Journal of Biotechnology and Biodiversity | v.7 | n.3 | 2019
Journal of Biotechnology and Biodiversity
journal homepage: https://sistemas.uft.edu.br/periodicos/index.php/JBB/index
Content and composition of the essential oil of Artemisia annua in two harvest times
Paula Tatiana Lopes Seixasa, Henrique Guilhon Castrob*, Luiz Claudio Almeida Barbosaa , Antonio Jacinto Demunera, Marcelo Coutinho Picanço a
a Federal University of Viçosa (UFV), Brasil
b Federal University of Juiz de Fora (UFJF), Brasil
* Autor correspondente (hg.castro@uol.com.br )
I N F O A B S T R A C T
Keyworks
Artemisia annua essential oil
gas chromatography
coupled to mass spectrometry
medicinal plants
Artemisia annua is traditionally used in the treatment for malaria due to presence of the active principle artemisinin. The aim of the present study was to evaluate the essential oil content and chemical composi- tion of A. annua submitted to four doses of mineral fertilization in two harvest times. The seedlings of A. annua were cultivated in 10 L pots kept in a greenhouse. The tested doses of mineral fertilization were the following: without fertilization (D0), 50% of the recommended dose (D1), recommended dose (D2), and 150% of the recommended dose (D3). The samples for extracting the essential oils were collected at 60 and 125 days after transplantation (DAT). The essential oil was obtained by hydrodistillation using a Clevenger-type apparatus. Identification and relative percentage of the compounds of the essential oil were performed by gas chromatography coupled to mass spectrometry. The highest essential oil content obtained was 0.81% using the dose D0 at 60 DAT. The increase of the dose of mineral fertilization indi- cated a disadvantage with the reduction of the essential oil content in the two harvesting times. The major constituents found in the essential oil were camphor and borneol. The results indicate that A. annua could be an alternative source of borneol and camphor, active component with use in the chemical and p harma- ceutical industry.
R E S U M O
Palavras- chaves
Artemissia anuua óleo essencial
cromatografia gasosa
espectrometria de massa
plantas medicinais
Conteúdo e composição do óleo essencial da Artemisia annua em duas épocas de colheita.
Artemisia annua é utilizada tradicionalmente para o tratamento da malária devido à presença do princípio ativo artemisinina. O objetivo do presente estudo foi avaliar o teor e a composição química do óleo essen- cial de A. annua submetida a quatro doses de adubação mineral em duas épocas de colheita. As mudas de A. annua foram cultivadas em vasos de 10 L mantidas em casa de vegetação. As doses testadas de ferti- lização mineral foram as seguintes: sem fertilização (D0), 50% da dose recomendada (D1), dose reco- mendada (D2) e 150% da dose recomendada (D3). As amostras para extração dos óleos essenciais foram coletadas aos 60 e 125 dias após o transplante (DAT). O óleo essencial foi obtido por hidrodestilação usando um aparelho do tipo Clevenger. A identificação e a porcentagem relativa dos compostos do óleo essencial foram realizadas por cromatografia gasosa acoplada à espectrometria de massa. O maior teor de óleo essencial obtido foi de 0,81% na dose D0 aos 60 DAT. O aumento da dose de adubação mineral indicou uma desvantagem com a redução do teor de óleo essencial nas duas épocas de colheita. Os cons- tituintes majoritários encontrados no óleo essencial foram cânfora e borneol. Os resultados indicam que A. annua pode ser uma fonte alternative de borneol e cânfora, princípios ativos com uso na indústria química e farmacêutica.
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INTRODUCTION
Asteraceae is the largest family of flowering plants, consisting of 1,535 genera and approxi- mately 23,000 species, many of which are used for medicinal purposes (Fakim, 2006; Pellicer et al., 2008). The genera Artemisia, with 800 species dis- tributed worldwide, is industrially important due to its antifungal, insecticidal, allelopathic, and anti- bacterial properties, among others (Malik et al., 2009; Chauhan et al., 2010; Lutz et al., 2008).
The species Artemisia annua L. (A. annua) pre- sents an annual cycle and is a known natural pro- ducer of artemisinin, a sesquiterpene with antima- larial property (Yarnell & Abascal, 2004; Balunas & Kinghorn, 2005; Cavar et al., 2012; Herrmann et al., 2013).
Among the secondary metabolites of plants are essential oils which are complex mixtures that may contain more than a hundred organic compounds. The chemical constituents of these oils may belong to the most diverse classes of compounds. However the terpenes are the most commonly found com- pounds (Gonçalves et al., 2003; Castro et al., 2010; Veloso et al., 2014). The monoterpenes, sesquiter- penes, and oxygen derivatives of these substances are the predominant constituents of essential oils from several eucalyptus species (Barbosa et al., 2016; Ribeiro et al., 2018). In most cases the bio- logical activity of a particular essential oil may be related to the major constituent (Bakkali E Idaomar, 2008), although synergism may also occur between some compounds (Filomeno et al., 2017).
Within this context, the objective of this work was to evaluate the content and composition of the essential oil of A. annua submitted to four doses of mineral fertilization in two harvest times, as well as to identify the major constituents of the essential oil
MATERIAL E MÉTODOS
Preparation of seedlings and cultivation
The experiment was conducted in the Federal University of Viçosa- UFV, in Viçosa-MG, Brazil (20° 76’ 26’’S and 42° 86’ 40’’W with average al- titude of 690 m), in a greenhouse from the perio d from March 10 of 2013 to November 10 of 2013. The voucher for species of A. annua was deposited in the UFV herbarium under the identification VIC15592.
A. annua cv. Artemis was propagated through hybrid seeds resulting from plant breeding. The seedlings were grown in plastic cups with a volume of 300 mL using commercial substrate. After root- ing of the seedlings, the transplantation was carried
out in pots with a volume of 10 L kept within a greenhouse.
The experiment was installed in a completely randomized design in a factorial scheme (4 x 2), with three repetitions for extraction of essential oil. The plots consisted of a pot (10 L), with two plants. The plants were cultivated in four doses of fertili- zation (NPK): without fertilization (D0), 50% of the recommended dose (D1), recommended dose (D2), and 150% of the recommended dose (D3). The evaluations were carried out in two harvest times: 60 and 125 days after transplantation (DAT). The substrate used in the pots for plant cultivation was constituted by soil classified as Red Latosol Dystrophic (Santos et al., 2006), collected in the layer of 0-20 cm.
The sources of nitrogen, phosphorus, and potas- sium used were ammonium sulfate P.A. (21% N), simple superphosphate P.A. (18% P2O5), and potas- sium chloride P.A. (60% K2O), respectively. The doses of mineral fertilizer used in the experiment were the following (Kg pot -1): nitrogen = 0.0035 (D1), 0.007 (D2), 0.01 (D3); phosphorus = 0.02 (D1), 0.04 (D2), 0.06 (D3); potassium = 0.0015 (D1), 0.003 (D2), 0.0045 (D3).
Essential oil analysis
The leaves of A. annua were separated into three portions of 100 g. The essential oils from such por- tions were then extracted by hydrodistillation, for a period of two hours in triplicate, using a Clevenger - type apparatus. The oils were separated from the aqueous phase with pentane PA (C5H12). The or- ganic fractions obtained were pooled and dried over anhydrous magnesium sulfate, filtered, and the sol- vent removed under reduced pressure in a rotary evaporator at 40 °C.
The components of essential oils were analyzed by Shimadzu GCMS-QP5050A apparatus, equipped with a DB-5-fused silica column (30 m × 0.25 mm, film thickness of 0.25 μm) and coupled to a mass detector. The following chromatographic conditions were employed: Helium as carrier gas under a flow of 1.8 mL min-1; injector temperature of 220 °C; initial oven temperature of 40 °C, iso- thermal for 2 min., followed by heating at 3 °C min - 1 to 240 °C, then remaining isothermal for 15 min.; sample injection volume of 1.0 μL (10 mg mL-1 in dichloromethane); split ratio of 1:10; and column pressure of 100 kPa (Barbosa et al., 2012).
The quantification of the essential oil compo- nents was carried out with Shimadzu GC- 17A equipment fitted with a flame ionization detector (FID) and a SBP5-supelco-fused silica capillary column (30 m x 0.25 mm, film thickness of 0.25 μm). Chromatographic conditions were identical to
© 2019 Journal of Biotechnology and Biodiversity ISSN: 2179- 4804
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those used for CG-MS analyses, except for the fact that the carrier gas used was nitrogen.
The identification of essential oil components was performed through a comparison of their reten- tion indexes (RI) (Adams, 2007) relative to a stand- ard alkane series (C9-C27) as well as through com- parison of their mass spectrum with those available in the Nist library database (Maia & Andrade, 2009; Syarul et al., 2010).
Statistical analysis
The data of the essential oil content were sub- jected to variance and regression analysis. For qual-
itative fator (harvest times), the means were com- pared through the Tukey test and regression equa- tions were adjusted for the quantitative factor (doses of mineral fertilization). The regression equations were adjusted based on the "t" test of the coefficients at 5 or 1% probability and in the coef- ficient of determination. The analysis was per- formed in the MINITAB 17 computer system.
RESULTADOS E DISCUSSÃO
Essential oil contente
The analysis of variance for the variable essen- tial oil content is shown in table 1.
Table 1 - Analysis of variance for the variable essential oil content from Artemisia annua in two harvest times (Times) and four doses of mineral fertilization (doses).
SV DF SS MS F
Times 1 0.06827 0.068267 10.15**
Doses 3 0.50258 0.167528 24.91**
Times x doses 3 0.0894 0.0298 4.43**
Error 16 0.1076 0.006725
Total 23 0.76785
** significant at 1% probability (p < 0.01)
According to the analysis of variance, significant interaction was found (p < 0.01) among the factors harvest times and doses of mineral fertilization. Thus, unfolding of interaction “harvest times x doses of mineral fertilization” was performed to compare the levels of one factor within the levels
of the other factor. In the factor harvest times (qual- itative factor) the means were compared by Tukey test. In the factor doses of mineral fertilization (quantitative factor) were adjusted regression equa- tions (Table 2).
Table 2 - Mean values of essential oil content (%), regression equations, and coefficient of determination (r2) of A. annua, in four doses of mineral fertilization (D0, D1, D2 and D3) and two harvest times (60 and 125 days after transplantation- DAT). Viçosa-MG, 2017.
Doses of mineral fertilization
Harvest times D0 D1 D2 D3 Regression equations r2 (%)
60 DAT 0.81a 0.60 a 0.59 a 0.39 a y = 0.915 - 0.1277 **d 69.44
125 DAT 0.54b 0.63 a 0.58 a 0.21a y = 0.6447 - 0.2073* d 46.39
Means followed by the same letter in the column do not differ by Tukey test (P > 0.05). ** = significant at 1% probability by the “t” test (P < 0.01); or * = significant at 5% probability by the “t” test (P < 0.05).
The essential oil contents in the two harvest times varied from 0.21% to 0.81% m/m. Significant difference (P < 0.05) in the essential oil content only was observed for the dose D0, where the first harvest time presented value (0.81) statistically higher than the value of second harvest (0.54) (Ta- ble 02).
A tendency of decrease in the essential oil con- tent was observed as the dose of NPK increased, according to the adjusted regression equations in both harvests. The adjusted linear regression model
presented a negative angular coefficient, indicating that with the increase of the dose of mineral fertili- zation, there was reduction in the essential oil con- tent (Table 2).
It is worth emphasizing that the essential oil con- tent in the plant can be influenced by the time of collection and the stage of development of the plant, because during the growth phase there is a greater demand for nutrients. In this present study, was observed an increase of average value of essen- tial oil content in the first harvest time (60 DAT)
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compared to the second harvest considering the four doses of fertilization.
The application of fertilizers to aromatic plants usually affects the production of essential oils (Nurzynska-Wierdak, 2013). Thus, an evaluation of the requirements of each species and the appro- priate management of fertilization are necessary (Martins et al., 2007; Seixas et al., 2013).
Identification of chemical constituents
The qualitative analysis of the constituents of the essential oils was performed by GC-MS. The com- pounds identification was carried out comparison with data found in the mass spectra databases and by their retention indexes (Tables 03 and 04) (Ad- ams, 2007).
Table 3 - Major components of the essential oils from A. annua at first harvest time (60 days after transplan- tation) and four doses of mineral fertilization
Major components
RIc a
RI b
D0
D1 D2 Relative peak áreas (%) c
D3
1,8- cineole 1027 1026 2.37±0.03 2.37±0.05 2.00±0.05 2.08 ±0.02
Camphor 1144 1141 tr tr 26.56±0.03 26.70± 0.03
Pinocarvone 1160 1160 tr tr Tr 2.33 ± 0.00
Borneol 1164 1165 33.07±0.12 33.08±0.15 1.84±0.01 tr
Terpinen-4-ol 1150 1174 3.32 ± 0.03 3.33 ± 0.09 tr tr
(E)-Caryophyllene 1417 1417 6.06 ± 0.02 6.06 ± 0.02 6.16±0.02 7.39 ± 0.12
(E)-β-Farnesene 1458 1454 4.99 ± 0.15 4.99 ± 0.01 5.99±0.08 5.41 ± 0.23
β-Chamigrene 1475 1476 tr tr tr -
α-Amorphene 1482 1483 tr tr 21.99±0.41 21.93± 0.13
Germacrene D 1482 1484 18.28±0.58 18.28±0.06 1.66±0.05 1.61 ± 0.01
Bicyclogermacrene 1495 1500 1.34 ± 0.25 1.34 ± 0.00 0.56±0.00 0.27 ± 0.02
Caryophyllenyl alcohol 1575 1570 2.44 ± 0.02 2.44 ± 0.02 3.15±0.05 2.78 ± 0.03
allo-Aromadendrene epoxide 1630 1638 tr tr 2.20±0.00 2.10 ± 0.02
1-epi-Cubenol 1624 1627 tr tr 2.82±0.00 1.71 ± 0.02
β-Cedren-9-one 1630 1630 1.78 ± 0.25 1.78 ± 0.05 tr tr
epi-α-Cadinol 1646 1638 1.64 ± 0.01 1.64 ± 0.02 2.20± 0.12 tr
α-Bisabolol 1687 1685 1.51 ± 0.04 1.51 ± 0.01 1.78 ± 0.02 0.34 ± 0.00
Identified (%) 77.43 76.82 78.91 74.65
a calculated retention index; b retention index described in the literature (Adams 2007); c All values reported as an average of three replicates; tr – trace
compound (less than 1.0%); D0: without fertilization; D1: 50% of the recommended dose; D2: recommended dose; D3: 150% of the reco mmended dose.
Table 4 - Major components of the essential oils from A. annua at second harvest time (125 days after trans- plantation) and four doses of mineral fertilization .
Major components
RIc a
RI b
D0
D1 D2 Relative peak áreas (%) c
D3
1,8- cineole 1027 1026 0.90±0.02 2.37±0.06 2.87±0.02 4.05±0.00
Camphor 1144 1141 14.72±0.02 32.72±0.08 31.80±1.23 56.79±0.28
Pinocarvone 1160 1160 tr tr tr 7.54 ± 0.05
Borneol 1164 1165 0.96 ± 0.02 1.92 ± 0.05 0.94 ± 0.01 tr
Terpinen-4-ol 1150 1174 tr tr tr 1.91 ± 0.06
(E)-Caryophyllene 1417 1417 5.48 ± 0.05 7.91 ± 0.01 7.79 ± 0.85 3.71 ± 0.03
(E)-β-Farnesene 1458 1454 4.02 ± 0.00 4.45 ± 0.02 5.16 ± 0.84 2.47 ± 0.00
β-Chamigrene 1475 1476 tr 2.04 ± 0.21 2.01 ± 0.02 7.67 ± 0.15
α-Amorphene 1482 1483 16.54± 0.33 tr tr 0.69 ± 0.00
Germacrene D 1482 1484 1.59 ± 0.00 19.68±0.41 20.99±0.12 0.56 ± 0.00
Bicyclogermacrene 1495 1500 0.43 ± 0.00 2.25 ± 0.01 2.64 ± 0.03 0.73 ± 0.02
Caryophyllenyl alcohol 1575 1570 2.20 ± 0.02 2.59 ± 0.02 2.22 ± 0.02 1.08 ± 0.00
allo-Aromadendrene epoxide 1630 1638 tr tr tr 0.77 ± 0.05
1-epi-Cubenol 1624 1627 1.49 ± 0.01 1.77 ± 0.23 1.46 ± 0.25 0.48 ± 0.00
β-Cedren-9-one 1630 1630 1.51 ± 0.01 2.07 ± 0.63 1.87 ± 0.21 tr
epi-α-Cadinol 1646 1638 1.40 ± 0.01 0.81 ± 0.32 0.68 ± 0.14 tr
α-Bisabolol 1687 1685 34.44±0.24 1.43 ± 0.01 1.05 ± 0.00 tr
Identified (%) 86.68 82.01 81.48 88.45
a calculated retention index; b retention index described in the literature (Adams 2007); c All values reported as an average of three replicates; tr – trace compound (less than 1.0%); D0: without fertilization; D1: 50% of the recommended dose; D2: recommended dose; D3: 150% of the reco mmended
dose.
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In the essential oils extracted from A. annua, a total of 17 components were identified with the ma- jor components shown in Table 03 and 04. The monoterpenes camphor and borneol were the major constituents in the oils of A. annua. In the first har- vest, using doses D0 and D1, the presence of cam- phor not was observed, while in the second harvest using dose D3, 56.79% of camphor was detected. This variation in the camphor content indicates that in this species an increase of the dose of fertiliza- tion NPK favored an increase in the camphor con- tent and that this increase was more pronounced during the second harvest.
The sesquiterpenes germacrene D and α- amor- phene were also identified in high concentrations in the oils from plants of both harvesting times. The
increase in NPK fertilization did not favor the in- crease of α-amorphene and germacrene D contents. The variation in the content of these compounds oc- curred at random in the oils from the two harvesting (60 and 125 DAT). The highest content of ger- macrene D was 20.99% for plants submitted in the D2 treatments at 125 DAT (Figure 01). The α - amorphene compound had its highest concentration in the essential oil when the plants were submitted to treatment D2 at 60 DAT, at 21.99%. The sesquit- erpene α-bisabolol was found in small quantities (<2%) in almost all samples, except in the oil ob- tained from plants subjected to D0 treatment and harvested at 125 DAT, which presented 34.44% of this compound (Table 03 and 04).
Figure 1 - Chromatogram of the essential oil from leaves of Artemisia annua with dose NPK (D2) at 125 days after transplantation. 1: 1,8-cineole (2,87%); 2: camphor (31,80%); 3: E-caryophyllene (7,79%); 4: (E)-β- far- nesene (5,16%); 5: Germacrene D (20,99%)
Judging from the results obtained, this species can be used as a source of borneol or camphor, de- pending on the dosage used during fertilization and the time of harvest. Such compounds are important, considering that borneol derived from pine oil is used as a disinfectant and deodorant. Camphor has application as an anesthetic, expectorant, and an- tipruritic. In fact, considering that α-bisabolol has been reported to have several biological activities, including anti-inflammatory, antimicrobial, and leishmanicidal (Lopez et al., 2015), the results re- ported here are also relevant considering that this plant can be cultivated under controlled conditions to maximize the production of this important ses- quiterpene.
Geranyl diphosphate is a precursor compound of
monoterpenes and may produce 1,8-cineole, sab- inene, sabinene hydrate, linalool, and limonene, by means of enzymatic reactions (Figure 02). The in- terconversion of the components is determined ge- netically and can be affected by agronomic factors and the stage of plant development. For example, is it apparent from Table 03 that at D1 and 60 DAT, the oil is rich in borneol and has no camphor. After another 65 days of cultivation (125 DAT) under the same fertilization procedure, the borneol content decreases to 1.92% while camphor yield is 32.72% (Table 04) (Figure 02). The oxidation of borneol as the plant matures can explain this variation. Such variation can also be explained considering Figure 02, where the intermediate cation 3 can generate in one way compounds 7-9 in competition to 4- 6.
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Figure 2 - Biosynthetic routes for the formation of the main components of Artemisia oils. 1: Geranyl-OPP; 2: Neryl-OPP; 3: Terpenylic cation; 4: 1,8-Cineole; 5: Borneol; 6: Camphor; 7: β-pinene; 8: Pinocampheol; 9: trans-Thujone; 10: Farnesyl-OPP; 11: α-Bisabolol; 12: Germacrenylic cation; 13: Germacrenylic cation rear- ranged; 14: Germacrene D; 15: Germacrene D-4-ol; 16: α- Amorphene.
Some of the variation in the chemical composi- tion may be related to potassium (K), because it is involved in the synthesis of aromatic compounds through the activation of several enzymes. The con- ditions which led to the increase in the concentra- tion of this nutrient may have provoked stimulation in the enzymatic activities, consequently altering the composition of the oils (Garlet et al., 2007). The study of essential oil of Artemisia species is important for the characterization of the genetic re- sources which are conductive to the selection of species. The knowledge of these genetic character- istics in the plant of interest as well as information pertaining to the cultivation environment contrib- utes to the selection of genotypes that are more adapted to specific habitats (Castro et al., 2016; Camêlo et al., 2011; Nascimento et al., 2011).
In this sense, biotic and abiotic factors, including genetic variation, plant nutrition, geographic loca- tion, seasonal variations, and stress during growth or maturity, influence the yield and composition of the essential oil and its biological properties (Raut & Karuppayil, 2014).
CONCLUSIONS
The highest essential oil content in A. annua (0.81%) was observed in the D0 treatment at 60
DAT, while the lowest oil content (0.21%) was found in the D3 treatment at 125 DAT. Significant difference (P < 0.05) in the essential oil content only was observed for the dose D0.
For A. annua the increase of the dose of mineral fertilization indicated a disadvantage with the re- duction of the essential oil content in the two har- vesting times. Therefore, the increase of NPK ferti- lization dose did not increase the essential oil con- tent of A. annua and is not an advantage for this purpose.
In general, the variation of the composition of the essential oil under greenhouse conditions, in two harvesting times (60 and 125 DAT) and using four doses of mineral fertilization, occurred at ran- dom.
The results indicate that A. annua could be an al- ternative source of borneol and camphor, biological active component with use in the chemical and pharmaceutical industry.
The effect of NPK fertilization on the composi- tion of the essential oil of A. annua requires devel- opment of other studies, taking into account that the production of secondary metabolites is not always stimulated with NPK fertilization due to the influ- ence of physiological factors and the genetic con- stitution of the plant.
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ACKNOWLEDGEMENTS
We are grateful to the following Brazilian agen- cies: Conselho Nacional de Desenvolvimento Cien- tífico e Tecnológico (CNPq) for research fel-
lowships (AJD, LCAB, MCP); Fundação de Am- paro à Pesquisa de Minas Gerais (FAPEMIG) for
financial support and Coordenação de Aperfeiçoa- mento de Pessoal de Nível Superior (CAPES) for research fellowship (PTLS).
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