogleScholarGoogle Scholar |
      (c) JE Royer, S Agovaua, J Bokosou, K Kurika, A Mararuai, DG Mayer, et al. Responses of fruit flies (Diptera: Tephritidae) to new attractants in Papua New Guinea. Aust Entomol 2018, 57, 40.
         | Responses of fruit flies (Diptera: Tephritidae) to new attractants in Papua New Guinea.Crossref | GoogleScholarGoogle Scholar |
      (d) JE Royer, C Mille, S Cazeres, J Brinon, DG Mayer, 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 2019, 112, 1502.
         | 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.Crossref | GoogleScholarGoogle Scholar |
      (e) JE Royer, KH Tan, DG Mayer, Comparative trap catches of male Bactrocera, Dacus, and Zeugodacus Fruit Flies (Diptera: Tephritidae) with four floral phenylbutanoid lures (anisyl aetone, cue-lure, raspberry ketone, and zingerone) in Queensland, Australia. Environ Entomol 2020, 49, 815.
         | Comparative trap catches of male Bactrocera, Dacus, and Zeugodacus Fruit Flies (Diptera: Tephritidae) with four floral phenylbutanoid lures (anisyl aetone, cue-lure, raspberry ketone, and zingerone) in Queensland, Australia.Crossref | GoogleScholarGoogle Scholar |

[4]  (a) JE Royer, Responses of fruit flies (Tephritidae: Dacinae) to novel male attractants in north Queensland, Australia, and improved lures for some pest species. Aust Entomol 2015, 54, 411.
         | Responses of fruit flies (Tephritidae: Dacinae) to novel male attractants in north Queensland, Australia, and improved lures for some pest species.Crossref | GoogleScholarGoogle Scholar |
      (b) JE Royer, M Khan, DG Mayer, Methyl-isoeugenol, a highly attractive male lure for the cucurbit flower pest Zeugodacus diversus (Coquillett) (syn. Bactrocera diversa) (Diptera: Tephritidae: Dacinae). J Econ Entomol 2018, 111, 1197.
         | Methyl-isoeugenol, a highly attractive male lure for the cucurbit flower pest Zeugodacus diversus (Coquillett) (syn. Bactrocera diversa) (Diptera: Tephritidae: Dacinae).Crossref | GoogleScholarGoogle Scholar |

[5]  (a) JAM Paula, PH Ferri, MTF Bara, LMF Tresvenzol, FAS Sá, JR Paula, Infraspecific chemical variability in the essential oils of Pimenta pseudocaryophyllus (Gomes) L.R. Landrum (Myrtaceae). Biochem Syst Ecol 2011, 39, 643.
         | Infraspecific chemical variability in the essential oils of Pimenta pseudocaryophyllus (Gomes) L.R. Landrum (Myrtaceae).Crossref | GoogleScholarGoogle Scholar |
      (b) KC Wong, Y Sivasothy, PL Boey, H Osman, B Sulaiman, Essential oils of Etlingera elatior (Jack) R. M. Smith and Etlingera littoralis (Koenig) Giseke. J Essent Oil Res 2010, 22, 461.
         | Essential oils of Etlingera elatior (Jack) R. M. Smith and Etlingera littoralis (Koenig) Giseke.Crossref | GoogleScholarGoogle Scholar |
      (c) L de, PC Nogueira, V Bittrich, GJ Shepherd, AV Lopes, AJ Marsaioli, The ecological and taxonomic importance of flower volatiles of Clusia species (Guttiferae). Phytochemistry 2001, 56, 443.
         | The ecological and taxonomic importance of flower volatiles of Clusia species (Guttiferae).Crossref | GoogleScholarGoogle Scholar |
      (d) H-S Choi, M Sawamura, Composition of the essential oil of Citrus tamurana Hort. ex Tanaka (Hyuganatsu). J Agric Food Chem 2000, 48, 4868.
         | Composition of the essential oil of Citrus tamurana Hort. ex Tanaka (Hyuganatsu).Crossref | GoogleScholarGoogle Scholar |

[6]  S Raghu, Functional significance of phytochemical lures to dacine fruit flies (Diptera: Tephritidae): an ecological and evolutionary synthesis. Bull Entomol Res 2004, 94, 385.
         | Functional significance of phytochemical lures to dacine fruit flies (Diptera: Tephritidae): an ecological and evolutionary synthesis.Crossref | GoogleScholarGoogle Scholar |

[7]  R Nishida, KH Tan, M Serit, NH Lajis, AM Sukari, S Takahashi, et al. Accumulation of phenylpropanoids in the rectal glands of males of the Oriental fruit fly, Dacus dorsalis. Experientia 1988, 44, 534.
         | Accumulation of phenylpropanoids in the rectal glands of males of the Oriental fruit fly, Dacus dorsalis.Crossref | GoogleScholarGoogle Scholar |

[8]  (a) S-L Wee, K-H Tan, R Nishida, Pharmacophagy of methyl eugenol by males enhances sexual selection of Bactrocera carambolae. J Chem Ecol 2007, 33, 1272.
         | Pharmacophagy of methyl eugenol by males enhances sexual selection of Bactrocera carambolae.Crossref | GoogleScholarGoogle Scholar |
      (b) N Kumaran, PJ Prentis, KP Mangalam, MK Schutze, AR Clarke, Sexual selection in true fruit flies (Diptera: Tephritidae): transcriptome and experimental evidences for phytochemicals increasing male competitive ability. Mol Ecol 2014, 23, 4645.
         | Sexual selection in true fruit flies (Diptera: Tephritidae): transcriptome and experimental evidences for phytochemicals increasing male competitive ability.Crossref | GoogleScholarGoogle Scholar |

[9]  SJ Park, SG De Faveri, J Cheesman, BL Hanssen, DNS Cameron, IM Jamie, et al. Zingerone in the flower of Passiflora maliformis attracts an Australian fruit fly, Bactrocera jarvisi (Tryon). Molecules 2020, 25, 2877.
         | Zingerone in the flower of Passiflora maliformis attracts an Australian fruit fly, Bactrocera jarvisi (Tryon).Crossref | GoogleScholarGoogle Scholar |

[10]  (a) AWS May, Queensland host records for the Dacinae (fam. Trypetidae). Queens J Agric Sci 1953, 10, 36.
      (b) AWS May, Queensland host records for the Dacinae (fam. Trypetidae). Second supplementary lists. Queens J Agric Sci 1960, 17, 195.

[11]  Zich FA, Hyland BPM, Whiffin T, Kerrigan RA. Australian tropical rainforest plants, Edition 8. 2020. Available at https://apps.lucidcentral.org/rainforest/

[12]  B Huang, L Qin, Q Chu, Q Zhang, L Gao, H Zheng, Comparison of headspace SPME with hydrodistillation and SFE for analysis of the volatile components of the roots of Valeriana officinalis var. latifolia. Chromatographia 2008, 69, 489.
         | Comparison of headspace SPME with hydrodistillation and SFE for analysis of the volatile components of the roots of Valeriana officinalis var. latifolia.Crossref | GoogleScholarGoogle Scholar |

[13]  Bramston-Cook R. Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100% dimethylpolysiloxane columns. 2013. Available at http://lotusinstruments.com/wp/wp‐content/uploads/List‐of‐Kovats‐Indices‐for‐C2‐C13‐Hydrocarbons.pdf

[14]  S Ohnishi, T Shibamoto, Volatile compounds from heated beef fat and beef fat with glycine. J Agric Food Chem 1984, 32, 987.
         | Volatile compounds from heated beef fat and beef fat with glycine.Crossref | GoogleScholarGoogle Scholar |

[15]  J Xie, B Sun, F Zheng, S Wang, Volatile flavor constituents in roasted pork of Mini-pig. Food Chem 2008, 109, 506.
         | Volatile flavor constituents in roasted pork of Mini-pig.Crossref | GoogleScholarGoogle Scholar |

[16]  Y Qiao, B Xie, Y Zhang, Y Zhang, G Fan, XL Yao, et al. Characterization of aroma active compounds in fruit juice and peel oil of jinchen sweet orange fruit (Citrus sinensis (L.) Osbeck) by GC-MS and GC-O. Molecules 2008, 13, 1333.
         | Characterization of aroma active compounds in fruit juice and peel oil of jinchen sweet orange fruit (Citrus sinensis (L.) Osbeck) by GC-MS and GC-O.Crossref | GoogleScholarGoogle Scholar |

[17]  NK Leela, TM Vipin, KM Shafeekh, V Priyanka, J Rema, Chemical composition of essential oils from aerial parts of Cinnamomum malabatrum (Burman f.) Bercht & Presl. Flavour Fragr J 2009, 24, 13.
         | Chemical composition of essential oils from aerial parts of Cinnamomum malabatrum (Burman f.) Bercht & Presl.Crossref | GoogleScholarGoogle Scholar |

[18]  A Angioni, A Barra, V Coroneo, S Dessi, P Cabras, Chemical composition, seasonal variability, and antifungal activity of Lavandula stoechas L. ssp. stoechas essential oils from stem/leaves and flowers. J Agric Food Chem 2006, 54, 4364.
         | Chemical composition, seasonal variability, and antifungal activity of Lavandula stoechas L. ssp. stoechas essential oils from stem/leaves and flowers.Crossref | GoogleScholarGoogle Scholar |

[19]  R Mebazaa, A Mahmoudi, M Fouchet, MD Santos, F Kamissoko, A Nafti, et al. Characterisation of volatile compounds in Tunisian fenugreek seeds. Food Chem 2009, 115, 1326.
         | Characterisation of volatile compounds in Tunisian fenugreek seeds.Crossref | GoogleScholarGoogle Scholar |

[20]  RA Cole, WA Haber, WN Setzer, Chemical composition of essential oils of seven species of Eugenia from Monteverde, Costa Rica. Biochem Syst Ecol 2007, 35, 877.
         | Chemical composition of essential oils of seven species of Eugenia from Monteverde, Costa Rica.Crossref | GoogleScholarGoogle Scholar |

[21]  N Radulović, P Blagojević, R Palić, Comparative study of the leaf volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae). Molecules 2010, 15, 6168.
         | Comparative study of the leaf volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae).Crossref | GoogleScholarGoogle Scholar |

[22]  K Javidnia, R Miri, M Kamalinejad, H Khazraii, Chemical composition of the volatile oil of aerial parts of Valeriana sisymbriifolia Vahl. grown in Iran. Flavour Fragr J 2006, 21, 516.
         | Chemical composition of the volatile oil of aerial parts of Valeriana sisymbriifolia Vahl. grown in Iran.Crossref | GoogleScholarGoogle Scholar |

[23]  G Fan, W Lu, X Yao, Y Zhang, K Wang, S Pan, Effect of fermentation on free and bound volatile compounds of orange juice. Flavour Fragr J 2009, 24, 219.
         | Effect of fermentation on free and bound volatile compounds of orange juice.Crossref | GoogleScholarGoogle Scholar |

[24]  RA Pérez, T Navarro, C de Lorenzo, HS–SPME analysis of the volatile compounds from spices as a source of flavour in ‘Campo Real’ table olive preparations. Flavour Fragr J 2007, 22, 265.
         | HS–SPME analysis of the volatile compounds from spices as a source of flavour in ‘Campo Real’ table olive preparations.Crossref | GoogleScholarGoogle Scholar |

[25]  JD Ramsey, RJ Flanagan, Detection and identification of volatile organic compounds in blood by headspace gas chromatography as an aid to the diagnosis of solvent abuse. J Chromatogr A 1982, 240, 423.
         | Detection and identification of volatile organic compounds in blood by headspace gas chromatography as an aid to the diagnosis of solvent abuse.Crossref | GoogleScholarGoogle Scholar |

[26]  JA Pino, J Mesa, Y Muñoz, MP Martí, R Marbot, Volatile components from mango (Mangifera indica L.) cultivars. J Agric Food Chem 2005, 53, 2213.
         | Volatile components from mango (Mangifera indica L.) cultivars.Crossref | GoogleScholarGoogle Scholar |

[27]  W Fan, MC Qian, Characterization of aroma compounds of Chinese “Wuliangye” and “Jiannanchun” liquors by aroma extract dilution analysis. J Agric Food Chem 2006, 54, 2695.
         | Characterization of aroma compounds of Chinese “Wuliangye” and “Jiannanchun” liquors by aroma extract dilution analysis.Crossref | GoogleScholarGoogle Scholar |

[28]  AE Edris, R Chizzola, C Franz, Isolation and characterization of the volatile aroma compounds from the concrete headspace and the absolute of Jasminum sambac (L.) Ait. (Oleaceae) flowers grown in Egypt. Eur Food Res Technol 2007, 226, 621.
         | Isolation and characterization of the volatile aroma compounds from the concrete headspace and the absolute of Jasminum sambac (L.) Ait. (Oleaceae) flowers grown in Egypt.Crossref | GoogleScholarGoogle Scholar |

[29]  E Alissandrakis, PA Tarantilis, PC Harizanis, M Polissiou, Comparison of the volatile composition in thyme honeys from several origins in Greece. J Agric Food Chem 2007, 55, 8152.
         | Comparison of the volatile composition in thyme honeys from several origins in Greece.Crossref | GoogleScholarGoogle Scholar |

[30]  W Fan, MC Qian, Identification of aroma compounds in Chinese ‘Yanghe Daqu’ liquor by normal phase chromatography fractionation followed by gas chromatography[sol]olfactometry. Flavour Fragr J 2006, 21, 333.
         | Identification of aroma compounds in Chinese ‘Yanghe Daqu’ liquor by normal phase chromatography fractionation followed by gas chromatography[sol]olfactometry.Crossref | GoogleScholarGoogle Scholar |

[31]  A Tava, L Pecetti, M Ricci, MA Pagnotta, L Russi, Volatile compounds from leaves and flowers of Bituminaria bituminosa (L.) Stirt. (Fabaceae) from Italy. Flavour Fragr J 2007, 22, 363.
         | Volatile compounds from leaves and flowers of Bituminaria bituminosa (L.) Stirt. (Fabaceae) from Italy.Crossref | GoogleScholarGoogle Scholar |

[32]  B Fernández de Simón, E Esteruelas, ÁM Muñoz, E Cadahía, M Sanz, Volatile compounds in acacia, chestnut, cherry, ash, and oak woods, with a view to their use in cooperage. J Agric Food Chem 2009, 57, 3217.
         | Volatile compounds in acacia, chestnut, cherry, ash, and oak woods, with a view to their use in cooperage.Crossref | GoogleScholarGoogle Scholar |

[33]  J Rohloff, AM Bones, Volatile profiling of Arabidopsis thaliana – Putative olfactory compounds in plant communication. Phytochemistry 2005, 66, 1941.
         | Volatile profiling of Arabidopsis thaliana – Putative olfactory compounds in plant communication.Crossref | GoogleScholarGoogle Scholar |

[34]  M Miyazawa, T Nishiguchi, C Yamafuji, Volatile components of the leaves of Brassica rapa L. var. perviridis Bailey. Flavour Fragr J 2005, 20, 158.
         | Volatile components of the leaves of Brassica rapa L. var. perviridis Bailey.Crossref | GoogleScholarGoogle Scholar |

[35]  F Kenig, D-JH Simons, D Crich, JP Cowen, GT Ventura, T Rehbein-Khalily, Structure and distribution of branched aliphatic alkanes with quaternary carbon atoms in Cenomanian and Turonian black shales of Pasquia Hills (Saskatchewan, Canada). Org Geochem 2005, 36, 117.
         | Structure and distribution of branched aliphatic alkanes with quaternary carbon atoms in Cenomanian and Turonian black shales of Pasquia Hills (Saskatchewan, Canada).Crossref | GoogleScholarGoogle Scholar |

[36]  R Palic, G Stojanovic, S Alagic, M Nikolic, Z Lepojevic, Chemical composition and antimicrobial activity of the essential oil and CO2 extracts of the oriental tobacco, Prilep. Flavour Fragr J 2002, 17, 323.
         | Chemical composition and antimicrobial activity of the essential oil and CO2 extracts of the oriental tobacco, Prilep.Crossref | GoogleScholarGoogle Scholar |

[37]  FX Garneau, M Bouhajib, GJ Collin, M Gagnon, JW ApSimon, The glycosidically bound volatile compounds of Picea mariana (Mill.) B.S.P. J Essent Oil Res 1994, 6, 43.
         | The glycosidically bound volatile compounds of Picea mariana (Mill.) B.S.P.Crossref | GoogleScholarGoogle Scholar |

[38]  C Formisano, F Senatore, M Bruno, G Bellone, Chemical composition and antimicrobial activity of the essential oil of Phlomis ferruginea Ten. (Lamiaceae) growing wild in Southern Italy. Flavour Fragr J 2006, 21, 848.
         | Chemical composition and antimicrobial activity of the essential oil of Phlomis ferruginea Ten. (Lamiaceae) growing wild in Southern Italy.Crossref | GoogleScholarGoogle Scholar |

[39]  J Ledauphin, H Guichard, J-F Saint-Clair, B Picoche, D Barillier, Chemical and sensorial aroma characterization of freshly distilled calvados. 2. identification of volatile compounds and key odorants. J Agric Food Chem 2003, 51, 433.
         | Chemical and sensorial aroma characterization of freshly distilled calvados. 2. identification of volatile compounds and key odorants.Crossref | GoogleScholarGoogle Scholar |

[40]  J-S Kim, HY Chung, GC-MS analysis of the volatile components in dried boxthorn (Lycium chinensis) fruit. J Korean Soc Appl Biol Chem 2009, 52, 516.
         | GC-MS analysis of the volatile components in dried boxthorn (Lycium chinensis) fruit.Crossref | GoogleScholarGoogle Scholar |

[41]  M Povolo, V Pelizzola, D Ravera, G Contarini, Significance of the nonvolatile minor compounds of the neutral lipid fraction as markers of the origin of dairy products. J Agric Food Chem 2009, 57, 7387.
         | Significance of the nonvolatile minor compounds of the neutral lipid fraction as markers of the origin of dairy products.Crossref | GoogleScholarGoogle Scholar |

[42]  Andriamaharavo NR. Retention Data. NIST Mass Spectrometry Data Center; 2014.

[43]  B Marongiu, A Piras, S Porcedda, E Tuveri, A Maxia, Isolation of Seseli bocconi Guss., subsp. praecox Gamisans (Apiaceae) volatile oil by supercritical carbon dioxide extraction. Nat Prod Res 2006, 20, 820.
         | Isolation of Seseli bocconi Guss., subsp. praecox Gamisans (Apiaceae) volatile oil by supercritical carbon dioxide extraction.Crossref | GoogleScholarGoogle Scholar |

[44]  HJ Woerdenbag, T Windono, R Bos, S Riswan, WJ Quax, Composition of the essential oils of Kaempferia rotunda L. and Kaempferia angustifolia Roscoe rhizomes from Indonesia. Flavour Fragr J 2004, 19, 145.
         | Composition of the essential oils of Kaempferia rotunda L. and Kaempferia angustifolia Roscoe rhizomes from Indonesia.Crossref | GoogleScholarGoogle Scholar |

[45]  O Tzakou, A Said, A Farag, K Rashed, Volatile constituents of Ailanthus excelsa Roxb. Flavour Fragr J 2006, 21, 899.
         | Volatile constituents of Ailanthus excelsa Roxb.Crossref | GoogleScholarGoogle Scholar |

[46]  JK Muhlemann, A Klempien, N Dudareva, Floral volatiles: from biosynthesis to function. Plant Cell Environ 2014, 37, 1936.
         | Floral volatiles: from biosynthesis to function.Crossref | GoogleScholarGoogle Scholar |

[47]  EA Fich, NA Segerson, JKC Rose, The plant polyester cutin: biosynthesis, structure, and biological roles. Annu Rev Plant Biol 2016, 67, 207.
         | The plant polyester cutin: biosynthesis, structure, and biological roles.Crossref | GoogleScholarGoogle Scholar |

[48]  (a) C Mata-Pérez, B Sánchez-Calvo, MN Padilla, JC Begara-Morales, R Valderrama, FJ Corpas, et al. Nitro-fatty acids in plant signaling: New key mediators of nitric oxide metabolism. Redox Biol 2017, 11, 554.
         | Nitro-fatty acids in plant signaling: New key mediators of nitric oxide metabolism.Crossref | GoogleScholarGoogle Scholar |
      (b) M He, N-Z Ding, Plant unsaturated fatty acids: multiple roles in stress response. Front Plant Sci 2020, 11, 562785.
         | Plant unsaturated fatty acids: multiple roles in stress response.Crossref | GoogleScholarGoogle Scholar |

[49]  A Hammerbacher, TA Coutinho, J Gershenzon, Roles of plant volatiles in defence against microbial pathogens and microbial exploitation of volatiles. Plant Cell Environ 2019, 42, 2827.
         | Roles of plant volatiles in defence against microbial pathogens and microbial exploitation of volatiles.Crossref | GoogleScholarGoogle Scholar |

[50]  X Chen, H Chen, JS Yuan, TG Köllner, Y Chen, Y Guo, et al. The rice terpene synthase gene OsTPS19 functions as an (S)-limonene synthase in planta, and its overexpression leads to enhanced resistance to the blast fungus Magnaporthe oryzae. Plant Biotechnol J 2018, 16, 1778.
         | The rice terpene synthase gene OsTPS19 functions as an (S)-limonene synthase in planta, and its overexpression leads to enhanced resistance to the blast fungus Magnaporthe oryzae.Crossref | GoogleScholarGoogle Scholar |

[51]  V Ninkovic, R Glinwood, AG Ünlü, S Ganji, CR Unelius, Effects of methyl salicylate on host plant acceptance and feeding by the aphid Rhopalosiphum padi. Front Plant Sci 2021, 12, 710268.
         | Effects of methyl salicylate on host plant acceptance and feeding by the aphid Rhopalosiphum padi.Crossref | GoogleScholarGoogle Scholar |

[52]  S-W Park, E Kaimoyo, D Kumar, S Mosher, DF Klessig, Methyl salicylate Is a critical mobile signal for plant systemic acquired resistance. Science 2007, 318, 113.
         | Methyl salicylate Is a critical mobile signal for plant systemic acquired resistance.Crossref | GoogleScholarGoogle Scholar |

[53]  S-L Wee, T Peek, AR Clarke, The responsiveness of Bactrocera jarvisi (Diptera: Tephritidae) to two naturally occurring phenylbutaonids, zingerone and raspberry ketone. J Insect Physiol 2018, 109, 41.
         | The responsiveness of Bactrocera jarvisi (Diptera: Tephritidae) to two naturally occurring phenylbutaonids, zingerone and raspberry ketone.Crossref | GoogleScholarGoogle Scholar |

[54]  BL Hanssen, SJ Park, JE Royer, JF Jamie, PW Taylor, IM Jamie, Systematic Modification of Zingerone Reveals Structural Requirements for Attraction of Jarvis’s Fruit Fly. Sci Rep 2019, 9, 19332.
         | Systematic Modification of Zingerone Reveals Structural Requirements for Attraction of Jarvis’s Fruit Fly.Crossref | GoogleScholarGoogle Scholar |

[55]  PC Stevenson, SW Nicolson, GA Wright, Plant secondary metabolites in nectar: impacts on pollinators and ecological functions. Funct Ecol 2017, 31, 65.
         | Plant secondary metabolites in nectar: impacts on pollinators and ecological functions.Crossref | GoogleScholarGoogle Scholar |

[56]  Vargas RI, Shelly TE, Leblanc L, Piñero JC. Chapter Twenty-Three - Recent Advances in Methyl Eugenol and Cue-Lure Technologies for Fruit Fly Detection, Monitoring, and Control in Hawaii. In: Litwack G, editor. Vitam Horm. Vol. 83. Academic Press; 2010. pp. 575–95.

[57]  D Jenke, A Odufu, Utilization of internal standard response factors to estimate the concentration of organic compounds leached from pharmaceutical packaging systems and application of such estimated concentrations to safety assessment. J Chromatogr Sci 2012, 50, 206.
         | Utilization of internal standard response factors to estimate the concentration of organic compounds leached from pharmaceutical packaging systems and application of such estimated concentrations to safety assessment.Crossref | GoogleScholarGoogle Scholar |