Next Article in Journal
The Self-Aggregation of Porphyrins with Multiple Chiral Centers in Organic/Aqueous Media: The Case of Sugar- and Steroid-Porphyrin Conjugates
Next Article in Special Issue
The Application of Lamiaceae Lindl. Promotes Aroma Compounds Formation, Sensory Properties, and Antioxidant Activity of Oat and Buckwheat-Based Cookies
Previous Article in Journal
Spectroscopic and In Vitro Investigations of Boron(III) Complex with Meso-4-Methoxycarbonylpropylsubstituted Dipyrromethene for Fluorescence Bioimaging Applications
Previous Article in Special Issue
Evaluation of the Perceptual Interactions among Aldehydes in a Cheddar Cheese Matrix According to Odor Threshold and Aroma Intensity
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molecules
Volume 25
Issue 19
10.3390/molecules25194543
molecules-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles thumb_up
...
Endorse textsms
...
Comment
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Article

Volatile Compounds and Physicochemical Quality of Four Jabuticabas (Plinia sp.)

by
Thais Pádua Freitas
1,
Isabela Barroso Taver
1,
Poliana Cristina Spricigo
1,
Lucas Bueno do Amaral
2,
Eduardo Purgatto
2 and
Angelo Pedro Jacomino
1,*
1
Department of Crop Science, University of São Paulo (USP), Piracicaba 13418-900, Brazil
2
Department of Food Science, University of São Paulo (USP), São Paulo 05508-000, Brazil
*
Author to whom correspondence should be addressed.
Molecules 2020, 25(19), 4543; https://doi.org/10.3390/molecules25194543
Submission received: 10 July 2020 / Revised: 14 September 2020 / Accepted: 16 September 2020 / Published: 3 October 2020
(This article belongs to the Special Issue Volatile Compounds and Smell Chemicals (Odor and Aroma) of Food—Second Edition)
Browse Figures
Versions Notes

Abstract

:
The jabuticaba is a native Brazilian fruit that has aroused worldwide interest in terms of its nutritional composition and biological activity. However, research on the profile of volatile compounds (VOCs) emitted by these fruits is rare. This study presents the first identification of VOCs from four jabuticaba species. The aim of the study was to characterize the aromatic profile of the following species: ‘Sabará’ (Plinia jaboticaba), ‘Escarlate’ (Plinia phitrantha × Plinia cauliflora), ‘Otto Andersen’ (Plinia cauliflora), and ‘Esalq’ (Plinia phitrantha). The analysis was performed by headspace solid-phase microextraction combined with gas chromatography/mass spectrometry (SPME-GC-MS). Multivariate analysis techniques applying the partial least squares-discriminant analysis (PLS-DA) and heatmap were used to compare the results. Fruit quality parameters were determined in terms of fresh mass (g), skin color, soluble solids, and titratable acidity. A total of 117 VOCs was identified including terpenoids, esters, alcohols, aldehydes, alkanes, ketones, and carboxylic acids, with 36 VOCs common to all four species. Terpenes were the majority for all jabuticabas with smaller contributions from other volatile classes, especially β-cubebene, β-elemene, and D-limonene for the ‘Otto Andersen’ jabuticaba.
Keywords:
postharvest; aroma; SPME

1. Introduction

Jabuticaba (Plinia sp.) is a native Brazilian fruit belonging to the botanical family Myrtaceae, naturally occurring in the Atlantic Rainforest biome. This fruit is a globose berry about 2.0 to 3.5 cm in diameter, which develops attached to the stem. When ripe, its skin may display various colors, such as red, dark purple, and black. The pulp has a pleasant taste and is white, gelatinous, sweet exhibiting low acidity, and may contain from one to four seeds [1,2]. Currently, about nine species of jabuticaba are known, as well as some varieties, among them Plinia jaboticaba, Plinia cauliflora, Plinia trunciflora, Plinia coronate, and Plinia phitrantha [3]. The jabuticaba has aroused the interest of the food industry, due to the presence of high content of compounds exhibiting antioxidant, anti-inflammatory, and anti-hypercholesterolemic activities, mainly anthocyanins and tannins [4,5,6].
‘Sabará’ jabuticabas (Plinia jaboticaba) are the most cultivated in Brazil. The fruit is black, with a thin and smooth skin, and a very sweet flavor. The ‘Escarlate’ (Plinia phitrantha × Plinia cauliflora) jabuticaba presents side fruits [7], with a scarlet-red color, juicy, and sweet pulp. Fruits belonging to the ‘Otto Andersen’ (Plinia cauliflora) species are black, with abundant pulps and very sweet. The ‘Esalq’ (Plinia phitrantha) jabuticaba is one of the largest of their kind, reaching up to 4 cm in diameter. It is a species developed by the “Luiz de Queiroz” School of Agriculture hence its name, ‘Esalq’. It ranges from reddish to vinaceous, with a sweet and velvety pulp.
Alongside nutritional characteristics and an attractive appearance, the fruit quality perception is determined by fruit volatile organic compound (VOC) profiles [8]. The differential emission of VOCs changes mainly in relation to the interaction of plant organs with their environment, and in the case of fruits, will develop according to the maturation progress [9]. This volatile composition creates an olfactory identity specific to each fruit species and may be applied to distinguish fruits within the same species. Varieties and/or accessions belonging to the same species can share and contain exclusive compounds, which will potentially influence their consumption preference. The VOC profile variability in accessions of the same species has been reported for uvaias, another native Atlantic Rainforest fruit [10].
Volatile monoterpenes such as β-ocymene and linalool, as well as sesquiterpene δ-cadinene, have been described for Plinia cauliflora and Plinia trunciflora [11]. Terpenes have been described as an abundant class of volatiles in Plinia jaboticaba (Vell.) O. Berg, followed by compounds classified as organic acids and alcohols [12]. It is known that the essential jabuticaba oil contains terpenes, such as α-pinene, β-pinene, 1,8-cineole, α-terpineol, and β-caryophyllene, known for their antibacterial and anti-inflammatory actions, suggesting that the same volatile compounds present in the fruit aroma are indicative of endogenous levels and potential bioactive action [13,14,15,16,17].
VOC profile descriptions for jabuticabas are scarce, especially with regard to this fruits’ diversity of species and varieties. In this context, this study is the first to address VOC characterization in ‘Sabará’ (Plinia jaboticaba), ‘Escarlate’ (Plinia phitrantha × Plinia cauliflora), ‘Otto Andersen’ (Plinia cauliflora), and ‘Esalq’ (Plinia phitrantha) jabuticabas.

2. Results and Discussion

The four jabuticaba species were characterized in terms of basic fruit quality attributes (Supplementary material Table S1). The ‘Otto Andersen’ (P. cauliflora) jabuticaba was noteworthy for presenting a greater fresh mass (11.6 ± 0.3 g), as well as a larger size compared to the other species (height: 25.7 ± 0.7 mm, diameter: 26.6 ± 0.3 mm). The same specie exhibited the highest soluble solids concentration of 19.9 ± 0.2 °Brix. This value corresponds to 1.8-fold the lowest measured value (11.2 ± 0.0 °Brix), in the ‘Sabará’ species. This index can also be compared to Crimson Seedless table grapes (Vitis vinifera) [18], considered a fruit with a markedly sweet flavor. The dark purple color of the fruit was characterized by the low hue angle and brightness for all species. The ‘Esalq’ jabuticaba is noteworthy for its lowest color angle (30.3 ± 2.2) and highest brightness (30.3 ± 1.2). The chromaticity, value a* and b* of the fruit skin were up to 3-fold lower in the ‘Otto Andersen’ and ‘Sabará’ jabuticabas in relation to the ‘Scarlet’ and ‘Esalq’ fruits.
The VOC production by the four jabuticaba species totaled 117 distinct compounds (Table 1). The partial least squares-discriminant analysis (PLS-DA) was performed to provide an overview of the aromatic profile of jabuticabas (Figure 1B and Table S2). The main contribution of the PLS-DA was the characterization of the volatile compounds emitted by each jabuticaba, indicating a characteristic aromatic profile for each of the evaluated species, however, the PLS-DA also allowed identifying groups of volatiles shared by the four jabuticabas (Figure 1A).
The principal component analysis displays each species of jabuticaba allocated in a quadrant of the factorial plane, evidencing the dissimilarity between them (Figure 1A,B). PC1 and PC2 components were responsible for 71.4% of the total data variability, being 44.7% (PC1) and 26.7% (PC2) (Figure 1A). Observing Figure 1C, it is possible to group the jabuticabas ‘Otto Andersen’ and ‘Sabará’ as well as ‘Escarlate’ and ‘Esalq’ in two groups by the similarity between the volatile compound’s profiles. Moreover, considering that ‘Escarlate’ jabuticaba is the result of a breeding of the species ‘Otto Andersen’ and ‘Esalq’, the greater influence of ‘Esalq’ on the constitution of the aromatic profile than ‘Otto Andersen’ is evident.
The ‘Sabará’ (P. jaboticaba) jabuticaba is the most common and most commercialized species in Brazil. This species presented 12 exclusive VOCs grouped in cluster 1–C1 (Figure 1B): Propyl acetate, cyclofenchene, ethyl isovalerate, ethyl 3-hexenoate, (Z)-3-hexen-1-ol acetate, butyl 2-butenoate, cyclopropanecarboxylic acid,3-methylbutyl ester, (Z)-3-hexenyl (E)-2-butenoate, nonanol, 2-phenylacetamide, n-(1-phenyl-2-propyl), citronellyl butyrate, ethyl cinnamate—most of which are esters, with descriptive notes such as fruity, green, and sweet (Table S2). Esters are widely produced in soft-fleshed fruits during ripening, with the dual function of attracting animals and protecting the fruits against pathogens [19]. Esters are also the most important VOC class in strawberries, for example, where they are responsible for over 90.0% of the ripe fruit’s aroma [20]. Acetate esters, such as (Z)-3-hexenyl acetate, are positively evaluated by consumers regarding pear acceptance in sensory analyses, and have been described in ‘Sabará’ jabuticaba [21]. Additionally, acetate esters are involved in defense mechanisms against abiotic stresses in peaches,, which may suggest that they also play this role in jabuticaba [22]. Three ethyl esters were identified exclusively in ‘Sabará’ jabuticaba. This class of compounds has been described as one of the main components of the aroma of the Passiflora genus [19]. Aliphatic esters were the major contributors to the aroma of this fruit, indicating that the lipoxygenase (LOX) pathway, which produces sequential lipid degradation, is more active than in the other assessed species. The ‘Escarlate’ jabuticaba (P. phitrantha × P. cauliflora) presented the smaller C2 comprising three compounds: α-muurolene, β-patchoulene, 3,6-dimethyl-4h-furo[3,2-c]pyran-4-one (Table S2), the sesquiterpene α-muurolene are the only one with aromatic notes described in the literature. The ‘woody-like’ aroma of this compound is widely emitted by fruits and, mainly, by flowers of different species [23,24,25,26,27]. It has also been identified in fig species, and in Ficus racemosa, characterized by being one of the volatiles emitted during the daytime, with the function of attracting pollinating wasps [28,29]. For the ‘Escarlate’ jabuticaba these sesquiterpenes contributed with 4.4% of the total aroma emitted, differentiating it from the other jabuticabas, where α-muurolene was not identified.
The group of volatiles that characterize the ‘Otto Andersen’ (P. cauliflora) jabuticaba was categorized in cluster 3. This composition was formed by ethyl propionate, d-α-pinene, ethyl-2-methyl, (E)-ethyl tiglate, cis-1,3,3-trimethylbicyclo[3.1.0]hexane-1-carboxaldehyde, cyclopentane, 1-ethyl-1-methyl, δ-selinene, l-bornyl acetate, viridiflorene, α-selinene, methyl cinnamate, methyl isoeugenol, β-eudesmol, including monoterpenes, esters, aldehydes, and alkanes, with an emphasis on the most part consisting of sesquiterpenes, sesquiterpenoid esters, and sesquiterpenoid alcohols. Among the 13 VOCs, four have no specific aromatic contribution, three display a pinus-wood-like aroma, and six add a mixture of fruity, floral, and sweet odors. The citrus aroma with a spicy touch of α-selinene sesquiterpene is the most representative component of the cluster, with 1.7% of the total profile emitted by ‘Otto Andersen’ jabuticabas. α -selinene is considered to be one of the characteristic compounds of the aroma of Myrtaceae family species [30,31,32], but has also been identified in other botanical families, such as Cyperaceae and Lamiaceae [33,34].
The VOCs α-thujene, undecane, 3-octanone, (E)-2-octenal, 2,2-dimethylhexanal, (E)-2-octen-1-ol, benzyl acetate, p-vinylbenzohydrazide, 2,9-bornanediol, and α-eudesmol occur exclusively in ‘Esalq’ jabuticaba (P. phitrantha), cluster 4 (Figure 1B). All of them were identified at mean amounts of 0.2% of the total emitted by this species, except for α-thujene (1.4%). Therefore, the most abundant aroma in this cluster was characterized by the pungent ‘green-herbal-woody’ notes attributed to α-thujene. The monoterpene was characterized in cagaita (Eugenia dysenterica) [35], eucaliptus (Eucalyptus spp.) [36], and corresponds to 70.0% of the aroma of ylang-ylang (Cananga odorata) and frankincense (Boswellia spp.), both traditionally used for therapeutic purposes [37].
The groupings C1, C2, C3, and C4 contain the differential elements that individualize the aromatic profile of the analyzed jabuticaba species (Table S1). These differences could be attributable to the species’ genetic variability, considering that all jabuticabas were grown under the same environmental conditions. On average, the compounds identified represented a small relative area when compared to the total emitted volatiles. The participation of these VOCs in the formation of jabuticaba flavor can contribute to the composition of aroma nuances, while the contribution of the aroma base may be attributed to the most abundant compounds. The compounds with a greater relative area were common to the all four species. In total, 36 VOCs belonging to various classes were identified, namely (14) sesquiterpenes, (9) sesquiterpene alcohols, (5) monoterpenes, (3) alcohols, (2) aldehydes, (1) monoterpenes alcohols, and (1) esters (Figure 2).
Terpenoids were the major volatile organic compounds in the aroma of ‘Sabará’, ‘Escarlate’, ‘Otto Andersen’, and ‘Esalq’ jabuticabas, representing 81.5% of the total, in accordance with previously reported results [5,12,38]. This result suggests that the mevalonic acid or pyruvate and 3-phosphoglycerate routes, necessary for terpene biosynthesis, are the most active pathways in mature jabuticabas in relation to the other metabolic VOC-synthesizing pathways. The differences identified for the 36 VOCs were quantitative, with some compounds being more abundant in one species compared to another. This result was similar to a study carried out with citrus species [39].
The β-cubebene sesquiterpene was the most emitted volatile compound in the analyzed jabuticabas, with the exception of ‘Otto Andersen’, where it appears as the second most emitted VOC. Its contribution to the total area in each species was of 16.8%, 17.8%, and 15.9% for the ‘Esalq’, ‘Escarlate’, and ‘Sabará’ jabuticabas, respectively. β-cubebene has a pleasant aroma translated as fruity and citrus. This compound is commonly found in the essential oils of several species [40,41] with the third most abundant member of the essential oil being obtained from cinnamon leaves (Cinnamomum osmophloeum) [42].
The fresh, herbaceous, and waxy aroma of β-elemene ranks second among the most important emissions for jabuticabas, except for ‘Otto Andersen’, where it appears in the fourth place. β -elemene is a sesquiterpene extensively studied due to its biological functions. However, the anticancer activity is by far its most relevant function. β-elemene is capable of causing apoptosis and inhibiting the proliferation of several cancer cells until the most aggressive brain tumor [43]. Currently, Curcuma wenyujin, belonging to the Zingiberaceae family, is the plant most applied to the extraction of β-elemene [44]. Our results suggest that jabuticabas, mainly the ‘Esalq’ and ‘Escarlate’ species, are a natural source of this compound, which displays the potential to be used as a raw material for its extraction, as reported for Nigella damascena [45].
D-limonene is the most abundant compound in the ‘Otto Andersen’ jabuticaba, representing 12.1% of the total emitted volatile compounds. This VOC is an important component of fragrances, used in cosmetic, pharmaceutical, and food products due to its ‘citric-like’ aroma [46] typical of oranges. This monoterpene has aroused growing interest with regard to the human health, where over sixty scientific articles have been published regarding its biological activity [47]. It exhibits an anti-inflammatory action [48], and is considered promising for the development of drugs to prevent gastric damage [49]. Other studies have reported its action, and its potential use in chemopreventive procedures against different types of cancers [50,51].
The assessed jabuticabas were characterized as displaying woody notes, due to the presence of the sesquiterpenes α-copaene, γ-elemene, humulene, γ-muurolene, δ-cadinene, γ-cadinene, α-cadinene, α-calacorene, T-cadinol, and α-cadinol. The VOCs γ-muurolene (2.2%), δ-cadinene (5.1%), and α-calacorene (0.1%), were detected in similar amounts in all species. However, compounds such as γ-elemene and humulene were 3.0-fold more present in ‘Esalq’ jabuticabas compared to the ‘Otto Andersen’, ‘Sabará’, and ‘Escarlate’ jabuticabas. These terpenes appear frequently in the aromatic profile of other Myrtaceae members, such as jambolão, pitanga, and uvaia [52,53,54].
Linalool was abundant in ‘Otto Andersen’ jabuticabas, representing 9.0% of the total emitted VOC, 4-fold higher than the average of the other three species. The amount of linalool has been related to the regulatory action of methyl jasmonate acid in other species [55,56,57,58,59]. In addition, differences in the emitted amounts may change its specific functions and interactions with linalool itself or its derivatives, due to its multifunctional nature [60]. Linalool is a sesquiterpenoid alcohol with a floral aroma emitted by flowers, fruits [61], and even fungi [62], widely used in the composition of various fragrances. It is also the key compound of the aroma of conventional fruits such as tomatoes (Solanum licopersum) [63], citrus [64], and strawberries (Fragaria × ananassa) [65].
The compounds ethyl acetate, β-ocimene, o-cymene, and ethanol were abundant in the ‘Otto Andersen’ and ‘Sabará’ jabuticabas. For ethanol, the average of these two species was 17.3-fold higher than the average of the ‘Escarlate’ and ‘Esalq’ jabuticabas.
The volatiles hexanal, α-phellandrene, hexanol, (Z)-3-hexen-1-ol, benzaldehyde, 4-terpineol, 1-epi-bicyclosesquiphellandrene, calamenene, α-calacorene, palustrol, ledol, humulane-1,6- dien-3-ol, mansonone, rosifoliol, selina-6-en-4-ol, T-cadinol, α-cadinol, juniper camphor represented less than 1% for all species. Of these VOCs with less area representativeness, hexanal and 4-terpineol were more emitted in the ‘Otto Andersen’ jabuticaba. 4-carvomenthenol is an ingredient used in cosmetics, fine fragrances, and personal care products, in addition to household cleaning products and detergents [66]. Humulane-1,6-dien-3-ol, selina-6-en-4-ol, juniper camphor, and α-cadinol were more emitted in ‘Escarlate’. Certain VOCs, such as ledol and rosifoliol were highlights for ESALQ jabuticabas. Despite the smaller relative areas these VOCs can influence the sensory and flavor characteristics perceived by consumers, if they are present in relatively low odor thresholds (part per billion, ppb).
Some odoriferous compounds have low odor detection thresholds. Among those reported for the four jabuticaba species, benzaldehyde was observed in relatively low amounts (Figure 2) but may have a significant impact on the aroma due to the low detection threshold (0.093 mg Kg−1) (Table S3). Other compounds with a low threshold of detection were identified with larger relative areas, such as D-limonene (0.04 mg Kg−1) and linalool (0.001 mg Kg−1) (Table S3).
Considering the physicochemical quality and aromatic profile of each of the jabuticabas analyzed, there is great potential and diversity to meet distinct consumer demands, and also support genetic improvement programs. The ‘Otto Andersen’ (P. cauliflora) jabuticaba stands out for its fresh mass, size, and concentration of soluble solids compared to other species. The typical dark purple color of the skin of the jabuticaba fruit was slightly more intense in the ‘Esalq’ species (P. phitrantha) and can be a positive factor in consumer choice. Regarding the composition of the aromatic profile, jabuticaba ‘Sabará’ is interesting for gathering the greatest number of exclusive esters of sweet and fruity notes. The ‘Escarlate’ jabuticaba is distinguished by the intense presence of terpenes, mainly sesquiterpenes.
Jabuticabas are recognized for the presence of bioactive compounds such as ellagitannins and anthocyanins [67], now adding the existence of significant differences in their aromatic profile. The groupings of the volatile compounds of each jabuticaba suggest that changes in the regulatory aspects of the metabolic routes of each variety occur, mainly related to the concentration and availability of substrates, the type of substrate, and enzymatic activity [68]. The volatile profile of jabuticabas is constituted mainly by terpenes, both in the number of detected compounds and in relative area abundance. Among them, β-cubebene, β-elemene, d-limonene, γ-elemene are potentially characteristic candidates of the aroma of members from the Plinia genus. Additionally, it is important to note that volatiles abundant in jabuticaba, such as monoterpene d-limonene and sesquiterpene β-elemene, exhibit therapeutic efficiency proven in several studies. Therefore, jabuticabas can be a reference for studies on new possibilities of the uses of different species, prioritizing the extraction of compounds that can benefit human health.

3. Material and Methods

3.1. Samples

The ripe jabuticabas from four varieties Sabará, Escarlate, Esalq, and Otto Andersen were harvested in November 2019 in Casa Branca, São Paulo, Brazil, latitude 21°46′26″ S, longitude 47°05′11″ W. After collection, the fruits were frozen at −20 °C and transported to the Laboratory of Postharvest of Horticultural Crops in Piracicaba, São Paulo, Brazil (LPV-ESALQ/USP). The fruits (approximately 1 kg of each jabuticaba) were selected according to the appearance, maturation stage, and absence of defects, to ensure homogeneity and uniformity and were frozen at −80 °C until analysis.

3.2. Quality Parameters

Fresh mass was determined on an analytical balance and the results expressed in grams (g). Skin color was obtained with a Minolta® CR-300 colorimeter, with two readings taken on opposite sides of each fruit. The results were expressed as color angle (° Hue), luminosity (L *), chromaticity (C *), a * coordinates and b * coordinates.
The height, diameter, and shape of the fruit were measured with a digital caliper with two readings taken at equidistant points for each attribute. The results were expressed in millimeters (mm).
The soluble solid content in the pulp was quantified using an Atago Palette PR-101 digital refractometer [69]. The results were expressed as ° Brix. The pulp’s titratable acidity was determined by the neutralization titration, using 2.0 g of filtered pulp homogenized in 18 mL of distilled water. The samples were titrated with a standard 1 N sodium hydroxide solution (NaOH) to pH 8.1 [70]. The results were expressed as % of citric acid equivalents.

3.3. Volatile Compound Determination

3.3.1. Sample Preparation

A total of 3 g of pulp and skin from 150 fruits of each species of jabuticaba were crushed in an analytical mill (IKA A11) with liquid N2 and placed in 20 mL glass flasks containing 7 mL of a 30% (w/v) NaCl solution. The flasks were then sealed with stainless steel lids with silicone septa and stored at −20 °C for GC-MS analysis.

3.3.2. GC-MS Analysis

The volatile compounds were analyzed applying the solid phase microextraction method (SPME), consisting of five replicates each [71]. The vials were thawed in a water bath at 40 °C, under agitation, for 10 min, to accumulate volatile compounds in the headspace. After the equilibrium time, the septum was punctured with a needle, allowing for exposure of the SPME fiber (divinylbenzene, carboxene, and polydimethylsiloxane 50/30 μm, Supelco, Inc., (Sigma-Aldrich, Belfonte, PA, USA)) for 50 min. Once captured, the volatile compounds were desorbed from the fiber by exposure to the heat of the chromatography injector (200 °C) for 5 min.
A Hewlett-Packard (HP) 6890 chromatograph was used for VOC detection, coupled to an HP mass spectrometer model 5973, with a Supelcowax 10 chromatographic column (30 m, 0.25 mm internal diameter, 0.25 μm film thickness). The temperature program used comprised a temperature ramp of 2 °C/min from 40 to 150 °C. The interface temperature between the chromatograph and the selective mass detector was 230 °C and ionization was performed by electron impact (70 eV) with the ion source kept at 150 °C. VOCs were identified by comparison using NIST2011, (Gaithersburg, USA) and confirmed with spectral data available at MassBank North America (MoNA: http://mona.fiehnlab.ucdavis.edu/). The retention index (IR) calculation was performed with a series of n-alkanes (C7-C30, Supelco) with the retention indices reported in the literature and with the mass spectrum of authentic external standards. A pool of the following volatile compounds external standards (Sigma-Aldrich, Belfonte, PA, USA) was prepared and injected in GC-MS to validate the identification of compounds by mass spectral comparison: Ethyl acetate; hexanal; 1-hexanol; (Z)-3-hexen-1-ol; 2-hexenal; 1-penten-3-ol; 6-methyl-5-hepten-2-one; 1-pentanol; benzaldehyde; β-myrcene; 2-phenylethanol; δ-cadinene; α-cubebene; β-caryophyllene; d-limonene; geraniol; α-phellandrene; isoamyl acetate; ethanol; 4-terpineol; β-caryophyllene oxide; camphor; humulene; γ-terpinene; α-pinene; β-pinene; ethyl butyrate.

3.4. Statistical Analyses

An analysis of variance (one-way ANOVA) and the Tukey test (p < 0.05) were applied to the physical-chemical characterization data for comparison between species—sample size (N = 5). A partial least squares-discriminant analysis (PLS-DA) and hierarchical clustering and heatmap, prepared using the Metaboanalyst 4.0 program [72] were used to verify the difference between the VOC profiles.

Supplementary Materials

The following are available online, Table S1: Physicochemical characterization of jabuticabas Sabará (Plinia jaboticaba), Escarlate (Plinia phitrantha × Plinia cauliflora), Otto Andersen (Plinia cauliflora) e Esalq (Plinia phitrantha); Table S2: Volatile aromatic compounds divided by clusters of each jabuticaba obtained by headspace solid phase microextraction combined with gas chromatography/mass spectrometry (SPME-GC-MS). C1, C2, C3, C4 indicate clusters of compounds exclusive for each species. Where: Sabara: ‘Sabará’ (Plinia jaboticaba), ESCAR: ‘Escarlate’ (Plinia phitrantha × Plinia cauliflora), OTTO: ‘Otto Andersen’ (Plinia cauliflora) and ‘Esalq’ (Plinia phitrantha)

Author Contributions

Conceptualization and design of the experiments, P.C.S. and T.P.F.; formal analysis and data curation, L.B.d.A., I.B.T., and T.P.F.; writing—original draft preparation, T.P.F. and I.B.T.; writing—review and editing, T.P.F. and P.C.S.; supervision, E.P. and A.P.J.; funding acquisition, A.P.J. and E.P. All authors have read and agreed to the published version of the manuscript.

Funding

This research was funded by the Coordination for the Improvement of Higher Education Personnel (CAPES) and the São Paulo State Research Support Foundation (FAPESP) (process number 2014/12606-3).

Acknowledgments

The authors would like to thank Adhemar Gomes da Silva Neto for supplying the fruits for the experiments.

Conflicts of Interest

The authors declare no conflict of interest.

References

  1. De Andrade Neves, N.; Stringheta, P.C.; Gómez-Alonso, S.; Hermosín-Gutiérrez, I. Flavonols and ellagic acid derivatives in peels of different species of jabuticaba (Plinia spp.) identified by HPLC-DAD-ESI/MSn. Food Chem. 2018, 252, 61–71. [Google Scholar] [CrossRef]
  2. Suguino, E.; Heiffig, L.S.; Saavedra del Aguila, J.; Minami, K. Mirtáceas com Frutos Comestíveis do Estado de São Paulo: Conhecendo Algumas Plantas, 1st ed.; ESALQ: Piracicaba, Brazil, 2006; ISBN 14144530. [Google Scholar]
  3. Pereira, M.; de Oliveira, A.L.; Pereira, R.E.D.A.; Sena, J.A.D.; da Costa, J.R.V.; de Almeida, M.; Gonçalves, A.N. Morphologic and molecular characterization of Myrciaria spp species. Rev. Bras. Frutic. 2005, 27, 507–510. [Google Scholar] [CrossRef]
  4. Salomão, L.C.C.; de Siqueira, D.L.; Aquino, C.F.; de Lins, L.C.R. Jabuticaba—Myrciaria spp. Exot. Fruits 2018, 237–244. [Google Scholar] [CrossRef]
  5. Wu, S.B.; Long, C.; Kennelly, E.J. Phytochemistry and health benefits of jaboticaba, an emerging fruit crop from Brazil. Food Res. Int. 2013, 54, 148–159. [Google Scholar] [CrossRef]
  6. Abe, L.T.; Lajolo, F.M.; Genovese, M.I. Potential dietary sources of ellagic acid and other antioxidants among fruits consumed in Brazil: Jabuticaba (Myrciaria jaboticaba (Vell.) Berg). J. Sci. Food Agric. 2012, 92, 1679–1687. [Google Scholar] [CrossRef] [PubMed]
  7. Souza, M.D.C.; Morim, M.P. Subtribos Eugeniinae O. Berg e Myrtinae O. Berg (Myrtaceae) na Restinga da Marambaia, RJ, Brasil. Acta Bot. Bras. 2008, 22, 652–683. [Google Scholar] [CrossRef]
  8. Goff, S.A.; Klee, H.J. Plant volatile compounds: Sensory cues for health and nutritional value? Science 2006, 311, 815–819. [Google Scholar] [CrossRef]
  9. Dudareva, N.; Klempien, A.; Muhlemann, J.K.; Kaplan, I. Biosynthesis, function and metabolic engineering of plant volatile organic compounds. New Phytol. 2013, 198, 16–32. [Google Scholar] [CrossRef]
  10. Silva, A.P.G.; Spricigo, P.C.; Purgatto, E.; de Alencar, S.M.; Sartori, S.F.; Jacomino, A.P. Chemical composition, nutritional value and bioactive compounds in six uvaia accessions. Food Chem. 2019, 294, 547–556. [Google Scholar] [CrossRef]
  11. da Silva, A.P.G.; Spricigo, P.C.; Purgatto, E.; de Alencar, S.M.; Jacomino, A.P. Plinia trunciflora and Plinia cauliflora: Two species rich in bioactive compounds, terpenes, and minerals. J. Food Meas. Charact. 2019, 13, 921–931. [Google Scholar] [CrossRef]
  12. Rondán, G.; Cabezas, A.; Oliveira, A.; Brousett-Minaya, M.; Narain, N. HS-SPME-GC-MS detection of volatile compounds in Myrciaria jabuticaba Fruit. Sci. Agropecu. 2018, 9, 319–327. [Google Scholar] [CrossRef] [Green Version]
  13. Li, F.; Zhang, J.; Lin, M.; Su, X.; Li, C.; Wang, H.; Li, B.; Chen, R.; Kang, J. Anti-inflammatory terpenes from Schefflera rubriflora C. J. Tseng & G. Hoo with their TNF-α and IL-6 inhibitory activities. Phytochemistry 2019, 163, 23–32. [Google Scholar] [CrossRef] [PubMed]
  14. de Lima, D.S.; Lima, J.C.; Calvacanti, R.M.C.B.; dos Santos, B.H.C.; Lima, I.O. Estudo da atividade antibacteriana dos monoterpenos timol e carvacrol contra cepas de Escherichia coli produtoras de β-lactamases de amplo espectro. Rev. Pan Amaz. Saúde 2017, 8, 17–21. [Google Scholar] [CrossRef] [Green Version]
  15. Apel, M.A.; Sobral, M.; Zuanazzi, J.Å.; Henriques, A.T. Essential oil composition of fourPlinia species (Myrtaceae). Flavour Fragr. J. 2006, 21, 565–567. [Google Scholar] [CrossRef]
  16. Borges, L.L.; Conceição, E.C.; Silveira, D. Active compounds and medicinal properties of Myrciaria genus. Food Chem. 2014, 153, 224–233. [Google Scholar] [CrossRef] [Green Version]
  17. Lago, J.H.G.; Souza, E.D.; Mariane, B.; Pascon, R.; Vallim, M.A.; Martins, R.C.C.; Baroli, A.A.; Carvalho, B.A.; Soares, M.G.; dos Santos, R.T.; et al. Chemical and Biological Evaluation of Essential Oils from Two Species of Myrtaceae—Eugenia uniflora L. and Plinia trunciflora (O. Berg) Kausel. Molecules 2011, 16, 9827–9837. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  18. Jayasena, V.; Cameron, I. °Brix/Acid ratio as a predictor of consumer acceptability of Crimson seedless table grapes. J. Food Qual. 2008, 31, 736–750. [Google Scholar] [CrossRef]
  19. Pontes, M.; Marques, J.C.; Câmara, J.S. Headspace solid-phase microextraction-gas chromatography-quadrupole mass spectrometric methodology for the establishment of the volatile composition of Passiflora fruit species. Microchem. J. 2009, 93, 1–11. [Google Scholar] [CrossRef] [Green Version]
  20. Jetti, R.R.; Yang, E.; Kurnianta, A.; Finn, C.; Qian, M.C. Quantification of Selected Aroma-Active Compounds in Strawberries by Headspace Solid-Phase Microextraction Gas Chromatography and Correlation with Sensory Descriptive Analysis. J. Food Sci. 2007, 72, S487–S496. [Google Scholar] [CrossRef]
  21. Bianchi, T.; Weesepoel, Y.; Koot, A.; Iglesias, I.; Eduardo, I.; Gratacós-Cubarsí, M.; Guerrero, L.; Hortós, M.; van Ruth, S. Investigation of the aroma of commercial peach (Prunus persica L. Batsch) types by Proton Transfer Reaction–Mass Spectrometry (PTR-MS) and sensory analysis. Food Res. Int. 2017, 99, 133–146. [Google Scholar] [CrossRef] [Green Version]
  22. Cao, X.; Xie, K.; Duan, W.; Zhu, Y.; Liu, M.; Chen, K.; Klee, H.; Zhang, B. Peach Carboxylesterase PpCXE1 Is Associated with Catabolism of Volatile Esters. J. Agric. Food Chem. 2019, 67, 5189–5196. [Google Scholar] [CrossRef]
  23. Lee, G.W.; Chung, M.S.; Lee, S.S.; Chung, B.Y.; Lee, S. Transcriptome-guided identification and functional characterization of key terpene synthases involved in constitutive and methyl jasmonate-inducible volatile terpene formation in Eremochloa ophiuroides (Munro)Hack. Plant Physiol. Biochem. 2019, 141, 193–201. [Google Scholar] [CrossRef] [PubMed]
  24. Lan-Phi, N.T.; Shimamura, T.; Ukeda, H.; Sawamura, M. Chemical and aroma profiles of yuzu (Citrus junos) peel oils of different cultivars. Food Chem. 2009, 115, 1042–1047. [Google Scholar] [CrossRef] [Green Version]
  25. Rao, B.R.R.; Sastry, K.P.; Saleem, S.M.; Rao, E.V.S.P.; Syamasundar, K.V.; Ramesh, S. Volatile flower oils of three genotypes of rose-scented geranium (Pelargonium sp.). Flavour Fragr. J. 2000, 15, 105–107. [Google Scholar] [CrossRef]
  26. Jürgens, A.; Webber, A.C.; Gottsberger, G. Floral scent compounds of Amazonian Annonaceae species pollinated by small beetles and thrips. Phytochemistry 2000, 55, 551–558. [Google Scholar] [CrossRef]
  27. Jürgens, A.; Witt, T.; Gottsberger, G. Flower scent composition in night-flowering Silene species (caryophyllaceae). Biochem. Syst. Ecol. 2002, 30, 383–397. [Google Scholar] [CrossRef]
  28. Borges, R.M.; Bessière, J.M.; Ranganathan, Y. Diel Variation in Fig Volatiles Across Syconium Development: Making Sense of Scents. J. Chem. Ecol. 2013, 39, 630–642. [Google Scholar] [CrossRef]
  29. Grison-Pigé, L.; Hossaert-McKey, M.; Greeff, J.M.; Bessière, J.M. Fig volatile compounds—A first comparative study. Phytochemistry 2002, 61, 61–71. [Google Scholar] [CrossRef]
  30. da Silva Barbosa, D.C.; Holanda, V.N.; de Assis, C.R.D.; de Oliveira Farias de Aguiar, J.C.R.; do Nascimento, P.H.; da Silva, W.V.; do Amaral Ferraz Navarro, D.M.; da Silva, M.V.; de Menezes Lima, V.L.; dos Santos Correia, M.T. Chemical composition and acetylcholinesterase inhibitory potential, in silico, of Myrciaria floribunda (H. West ex Willd.) O. Berg fruit peel essential oil. Ind. Crops Prod. 2020, 151, 112372. [Google Scholar] [CrossRef]
  31. Ramos, M.F.D.S.; Monteiro, S.D.S.; Da Silva, V.P.; Nakamura, M.J.; Siani, A.C. Essential oils from myrtaceae species of the Brazilian Southeastern Maritime forest (Restinga). J. Essent. Oil Res. 2010, 22, 109–113. [Google Scholar] [CrossRef]
  32. Tucker, A.O.; Maciarello, M.J.; Landrum, L.R. Volatile leaf oils of Caribbean Myrtaceae. II. Pimenta dioica (L.) Merr. of Jamaica. J. Essent. Oil Res. 1991, 3, 195–196. [Google Scholar] [CrossRef]
  33. Lawal, O.; Oyedeji, A. Chemical Composition of the Essential Oils of Cyperus rotundus L. from South Africa. Molecules 2009, 14, 2909–2917. [Google Scholar] [CrossRef] [PubMed]
  34. Vagionas, K.; Ngassapa, O.; Runyoro, D.; Graikou, K.; Gortzi, O.; Chinou, I. Chemical analysis of edible aromatic plants growing in Tanzania. Food Chem. 2007, 105, 1711–1717. [Google Scholar] [CrossRef]
  35. Costa, T.R.; Fernandes, O.F.L.; Santos, S.C.; Oliveira, C.M.A.; Lião, L.M.; Ferri, P.H.; Paula, J.R.; Ferreira, H.D.; Sales, B.H.N.; Silva, M.D.R.R. Antifungal activity of volatile constituents of Eugenia dysenterica leaf oil. J. Ethnopharmacol. 2000, 72, 111–117. [Google Scholar] [CrossRef]
  36. Oyedeji, A.O.; Ekundayo, O.; Olawore, O.N.; Adeniyi, B.A.; Koenig, W.A. Antimicrobial activity of the essential oils of five Eucalyptus species growing in Nigeria. Fitoterapia 1999, 70, 526–528. [Google Scholar] [CrossRef]
  37. Pavela, R.; Maggi, F.; Giordani, C.; Cappellacci, L.; Petrelli, R.; Canale, A. Insecticidal activity of two essential oils used in perfumery (ylang ylang and frankincense). Nat. Prod. Res. 2020, 1–7. [Google Scholar] [CrossRef]
  38. Fortes, G.A.C.; Naves, S.S.; Godoi, F.F.F.; Duarte, A.R.; Ferri, P.H.; Santos, S.C. Assessment of a maturity index in jabuticaba fruit by the evaluation of phenolic compounds, essential oil components, sugar content and total acidity. Am. J. Food Technol. 2011, 6, 974–984. [Google Scholar] [CrossRef]
  39. González-Mas, M.C.; Rambla, J.L.; Alamar, M.C.; Gutiérrez, A.; Granell, A. Comparative analysis of the volatile fraction of fruit juice from different citrus species. PLoS ONE 2011, 6, e22016. [Google Scholar] [CrossRef] [Green Version]
  40. Mirza, M.; Navaei, M.N.; Dini, M. Chemical composition of the oil ofCleome iberica DC. Flavour Fragr. J. 2005, 20, 434–435. [Google Scholar] [CrossRef]
  41. Alves, S.F.; Borges, L.L.; de Paula, J.A.M.; Vieira, R.F.; Ferri, P.H.; do Couto, R.O.; de Paula, J.R.; Bara, M.T.F. Chemical variability of the essential oils from fruits of Pterodon emarginatus in the Brazilian Cerrado. Braz. J. Pharmacogn. 2013, 23, 224–229. [Google Scholar] [CrossRef] [Green Version]
  42. Lin, K.H.; Yeh, S.Y.; Lin, M.Y.; Shih, M.C.; Yang, K.T.U.; Hwang, S.Y. Major chemotypes and antioxidative activity of the leaf essential oils of Cinnamomum osmophloeum Kaneh. From a clonal orchard. Food Chem. 2007, 105, 133–139. [Google Scholar] [CrossRef]
  43. Yao, Y.Q.; Ding, X.; Jia, Y.C.; Huang, C.X.; Wang, Y.Z.; Xu, Y.H. Anti-tumor effect of β-elemene in glioblastoma cells depends on p38 MAPK activation. Cancer Lett. 2008, 264, 127–134. [Google Scholar] [CrossRef] [PubMed]
  44. Wang, S.; Zhao, Z.; Yun-Ting, S.; Zeng, Z.; Zhan, X.; Li, C.; Xie, T. A review of medicinal plant species with elemene in China. Afr. J. Pharm. Pharmacol. 2012, 6, 3032–3040. [Google Scholar] [CrossRef] [Green Version]
  45. Sieniawska, E.; Sawicki, R.; Golus, J.; Swatko-Ossor, M.; Ginalska, G.; Skalicka-Wozniak, K. Nigella damascena L. essential oil-a valuable source of β-elemene for antimicrobial testing. Molecules 2018, 23, 256. [Google Scholar] [CrossRef] [Green Version]
  46. Sun, J. D-Limonene: Safety and Clinical Applications. Altern. Med. Rev. 2007, 12, 259–264. [Google Scholar]
  47. Vieira, A.J.; Beserra, F.P.; Souza, M.C.; Totti, B.M.; Rozza, A.L. Limonene: Aroma of innovation in health and disease. Chem. Biol. Interact. 2018, 283, 97–106. [Google Scholar] [CrossRef] [Green Version]
  48. Mizrahi, B.; Shapira, L.; Domb, A.J.; Houri-Haddad, Y. Citrus Oil and MgCl 2 as Antibacterial and Anti-Inflammatory Agents. J. Periodontol. 2006, 77, 963–968. [Google Scholar] [CrossRef]
  49. Moraes, T.M.; Kushima, H.; Moleiro, F.C.; Santos, R.C.; Machado Rocha, L.R.; Marques, M.O.; Vilegas, W.; Hiruma-Lima, C.A. Effects of limonene and essential oil from Citrus aurantium on gastric mucosa: Role of prostaglandins and gastric mucus secretion. Chem. Biol. Interact. 2009, 180, 499–505. [Google Scholar] [CrossRef]
  50. Manuele, M.G.; Arcos Barreiro, M.L.; Davicino, R.; Ferraro, G.; Cremaschi, G.; Anesini, C. Limonene exerts antiproliferative effects and increases nitric oxide levels on a lymphoma cell line by dual mechanism of the ERK pathway: Relationship with oxidative stress. Cancer Investig. 2010, 28, 135–145. [Google Scholar] [CrossRef]
  51. Yu, X.; Lin, H.; Wang, Y.; Lv, W.; Zhang, S.; Qian, Y.; Deng, X.; Feng, N.; Yu, H.; Qian, B. D-limonene exhibits antitumor activity by inducing autophagy and apoptosis in lung cancer. Onco. Targets. Ther. 2018, 11, 1833–1847. [Google Scholar] [CrossRef] [Green Version]
  52. Mehta, P.K.; de Sousa Galvão, M.; Soares, A.C.; Nogueira, J.P.; Narain, N. Volatile constituents of jambolan (Syzygium cumini L.) fruits at three maturation stages and optimization of HS-SPME GC-MS method using a central composite design. Food Anal. Methods 2018, 11, 733–749. [Google Scholar] [CrossRef]
  53. Freitas, T.P.; Spricigo, P.C.; Purgatto, E.; Jacomino, A.P. Aroma and soluble solid contents of the uvaia—A native Atlantic rainforest fruit—are negatively affected by early harvest. J. Food Biochem. 2019, e12881. [Google Scholar] [CrossRef] [PubMed]
  54. da Costa, J.S.; Barroso, A.S.; Mourão, R.H.V.; da Silva, J.K.R.; Maia, J.G.S.; Figueiredo, P.L.B. Seasonal and Antioxidant Evaluation of Essential Oil from Eugenia uniflora L., Curzerene-Rich, Thermally Produced in Situ. Biomolecules 2020, 10, 328. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  55. Van Schie, C.C.N.; Haring, M.A.; Schuurink, R.C. Tomato linalool synthase is induced in trichomes by jasmonic acid. Plant Mol. Biol. 2007, 64, 251–263. [Google Scholar] [CrossRef] [Green Version]
  56. Martin, D.M.; Gershenzon, J.; Bohlmann, J. Induction of volatile terpene biosynthesis and diurnal emission by methyl jasmonate in foliage of Norway spruce. Plant Physiol. 2003, 132, 1586–1599. [Google Scholar] [CrossRef] [Green Version]
  57. Taniguchi, S.; Hosokawa-Shinonaga, Y.; Tamaoki, D.; Yamada, S.; Akimitsu, K.; Gomi, K. Jasmonate induction of the monoterpene linalool confers resistance to rice bacterial blight and its biosynthesis is regulated by JAZ protein in rice. Plant Cell Environ. 2014, 37, 451–461. [Google Scholar] [CrossRef]
  58. Rodriguez-Saona, C.; Crafts-Brandner, S.J.; Paré, P.W.; Henneberry, T.J. Exogenous methyl jasmonate induces volatile emissions in cotton plants. J. Chem. Ecol. 2001, 27, 679–695. [Google Scholar] [CrossRef]
  59. Ament, K.; Kant, M.R.; Sabelis, M.W.; Haring, M.A.; Schuurink, R.C. Jasmonic acid is a key regulator of spider mite-induced volatile terpenoid and methyl salicylate emission in tomato. Plant Physiol. 2004, 135, 2025–2037. [Google Scholar] [CrossRef] [Green Version]
  60. Raguso, R.A. More lessons from linalool: Insights gained from a ubiquitous floral volatile. Curr. Opin. Plant Biol. 2016, 32, 31–36. [Google Scholar] [CrossRef] [Green Version]
  61. Bernreuther, A.; Schreierc, P. Multidimensional gas chromatography/mass spectrometry: A powerful tool for the direct chiral evaluation of aroma compounds in plant tissues. II. Linalool in essential oils and fruits. Phytochem. Anal. 1991, 2, 167–170. [Google Scholar] [CrossRef]
  62. Borg-Karlson, A.K.; Englund, F.O.; Unelius, C.R. Dimethyl oligosulphides, major volatiles released from Sauromatum guttatum and Phallus impudicus. Phytochemistry 1994, 35, 321–323. [Google Scholar] [CrossRef]
  63. Buttery, R.G.; Teranishi, R.; Ling, L.C.; Turnbaugh, J.G. Quantitative and Sensory Studies on Tomato Paste Volatiles. J. Agric. Food Chem. 1990, 38, 336–340. [Google Scholar] [CrossRef]
  64. Shimada, T.; Endo, T.; Fujii, H.; Rodríguez, A.; Peña, L.; Omura, M. Characterization of three linalool synthase genes from Citrus unshiu Marc. and analysis of linalool-mediated resistance against Xanthomonas citri subsp. citri and Penicilium italicum in citrus leaves and fruits. Plant Sci. 2014, 229, 154–166. [Google Scholar] [CrossRef] [PubMed]
  65. Yan, J.; Ban, Z.; Lu, H.; Li, D.; Poverenov, E.; Luo, Z.; Li, L. The aroma volatile repertoire in strawberry fruit: A review. J. Sci. Food Agric. 2018, 98, 4395–4402. [Google Scholar] [CrossRef] [PubMed]
  66. Bhatia, S.P.; McGinty, D.; Letizia, C.S.; Api, A.M. Fragrance material review on 4-carvomenthenol. Food Chem. Toxicol. 2008, 46, S91–S94. [Google Scholar] [CrossRef] [PubMed]
  67. Ribeiro, N.C.B.V.; Baseggio, A.M.; Schlegel, V. Jaboticaba: Chemistry and Bioactivity. Bioactive Mol. Food 2019, 1225–1251. [Google Scholar] [CrossRef]
  68. Defilippi, B.G.; Manríquez, D.; Luengwilai, K.; González-Agüero, M. Aroma Volatiles: Biosynthesis and Mechanisms of Modulation During Fruit Ripening. Adv. Bot. Res. 2009, 50, 228. [Google Scholar] [CrossRef]
  69. AOAC. Association of Official Analytical Chemists—International. Official Methods of Analysis, 19th ed.; AOAC: Gaithersburg, MD, USA, 2012. [Google Scholar]
  70. Carvalho, C.R.L.; Mantovani, D.M.B.; Carvalho, P.R.N.; de Moraes, R.M. Análises Químicas de Alimentos; Manual Téc.; ITAL: Campinas, Brazil, 1990. [Google Scholar]
  71. Pesis, E.; Ibáñez, A.M.; Phu, M.L.; Mitcham, E.J.; Ebeler, S.E.; Dandekar, A.M. Superficial scald and bitter pit development in cold-stored transgenic apples suppressed for ethylene biosynthesis. J. Agric. Food Chem. 2009, 57, 2786–2792. [Google Scholar] [CrossRef]
  72. Chong, J.; Wishart, D.S.; Xia, J. Using metaboanalyst 4.0 for comprehensive and integrative metabolomics data analysis. Curr. Protoc. Bioinform. 2019, 68. [Google Scholar] [CrossRef]
Sample Availability: Not available.
Molecules 25 04543 g001a 550Molecules 25 04543 g001b 550
Figure 1. Volatile compound profiles produced by ‘Sabará’ (Plinia jaboticaba), ‘Escarlate’ (Plinia phitrantha × Plinia cauliflora), ‘Otto Andersen’ (Plinia cauliflora), and ‘Esalq’ (Plinia phitrantha) jabuticabas: (A) Partial least squares-discriminant analysis (PLS-DA), (B) PLSDA loadings, and (C) heatmap. The numbers in Figure 1B,C correspond to the code of compounds listed in Table 1. The separation of clusters is shown in detail in Table S2.
Figure 1. Volatile compound profiles produced by ‘Sabará’ (Plinia jaboticaba), ‘Escarlate’ (Plinia phitrantha × Plinia cauliflora), ‘Otto Andersen’ (Plinia cauliflora), and ‘Esalq’ (Plinia phitrantha) jabuticabas: (A) Partial least squares-discriminant analysis (PLS-DA), (B) PLSDA loadings, and (C) heatmap. The numbers in Figure 1B,C correspond to the code of compounds listed in Table 1. The separation of clusters is shown in detail in Table S2.
Molecules 25 04543 g001aMolecules 25 04543 g001b
Molecules 25 04543 g002 550
Figure 2. Percentage of the relative area of the 36 volatile organic compounds in relation to all compounds identified in ‘Sabará’ (Plinia jaboticaba), ‘Escarlate’ (Plinia phitrantha × Plinia cauliflora), ‘Otto Andersen’ (Plinia cauliflora), and ‘Esalq’ (Plinia phitrantha) jabuticabas.
Figure 2. Percentage of the relative area of the 36 volatile organic compounds in relation to all compounds identified in ‘Sabará’ (Plinia jaboticaba), ‘Escarlate’ (Plinia phitrantha × Plinia cauliflora), ‘Otto Andersen’ (Plinia cauliflora), and ‘Esalq’ (Plinia phitrantha) jabuticabas.
Molecules 25 04543 g002
Table
Table 1. List of volatile aroma compounds found in ‘Sabará’ (Plinia jaboticaba), ‘Escarlate’ (Plinia phitrantha × Plinia cauliflora), ‘Otto Andersen’ (Plinia cauliflora), and ‘Esalq’ (Plinia phitrantha) jabuticabas by headspace solid-phase microextraction combined with gas chromatography/mass spectrometry (SPME-GC-MS).
Table 1. List of volatile aroma compounds found in ‘Sabará’ (Plinia jaboticaba), ‘Escarlate’ (Plinia phitrantha × Plinia cauliflora), ‘Otto Andersen’ (Plinia cauliflora), and ‘Esalq’ (Plinia phitrantha) jabuticabas by headspace solid-phase microextraction combined with gas chromatography/mass spectrometry (SPME-GC-MS).
CodeCompoundCAS *Odor Description **RI calc aRI lit bClass
1Ethyl acetate141-78-6pineapple909907ester
2Ethanol4-17-5alcohol929929alcohol
3Ethyl propionate105-37-3fruity, grape, pineapple977977ester
4Propyl acetate109-60-4solvent, celery989980ester
5d-α-pinene7785-70-8pine, turpentine10011011monoterpene
6Cyclofenchene488-97-1n.d.1010n.d.other
7α-thujene353313wood, green, herb10141021monoterpene
8Ethyl butyrate105-54-4fruity, juicy, pineapple10451047ester
9Ethyl isovalerate108-64-5fruity10541060ester
10Ethyl-2-methyl7452-79-1sharp, sweet, fruity10731073ester
11Hexanal66-25-1grass, tallow, fat10801084aldehyde
12Undecane1120-21-4alkane, wax11091100alkane
13β-pinene127-91-3pine, resin, turpentine11171116monoterpene
14β-thujene28634-89-1n.d.1125n.d.monoterpene
15Isoamyl acetate123-92-2fresh, banana, sweet11321132ester
16β-myrcene123-35-3balsamic, must, spice11441145monoterpene
17Ethyl (Z)-crotonate6776-19-8n.d.1156n.d.ester
18α-Phellandrene99-83-2turpentine, mint, spice11651166monoterpene
19d-limonene5989-27-5lemon, orange11741178monoterpene
20β-phellandrene555-10-2mint, terpentine12091209monoterpene
211,8 cineole470-82-6eucalyptus12201214monoterpenoid alcohol
222-hexenal505-57-7apple, green12211220aldehyde
23Ethyl hexanoate123-66-0apple peel, fruity12241223ester
24γ-terpinene99-85-4gasoline, turpentine12371238monoterpene
25(E)-ethyl tiglate5837-78-5sweet, berry, floral1239n.d.ester
26β-ocimene13877-91-3sweet, herb12401242monoterpene
27Propyl methacrylate2210-28-8n.d.1241n.d.ester
283-octanone106-68-3fresh, herbal, lavender12441241ketone
29o-cymene527-84-4n.d.12601260monoterpene
30Hexyl acetate142-92-7fruity, apple12641264ester
31cis-1,3,3-trimethylbicyclo[3.1.0]hexane-1-carboxaldehyde1000365-94-2n.d.1338n.d.aldehyde
32Ethyl 3-hexenoate2396-83-0sweet, fruity, pineapple1339n.d.ester
33(Z)-3-hexen-1-ol acetate3681-71-8green, banana13401327ester
344-hexen-1-ol acetate72237-36-6n.d.1343n.d.ester
35Methyl heptenone110-93-0citrus, green, lemongrass13441342ketone
36Ethyl 2-hexenoate1552-67-6fruity, green, sweet13471345ester
37Butyl 2-butenoate7299-91-4n.d.1352n.d.ester
38Hexanol111-27-3resin, flower, green13621360alcohol
39(Z)-3-hexen-1-ol928-96-1grass13921391alcohol
40Cyclopropanecarboxylic acid,3-methylbutyl ester1000245-65-3n.d.1396n.d.ester
41(E)-2-hexen-1-ol928-95-0leaf, green, fruity13981401alcohol
42Cyclopentane, 1-ethyl-1-methyl-16747-50-5n.d.1400n.d.alkane
43(E)-2-octenal2548-87-0green, nut, fat, leaf14071408aldehyde
44Ethyl octanoate106-32-1fruity, fat14321436ester
45α-cubebene17699-14-8herb, wax14621463sesquiterpene
462,2-dimethylhexanal996-12-3n.d.1478n.d.aldehyde
47δ-elemene20307-84-0wood14801468sesquiterpene
48α-copaene1000360-33-0wood, spice14851488sesquiterpene
49Ethyl sorbate110318-09-7fruity1487n.d.ester
502-ethyl-1-hexanol104-76-7rose, green14931487alcohol
51β-bourbonene5208-59-3herbal14951495sesquiterpene
52Benzaldehyde100-52-7almond, burnt sugar14981502aldehyde
53Grape butyrate5405-41-4marshmallow15221524ester
54Linalool78-70-6flower, lavender15331537sesquiterpenoid alcohol
55β-cubebene13744-15-5citrus, fruity15551546sesquiterpene
564-terpineol562-74-3pepper, woody, earth15961585monoterpenoid alcohol
57δ-selinene28624-23-9n.d.1601n.d.sesquiterpene
58l-bornyl acetate5655-61-8pine16031600sesquiterpenoid ester
59(E)-2-octen-1-ol18409-17-1mushroom (soap, plastic)16041590alcohol
60β-elemene515-13-9herb, wax, fresh16101595sesquiterpene
61(Z)-3-hexenyl (E)-2-butenoate65405-80-3green16111610ester
62Isoledene1000156-10-8n.d.1622n.d.sesquiterpene
63γ-elemene490377green, wood, oil16371636sesquiterpene
64Alloaromadendrene25246-27-9wood16391639sesquiterpene
651-epi-bicyclosesquiphellandrene54274-73-6n.d.1642n.d.sesquiterpene
66Aristolene6831-16-9n.d.1644n.dsesquiterpene
67α-muurolene31983-22-9wood1647n.d.sesquiterpene
68Methyl benzoate93-58-3prune, lettuce, herb, sweet16511640ester
69cis-muurola-4(14),5-diene1000365-95-4n.d.1661n.d.sesquiterpene
70Humulene6753-98-6wood16621663sesquiterpene
71Ethyl benzoate93-89-0camomile, flower, fruity16651658ester
72γ-muurolene30021-74-0herb, wood, spice16751681sesquiterpene
73γ-gurjunene22567-17-5musty1678n.dsesquiterpene
74Nonanol143-08-8fat, green16781666alcohol
75β-patchoulene514-51-2n.d.1681n.d.sesquiterpene
76Viridiflorene21747-46-6n.d.1699n.d.sesquiterpene
77β-selinene17066-67-0herb17151711sesquiterpene
78α-selinene473-13-2pepper, orange17191724sesquiterpene
79(E)-germacrene D23986-74-5wood, spice17311724sesquiterpene
80α-amorphene483-75-0n.d.17421752sesquiterpene
81Benzyl acetate140-11-4floral, fruity, jasmin17551747ester
82δ-cadinene483-76-1thyme, medicine, wood17591749sesquiterpene
832-phenylacetamide, N-(1-phenyl-2-propyl)-1000223-70-1n.d.1762n.d.other
84Cadine-1,4-diene16728-99-7spice, fruity17851786sesquiterpene
85Selina-3,7(11)-diene6813-21-4n.d.17891789sesquiterpene
86γ-cadinene39029-41-9wood17901776sesquiterpene
87Citronellyl butyrate141-16-2fruity, sweet, rose18021809monoterpenoid ester
88α-cadinene24406-05-1woody, dry18171815sesquiterpene
89Calamenene483-77-2herb, spice18241822sesquiterpene
90Geraniol106-24-1rose, geranium18451847monoterpenoid alcohol
91α-calacorene21391-99-1wood18901901sesquiterpene
92Palustrol95975-84-1n.d.1910n.d.sesquiterpenoid alcohol
93β-caryophyllene oxide1139-30-6herb, sweet, spice20202014sesquiterpene
94Ledol577-27-5sweet, green20402043sesquiterpenoid alcohol
95Methyl cinnamate103-26-4strawberry, cherry20652056ester
96Humulane-1,6-dien-3-ol1000140-23-1n.d.2081n.d.sesquiterpenoid alcohol
97Mansonone5574-34-5n.d.2095n.d.other
98Cubenol21284-22-0spice, herb, green tea20972097sesquiterpenoid alcohol
99p-vinylbenzohydrazide1000244-74-9n.d.2105n.d.other
100Rosifoliol63891-61-2n.d.2115n.d.sesquiterpenoid alcohol
101Ethyl cinnamate103-36-6sweet, fruity, spicy, berry plum21362139ester
102Selina-6-en-4-ol1000140-23-2n.d.2141n.d.sesquiterpenoid alcohol
103Carotol465-28-1pleasent mild2149n.d.sesquiterpenoid alcohol
104T-cadinol1474790wood, balsamic21502155sesquiterpenoid alcohol
105T-muurolol19912-62-0herb, weak spice, honey21572148sesquiterpenoid alcohol
106Spathulenol6750-60-3earthy, herbal, fruity21702153sesquiterpenoid alcohol
107Methyl isoeugenol93-16-3spicy, clove, blossom21802196other
1082,9-bornanediol54831-21-9n.d.2185n.d.monoterpenoid alcohol
109α-eudesmol473-16-5sweet, wood21902208sesquiterpenoid alcohol
110α-cadinol481-34-5herb, wood21922191sesquiterpenoid alcohol
111Cadalene483-78-3n.d.21962203sesquiterpene
1123,6-Dimethyl-4H-furo[3,2-c]pyran-4-one36745-38-7n.d.2201n.d.ketone
113Occidentalol29484-47-7n.d.2204n.d.sesquiterpenoid alcohol
114Juniper camphor473-04-1camphor2207n.d.sesquiterpenoid alcohol
115Tetracyclo[6.3.2.0(2,5).0(1,8)]tridecan-9-ol, 4,4-dimethyl1000157-75-1n.d.2211n.d.alcohol
116β-eudesmol473-15-4wood, green22252214sesquiterpenoid alcohol
117Galaxolide 21000285-26-7musk2230n.d.other
* Chemical abstracts service (CAS) is a division of the American Chemical Society. ** Descriptions consulted on the site https://www.pherobase.com/, http://www.thegoodscentscompany.com/, https://www.flavornet.org/, https://cosylab.iiitd.edu.in/flavordb/. a Retention index calculated. b Retention index from the literature database https://webbook.nist.gov/chemistry/, https://mona.fiehnlab.ucdavis.edu/, https://www.pherobase.com/.

Share and Cite

MDPI and ACS Style

Freitas, T.P.; Taver, I.B.; Spricigo, P.C.; do Amaral, L.B.; Purgatto, E.; Jacomino, A.P. Volatile Compounds and Physicochemical Quality of Four Jabuticabas (Plinia sp.). Molecules 2020, 25, 4543. https://doi.org/10.3390/molecules25194543

AMA Style

Freitas TP, Taver IB, Spricigo PC, do Amaral LB, Purgatto E, Jacomino AP. Volatile Compounds and Physicochemical Quality of Four Jabuticabas (Plinia sp.). Molecules. 2020; 25(19):4543. https://doi.org/10.3390/molecules25194543

Chicago/Turabian Style

Freitas, Thais Pádua, Isabela Barroso Taver, Poliana Cristina Spricigo, Lucas Bueno do Amaral, Eduardo Purgatto, and Angelo Pedro Jacomino. 2020. "Volatile Compounds and Physicochemical Quality of Four Jabuticabas (Plinia sp.)" Molecules 25, no. 19: 4543. https://doi.org/10.3390/molecules25194543

APA Style

Freitas, T. P., Taver, I. B., Spricigo, P. C., do Amaral, L. B., Purgatto, E., & Jacomino, A. P. (2020). Volatile Compounds and Physicochemical Quality of Four Jabuticabas (Plinia sp.). Molecules, 25(19), 4543. https://doi.org/10.3390/molecules25194543

Article Metrics

Back to TopTop