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Progress in Essential Oils: Tagetes Oil

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A survey of the literature reveals that tagetes oil (Tagetes minuta L.) has been reviewed a number of times before (Lawrence, 1992, 1996, 2000, 2006 and 2009). However, over the last 15 years a number of studies were missed. These are included in this current review.

Prakasa Rao et al. (2000) examined the effect of fertilization on the growth and oil yield of T. minuta grown as a main and ratoon crop (second harvest). They found that the application of 100 kg N./ha increased the oil yield from 7.0–9.8 kg/ha to 21.3–21.8 kg/ha. In addition, the authors examined the main constituent content of T. minuta harvested at various growth stages. The result of this study can be seen in T-1.

Singh et al (2003) examined four crop practices that can be used for T. minuta grown in sub-temperate regions of India. They found that the oils produced from the different cropping practices were rich in different major constituents. For example, an ocimene-rich oil is obtained from T. minuta harvested in the winter (December–January); a dihydrotagetone rich oil is obtained from plants harvested in the autumn (October–November); a tagetone-rich oil is obtained from plants harvested in the summer (June) and a tagetenone-rich oil is obtained in the winter if the plants are grown as a short duration crop (seed sowed in September). It was determined that the highest oil yield (60–68 kg/ha) could be obtained from plants sowed in late June and harvested October 20–November 15.

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The major constituents of an oil of T. minuta that was produced commercially in Madagascar were determined by Juliani et al. (2004) to be as follows:

 

α-pinene (2.0%)

limonene (7.4%)

dihydrotagetone (11.6%)

tagetone* (14.1%)

(Z)-tagetenone (6.7%)

(E)-tagetenone (9.0%)

b-caryophyllene (1.1%)

bicyclogermacrene (2.2%)

*correct isomer not identified

 

El-Deeb et al. (2004) reported the results of their analysis of a hydrodistilled oil produced from full flowering T. minuta grown in the southern region of Saudi Arabia. As most of the constituents listed by the authors were incorrectly identified, no data will be included in this review.

Babu and Kaul (2007) examined the use of vacuum distillation as a method to produce an oil from T. minuta. They found that conventional ambient pressure distillation was far superior than any reduced pressure distillation irrespective of the vacuum level used. The authors also reported that the main constituents of the oil produced conventionally using GC/MS as their method of analysis were as follows:

 

limonene (6.0%)

(Z)-β-ocimene (49.3%)

dihydrotagetone (12.1%)

(E)-tagetone (0.4%)

(Z)-tagetone (3.7%)

(Z)-tagetenone (3.7%)

(E)-tagetenone (3.0%)

 

Chamorro et al. (2008) examined the content of the main oil constituents of 19 different collections of T. minuta growing in its natural habitat throughout Chaco Province (Argentina). They found the level of each constituent of the flower oil ranged as follows:

 

β-phellandrene (0.5–2.5%)

limonene (4.6–11.1%)

β-ocimene* (28.4–55.3%)

dihydrotagetone (3.9–14.3%)

tagetone* (3.1–14.4%)

tagetenone* (19.0–47.5%)

*correct isomer not identified

 

The effect of row spacing and nitrogen fertilization on T. minuta grown in Lucknow (Uttar Pradesh, India) was studied by Singh et al. (2008). They found that a 30cm row spacing and addition of 150 kg N/ha produced the highest oil yield. The main components of this oil, which was produced in 71 kg/ha were:

 

limonene + (Z)-b-ocimene (17.9%)

dihydrotagetone (24.7%)

(E)-tagetone (3.5%)

(Z)-tagetone (23.6%)

(E)-tagetenone (3.4%)

(Z)-tagetenone (13.6%)

 

A commercial oil of T. minuta that was purchased in S. Africa was analyzed by Oyedemi et al. (2008) using GC/MS only. The constituents characterized in this oil were:

 

δ-3-carene† (30.1%)

dihydrotagetone (14.1%)

naginatene† (2.3%)

β-ocimene* (5.0%)

tagetone* (7.3%)

terpinen-4-ol (3.1%)

†incorrect identification

*correct isomer not identified

 

The authors also misidentified a further 15 so-called constituents. The African Journal of Biotechnology needs to pay a lot more attention to the quality of their so-called peer-reviewed journal.

An oil of T. minuta that was produced from plants growing in Argentina was screened for its mosquito repellent activity by Gillis et al. (2008). The main components of this oil were characterized as:

 

α-pinene (11.8%)

limonene (66.3%)

carvone (0.1%)

(Z)-tagetenone (2.7%)

(E)-tagetenone (19.1%)

β-caryophyllene (14.8%)

germacrene D (0.4%)

α-humulene (1.4%)

T-cadinol (0.8%)

β-eudesmol (0.4%)

 

As can be seen there was an error in this report as the constituents characterized totaled 117.8%; however, it is included for the completeness of this review.

Tagetes minuta plants collected at their full flowering stage from the Dehradun region of Uttarakhand (India) by Kumar et al. (2009). Analysis of this oil by GC/MS and GC-FID revealed that the following constituents were characterized:

 

sabinene (0.5%)

o-cymene† (0.1%)

limonene (5.8%)

(Z)-β-ocimene (22.8%)

(E)-β-ocimene (0.3%)

dihydrotagetone (45.7%)

p-menth-4-en-3-one† (0.1%)

allo-ocimene* (0.4%)

(E)-tagetone (2.0%)

(Z)-tagetone (9.2%)

terpinen-4-ol (0.2%)

(Z)-tagetenone (1.7%)

(E)-tagetenone (1.8%)

β-caryophyllene (0.8%)

α-humulene (0.8%)

spathulenol (1.0%)

caryophyllene oxide (1.1%)

*correct isomer not identified

†incorrect identification

 

Analysis of a commercial sample of T. minuta using GC-Olfactometry methodology, such as Aroma Extract Dilution Analysis (AEDA) and Vocabulary-Intensity-Duration of Elementary Odors by Sniffing (VIDEO-Sniff), was the subject of study by Breme et al. (2009). The AEDA GC-O method is a dilution to threshold GC measurement best used with a minimum of eight judges. In contrast the VIDEO-Sniff GC-O method, which was developed by the French National Agronomy Research Institute (INRA) combines detection frequency and time intensity, which includes a developed vocabulary that is used to differentiate odors into olfactory groupings. The important odorant compounds identified in T. minuta oil by AEDA in order of importance were as follows:

 

(E)-tagetenone

ethyl isobutyrate

3-methyl-1-2-buten-1-thiol

ethyl isobutyrate

2-methylfuran-3-thiol

decanal

linalool

terpinen-4-ol

(Z)-tagetenone

(Z)-tagetone

(E)-tagetone

allo-ocimene isomer

octanal

ethyl 2-methylbutyrate

octyl acetate

1-nonen-3-ol

myrcene

1-octen-3-one

methyl 2-methylbutyrate

hexanal

butanone isomer

 

In contrast, the potent odorants in T. minuta oil as determined by VIDEO-Sniff GC-Omethodology were in order of intensity as follows:

 

isobutyl butyrate

dihydrotagetone

ethyl 2-methylbutyrate

(Z)-3-hexenyl acetate

terpinen-4-ol

allo-ocimene isomer

ethyl isovalerate

α-phellandrene

methyl 2-methylbutyrate

isoamyl acetate

2-methylbutyl acetate

limonene

(Z)-tagetone

ethyl isobutyrate

isovaleraldehyde

heptanal

1-octen-3-ol

myrcene

camphor

borneol

1-octen-3-one

(Z)-tagetenone

butenone isomer

methyl 3-methyl-2-butenoate

(E)-tagetenone

hexanal

1-nonen-3-ol

decanal

carvone

isobutanal

1-nonen-3-one

α-pinene

(E)-tagetone

2-methylbutanal

amyl isovalerate

 

As can be seen, the results of AEDA relate to the importance of the odorants based on their percentage composition and threshold, while the results of the VIDEO-Sniff methodology appears to this reviewer to relate to the odor intensity of individual oil constituents irrespective to their percentage amounts in the oil.

Ramaroson-Raonizafinimanana et al. (2009) collected 18 T. minuta plants with flower colors ranging from sulphur-yellow to orange-purple from the highlands and eastern parts of Madagascar. Oils were produced by steam distillation from the various collections in 0.10–0.17% yield. A summary of the results of the analyses of the oils produced from various flower-colored T. minuta can be seen in T-2. The analyses, which were performed using GC-FID and GC/MS, revealed that there was not a direct relationship between the oil composition and flower color. Also, the compositions of the oils produced from the different flower types varied widely. Finally, the oil compositions were mostly dissimilar to those normally encountered from T. minuta. The authors believed that their results indicated the existence of chemotypes hither too not encountered before.

Marotti et al. (2010) examined the flowers, shoots and roots for their thiophene contents. The main thiophene isomers found were 5-(3-buten-l-ynyl)-2, 2’-bithienyl (BBT), 5-(4-acetoxy-1-butynyl)-2,2’-bithienyl (BBTOAC), 5-(4-hydroxy-1-butynyl -2, 2’bithienyl (BBTOH) and 2, 2’:5’, 2”-terthienyl (a-T). A summary of the results is shown in T-3. As can be seen, no thiophene isomers were detected in the flowers.

Ghiasvand et al. (2011) collected T. minuta plants in full flower after which they were dried and ground and 0.5g was placed in a 40mL vial containing 500mL of double distilled water. The vial was initially shaken vigorously and then was placed in an ultrasonicator and incubated at 70°C for 15 min to allow full equilibration of the volatiles. Headspace volatiles were isolated from this aqueous mixture using a PDMS SPME fibre placed into the vial for 40 minutes. Analysis of the volatiles isolated from the fibre was performed by GC/MS only. The constituents characterized in the headspace were compared with an oil produced from the same batch of plants by hydrodistillation. The results of this comparative study are presented in T-4.

Ranade (2009) reported that Indian tagetes oil contains the following major constituents:

 

ocimene* (8.5%)

limonene (14.0%)

linalool† (21.1%)

linalyl acetate† (13.8%)

tagetone* (40.4%)

*correct isomer not identified

†not a T. minuta oil constituent

 

An oil of T. minuta was produced by hydrodistillation from plants grown in Khoramabad (Iran) from seeds collected from Namibia where the plant grows wild. Analysis of the oil by Meshkatalsadat et al. (2010) using GC-FID and GC/MS revealed that it possessed the following composition:

 

α-pinene (0.5%)

sabinene (0.8%)

limonene (13.0%)

dihydrotagetone (1.2%)

p-cymenene (1.0%)

terpinolene (11.0%)

(Z)-epoxy-b-ocimene (2.6%)

(E)-epoxy-b-ocimene (1.2%)

(Z)-tagetone (3.2%)

(E)-tagetone (5.7%)

p-cymen-8-ol (2.0%)

linalyl propionate (0.9%)

verbenone (3.7%)

(Z)-tagetenone (5.1%)

piperitone (6.0%)

piperitenone (12.2%)

piperitone oxide (1.2%)

spathulenol (0.7%)

caryophyllene oxide (3.0%)

heptadecane (0.7%)

neophytadiene (0.6%)

octadecane (0.9%)

nonadecane (1.2%)

heneicosane (2.5%)

docosane (5.0%)

tricosane (4.2%)

incorrect identification

 

Fresh T. minuta plants were collected in their flowering-fruiting stage from wild plants growing in the Sierras Grandes de Córdoba (Argentina) by Vazquez et al. (2011).

The fresh aerial plants were divided up into flowers, leaves, stems as well as the whole plant. These were separately chopped and placed in vials from which their headspace volatiles were determined by GC-FID and GC/MS, and compared with the composition of an oil produced by 3hr hydrodistillation (see T-5).

Saharkhiz et al. (2012) performed pot experiments on the foliar application of diammonium phosphate (DAP) on T. minuta. Oils produced from the various levels of DAP application were analyzed by GC-FID and GC/MS and found to contain similar constituents as shown as follows:

 

sabinene (1.8–3.5%)

(Z)-β-ocimene (7.0–12.9%)

(E)-β-ocimene (0–0.1%)

dihydrotagetone (62.5–74.6%)

α-pinene oxide (0–0.1%)

β-thujone (0–t)

allo-ocimene* (0–t)

β-pinene oxide (0.4–0.7%)

(E)-tagetone (0.6–2.3%)

(Z)-tagetone (9.0–11.2%)

methyl salicylate (0–t)

verbenone (0–0.1%)

(Z)-tagetenone (1.5–4.5%)

(E)-tagetenone (1.9–5.0%)

isoeugenyl phenylacetate* (0–0.2%)

β-caryophyllene (0.1–0.4%)

α-humulene (0–0.2%)

bicyclogermacrene (0–0.7%)

caryophyllene oxide (0–t)

neophytadiene (0–0.2%)

*correct isomer not identified

t = trace (< 0.05%)

 

The authors concluded that a 7.2% DAP foliar spray enhanced the biosynthesis of essential oil in the aerial parts, although not significantly.

The effect of transplanting date on the production of T. minuta oil and its major constituents was studied by Kumar et al. (2012).

The oils produced by 4hr hydrodistillation from plants in full flower that were transplanted between April 12 to June 25 in Palampur (Uttarakhand, India) were analyzed by GC-FID and GC/MS. The results of which can be seen in T-6.

Tagetes minuta plants were collected from different locations in Chaco Province (Argentina) at different times of the year. Oils produced from vegetative plants with flowers and flowers with seeds were examined by Chamorro et al. (2012). The major constituents characterized in these oils can be seen in T-7.

Garcia et al. (2012) determined that a 20% solution of tagetes oil had great potential as an environmentally accaricide against four tick species in Brazil. The oil used in this study contained the following major constituents:

 

limonene (7.0%)

(Z)-β-ocimene (5.1%)

dihydrotagetone (54.2%)

(E)-tagetone (6.7%)

 

Tagetes minuta plants grown in an experimental garden in lsfahan (Iran) by Shirazi et al. (2014) that were harvested in full flower, were subjected to hydrodistillation for 3 hr. Analysis of the oil using GC/MS only resulted in the characterization of the following constituents:

 

α-pinene (0.3%)

sabinene (0.4%)

(Z)-3-hexenyl acetate (0.2%)

p-cymene (0.9%)

limonene (3.1%)

(Z)-b-ocimene (7.9%)

dihydrotagetone (33.8%)

allo-ocimene* (0.4%)

(E, Z)-epoxy-β-ocimene (2.0%)

(E)-tagetone (16.1%)

(Z)-tagetone (0.2%)

p-mentha-1,8-dien-3-one

(Z)-tagetenone (5.3%)

(E)-tagetenone (19.9%)

thymol (0.5%)

carvacrol (0.5%)

(Z)-isoeugenol (0.9%)

β-carophyllene (0.3%)

α-humulene (0.2%)

germacrene D (0.4%)

spathulenol (0.4%)

*correct isomer not identified

 

The effect of shade and plant spacing on T. minuta was studied of over two years in Palampur (Himachal Pradesh, India by Kumar et al. (2014). Plant spacings of 45 × 30cm, 45 × 45 and 45 × 60 were studied and the effect of shading levels of 0, 25%, 50% and 75% were examined. The authors determined that 25% shade and spacings of 45 × 45 and 45 × 30 yielded the highest oil contents; however, the biomass was greatest for the 45 × 30cm spacing. The effect of spacing on oil composition of the flowers and leaves can be seen in T-8.

Examination of these results reveals that the leaf oil is richer in dihydrotagetone, the flower oil is richer in (E)-tagetenone and both oils have fairly similar (E)-tagetone contents.

 

B.M.Lawrence,Tagetes oil. In: Progress in Essential oils. Perfum. Flavor., 17(5), 131–133 (1992); 21(5), 64, 67–68 (1996); 25(6), 38–46 (2000); 31(9), 58–62 (2006); 34(8), 54–57 (2009).

E. V. S Prakasa Rao, K. Puttanna and S. Ramesh, Effect of nitrogen and harvest stage on the yield and oil quality of Tagetes minuta L. in tropical India. J. Herbs Spices Med. Plants, 7(3), 19–24 (2000).

V. Singh, B. Singh and V. K. Kaul, Domestication of wild marigold (Tagetes minuta L.) as a potential economic crop in western Himalaya and North Indian plains. Econ. Bot., 57,535–544 (2003).

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K. S. El-Deeb, F. A. Abbas, A. El Fishawy and J. S Mossa, Chemical composition of the essential oil of Tagetes minuta growing in Saudia Arabia. Saudi Pharmaceut. J; 12(1), 51–53 (2004).

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E. R. Chamorro, G. Ballerini, A. F. Sequeira, G. A. Velasco and M. F. Zalazar, Chemical Composition of essential oil from Tagetes minuta leaves and flowers. J. Argent. Chem. Soc., 96(1/2), 80–86 (2008).

M. Singh, R. S. Tripathi, S. Singh and M. Yaseen, Influence of row spacing and nitrogen levels on herb and essential oil production and oil quality of Tagetes minuta L. J. Spices Arom. Crops,17, 251–254 (2008).

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I. Marotti, M. Marotti, R. Piccaglia, A. Nastri, S. Grandi and G. Dinelli, Thiophene occurrence in different Tagetes species: agricultural biomasses as sources of biocidal substances. J. Sci. Food Agric., 90 1210–1217 (2010).

A. R. Ghiasvand, M. Nasseri, S. Farsizaeh, M. H. Meshkatalsadat, R. Sadeghi-Sarabi, S. Shadabi and M. Borzoei, Chemical characterization of cultivated Tagetes minuta L. by use of ultra sound assisted heeadspace SPME and GC-MS. Chromatographia, 73, 1031–1035 (2011).

V. G. Gillij, R. M. Gleiser and J. A. Zygadlo, Mesquito repellent activity of essential oils of aromatic plants growing in Argentina. Bioresource Technol., 99, 2507–2515 (2008)

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K. Breme, P. Journayre, X. Fernanclez, U. J. Meierhenrich, H. Brevard, D. Joulain and J-L. Berdague, Identification of odol-impact compounds of Tagests minuta L. essential oil: Comparison of two GC-Olfactometry methods. J. Agric. Food Chem., 57, 8572–8580 (2009).

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M. H. Meshkatalsadat, J. Safaei-Ghomi, S. Moharraimpour and M. Nasseri, Chemical characterization of volatile components of Tagetes minuta L. Cultivated in South West of Iran by injection. Digest J. Nanomaterials Biostructures, 5(1), 101–106 (2010). nanoscale

A. M. Vazquez, G. L. Demmel, S. G. Criado, M. L. Aimar, J. J. Cantero, L. I. Rossi and M. I. Velasco, Phytochemistry of Tagetes minuta L. (Asteraceae) from Córdoba, Argentina: Comparative study between essential oil and HS-SPME analyses. Boll. Latinamer. Caribe Plant. Med. Arom., 10, 351–362 (2011).

M. J. Saharkhiz, M. N. Estahbanati, M. Rezaei, E. Tafazoli and H. Delavar, Foliar application of diammonium phosphate increases essential oil content and changes its compositions in Mexican marigold (Tagetes minuta L.). J. Essent. Oil Bear. Plants, 15, 244–249 (2012).

R. Kumar, K. Ramesh, V. Pathania and B. Singh, Effect of transplanting date on growth, yield and oil quality of Tagetes minuta L. in Mid hill of North-western Himalaya. J. Essent. Oil Bear. Plants, 15, 405–414 (2012).

E. R. Chamorro, S. N. Zambor, W. G. Morales, A. F. Sequeira and G. A. Velasco, Study on the chemical composition of essential oils by gas chromatography. In: Gas Chromatography in Plant Science, Wine Technology, Toxicology and some specific Applications. Edit. B. Salih and O. Çelibiçak, pp. 307–323, In Tech Published on-line (2012).

M. V. Garcia, J. Matias, J. Cavalcanta Barros, D. Pires de Lima, R. daSilva Lopes and R. Andreotti, Chemical identification of Tagetes minuta Linnaeus (Asteraceae) essential oil and its acaricidal effect on ticks. Rev. Bras. Parasitol. Veterin., 21, 405–411 (2012)

M. T. Shirazi, H. Gholami, G. Kavoosi, V. Rowshan and A. Tafsiry, chemical composition, antioxidant, antimicrobial and cytotoxic activities of Tagetes minuta and Ocimum basilicum essential oils. Food Sci. Nutrition, 1–10 (2014).

R. Kumar, S. Sharma, K. Ramesh, V. Pathasia and R. Prasad, Irradiance stress and plant spacing effect on growth, biomass and quality of wild Marigold oil (Tagetes minuta L.)-an industrial crop in western Himalaya. J. Essent. Oil Res., 26, 348–358 (2014).

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T-1

Table 1

Comparative percentage composition of the oil of Tagetes minuta harvested at different growth stages

T-2

Table 2

Comparative percentage composition of Tagetes minuta oils of Madagascan origin produced from different flower typers

T-3

Table 3

Thiophene contents of Tagetes minuta

T-4

Table 4

Comparative percentage composition of the headspace volatiles and oil of Tagetes minuta

T-5

Table 5

Comparative percentage composition of the headspace volatiles of various parts of Tagetes minuta and its oil

T-6

Table 6

Effect of transplanting date on the major constituents of the leaf, stem and flower oils

T-7

Table 7

Comparative percentage composition of the major constituents of Tagetes minuta oils produced from different plant parts

T-8

Table 8

The effecet of plant spacing on the percentage composition of the leaves and flower of Tagetes minuta grown in Himachal Pradesh

Author Bio

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Brian M. Lawrence, Consultant

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