**3. Description of coriander**

Essential oil or essence is referred to by this name due to their flammable principle. In many kinds of the literature, the essential oils have been defined [2]. Briefly, essential oils are secondary metabolites biosynthesized in different plant organs [3] obtained by mainly hydrodistillation from almost all parts of the aromatic plants growing temperate regions in the world, of the secretory special elements with volatile properties along with characteristic fragrances, as limpid and rarely colored, soluble, in organic solvents [4]. The chemical composition of the essential oils is quite complex including mostly terpenes (monoterpenes and partly sesquiterpenes formed by isoprene) and aromatic compounds derived from phenylpropane and phenolic constituents [3, 5]. The essential oils known as fragrant oils, steam volatile liquids, or semiliquids, ethereal oils are concentrated hydrophobic aromatic oil. The flavor (fragrance and flavor) of the essential oils is marvelous due to reflecting their corresponding sources as mean basically plant [3]. The physiological effects of the essential oils are not clear but can say that protect the plants against microorganisms, insects, or attract them for the pollination [5]. The conventional methods to obtain the essential oils are hydrodistillation, steam distillation, solvent extraction, Soxhlet extraction, cold pressing method, enfleurage, cohobation, and maceration. By the way, distillation is absolutely the most common method of obtaining essential oils. In addition, innovative techniques can be covered supercritical fluid extraction (SFE), microwave-assisted hydrodistillation (MAHD), ultrasound-assisted extraction (UAE), solvent-free microwave extraction (SFME) and microwave hydro diffusion and gravity (MHG) [3]. Analytical monographs have been published by European Pharmacopeia (EP), International Organization of Standardization (ISO), World Health Organization (WHO), Council of Europe (COE) to ensure good quality of essential oils. The essential oils are exhibited in many important biological activities [1–5] and discussed in many kinds of the literature but mainly antibacterial and antifungal activities are dominated [6]. Essential oils are also commercially important, especially in the pharmaceutical, agronomic, food, sanitary, and cosmetic and perfume industries. Moreover, essential oils are the main therapeutic agent in aromatherapy as it forms mixtures with vegetal oil in several forms [3, 7, 8]. Essential oils are classified as "Generally Recognized as Safe" (GRAS) by the Food and Drugs Administration (FDA); therefore, they are not counted as harmful and, due to their natural origin, are more widely endorsed by consumers than "synthetic" agents [6], if it is used reasonably and carefully. In fact, there are so many things to say regarding essential oils, but this section will be interested in coriander as aromatic plant and its essential oil. Hence, in this chapter, we discuss the essential oil of coriander, which is very important in many fields called as food, spice, cosmetic, and of course pharmaceutical. Therefore, you can find much information regarding coriander, which has great importance almost in every field. Consequently, the coriander will

be handled with the latest articles in details according to an order.

The phytochemical constituents and pharmacological activities regarding the coriander and its essential oil have been investigated with the help of PubMed, Science Direct, Scopus, and Google. Generally, the latest articles were used when writing this review in this process.

**2. Methodology**

166 Potential of Essential Oils

*Coriandrum sativum* L. (Coriander) is a member of the Apiaceae family (previously Umbelliferae) [9, 10] and known as cilantro, cilantrillo, Arab parsley, Chinese parsley, Mexican parsley, Dhania, and Yuen sai. It is an annual herb commonly used in Middle Eastern, Mediterranean, Indian, Latin American, African, and Southeast Asian cuisine [11]. Although cilantro and coriander seem to describe the same thing, it actually carries different meanings. When the plant is freshly harvested, the green leaves of the plant is called cilantro; if the dried fruits are used, the herb is called as coriander [12].

**Figure 1.** Coriander (The leaves and flowers from nature). Photo: M. Necat IZGI.

The plant grows all over the world [13], but originally from the Mediterranean regions, cultivated mainly in the tropical areas such as Ukraine, Russia, Romania, Morocco, Mexico, India, and Argentina [14]. Especially in a cool and comparatively dry frost, the free climate at the optimum temperature of germination and early growth of coriander is 20-25 °C. It grows best in dry climates, but it can grow in any type of soil like light, well-drained, moist, loamy soil, and light to the heavy black soil [15].

The genus Coriandrum L. (**Figure 1**) has been represented by two species in Flora of Turkey called C. sativum L. and C. tordylium (Fenzl) Bornm. [10]. C. sativum L. is coriander, approximately 30–100 cm in height, with strong-smelling leaves. It is cultivated as a domestic plant. In addition, in commerce, coriander has two varieties such as C. sativum L. var. microcarpum DC, the small-fruited species called as oil-rich Russian coriander and C. sativum L. var. vulgare Alef., the larger-fruited species with low oil content called as Moroccan, Indian and some other Asiatic types [16, 17]. The coriander has been described as glabrous aromatic, herbaceous, erect annual plant with a pronounced taproot, and slender branching stems up to 20–70 cm in height. The leaves are lanceolate, green or dark green, glabrous on both surfaces and are variable in shape and lobed. The flowers are arisen in small umbels, white or light pink, asymmetrical, with the petals pointing away from the center. The coriander fruits are almost ovate globular dry schizocarp with two mericarps as usual and multiple longitudinal ridges on the surface possessing a sweet, slightly pungent, citrus-like flavor resembling sage [10, 17].

The fruits contain sugars, alkaloids, flavones, resins, tannins, anthraquinones, sterols, and fixed oils [21, 22]. We can say that the most important constituents of coriander fruits are the essential oil and fatty oil [23]. The fatty acids in coriander fruits are petroselinic acid (*cis*-6-octadecenoic acid, 18:1), linoleic acid (18:2), oleic acid (18:1), and palmitic acid (16:0) [16, 17]. It was reported that coriander like all other green leafy vegetables is a rich source of vitamins (high amount of vitamin A/β-carotene: 12 mg/100 g and vitamin C: 160 mg/100 g) besides minerals and iron [24], very low in saturated fat and cholesterol and a very good source of thiamine, zinc, and dietary fiber. Unripen coriander contains 84% water [15]. Here, the most

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There is much work to be performed collected from different localities of coriander essential oil. Because of the fact that, the coriander is one of the most important essential oil-bearing spices in its leaves, flowers, stem, seeds, roots, and bark; however, the composition of the parts can be different. Its chemical composition undergoes changes during ontogenesis, which affects the aroma of the plant, and thus interestingly the coriander fruit (seed) aroma is completely different from the aroma of the herb. Immature fruits and leaves have an unpleasant odor called a "stink bug smell" which is due to the presence of trans-tridecen in the oil [17]. On the other hand, the fragrance in the mature fruits pleasantly is similar to citrus peel and sage [16, 17]. By the way, Burdock et al. have mentioned about specifications of coriander

Coriander fruits contain about 0.2–1.5% of essential oil and 13–20% of vegetal oil (fixed oil); however, it has been recorded that some cultivars contain essential oil up to 2.6% [15, 25]. Another literature mentioned that coriander contains up to 1% essential oil where monoterpenoid linalool is the major compound (>50%), and limonene, camphor, and geraniol (**Figure 2**) are present in significant quantity [26]. Sometimes, the essential oil of the coriander obtained from the fruits was recorded approximately as 0.5–2.5%. It seems that different cultivars and

important phytoconstituents will be mentioned in the order.

oil according to the Food Chemical Codex (FCC) as given below [19]:

Solubility in alcohol Passes test. 1 ml dissolves in 3 ml of 70% alcohol

**5.1. Essential oils**

**Characteristics Metrics**

Heavy metals (as Pb) Passes test

FCC = Food Chemicals Codex.

Angular rotation Between +8 and +15

Appearance Colorless or pale yellow liquid

Identification Infrared absorption spectrum Odor Characteristic of coriander

Specific gravity Between 0.863 and 0.875

Coriander oil specifications according to the FCC, 2003 [19].

Refractive index Between 1.462 and 1.472 at 20°C

#### **4. History of coriander**

*Coriandrum sativum* L. has a long history as a culinary herb [17]. Sanskrit literature before 5000 BC and Greek Ebers Papyrus earlier 1550 BC have been mentioned from this herb. The coriander name comes from the "korannon," which is derived from the words "koris" and "annon" in Greece. By the way, the genus name as *"*Coriandrum" the first used by Pliny the Elder [18, 19]. It was said that the coriander seed emerged in the Neolithic level of the Nahal Hemel Cave in Israel. On the other hand, interestingly about one-half liter of coriander seeds was found in the tomb of Tutankhamun (Ramesses II) in Egypt. In Egypt, the herb was known as "spice of the happiness" may be attributed to its aphrodisiac property. In Greece, coriander seems to have been cultivated, since at least the second millennium BC, where the plant was used in perfumes and in cooking besides used as traditional medicine by Hippocrates [12, 19]. The herb was also widely used in the Roman Empire. As an example, Apicius (a collection of Roman cookery recipes) includes some 70 recipes using coriander in his cookbook. In Germany, coriander was used about ~900 AD [12]. The first factory to obtain the essential oil of coriander by the steam distillation was built in Russia in 1885 in the Voronezˇ district [20]. I came across a section regarding coriander written by Dioscorides in the literature. As shown below, Dioscorides emphasized how important it is [12]:

Dioscorides\* wrote about *Coriandrum sativum*.

\*Source: Beck LY, transl. Pedianius Dioscorides of Anazarbus. In: The Materia.

Medica: Ancient Scientific Texts and Studies, vol. 38 [in German]. Hildesheim,

Germany: Olms-Weismann.

#### **5. Phytochemical constituents of coriander**

*Coriandrum sativum* L. is a medicinal plant native to the eastern Mediterranean where it may have spread like many other aromatic plants to India, China and rest of the world [17]. In this frame, the essential oil is the main secondary metabolite of coriander. However, a different group of active substances will also be mentioned in present compilation.

III. 63. κοριον The coriander: it has a cooling property, wherefore when plastered on with bread or barley groats, it cures erysipelas and shingles; with honey and raisins, it treats pustules that are most painful at night, testicular inflammations, and carbuncles; and with bruised corn, it dissolves scrofulous swellings of the glands and tumors. A small quantity of its seed drunk with grape syrup expels intestinal worms and furthers the production of semen, but if too much is taken, it dangerously disturbs the thinking process; this is why one must guard against drinking it to excess and continuously. Anointed with white lead or with litharge, and with vinegar and unguent of roses, the juice benefits surface tumors that are inflamed.

The fruits contain sugars, alkaloids, flavones, resins, tannins, anthraquinones, sterols, and fixed oils [21, 22]. We can say that the most important constituents of coriander fruits are the essential oil and fatty oil [23]. The fatty acids in coriander fruits are petroselinic acid (*cis*-6-octadecenoic acid, 18:1), linoleic acid (18:2), oleic acid (18:1), and palmitic acid (16:0) [16, 17]. It was reported that coriander like all other green leafy vegetables is a rich source of vitamins (high amount of vitamin A/β-carotene: 12 mg/100 g and vitamin C: 160 mg/100 g) besides minerals and iron [24], very low in saturated fat and cholesterol and a very good source of thiamine, zinc, and dietary fiber. Unripen coriander contains 84% water [15]. Here, the most important phytoconstituents will be mentioned in the order.

#### **5.1. Essential oils**

in height. The leaves are lanceolate, green or dark green, glabrous on both surfaces and are variable in shape and lobed. The flowers are arisen in small umbels, white or light pink, asymmetrical, with the petals pointing away from the center. The coriander fruits are almost ovate globular dry schizocarp with two mericarps as usual and multiple longitudinal ridges on the surface possessing a sweet, slightly pungent, citrus-like flavor resembling sage [10, 17].

*Coriandrum sativum* L. has a long history as a culinary herb [17]. Sanskrit literature before 5000 BC and Greek Ebers Papyrus earlier 1550 BC have been mentioned from this herb. The coriander name comes from the "korannon," which is derived from the words "koris" and "annon" in Greece. By the way, the genus name as *"*Coriandrum" the first used by Pliny the Elder [18, 19]. It was said that the coriander seed emerged in the Neolithic level of the Nahal Hemel Cave in Israel. On the other hand, interestingly about one-half liter of coriander seeds was found in the tomb of Tutankhamun (Ramesses II) in Egypt. In Egypt, the herb was known as "spice of the happiness" may be attributed to its aphrodisiac property. In Greece, coriander seems to have been cultivated, since at least the second millennium BC, where the plant was used in perfumes and in cooking besides used as traditional medicine by Hippocrates [12, 19]. The herb was also widely used in the Roman Empire. As an example, Apicius (a collection of Roman cookery recipes) includes some 70 recipes using coriander in his cookbook. In Germany, coriander was used about ~900 AD [12]. The first factory to obtain the essential oil of coriander by the steam distillation was built in Russia in 1885 in the Voronezˇ district [20]. I came across a section regarding coriander written by Dioscorides in the literature. As shown below,

*Coriandrum sativum* L. is a medicinal plant native to the eastern Mediterranean where it may have spread like many other aromatic plants to India, China and rest of the world [17]. In this frame, the essential oil is the main secondary metabolite of coriander. However, a different

III. 63. κοριον The coriander: it has a cooling property, wherefore when plastered on with bread or barley groats, it cures erysipelas and shingles; with honey and raisins, it treats pustules that are most painful at night, testicular inflammations, and carbuncles; and with bruised corn, it dissolves scrofulous swellings of the glands and tumors. A small quantity of its seed drunk with grape syrup expels intestinal worms and furthers the production of semen, but if too much is taken, it dangerously disturbs the thinking process; this is why one must guard against drinking it to excess and continuously. Anointed with white lead or with litharge, and with vinegar and unguent of roses, the

group of active substances will also be mentioned in present compilation.

**4. History of coriander**

168 Potential of Essential Oils

Dioscorides emphasized how important it is [12]:

Dioscorides\* wrote about *Coriandrum sativum*.

juice benefits surface tumors that are inflamed.

Germany: Olms-Weismann.

**5. Phytochemical constituents of coriander**

\*Source: Beck LY, transl. Pedianius Dioscorides of Anazarbus. In: The Materia. Medica: Ancient Scientific Texts and Studies, vol. 38 [in German]. Hildesheim, There is much work to be performed collected from different localities of coriander essential oil. Because of the fact that, the coriander is one of the most important essential oil-bearing spices in its leaves, flowers, stem, seeds, roots, and bark; however, the composition of the parts can be different. Its chemical composition undergoes changes during ontogenesis, which affects the aroma of the plant, and thus interestingly the coriander fruit (seed) aroma is completely different from the aroma of the herb. Immature fruits and leaves have an unpleasant odor called a "stink bug smell" which is due to the presence of trans-tridecen in the oil [17]. On the other hand, the fragrance in the mature fruits pleasantly is similar to citrus peel and sage [16, 17]. By the way, Burdock et al. have mentioned about specifications of coriander oil according to the Food Chemical Codex (FCC) as given below [19]:


Coriander fruits contain about 0.2–1.5% of essential oil and 13–20% of vegetal oil (fixed oil); however, it has been recorded that some cultivars contain essential oil up to 2.6% [15, 25]. Another literature mentioned that coriander contains up to 1% essential oil where monoterpenoid linalool is the major compound (>50%), and limonene, camphor, and geraniol (**Figure 2**) are present in significant quantity [26]. Sometimes, the essential oil of the coriander obtained from the fruits was recorded approximately as 0.5–2.5%. It seems that different cultivars and

subcritical water extraction on 100°C provided the lowest yield of lipid extract (0.36%). Similarly, the major compounds from coriander oil [γ-terpinene, (+)-limonene, linalool, camphor, and geraniol] were obtained by Soxhlet extraction (785.05, 26.73 and 21.96 mg/100 g of coriander fruits, respectively). By the way, subcritical fluid extraction provided extraction of vegetal oil, while polyphenolics were also extracted by subcritical water extraction, increasing health value of obtained extracts, and presenting good alternatives for traditional techniques [26]. Although the examples given are reproduced, the volatile oil content and their rates are almost the same.

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The vegetal oil (fixed oil/fatty oil) of coriander fruits, especially from French origin (23% yield), contain a high amount of monounsaturated fatty acids (1.8%); particularly petroselinic acid (73%) [22, 26]. The vegetable oil of coriander has been labeled as a Novel Food Ingredient (NFI), and it can be safely consumed as a food supplement by healthy persons, in maximum 600 mg/day dosages [22]. That is why, the essential oil of *C. sativum* fruits is called as triglyceride oil, due to the presence of petroselinic acid (**Figure 3**). The plant is recognized a potential source of lipids (rich in petroselinic acid) and essential oil (high in linalool) isolated from the fruits and the aerial parts [17]. The presence of petroselinic acid makes coriander more precious and interesting.

Petroselinic acid (18,1n-12) is classified as a monounsaturated the major omega-12 fatty acid exists in coriander oil, is a positional isomer of octadecenoic acid (its double bond being in position 6 instead of 9). Petroselinic acid has been detected at a level between 68 and 83% in coriander oil [31], or between 65–70% and 80.9% [9]. In a study, changes in fatty acids during maturation of coriander fruits cultivated in the North-East of Tunisia (Charfine) were studied. At full maturity, the main fatty acids were petroselinic acid (80.9 ± 5.7%), followed by linoleic (13.6 ± 2.9%), palmitic (3.6 ± 0.1%), and stearic (0.7 ± 0.1%) acids. During maturation of coriander fruit, saturated and polyunsaturated fatty acids decrease significantly, and monounsaturated fatty acids increase. It is necessary to underline that coriander fruits at the first four stages of maturity have a healthy nutritional value and the last five stages were with important economic and industrial applications [32, 33]. Commercial production of vegetable oils from oil-rich materials is based on through two traditional processes like the mechanical expression and extraction. In this manner, the maximum yield was obtained with single screw extruder for a configuration allowing the strongest oil expression. Comparing with a mechanical press, the maximum yield was obtained by the Soxhlet extraction with 21.25%, and the oil quality was found high grade. The acid value was under 1.8 mg of KOH/g of oil and iodine values were tolerable (44 mg of iodine/100 g of oil). In the oil, nine fatty acids were identified, with petroselinic acid accounting for 74–77% of the total fatty acids, followed by linoleic (12–13%), oleic (4–6%), and palmitic acids (3%). Moreover, *β-*sitosterol was the major sterol (28%) in all oils. The next major sterols in all oils were stigmasterol (24–27% of total


**5.2. Fatty acids**

sterols) and Δ<sup>7</sup>

**Figure 3.** The structure of petroselinic acid.

**Figure 2.** The major constituents in the essential oil of coriander fruit: (a) linalool, (b) limonene, (c) camphor, and (d) geraniol.

regions have been present in a different ratio of the essential oil concentration. However, in the majority of studies the main component is defined as linalool (60-70%) [16, 17]; sometimes up to 87.54%. In addition, α-pinene, camphor and geraniol are also known as other important components and are responsible for the character of fragrance and aroma of the plant. The investigation on two coriander varieties (*vulgare* and *microcarpum*) from Turkey has resulted in oil content like 0.15–0.25% in *vulgare* (linalool 42.1–52.7%); and 0.31–0.43% in *microcarpum* (linalool 63.5–71.0%) [9]. In Iran, the essential oil from the dried fruit of the coriander has been found in the range of 0.1–0.36% represented by 34 compounds, linalool (40.9–79.9%) as major component [27].

In a study, the essential oil of coriander was obtained by supercritical water extraction, hydrodistillation, and Soxhlet extraction methods. The main component found was linalool (82.916%) chosen as the key component to find the best-operating conditions [20]. In fact, the parameters exhibit different impact to reach the volatile oil; pressure and temperature control influenced the yield and composition. In an example, supercritical CO<sup>2</sup> fluid extraction to obtain the volatile oil from Italian coriander fruits was performed under different temperature conditions. A decrease in the particle size improved the volatiles' yield so as to more ducts were destroyed during the milling process. Optimum supercritical fluid extraction conditions were found to be as follows: Pressure 90 bar, temperature 40°C, 1.10 kg/h and 0.6 mm. The compositions of each supercritical fluid extraction samples were analyzed by GC and GC/MS. The major components were linalool (65–79%), the others γ-terpinene (4–7%), camphor (3%), geranyl acetate (2–4%), *α*-pinene (1–3%), geraniol (1–3%) and limonene (1–2%) [28]. Linalool was determined as the highest percentage composition in the essential oil of *C. sativum* fruit (73.11%) [29], but this rate can vary during different maturation periods. Essential oil obtained by hydrodistillation increased markedly during the maturation process, and geranyl acetate (46.27%), linalool (10.96%), nerol (1.53%) and neral (1.42%) were the major compounds at the first stage of immature fruits. At the middle stage, linalool (76.33%), *cis*-dihydrocarvone (3.21%) and geranyl acetate (2.85%) were reported as the main constituents. Essential oils at the final stage of maturity (mature fruits) include mainly of linalool (87.54%) and *cis*-dihydrocarvone (2.36%) [30]. In another study, the volatile oils of coriander have been compared each other by conventional methods such as hydrodistillation and solid-liquid extraction with methylene chloride and newer methods such as supercritical fluid extraction or subcritical water extraction which are safe environmentally. The highest crude extract was obtained by Soxhlet extraction and supercritical fluid extraction on the optimization conditions of 300 bar and 40°C (14.45% and 8.88%, respectively), while subcritical water extraction on 100°C provided the lowest yield of lipid extract (0.36%). Similarly, the major compounds from coriander oil [γ-terpinene, (+)-limonene, linalool, camphor, and geraniol] were obtained by Soxhlet extraction (785.05, 26.73 and 21.96 mg/100 g of coriander fruits, respectively). By the way, subcritical fluid extraction provided extraction of vegetal oil, while polyphenolics were also extracted by subcritical water extraction, increasing health value of obtained extracts, and presenting good alternatives for traditional techniques [26]. Although the examples given are reproduced, the volatile oil content and their rates are almost the same.

#### **5.2. Fatty acids**

regions have been present in a different ratio of the essential oil concentration. However, in the majority of studies the main component is defined as linalool (60-70%) [16, 17]; sometimes up to 87.54%. In addition, α-pinene, camphor and geraniol are also known as other important components and are responsible for the character of fragrance and aroma of the plant. The investigation on two coriander varieties (*vulgare* and *microcarpum*) from Turkey has resulted in oil content like 0.15–0.25% in *vulgare* (linalool 42.1–52.7%); and 0.31–0.43% in *microcarpum* (linalool 63.5–71.0%) [9]. In Iran, the essential oil from the dried fruit of the coriander has been found in the range of 0.1–0.36% represented by 34 compounds, linalool (40.9–79.9%) as major

**Figure 2.** The major constituents in the essential oil of coriander fruit: (a) linalool, (b) limonene, (c) camphor, and

In a study, the essential oil of coriander was obtained by supercritical water extraction, hydrodistillation, and Soxhlet extraction methods. The main component found was linalool (82.916%) chosen as the key component to find the best-operating conditions [20]. In fact, the parameters exhibit different impact to reach the volatile oil; pressure and temperature control influenced the

from Italian coriander fruits was performed under different temperature conditions. A decrease in the particle size improved the volatiles' yield so as to more ducts were destroyed during the milling process. Optimum supercritical fluid extraction conditions were found to be as follows: Pressure 90 bar, temperature 40°C, 1.10 kg/h and 0.6 mm. The compositions of each supercritical fluid extraction samples were analyzed by GC and GC/MS. The major components were linalool (65–79%), the others γ-terpinene (4–7%), camphor (3%), geranyl acetate (2–4%), *α*-pinene (1–3%), geraniol (1–3%) and limonene (1–2%) [28]. Linalool was determined as the highest percentage composition in the essential oil of *C. sativum* fruit (73.11%) [29], but this rate can vary during different maturation periods. Essential oil obtained by hydrodistillation increased markedly during the maturation process, and geranyl acetate (46.27%), linalool (10.96%), nerol (1.53%) and neral (1.42%) were the major compounds at the first stage of immature fruits. At the middle stage, linalool (76.33%), *cis*-dihydrocarvone (3.21%) and geranyl acetate (2.85%) were reported as the main constituents. Essential oils at the final stage of maturity (mature fruits) include mainly of linalool (87.54%) and *cis*-dihydrocarvone (2.36%) [30]. In another study, the volatile oils of coriander have been compared each other by conventional methods such as hydrodistillation and solid-liquid extraction with methylene chloride and newer methods such as supercritical fluid extraction or subcritical water extraction which are safe environmentally. The highest crude extract was obtained by Soxhlet extraction and supercritical fluid extraction on the optimization conditions of 300 bar and 40°C (14.45% and 8.88%, respectively), while

fluid extraction to obtain the volatile oil

yield and composition. In an example, supercritical CO<sup>2</sup>

component [27].

(d) geraniol.

170 Potential of Essential Oils

The vegetal oil (fixed oil/fatty oil) of coriander fruits, especially from French origin (23% yield), contain a high amount of monounsaturated fatty acids (1.8%); particularly petroselinic acid (73%) [22, 26]. The vegetable oil of coriander has been labeled as a Novel Food Ingredient (NFI), and it can be safely consumed as a food supplement by healthy persons, in maximum 600 mg/day dosages [22]. That is why, the essential oil of *C. sativum* fruits is called as triglyceride oil, due to the presence of petroselinic acid (**Figure 3**). The plant is recognized a potential source of lipids (rich in petroselinic acid) and essential oil (high in linalool) isolated from the fruits and the aerial parts [17]. The presence of petroselinic acid makes coriander more precious and interesting.

Petroselinic acid (18,1n-12) is classified as a monounsaturated the major omega-12 fatty acid exists in coriander oil, is a positional isomer of octadecenoic acid (its double bond being in position 6 instead of 9). Petroselinic acid has been detected at a level between 68 and 83% in coriander oil [31], or between 65–70% and 80.9% [9]. In a study, changes in fatty acids during maturation of coriander fruits cultivated in the North-East of Tunisia (Charfine) were studied. At full maturity, the main fatty acids were petroselinic acid (80.9 ± 5.7%), followed by linoleic (13.6 ± 2.9%), palmitic (3.6 ± 0.1%), and stearic (0.7 ± 0.1%) acids. During maturation of coriander fruit, saturated and polyunsaturated fatty acids decrease significantly, and monounsaturated fatty acids increase. It is necessary to underline that coriander fruits at the first four stages of maturity have a healthy nutritional value and the last five stages were with important economic and industrial applications [32, 33]. Commercial production of vegetable oils from oil-rich materials is based on through two traditional processes like the mechanical expression and extraction. In this manner, the maximum yield was obtained with single screw extruder for a configuration allowing the strongest oil expression. Comparing with a mechanical press, the maximum yield was obtained by the Soxhlet extraction with 21.25%, and the oil quality was found high grade. The acid value was under 1.8 mg of KOH/g of oil and iodine values were tolerable (44 mg of iodine/100 g of oil). In the oil, nine fatty acids were identified, with petroselinic acid accounting for 74–77% of the total fatty acids, followed by linoleic (12–13%), oleic (4–6%), and palmitic acids (3%). Moreover, *β-*sitosterol was the major sterol (28%) in all oils. The next major sterols in all oils were stigmasterol (24–27% of total sterols) and Δ<sup>7</sup> -stigmasterol (14–18% of total sterols) [9, 34, 35].

**Figure 3.** The structure of petroselinic acid.

#### **5.3. Polyphenols**

The polyphenols are very important secondary metabolites in coriander fruits and leaves because of their strong biological activities. Generally, flavones, tannins, and anthraquinones have been mentioned as the fruits phenolic constituents [21]. In coriander leaves, some phenolic compounds could be tentatively characterized using LC/MS. The polyphenol profile between leaves and fruits have been detected, and quercetin-glucuronide (**Figure 4**) was found as the major compound in plant parts, leaves and fruits [36]. Moreover, coriander leaves contain high amounts of caffeic, ferulic, gallic, and chlorogenic acids [12].

#### **5.4. Carotenoids**

Commercial varieties of coriander were analyzed by HPLC/MS and evaluated for carotenoids as *β*-carotene (vitamin-A precursor). In all varieties grown on similar conditions, *β*-carotene content was found higher in foliage at a mature stage, than in seedlings and seeds. For example, one of the varieties produced the highest biomass (6.18 ± 0.73 g/plant), total carotenoids (217.50 ± 5.6 mg/100 g DW) and *β*-carotene (73.64 ± 0.3 mg/100 g DW) at the pre-flowering stage. When the drying conditions are compared, microwave drying of foliage with oven drying one; the results showed that microwave drying protects pigments and trans-*β*-carotene [37]. The carotenoid content such as *β*-carotene (**Figure 5**), *β*-cryptoxanthin epoxide, lutein-5,6-epoxide, violaxanthin, and neoxanthin from the ether extract of coriander, the *β*-carotene was represented 61.14% of the carotenoids detected in the extract [38].

**6. Biological activities and usages of the coriander**

**Figure 6.** The structure of coriandrin.

**Figure 5.** The structure of *β*-carotene.

In the food industry, coriander is approved in food-use by the Food and Drug Administration (FDA in the USA), the Flavor and Extract Manufacturers Association and the Council of Europe. The plant can be mainly used as a spice, medicine, and raw material in food, beverage and pharmaceutical industries [16, 17]. Microwave-drying characteristics of coriander leaves were examined in designing and modeling heat and mass transfer processes during storage and other possible operations, necessary in food and chemical industry [42]. Moreover, the encapsulation (400 nm–7 μm) of the essential oil of coriander with chitosan obtained from the waste shells of crayfish (*Astacus leptodactylus*) has been arranged via the spray drying method led to the much higher antimicrobial activity and antioxidant activity than the oil and the pure chitosan. The created product could be beneficial in the food and pharmaceutical industries as a natural antioxidant and antimicrobial agent [43]. One of the reasons for being famous as a spice in the food industry is to use as a common flavoring substance for the pleasant aromatic odor of their stems, leaves, and fruits. That is why it is used in seasonings for sausages, and other meat products besides in baked goods, beverages, sweets, chewing gums, tobacco products, condiments, preservative, and also functions as an essential ingredient in curry powder. On the other hand, it should not be forgotten that coriander and its oil are used especially in perfumery and cosmetics. The warm and sweet notes of coriander oil mixed with other floral notes for oriental type perfumes have a different effect. It is used not only in perfumes but also in soaps, creams, lotions and in aromatherapy as much as covering the taste of some medicines [19]. The leaves are used for flavoring curries, sauces, and soups, while the whole young plants are used for preparing chutneys. All parts of *Coriandrum sativum* are edible and used as a spice in daily life [44]; however, its fresh leaves and dried fruits are the most frequently used parts. Green foliage, known to be rich in proteins, vitamins, and minerals (such as calcium, phosphorus, and iron), fibers and carbohydrates, are reportedly used as vegetables in salads. While the coriander fruits are very popular as health-supporting as the healing spices, the essential oil of coriander can be marketed as a food supplement at a maximum dosage of 600 mg per day. On the other hand, the fruits are a rich source of lipids (fatty acids) (28.4%), which may be of great

Coriander and Its Phytoconstituents for the Beneficial Effects

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#### **5.5. Isocoumarins**

There are no recent articles regarding the isocoumarins from coriander. The isocoumarins, coriandrones A and B, together with coriandrin (**Figure 6**) and dihydrocoriandrin were isolated from the aerial parts of *C. sativum* [39]. In addition, coriandrones C-E were also isolated from the methanolic extracts of the aerial parts of the coriander cultivated in the botanical garden of the Osaka University of Pharmaceutical Sciences [40]. Extracts of coriander were analyzed for photoactive constituents using HPLC and photobiological assay. Similarly, photoactive furoisocoumarins named as coriandrin and dihydrocoriandrin were also obtained, and their structures determined by 1 H, <sup>13</sup>C NMR and X-ray crystallography [41].

**Figure 4.** The structure of the quercetin-glucuronide.

**Figure 5.** The structure of *β*-carotene.

**5.3. Polyphenols**

172 Potential of Essential Oils

**5.4. Carotenoids**

**5.5. Isocoumarins**

and their structures determined by 1

**Figure 4.** The structure of the quercetin-glucuronide.

The polyphenols are very important secondary metabolites in coriander fruits and leaves because of their strong biological activities. Generally, flavones, tannins, and anthraquinones have been mentioned as the fruits phenolic constituents [21]. In coriander leaves, some phenolic compounds could be tentatively characterized using LC/MS. The polyphenol profile between leaves and fruits have been detected, and quercetin-glucuronide (**Figure 4**) was found as the major compound in plant parts, leaves and fruits [36]. Moreover, coriander

Commercial varieties of coriander were analyzed by HPLC/MS and evaluated for carotenoids as *β*-carotene (vitamin-A precursor). In all varieties grown on similar conditions, *β*-carotene content was found higher in foliage at a mature stage, than in seedlings and seeds. For example, one of the varieties produced the highest biomass (6.18 ± 0.73 g/plant), total carotenoids (217.50 ± 5.6 mg/100 g DW) and *β*-carotene (73.64 ± 0.3 mg/100 g DW) at the pre-flowering stage. When the drying conditions are compared, microwave drying of foliage with oven drying one; the results showed that microwave drying protects pigments and trans-*β*-carotene [37]. The carotenoid content such as *β*-carotene (**Figure 5**), *β*-cryptoxanthin epoxide, lutein-5,6-epoxide, violaxanthin, and neoxanthin from the ether extract of coriander, the *β*-carotene

There are no recent articles regarding the isocoumarins from coriander. The isocoumarins, coriandrones A and B, together with coriandrin (**Figure 6**) and dihydrocoriandrin were isolated from the aerial parts of *C. sativum* [39]. In addition, coriandrones C-E were also isolated from the methanolic extracts of the aerial parts of the coriander cultivated in the botanical garden of the Osaka University of Pharmaceutical Sciences [40]. Extracts of coriander were analyzed for photoactive constituents using HPLC and photobiological assay. Similarly, photoactive furoisocoumarins named as coriandrin and dihydrocoriandrin were also obtained,

H, <sup>13</sup>C NMR and X-ray crystallography [41].

leaves contain high amounts of caffeic, ferulic, gallic, and chlorogenic acids [12].

was represented 61.14% of the carotenoids detected in the extract [38].

**Figure 6.** The structure of coriandrin.
