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Original Article
9 (
6
); 764-774
doi:
10.1016/j.arabjc.2015.11.005

Characterization of leaves and flowers volatile constituents of Lantana camara growing in central region of Saudi Arabia

, ,
 Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia

⁎Corresponding authors. Tel.: +966 1 4675910; fax: +966 1 4675992. mkhan3@ksu.edu.sa (Merajuddin Khan), khathlan@ksu.edu.sa (Hamad Z. Alkhathlan)

Received: , Accepted: ,
© The Author(s) 2015
Disclaimer:
This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.

Peer review under responsibility of King Saud University.

Abstract

The chemical components of essential oils derived from leaves and flowers of Lantana camara growing in Saudi Arabia are analyzed for the first time using gas chromatography techniques (GC–MS, GC–FID, Co-GC, LRI determination, and database and literature searches) on two different stationary phase columns (polar and nonpolar). This analysis led to the identification of total 163 compounds from leaves and flowers oils. 134 compounds were identified in the oil obtained from leaves of L. camara, whereas 127 compounds were identified in the oil obtained from flowers; these compounds account for 96.3% and 95.3% of the oil composition, respectively. The major components in the oil from leaves were cis-3-hexen-1-ol (11.3%), 1-octen-3-ol (8.7%), spathulenol (8.6%), caryophyllene oxide (7.5%) and 1-hexanol (5.8%). In contrast, the major compounds in the flowers oil were caryophyllene oxide (10.6%), β-caryophyllene (9.7%), spathulenol (8.6%), γ-cadinene (5.6%) and trans-β-farnesene (5.0%). To the best of our knowledge, cis-3-hexen-1-ol and 1-octen-3-ol that were identified as major components in this study have not been reported earlier from Lantana oils.

Keywords

Verbenaceae
Essential oils
cis-3-Hexen-1-ol
1-Octen-3-ol
β-Caryophyllene
Lantana camara
1

1 Introduction

Lantana is a genus of both herbaceous plants and shrubs containing about 150 species and belongs to the family Verbenaceae (Ghisalberti, 2000). Lantana camara is an evergreen climbing aromatic shrub of the genus Lantana and is considered to be one of the most important medicinal plants of the world (Sharma et al., 2000; Srivastava et al., 2005). It can grow up to 2–4 m in height under normal conditions but has the ability to climb up to 15 m in height with the support of surrounding vegetation (Day et al., 2003). L. camara is native to tropical regions of America and Africa, but now, it has been introduced as an ornamental plant in most countries worldwide including Saudi Arabia and has been completely naturalized in most tropical and subtropical parts of the world as it can easily grow and survive in variety of agro-climatic conditions (Sharma, 1981).

L. camara have been widely used in traditional medicine for the treatment of malaria, ulcers, cancer, high blood pressure, tetanus, tumors, eczema, cuts, catarrhal infections, atoxy of abdominal viscera, chicken pox, measles, rheumatism, asthma and fevers (Day et al., 2003; Ghisalberti, 2000; Lenika et al., 2005; Sathish et al., 2011). It is an excellent provenance for several classes of bioactive natural products including triterpenoids, flavonoids, steroids, iridoide glycosides, oligosaccharides, phenylpropanoid glycosides, and naphthoquinones (Begum et al., 2014; Sharma et al., 2007; Sousa et al., 2012). Varieties of lead phytomolecules such as oleanolic acid, ursolic acid, lantanoside, linaroside, camarinic acid, verbascoside, umuhengerin and phytol have been isolated from L. camara and their various biological activities such as hepatoprotective, leishmanicidal, anticancer, antibacterial, antioxidant, antimycobacterial, nematicidal, and antiulcer have been reported (Begum et al., 2014, 2008, 1995; Day et al., 2003; Herbert et al., 1991; Sathish et al., 2011; Qamar et al., 2005). Roots of L. camara have been described to be a rich and an inexpensive source of putative biologically active compound “oleanolic acid” for which some optimized and economical isolation procedures have been described and the isolation process has been patented (Banik and Pandey, 2008; Misra et al., 1997; Srivastava et al., 2005; Verma et al., 2013). Moreover, L. camara has been proven to be one of the most easily available and cheap materials for the isolation of industrial essential oils famously known as Lantana oils (Randrianalijaona et al., 2005; Weyerstahl et al., 1999). Essential oils isolated from various parts of L. camara from different regions of the world have previously been studied (Filho et al., 2012; Kasali et al., 2004; Khan et al., 2002; Love et al., 2009; Ngassoum et al., 1999; Padalia et al., 2010; Sefidkon, 2002; Sundufu and Shoushan, 2004) and shown to possess various biological activities such as anti-inflammatory (Benites et al., 2009), antibacterial (Tesch et al., 2011), antioxidant (Sousa et al., 2013), insecticidal (Zoubiri and Baaliouamer, 2012b), allelopathic (Verdeguer et al., 2009) and larvicidal (Dua et al., 2010). Owing to the rapid propagation, invasive nature and abundant availability of L. camara, extensive research work in several parts of the world are going on in order to make this plant more useful for industrial applications (Passos et al., 2012; Patel, 2011; Sousa et al., 2013). In continuation of our research interest in exploring various medicinal and aromatic plants grown in diverse agro-climatic conditions (Al-Mazroa et al., 2015; Al-Otaibi et al., 2014; Khan et al., 2014, 2012, 2006), we have previously reported essential oil compositions of L. camara from India and developed an economical process for the isolation of hepatoprotective agent “oleanolic acid” from the root of L. camara (Khan et al., 2003; Srivastava et al., 2005). Herein, we are reporting detail chemical characterization of volatile constituents of leaves and flowers essential oils of L. camara grown in Saudi Arabia using GC–FID and GC–MS analyses as well as linear retention indices (LRI) measurements performed on both polar and nonpolar columns. To the best of our knowledge, this is the first report on phytochemical investigation of L. camara growing in Saudi Arabian agro-climatic conditions.

2

2 Experimental

2.1

2.1 Plant material

The whole plant of L. camara was procured from Riyadh, central part of Saudi Arabia during the flowering stage in the month of April 2011. The identification of the plant species was confirmed by a botanical taxonomist (Dr. Jacob Thomas Pandalayil) from the Herbarium Division, College of Science, King Saud University, Riyadh, KSA. The voucher specimen (No. KSUHZK-301) of the plant material is maintained in our laboratory.

2.2

2.2 Isolation of essential oils

The leaves and flowers from freshly collected L. camara plant material were separated and sliced into small pieces. The sliced fresh leaves (290.0 g) and flowers (475.0 g) were separately subjected to hydro-distillation for 3 h using a Clevenger-type apparatus according to the European Pharmacopoeia method (European Pharmacopoeia, 1996) to give light-orange color oils. The oils obtained after the hydro-distillation were dried over anhydrous sodium sulfate and stored at 4 °C until further use. The yield of the volatile oils derived from the leaves and flowers was 0.06% and 0.08% (w/w), respectively, on the fresh weight basis.

2.3

2.3 Chemicals

Analytical-grade acetone (Sigma–Aldrich, Germany) was used for the dilution of oil samples. Pure volatile compounds such as linalool, nonanal, limonene, terpinene-4-ol, eugenol, α-bisabolol, and α-terpinolene were available in our laboratory and used for co-injection analysis.

2.4

2.4 GC–FID and GC–MS analyses

The essential oils were analyzed using a GC–MS and GC–FID equipped with two columns, one of which was polar (DB-Wax), and the other was nonpolar (HP-5MS). GC–MS was performed on an Agilent single-quadrupole mass spectrometer with an inert mass selective detector (MSD-5975C detector, Agilent Technologies, USA) coupled directly to an Agilent 7890A gas chromatograph which was equipped with a split–splitless injector, a quickswap assembly, an Agilent model 7693 autosampler and a HP-5MS fused silica capillary column (5% phenyl 95% dimethylpolysiloxane, 30 m × 0.25 mm i.d., film thickness 0.25 μm, Agilent Technologies, USA). Supplementary analyses were performed on a DB-Wax fused silica capillary column (polyethylene glycol, 30 m × 0.25 mm i.d., film thickness 0.25 μm, Agilent Technologies, USA). The HP-5MS column was operated using an injector temperature of 250 °C and the following oven temperature profile: an isothermal hold at 50 °C for 4 min, followed by a ramp of 4 °C/min to 220 °C, an isothermal hold for 2 min, a second ramp to 280 °C at 20 °C/min and finally an isothermal hold for 15 min. Conversely, the DB-Wax column was operated using an injector temperature of 250 °C and the following oven temperature profile: an isothermal hold at 40 °C for 4 min, followed by a ramp of 4 °C/min to 220 °C and an isothermal hold for 10 min.

Approximately 0.2 μl of each sample diluted in acetone (5% solution in acetone) was injected using the split injection mode; the split flow ratio was 10:1. The helium carrier gas was flowed at 1 ml/min. The GC–TIC profiles and mass spectra were obtained using the ChemStation data analysis software, version E-02.00.493 (Agilent). All mass spectra were acquired in the EI mode (scan range of m/z 45–600 and ionization energy of 70 eV). The temperatures of the electronic-impact ion source and the MS quadrupole were 230 °C and 150 °C, respectively. The MSD transfer line was maintained at 280 °C for both polar and nonpolar analyses. The GC analysis was performed on an Agilent GC-7890A dual-channel gas chromatograph (Agilent Technologies, USA) equipped with FID using both polar (DB-Wax) and nonpolar (HP-5MS) columns under the same conditions as described above. The detector temperature was maintained at 300 °C for both polar and nonpolar analyses. The relative composition of the oil components was calculated on the basis of the GC–FID peak areas measured using the HP-5 MS column without using correction factor. Results are reported in Table 1 according to their elution order on the HP-5MS column.

Table 1 Composition of essential oils derived from leaves and flowers of Lantana camara from the central region of Saudi Arabia.
Sl. No. Compound⁎ LRIa LRIp LCL (%) LCF (%)
1 2,2-Diethoxypropane 777 – 1.0 t
2 Hexanal 800 1080 0.1 –
3 trans-3-Hexen-1-ol 849 1367 0.3 –
4 trans-2-Hexenal 850 1216 0.3 –
5 cis-3-Hexen-1-ol 852 1388 11.3 –
6 2-Methyl-butanoic acid 856 1662 – 0.1
7 trans-2-Hexen-1-ol 859 1410 0.1 –
8 cis-2-Hexen-1-ol 863 – 0.6 –
9 1-Hexanol 865 1357 5.8 –
10 1,3,5,7-Cyclooctatetraene 890 – 0.2 0.3
11 n-Nonane 900 900 0.1 –
12 (2E)-Heptenal 954 – 0.1 0.1
13 Benzaldehyde 960 1512 – t
14 Verbenone 969 1122 0.1 –
15 Sabinene 973 1121 0.1 –
16 1-Octen-3-ol 978 1454 8.7 1.8
17 3-Octanone 987 1255 0.1 t
18 6-Methyl-5-hepten-2-ol 992 1467 0.1 –
19 3-Octanol 994 1397 0.4 0.1
20 p-Cymene 1025 1268 – t
21 Limonene 1029 1196 0.1 0.1
22 Benzyl alcohol 1033 1881 0.2 –
23 trans-β-Ocimene 1047 – 0.1 0.1
24 trans-2-Octen-1-ol 1063 1611 t –
25 n-Octanol 1070 1556 – 0.1
26 cis-Linalool oxide 1073 1447 0.1 0.1
27 α-Terpinolene 1088 – 0.1 –
28 trans-Sabinene hydrate 1095 1554 0.1 –
29 Linalool 1099 1550 3.0 0.3
30 Nonanal 1104 1394 – 0.1
31 cis-Thujone 1109 1419 0.2 –
32 cis-p-Menth-2-en-1-ol 1122 1614 0.1 t
33 trans-p-Menth-2-en-1-ol 1137 1585 0.1 t
34 cis-Sabinol 1140 – 0.5 0.1
35 cis-Verbenol 1142 1661 0.2 t
36 trans-Verbenol 1146 1685 1.1 0.2
37 iso-Borneol 1157 1669 0.2 –
38 Pinocarvone 1165 1571 0.1 t
39 Borneol 1167 1707 0.4 0.1
40 Lavandulol 1170 – 0.1 t
41 1-Nonanol 1174 – 0.1 –
42 Terpinen-4-ol 1179 1606 0.2 0.1
43 p-Cymene-8-ol 1186 1853 0.1 0.1
44 α-Terpineol 1191 1701 0.2 0.1
45 Myrtenol 1198 1799 0.1 t
46 cis-Piperitol 1203 1712 0.1 0.1
47 n-Decanal 1208 1495 t –
48 Verbenone 1211 – 0.5 0.2
49 Linalyl formate 1215 1577 0.1 –
50 trans-Carveol 1220 1840 0.1 t
51 Cuminaldehyde 1242 1785 t –
52 Piperitone 1254 – – t
53 n-Decanol 1271 1756 t 0.1
54 n-Tridecane 1299 1300 – 0.1
55 trans-Pinocarvyl acetate 1302 1653 0.1 0.2
56 (2E,4E)-Decadienal 1321 1810 – 0.1
57 Myrtenyl acetate 1325 1693 0.1 –
58 α-Terpinyl acetate 1349 – 0.1 –
59 α-Cubebene 1353 1459 0.1 0.1
60 Eugenol 1359 – 0.2 –
61 n-Decanoic acid 1372 2274 0.1 0.1
62 α-Copaene 1380 1493 0.2 1.7
63 β-Bourbonene 1390 1524 – t
64 β-Cubebene 1394 1540 0.2 0.6
65 β-Elemene 1399 1590 0.1 0.1
66 n-Tetradecane 1401 1400 0.1 0.1
67 α-Cedrene 1412 1587 0.1 0.1
68 cis-α-Bergamotene 1415 1559 – t
69 β-Caryophyllene 1425 1599 3.1 9.7
70 β-Copaene 1435 – 0.2 0.7
71 trans-α-Bergamotene 1438 1578 – t
72 cis-β-Farnesene 1446 1655 – 0.1
73 trans-β-Farnesene 1458 1667 0.7 5.0
74 α-Humulene 1460 1673 – 1.0
75 dehydro-Aromadendrene 1465 1981 – 0.1
76 allo-Aromadendrene 1467 1649 0.3 0.7
77 (+)-epi-Bicyclosesquiphellandrene 1473 1594 0.4 0.1
78 trans-Cadina-1(6),4-diene 1479 2167 0.1 –
79 γ-Muurolene 1481 1691 0.3 0.8
80 Germacrene-D – 1712 t –
81 α-Curcumene 1486 1775 0.4 1.7
82 trans-β-Ionone 1489 1942 0.9 0.1
83 Calamenene-10,11-epoxide 1495 1890 0.1 –
84 α-Zingiberene 1496 1718 – 0.1
85 epi-Cubebol 1500 1895 0.8 2.0
86 Bicyclogermacrene 1503 1737 0.1 –
87 α-Muurolene 1505 – 0.3 0.9
88 α-Cuprenene 1508 2055 0.1 0.1
89 β-Bisabolene 1511 1729 0.7 2.6
90 β-Curcumene 1516 1743 0.1 –
91 γ-Cadinene 1521 1761 3.6 5.6
92 β-Sesquiphellandrene 1525 1768 0.1 –
93 δ-Cadinene 1528 1837 0.9 0.7
94 trans-Cadina-1(2),4-diene 1538 1924 0.3 0.2
95 trans-α-Bisabolene 1540 – 0.3 –
96 α-Cadinene 1543 1767 – 0.1
97 α-Calacorene 1547 1920 0.5 0.8
98 cis-Muurol-5-en-4-β-ol 1554 2029 – 0.5
99 Germacrene-B 1556 1823 – 0.2
100 Occidentalol 1557 2236 0.6 –
101 cis-Muurol-5-en-4-α-ol 1560 2092 0.2 0.6
102 trans-Nerolidol 1565 2043 0.3 0.5
103 β-Calacorene 1569 1963 – 0.2
104 Dodecanoic acid 1571 2489 0.3 –
105 Acora-3,5-dien-11-ol 1576 – – 0.4
106 Germacrene-D-4-ol 1574 2058 0.4 0.3
107 β-Copaene-4-α-ol 1579 2135 0.4 0.3
108 Spathulenol 1585 2125 8.6 8.6
109 Gleenol 1589 2038 – 2.2
110 Caryophyllene oxide 1591 1991 7.5 10.6
111 Viridiflorol 1596 2080 0.2 0.3
112 Longiborneol 1599 2157 0.4 0.5
113 α-Humulene oxide 1603 2019 0.1 0.1
114 β-Atlantol 1607 2012 0.5 0.6
115 Humulene epoxide II 1612 2045 0.4 0.6
116 Tetradecanal 1615 – 0.6 0.7
117 1-epi-Cubenol 1617 – 0.8 0.8
118 Acora-2,4 (15)-dien-11-ol 1625 – 0.2 0.2
119 10-epi-Acora-3,5-dien-11-ol 1629 – – 0.2
120 α-Acorenol 1635 2161 0.3 0.7
121 allo-Aromadendrene oxide 1638 2008 0.6 0.9
122 epi-α-Muurolol 1645 2183 1.9 0.6
123 τ-Cadinol 1647 – 0.7 2.6
124 β-Eudesmol 1652 2223 0.8 1.0
125 11-epi-6,10-Epoxybisabol-3-en-12-al 1656 – 0.2 0.3
126 α-Cadinol 1661 2393 0.9 3.6
127 cis-Calamenene-10-ol 1665 2315 0.3 0.4
128 Tridecanoic acid 1671 2613 0.4 0.4
129 trans-Calamenene-10-ol 1674 2341 0.2 0.4
130 β-Bisabolol 1677 2142 1.9 0.7
131 Cadalene 1682 2211 0.3 0.4
132 epi-α-Bisabolol 1686 – – 0.3
133 α-Bisabolol 1688 2222 0.4 0.5
134 cis-Apritone 1693 2144 0.6 0.5
135 (Z,Z)-Farnesol 1695 2322 – 0.4
136 n-Heptadecane 1702 1700 0.3 –
137 10-nor-Calamenene-10-one 1705 2353 0.3 0.4
138 trans-Apritone 1714 – 0.6 0.4
139 cis-Nuciferal 1718 – 0.2 0.2
140 (Z,E)-Farnesol 1726 2366 0.7 0.6
141 trans-Nuciferal 1730 – 0.1 0.4
142 Oplopanone 1745 2474 0.5 0.7
143 Xanthorrhizol 1750 - 0.4 0.4
144 trans-Nuciferol 1755 – – 0.5
145 Tetradecanoic acid 1770 2689 1.3 2.9
146 8,8-Dimethyl-9-methylene-1,5-cycloundecadiene 1775 – 0.4 0.5
147 14-Hydroxy-α-muurolene 1783 2103 – 0.2
148 n-Octadecane 1800 1800 0.3 0.4
149 Hexadecanal 1818 2131 0.2 0.4
150 Avocadynofuran 1825 1938 – 0.6
151 n-Nuciferyl acetate 1832 – 1.0 0.9
152 Eudesm-7(11)-en-4-ol, acetate 1848 – – 0.1
153 (Z,Z)-Farnesyl acetone 1850 – – 0.4
154 Pentadecanoic acid 1871 – 0.2 0.2
155 Nonadecane 1900 1900 0.1 0.4
156 Heptadecane-2-one 1902 2232 0.1 0.4
157 (E,E)-Farnesyl acetone 1920 2378 0.4 0.3
158 cis-Hexadec-9-enoic acid 1952 – 1.5 0.1
159 Palmitic acid 1958 – 0.3 0.6
160 n-Eicosane 1999 2000 0.1 –
161 Phytol 2119 2620 2.6 0.3
162 Linoleic acid 2143 – 0.2 0.3
163 Methyloctadecanoate 2147 2429 0.2 –
Class composition
Monoterpene hydrocarbons 0.5 0.2
Oxygenated monoterpenes 9.0 1.7
Sesquiterpene hydrocarbons 13.5 34.2
Oxygenated sesquiterpenes 35.4 51.0
Aliphatic hydrocarbons 1.6 1.8
Oxygenated aliphatic hydrocarbons 33.5 6.1
Others 2.8 0.3
Total identified 96.3 95.3
Oil yield (%, w/w-fresh weight basis) 0.06 0.08
⁎ Components are listed in their order of elution from HP-5 MS column; LRIa = determined linear retention index on HP-5 MS column; LRIp = determined linear retention index on DB-wax column; LCL = L. camara leaves oil; LCF = L. camara flowers oil; compounds higher than 5.0% are highlighted with boldface; t = trace (<0.05%).

2.5

2.5 Retention indices

A mixture of a continuous series of straight-chain hydrocarbons, C8–C31 (C8–C20, 04070, Sigma–Aldrich, USA and C20–C31, S23747, AccuStandard, USA) was injected into both polar (DB-Wax) and nonpolar (HP-5MS) columns under the same conditions previously described for the oil samples to obtain the linear retention indices (LRIs) (also referred to as linear temperature programmed retention indices [LTPRI]) of the oil constituents provided in Table 1. The LRIs were computed using van den Dool and Kratz’s equation.

2.6

2.6 Identification of volatile components

GC–FID chromatogram of leaves and flowers essential oils of L. camara with identified peaks of major components on HP-5MS column is shown in Figs. 1 and 2, respectively. The identification of components was done by matching their mass spectra with the library entries (WILEY 9th edition, NIST-08 MS library version 2.0 f as well as the Adams and Flavor libraries) of a mass spectra database as well as by comparing their mass spectra and linear retention indices (LRI) with published data obtained using both polar and nonpolar columns (Acree and Arn, 2015; Adams, 2007; Babushok et al., 2011; Davis, 1990; El-Sayed, 2015; NIST 2015) and the co-injection of authentic standards available in our laboratory.

GC–FID chromatogram of leaves essential oil of Lantana camara on HP-5MS column (peaks: 1: cis-3-hexen-1-ol; 2: 1-hexanol; 3: 1-octen-3-ol; 4: linalool; 5: β-caryophyllene; 6: γ-cadinene; 7: spathulenol; 8: caryophyllene oxide; 9: phytol).
Figure 1
GC–FID chromatogram of leaves essential oil of Lantana camara on HP-5MS column (peaks: 1: cis-3-hexen-1-ol; 2: 1-hexanol; 3: 1-octen-3-ol; 4: linalool; 5: β-caryophyllene; 6: γ-cadinene; 7: spathulenol; 8: caryophyllene oxide; 9: phytol).
GC–FID chromatogram of flowers essential oil of Lantana camara on HP-5MS column (peaks: 1: 1-octen-3-ol; 2: α-copaene; 3: β-caryophyllene; 4: trans-β-farnesene; 5: β-bisabolene; 6: γ-cadinene; 7: spathulenol; 8: caryophyllene oxide; 9: α-cadinol; 10: tetradecanoic acid).
Figure 2
GC–FID chromatogram of flowers essential oil of Lantana camara on HP-5MS column (peaks: 1: 1-octen-3-ol; 2: α-copaene; 3: β-caryophyllene; 4: trans-β-farnesene; 5: β-bisabolene; 6: γ-cadinene; 7: spathulenol; 8: caryophyllene oxide; 9: α-cadinol; 10: tetradecanoic acid).

3

3 Results and discussion

This study describes for the first time detailed characterization of the essential oil constituents derived from leaves and flowers of L. camara growing in Saudi Arabia. The hydro-distillation of L. camara leaves and flowers in a Clevenger-type apparatus afforded light-orange color oils in the yield of 0.06% and 0.08%, w/w, respectively, on the fresh weight basis. The phytochemical analysis of leaves and flowers essential oils of L. camara was performed on gas chromatography–mass spectrometry (GC–MS) and gas chromatography–flame ionization detector (GC–FID) using both polar and nonpolar columns which resulted in the identification of a total of 163 compounds from leaves and flowers oils, in which 98 compounds were found common in both oils and 36 components were specific to leaves oil whereas 29 components were detected only in flowers oil. In the leaves oil of L. camara, 134 compounds were identified, while 127 compounds were identified in the oil obtained from flowers accounting for 96.3% and 95.3% of the total oil compositions, respectively. The identified compounds and their relative contents are listed in Table 1 according to their elution order on a nonpolar HP-5MS column.

Table 1 reveals that the oil from leaves of L. camara was dominated by oxygenated sesquiterpenes (35.4%) followed by oxygenated aliphatic hydrocarbons (33.5%), sesquiterpene hydrocarbons (13.5%) and oxygenated monoterpenes (9.0%). Other classes of compounds such as monoterpene hydrocarbons, aliphatic hydrocarbons and others were not present in appreciable amount and account for only 4.9%. On the other hand, the oil from flowers was dominated by oxygenated sesquiterpenes (51.0%) followed by sesquiterpene hydrocarbons (34.2%) and oxygenated aliphatic hydrocarbons (6.1%). Other chemical classes including monoterpene hydrocarbons, aliphatic hydrocarbons, and oxygenated monoterpenes contributed to only 4.0% (Fig. 3).

Compound classes found in the oils obtained from leaves and flowers of Lantana camara.
Figure 3
Compound classes found in the oils obtained from leaves and flowers of Lantana camara.

The major constituents of leaves oil were cis-3-hexen-1-ol (11.3%), 1-octen-3-ol (8.7%), spathulenol (8.6%), caryophyllene oxide (7.5%) and 1-hexanol (5.8%), while the main compounds of the oil from flowers were caryophyllene oxide (10.6%), β-caryophyllene (9.7%), spathulenol (8.6%), γ-cadinene (5.6%) and trans-β-farnesene (5.0%).

A comparison between leaves and flowers oils of L. camara based on chemical classes reveals that the oxygenated sesquiterpenes and oxygenated aliphatic hydrocarbons were the most prevalent groups in leaves oil, accounting for 68.9% of the total oil compositions, whereas, in the flowers oil oxygenated sesquiterpenes and sesquiterpene hydrocarbons were the most dominating chemical groups, accounting for 85.2% of the total oil compositions. This advocates that both oils contain oxygenated sesquiterpenes as most dominating class of compounds. Nevertheless, the two oils could be easily differentiated from each other considering the amounts of sesquiterpene hydrocarbons and oxygenated aliphatic hydrocarbons. In the flowers oil, content of sesquiterpene hydrocarbons was 2–3 times more than that in the leaves oil, whereas, the content of oxygenated aliphatic hydrocarbons was found to be 5–6 times more in leaves oil than that in flowers oil.

Furthermore, the data presented in Table 1 also suggest that leaves and flowers oil of L. camara showed some important qualitative similarities, since out of 163 components identified from both oils, 98 compounds (73.7% in leaves oil and 87.2% in flowers oil) were found to be common in both oils, although they differed significantly with one another in terms of their relative concentrations. For example, the amount of linalool and phytol was 9–10 folds more in leaves oil than that in the oil from flowers, whereas 1-octen-3-ol, epi-α-muurolol and β-bisabolol were found to be 2–5 folds more in leaves oil. Conversely, the amount of trans-β-farnesene, α-curcumene and α-cadinol was 4–7 times greater in the oil from flowers than in the oil from leaves, while the amount of β-caryophyllene, β-bisabolene, τ-cadinol, tetradecanoic acid and epi-cubebol was 2–3 folds more in flowers oil. Moreover, it is significant to note that two oxygenated aliphatic hydrocarbons, cis-3-hexen-1-ol (11.3%) and 1-hexanol (5.8%) identified in leaves oil as major components were not present in flowers oil of L. camara. Importantly, to the best of our knowledge, these two components, cis-3-hexen-1-ol and 1-hexanol are identified for the first time in Lantana oil. cis-3-Hexen-1-ol, famously known as leaves alcohol widely used in flavors and fragrances industries for imparting fresh green leafy aroma to various products (Vasiliev et al., 2003). It is found in essential oils of many plants but often in low concentration and thus many synthetic procedures have been attempted for the synthesis of this commercially important compound (Moreno-Marrodan et al., 2012). Moreover, cis-3-hexen-1-ol and 1-hexanol have been reported to possess potent inhibitive properties against fusarium diseases (Cruz et al., 2012).

It is noteworthy to mention here that other secondary metabolites particularly, spathulenol, β-caryophyllene and caryophyllene oxide that were identified as major components in the essential oils of present study have been demonstrated to have various important biological activities and industrial applications. For example, spathulenol, an oxygenated sesquiterpene is known for its immunomodulatory and MDR reversal activities (Martins et al., 2010; Ziaei et al., 2011). It is also used as an important ingredient in perfumery, food, pharmaceutical, detergent and cosmetic industries (Leendert et al., 1988), whereas, β-caryophyllene, a bicyclic sesquiterpene with a rare cyclobutane ring and its epoxide derivative caryophyllene oxide have shown numerous important biological activities including neuroprotective, anesthetic, antitumor, immunomodulatory, anti-inflammatory, anticancer, antiviral, anti-mutagenic, anti-proliferative and analgesic activities (Assis et al., 2014; Astani et al., 2011; Chang et al., 2013; Sabulal et al., 2006; Sarpietro et al., 2015). Furthermore, since both compounds possess woody and spicy aroma they are frequently used as flavors and fragrances in various food products and beverages, in soap, lotions, creams, and also in spice blends and citrus flavors and are included in the European list of flavoring substances (Anonymous, 2012; Sabulal et al., 2006; Sarpietro et al., 2015).

Comparison of chemical compositions of leaves and flowers essential oils of L. camara growing in Saudi Arabia with those previously studied from different parts of the world (Filho et al., 2012; Kasali et al., 2004; Khan et al., 2002; Love et al., 2009; Ngassoum et al., 1999; Padalia et al., 2010; Sefidkon, 2002; Sundufu and Shoushan, 2004) revealed that the oil compositions determined in the present study differed significantly from those reported earlier (Table 2). For example, cis-3-hexen-1-ol and 1-hexanol that were determined as major components in the present study have not been detected earlier in any L. camara essential oils analyzed up to now. In contrast, germacrene-D, a natural sesquiterpene hydrocarbon, which has been identified as one of the major components in most of the L. camara oils, was detected in trace amount in the present study.

Table 2 Major components of Lantana camara essential oils reported from various regions of the world.
Geographic regions Major compounds (%) References
Cameroon ar-Curcumene (24.7d), β-caryophyllene (13.3d), caryophyllene epoxide II (7.1d) Ngassoum et al. (1999)
Egypt β-Caryophyllene (15.6a), α-humulene (9.2a), bicyclogermacrene (6.7a), germacrene-D (5.2a), Farnesol (6.4a), spathulenol (6.0a) Elansary et al. (2012)
Nigeria Sabinene (19.6a, 21.5b), 1,8-cineole (14.8a, 12.6b), β-caryophyllene (12.7a, 13.4b), α-humulene (6.3a, 5.8b) Kasali et al. (2004)
South China Germacrene-D (15.9c), β-caryophyllene (12.4c), α-humulene (9.3c), germacrene-B (6.2c) Sundufu and Shoushan (2004)
Iran β-Caryophyllene (25.3d), sabinene (20.2d), bicyclogermacrene (13.3d), α-humulene (8.4d), 1,8-cineole (8.0d) Sefidkon (2002)
Algeria β-Caryophyllene (35.7a), caryophyllene oxide (10.0a), β-elemene (6.4a) Zoubiri and Baaliouamer (2012a)
Cuba E-nerolidol (43.4a), δ-cadinene (7.6a), α-humulene (4.9), β-caryophyllene (4.8a) Pino et al. (2004)
Congo β-Caryophyllene (20.6a), α-humulene (10.6a), bicyclogermacrene (8.6a) Ouamba et al. (2006)
Madagaskar β-Caryophyllene (11.3–13.6e, 25.8–30.8f, 15.9g), davanone (22.6–25.9e, 0.6f, 12.4g), sabinene (9.4–11.3e, 9.0–14.3f, 14.1g), linalool (4.8–6.1e, 0.4–1.4f, 5.4g), α-humulene (4.4–5.2e, 2.4–2.6f, 0.0g) Randrianalijaona et al. (2005)
 Ngaoundere Davanone (15.9d), β-caryophyllene (12.0d), sabinene (9.0d) Ngassoum et al. (1999)
 Antananarivo β-Caryophyllene (18.8d), δ3-carene (9.0d) Mollenbeck et al. (1997)
Brazil β-Caryophyllene (16.2a), germacrene-D (28.6a), bicyclogermacrene (14.7a), germacrene-D-4-ol (19.9a) de Oliveira et al. (2008)
 Crato Bicyclogermacrene (26.1a), β-caryophyllene (19.7a), germacrene-D (19.2a), valencene (12.0a), γ-elemene (5.4a) Sousa et al. (2012)
 Vicosa β-Caryophyllene (24.4a), germacrene-D (19.8a), bicyclogermacrene (11.7a), α-humulene (9.3a) Passos et al. (2012)
India
 Lucknow Germacrene-D (20.5a, 10.6b), β-elemene (7.3a, 14.5b), γ-elemene (10.3a, 6.8b), β-caryophyllene (9.4a, 7.0b), α-copaene (5.0a, 10.0b), α-cadinene (3.3a, 7.2b) Khan et al. (2002)
 Dibrugarh Davanone (47.8a, 7.4b), β-caryophyllene (10.3a, 26.9b), bicyclogermacrene (4.9a, 12.5b), δ-cadinene (2.9a, 7.4b) Misra and Saikia (2011)
 Kumaun Germacrene-D (27.9c), germacrene-B (16.3c), β-caryophyllene (9.6c), α-humulene (5.8c) Padalia et al. (2010)
 Dehradun β-Caryophyllene (23.3a), α-humulene (11.5a), germacrene-D (10.9a), davanone (7.3a) Rana et al. (2005)
a Leaves oil.
b Flowers oil.
c Aerial parts oil.
d Leaves and flowers oil.
e Oil of aerial parts with pink-violet flowers.
f Oil of aerial parts with yellow-orange flowers.
g Industrial oil.

It is significant to mention here that the chemical composition of L. camara essential oils studied until now from different regions of the world has shown prodigious variations (see Table 2). However, it has been noticed that β-caryophyllene, a natural bicyclic sesquiterpene was the only compound that was found either as a major or in appreciable amount in all the L. camara essential oils studied so far. Thus, β-caryophyllene could be used as a chemical marker for the Lantana essential oils.

4

4 Conclusion

L. camara essential oils have shown remarkable variations in their chemical compositions in relation to their place of collection. In the present study, essential oils of L. camara growing in Saudi Arabia have also shown a distinct composition where cis-3-hexen-1-ol and 1-hexanol are major components. To the best of our knowledge, these two components are being reported here for the first time in Lantana oils. Moreover, β-caryophyllene, a natural bicyclic sesquiterpene with a rare cyclobutane ring which has been found in all oils of L. camara studied so far, was also detected as one of the major components in the present study as well, indicating that β-caryophyllene could be used as a chemical marker for the Lantana essential oils. Furthermore, β-caryophyllene and cis-3-hexen-1-ol have wide industrial applications, for example, β-caryophyllene is used in soap, lotions, creams, and also in various food products and beverages, and in spice blends and citrus flavors. On the other hand, cis-3-hexen-1-ol has a great demand in flavors and fragrances industries for imparting fresh green leafy aroma to various products, considering the fact that β-caryophyllene and cis-3-hexen-1-ol are the major components of essential oil of L. camara which is abundantly available in Saudi Arabia and hence, can be used as a cheap and renewable source for industrial isolation of β-caryophyllene and cis-3-hexen-1-ol.

Acknowledgments

This Project was supported by King Saud University, Deanship of Scientific Research, College of Science, Research Center.

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