Asian Pac J Trop Biomed 2014; 4(9): 682-694 682

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Document heading doi: 10.12980/APJTB.4.2014C77 2014 by the Asian Pacific Journal of Tropical Biomedicine. All rights reserved. 襃 Chemistry and bioactivities of essential oils of some species: an overview

* Abhay Kumar Pandey, Pooja Singh , Nijendra Nath Tripathi Bacteriology and Natural Pesticide Laboratory, Department of Botany, DDU Gorakhpur University, Gorakhpur-273009, India

ARTICLE INFO ABSTRACT

Article history: Ocimum Essential oils of different species of the genus are natural flavouring materials of Received 23 Nov 2013 commercial importance. The data given in current literature are pertaining to the chemical Ocimum viz Ocimum basilicum Received in revised form 13 May 2014 composition of essential oils of different species ., Linn. (alt. Ocimum basilicum minimum Ocimum basilicum purpurience Ocimum campechianum Accepted 28 Jun 2014 var. , var. ), 24 2014 Ocimum canum Ocimum americanum Ocimum citriodorum, Ocimum gratissimum Available online Jul Mill., Sims. ( ), Ocimum kilimandscharicum Ocimum micranthum Ocimum sanctum Linn., Linn., Willd., Linn., Keywords: Ocimum tenuiflorum Ocimum selloi Ocimum trichodon, Ocimum utricifolium ( L ) B Ocimum alt. inn. , enth., species from different geographical regions. A considerable difference in chemical composition of a Essential oil particular species is found, which may be due to their occurrence in different eco-climatic Chemistry zones and changes in edaphic factors. Attention is also focused on the biological properties Ocimum Biological properties of oils which are related to their various interesting applications as antimicrobial, antioxidant, repellent, insecticidal, larvicidal, nematicidal and therapeutic (anti-inflammatory, antinociceptive, antipyretic, antiulcer, analgesic, anthelmintic, anticarcinogenic, skin permeation enhancer, immunomodulatory, cardio-protective, antilipidemic) agents.

1. Introduction have long history of uses in culinary spices and folk medicine. For example, , , sage and Worldwide demand of essential oils has increased during thyme are typical seasonings in the Mediterranean region, the past few years. Essential oils are reported in aromatic and especially oregano is consumed in larger quantities which are distributed in Mediterranean and tropical all around the world as part of pizza seasoning mix[3]. countries across the world where they are esteemed as an Although there have been toxic components described for imperative component of the native medicine systems. some Lamiaceae plants, the importance of many family Almost all organs (flowers, buds, stems, leaves, fruits, members to the culinary and essential oil industries has seeds and roots) of aromatic plants contain essential oils. been commercially explored for more than 75 years[4-6]. These are accumulated in secretary cells, cavities, channels, Essential oils recovered from the Lamiaceae species have and epidermic cells[1]. Lamiaceae (syn. Labiatae) herb been used against different diseases like intestinal disorder family includes one of the richest essential oil bearing plant and bronchitis[7]. Ocimum family, consists of more than 252 genera and 7 000 species in The genus , comprising of more than 150 the vicinity of plant kingdom[2]. Lamiaceae family is known species grows widely and is distributed throughout Ocimum basilicum for the wealth of species with medicinal properties, which temperate regions of the world[6,8,9]. O. basilicum Ocimum gratissimum O. gratissimum have been used since early times and many of these species ( ), ( ) and Ocimum sanctum O. sanctum are common in Mediterranean region. Many species of ( ), commonly known as holy , basil (wild basil/East India basil) and sweet

*Corresponding author: Dr. Pooja Singh, Assistant Professor, Bacteriology & Natural basil, respectively, are frequently cultivated in several Pesticide Lab, Department of Botany, DDU Gorakhpur University, Gorakhpur-273009, countries of East Asia, Europe, America and Australia for I Ocimum americanum ndia. the production of essential oils[10,11]. E-mail: [email protected] O. americanum Ocimum canum O. Tel: +919415083883 ( ) formerly known as ( F P S CST UP L (G N CST AAS D 09 A canum oundation roject: upported by ucknow rant o. / , - , pril ) 3, 2007). , includes wild species in India, but is cultivated Abhay Kumar Pandey et al./Asian Pac J Trop Biomed 2014; 4(9): 682-694 683 3. Chemical composition in Indonesia for its essential oil for commercial purposes. Ocimum kilimandscharicum O. kilimandscharicum ( ), a O. basilicum variety species of , commonly called African Essential oils are very complex natural mixtures blue basil is known for its camphor like scent of its essential which contain about 20-60 components at quite different Ocimum minimum Ocimum citriodorum oil. Similarly, and concentrations. They are characterized by two or three O. basilicum also include variety species of popular in major components at fairly high concentration (20%-70%) Indonesia, Mexico and Africa for their naturally occurring as compared to other components present in trace amount. essential oils as in perfumery and cosmetic applications. Essential oils are complex mixtures of natural organic Ocimum tenuiflorum O. tenuiflorum Likewise, ( ) includes compounds which are predominantly composed of terpenic O. sanctum Ocimum variety species of . Traditionally, these hydrocarbons (myrecene, pinene, terpinene, limonene, α β species have been extensively utilized in food and perfumery p-cymene, - and - phellandrene) and terpenoids industries[12]. The aerial parts of the plants are considered (oxygen containing hydrocarbons) like acyclic monoterpene as antispasmodic, stomachic and carminative in native alcohols (geraniol, linalool), monocyclic alcohols (menthol, medicine[13]. 4-carvomenthol, terpineol, carveol, borneol), aliphatic Ocimum A high degree of polymorphism in the genus aldehydes (citral, citronellal, perillaldehyde), aromatic determines a large number of subspecies, different varieties phenols (carvacrol, thymol, safrol, eugenol), bicyclic and forms producing essential oils with varying chemical alcohol (verbenol), monocyclic ketones (menthone, composition offering variable level of medicinal potential[14]. pulegone, carvone), bicyclic monoterpenic ketones (thujone, Ocimum Essential oils extracted from plants have been verbenone, fenchone), acids (citronellic acid, cinnamic acid) reported to possess interesting biological properties. These and esters (linalyl acetate)[20]. Mono- and sesquiterpenoidal volatile oils have been applied in perfumery, to inhibit essential oil constituents are formed by the condensation of growth of microorganisms, in food preservation and in isopentenyl pyrophosphate units. Diterpenes usually do not O. basilicum O. canum aromatherapy. The potential uses of , occur in essential oils but are sometimes encountered as O. gratissimum O. sanctum and essential oils, particularly by-products. ’ as antioxidant and antimicrobial agents have also been Lawrence classified the basil oils into three large groups et al explored[15-18]. Recently, Mondal . reviewed the European type, exotic or reunion type and African type antimicrobial, adaptogenic, antidiabetic, hepato-protective, according to their chemical composition and geographical anti-inflammatory, anti-carcinogenic, radioprotective, origin[21]. He established four essential oil chemotypes immunomodulatory, neuro-protective, cardio-protective (methyl chavicol, linalool, methyl eugenol and methyl O. sanctum and mosquito repellent properties of [19]. In cinnamate) and also numerous subtypes of oils extracted O. basilicum order to investigate the structural activity relationship, it from [22]. According to the biosynthetic origin is necessary to know the chemical differentiation among of major compounds, he classified them as chemotypes with Ocimum volatiles of various species. Keeping this in view single or dual biosynthetic pathways. From time to time, viz we have reviewed here the chemistry of various samples of other chemotypes ., eugenol-rich and thymol-rich in Ocimum O. gratissimum O. canum oils from different geographical regions. Further, [23], sesquiterpenes-rich in and O. sanctum the objective of our ongoing investigation is to establish and terpinene-4-ol-rich[22,24] have also been Ocimum biological evaluation of oils as potential source for beneficial reported from different places. The species which uses. are reviewed here for their essential oil chemistry, have been collected from the different countries and regions of the world such as Bangladesh, Brazil, Cameroon, Egypt, 2. Chemical investigation on essential oils Europe, Guinea, India, Iran, Italy, Mali, Nigeria, Pakistan, Rwanda, Thailand, Togo, Turkey, Um Ruaba and Yaounde. Researches on chemical composition of most of the Literature survey revealed that chemical constituents and Ocimum essential oils were undertaken by various researchers using their respective percentage of several species GC GC-MS T (T 1) and’ techniques. he other techniques used are varied depending upon the origins and cultivars able . Kovat s index from packed capillary column, retention time It can be described from Table 1 that the major data from GC, HPLC, GC-MS, capillary GC, HRGG-FID, HRGG- constituents which have been isolated from different Ocimum MS and IR, C13, NMR. The constituents were identified by oils include 1,8-cineol, linalool, pinene, eugenol, calculation of their retention indices under temperature camphor, methyl chavicol, ocimene, terpinene, limonene n etc Ocimum programmed condition for -alkanes (C8-C20). Identification . Table 1 also demonstrates that within the of individual component was assigned by retention time species, there is a clear variation in their composition in comparison with authentic components and oil of known terms of type of constituents and their composition. The composition and by mass spectra with those obtained from chemical structures of these compounds are depicted in Wiley/NIST/Pfleger library spectra as well as with literature Figure 1. data. Abhay Kumar Pandey et al./Asian Pac J Trop Biomed 2014; 4(9): 682-694 684 4. Biological properties of Ocimum oils oil is related to its chemical composition. The relation between composition and bioactivity of the essence from Currently, the interests in natural products are focused the aromatic plants may be attributable both to their major on sources of alternative, more natural and environmentally components (alcoholic, phenolic, terpenic or ketonic friendly antimicrobials, pesticidals and therapeutic compounds) and the minor ones present in the oil. It may activities. The possibility of utilizing volatile oils is now act together synergistically or antagonistically to contribute being investigated. Generally the action of volatile oils to some activity of the tested oil. ExperimentsOcimum on biological is the result of the combined effect of both their active activities of essential oils from different species and inactive compounds. The inactive compounds might have been established by numerous researchers. In the influence resorption, rate of reactions and bioavailability present review, we have described theOcimum some important bio- of the active compounds. Several active components might properties of different essential oils of species from have a synergistic effect. Biological activity of an essential different parts of the world. Table 1 Ocimum Investigation on chemical composition of essential oils of different species. Plant species Major constituents (%) Investigator Place O. basilicum et al L. Methyl chavicol (70.00), Linalool (25.00), Eugenol (5.00) Mondawi .[118] Um Ruaba O. gratissimum et al L. 387EThymol (35.40), p-Cymene (18.30), Eugenol (10.70) Ntezuriubanza .[119] Southern Western Rwanda O. gratissimum γ 345CThymol (46.60), -Terpinene (22.40) O. basilicum Linalool (45.70), Eugenol (13.40), Methyl eugenol (9.57), Akgul[120] Turkey Fenchyl alcohol (3.64) O. canum Sims. 337CLinalool (82.30) O. gratissimum 345CThymol (46.00-7.00) O. gratissimum 387EThymol (35.40), Eugenol (10.70) Ocimum trichodon 213CEugenol (74.70) β Ocimum utricifolium Trans-Methylisoeugenol (49.70), Trans- -Ocimene (13.50), 243C β Cis- -ocimene (12.60) Ocimum utricifolium et al 298EMethyleugenol (73.60) J [26] R Ocimum utricifolium β anseen . wanda 364ATrans-Methylisoeugenol (35.60), Cis- -Ocimene (29.20) Ocimum utricifolium β 375IEugenol (39.40), Cis- -ocimene (41.00) Ocimum utricifolium β 378IEugenol (37.60), Cis- -ocimene (39.00) Ocimum utricifolium 392GMethyleugenol (86.60) Ocimum utricifolium 401CEugenol (71.00) Ocimum utricifolium 402CEugenol (71.00) Methyl chavicol (87.30), Linalool (5.40), Methyl eugenol (1.50), O. basilicum β α β et al -Caryophyllene (2.40), -Pinene (1.00), -Pinene (0.80), Khatri .[121] Pakistan Limonene (0.50), Camphene (0.20) O. basilicum et al Linalool, Methyl chavicol, Eugenol Marotti .[122] Italy O. basilicum et al Western provinces of Limonene (10.40), Linalool (50.80) Zallo .[28] Cameroon O. canum β 1,8-Cineole (78.30), -Pinene (5.80) O. gratissimum γ p-Cymene (7.00), -Terpinene (20.00), Thymol (46.20) O. basilicum et al Linalool, Methyl eugenol Chalchat .[123] Mali α O. basilicum Linalool (69.00), Eugenol (10.00), (E)- -Bergamotene (3.00), et al Keita .[124] Guinea Thymol (2.00) O. americanum et al L. citral type Geranial (37.70), Neral (27.90) Mondello .[125] Bangladesh O. americanum L. camphor Camphor (38.60), Limonene (10.60) type O. basilicum var. purpurascens Linalool (29.70), Geranial (27.40), Geranyl acetate (13.80) O. sanctum L. green Eugenol (41.70), Limonene (3.80), E. Caryophyllene (24.40) O. sanctum purple Eugenol (77.50), E-Caryophyllene (10.70) O. basilicum 1,8-Cineole (11.00), Linalool (42.50), Estragole (52.20) O. basilicum minimum var. Linalool (16.00), Estragole (52.20), 1,8-Cineole (7.40) et al O. basilicum Silva .[126] North Eastern Brazil var. α purpurascensus Linalool (39.30), -Muurolol (11.00) α O. basilicum Methyl eugenol (78.02), -Cubebene (6.17), Nerol (0.83), ε Ozcan and Chalchat[127] Turkey -Muurolene (0.74) Ocimum minimum Geranyl acetate (69.48), Terpinen-4-ol (2.35), Octan-3-yl- acetate (0.72) Abhay Kumar Pandey et al./Asian Pac J Trop Biomed 2014; 4(9): 682-694 685 Table 1, continued Ocimum Investigation on chemical composition of essential oils of different species. Plant species Major constituents (%) Investigator Place O. gratissimum et al L. Eugenol (54.00), 1,8-Cineole (21.60) Silva .[10] Brazil O. micranthum β Willd. Eugenol (64.80), (E)- -caryophyllene (14.30), Bicyclogermacrene (8.10) Ocimum selloi Benth. Anethole (64.60), Linalool (20.60) Tchoumbougnang O. gratissimum β γ et al -Phellandrene (21.10), Limonene (11.40), -Terpinene (21.90), Thymol .[80] Yaounde (11.20) O. basilicum et al Linalool (10.00), Methyl chavicol (60.30), Methyl cinnamate (6.30) Kasali .[128] Nigeria O. basilicum Linalool (44.18), 1,8-Cineole (13.65), Eugenol (8.59) Ismail[107] Egypt O. basilicum α α cv. Methyl chavicol (52.40), Linalool (20.10), Epi- -cadinol (5.90), Trans- - Sajjadi[13] Isfahan, Iran purple bergamotene (5.20) O. basilicum cv. Methyl chavicol (40.50), Geranial (27.60), Neral (18.50), Caryophyllene green oxide (5.40) O. sanctum Shyama Methyl eugenol (67.80), E-Caryophyllene (17.10) Awasthi and Dixit [129] Northern India O. sanctum β Rama Eugenol (46.20), E-Caryophyllene (27.60), -Elemene (16.30) O. basilicum β et al -Ocimene (2.27), Methyl chavicol (92.48) Bunrathep .[55] Pathumthani (Thailand) O. canum β Linalool (5.65), Neral (34.01), Geranial (37.89), -Caryophyllene (6.79) O. gratissimum β β γ Z (48 28) C (3 06) M (9 32) α- -ocimene . , - aryophyllene . , - uurolene . , -Farnasene (4.33), Eugenol (25.02) O. sanctum β -Caryophyllene (35.20), Methyl eugenol (53.67) O. basilicum et al 1,8-Cineole (4.00), Linalool (28.60), Estragole (21.70), (E)-Methyl Politeo .[17] Austria Cinnamate (14.30) Ocimum et al E (32 20 60 60) M (60 60 69 500) 1 8 C (0 90 Z [130] N B campechianum ugenol . - . , ethyl eugenol . - . , , - ineole . - oghbi . orth razil Mill. 19.70), Elemicin (0.20-65.90) O. gratissimum γ (5 Thymol (13.10-36.20), -Terpinene (0.20-28.10), 1,8-Cineole (0.00-25.20), samples) p-Cymene (4.40-19.90) O. basilicum et al Linalool (53.00), Methyl chavicol (29.00) Zheljazkov .[11] European O. basilicum et al Estragole (85.50), Linalool (1.71) Koba .[43] Lome (Togo) O. basilicum et al Methyl chevicol (70.04), Linalyl acetate (22.54) (13.56), Camphene (7.32) Anand .[47] Uttarakhand, India O. kilimandscharicum ‐ Camphor (56.07), DL Limonene O. gratissimum ‐ ‐ Eugenol (53.89), Cis ocimene (23.97), Germacrene D (10.36) O. gratissimum β et al Eugenol (63.70), (Z)- -ocimene (19.60), Germacrene-D (7.30) Verma .[48] Sub-tropical region of O. kilimandscharicum γ Camphor (63.40), Limonene (7.90), Camphene (5.80), -Terpinene (4.70) northern India O. basilicum et al var. Methyl cinnamate (59.95), Linalool (16.40), tau-Cadinal (4.37) Mohhiuddin .[131] Bangladesh purpurascens O. basilicum et al Methyl chavicol (62.00), Linalool (24.00) Sastry .[132] Deccan Region, India O. gratissimum Eugenol (74.80), Limonene 1,8-Cineole (10.80) O. tenuiflorum β Eugenol (84.00), -Caryophyllene (6.90)

4.1. Antimicrobial activity H3C OH

CH2 OH OCH3 3 3 3 The indiscriminate use of antimicrobial agents has resulted CH O 3 CH3 H C CH H C OH Methyl chavicol3 Linalool Thymol Eugenol Ocimene in the emergence of a number of drug-resistant bacteria and CH CH3 3 CH3 H C CH3 fungi. To overcome the increasing resistance of pathogenic O microbes, more effective antimicrobial agents with novel

C E C

2 O mode of action must be developed. ssential oils derived 3 H H Ocimum CH3 CH3 H3C CH3 γ CH3 O from several species have been reported to be Limonene 1,8 Cineole -Terpinene Geraniole Gamphor active against several Gram-positive and Gram-negative CH3 CH3 bacteria as well as against yeasts and fungi due to their

C 3 2 H C terpenic constituents. Recently, essential oils and extracts H H H 2 of certain plants have been shown to have antimicrobial 3 H C CH3 CH O et 3 [25] [1] CH OCH3 effects as well as imparting flavour to foods . Janssen β β al Ocimum -Caryophylene Estragole Anethole -Phellandrene Camphene . investigated the antimicrobial potential of four Figure 1. viz O. canum O. gratissimum Ocimum trichodon Chemical structure of some foremost compounds isolated species ., , , Ocimum O. urticifolium Escherichia and grown in Rwanda against from essential oils of species. coli E. coli , Bacillus subtilis B. subtilis , Staphylococcus ( ) ( ) Abhay Kumar Pandey et al./Asian Pac J Trop Biomed 2014; 4(9): 682-694 686 aureus S. aureus Trichophyton mentagrophytes of Alternaria alternata, Aspergillus Penicillium ( ) and var. species, interdigitale O. canum Fusarium nivale µ [26]. They found that was the most species, were at MIC 0.3 L/mL[41,42]. in vitro et al effective amongst the studied oils. Essential oil extracted The microbiological experiments of Koba . O. sanctum from the leaves of has been found to inhibit revealed that only the methyl eugenol and methyl eugenol/ in vitro E. coli, B. anthracis Pseudomonas growth of and t-anethole chemotypes were active against tested fungi and aeruginosa P. aeruginosa µ ( ) which showed its antibacterial bacteria[43]. Their MIC against fungi ranged from 80-150 L/ µ activity[27]. L and from 200-500 L/L respectively. Likewise, on tested µ As an example of antimycotic activity, the oil of bacteria, the MIC varied from 200-400 L/L and from 250- O. gratissimum µ leaves was fungicidal at 78 mg/L for 500 L/L respectively. In this work, there is no doubt that the Microsporum gypseum Trichophyton rubrum O. basilicum and , but a antifungal activity of chemotype methyleugenol concentration of 312 mg/L was required to inhibit growth against tested fungi is a predictable consequence of its high Candida albicans C. albicans Cryptococcus of ( ) and content in methyleugenol known as one of the phenolic neoformans [28]. Further, Basilico and Basilico reported the volatile molecules endowed with antimicrobial properties[44]. O. basilicum Aspergillus et al O. antifungal activity of oil against Pandey . did work on the antimicrobial activity of ochraceus sanctum Bacillus pumilus, B. subtilis, and found that oil was effective at 500 mg/L[29]. At against seven bacteria ( µ O. canum S. aureus, E. coli, Klebsiella pneumoniae, P. aeruginosa 500 g/L, oil exhibited 100% mycelial inhibition and Penicillium italicum Salmonella typhi Aspergillus niger against , post-harvest rotting fungus ), two filamentous fungi ( Citrus et al Aspergillus flavus C. albicans of fruits[30]. Moreira . worked on antimicrobial and ) and a yeast ( )[45]. The oil O. basilicum activity of on survival and growth of different inhibited 100% microbial growth at 700 mg/L for bacteria and E. coli E. coli et al strains of O157:H7[31]. The strains of exhibited 1 300 mg/L for fungi. Recently, Singh . investigated that O. canum similar susceptibilities to the action of the essential oil essential oil of strongly inhibited the mycobial assayed with the minimum inhibitory concentration (MIC) growth of seven post-harvest pathogenic fungal species Aspergillus flavus, Aspergillus nidulans, Aspergillus niger, and minimum bactericidal concentration (MBC) values were ( Aspergillus ochraceus, Mucor ., Penicillium italicum, 1.9 mL/100mL and 2.0 mL/100 mL, respectively. Mbata and sp O. gratissimum Penicillium oxalicum Rhizopus arrhizus Saikia investigated the antibacterial effect of and ) and found that Listeria monocytogenes et al oil against serotype and reported that oil was toxic at 500 mg/L against all the fungi[46]. Anand . µ at 20-250 g/mL, the essential oil progressively inhibited look for the antimicrobial activity of essential oils of three Ocimum viz O. basilicum O. kilimandscharicum the bacterial growth[32]. Similar antimicrobial activity is species ., , O. O. gratissimum S. aureus, reported in essential oils isolated from Amazonian basil, and against Gram-positive ( gratissimum Ocimum micranthum O. micranthum Enterococcus faecalis E. coli, P. and ( )[33,34]. ) and Gram-negative ( et al O. basilicum aeruginosa C. albicans Weseler . found that MIC value of against ) bacteria as well as yeast [47]. Report Helicobacter pylori µ O. gratissimum was of 286.7 g/mL while MBC value revealed that oil was the most effective µ et al et al increased upto 573.4 g/mL[35]. Wannissorn . by using with MIC values ranging from 1.5-12.5 mg/mL. Verma . O. gratissimum O. disc diffusion assay, evaluated the antimicrobial activity of evaluated the antibacterial activity of and O. basilicum O. basilicum O. gratissimum kilimandscharicum S. aureus Streptococcus mutans , var. citratum, , against , , O. tenuiflorum Enterococcus faecalis O. gratissimum essential oils from Thailand against zoonotic and found that oil was Salmonella E. coli enteropathogens including spp., O157, more toxic against all tested bacterial strains and showed Campylobacter jejunii Clostridium perferingens et and which a zone of inhibition ranging from 8-16 mm[48]. Pandey al O. sanctum are important for broiler export[36]. The zone of inhibition . investigated that oil was found to be toxic O. basilicum Erwinia herbicola ranges of 9-80 mm with var. citratum was the against two plant pathogenic bacteria Pseudomonas putida most potent. The antifungal activity of eugenol isolated from and by exhibiting complete inhibition O. gratissimum Alternaria Penicillium µ reported against and of their microbial growth[49]. Oil exhibited the MIC 2.0 L/ chrysogenum Erwinia herbicola µ Pseudomonas [37]. mL for and 1.0 L/mL for et al O. putida µ Bozin . reported the antibacterial activity of , but was bactericidal at higher doses of 8 and 4 L/mL basilicum against 13 human pathogenic bacteria and respectively. µ et al find that the MIC ranges of 8-30 L/mL[15]. Atanda . O. basilicum 4.2. Antioxidant activity investigated the ability of sweet basil ( ) in Aspergillus the growth control of aflatoxigenic fungus parasiticus et al [38]. Lee . did the work on inhibitory effect Antioxidants are substances that inhibit the oxidation of O. basilicum of oil and its main constituent eugenol and our cells from toxins such as free radicals. The toxins can be Microsporum gypseum linalool on (guinea pig infection) at from the natural digestion and metabolism of foods, alcohol, [39] O. basilicum MIC of 0.01%-0.03% . Similarly, inhibited the nicotine from cigarette smoke, environmental® factors, OTC S. enteritidis µ O. forskolei growth of at MIC=20.0-80.0 g/mL[40], drugs such as acetaminophen, (Tylenol ) prescription drugs, B. subtilis S. aureus etc Benth. oil of and by diffusion test were preservatives, . Reactive oxygen species− (ROS) including µ µ O. sanctum 1 2 at MIC 32 g/mL and 128 g/mL, respectively, and singlet oxygen ( O2), superoxide ion (O ), hydroxyl ion (OH-), Abhay Kumar Pandey et al./Asian Pac J Trop Biomed 2014; 4(9): 682-694 687 4.3. Repellent, insecticidal, larvicidal and nematicidal and hydrogen peroxide (H2O2) are highly reactive and toxic activities molecules generated in cells during normal metabolism. However, in response to a variety of factors including tobacco smoke, pollutants, ionizing radiations, alcohol, Plant based fumigants have long been touted as synthetic pesticides, and solvent, their production increases. attractive alternatives to synthetic fumigants for arthropods ROS can cause oxidative damage to proteins, lipids, enzymes, management because botanicals reputedly pose little threat Ocimum and DNA, and they have also been linked to pathogenesis to the environment or to human health. Genus of oxidative diseases. Living cells possess an excellent is known for pesticidal properties due to diverse group of scavenging mechanism to avoid excess ROS induced cellular compounds in its essential oil. Basil oil contains bioactive injury, however, with ageing and under influence of external constituents that are insecticidal and repellent[59-62]. Esther et al stresses, these mechanisms become inefficient, and dietary . observed that oil extracted from the leaves of tropical O. suave supplementation of synthetic antioxidants is required[50]. In shrub, cause mortality in all stages of the tick Rhipicephalus appendiculatus this context, aromatic plants, particularly their essential oils, [63]. A 10% solution was found Ocimum are being evaluated for antioxidant activity. plants to kill all immature and more than 70% of adults feeding contain large amounts of antioxidants other than vitamin C, on rabbits. The toxicity of the result in this study may be vitamin E, flavonoids and carotenoids. The presence of many due to the toxic effects of the compounds eugenol, mono Ocimum pharmacologically active compounds in species and sesquiterpenoids found in the plant extract[64]. Sosan et al O. gratissimum provides them protection against free radical induced . studied on larvicidal activity of on Aedes aegypti Ae. aegypti oxidative damage of cellular components. The antioxidant larvae of L. ( ) and found that oil capacity of basil essential oils has been studied several exhibited 100% mortality at 300 mg/L concentration of 24 h et al O. canum times[51-54]. Bunarathep . reported the comparative exposure[65]. However, a related species growing Ocimum antioxidant activity of essential oils of four species in Zimbabwe was reported to exhibit repellency against O. basilicum, O. canum, O. gratissimum O. sanctum Ae. aegypti et al ( and ) adults of [66]. Aslan . tested essential oil from O. gratissimum O. basilicum by DPPH bioassay and found that was the for their toxicity against the nymphs and adults O. sanctum O. canum Tetranychus urticae most antioxidative followed by , and of (Acari: Tetranychidae) and adults of O. basilicum Bemisia tabaci et al with EC50 values 30.20, 767.82, 8 343.19 and (Aleyrodidae)[67]. Cavalcanti . determined µ et al 47 057.45 g/mL respectively[55]. Politeo . pointed out the larvicidal activity of essential oils from Brazilian plants O. americanum O. gratissimum Ae. aegypti the antioxidant capacity of free volatile aglycons from basil and against [68]. O. basilicum O. americanum O. gratissimum ( ) by two different methods which were 2,2- The results showed that and et al diphenyl-1-picrylhydrazyl radical scavenging method have LC50 of 67 and 60 mg/L respectively. Ilondu . O. suave (DPPH) and ferric reducing/antioxidant power assay (FRAP)[17]. observed that (wild basil) caused mortality of Rhyzopertha dominica DPPH method shows that free volatile aglycones possess good adult in grain cereals at the antioxidant properties comparable with that of the essential 2-8 g plant materials per 50 g cereals (rice, maize and oil and well-known antioxidant butylated hydroxytoluene, sorghum)[69]. This protects the cereals after 90 d post et al but less than pure eugenol. The results obtained by FRAP treatment. Olonisakin . reported the insecticidal O. shave Callosobruchus maculatus method showed that these compounds are somewhat less activity of against et al effective antioxidants than essential oil and butylated with LC50 values of 0.66 mg/10 g seed[70]. Lopez . O. hydroxytoluene. From time to time, potential uses of found that estragole is example of toxic fumigant compound sanctum O. gratissimum O. basilicum O. basilicum , and essential oils in the basil essential oil ( ) that is active against et al as antioxidant agent have been explored[15,16,18]. Trevisan insect pests[71]. Bakr . evaluated the insecticidal effect et al O. basilicum . evaluated the antioxidant capacity of essential oils of volatile oil from basil ( ) against two museum Attagenus fasciatus obtained by steam hydrodistillation from five species of insect pests black carpet beetle ( , a Ocimum O. basilicum purpurascens the genus , namely var. , pest in the museums where it attacks) and cigarette beetle O. basilicum O gratissimum O. micranthum O. Lasioderma serricorne , . , and ( , a pest of stored tobacco), LC50 values tenuiflorum O. sanctum (syn. ), using a high-performance of oil against larvae and adults of the black carpet beetle 3 1 787 86 2 056 47 L 80 1 660 9 L 80 liquid chromatography-based hypoxanthine/xanthine were3 . and . m 3/ cm as well as . m / oxidase and the DPPH assays[56]. In the hypoxanthine/ cm and 2.014 59 mL/80 cm for the larvae and adults of et al xanthine oxidase assay, strong antioxidant capacity was cigarette beetle, respectively[72]. Manzoor . reported O. sanctum evident in all the oils, but the greater was shown by that the oil as toxicant and repellent agent against O. tenuiflorum O. sanctum µ Heterotermes indicola O. obtained from (syn. ) (IC50=0.46 L/ termite, [73]. Similarly, Basil oil ( O. basilicum purpurascens basilicum ’ mL) compared to var. (IC50=1.84 ) and its major constituent s trans-anethole, µ O. sanctum L/mL). In the recent research, and Omani estragole, linalool were insecticidal to adult fruit flies Ceratitis capitata C. capitata , Bactrocera dorsalis B. basil oils were also found to possess significant antioxidant of ( ) ( dorsalis Bactrocera cucurbitae B. cucurbitae action[57,58]. ), and ( )[74]. The C. capitata toxic action of basil oil in occurred significantly Abhay Kumar Pandey et al./Asian Pac J Trop Biomed 2014; 4(9): 682-694 688 B. cucurbitae, faster than that of in but slightly faster than metabolites (which are potential sources of drugs) and B. dorsalis B. dorsalis that of in . Estragole acted faster in essential oils of therapeutic importance. The important C. capitata B. cucurbitae than that of in and . Linalool action advantages claimed for therapeutic uses of medicinal B. dorsalis C. capitata B. was faster in and than that of in plants in various ailments are their safety besides being cucurbitae . Trans-anethole action was similar to all the economical, effective and easy available. Several studies C. capitata three species. Methyl eugenol acted faster in have shown that steam distilled essential oils extracted B. cucurbitae B. dorsalis Ocimum and than that of in . When linalool from fresh leaves of species have therapeutic B. cucurbitae was mixed with cuelure (attractant to male), its importance. potency to the three species decreased as the concentration O. suave 4.4.1. Anti-inflammatory, antinociceptive, antipyretic, of cuelure increased. Oil of (wild basil) was used antiulcer, analgesic and anthelmintic properties under ambient conditions with the aim of evaluating Musca the toxicity of the plant oil on adult housefly- Essential oil (200 mg/kg body weight) of fresh leaves domestica [75]. The oil applied at 0.05, 0.10, 0.15 and 0.20 mL/L and fixed oil (0.1 mL/kg, body weight) of seeds (fixed oil) Ocimum T LC50 0 09 caused significant mortality of the housefly. he was . of species have proved’ as anti-inflammatory mL/50 mL of water, and the LT50 was 4.40 h. This result shows agent on experimental animal s hind paw edema induced O. suave that leaf oil could be used as an alternative to by carrageenan, serotonin, histamine and prostaglandin- M. domestica synthetic insecticides for the control of . More E-2, significantly reduce the edema when compared with O. sanctum recently, Pandey and Tripathi reported that the dose of 5 and the saline treated control[82]. The oil of was µ O. sanctum 10 L oil was responsible for absolute repellent found to possess significant anti-inflammatory activity Cryptocarya and insecticidal activities against pulse beetles against carrageenan and different other mediator- chinensis Callosobruchus maculatus and respectively[76]. induced paw edema in rats[83]. This result supports the et al Rajamma . examined the comparative larvicidal activity dual inhibition of arachidonate metabolism and indicated Ocimum O. sanctum O. basilicum of different species of ( , by its activity in inflammation models that are intensive O. gratissimum Culex quinquefasciatus and ) against larvae of to selective cyclooxygenase inhibitors. The mechanism of in terms of LD50 value on late third or early fourth instar action of the anti-inflammatory effects of Tulsi could be larvae for a period of 24 h[77]. A comparison of LD50 value has the cyclo-oxygenase and lipooxygenase pathways[83,84]. O. basilicum O. sanctum shown that oil is more active than the other two In earlier work, oil of was found to inhibit the O. basilicum O. sanctum species. The LD50 value of and oils inflammation induced by carrageenan[85]. The oil also µ were 39.31 and 40.02 L/L on the laboratory reared larvae and possesses significant antipyretic, analgesic and antiarthritis µ et al 129.53 and 139.49 L/L on field collected larvae. Laboratory activity without any noticeable toxicity[86]. Sahouo . reared larvae were more sensitive than field collected larvae. reported inhibitory effect produced by chemical constituents O. gratissimum Bioassay tests were conducted to find out the nematicidal of essential oil as anti-inflammatory and O. basilicum Meloidogyne inconita in vitro activity of oil against [78]. analgesic drugs, , on soybean lipoxygenase L-1 et al The oil was highly toxic at 250 mg/L. Holetz . and cyclooxygenase function of prostaglandin H synthase O. gratissimum studied on effect of essential oil of on (PGHS), the two enzymes involved in the production of Herpetomonas samuelpessoai O. gratissimum the trypanosomatid [79]. mediators of inflammation[87]. inhibited µ They observed that at from 20-250 g/mL, the essential the two enzymes, cyclooxygenase function of PGHS and µ L 1 IC50 125 144 oil progressively inhibited the protozoan growth.° lipoxygenase - , with an values of and g/ The IC50 in defined and complex media, at 28 C were mL respectively. The proteins implicated in production of µ et al 100 and 91 g/mL, respectively. Tchoumbougnang . mediators of inflammation, proposed in literature, were PGHS O. gratissimum investigated the antimalarial activity of and lipoxygenase-5LO. Their natural substrate is arachidonic Plasmodium berghei essential oil on mice infected with [80]. acid. Indeed, it is well established that PGHS catalyzed The oil showed maximum 77.5% activity at 500 mg/kg of biotransformation of arachidonic acid into prostaglandins, mouse per day. Oil also showed significant suppression thromboxanes and prostacyclins which are mediators of parasitaemia (55%-77.8%) at oral dose ranges of of inflammation, hormonal modulation and platelet et al O. 200-500 mg/kg per day. Santoro . worked out on aggregation. Lipoxygenase 5LO catalyzed biotransformation basilicum oil and it active constituent eugenol, linalool and of arachidonic acid into fatty acid hydroperoxides, lipoxines, Trypanosoma observed that they were strong inhibitor of and leukotrienes, compounds implicated in allergy and cruzy which causes epimastigotes, trypomastigotes with LC50 suffering. Lipoxygenase L-1 was a model of lipoxygenase et al values ranges of 99.5-57.5 lg/mL[81]. 5LO and its natural substrate was linoleic acid[88]. Singh . O. sanctum showed that oil produced hypotensive effect in 4.4. Therapeutic properties of Ocimum oils anaesthetized dog, which seems to be due to its peripheral vasodilatory action. The oil increased blood-clotting time A variety of curative properties have been recognized to and percentage increases were comparable to aspirin and Ocimum species. The medicinal plants are rich in secondary could be due to inhibition of platelet aggregation[89]. The Abhay Kumar Pandey et al./Asian Pac J Trop Biomed 2014; 4(9): 682-694 689 O. gratissimum oil also showed inhibition towards cytochromatic enzyme Both oil and eugenol decrease the blood B DOCA responsible forO. hepatic gratissimum metabolism of pentobarbitone. oth pressure in conscious -salt hypertensive rats exhibitinget [100] I L eugenol and Haemonchus contortusoil presented anthelmintic alits cardiovascular effects . n earlier research, ahlou activity against , the main nematode . foundO. gratissimum that intravenous treatment of normotensive rats N B [90] of ovines and caprines inO. ortheasternmicranthum razil . with oil and its main constituent eugenol The essential oil of was studied for a dose dependently decreased mean aortic pressure[101]. possible analgesic effect on the acetic acid induced writhing Eugenol was also reported to induce vasorelaxant effects and formalin test in mice and antioedema activities on on rat and rabbit thoracic aorta as well as on rat mesenteric [102-104]. the carrageenan and dextran induced paw edema in rats. vascular bed O. sanctum The essential oil demonstrated antinociceptive effects, Essential oil from leaves has been shown and pretreatment with naloxone did not reverse the to have a potential for lipid-lowering action. The anti- antinociception, indicating that the opioid system is not hyperlipidaemicO. sanctum ability of the essential oil extracted from involved. On the other hand, pretreatment with L-arginine leaves in rats fed with high cholesterol diet was reversed the antinociception, suggesting involvement of investigated[105]. In conclusion, the researchers found that the nitric oxide system. The essential oil did not present an there was no significant differences in body weight gain, A antioedematogenic effectet al in the carrageenanO. gratissimum and dextran food intake, and heart weight in all groups of rats. uthors [91] R models . abelo . found that oil observed thatO. phenylpropanoid sanctum compounds, the main produced a dose-dependent inhibition of acetic acid- composition of essential oil is responsible for the 60% [105] I induced writhing, causing up to a ~ inhibition at the lipid lowering effect in O.high sanctum cholesterol rats . n another (300 ) highest dose mg/kg O.used gratissimum during their experiment finding by treating with oil to rats fed with a high antinociceptive effects of O. sanctumessential oil in cholesterol diet, it was found that essential oil suppressed mice[92]. The therapeutic use of in treatment of the high serum lipid profile and atherogenic index as well as MB gastric ulcer has been attributed to antiulcerogenic action of serum lactate dehydrogenase and creatine kinase subunit T [93,94] 4.4.2.eugenol Anti-cancerous and essential propertyoil extracted from ulsi leaves . without significant effect on high serum levels of aspartate O. basilicum aminotransferase, alanine aminotransferase and alkaline Estragole, a constituent of essential oil, phosphatase in rats fed with high cholesterol diet[57]. Oil was has shown carcinogenic properties in rat and mouse[95,96]. also found to decrease the high level of thiobarbituric acid P G rakash andO. uptasanctum investigated the chemoprotective reactive substances, glutathione peroxidase and superoxide activity of oil against subcutaneously dismutase without impacting catalase in the cardiac tissue injected 20-methylcholanthrene induced fibrosarcoma while in the liver, it decreased high level of thiobarbituric tumors in the thigh region of Swiss albino mice and acid reactive substances without significantly effecting found that supplementation of maximal tolerated dose glutathione peroxidase, superoxide dismutase and impacting µ O. sanctum (100 L/kg body weight) of the oil significantly reduced 20- catalase. Authors concluded that essential oil of methylcholanthrene induced tumar incidence and tumor has lipid-lowering and antioxidative effects that protect the [97] E volumeO.. sanctumarlier they reported the antiproliferative activity heart against hypercholesterolemia. H L [98] of the et al oil against e a cells in culture . 4.4.5. Immunomodulatory and CNS activity of Ocimum oils Manosroi . have shown an inhibition of the proliferation I of murine leukemia and humanO. mouth sanctum epidermalO. basilicum carcinoma n current competitive life, stress is a very common cell lines by essential oils of , and problem for human beings. Assembly of more free-radicals O. americanum[62] . due to stress leads to activity adverse effectsOcimum on various vital 4.4.3. As skin permeation enhancers organs and tissues of the human body. essential oil has gained special attention due to its biological properties, T he delivery of drugs via skin routes has been extensively however, little is known about its immunomodulatoryO. sanctum studied. Dermal and transdermal drug delivery is often effects. The immunomodulatory potential of oil limited by poor pfermeability of the stratum corneum on some immunological parameters in stressed and non- (SC) to drugs, which precludes their crossing the skin at stressed animal was carried out[106]. They concluded that therapeutic rates. The barrier properties of the SC can be by penetrating the oil it exert immunomodulatory effect reduced by the use of natural products. Essential oils are by modulating GABAergic activity and influence both receiving considerable interest as enhancersO. to basilicum improve humoral and cell mediated immunological parameters in E ( ) [106] I drug permeation. ssential oil of sweet basil native non-stressed as well as stressedviz animals . n CNS was evaluated as skin permeation enhancer to promote the this context, some activities O.., basilicumsedative, hypnotic, precutaneous absorption of drugs and reported it as noble anticonvulsant, local anesthetic of essential [99] I [107] W enhancers . oil were alsoO. basilicuminvestigated by smail . hen tested 4.4.4. Cardiovascular and anti-lipidemic actions of Ocimum in mice, oil had no effect on motor 1 2 L 90 oils activity up to a dose of . m /kg at mm post- administration. Pentabarbitone sleeping time tested in Abhay Kumar Pandey et al./Asian Pac J Trop Biomed 2014; 4(9): 682-694 690 Ocimum mice was significantly increased in mice by all doses of essential oils of collected species from different essential oil higher than 0.2 mL/kg. Intraperitoneal of oil geographical origins existed variety of chemical constituents, significantly increased in a dose dependent manner, the and the researchers found vide and varied application in latency of convolution and percent of animal exhibiting traditional healthcare system. The review of past studies H ED50 0 61 clonic seizures. e found values of oil were . , which has been discussed inOcimum this chapter showed that 0.43 and 1.27 mL/kg against convulsion induced by essential oils obtained from plants have gained pentylenetetrazole, picrotoxin and strychnine, respectively. much appreciation among food scientists and researchers He noted that the observed anticonvulsant and hypnotic because of their multifold biological activities. The reviewed activities of oil could be related to the presence of variety results aimed at attracting the attention of scientists and of terpenic constituents in it. It has been reported that researchers looking for new drugs from natural products terpenes have a protective effect against pentylenetetrazole as well as those investigating the pharmaceutical diversity [108,109] M T and picrotoxin-induced convulsions . odulation of of essential oils. he data reported in the present“ study glutamergic and GABAergic transmission are mechanisms provide a basis for reviving the old art of essential oil [110] ” indicated for anticonvulsant action on monoterpenesOcimum . therapy based on our modern scientific knowledge of their Linalool, the most abundant constituent of oil, has mode of action, supported by safety issues. Probably, such anticonvulsant activity against pentylenetetrazole-induced natural components might prove to be potentially beneficial E convulsion and also through inhibition of glutamergic butOcimum comparatively less toxic. ventually, plants belonging transmission as well as through suppression of voltage-gated to genus could contribute a lot to solve certain [111-113] O T current . n the other hand, other main constituent economy and healthOcimum problems. hus, essential oils and their of 1,8-cineole exerts anticonvulsant activity, potentiates constituents of species can hopefully be considered phenobarbitone sleeping time, and has an inhibitory effect in the future for more clinical evaluations and applications, on locomotory activity[114]. Eugenol, the other representative and as possible adjuvants to current medications. constituent, also exerts anticonvulsant property through GABA potentiating binding of to its receptor and by Conflict of interest statement increasing the affinity of these receptors to bind GABA[115]. Additionally, eugenol has anesthetic, sedative, and muscle [116] relaxant effects . et al We declare that we have no conflict of interest. I O CNS n research of liveiraO. basilicum., depressant“ and ( M anticonvulsant” effects of access aria Acknowledgements B ) onita leaf essential oilO. in basilicum different experimental models were investigated[117]. essential oil, at all doses, showed depressant CNS activity as revealed in the The authors thank the Head Department of Botany, DDU G U G general pharmacological screening; decrease of spontaneousO. orakhpur niversity, orakhpur for providing necessary A L N S L basilicumactivity, ataxia, and sedation. dditionally, all doses of facilities and the ibrary officers, ational cience ibrary, N M L N D FRI D essentialP oil induced a significant increase of ational edical ibrary, ew elhi, , ehradun and ( 0 05) CIMAP L D A K sleepingP O.time basilicum < . and decrease in the latency to sleep , ucknow for providing library facilities. r. . . ( <0.01). essential oil also increased the latency Pandey is grateful to CST UP Lucknow for financial assistance (G N CST/AAS D 09 A 3 2007) for development Pof convulsions in pentylenetetrazol and rant o. , - , pril , . ( 0 05) F picrotoxinO. basilicum tests < . . or pentylenetetrazol, the effectO. ofbasilicum essential oil was reversed by flumazenil. References essential oil didP not interfere with the convulsions ( 0 05) T O.induced basilicum by strychnine > . . heir data suggests that CNS [1] B urt S. Essential oils: their antibacterial properties and essential oil possesses depressant and Int J Food Microbiol potential applications in food-A review. anticonvulsant properties which could be mediated by an 94 interaction with central GABAergic receptors. 2004; : 223-253. [2] H edge C. A global survey of the biogeography of the Labiatae. Advances in labiatae In: Harley RM, Reynolds T, editors. 5. Conclusions science - . UK: Royal Botanic Gardens, Kew; 1992, p. 7 17. Origanum [3] B aser KH. The Turkish species. In: Kintzios SE, Oregano: The genera Origanum and Lippia T editor. . London: Ocimum here are many herbal plants in the world among which ( ) Taylor and Francis; 2002, p. 109. Tulsi is considered to be the ruler of herbs due ’ V [4] L awrence BM. Labiatae oils-mother nature s chemical factory. to its great medicinal ethics. arious medicinal properties T H Essential oils allured publishing carol stream IL; UK: Mendeley of ulsi are well documented in the indu mythology. C T Ltd; 1993, p. 188-206. [Online] Available from: http://legacy. onsidering the health beneficial effects of ulsi, our I T library.ucsf.edu/documentStore/i/u/d/iud13c00/Siud13c00.pdf. ancestors’ in ndia insisted to plant a ulsi sapling in everyone s house. 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