FLAVOUR AND FRAGRANCE JOURNALFlavour Fragr. J. 2003; 18: 271–274Published online in Wiley InterScience (www.interscience.wiley.com). DOI: 10.1002/ffj.1187

Copyright © 2003 John Wiley & Sons, Ltd.

John Wiley & Sons, Ltd.

Volatile constituents of fruits of Garcinia dulcis Kurz. from CubaFRUITS ESSENTIAL OIL OF GARCINIA DULCISJorge Pino,1* Rolando Marbot,2 Arístides Rosado2 and Carlos Vázquez3

1 Instituto de Investigaciones para la Industria Alimenticia, Carretera del Guatao km 31/2, La Habana 19200, Cuba2 Centro Nacional de Investigaciones Científicas, La Habana, Cuba3 Jardín Botánico Nacional, La Habana, Cuba

Received 11 December 2001Revised 18 February 2002Accepted 29 July 2002

ABSTRACT: The volatile constituents of rata fruits (Garcinia dulcis Kurz.) growing in Cuba were analysed byGC–MS. Ninety compounds were identified in the aroma concentrate, of which linalool, α-terpineol and hexa-decanoic acid were found to be the major constituents. Copyright © 2003 John Wiley & Sons, Ltd.

KEY WORDS: Garcinia dulcis Kurz.; Guttiferae; rata; fruit volatiles; linalool; α-terpineol; hexadecanoic acid

Introduction

The rata or garcinia (Garcinia dulcis Kurz.) very muchresembles the mangosteen in size of the tree and in gen-eral growth. It belongs to the botanical family Guttiferaeand is probably native to the Phillipines or Borneo. Thetree produces a thin-skinned, yellow fruit about 1 in indiameter, with a short sharp point at the flower end. Thesoft flesh of the ripe fruit has a butter-like consistencyand a pleasant acid flavour. It is a dessert fruit andmay be eaten fresh, in jams and as flavouring in otherfoods.1

These aromatic properties led us to investigate itscomposition in order to determine the respective influenceof the volatile constituents. To date the aroma of G. dulcisfruit has not been the subject of a previous study.

Experimental

Materials and Isolation of the Volatile Constituents

Samples of ripe fruits were collected from a NationalBotanic Garden in Havana, in May 2001, from a singlespecimen, at the same time. A voucher specimen of theplant was deposited in the herbarium of the NationalBotanic Garden. After addition of an internal standard(methyl undecanoate, 2 mg), pulp (200 g) was blendedwith distilled water (600 ml), adjusted to pH 7, and

simultaneously distilled and extracted for 60 min in aLikens–Nickerson microapparatus with 25 ml diethylether (previously redistilled and checked as to purity).The volatile concentrate was dried over anhydrous sul-phate and concentrated to 0.6 ml on a Kuderna-Danishevaporator with a 12 cm Vigreux column, and then to0.2 ml with a gentle nitrogen stream.

Analysis of the Volatile Constituents

The extract was analysed by GC using a Hewlett-Packard6890 gas chromatograph equipped with a flame ioniza-tion detector (FID). The separations were performed usinga SPB-5 column (30 m × 0.25 mm i.d., 0.25 µm filmthickness). Oven temperature program, 60 °C for 2 min,rising at 4 °C/min to 250 °C, then held for 20 min. Thecarrier gas was helium with a flow-rate of 1 ml/min. Thetemperature of the injector and detector was 250 °C.The injection was made in the split mode (1:10 ratio).Linear retention indices (Kováts indices) were calculatedagainst those of n-paraffins.2 These conditions were usedfor quantitative analysis, by the internal standardmethod. The recovery of the method was determinedby the standard addition technique applied to a sample.The analytes (α-pinene, limonene, ethyl butanoate, ethylhexanoate, ethyl octanoate, linalool and α-terpineol)were added at two different concentrations. The averagerecoveries were about 80–102% and their relative standarddeviations were lower than 10%. Analyses was made byduplicate.

GC–MS analyses were performed with a Hewlett-Packard Series 6890 gas chromatograph equipped with aHP-5973 mass-selective detector. The chromatographic

* Correspondence to: J. Pino, Instituto de Investigaciones para la IndustriaAlimenticia, Carretera del Guatao km 31/2, La Habana 19200, Cuba.

Copyright © 2003 John Wiley & Sons, Ltd. Flavour Fragr. J. 2003; 18: 271–274

272 J. PINO ET AL.

Table 1. Volatile constituents of Garcinia dulcis fruit

Constituents RI Means of identificationa Concentration (mg/kg)

Acetaldehyde 435 A 0.03Ethanol 500 A 0.781-Propanol 568 A 0.07Diacetyl 612 A 0.022-Methyl-3-buten-2-ol 620 C 1.251-Butanol 668 A 0.022-Pentanone 689 A <0.01Acetoin 720 A <0.013-Methyl-1-butanol 736 A 0.06Pyridine 752 A <0.013-Methyl-2-buten-1-ol 779 B 0.24Butanoic acid 780 A <0.01Ethyl butanoate 800 A 0.042-Furfural 830 A 0.25Furfuryl alcohol 851 C 0.01Isopentyl acetate 876 A <0.01p-Xylene 884 A 0.012-Heptanone 895 A 0.01o-Xylene 896 A <0.01Santolina triene 908 B <0.012-Acetylfuran 910 C <0.01γ-Butyrolactone 916 C 0.02Methyl hexanoate 923 A 0.01α-Pinene 939 A <0.01Benzaldehyde 961 A 0.015-Methylfurfural 963 C <0.012-Vinyltetrahydro-2,6,6-trimethyl-2H-pyran 971 C 0.77β-Pinene 979 A <0.01Methyl 2-furoate 980 B <0.01Myrcene 991 A <0.01Hexanoic acid 993 A 0.481,4-Cineole 1016 A <0.01α-Terpinene 1018 A 0.04p-Cymene 1026 A 0.04Limonene 1031 A 0.381,8-Cineole 1033 A <0.01(Z)-β-Ocimene 1040 A 0.14Cyclohexyl acetate 1043 C 0.11(E)-β-Ocimene 1051 A 0.32γ-Terpinene 1062 A 0.06Acetophenone 1065 A <0.01(Z)-Linalool oxide 1074 A 0.82p-Methylbenzaldehyde 1079 A <0.01Terpinolene 1087 A 0.90(E)-Linalool oxide 1088 A 0.06Methyl benzoate 1091 A 0.01Linalool 1098 A 5.52Hotrienol 1101 A 0.16Myrcenol 1118 B 0.12Methyl octanoate 1124 A <0.01cis-β-Terpineol 1145 B 0.04trans-β-Terpineol 1163 B 0.23Terpinen-4-ol 1177 A 0.08Octanoic acid 1180 A 0.12α-Terpineol 1189 A 3.97γ-Terpineol 1192 C 0.07Ethyl octanoate 1195 A 0.03α-Ionene 1205 C 0.031-p-Menthen-9-al 1217 C 0.08Benzothiazole 1221 B <0.01Nerol 1228 A 0.17Cuminaldehyde 1240 A <0.01Geraniol 1255 A 0.55Vitispirane 1272 C 0.09cis-Verbenyl acetate 1282 B <0.01(E)-Anethole 1283 A 0.02trans-Verbenyl acetate 1293 B <0.01Edulan I 1309 C 0.03Methyl decanoate 1324 A <0.01Dehydroionene 1342 C <0.01

FRUITS ESSENTIAL OIL OF GARCINIA DULCIS 273

Copyright © 2003 John Wiley & Sons, Ltd. Flavour Fragr. J. 2003; 18: 271–274

Eugenol 1356 A <0.01γ-Nonalactone 1360 A <0.01Decanoic acid 1380 A <0.01(E)-β-Damascenone 1381 B <0.01Ethyl decanoate 1394 A <0.01(E)-β-Caryophyllene 1418 A <0.01Dodecanoic acid 1578 A 0.07Ethyl dodecanoate 1595 A 0.01Methyl tetradecanoate 1725 A <0.01Tetradecanoic acid 1771 A 0.19Ethyl tetradecanoate 1793 A <0.01Pentadecanoic acid 1872 A 0.01Methyl hexadecanoate 1926 A 0.01Hexadecanoic acid 1973 A 2.02Ethyl hexadecanoate 1993 A 0.16Methyl octadecanoate 2128 A 0.01Oleic acid 2137 A 0.02Octadecanoic acid 2172 A 0.14Ethyl octadecanoate 2194 A 0.01

a The reliability of the identification proposal is indicated by the following: A, mass spectrum and Kováts index agreed with standards;B, mass spectrum and Kováts index agreed with literature data; C, mass spectrum agreed with mass spectral database.

Constituents RI Means of identificationa Concentration (mg/kg)

conditions were the same as those described for GC–FID.The detector operated in impact electron mode (70 eV)at 230 °C. Detection was performed in the scan modebetween 30 and 400 Da. Compounds were identified bycomparing their spectra to those of the Wiley library orour IDENT library and also by comparison of their GCKováts indices with those of standard compounds anddata from literature.3,4

Taste Panel Procedures

Samples (10 g) of fresh pulp were laced into three-digitrandomly coded glass screw cap vials (8 × 4 cm) andequilibrated to room temperature until presentation tothe panelists. Sensory analysis testing was conducted inthe sensory analysis testing laboratory. Six panelists wererecruited for each panel session from the laboratorystaff. Training procedures for panel members generallyfollowed those described elsewhere.5 Prior to sampletesting, the panelists were familiarized with attributedescriptions and a series of descriptors were selectedfrom panelist free-choice.

Results and Discussion

The volatile constituents of rata fruit were obtained bysimultaneous steam distillation–solvent extraction andanalysed by GC and GC–MS using fused silica capil-lary columns. Table 1 summarizes the qualitative andquantitative analyses of the fruit volatiles accordingto order of elution on the SPB-5 column. The yield oftotal volatiles, estimated by the addition of a measured

amount of internal standard to the pulp, was approxim-ately 21 mg/kg of fruit pulp.

Ninety constituents were identified, all of themreported for the first time as volatile components of rata.Quantitative data, expressed as mg/kg in fruit, should beconsidered as estimations only, because the assumptionsmade when considering these concentrations (85% meanrecovery and equal response factor for each analytes). Arough survey of the chemical classes represented in thisfruit flavour was as follows: terpenoids comprise thelargest class of volatiles (65.5%); the composition of theother classes of compounds was as follows: fatty acids,11.7%; alcohols, 7.8%; esters, 2.0%; furanoids, 1.2%; andothers, 11.4%. The major constituents found in rata flavourwere linalool (5.52 mg/kg), α-terpineol (3.97 mg/kg)and hexadecanoic acid (2.02 mg/kg).

Some compounds present, e.g. furfural, and somefuranes could be probably degradation products ofascorbic acid and sugars. It has been reported that acidtreatment and even distillation induce the oxidation ofascorbic acid.5 Nevertheless, the concentrate obtainedfrom the extraction had a strong aroma characteristic ofthe fruit.

Odour descriptors provided by a sensory panelincluded floral-woody, acidic and pungent. The presenceof linalool, α-terpineol and linalool oxides could beresponsible for the floral-woody notes, while the higheramounts of fatty acids could be responsible for theacidic and pungent notes observed in rata fruit.

Taken together, these results indicate that the exoticaroma character of rata is the interaction of floral–woody(linalool, α-terpineol and linalool oxides), with acidicand pungent (fatty acids) notes contributing to the com-plexity of the flavour.

Table 1. (Continued)

Copyright © 2003 John Wiley & Sons, Ltd. Flavour Fragr. J. 2003; 18: 271–274

274 J. PINO ET AL.

References

1. Martin FW, Cambell CW, Ruberté RM. Tropical Edible Fruits ofthe Tropics: An Inventory. USDA, Agricultural Research Service,Washington, DC, 1987.

2. Majlat P, Erdos Z, Takacs J. Calculation and application of reten-tion indices in programmed temperature gas chromatography. J.Chromatogr., 1974; 91: 89–110.

3. MacLafferty FW, Staffer DB. The Wiley/NBS Registry of MassSpectral Data. Wiley: New York, 1989.

4. Adams RP. Identification of Essential Oil Components by GasChromatography/Mass Spectroscopy. Allured: Carol Stream, IL,1995.

5. Tatum JH, Shaw PE, Berry RE. Degradation products from ascorbicacid. J. Agric. Food Chem., 1969; 17: 38–40.