FLAVOUR AND FRAGRANCE JOURNALFlavour Fragr. J. 2003; 18: 376–379Published online in Wiley InterScience (www.interscience.wiley.com). DOI: 10.1002/ffj.1197

Copyright © 2003 John Wiley & Sons, Ltd.

John Wiley & Sons, Ltd.

Chemical composition of fruit and stem essential oils of Lantana camara from northern IndiaEssential Oils of Lantana CamaraM. Khan,1 S. K. Srivastava,1* Neetu Jain,1 K. V. Syamasundar2 and Anju K. Yadav1

1 Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Lucknow 226016, India2 Central Institute of Medicinal and Aromatic Plants, Field Station, GKVK PO, Bangalore 560065, India

Received 15 April 2002Revised 17 July 2002Accepted 15 August 2002

ABSTRACT: The chemical composition of fruits and stem essential oils of Lantana camara from the northernplains of India were analysed by GC and GC–MS, which resulted in the identification of 52 and 66 constituents,representing 98.1% and 96.6% of the oils, respectively. The major constituents in the fruits oil were palmitic acid(22.8%), stearic acid (12.8%) and germacrene-D (7.1%), while the major constituents in the stem oil were palmiticacid (32.7%) and stearic acid (23.9%). Copyright © 2003 John Wiley & Sons, Ltd.

KEY WORDS: Lantana camara; Verbenaceae; essential oils composition; palmitic acid; stearic acid; germacrene-D

Introduction

Lantana camara Linn. (Verbenaceae) is a stragglingplant found over a wide area of the tropical and sub-tropical regions of the world.1,2 It is native to tropicalAmerica and was introduced in India as an ornamentaland hedge plant. Now it is commonly available through-out India as an obnoxious weed. The flowers are small,usually yellow or orange changing to red or scarlet, indense axillary heads.3 The plant is known to be toxicto grazing animals, which, on ingestion of the leaves,develop hepatotoxicity and photosensitization.4 This tox-icity is believed to be due to the presence of lantadene-A and lantadene-B in the plant.5

On the other hand, different parts of the plant havebeen reported to be a rich source of various bioact-ive principles.6–10 The extract of L. camara roots hasbeen reported to possess antimalarial activity againstPlasmodium falciparum,11 while its lotion is used infolk medicines for the treatment of toothache, wounds,cuts, ulcers and swellings.12 Recently, roots of L. camarahave been reported as a potential source of putativehepatoprotective agent oleanolic acid.13

L. camara spreads rapidly in sunny environment andin India it is threatening many native plant species. Inorder to make commercial use of this obnoxious weed,extensive work is being carried out at our institute andvarious parts of the world. In our earlier investigation,we reported the chemical composition of leaf and flower

essential oils of L. camara from India.14 To the best ofour knowledge, no detailed investigations on the essen-tial oil composition of L. camara fruits and stems havebeen carried out. This prompted us to carry out detailedGC and GC–MS examination of fruits and stem essentialoils of L. camara.

Experimental

Plant Materials

The fruits and stem of L. camara were collected in themonth of December 2000, from the Kukrail ReservedForest, Lucknow. A voucher specimen has been depositedin the Herbarium Division of the Institute.

Isolation of Volatile Components

The crushed fresh fruits and chopped stem were sub-jected to hydrodistillation in a conventional Clevenger-type apparatus for 4 h. The yield of volatile oils wasvery poor, i.e. 0.02% and 0.01% (v/w), respectively. Theoils were dried over anhydrous sodium sulphate andstored at 4 °C until analysed.

Gas Chromatography (GC)

GC analysis of the oil was performed on a Perkin-ElmerGC 850 gas chromatograph equipped with FID, using afused silica capillary column (25 m × 0.25 mm i.d., filmthickness 0.25 µm), coated with dimethyl polysiloxane

* Correspondence to: S. K. Srivastava, Central Institute of Medicinal andAromatic Plants, PO CIMAP, Lucknow 226015, India. E-mail: santoshkumar_1955@yahoo.comContract/grant sponsor: Department of Biotechnology, Government of India.

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Copyright © 2003 John Wiley & Sons, Ltd. Flavour Fragr. J. 2003; 18: 376–379

(BP-1). The oven temperature was programmed from60 °C to 220 °C at 5 °C/min, then held isothermal at220 °C for 5 min, then heated at 3 °C/min to 245 °C andheld isothermal at 245 °C for 5 min. Injector temper-ature, 250 °C; detector temperature, 300 °C; carrier gas,nitrogen, at an inlet pressure of 10 psi; split, 1:80.

Gas Chromatography–Mass Spectrometry (GC–MS)

GC–MS data were obtained on a Perkin-Elmer TurboMass spectrometer using a PE-Wax column (60 m ×0.32 mm i.d., film thickness 0.25 µm). Carrier gas,helium; temperature program, 5 min at 70 °C, rising at2 °C/min to 120 °C, then at 3 °C/min to 240 °C.

Identification of Compounds

Compounds were identified by comparing the retentionindices of the peaks on the BP-1 column with literaturevalues.15–23 Final confirmation of constituents weremade by computer matching of the mass spectra ofpeaks with Wiley and NIST libraries and with publisheddata.24–27 Relative amounts of individual componentsare based on peak areas obtained without FID responsefactor correction. The retention indices were obtainedfrom gas chromatograms by logarithmic interpolationbetween bracketing n-alkanes. The homologous series ofn-alkanes (C8–C22; Poly Science; Niles, USA) were usedas standards.

Results and Discussion

The volatile oils were obtained by conventional hydro-distillation of fruits and stem of L. camara in a Clevenger-type apparatus. Each gave an oil in 0.02% and 0.01%yield (v/w) on a fresh weight basis. GC and GC–MSanalysis resulted in the identification of a total of 52 and66 constituents from the fruit and stem oils, respectively.The relative concentrations of the volatile componentsidentified are presented in the Table 1, according to theirelution order on a BP-1 column. The main constituentsin the fruit and stem oils were: palmitic acid (RI 1962,22.8% and 32.7%); stearic acid (RI 2170, 12.8% and23.9%); and germacrene-D (RI 1484, 7.1% and 3.6%).

From Table 1 it is evident that the fruit oil almostmatched with the stem oil in respect to its chemical con-stituents but differed significantly with respect to thepercentage composition of its constituents. In the fruit oil,contents of (E)-nerolidol (RI 1552), γ-curcumenal (RI1742) and (−)-italicene ether (RI 1524) were 5–7 timesgreater, while β-elemene (RI 1391), α-humulene (RI 1458),β-caryophelleneoxide (RI 1577) and 1-epi-cubenol (RI

1625) were approximately 3 times greater. On the otherhand, contents of linalool (RI 1086), β-caryophyllene(RI 1425), germacrene-D (RI 1484), sesquiphellandrene(RI 1520), calacorene (RI 1538) and α-cadinol (RI1652) were 1.5–2 fold greater than in the stem oil. How-ever, it is interesting to note that contents of the majorconstituents stearic acid (RI 2170) and palmitic acid (RI1962), along with 9,12,15-octadecatrienoic acid ethylester (RI 2148) were 1.5–2-fold greater in the stem oilthan in the fruit oil.

On comparing our present results of fruit and stemoils with our earlier result on leaf and flower oils (seeTable 1), it is evident that the major compounds in theleaf and the flower oils were germacrene-D (RI 1484,20.5% and 10.6%), γ-elemene (RI 1498, 10.3% and 6.8%),β-caryophyllene (RI 1425, 9.4% and 7.0%), β-elemene(RI 1391, 7.3% and 14.5%), α-copaene (RI 1380, 4.9%and 10.7%), and α-cadinene (RI 1434, 3.3% and 7.2%),while in the fruit and stem oils, the major compounds, asdiscussed earlier, were palmitic acid (RI 1962), stearicacid (RI 2170) and germacrene-D (RI 1484). Apart fromthe above differences in the major compounds in fruitand stem vs. leaf and flowers, it is significant to notethat, of 51 constituents in fruit oil, 40 and 42 constitu-ents matched with the leaf and flower oil constituents,respectively. Similarly, of 66 constituents in the stemoil, 48 and 49 constituents matched with leaf and floweroil constituents, respectively. The other compounds,which were present in appreciable amounts in all theoils, were germacrene-D (RI 1484), linalool (RI 1086),α-copaene (RI 1380), β-elemene (RI 1391), β -caryophyllene(RI 1425), α-cadinene (RI 1434), α-humulene (RI 1458),allo-aromadendrene (RI 1476), γ -elemene (RI 1498),sesquiphellandrene (RI 1520), β-caryophylleneoxide(RI 1577), 1-epi-cubenol (RI 1625), epi-α-cadinol (RI 1642)and α-cadinol (RI 1652).

Acknowledgements— The authors are grateful to Dr S. P. S. Khanuja,Director, CIMAP, and Dr S. K. Agarwal, Head, Aromatic Plants Chem-istry Division, for their keen interest in this work. Financial assistanceto one of us (MK) by the Department of Biotechnology, Government ofIndia, for the gene bank work, is also gratefully acknowledged.

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378 M. KHAN ET AL.

Table 1. Percentage composition of fruit and stem essential oils of Lantana camara from the plains ofnorthern India

Constituents RI Fruits (%) Stem (%) Leavesa (%) Flowersa (%)

cis-3-Hexenol 850 — — 0.1 —n-Heptanol 880 — — — 0.1α-Thujene 925 — — 0.2 —α-Pinene 934 0.2 0.2 2.1 —Camphene 947 — — 0.1 —Sabinene 969 0.2 0.3 2.3 0.1β-Pinene 973 0.2 0.2 1.8 —Myrcene 984 0.1 0.1 1.7 —(Z)-3-Hexenyl acetate 996 — 0.2 0.2 —n-Decane 1004 — — 1.4 0.2α-Phellandrene 1009 — — 0.3 —δ-3-Carene 1012 — 0.1 1.5 1.8p-Cymene 1022 — 0.1 0.9 0.2(Z)-β-Ocimene 1028 — — 0.5 —(E)-β-Ocimene 1040 — — 0.7 0.1γ-Terpinene 1052 — 0.2 2.6 —Terpinolene 1080 — 0.1 0.2 —Linalool 1086 1.9 1.1 0.7 0.8cis-Sabinene hydrate 1091 — 0.3 — —n-Undecane 1096 — 0.2 — —Camphor 1125 — — 0.1 0.1trans-Pinene hydrate 1135 — 0.1 — —trans-Verbenol 1145 — 0.2 — —Borneol 1156 — 0.5 0.2 0.2Terpinen-4-ol 1167 0.4 0.8 0.5 0.2α-Terpineol 1179 0.9 0.6 0.4 0.3Octanoic acid 1200 — 0.4 — —Nerol 1218 0.3 0.2 0.1 0.3Geraniol 1249 0.9 0.9 — 0.3Safrole 1257 — — 0.2 —Geranyl formate 1282 — — 0.2 —iso-Safrole 1296 0.2 0.3 — 0.1Eugenol 1337 0.6 0.6 0.8 1.3δ-Elemene 1342 — — 0.1 —α-Cubebene 1351 0.3 0.2 0.3 0.3Geranyl acetate 1362 — 0.1 — 0.1α-Copaene 1380 1.8 1.6 4.9 10.7β-Elemene 1391 2.5 0.8 7.3 14.5Tetradecane 1401 — 0.4 0.1 0.1α-Cedrene 1414 — — 0.1 0.1β-Caryophyllene 1425 2.0 1.4 9.4 7.0α-Cadinene 1434 1.7 1.3 3.3 7.2α-Bergamotene 1440 0.1 0.2 0.5 0.5Geranyl propionate 1447 0.4 0.1 0.2 0.1(Z)-β-Farnesene 1451 — — 0.1 0.2α-Humulene 1458 2.4 0.7 2.7 2.7(E)-β-Farnesene 1466 0.4 0.3 1.1 1.7allo-Aromadendrene 1476 1.8 0.7 0.8 1.2Germacrene-D 1484 7.1 3.6 20.5 10.6α-Zingiberene 1490 0.6 0.4 1.7 1.5γ-Elemene 1498 2.6 2.2 10.3 6.8β-Curcumene 1503 0.6 0.5 0.1 0.9β-Bisabolene 1505 — — 0.1 —Cubebol 1512 0.2 0.2 — —Sesquiphellendrene 1520 3.1 2.3 1.6 1.2(−) Italicene ether 1524 4.6 0.6 — —Calacorene 1538 1.2 0.6 0.4 0.5Germacrene-B 1544 — — 0.2 0.4(E)-Nerolidol 1552 1.1 0.2 0.6 0.7Spathulenol 1563 0.8 0.3 1.3 2.0Acora-3,5-diene-11-ol 1568 — — 0.1 0.2β-Caryophylleneoxide 1577 2.6 1.0 2.1 2.5Viridifloral 1588 — — 0.3 0.1Humulene oxide-II 1595 0.6 0.3 0.1 0.2n-Hexadecane 1602 — — 0.1 —Helifolen-12-al 1608 0.4 0.2 0.5 0.6Cubenol 1614 0.5 0.4 1.0 0.8T-Cadinol 1620 — — 0.3 0.51-epi-Cubenol 1625 2.0 0.7 1.1 1.8

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epi-α-Cadinol 1642 1.2 0.8 1.7 1.4α-Cadinol 1652 2.2 1.1 1.8 2.5(E)-Sesquithujene-12-ol 1665 — — 0.1 —α-Bisabolol 1667 0.7 0.4 0.2 1.5epi-α-Bisabolol 1684 1.1 0.5 0.5 0.5n-Heptadecane 1692 0.2 1.2 0.1 0.4(Z)-α-trans-Bergamotol 1700 0.9 — — —(E)-Farnesol 1704 — — 0.3 1.0epi-α-Bisabol-1-one 1720 — — 0.1 0.9γ-Curcumenal 1742 3.4 0.5 0.2 0.2Tetradecanoic acid 1763 — 0.3 — 1.4n-Octadecane 1798 0.2 0.3 0.1 0.3Hexadecanal 1812 — — — 0.1n-Nuciferyl acetate 1830 1.1 0.1 0.1 0.3Pentadecanoic acid 1869 — 0.1 0.1 0.5Heptadecan-2-one 1889 — — — 0.1n-Nonadecane 1896 0.3 0.3 — 0.9(E,E)-Farnesyl acetone 1911 — — — 0.4Oleic acid 1936 0.8 0.3 — 0.4Palmitic acid 1962 22.8 32.7 — 0.2Phytol 2105 0.7 0.6 — —Methyl octadecanoate 2130 0.4 0.4 — —9,12,15-Octadecatrienoic acid, ethyl ester 2148 2.0 4.1 — —1-Nonadecanol 2150 — — 0.6 —Stearic acid 2170 12.8 23.9 — —

a Taken from reference 14.

Constituents RI Fruits (%) Stem (%) Leavesa (%) Flowersa (%)

Table 1. (Continued )

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