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Comparative Study of the Leaf Volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae)

Faculty of Science and Mathematics, University of Niš, 18000 Niš, Serbia
Author to whom correspondence should be addressed.
Molecules 2010, 15(9), 6168-6185;
Submission received: 28 June 2010 / Revised: 25 August 2010 / Accepted: 30 August 2010 / Published: 2 September 2010


The first GC and GC/MS analyses of the essential oils hydrodistilled from dry leaves of Arctostaphylos uva-ursi and Vaccinium vitis-idaea enabled the identification of 338 components in total (90.4 and 91.7% of the total GC peak areas, respectively). Terpenoids, fatty acids, fatty acid- and carotenoid derived compounds were predominant in the two samples. Both oils were characterized by high relative percentages of α-terpineol and linalool (4.7-17.0%). Compositional data on the volatiles of the presently analyzed and some other Ericaceae taxa (literature data) were mutually compared by means of multivariate statistical analyses (agglomerative hierarchical cluster analysis and principal component analysis). This was done in order to determine, based on the essential oil profiles, possible mutual relationships of the taxa within the family, especially that of species from the genera Arctostaphylos and Vaccinium. Results of the chemical and statistical analyses pointed to a strong relation between the genera Vaccinium and Arctostaphylos.

1. Introduction

It has been known for centuries that leaves of Arctostaphylos uva-ursi (L.) Spreng., Ericaceae (Bear's grape, bearberry) possess powerful astringent activity, mainly due to the presence of glycosides such as arbutin [1]. In 1601, Clusius reported its earlier use by Galen (ca. 130–200 C.E.) as a hemostatic. In modern Western medical practice, its use seems to begin with Spanish and Italian physicians (ca. 1730–1740 C.E.) for calculus complaints [2]. For more than 100 years now this plant species has been official in nearly all Pharmacopeias and is widely used for treating bladder and kidney disorders, inflammatory diseases of the urinary tract, urethritis, cystitis, for strengthening and imparting tone to the urinary passages, etc. [1,2]. During collection, bearberry is commonly confused with cowberry (Vaccinium vitis-idaea L.) and box (Buxus sempervirens L.). Poisonous B. sempervirens (similar morphological characteristics, but without the pharmacologically active arbutin) has occasionally been used to adulterate the drug [1,3]. Vaccinium vitis-idaea and other representatives of the genus Vaccinium (Ericaceae), on the other hand, could be regarded as suitable substitutions for A. uva-ursi (comparable content of arbutin and similar pharmacological action of leaves’ infusions) [1]. Some recent studies have shown that biologically active phenologlycosides, simple phenols, flavonoids, tannins, polysaccharides, etc. are also present in V. vitis-idaea and A. uva-ursi [4,5,6,7,8].
It has been previously shown that essential oils may, despite their small yield, contribute to the medicinal properties of the plant [9]. Moreover, volatile metabolites could be potentially used as a tool which could give a quick insight to the presence/absence (i.e. expression) of a certain biosynthetic “apparatus” in some plant taxa, and to some extent, to the (dis)similarity of the compared species on a molecular level [10]. To the best of our knowledge, there are no previous reports on the essential oil profile of A. uva-ursi and there is a limited data concerning the volatiles of V. vitis-idaea and only of the berries [11,12]. Thus, the aim of this work was set to analyze in detail (using GC and GC/MS) and compare the chemical composition of the essential oils hydrodistilled from the dry leaves of A. uva-ursi and V. vitis-idaea, in order to determine if any further phytochemical similarities between the two species exist. Comparison of the compositional data of the oils from a number of Ericaceae taxa (present study and the literature data [13,14,15,16,17,18,19,20,21,22,23]) was achieved using multivariate statistical analyses (MVA: agglomerative hierarchical cluster analysis (AHC) and principal component analysis (PCA)).

2. Results and Discussion

GC and GC/MS analyses of the essential oils extracted from Arctostaphylos uva-ursi and Vaccinium vitis-idaea leaves enabled the identification of 338 different constituents (243 in A. uva-ursi and 187 in V. vitis-idaea, Table 1), representing 90.4 and 91.7% of the total GC peak areas, respectively. The major contributors to the V. vitis-idaea oil were α-terpineol (17.0%), pentacosane (6.4%), (E,E)-α-farnesene (4.9%), linalool (4.7%) and (Z)-hex-3-en-1-ol (4.4%). The same two constituents, α-terpineol (7.8%) and linalool (7.3%), were predominant in the oil of A. uva-ursi, additionally characterized by hexadecanoic acid (4.5%) and (E)-geranyl acetone (4.1%). Another common feature of the analyzed oils was the presence of terpenoids (46.8 and 49.5% in A. uva-ursi and V. vitis-idaea oils, respectively) and fatty acid derived compounds (34.1% - V. vitis-idaea, 10.7% - A. uva-ursi oil) in high relative amounts. Fatty acids and fatty acid esters (F, 11.8%), and carotenoid derived compounds (CD, 14.1%) represented a significant portion of A. uva-ursi oil. The mentioned constituents belonging to F and CD classes were identified in the V. vitis-idaea oil as well, but were present in a considerably smaller relative amount.
Table 1. Chemical composition of the essential oils extracted from the leaves of Arctostaphylos uva-ursi and Vaccinium vitis-idaea.
Table 1. Chemical composition of the essential oils extracted from the leaves of Arctostaphylos uva-ursi and Vaccinium vitis-idaea.
RI1ClassIdentification2CompoundV. vitis-idaea, %A. uva-ursi, %
725GLa, b(Z)-3-Penten-1-ol tr
732GLa, b(E)-3-Penten-2-one tr3tr
739MRPa, b, cPyridine tr
744GLa, b(E)-2-Pentenaltrtr
762GLa, b, c1-Pentanoltrtr
765GLa, b(Z)-2-Penten-1-ol0.80.2
772THa, b3-Methyl-2-buten-1-ol (syn.4 prenol) 0.1
772Oa, b, cN,N-Dimethyl formamide 0.4
781THa, b3-Methyl-2-butenal (syn. prenal) tr
783GLa, b, c2,4-Pentandione (syn. acetyl acetone)tr
801GLa, b, cHexanaltr0.1
824MRPa, bMethylpyrazine tr
827Oa, b, cMaleic anhydride tr
832THa, b, c2-Methylbutanoic acidtr
828GL/MRPa, b, cFurfural0.20.8
839GLa, b, c4-Hydroxy-4-methyl-2-pentanonetrtr
844GLa, b(E)-3-Hexen-1-oltr
854GLa, b(E)-2-Hexenaltr0.7
854GLa, b(E)-2-Hexen-1-ol1.2
858GLa, b(Z)-3-Hexen-1-ol4.4tr
867GLa, b, c1-Hexanoltrtr
863MRPa, b, c3-Methylpyridine 0.2
869MPRa, bα-Angelica lactone tr
892AEa, b1-Nonene tr
896Oa, b2-Methyl-2-cyclopentenone tr
900THa, b, cIsopropyl 3-methylbutanoate 0.1
913GLa, b(E,E)-2,4-Hexadienaltrtr
915MRPa, b, c2-Acetylfurantr0.2
916MRPa, bEthylpyrazine tr
920MRPa, b2,3-Dimethylpyrazine tr
935GLa, b2-Methylpentanoic acidtr
956GLa, b(E)-2-Heptenaltr0.1
959MRPa, b3-Ethylpyridine 0.1
959GLa, b(Z)-3-Hepten-1-oltr
965MRPa, b, cBenzaldehyde0.60.2
963MRPa, b5-Methyl-2-furancarboxaldehyde tr
967GLa, b, c1-Heptanoltrtr
968MRPa, b3-Ethenylpyridine 0.4
971GLa, b, cHexanoic acid0.6
973GLa, b(E)-4-Octen-3-one tr
978GLa, b1-Octen-3-oltr0.1
978MRPa, b, cPhenol tr
986CRa, b6-Methyl-5-hepten-2-one 0.1
989Oa, b, cBenzonitrile tr
993GLa, b2-Pentylfuran tr
995GLa, b3-Octanol tr
999GLa, b(E,Z)-2,4-Heptadienaltr0.3
1001MRPa, b2-Ethyl-6-methylpyrazine tr
1004MRPa, b2-Ethyl-5-methylpyrazine tr
1005MRPa, bTrimethylpyrazine tr
1013GLa, b(E,E)-2,4-Heptadienaltr0.7
1019MRPa, b5-Ethyl-2-methylpyridine tr
1022TMMa, b, cLimonenetr
1027Oa, b2-Ethylhexan-1-oltr0.1
1027TMAa, b, cp-Cymene tr
1031GLa, b(E)-3-Octen-2-onetrtr
1036MRPa, b, cBenzyl alcohol0.70.2
1047MRPa, b, cPhenylacetaldehyde0.51.0
1047Oa, b, cSalicylaldehyde tr
1053Oa, b, c2-Methylphenol 0.1
1057Aa, b4-Methyldecanetr
1058GLa, b(Z)-2-Octenal 0.1
1062GLa, b, cPentyl isobutanoatetr
1067GLa, b(E)-2-Octen-3-oltr0.1
1069GLa, b, c1-Octanol0.90.7
1071GLa, b(E,E)-3,5-Octadien-2-one tr
1071Oa, b, cAcetophenonetr
1072Oa, b, c4-Methylbenzaldehyde tr
1074Oa, b, c4-Methylphenol tr
1075TMAa, b, ccis-Linalooloxide (furanoid)0.51.3
1086Oa, b3-Methylbenzaldehyde tr
1090TMMa, bα-Cumyl alcohol (syn. 2-phenyl-2-propanol)tr
1092TMAa, b, ctrans-Linalooloxide (furanoid)0.30.9
1093TMMa, bp-Cymenene tr
1097GLa, b1-Nonen-4-ol tr
1098GLa, bIsobutyl tiglate0.4
1102TMAa, b, cLinalool4.77.3
1106GLa, b, cNonanal0.5tr
1107TMa, bHotrienoltr
1107CRa, b6-Methyl-3,5-heptadien-2-one 1.8
1111TMTa, b, cα-Thujone 0.7
1114Oa, b2,6-Dimethylcyclohexanoltr0.2
1117MRPa, b, c2-Phenyl-1-ethanol 0.6
1120TMAa, bMyrcenol tr
1121TMTa, b, cβ-Thujone 0.1
1125TMTa, bDehydrosabinaketone 0.1
1126CRa, b, cIsophoronetr
1130TMPa, bα-Campholenal tr
1140GLa, b(E)-3-Nonen-2-one tr
1143Oa, bPhenylacetonitriletr
1145TMPa, b, ctrans-Pinocarveol tr
1145TMMa, bLilac aldehyde Btr0.2
1147CRa, b4-Oxoisophoronetrtr
1150TMBa, b, cCamphor 0.8
1154TMAa, bLilac aldehyde A0.4tr
1154GLa, b(E,Z)-2,6-Nonadienal 0.4
1157TMAa, bNeroloxide tr
1158TMMa, b, cMenthone 0.2
1161GLa, b(E)-2-Nonenaltr0.3
1165TMAa, b(Z)-β-Ocimenol 0.1
1167Oa, b, cBenzyl acetatetr
1169TMMa, b, cMenthol 0.3
1169TMAa, bLilac aldehyde Ctr
1170Fa, b, cOctanoic acid0.7
1171TMMa, bα-Phellandren-8-ol tr
1172TMMa, bp-Mentha-1,5-dien-8-oltr
1172TMBa, b, cBorneol 1.4
1173TMAa, bcis-Linalooloxide (pyranoid) tr
1175Oa, b, cEthyl benzoatetr
1177TMMa, bIsomenthol 1.9
1179TMAa, btrans-Linalool oxide (pyranoid)tr
1181Oa, b2,4-Dimethylbenzaldehydetr
1182TMMa, bTerpinen-4-ol0.51.0
1186TMPa, bIsoverbanoltr
1188TMMa, bneo-Isomenthol tr
1189TMMa, bp-Cymen-8-ol0.20.6
1190Oa, b, cNaphthalene tr
1196TMMa, bα-Terpineol17.07.8
1200Oa, b, cMethyl salicylate0.50.1
1202TMPa, b, cMyrtenol 0.1
1203TMMa, bγ-Terpineoltr
1205CRa, bSafranaltr0.2
1207GLa, b, cDecanaltr0.1
1213TMMa, btrans-Piperitol tr
1216TMPa, b, cVerbenone 0.3
1216GLa, b(E,E)-2,4-Nonadienaltrtr
1221TMMa, b1-p-Menthen-9-al isomer 10.40.6
1223TMMa, b, ctrans-Carveol tr
1223TMMa, b1-p-Menthen-9-al isomer 20.50.4
1226CRa, bβ-Cyclocitral0.40.2
1231TMAa, b(Z)-Ocimenonetr
1231TMAa, b, cNerol0.20.8
1237TMMa, b, cThymol methyl ether
1244TMMa, b, cPulegone 0.3
1247TMMa, b, cCarvacrol methyl ethertr
1249TMMa, b, cCarvone 0.2
1252TMMa, bPerilla ketone 0.1
1256TMAa, b, cGeraniol1.53.0
1259TMMa, bPiperitone 0.2
1263GLa, b(E)-2-Decenal0.50.7
1273TMAa, b, cGeranial 1.3
1275Fa, b, cNonanoic acid0.40.7
1277TMMa, bPerilla aldehyde1.2
1286GLa, bVitispirane 0.9
1290PPa, b, ctrans-Anethole 0.6
1290TMBa, b, cIsobornyl acetate tr
1294TMMa, b, cThymol 2.0
1294AEa, b1-Tridecenetr
1296GLa, b(E,Z)-2,4-Decadienaltrtr
1297TMMa, b, cMenthyl acetate tr
1299Oa, b2-Methylnaphthalene tr
1300Oa, b, cIndoletr
1300Aa, b, cTridecanetr
1304TMMa, b, cCarvacrol 0.9
1304TMMa, bPerilla alcoholtr
1309GLa, bUndecanal 0.1
1313CRa, bRiesling acetal 1.4
1317Oa, b1-Methylnaphthalene tr
1318PPa, b4-Vinylguaiacoltrtr
1319GLa, b(E,E)-2,4-Decadienal0.81.7
1323Oa, b2,4,6-Trimethylbenzaldehyde 0.1
1326GLa, b(Z)-3-Hexenyl tiglatetr
1336Aa, bBranched alkanetr
1341CRa, b(E,E)-2,5-Epoxy-6,8-megastigmadienetr
1344Aa, bBranched alkanetr
1353TMMa, bα-Terpineol acetate 0.7
1359Oa, b1,1,6-Trimethyl-1,2-dihydronaphthalene0.20.6
1361PPa, b, cEugenol0.7tr
1363TMAa, bHydroxy citronellol(syn. 3,7-dimethyl-1,7-octanediol)tr
1366GLa, b(E)-2-Undecenaltr0.2
1367Fa, bγ-Nonalactonetr
1371CRa, b(E,Z)-4,6,8-Megastigmatrienetr
1370Fa, b, cDecanoic acidtr0.8
1377Aa, b3-Methyltridecanetr
1383CRa, bα-Ionol 0.3
1383GLa, b(Z)-3-Hexenyl hexanoate0.8
1384Oa, b, cBiphenyl tr
1388GLa, b(Z)-3-Hexenyl (Z)-3-hexenoate0.3
1390CRa, b(E)-β-Damascenone 0.3
1391GLa, b(E)-2-Hexenyl caproatetr
1396AEa, b1-Dodecenetr
1398CRa, b(Z)-Jasmonetr
1400Aa, b, cTetradecanetrtr
1404CRa, b(2E)-3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenaltr0.4
1407CRa, bHexahydropseudoionone (syn. tetrahydrogeranyl acetone)tr0.1
1409Oa, b2,6-Dimethylnaphthalene tr
1411ALa, bDodecanaltrtr
1416Oa, b1-Ethenylnaphthalene tr
1420CRa, b(E)-β-Damasconetr
1423TSa, bβ-Cedrene 0.2
1424Oa, b1,3-Dimethylnaphthalene tr
1427TSCRa, b, cβ-Caryophyllene2.90.9
1433CRa, b, c(E)-α-Ionone 0.1
1440TSa, bCalarene (syn. β-Gurjunene) tr
1444Oa, b2,3-Dimethylnaphthalene tr
1454Oa, bAcenaphthylene tr
1456CRa, b(E)-Geranyl acetonetr4.1
1457Aa, b4-Methylpentadecanetr
1460TSFa, b(E)-β-Farnesene tr
1462TSHa, b, cα-Humulene1.11.2
1463Aa, b2-Methyltetradecanetrtr
1465Fa, bUndecanoic acid 0.2
1476ALCa, b1-Dodecanol tr
1483TSCDa, bγ-Muurolene 0.6
1488TSGERa, bGermacrene D tr
1492CRa, b, c(E)-β-Ionone1.11.3
1494TSEDa, bβ-Selinene tr
1497TSa, bα-Zingiberene0.6
1498FADa, b2-Tridecanone 0.1
1500TSEDa, bδ-Selinenetr
1500Aa, b, cPentadecanetrtr
1503TSEDa, bα-Selinene 0.8
1503Oa, bBenzyl tiglatetr
1507TSCDa, bα-Muurolene 0.2
1509TSAGa, b4-epi-cis-Dihydroagarofurantr
1511TSFa, b(E,E)-α-Farnesene4.9
1513ALa, bTridecanal tr
1513TSa, bβ-Bisabolene 0.3
1514TSCDa, bγ-Cadinene tr
1521TSCDa, bδ-Cadinene 0.9
1526TSEDa, b7-epi-α-Selinenetr
1527PPa, b, cMyristicin 0.6
1530TSCDa, btrans-Cadina-1,4-diene tr
1532Oa, bLilialtr
1535CRa, b(E,Z)-Pseudoionone 0.3
1538CRa, bDihydroactinidiolide 0.1
1542Aa, bBranched alkanetr
1544TSCDa, bα-Cadinene tr
1550TSCDa, bα-Calacorene 0.2
1555TSAGa, bα-Agarofuran1.8
1561Aa, b2-Methylpentadecanetr
1565Fa, b, cDodecanoic acid0.61.8
1571Oa, b2,3,5-Trimethylnaphthalene 0.2
1571Aa, b3-Methylpentadecane tr
1576GLa, b(Z)-3-Hexenyl benzoatetr0.3
1582TSFa, b(Z)-Dihydroapofarnesol0.8
1586TSa, b, cSpathulenol tr
1587Oa, b9H-Fluorene 0.6
1589CRa, b(E,E)-Pseudoionone 0.4
1592TSCRa, b, cCaryophyllene oxide0.8
1593AEa, b1-Hexadecenetr
1594Oa, b3,3'-Dimethylbiphenyl tr
1600Aa, b, cHexadecane 0.7
1601TSa, bViridiflorol 0.1
1602TSa, b4(14)-Salvialen-1-one tr
1607TSHa, bHumulene epoxide I 0.1
1611TSa, bCedrol 0.2
1614ALa, bTetradecanaltr
1615ALa, b(E)-7-Tetradecenal tr
1619TSHa, bHumulene epoxide II tr
1629Fa, b, cIsopropyl laurate tr
1629TSEDa, b10-epi-γ-Eudesmol3.0
1634Oa, b, cBenzophenone tr
1638Oa, b4-Methyldibenzofuran tr
1640TSEDa, bγ-Eudesmoltr0.6
1646TSCRa, bCaryophylla-3(15),7(14)-dien-6-ol tr
1649TSCDa, bτ-Cadinol 0.3
1650TSCDa, bCubenol tr
1654TSCDa, bα-Muurolol 0.2
1659TSEDa, bα-Eudesmoltr
1662TSERa, bValerianol1.7
1665Aa, b2-Methylhexadecane tr
1666TSCDa, bα-Cadinol 0.2
1667TSEDa, b7-epi-α-Eudesmoltr
1675ALCa, b1-Tetradecanol0.9
1676TSFa, bHexahydrofarnesol 0.1
1683Oa, bHexyl salicylatetr
1694AEa, b1-Heptadecenetrtr
1695TSCDa, bAmorpha-4,9-dien-2-ol 0.1
1698TSa, bAcorenone 0.2
1700Aa, b, cHeptadecane0.30.2
1705TSGERa, b, cGermacrone1.1
1716ALa, bPentadecanal0.30.1
1719TSFa, b(E,E)-Farnesal tr
1725Oa, b2,6-Diisopropylnaphthalene 0.2
1727Fa, b, cMethyl tetradecanoatetr
1755Aa, b5-Methylheptadecanetr
1764Aa, b2-Methylheptadecanetr
1765Fa, b, cTetradecanoic acid 1.2
1772Oa, b, cBenzyl benzoatetr0.2
1784Oa, b, cPhenanthrene 0.1
1794AEa, b1-Octadecenetr0.1
1795Fa, b, cEthyl tetradecanoatetr
1800Aa, b, cOctadecane 0.1
1818ALa, bHexadecanaltrtr
1828Fa, b, cIsopropyl myristatetr0.1
1839Fa, b15-Pentadecanolide (syn. exaltolide)tr
1844TSFa, b(E,E)-2,6-Farnesyl acetatetr
1848CRa, bHexahydrofarnesyl acetone1.72.3
1862Fa, bPentadecanoic acid tr
1876Oa, b, cBenzyl salicylatetrtr
1883ALCa, b, c1-Hexadecanol tr
1894AEa, b1-Nonadecenetr
1900Aa, b, cNonadecanetr0.1
1921CRa, b(E,E)-5,9-Farnesyl acetonetr0.7
1928Fa, b, cMethyl hexadecanoatetrtr
1930Oa, b2-Methylanthracene tr
1941Fa, b(Z)-9-Hexadecenoic acid (syn. palmitoleic acid) 0.2
1950TDa, bIsophytoltr0.2
1968Fa, b, cHexadecanoic acidtr4.5
1975TDa, bSandaracopimara-8(14),15-dienetr
1982ALCa, b, c1-Heptadecanoltr
1994AEa, b1-Eicosenetrtr
1996Fa, b, cEthyl hexadecanoatetr0.2
2000Aa, b, cEicosanetr0.1
2003TDa, bManoyl oxide1.40.1
2025TDa, b13-epi-Manool oxide2.0
2034CRa, b(E,E)-Geranyl linalooltr
2070TDa, bar-Abietatrienetr
2094AEa, b1-Heneicosenetrtr
2100Aa, b, cHeneicosane0.30.1
2116TDa, b(E)-Phytoltr3.3
2116ALa, bNonadecanaltr
2136AEa, b, cLinoleic acid 0.3
2138Aa, bBranched alkanetr
2143Fa, b, cLinolenic acid 1.2
2155Fa, b(E,E)-9,12-Octadecadienoic acid (syn. linoleic acid) 0.8
2172AEa, b1-Nonadecanoltr
2180Aa, bBranched alkanetr
2194AEa, b1-Docosene0.8tr
2200Aa, b, cDocosane0.5tr
2219ALa, bEicosanal tr
2294AEa, b1-Tricosene0.3
2300Aa, b, cTricosane2.10.2
2395AEa, b1-Tetracosene1.4
2352Fa, bδ-Octadecalactonetr0.1
2394AEa, b1-Tetracosene tr
2400Aa, b, cTetracosane1.2tr
2495AEa, b1-Pentacosenetr
2500Aa, b, cPentacosane6.4tr
2596AEa, b1-Hexacosene1.1
2600Aa, b, cHexacosane0.6
2700Aa, b, cHeptacosane2.9
2297AEa, b1-Octacosene1.6
2900Aa, b, cNonacosane2.0
2998AEa, b1-Triacontenetr
3100Aa, b, cHentriacontanetr
Number of constituents187243
Terpenoids (T)49.546.8
Hemiterpenoids (TH)tr0.2
Monoterpenoids (TM)27.435.6
Oxygenated 27.435.6
Acyclic (TMA)7.614.7
p-Menthane (TMM)19.817.4
Bornane (TMB)0.02.2
Thujane (TMT)0.00.9
Pinane (TMP)tr0.4
Sesquiterpenoids (TS)18.77.4
Farnesane (TSF)5.70.1
Caryophyllane (TSCR)3.70.9
Eudesmane (TSED)3.01.4
Cadinane (TSCD)0.02.7
Germacrane (TSGER)1.1tr
Eremophylane (TSER)1.70.0
Salvialane, acorane, bisabolane, aromadendrane, cedrane, gurjunane (TS)0.61.0
Agarofurane (TSAG)1.80.0
Humulane (TSH)1.11.3
Diterpenoids (TD)3.43.6
Phenylpropanoids (PP)0.71.2
Fatty acid derived compounds (FAD)34.110.7
Alkanes (A)16.31.5
Alkenes (AE)5.20.4
Aldehydes (AL)0.30.1
Alcohols (ALC)0.9tr
“Green leaf” volatiles (GL)11.48.6
Fatty acids and fatty acid esters (F)1.711.8
Carotenoid derived compounds (CD)3.214.1
Maillard reaction products (MRP)1.82.9
1 Compounds listed in order of elution on HP-5MS column (RI- experimentally determined retention indices on the mentioned column by co-injection of a homologous series of n-alkanes C7-C29); 2 a: constituent identified by mass spectra comparison; b: constituent identified by retention index matching; c: constituent identity confirmed by co-injection of an authentic sample; 3 tr- trace (<0.05%); 4 syn.-synonym.
In respect to the skeleton-types of the identified constituents, the monoterpenoid fractions of both V. vitis-idaea and A. uva-ursi oils could be considered as rather simple. Interestingly, not taking into account some trace constituents, the monoterpenoid fractions of both oils were completely comprised of oxygenated derivatives. In V. vitis-idaea oil only acyclic (7.6%), p-menthane (19.8%) and pinane-type (tr) monoterpenoids were detected. Acyclic (14.7%) and monoterpenoids with a p-menthane (17.4%) skeleton dominated the monoterpenoid fraction of A. uva-ursi oil as well, and only small relative amounts of pinane (0.4%), bornane (2.2%) and thujane-type (0.9%) compounds were detected. α-Terpinyl cation, produced by the biosynthetic cyclization of linalyl diphosphate, the intermediate from which p-menthane type monoterpenoids are derived, is known to be the precursor of other classes of cyclic monoterpenoids including bornanes, pinanes and thujanes [24]. Biosynthesis of linalool is closely related to linalyl diphosphate, and α-terpineol could be considered as a direct biosynthetic product of α-terpinyl cation, formed by quenching the mentioned cation with water [24]. Both linalool and α-terpineol were by far the most abundant compounds in the monoterpenoid fractions of A. uva-ursi and V. vitis-idaea oils. Having the above mentioned in mind, one could speculate that both taxa have a relatively primitive monoterpenoid biosynthetic “apparatus”, capable of producing predominantly metabolites from the “beginning” of the mentioned metabolic pathway. It seems that a similar consideration stands for some other taxa from the genus Vaccinium as well. In different Vaccinium species (V. corrymbosum, V. oxycoccus, V. macrocarpon, V. arctostaphylos) α-terpineol and/or linalool were recognized as major, or one of the major volatile metabolites [14,25,26,27,28,29]. Nevertheless, this should be taken with a grain of salt, since only the volatile metabolites have been investigated. In the studied species monoterpenes could be potentially present as glycosides, and thus non-volatile under hydrodistillation and/or GC conditions. α-Terpineol and some other terpenoid compounds were previously also recognized as V. macrocarpon cuticle wax constituents [30]. According to Croteau et al., the presence of these compounds in the cuticle wax could suggest that these substances might have a certain role in the plants’ defense mechanisms [30].
Although the relative amount of volatile sesquiterpenoids was considerably lower than that of monoterpenoids in both A. uva-ursi and V. vitis-idaea oils, sesquiterpenoid fractions were, concerning skeleton-types of identified constituents, much more heterogenic (Table 1). A number of different skeleton-types of volatile sesquiterpenoids were dominant in the oils of the two taxa: farnesanes (5.7%), caryophyllanes (3.7%) eudesmanes (3.0%) in V. vitis-idaea oil and cadinanes (2.7%), eudesmanes (1.4%) and humulanes (1.3%) in A. uva-ursi oil.
It might be assumed that certain volatiles listed in Table 1, identified in both A. uva-ursi and V. vitis-idaea oils, could be considered artifacts of the isolation procedure, and not direct products of plant metabolism. For example, a number of compounds from the Table 1 are most probably products of Maillard-type reactions including the thermal fragmentation of amino acids and sugars, alone or in conjunction, during hydrodistillation [31]. “Green leaf” volatiles, on the other hand, are most probably produced by enzymatic degradation of unsaturated fatty acids, as in desiccation, i.e. as a stress-induced response of plants, produced during collection and preparation of plant samples [32]. Alongside “green leaf” and other fatty acid derived compounds (FAD), fatty acid and fatty acid esters (F) and carotenoid derived compounds (CD) represented more than one third of both analyzed oils. Volatile profiles of some other representatives of the genus Vaccinium were also dominated by FAD, F and/or CD compounds [13,33,34]. All these species could be considered as essential oil-poor species (oil yield less than 0.1%). All mentioned above seems to further corroborate the hypothesis proposed by us in a previous publication [10]. We have noticed that the correlation between the essential oil yield and composition (classes of compounds) exists [10]. Most frequently, essential oil-rich species (oil yield much higher than 0.1%) produce considerable amount of monoterpenoids or phenylpropanoids, while in the oils of essential oil-poor species, FAD, F and CD compounds are the dominant volatile metabolites [10].
As previously mentioned, there are no reports concerning the volatile metabolites of A. uva-ursi, and there are only two references on V. vitis-idaea volatiles, however different parts of the plant (berries instead of leaves), using a different methodology (minced berries were treated with a pectinolytic enzyme and after that volatiles of the obtained juice and pressed residue were separately studied), have been analyzed [11,12]. Volatile profile of V. vitis-idaea barriers differs significantly from the corresponding profile of the leaves. For example, the most dominant volatile of the pressed residue of minced berries was benzyl alcohol (40.2%), found only as the minor contributor of the leaves’ oil. α-Terpineol and linalool (dominant volatiles of V. vitis-idaea leaves) on the other hand, represented in total only 1.0% of berry extract. This plant organ specification, concerning production/accumulation of volatiles, is not unusual. For example, differences in the chemical composition of Artemisia absinthium root and aerial parts oils pointed out to the possibility that different metabolic pathways could be operational in different organs of the same plant species [35]. Still, some similarities between V. vitis-idaea berry and leaf essential oil profiles could be observed. For instance, fatty acid related compounds, one of the dominant groups of constituents in the leaf oil, represented a significant portion of the berry extract (ca. 20%) [11,12].
Both species analyzed herein belong to the plant family Ericaceae. The latter comprises some 100-125 genera and more than 3,000 species [36] that are, generally speaking, poorly studied in respect to volatile metabolites. Table 2 lists the Ericaceae taxa whose essential oils were previously chemically analyzed using a methodology comparable to that applied in this work [13,14,15,16,17,18,19,20,21,22,23]. Compositional data on the essential oils of the species listed in Table 2 (28 samples in total) were mutually compared by means of multivariate statistical analyses (MVA: AHC and PCA).
Table 2. List of essential oil samples used in statistical analyses.
Table 2. List of essential oil samples used in statistical analyses.
Taxon (plant part)Main oil constituentRef.1Des.2
Arctostaphylos uva-ursi (L.) Spreng. (leaves)α-Terpineol (7.8%)Present studyObs1
Vaccinium vitis-idaea (leaves)α-Terpineol (17.0%)Present studyObs2
V. arctostaphylos L. (shoots)Hexadecanoic acid (27.0%)[13]Obs3
V. arctostaphylos (aerial parts)α-Terpineol (15.0%)[14]Obs4
Rhododendron mucronatum G. don (flowers)Linolenic acid (39.7%)[15]Obs5
R. simii Planch. (flowers)Linolenic acid (36.4%)[15]Obs6
R. simii (leaves)Phytol3 (15.2%)[15]Obs7
R. naamkwanense Merr. (leaves)9,12-Octadecatienoic acid (45.3%)4[15]Obs8
R. anthopogon D. Don (aerial parts)α-Pinene (37.4%)[16]Obs9
R. aureum Georgi. (leaves)Calarene (34.4%)[17]Obs10
R. aureum (leaves)Calarene (66.4%)[17]Obs11
R. aureum (leaves)Calarene (26.2%)[17]Obs12
R. aureum (leaves)Calarene (41.3%)[17]Obs13
R. aureum (leaves)β-Bourbonene (27.4%)[17]Obs14
R. aureum (leaves)Calarene (48.8%)[18]Obs15
R. aureum (leaves)Calarene (36.2%)[18]Obs16
R. aureum (leaves)Calarene (16.2%)[18]Obs17
R. dauricum L. (leaves)trans-Caryophyllene (19.1%)[18]Obs18
R. dauricum (leaves)γ-Cadinene (17.4%)[18]Obs19
R. dauricum (leaves)trans-Caryophyllene (17.0%)[18]Obs20
R. tomentosum (Stokes) H. Harmaja (leaves) (former name Ledum palustre L.)Palustrol (22.8%)[19]Obs21
Ledum palustre L. var. angustum N. BuschAscaridole (26.8%)[20]Obs22
Erica manipuliflora Salisb. (aerial parts)Heptacosane (19.9%)[21]Obs23
E. manipuliflora (aerial parts)1-Octen-3-ol (16.2%)[21]Obs24
Gaultheria fragrantissima Wall. (leaves)Methyl salicylate (99.2%)[22]Obs25
G. fragrantissima (steams)Methyl salicylate (99.5%)[22]Obs26
G. fragrantissima (flowering twigs)Methyl salicylate (99.4%)[22]Obs27
Arbutus unedo L. (leaves)(E)-2-Decenal (12.0%)[23]Obs28
1 Ref.-reference; 2 Des.-designation; 3 Correct isomer not specified in the original reference; 4 Name of component (incomplete and unclear) given as in the original reference.
Figure 1. (a) Dendrogram (AHC analysis) representing chemical composition dissimilarity relationships of 28 essential oil samples (observations) obtained by Euclidian distance dissimilarity (dissimilarity within the interval [0, 27000], using aggregation criterion-Ward's method). Four groups of samples (C1-C4) were found. (b) Principal component analysis ordination of 28 oil samples (observations). Axes (F1 and F2 factors-the first and second principal component) refer to the ordination scores obtained from the samples. Axis F1 accounts for ca. 13% and axis F2 accounts for a further 11% of the total variance.
Figure 1. (a) Dendrogram (AHC analysis) representing chemical composition dissimilarity relationships of 28 essential oil samples (observations) obtained by Euclidian distance dissimilarity (dissimilarity within the interval [0, 27000], using aggregation criterion-Ward's method). Four groups of samples (C1-C4) were found. (b) Principal component analysis ordination of 28 oil samples (observations). Axes (F1 and F2 factors-the first and second principal component) refer to the ordination scores obtained from the samples. Axis F1 accounts for ca. 13% and axis F2 accounts for a further 11% of the total variance.
Molecules 15 06168 g001
This was done in order to determine, based on the essential oil profiles, possible mutual alliance of the taxa within the family, especially that of species from the genera Arctostaphylos and Vaccinium. Principal component analysis (PCA) and agglomerative hierarchical clustering (AHC) were both performed using the Excel program plug-in XLSTAT version 2008.6.07. Both methods were applied utilizing the mean values of the relative abundances of the constituents of compared essential oils as variables (only constituents with percentage higher than 1% in at least one sample were taken into account). AHC was determined using Pearson dissimilarity where the aggregation criterion were simple linkage, unweighted pair-group average and complete linkage and Euclidean distance where the aggregation criterion were weighted pair-group average, unweighted pair-group average and Ward’s method. PCA of the Pearson (n) type was performed. Results of the MVA analyses are given in Figure 1 and Figure 2. In the dendrogram of the AHC analysis (Figure 1), four different classes of samples (C1-C4) can be observed. Class C1 (Obs25-Obs27) groups essential oils (almost pure methyl salicylate) obtained from different parts of Gaultheria fragrantissima (wintergreen) [22]. Class C2 consists exclusively of Rhododendron aureum oils (Obs10-Obs17), all characterized with a high level of the sesquiterpene calarene [17,18]. Oils obtained from flowers of R. mucronatum and R. simii (Obs5 and Obs 6; high level of linolenic acid) form a separate class C3 [15]. All other samples [13,14,15,16,17,18,19,20,21,22,23], including those that correspond to A. uva-ursi (Obs1), V. vitis-idaea (Obs2) and V. arctostaphylos (Obs3 and Obs4) are recognized as statistically not different and grouped in C4. It must be stressed that samples Obs1-Obs4 are basically characterized by very low Euclidian distance. In the same time, different species from the genus Rhododendron are separated in statistically different groups (C2, C3 and C4) [15,20]. Results of AHC suggest that taxa from the genera Vaccinium and Arctostaphylos are closely related. This is observable from the PCA biplot as well (Figure 2), where A. uva-ursi (Obs1) and V. arctostaphylos (Obs4) oils are mutually characterized with similar values of F1 and F2 factors. Moreover, samples corresponding to Vaccinium, Arctostaphylos and Arbutus taxa (Obs1, Obs2, Obs4 and Obs28) are, based on PCA results, clearly separated from other considered oils (Figure 2). One could find results of both AHC and PCA a bit surprising, having in mind that classical taxonomy places genera Vaccinium and Arctostaphylos in different subfamilies of Ericaceae (Vaccinoidaea and Arbutoidaea) [37]. Results of molecular studies within the Ericaceae clearly separated taxa belonging to the mentioned genera [37,38]. Nevertheless, mutual alliance of Arbutus and Arctostaphylos (Arbutoidaea; Obs1, Obs22) is recognized by both molecular [37,38] and chemotaxonomical studies (present work).

3. Experimental

3.1. Plant material

Leaves of V. vitis-idaea were collected from the slopes of Stara Planina Mountain (near the mountain top Babin Zub), S. Serbia, at the beginning of July, 2007. Voucher specimens were deposited in the Herbarium of the Faculty of Science and Mathematics, University of Niš, under acquisition number 20074. Leaves of A. uva-ursi were obtained from a local pharmacy (in 2006). Botanical identification was performed by N.R.

3.2. Isolation of the essential oils

Air-dried, to constant weight, leaves of A. uva-ursi and V. vitis-idaea (three batches of about 500 g of each sample) was subjected to hydrodistillation with ca. 2 L of distilled water for 2.5 h using the original Clevenger-type apparatus [39]. The semi-solid yellowish essential oils (30 ± 1 mg per batch) of both species were obtained with a yield of 0.06% (w/w, typical value). Due to the small sample size of 30 mg of the isolated essential oils, which were not completely liquid, the volume of the oils was not measured. The obtained oils were separated by extraction with diethyl ether (Merck, Darmstadt Germany) and dried over anhydrous sodium sulfate (Aldrich, St. Louis, MO, USA). The solvent was evaporated under a gentle stream of nitrogen at room temperature, in order to exclude any loss of the essential oil, and immediately analyzed. When the oil yields were determined, after the bulk of ether was removed under a stream of N2, the residue was exposed to vacuum at room temperature for a short period to eliminate the solvent completely. The pure oil was then measured on an analytical balance and multiple gravimetric measurements were taken during 24 h to ensure that all of the solvent had evaporated.

3.3. Gas chromatography and gas chromatography-mass spectrometry

The GC/MS analysis was repeated three times for each sample using a Hewlett-Packard 6890N gas chromatograph. The gas chromatograph was equipped with a fused silica capillary column HP-5MS (5% phenylmethylsiloxane, 30 m × 0.25 mm, film thickness 0.25 μm, Agilent Technologies, Palo Alto, CA, USA) and coupled with a 5975B mass selective detector from the same company. The injector and interface were operated at 250 ºC and 300 ºC, respectively. The oven temperature was raised from 70 ºC to 290 ºC at a heating rate of 5 ºC/min and then isothermally held for 10 min. As a carrier gas helium at 1.0 mL/min was used. The samples, 1 μL of the oil solutions in diethyl ether (1:100), was injected in a pulsed split mode (the flow was 1.5 mL/min for the first 0.5 min and then set to 1.0 mL/ min throughout the remainder of the analysis; split ratio 40:1). mass selective detector was operated at the ionization energy of 70 eV, in the 35–500 amu range with a scanning speed of 0.34 s. GC (FID) analysis was carried out under the same experimental conditions using the same column as described for the GC/MS. The percentage composition was computed from the GC peak areas without the use of correction factors. Qualitative analysis of the essential oil constituents was based on several factors. Firstly, the comparison of the essential oils linear retention indices relative to retention times of C7-C31 n-alkanes on the HP-5MS column [40] with those reported in the literature [41]. Secondly, by comparison of their mass spectra with those of authentic standards, as well as those from Wiley 6, NIST02, MassFinder 2.3. Also, a homemade MS library with the spectra corresponding to pure substances and components of known essential oils was used, and finally, wherever possible, by coinjection with an authentic sample (Table 1). Relative standard deviation (RSD) of repeated measurements (independent sample preparations and GC-MS) was for all substances below 1%. The only exceptions which had higher RSD were minor components such as α-agarofuran, (E)-β-ionone, pulegone, safranal and dodecanoic acid where RSD was 2, 6, 7, 9 and 12%, respectively.

4. Conclusions

Comparison of the compositional data of the essential oils extracted from A. uva-ursi, V. vitis-idaea and 12 other Ericaceae taxa (six different genera; available literature data) pointed out to a high level of similarity of Vaccinium and Arctostaphylos species. Based on the identity and relative abundance of the dominant volatile metabolites produced by the compared Ericaceae taxa, it seems that the level of mutual correspondence between A. uva-ursi and V. vitis-idaea species is more significant than that of any of the two taxa and the rest of the compared species. This is partially due to the fact that α-terpineol and linalool were among the dominant contributors to the volatile profiles of both A. uva-ursi and V. vitis-idaea. Furthermore, the most abundant classes of compounds in both oils were basically the same (monoterpenoids, fatty acid derived compounds and carotenoid derived compounds). All stated above additionally corroborates the same pharmacological applications of two herbs. It must be stressed once again that essential oils may, despite the small yield, contribute to the medicinal properties of the plant [9].


The authors are very grateful to the Ministry of Science and Technological Development of Serbia (Project 142054 B), for the financial support of this work.
  • Sample Availability: Samples of the A. uva-ursi and V. vitis-idaea essential oils are available from the authors.

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MDPI and ACS Style

Radulović, N.; Blagojević, P.; Palić, R. Comparative Study of the Leaf Volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae). Molecules 2010, 15, 6168-6185.

AMA Style

Radulović N, Blagojević P, Palić R. Comparative Study of the Leaf Volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae). Molecules. 2010; 15(9):6168-6185.

Chicago/Turabian Style

Radulović, Niko, Polina Blagojević, and Radosav Palić. 2010. "Comparative Study of the Leaf Volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae)" Molecules 15, no. 9: 6168-6185.

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