Chemical Composition and Aroma Evaluation of Essential Oils from Evolvulus alsinoides L.

The aim of this study was to investigate the chemical composition and the odor‐active compounds of the essential oils from Evolvulus alsinoides, which is a well‐known edible and medicinal plant. The volatile compounds in the oils were identified by hydrodistillation (HD) and solvent‐assisted flavor evaporation (SAFE) in combination with GC, GC/MS, GC/O (=olfactometry), aroma extract dilution analysis (AEDA), and relative flavor activities (RFA values). The most abundant compound in the HD oil was cis‐α‐necrodol (12.62%), an irregular monoterpene with a cyclopentane skeleton, which is very unusual in the plant kingdom. In the SAFE oil, the main components included 2‐butoxyethanol (9.01%), benzyl alcohol (8.01%), and γ‐butyrolactone (7.37%). Through sensory analysis, 21 aroma‐active compounds were identified by GC/O. The most intense aroma‐active compounds in the HD oil were hexan‐1‐ol and γ‐nonalactone, both of which showed high RFA values. α‐Methyl‐γ‐butyrolactone and dimethyl sulfone contributed more strongly to the aroma of the SAFE oil. These results imply that the essential oils of E. alsinoides deserve further investigation in the food industry.     

Chemical Composition and Character Impact Odorants in Volatile Oils from Edible Mushrooms

The aim of this study was to investigate the chemical composition and the odor‐active components of volatile oils from three edible mushrooms, Pleurotus ostreatus, Pleurotus eryngii, and Pleurotus abalonus, which are well‐known edible mushrooms. The volatile components in these oils were extracted by hydrodistillation and identified by GC/MS, GC‐olfactometry (GC‐O), and aroma extract dilution analysis (AEDA). The oils contained 40, 20, and 53 components, representing 83.4, 86.0, and 90.8% of the total oils in P. ostreatus, P. eryngii, and P. abalonus, respectively. Odor evaluation of the volatile oils from the three edible mushrooms was also carried out using GC‐O, AEDA, and odor activity values, by which 13, eight, and ten aroma‐active components were identified in P. ostreatus, P. eryngii, and P. abalonus, respectively. The most aroma‐active compounds were C₈‐aliphatic compounds (oct‐1‐en‐3‐ol, octan‐3‐one, and octanal) and/or C₉‐aliphatic aldehydes (nonanal and (2E)‐non‐2‐enal).     

Volatile Compounds of Viola odorata Absolutes: Identification of Odorant Active Markers to Distinguish Plants Originating from France and Egypt

Absolutes isolated from Viola odorata leaves, valuable materials for the flavor and fragrance industry, were studied. Violets are mainly cultivated in France and Egypt and extracted locally. The absolutes of the two origins showed different olfactory profiles both in top and heart notes, as evidenced by sensory analysis. The aims of this study were i) to characterize the volatile compounds, ii) to determine the odorant‐active ones, and iii) to identify some markers of the plant origin. Two complementary analytical methods were used for these purposes, i.e., headspace solid‐phase microextraction (HS‐SPME) using different fiber coatings followed by GC/MS analysis and gas chromatography – olfactometry/mass spectrometry (GC‐O/MS) applied to violet leaf extracts. From a total of 70 identified compounds, 61 have never been reported so far for this species, 17 compounds were characterized by both techniques (with seven among them known from the literature), 23 compounds were solely identified by HS‐SPME GC/MS (among them only two being already mentioned as components of violet absolutes in the literature), and, finally, 30 compounds were only identified by GC‐O/MS. According to the HS‐SPME GC/MS analyses, ethyl hexanoate and (2E,6Z)‐nona‐2,6‐dienol were specific volatile compounds of the sample with French origin, while (E,E)‐hepta‐2,4‐dienal, hexanoic acid, limonene, tridecane, and eugenol were specific of the samples with Egyptian origin. Additional compounds that were not detected by HS‐SPME GC/MS analysis were revealed by GC‐O analyses, some of them being markers of origin. Pent‐1‐en‐3‐ol, 3‐methylbut‐2‐enal, 2‐methoxy‐3‐(1‐methylethyl)pyrazine, 4‐ethylbenzaldehyde, β‐phenethyl formate, and 2‐methoxy‐3‐(2‐methylpropyl)pyrazine revealed to be odorant markers of the French sample, whereas cis‐rose oxide, trans‐rose oxide, and 3,5,5‐trimethylcyclohex‐2‐enone were odorant markers of the Egyptian samples.     

Chemical Composition Variability of Essential Oils of Daucus gracilis Steinh. from Algeria

The chemical compositions of 20 Algerian Daucus gracilis essential oils were investigated using GC‐FID, GC/MS, and NMR analyses. Altogether, 47 compounds were identified, accounting for 90 – 99% of the total oil compositions. The main components were linalool ( 18 ; 12.5 – 22.6%), 2‐methylbutyl 2‐methylbutyrate ( 20 ; 9.2 – 20.2%), 2‐methylbutyl isobutyrate ( 10 ; 4.2 – 12.2%), ammimajane ( 47 ; 2.6 – 37.1%), (E)‐β‐ocimene ( 15 ; 0.2 – 12.8%) and 3‐methylbutyl isovalerate ( 19 ; 3.3 – 9.6%). The chemical composition of the essential oils obtained from separate organs was also studied. GC and GC/MS analysis of D. gracilis leaves and flowers allowed identifying 47 compounds, amounting to 92.3% and 94.1% of total oil composition, respectively. GC and GC/MS analysis of D. gracilis leaf and flower oils allowed identifying linalool (22.7%), 2‐methylbutyl 2‐methylbutyrate (18.9%), 2‐methylbutyl isovalerate (13.6%), ammimajane (10.4%), 3‐methylbutyl isovalerate (10.3%), (E)‐β‐ocimene (8.4%) and isopentyl 2‐methylbutyrate (8.1%) as main components. The chemical variability of the Algerian oil samples was studied using statistical analysis, which allowed the discrimination of three main Groups. A direct correlation between the altitudes, nature of soils and the chemical compositions of the D. gracilis essential oils was evidenced.     

Evaluation of aroma active compounds in <Emphasis Type="Italic">Tuber</Emphasis> fruiting bodies by gas chromatography–olfactometry in combination with aroma reconstitution and omission test

The aroma active compounds of three Tuber fruiting bodies (i.e., Tuber himalayense, Tuber indicum, and Tuber sinense) were firstly systematically evaluated by instrumental gas chromatography–olfactometry combining with quantitative analysis, aroma reconstitution, and omission tests. Twelve aroma active compounds were characterized by aroma extract dilution analysis, and 3-(methylthio) propanal, 3-methylbutanal, and 1-octen-3-ol with the highest flavor dilution (FD) factor (i.e., 1,024–2,048) were suggested as key contributors to the aroma. Odor activity value (OAV) was employed to determine the relative contribution of each compound to the aroma, and the compound with the highest FD factor also had the highest OAV (i.e., 10,234–242,951). Then, the synthetic blends of odorants (aroma reconstitution) were prepared with OAV larger than 15, and their aromas were very similar to the originals. Omission tests were carried out to verify the significance of 3-(methylthio) propanal, 1-octen-3-ol, and 3-methylbutanal as key compounds in the aroma of tested Tuber fruiting bodies.     

Odor-active constituents in fresh pineapple (Ananas comosus [L.] Merr.) by quantitative and sensory evaluation

By application of aroma extract dilution analysis (AEDA) to an aroma distillate prepared from fresh pineapple using solvent-assisted flavor evaporation (SAFE), 29 odor-active compounds were detected in the flavor dilution (FD) factor range of 2 to 4,096. Quantitative measurements performed by stable isotope dilution assays (SIDA) and a calculation of odor activity values (OAVs) of 12 selected odorants revealed the following compounds as key odorants in fresh pineapple flavor: 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDF; sweet, pineapple-like, caramel-like), ethyl 2-methylpropanoate (fruity), ethyl 2-methylbutanoate (fruity) followed by methyl 2-methylbutanoate (fruity, apple-like) and 1-(E,Z)-3,5-undecatriene (fresh, pineapple-like). A mixture of these 12 odorants in concentrations equal to those in the fresh pineapple resulted in an odor profile similar to that of the fresh juice. Furthermore, the results of omission tests using the model mixture showed that HDF and ethyl 2-methylbutanoate are character impact odorants in fresh pineapple.     

Evaluation of Characteristic Aroma Compounds of Citrus natsudaidai Hayata (Natsudaidai) Cold-Pressed Peel Oil

The characteristic aroma compounds of Citrus natsudaidai Hayata essential oil were evaluated by a combination of instrumental and sensory methods. Sixty compounds were identified and quantified, accounting for 94.08% of the total peel oil constituents. Limonene was the most abundant compound (80.68%), followed by γ-terpinene (5.30%), myrcene (2.25%) and α-pinene (1.30%). Nineteen compounds which could not be identified in the original oil were identified in the oxygenated fraction. Myrcene, linalool, α-pinene, β-pinene, limonene, nonanal, γ-terpinene, germacrene D, and perillyl alcohol were the active aroma components (FD-factor > 3⁶), whereas β-copaene, cis-sabinene hydrate and 1-octanol were suggested as characteristic aroma compounds, having a Natsudaidai-like aroma in the GC effluent. Three other compounds, heptyl acetate, (E)-limonene oxide and 2,3-butanediol, which each showed a high RFA value (>35) were considered to be important in the reconstruction of the original Natsudaidai oil from pure odor chemicals. The results indicate that 1-octanol was the aroma impact compound of C. natsudaidai Hayata peel oil.     

Composition and Chemical Variability of Cleistopholis patens Trunk Bark Oil from Côte d'Ivoire

The chemical composition of trunk bark oil from Cleistopholis patens (Benth .) Engl . & Diels , growing wild in Côte d'Ivoire, has been investigated by GC (FID) in combination with retention indices, GC/MS and ¹³C‐NMR. Moreover, one oil sample has been subjected to CC and all the fractions analyzed by GC (RI) and ¹³C‐NMR. In total, 61 components have been identified, including various sesquiterpene esters scarcely found in essential oils. ¹³C‐NMR was particularly efficient for the identification of a component not eluted on GC and for the quantification of heat‐sensitive compounds. Then, 36 oil samples, isolated from trunk bark harvested in six Ivoirian forests have been analyzed. The content of the main components varied drastically from sample to sample: (E)‐β‐caryophyllene (0.4 – 69.1%), β‐pinene (0 – 57%), α‐phellandrene (0 – 33.2%), α‐pinene (0.1 – 30.6%), β‐elemol (0.1 – 29.9%), germacrene D (0 – 25.4%), juvenile hormone III (0 – 22.9%), germacrene B (0 – 20.6%) and sabinene (tr‐20.3%). Statistical analysis, hierarchical clustering and principal components analysis, carried out on the 36 compositions evidenced a fair chemical variability of the stem bark oil of this species. Indeed, three clusters have been distinguished: the composition of group I (ten samples) was dominated by β‐pinene and α‐pinene, group II (nine samples) was represented by α‐phellandrene and p‐cymene and group III (16 samples) by β‐elemol. A sample displayed an atypical composition dominated by (E)‐β‐caryophyllene.     

Aroma Profile of Rubus ulmifolius Flowers and Fruits During Different Ontogenetic Phases

The chemical composition of spontaneous volatile emission from Rubus ulmifolius flowers and fruits during different stages of development was evaluated by HS‐SPME‐GC/MS. In total, 155 chemical compounds were identified accounting 84.6 – 99.4% of whole aroma profile of flowers samples and 92.4 – 96.6% for fruit samples. The main constituents were α‐copaene, β‐caryophyllene, germacrene D, (E,E)‐α‐farnesene, 1,7‐octadien‐3‐one,2‐methyl‐6‐methylene, tridecane, (E)‐2‐hexenol acetate, (E)‐3‐hexenol acetate and cyperene. The results give a chemotaxonomic contribution to the characterization of the VOCs emitted from flowers and fruits during their ontogenic development.     

Imidazole dipeptides can quench toxic 4‐oxo‐2(E)‐nonenal: Molecular mechanism and mass spectrometric characterization of the reaction products

Imidazole dipeptides, such as carnosine (β‐alanyl‐l ‐histidine) and anserine (β‐alanyl‐N^π‐methyl‐l ‐histidine), are highly localized in excitable tissues, including skeletal muscle and nervous tissue, and play important roles such as scavenging reactive oxygen species and quenching reactive aldehydes. We have demonstrated several reactions between imidazole dipeptides (namely, carnosine, and anserine) and a lipid peroxide‐derived reactive aldehyde 4‐oxo‐2(E)‐nonenal. Seven carnosine adducts and two anserine adducts were characterized using liquid chromatography/electrospray ionization‐multiple‐stage mass spectrometry. Adduct formation occurred between imidazole dipeptides and 4‐oxo‐2(E)‐nonenal mainly through Michael addition, Schiff base formation, and/or Paal‐Knorr reaction. The reactions were much more complicated than the reaction with a similar lipid peroxide‐derived reactive aldehyde, 4‐hydroxy‐2(E)‐nonenal.     

Aroma compounds in Japanese sweet rice wine (Mirin) screened by aroma extract dilution analysis (AEDA)

Thirty-nine key aroma compounds were newly identified or tentatively identified in the aroma concentrate of Japanese sweet rice wine (Mirin) by an aroma extract dilution analysis technique based on the 68 detected peaks. Among them, 3-(methylthio)propanal, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, 3-methylbutanoic acid, 2-methylbutanoic acid, and 2-methoxy-4-vinylphenol were detected with the highest FD factors in this study.     

Chemical Composition,Enantiomeric Analysis,AEDA Sensorial Evaluation and Antifungal Activity of the Essential Oil from the Ecuadorian Plant Lepechinia mutica Benth (Lamiaceae)

This study describes the GC‐FID, GC/MS, GC‐O, and enantioselective GC analysis of the essential oil hydrodistilled from leaves of Lepechinica mutica (Lamiaceae), collected in Ecuador. GC‐FID and GC/MS analyses allowed the characterization and quantification of 79 components, representing 97.3% of the total sample. Sesquiterpene hydrocarbons (38.50%) and monoterpene hydrocarbons (30.59%) were found to be the most abundant volatiles, while oxygenated sesquiterpenes (16.20%) and oxygenated monoterpenes (2.10%) were the minor components. In order to better characterize the oil aroma, the most important odorants, from the sensorial point of view, were identified by Aroma Extract Dilution Analysis (AEDA) GC‐O. They were α‐Pinene, β‐Phellandrene, and Dauca‐5,8‐diene, exhibiting the characteristic woody, herbaceus, and earthy odors, respectively. Enantioselective GC analysis of L. mutica essential oil revealed the presence of twelve couples and two enantiomerically pure chiral monoterpenoids. Their enantiomeric excesses were from a few percent units to 100%. Moreover, the essential oil exhibited moderate in vitro activity against five fungal strains, being especially effective against M. canis, which is a severe zoophilic dermatophyte causal agent of pet and human infections.     

Key compounds contributing to the fruity aroma characterization in Japanese raw soy sauce

In order to clarify the aroma characteristics of raw soy sauce (RS), the application of gas chromatography?olfactometry analysis to the aroma concentrate from a RS revealed 76 aroma peaks, of which 25 peaks showed fruit-like aromas. Furthermore, the head space aromatic compounds of RS were analyzed with 32 peaks detected. Ethyl 2-methylpropanoate, ethyl butanoate, ethyl 2-methylbutanoate, ethyl 3-methylbutanoate, and ethyl 4-methylpentanoate were detected with higher flavor dilution factor (FD factor) than other aroma compounds by aroma extract dilution analysis. Quantitative analysis suggested that these compounds were common in all RS samples tested in this study, and were present at higher concentrations than their perception thresholds. The concentrations and the FD factors of these compounds were significantly decreased during the heating of the RS. Fruitiness is one of the key aroma characteristics of RS and the ethyl esters identified in this study are the key components contributing to this distinct aroma.     

Volatile Methyl Esters of Medium Chain Length from the Bacterium Chitinophaga Fx7914

The analysis of the volatiles released by the novel bacterial isolate Chitinophaga Fx7914 revealed the presence of ca. 200 compounds including different methyl esters. These esters comprise monomethyl‐ and dimethyl‐branched, saturated, and unsaturated fatty acid methyl esters that have not been described as bacterial volatiles before. More than 30 esters of medium C‐chain length were identified, which belong to five main classes, methyl (S)‐2‐methylalkanoates (class A), methyl (S)‐2,(ω?1)‐dimethylalkanoates (class B), methyl 2,(ω?2)‐dimethylalkanoates (class C), methyl (E)‐2‐methylalk‐2‐enoates (class D), and methyl (E)‐2,(ω?1)‐dimethylalk‐2‐enoates (class E). The structures of the compounds were verified by GC/MS analysis and synthesis of the target compounds as methyl (S)‐2‐methyloctanoate ( 28 ), methyl (S)‐2,7‐dimethyloctanoate ((S)‐ 43 ), methyl 2,6‐dimethyloctanoate ( 49 ), methyl (E)‐2‐methylnon‐2‐enoate ( 20a ), and methyl (E)‐2,7‐dimethyloct‐2‐enoate ( 41a ). Furthermore, the natural saturated 2‐methyl‐branched methyl esters showed (S)‐configuration as confirmed by GC/MS experiments using chiral phases. Additionally, the biosynthetic pathway leading to the methyl esters was investigated by feeding experiments with labeled precursors. The Me group at C(2) is introduced by propanoate incorporation, while the methyl ester is formed from the respective carboxylic acid by a methyltransferase using S‐adenosylmethionine (SAM).     

Electrophysiological responses of Batocera horsfieldi (Hope) adults to plant volatiles

The olfactory stimuli from the maturation feeding‐plant, Rosa multiflora Thunb., and larval‐host plant, Populus deltoides, of the longhorned beetle, Batocera horsfieldi (Hope), were investigated by using TCT‐GC/MS (Thermal desorption and cold trap, and GC/MS) and electroantennogram recordings (EAG). A total of 20 plant compounds were identified from plant headspace volatile, including aliphatic, aromatic and terpenoid compounds. Five compounds were common to both plants. Eight compounds eliciting strong EAG response were E‐3‐hexenyl acetate, 3‐carene, 1‐penten‐3‐ol, 3‐pentanol, Z‐2‐penten‐1‐ol, hexanal and E‐2‐hexenal. Female and male B. horsfieldi exhibited broad overlap in their EAG responses to individual plant odour, and there was no clear pattern of difference between responses of female and male antennae to different compounds. Mating status had little effect on the EAG responses of females.     

Occurrence of Melibiose‐Containing Glycosphingolipids in a Sample of a Sponge‐Coral Association (Desmapsamma anchorata/Carijoa riisei)

In our research on biologically active compounds from Vietnamese marine invertebrates, rare melibiose‐containing glycosphingolipids were found in a sample of a sponge‐coral association (Desmapsamma anchorata/Carijoa riisei). Melibiosylceramides were analyzed as constituents of some multi‐component RP‐HPLC fractions, and the structures of 14 new ( 1b , 3b , 4a – 4c , 6a – 6c , 8b , 9a , 9b , 10b , 11a , 11b ) and five known ( 2b , 5a – 5c , 7b ) natural compounds were elucidated using NMR, mass spectrometry, optical rotation, and chemical transformations. These α‐d ‐Galp‐(1→6)‐β‐d ‐Glcp‐(1 1)‐ceramides (presumably sponge‐derived compounds) were shown to contain phytosphingosine‐type n‐t17:0 ( 1 ), (6E)‐n‐t17:1 ( 2 ), i‐t17:0 ( 3 ), n‐t18:0 ( 4 ), (6E)‐n‐t18:1 ( 5 ), i‐t18:0 ( 6 ), (6E)‐i‐t18:1 ( 7 ), i‐t19:0 ( 8 ), (6E)‐i‐t19:1 ( 9 ), ai‐t19:0 ( 10 ), and (6E)‐ai‐t19:1 ( 11 ) backbones N‐acylated with saturated straight‐chain (2R)‐2‐hydroxy C₂₁ ( a ), C₂₂ ( b ), and C₂₃ ( c ) acids. Characteristic trends in the fragmentations of the terminal parts of tetraacetylated normal‐chain and iso‐ and anteiso‐branched sphingoid bases were observed using GC/MS. The total sum of melibiosylceramides and compound 5b caused a reduction in colony formation of human melanoma cells.     

New co‐attractants synergizing attraction of Cetonia aurata aurata and Potosia cuprea to the known floral attractant

To improve the efficiency of the known floral attractant of Cetonia aurata aurata and Potosia cuprea [3‐methyl eugenol, 1‐phenylethanol and (E)‐anethol] electroantennographic tests were conducted using the antennae of both species. Among synthetic floral compounds eliciting the highest responses from the antennae, geraniol, (±)‐lavandulol and ß‐ionone, were chosen for field experiments. In field trapping tests in Hungary the addition of (±)‐lavandulol to the known attractant resulted in significantly higher catches of both scarabs than the ternary blend alone or the single compounds. Only geraniol resulted in higher catches of P. cuprea when added to the ternary attractant. The addition of ß‐ionone to the known attractant decreased catches. In further tests the addition of geraniol in the same single dispenser as the known ternary mixture plus (±)‐lavandulol did not increase catches of C. a. aurata and P. cuprea. The improved bait consisting of 3‐methyl eugenol/1‐phenylethanol/(E)‐anethol/(±)‐lavandulol described in this study is recommended for use in trapping of C. a. aurata and P. cuprea for agricultural purposes.     

Odour quality discrimination for behavioural antagonist compounds in three tortricid species

The antennal and behavioural response of three tortricid species (Lepidoptera: Tortricidae) to their corresponding sex pheromones and known or putative behavioural antagonists was tested by electroantennography and in field trials. The species and their pheromones and known or proposed behavioural antagonist were lightbrown apple moth, Epiphyas postvittana (Walker) [pheromone: 95% (E)‐11‐tetradecenyl acetate (E11‐14Ac) and 5% (E,E)‐9,11‐tetradecadienyl acetate (E9E11‐14Ac); antagonist: (Z)‐11‐tetradecenyl acetate (Z11‐14Ac)], codling moth, Cydia pomonella (L.) [pheromone: (E,E)‐8,10‐dodecadien‐1‐ol (codlemone); antagonist: (E,E)‐8,10‐dodecadienyl acetate (codlemone acetate)], and gorse pod moth, Cydia ulicetana (Haworth) [pheromone: (E,E)‐8,10‐dodecadienyl acetate (codlemone acetate); putative antagonist: (E,E)‐8,10‐dodecadien‐1‐ol (codlemone)]. In all three species, the antennal response to the antagonists was not significantly different from the antennal response to con‐specific sex pheromone compounds. In the field trapping experiments, significantly fewer males of all three species were attracted to the respective pheromone when blended with the behavioural antagonist compound. However, this response varied between the species, with lightbrown apple moth and codling moth showing stronger responses to the antagonist compounds than gorse pod moth. Both lightbrown apple moth and codling moth males were able to discriminate between pure pheromone and pheromone blended with the antagonist when placed in traps side‐by‐side separated by ca. 10 cm. The presence of the behavioural antagonist not only affected the catch of males of both species within their own traps but also affected the catch in the neighbouring trap that contained con‐specific sex pheromone; the catch of gorse pod moth was not reduced by the presence of codlemone in the neighbouring trap. These results suggest that strong behavioural antagonists such as codlemone acetate for codling moth and Z11‐14Ac for lightbrown apple moth induce their inhibition effect at a substantial distance downwind from the odour source; however, most of those males that were able to overcome this inhibition effect at the early stage of orientation to odour source, were able to discriminate between the pheromone source and the pheromone source admixed with behavioural antagonist. Moderate behavioural antagonists such as codlemone for gorse pod moth did not elicit a discrimination effect.     

Chemoreception of host volatiles in the bark beetleIps typographus

Summary In the bark beetleIps typographus the stimulating effects of host odour constituents were studied by linking a gas Chromatograph (GC) with electrophysiological recordings from single olfactory receptor cells. Cells were exposed to the complete aroma of natural bark, extracts from host and non-host trees and fractions of these stimuli separated via a GC column. Four minor fractions belonging to two extracts were found to excite olfactory receptor cells. Responsive cells were divided into two main groups reacting exclusively to one fraction and suggesting that the cells were highly specialized to a particular host odour constituent. However, an effective extract or fraction could not be found for half of the olfactory units responding to natural bark, indicating that the relevant stimulatory compounds were lost during the extraction and/or GC procedure.Abbreviations EAG electroantennogram - GC gas-chromatograph     

Genetic control of α‐farnesene production in apple fruit and its role in fungal pathogenesis

Terpenes are important compounds in plant trophic interactions. A meta‐analysis of GC‐MS data from a diverse range of apple (Malus × domestica) genotypes revealed that apple fruit produces a range of terpene volatiles, with the predominant terpene being the acyclic branched sesquiterpene (E,E)‐α‐farnesene. Four quantitative trait loci (QTLs) for α‐farnesene production in ripe fruit were identified in a segregating ‘Royal Gala’ (RG) × ‘Granny Smith’ (GS) population with one major QTL on linkage group 10 co‐locating with the MdAFS1 (α‐farnesene synthase‐1) gene. Three of the four QTLs were derived from the GS parent, which was consistent with GC‐MS analysis of headspace and solvent‐extracted terpenes showing that cold‐treated GS apples produced higher levels of (E,E)‐α‐farnesene than RG. Transgenic RG fruit downregulated for MdAFS1 expression produced significantly lower levels of (E,E)‐α‐farnesene. To evaluate the role of (E,E)‐α‐farnesene in fungal pathogenesis, MdAFS1 RNA interference transgenic fruit and RG controls were inoculated with three important apple post‐harvest pathogens [Colletotrichum acutatum, Penicillium expansum and Neofabraea alba (synonym Phlyctema vagabunda)]. From results obtained over four seasons, we demonstrate that reduced (E,E)‐α‐farnesene is associated with decreased disease initiation rates of all three pathogens. In each case, the infection rate was significantly reduced 7 days post‐inoculation, although the size of successful lesions was comparable with infections on control fruit. These results indicate that (E,E)‐α‐farnesene production is likely to be an important factor involved in fungal pathogenesis in apple fruit.