Essential oil (EO) is a mixture of low molecular weight constituents that are responsible for its characteristic aroma. These constituents include terpenoid and non‐terpenoid hydrocarbons and their oxygenated derivatives. This chapter focuses on the heterogeneous composition of the essential oils. It discusses the usage of essential oil constituents as a key marker of the oil quality, freshness and unique characteristics. It describes the biological activity and synergistic effect of the essential oil constituents as antioxidant, antibacterial, antifungal and anticancer agents.
- chemical structure
- quality characteristics
Essential oil (EO) is defined as odorous product, of complex composition, obtained from part of plant or whole plants through various methods. It has the characteristic taste and odor of the plant from which it was derived [1, 2]. This variation in composition could be due to a variety of plants , geographical locations [3, 4], harvesting seasons [5–7], drying methods  and extraction methods [9, 10].
The quality, freshness and uniqueness of an essential oil are major considerations pertaining to its value . Essential oils are highly sensitive to heat, moisture and oxygen . Formation of oxygenated terpenes, chemical transformations, or polymerization are features of aging processes that led to quality loss. Therefore, quality control of essential oils needs to be monitored by producers, traders, or essential oil manufacturers [13, 14].
Essential oils have wide variety of bioactivities and play an important role as ideal natural sources of antimicrobial, antioxidant and chemopreventive agents [15–17]. They have potential therapeutic applications in the prevention of cancer .
2. Chemical composition of essential oil
Essential oils (EOs) are volatile constituents obtained from aromatic plant material, including leaves, rhizomes, flowers, roots, bark, seeds, peel, fruits, wood and whole plants . A few of the essential oils are found in animal sources, for example, musk and sperm whale, or are produced by microorganisms . In plants, essential oils occur in oil cells, secretory ducts or cavities, or in glandular hairs. Essential oils can be isolated by steam distillation from an aromatic plant because of their volatility . Different constituents in EOs exhibit varying smell or flavor . The perception of individual volatile compounds depends on their threshold .
Essential oils are a complex mixture of polar and non‐polar compounds . The essential oil composition depends on the species of the extracted plant, the geographic location of this plant, harvest time and extraction technique .
Terpenes, related to isoprene
Straight‐chain compounds not containing any side chain
Phenylpropanoids (benzene derivatives)
Miscellaneous group having varied structures not included in first three groups (sulfur‐ or nitrogen‐containing compounds)
2.1. Terpenes, related to isoprene or isopentene
Essential oils constituents can be divided into two major groups: terpene hydrocarbons and oxygenated compounds .
2.1.1. Terpene hydrocarbons
Terpenes are the most common class of chemical compounds found in essential oils . Terpenes are synthesized in the cytoplasm of plant cells, through the mevalonic acid pathway . Terpenes have been regarded as polymers of isoprene (C5H8) joined in a repetitive head‐to‐tail manner  as shown in Figure 1.
They could be classified according to the fusion of the isoprene units or to the number of the rings . Terpenes can be classified into hemiterpenes (1 unit), monoterpenes (2 units), sesquiterpenes (3 units), diterpenes (4 units), sesterterpenes (5 units), triterpenes (6 units) and polyterpenes (many units) . The combinations of two isoprene units are called a “terpene unit.” Monoterpenes (C10H16) are formed by the attachment of two isoprene units (at least one double bond). These terpenes have a hydrocarbon skeleton which can be rearranged into acyclic, cyclic, or aromatic (Figure 2). Cyclic monoterpenes can be classified according to their ring size such as monocyclic monoterpenes, bicyclic monoterpenes and tricyclic monoterpenes  Figure 3. These compounds oxidize easily because of their rapid reaction to air and heat sources .
Sesquiterpenes (C15H24) are the second to the dominant monoterpenes. They are formed from the combination of three isoprene units . Sesquiterpenes are unsaturated compounds. There are linear, branched, or cyclic sesquiterpenes (Figure 4). Sesquiterpenes are unsaturated compounds. Cyclic sesquiterpenes can be classified into monocyclic, bicyclic, or tricyclic  (Figure 5). Diterpenes are formed by the head‐to‐tail combinations of four isoprene units followed by rearrangement and/or substitutions (Figure 6).
They are important components of plant resins . Diterpenes, triterpenes and tetraterpenes are present at a very low concentration in essential oils [27, 34]. Their recovery increases with increasing steam distillation times  and influenced by the extraction method.
2.1.2. Oxygenated compounds (terpenoids)
The oxygenated compounds are highly odoriferous . Terpenoids are volatile secondary metabolites which give plants their fragrance . Terpenoids can be subdivided into aldehydes, ethers, alcohols, esters, ketones, phenols and epoxides . Examples: (+)‐Borneol occurs in camphor, rosemary and lavender oils. It has a camphor‐like odor, with a slightly peppery note . Carvacrol is found in oregano and thyme  oils. It has a herbaceous, phenolic odor . (-)‐Carvone has a herbal scent and is found in caraway seed oil; (+)‐carvone with a spicy‐minty odor can be found in spearmint oil . 1,8‐Cineole is obtained primarily by isolation from eucalyptus oil. It has a camphor odor .
2.2. Straight‐chain compounds, not containing any side branches
This group contains only straight chain non‐terpenoid hydrocarbons and their oxygen derivatives: alcohols, aldehydes, ketones, acids, ethers and esters. These hydrocarbons range from n‐heptane, to compounds with 35 carbon atoms. Heptane content represented 3.8 and 36.8% of the wood volatile oils of
2.3. Phenylpropenes (benzene derivatives)
These aromatic compounds are an important group to flavor and fragrance industry though it constitutes a relatively small part of the essential oils. This non‐terpenoid group comprises of constituents derived from n‐propyl benzene. The aromatic ring may carry hydroxy, methoxy and methylene dioxy groups; the propyl side chain may contain hydroxyl or carboxyl group .
Phenylpropenes constitute a subfamily of phenylpropanoids that are synthesized from the amino acid phenylalanine and l‐tyrosine via the shikimic acid pathway . Examples of this group include trans‐anethole, methyl chavicol, eugenol, isoeugenol, vanillin, safrole, myristicin and cinnamaldehyde [19, 47] (Figure 8).
2.4. Miscellaneous group (sulfur‐ and nitrogen‐containing compounds)
The representatives of this group are the compounds, which are not included in the above mentioned three groups . They are different degradation products originating from unsaturated fatty acids, lactones, terpenes, glycosides and sulfur‐ and nitrogen‐containing compounds .
Sulfur‐ and nitrogen‐containing compounds occur mainly as aglycones or glucosinolates, or their breakdown products, which include isothiocyanates . The Brassicaceae is an important source of glucosinolates and isothiocyanates . Garlic, onion, leek and shallots contain volatile sulfur compounds, namely allyl sulfide, dimethyl sulfide, diallyl disulfide and dimethylthiophene . The sulfur compounds are responsible for the characteristic aroma and taste . Cysteine sulfoxides including alliin predominate in mature, intact Allium spp., along with γ‐glutamylcysteines . Upon rupture, such as when chopped or pressed, the action of a class of enzymes known as alliinases catalyzes the conversion of cysteine sulfoxides into the volatile thiosulfinates  including allicin. Allicin makes up 70–80% of the thiosulfinates. Allicin and other thiosulfinates decompose diallyl sulfide, diallyl disulfide, diallyl trisulfide, dithiins and ajoene, while the γ‐glutamylcysteines are converted to S‐allyl cysteine through a non‐alliin/allicin pathway . Nitrogen‐containing compounds are found in only a few essential oils. Examples include methyl anthranilate, indole, pyridine and pyrazine. Methyl anthranilate is present in orange, lemon and bergamot oils  and jasmine oil . Indole occurs in neroli and some citrus fruit oils . Pyridines and pyrazines occur in black pepper, sweet orange and vetiver oils  (Figure 9).
3. Quality indices of essential oils
The studies have shown that a differentiation in oil quality and volatile components is associated with climatic conditions, geographical location of collection sites and other ecological and genetic factors. The influence of those factors on the accumulation of distinct volatile compounds defines its chemotypes [56–58].
3.1. Black pepper oil
Black pepper oil is obtained from the dried unripe fruits of
Storage of black pepper hammer milled powder for 6 months at 4°C, markedly increased monoterpene to sesquiterpene hydrocarbons ratio from 1.31 to 4.47. They attributed this increase to the degradation of some sesquiterpenes, as a result of oxidative decomposition during storage .
3.2. Cardamom oil
Cardamom oil is obtained from the dried ripe fruits of
Monoterpenes hydrocarbons are less odoriferous than oxygenated monoterpenes . Amma et al.  recorded superior flavor quality for the Malabar variety with the highest α‐terpinyl acetate/1,8‐cineole ratio (1.55) when compared with the Mysore variety (1.34). Morsy  found that this ratio exceeded 1.6 when ultrasound‐assisted extraction (30 W, for 30 min) was used as a pretreatment for hydrodistillation (30 min) compared to 1.13 when hydrodistillation was conducted for 6 h. The presence of a low level of hydrocarbons in cardamom oil could be used as an indicator of its high quality .
3.3. Caraway essential oil
Caraway oil is obtained from the dried ripe fruits of
3.4. Peppermint oil
3.5. Lavender oil
Lavender flowers (
3.6. Rose oil
Citronellol/geraniol (C/G) ratio could be used for evaluating the quality of rose oil . The finest quality rose oil has C/G ratio between 1.25 and 1.30 . In the rose oil trade, the citronellol content should be higher than 35%. The oils from non‐fermented petals generally contain citronellol lower than this level. Therefore, a short‐term fermentation is conducted to increase the citronellol content. The C/G ratios were higher in the oils distilled from long‐term fermented petals (e.g., 10.3 in 36 h fermentation) than non‐fermented petals (0.56). Based on these results, rose oils distilled from long‐term fermented petals are of poor quality .
3.7. Ginger oil
Ginger oil is obtained from the rhizomes of
The lemony note is attributed to citral together with α‐terpineol, while nerolidol is responsible for the woody note. β‐Sesquiphellandrene and ar‐curcumene contribute to the characteristic ginger flavor .
3.8. Juniper oil
Butkienë et al.  identified 143 components in the juniper leaves essential oil. They found that monoterpenes (M)/sesquiterpenes (S) ratio ranged from 2:1 to 5:1 according to localities in Vilnius district, Lithuania. Sela et al.  found that M/S ratio ranged from 1:1 to 3:1 for leaves essential oil of Macedonian juniper, from different localities. Orav et al.  reported that M/S ratio of juniper berries oils was higher (4:1) than that obtained from leaves samples (2.5:1). Pourmortazavi et al.  found that supercritical fluid extraction products from
3.9. Oregano, thyme and savory oils
Oregano, wild marjoram,
In oregano essential oil, the total content of the thymol and carvacrol was the highest and amounted to 67.51%; in thyme essential oil, 47.47%; and in savory essential oil, 49.71%. The thymol and carvacrol types have sharp, warm and penetrating herbal (thyme type) odors, with woody, spicy and tobacco‐like notes; thymol itself has a powerful, medicated and herbaceous odor while carvacrol itself has a tar‐like odor . The ratio of carvacrol to thymol in oregano, thyme and savory essential oils was 15:1, 1:19 and 1.8:1, respectively . Oils containing predominantly thymol are generally considered of superior quality [112, 113].
3.10. Lemongrass oil
4. Bioactivities of essential oil constituents
Essential oils from different plant parts exhibit different biological activities . Biological activities of essential oils include antioxidant, antimicrobial, antiviral, anti‐mutagenic and anticancer . Essential oils are complex mixtures of terpenoids and phenylpropanoids compounds extracted by distillation or solvent extraction . Overall activity cannot be attributed to only one of the major constituents . The inactive compounds might influence resorption, the rate of reactions and biological activity of the active compounds. The combination of the major and minor constituents modifies the activity to exert significant synergistic or antagonistic effect .
4.1. Antioxidant activity
Antioxidants are substances that protect cells from being oxidized by free radicals. Reactive oxygen species (ROS) are highly reactive toxic molecules. ROS induced oxidative diseases such as ageing, arteriosclerosis, cancer, Alzheimer's disease and Parkinson's disease . Living cells possess scavenging activity to diminish excess ROS that induced cellular injury. These mechanisms become inefficient, with ageing and under external stress. Therefore, dietary supplementation of natural and synthetic antioxidants is required . Some synthetic antioxidants cause liver damage and have carcinogenic effects. Natural antioxidants are preferred to synthetic ones .
The essential oil of lemon balm, containing neral/citral, citronellal, menthone and isomenthone, showed strong antioxidant activity .
The essential oils with good radical‐scavenging activity could be arranged in the following order, clove > cinnamon > nutmeg > basil > oregano > thyme .
Misharina and Samusenko  stored a mixture of lemon, coriander and clove buds essential oils (1:1:1) at room temperature in the light for 145 days. They found that the mixture of the three essential oils increased the stability of limonene and γ‐terpinene significantly higher than in the individual essential oils and inhibited oxidation of hexanal efficiently. It was shown that terpene hydrocarbons break free‐radical chain reactions, which is accompanied by their irreversible oxidation into inert compounds, such as
Wei and Shibamoto  proposed that terpenes and terpenoids that contribute to the antioxidant activity of essential oils include
Eugenol, the major constituent of clove essential oil, was found to have an inhibitory activity against lipid peroxidation by interfering with chain reactions of free radicals. The inhibitory activity of eugenol was about fivefold higher than that observed for alpha‐tocopherol . Thymol and carvacrol the main constituents of thyme oil are shown to act as strong antioxidants . The antioxidant activity of caraway oil may be due to the presence of linalool, carvacrol, anethole and estragole . Marjoram and clove essential oils exerted a powerful antioxidant activity in beef burger prepared with sunflower oil during storage at -18°C for 3 months. The addition of marjoram oil at 250 mg/kg kept thiobarbituric acid value of the beef burger samples after 3 months of storage at a level not significantly different from that of control samples stored frozen for 1 month . Flavoring refined corn oil with thyme increased its oxidative stability (induction time) from 4.36 to 6.48 h . Blending cold‐pressed oregano (
4.2. Antibacterial activity
Essential oils display broad‐spectrum inhibitory activities against various bacterial pathogens . Essential oil is easily permeable through the cell wall and cell membrane due to its lipophilic characteristic. Interaction of essential oil components with polysaccharides, fatty acids and phospholipids causes loss of membrane integrity, leakage of the cellular contents, interference in proton pump activity and leads to cell death [124, 138–140]. Other important mechanisms of action include denaturation of cellular proteins [9, 34, 141]. Carvone partitioned in the lipid membrane , while terpinen‐4‐ol inhibits cellular respiration and both damage cell membrane function as a permeable barrier . Carvacrol and
Sage essential oil is rich in antimicrobial agents . The single layer wall of
4.3. Antifungal activity
Fungi are important causes of human infections . Several crops are susceptible to fungal attack either in the field or during storage . Fungicide residues are problems for the food industry . Prevention of fungal growth is an effective way of impeding mycotoxin accumulation . Essential oils have the ability to attack the life cycle of molds .
The high cost of essential oils production and the low concentration of active constituents limit their direct use in the control of fungal diseases of plants and animals. Therefore, investigation of antifungal compounds of the essential oils is considered important because of the possibility of synthesizing these compounds for the use in the control of fungal diseases .
Bouchra et al.  reported that the major essential oils constituents of Moroccan Labiatae
Serrano et al.  reduced the growth of yeasts and molds for stored cherries by developing active packaging materials containing eugenol, menthol, thymol and eucalyptol.
The essential oil of cinnamon had a high antifungal effect (very low minimum inhibitory concentration) against
Carvacrol, the major active ingredient, of oregano oil was found to cause complete inhibition of
Sourmaghi et al.  found that hydrodistilled coriander essential oil had a potent antifungal activity against
Rahman et al.  reported that the hydrodistilled essential oil of the leaves of
de Oliveira et al.  found that the essential oil of
4.4. Anticancer activity
Cancer is a multifactorial disease contributing towards the uncontrolled growth of the abnormal cells, leading to the formation of a tumor . Carcinogenesis is a multistep process and oxidative damage that is linked to the formation of tumors. Secondary metabolites from different plants are capable of halting development of cancer . Essential oil constituents have cytotoxic and antitumor activities. They play an important role in cancer prevention and treatment [18, 167]. Essential oils can be used in combination with cancer therapy to decrease the side effects of the drugs . Cytotoxicity of essential oils is due to its action upon cellular integrity, leading to necrosis and apoptosis, cell cycle arrest and loss of key organelles function [169, 170]. Therefore, the evaluation of the anticancer activity of essential oils and their safety on normal cell lines are of great importance .
The essential oil of
Terpenoids of essential oils prevent tumor cell proliferation . Linalool and linalyl acetate represented the major constituents in lavender essential oil. They were more cytotoxic than the whole essential oil against 153BR, HNDF and HMEC‐1 cancer cell lines . Geraniol suppressed the growth of MCF‐7 breast cancer cells  and PC‐3 prostate cancer cells . It was reported to interfere with membrane functions, ion homeostasis; inhibit DNA synthesis; and reduce the size of colon tumors . β‐Caryophyllene did not inhibit cell growth of MCF‐7 breast cancer cell lines, but α‐humulene was cytotoxic. However, β‐caryophyllene potentiated the cytotoxicity of α‐humulene . Limonene and linalyl acetate had no effect on neuroblastoma cells. However, their combination induced apoptosis . This synergic effect was consistent in several studies for antitumor properties .
Carvacrol is a major component of oregano and thyme essential oils. It inhibits tumor cell proliferation and induces apoptosis in human colon cancer cell lines, HCT116 and LoVo  and in human oral squamous cell carcinoma . Perillyl alcohol decreases the growth of HCT116 cells .
The essential oils are multi‐component systems, while their key components represent single component systems. Quality assurance of essential oils is imperative to ensure authenticity and product quality. The ratio of one special component or group of components to another is one of the quality indices of an essential oil as it affects its aroma.
Some of the essential oil constituents contribute to the essential oil antioxidant, antimicrobial and anticancer activities, regardless their concentration. They contribute by their synergistic effect to the property of the essential oil.
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