Universidade Federal de Santa Maria
Ci. e nat., Santa Maria, V. 41, e45, 2019
DOI: http://dx.doi.org/10.5902/2179460X40405
Received: 07/10/2019 Accepted: 21/10/2019
Chemestry
Essential oil yield and composition of native species of the Myrtaceae family from “Campos Gerais” of the Atlantic Forest in Parana State
Luiz Everson Da SilvaI
Wanderlei do AmaralII
Cícero DeschampsIII
Luiz Antonio BiasiIV
Humberto Ribeiro BizzoV
Marco Antonio Silva PintoVI
I Professor associado da Universidade Federal do Paraná - luiz_everson@yahoo.de
II Doutor em Ciências Agrárias. Universidade Federal do Paraná - wdoamaral@hotmail.com
III Doutor em Fisiologia Vegetal e Biologia Molecular. Professor Associado da Universidade Federal do Paraná - cicero@ufpr.br
IV Doutor em Agronomia. Professor titular da Universidade Federal do Paraná - biasi@ufpr.br
V Pesquisador da EMBRAPA - bizzo@ctaa.embrapa.br
VI Analista da EMBRAPA - luiever@gmail.com
Abstract
The Myrtaceae family has great occurrence in Brazil, mainly in the Atlantic Forest of the South and Southeast regions and presents potential for essential oil production. This work aimed to evaluate the essential oil yield and composition of the species Myrciaria delicatula, Campomanesia xantocarpha, Campomanesia aurea, Calyptranthes clusiifolia, Myrcia splendens, Eugenia osoriana, Myrciaria tenella, Myrceugenia reitzii, Calyptranthes concinna e Myrcia arborensis from a segment of the Atlantic Forest of Parana State. The sample collections for essential oil extraction, photographic records and herbarium specimens preparation for botanical species identification were made at the Private Reserve of Natural Heritage (PRNP) Butuguara in Palmeira (PR), with “Campos Gerais” formations. The identification and the official deposit of the species were made at the HFIE Herbarium. The essential oil extraction was carried out by hydrodistillation of fresh and dried leaves using a Clevenger type apparatus and the chemical composition was analyzed by gas phase chromatography coupled with mass spectrometry (GC/MS). Myrceugenia reitzii showed essential oil yield superior to other species and the essential oil yield of all species increased after drying. The chemical composition in the samples showed mono and sesquiterpenes, being the sesquiterpenes in higher percentages. The drying conditions affected the essential oil composition of the for the majority of the evaluated species.
Keywords: Medicinal and Aromatic Plants, Terpenes, Atlantic Rain Forest
1 Introduction
The study of the diversity and complexity of chemical structures found in nature provides important tools for molecular biology, biochemistry, medicine and ecological chemistry. Essential oils are complex mixtures of volatile substances, lipophilic, usually odoriferous and liquid [1], widely used to impart aroma and flavors to food products and oral hygiene, perfumery and cleaning products. They are also sources of active principles for the pharmaceutical industry [2-5]. The essential oils in plants are related to ecological functions of defense and attraction of pollinators among others, and undergo quantitative and qualitative variation in response to environmental conditions [6].
In Brazil, the production of essential oils does not meet the demand, besides, the national and international perfumery market has been showing interest in new essences [7-8]. According to Bandoni [9] it is estimated that approximately 65% of the market of essences comes from cultivated species and 1% from wild species. Yunes [5], defends the importance of intensifying the studies of the Brazilian flora, in an interdisciplinary way, aiming at the identification of promising species for the production of volatile oils, for use as inputs in obtaining chemical entities to be included in new medicines available to the Health system
Besides, Brazil has more than 43 thousand described plant species, with an endemism rate of 56%, and the Atlantic Forest Biome presents the largest number of plant species among Brazilian biomes, with more than 19,000 species, of which 7,600 species are endemic [10]. On the other hand, the general fields have a very particular structure, function and dynamics and represent a highly interactive ecosystem [11], whose existence is conditioned by abiotic factors, anthropic action and natural disturbances such as frost, specially the fire [12]. These changes in environmental factors influence the secondary metabolism of plant species and consequently the production and composition of the essential oils [13]. Post-harvest factors, such as drying, also affect the production of essential oil in aromatic species. Myrtaceae is one of the most important botanical families in Brazil, especially in the Atlantic Forest, mainly with 642 species in the South and Southeast regions [10], with great potential in the production of volatile oils of economic interest [16]. It is also known for its important role in the phytosociology of South and Southeastern Brazil Forests [17-18], being one of the predominant groups of the arboreal component of the Atlantic Forest [19-20]. Species of this family are used by the population for medicinal purposes, where they are used mainly in the treatment of gastrointestinal disorders and infectious states [21].Gubert evaluated the content and composition of aromatic species of the family Myrtaceae in the coastal region of Paraná State, observing the presence of constituents of mono and sesquiterpene classes. There are several floristic and structural studies for the Atlantic Forest Biome, but the native aromatic flora, especially the Campos Gerais of the State of Paraná, is little known. In this work, the content and chemical composition of the essential oil of samples of fresh and dried leaves of native species of the family Myrtaceae in the Campos Gerais of the Atlantic Forest of the State of Paraná were evaluated.
2 Material and Methods
2.1 Plant material collection and identification
The plant material used for essential oil extraction consisted of leaves, which were collected in the "Private Natural Heritage Reserve Butuguara" (PRNP), a segment of the Atlantic Forest of Parana state, South of Brazil. This area is located at 25 º 20.884 'S and 049 ° 47.258' W, with altitudes ranging from 985-1145 meters and soil classified as Cambissol and Lithosol and the climate as “Cfb”, with annual average temperatures around 17 ° C, frequent frosts and rainfall of 1,200 mm year. Collection and transport of plant material in the reserve were made under license of the Environmental Institute of Parana (Number 284/11). Ten species were collected based on the aroma and the botanical group with aromatic characteristics mentioned in the literature (Table 1). Individual species location was georeferenced and photographic records for identification were made. The dried specimens were transported to the Herbarium of the “Faculdades Integradas Espírita (HFIE)”, where it were herborized. Duplicates were sent to “Curitiba Bothanic Museum (MBM)” and Federal University of Parana (UPCB) herbariums. Samples of approximately 1 kg of leaves and terminal branches were randomly collected from at least 10 plants of each species. The dried samples were obtained after maintaining the plant material at 40° C for 24 hours in an electric dryer (FANEM – Mod. 320 SE) with air circulation.
Table 1 - General Data of Myrtaceae Native Species Family Collected, Palmeira, PR, 2011/2012
|
Scientific Name |
Voucher* |
Localization** |
|
Collection date |
|
|
Latitude |
Longitude |
Altitude |
|||
|
Myrciaria delicatula (DC.) O. Berg |
8.425 |
S 25° 21.095' |
W 49° 47.896’ |
1.078 |
14/05/11 |
|
Campomanesia xantocarpha O. Berg. |
8.821 |
S 25° 21.094' |
W 49° 47.897’ |
1.085 |
14/05/11 |
|
Campomanesia aurea O. Berg. |
8.254 |
S 25º 20. 444’ |
W 49º 48.052’ |
1.063 |
14/02/11 |
|
Calyptranthes clusiifolia O. Berg |
8.816 |
S 25° 19.982' |
W 49° 48.371’ |
1.018 |
27/09/11 |
|
Myrcia splendens (Sw.) DC. |
8.817 |
S 25° 19.982' |
W 49° 48.371’ |
1.018 |
27/09/11 |
|
Eugenia osoriana Mattos & D. Legrand |
9.011 |
S 25° 20.938' |
W 49° 47.141’ |
1.140 |
25/02/12 |
|
Myrciaria tenella (D.C) O. Berg |
8.999 |
S 25° 19.885' |
W 49° 48.284’ |
1.019 |
17/10/11 |
|
Myrceugenia reitzii D. Legrand |
9.020 |
S 25° 20.958' |
W 49° 47.132’ |
1.065 |
04/02/12 |
|
Calyptranthes concinna DC. |
9.007 |
S 25° 20.953' |
W 49° 47.077’ |
1.124 |
25/02/12 |
|
Myrcia arborensis O. Berg |
9.012 |
S 25° 20.947' |
W 49° 47.127’ |
1.140 |
25/02/12 |
* Number of the specimen for the identified exsicata, as found in the HFIE Herbarium of the FIES in Curitiba, PR
** Coordinates of collection of the species, this presents an average error of 15 m distance to the environment of the point
Essential oil isolation
The essential oil samples were obtained by hydrodistillation during 4 hours and 30 minutes in a Clevenger type apparatus using 100 g of fresh or 50 g of dried plant material in 1 L of distilled water, with 3 replications. After extraction, the essential oil samples were maintained in the freezer until the analysis.
Essential oil analysis
The identification of the essential oil chemical constituents was made by gas phase chromatography coupled to mass spectrometry (GC/MS). The samples were diluted in dichloromethane in the proportion of 1% and 1.0 mL of the solution was injected with a flow division of 1:20 in an Agilent 6890 chromatograph (Palo Alto, CA) coupled to mass selective detector Agilent 5973N. The injector was maintained at 250° C. The separation of the constituents was obtained in the HP- 5MS capillary column (5% phenyl -95 % - dimethylpolysiloxane, 30 m × 0.25 mm × 0.25 µm) and using helium as carrier gas (1.0 mL min-1). The oven temperature was programmed from 60 to 240 °C at a rate of 3 °C min- 1. The mass detector was operated in electron ionization mode (70 eV) at a rate of 3.15 min-1 scan and mass range of 40 to 450 u. The transfer line was maintained at 260 °C, the ion source at 230° C and the analyzer (quadrupole) at 150° C.
The diluted samples were injected into an Agilent 7890A chromatograph equipped with flame ionization detector (FID), operated at 280° C for quantification. The same column and analytical conditions described above were employed, except for the carrier gas used, which was hydrogen at a flow rate of 1.5 mL min- 1. The percentage composition was obtained by electronic integration of the FID signal by dividing the area of each component by the total area (area %). The constituents identification was obtained by comparing their mass spectra with those of Wiley library (Wiley, 1994; NIST, 2013 [23-24] and also with their linear retention indices which were calculated from injection of a homologous series of hydrocarbons (C7 - C26) and compared with literature data [25].
Data analysis
Variances were tested for homogeneity using the Bartlett's test and the the Scott - Knott test (P<0.05) for mean comparison procedures were performed using the statistical software “ASSISTAT”, release 7.6 Beta [26].
3 Results and Discussion
Essential oil yield
There was no significant interaction between the species and drying factors, but there was a significant difference in the essential oil content among the species (Table 2). The Myrceugenia reitzii species had a higher average essential oil content (1.59%), while the others had a mean essential oil content of 0.02 to 0.19%. The only species that did not show essential oil after hydrodistillation extraction was Myrcia arborensis. The species Myrcia splendens presented essential oil only in fresh leaves, whereas Campomanesia xantocarpha only after drying (Table 2). Table 2 - Essential oil content (%) of leaves of native species of the Myrtaceae family in the Campos Gerais of the Atlantic Rain Forest of the Paraná State, South of Brazil.
|
Species |
Oil yield |
|
Campomanesia aurea O. Berg. |
0,17 b |
|
Campomanesia xantocarpha O. Berg. |
0,02 d |
|
Myrciaria delicatula (DC.) O. Berg |
0,19 b |
|
Calyptranthes clusiifolia O. Berg |
0,15 b |
|
Calyptranthes concinna DC. |
0,16 b |
|
Myrcia splendens (Sw.) DC. |
0,01 e |
|
Eugenia osoriana Mattos & D. Legrand |
0,19 b |
|
Myrciaria tenella (D.C) O. Berg |
0,08 c |
|
Myrceugenia reitzii D. Legrand |
1,59 a |
|
Myrcia arborensis O. Berg |
- |
|
CV% |
26,28 |
**The averages followed by the same lowercase letter in the column and uppercase letter in the row do not differ statistically by the Scott-Knott test at 5% probability.
Besides the difference between the species, there was also drying effect on the essential oil content of the species, being higher after drying (Table 3). Assis [27] also observed in Eugenia uniflora (Myrtaceae) the increase in the essential oil content after the drying of the leaves. In this family, the essential oil is stored in secretory cavities and leaf parenchyma cells [28-29]. With the drying there was water release and rupture in plant tissues, which may have contributed to the extraction of the essential oil. Gubert [22] evaluating essential oil contents of fresh leaves of Campomanesia xantocarpha and Myrceugenia reitzii in the coast of Pará found levels of 0.01 and 0.04%, respectively. These contents were lower than those found in Campos Gerais Paraná region (Table 2), but the C. xantocarpha species collected in Campos Gerais only showed essential oil after drying the leaves. Lima [30] evaluating Myrtaceae species in the cerrado of Botucatu (SP), found in the dry leaves of Myrcia splendens contents of 0.24%. In this work, the species Myrcia splendens only presented essential oil in fresh leaves (0.02%), well below that found in Botucatu (SP). Table 3 - Average content of essential oil (%) in fresh and dried leaves of native species of the family Myrtaceae in the Campos Gerais of the State of Paraná.
|
Samples |
Oil Yield |
|
Fresh |
0,27 b |
|
Dried |
0,32 a |
**The averages followed by the same lowercase letter in the column and uppercase letter in the row do not differ statistically by the Scott-Knott test at 5% probability.
Essential oil Composition
101 constituents were identified in the essential oil samples of fresh and dry leaves, corresponding to the identification of 81% of the constituents (Table 4). These samples presented 18.3% and 15.0% monoterpenes, 2.2% and 3.1% oxygenated monoterpenes, 17.2% and 15.0% sesquiterpenes, 42.0% and 40.8% of oxygenated sesquiterpenes in the samples in fresh and dry leaf samples, respectively. The species Myrciaria delicatula, Campomanesia aurea, Calyptranthes clusiifolia, Myrciaria tenella and Calyptranthes concinna were predominantly sesquiterpenes. The species Campomanesia xantocarpha, Eugenia osoriana and Myrcia splendens presented only sesquiterpenes in their composition and only the species Myrceugenia reitzii presented a higher percentage of monoterpenes in the essential oil samples. The major constituent in the samples of essential oils obtained from fresh leaves of Myrciaria delicatula were α-pinene (24.9%) and α-cadinol (10.3%), in contrast with, khusimol (11.7%) and epi-zizanone ( 8,7%) in Campomanesia aurea, α-pinene (13.7%) and β-pinene (10.1%) in Calyptranthes clusiifolia, α-pinene (20.5%) and (E) -β-caryophyllene (17.2%) in Myrciaria tenella, β-pinene (30.9%) and α-pinene (27.8%) in Myrceugenia reitzii, α-cadinol (27.9%) and globulol (16.1%) (17.9%) and α-cadinol (8.5%) in Calyptranthes concinna and globulol (16.7%) and viridiflorol (10.1%) in Myrcia splendens.The species Calyptranthes clusiifolia and Eugenia osoriana after drying maintained their chemical composition stable in relation to their major compounds (Table 4). Other species have undergone more significant changes, such as Myrciaria delicatula, which presented a decrease in the percentage of α-pinene from 24.9% to 11.2% and α-cadinol from 10.3% to 8.5%, showing only after drying Khusimol (10.6%) and vetivenic acid (11.8%). The species Campomanesia aurea after drying did not present khusimol and epi-zizanone, but mustacona (9.9%) and caryophyllene oxide (9.2%). The species Myrciaria tenella decreased the percentage of α-pinene from 20.5% to 14.6% and from (E) -β-caryophyllene from 17.2% to 9.7%, showing only after drying the safrole constituent ( 7.3%). The composition of the essential oil of M. reitzii on the coast of Paraná presented as major components spatulenol (22.8%) and globulol (16.8%) [21], whereas in Campos Gerais - Paraná the species did not present globulol, as major components but α-pinene (27.8%) and β-pinene (30.9%) (Table 4). Lima [30] found in the cerrado of Botucatu (SP) for Myrcia splendens the major components β-pinene (12.21%) and ortho-cimene (11.09%), presenting a higher percentage of monoterpenes. In the Campos Gerais, the majority of the species presented globulol (16.7%) and viridiflorol (10.1%), with a higher percentage of sesquiterpenes, differing from the results found in the state of. It is considered that several environmental genetic factors may have influenced the composition of the essential oils in these species [13]. With respect to the potential use of these oils we can highlight from the main components. Some of the main compounds described are interesting for biological assays. Spathulenol, for example, has quite a moderate activity against most of the tested strains of human carcinogenic cells and it demonstrated significant repellent activity against Aedes aegypti and A. stephensi. On the other hand, several biological activities are attributed to β-caryophyllene, such as anti-inflammatory, antibiotic, antioxidant, anticarcinogenic and local anaesthetic activities. Elimicin molecule was responsible for the antibacterial activity. Safrole has been used as starting material in the synthesis of analogues which active as germination stimulant [14].
Table 4 Relative percentage of the chemical components in the essential oil from fresh and dried samples of native Myrtaceae Family of the Campos Gerais of the Paraná State Atlantic Forest, 2012.
|
Compounds |
|
|
Speciesc |
||||||||
|
M. deli |
C. aure |
C. xanto |
C. clusi |
M. tene |
M. reit |
E. osor |
C. conc |
M. sple |
|||
|
IRa |
IRb |
|
|
|
|
|
|
|
|
|
|
|
α-tujeno |
925 |
924 |
--- |
--- |
--- |
0,5 (0,5) |
--- |
--- |
--- |
0,2 (0,3) |
--- |
|
α-pinene |
937 |
932 |
24,9 (11,2)d |
--- |
--- |
13,7 (14,2) |
20,5 (14,6) |
27,8 (21,1) |
--- |
6,6 (9,5) |
--- |
|
Sabinene |
972 |
969 |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
0,6 (0,8) |
--- |
|
β-pinene |
975 |
974 |
--- |
--- |
--- |
10,1 (9,7) |
1,0 (0,8) |
30,9 (22,5) |
--- |
6,2 (9,1) |
--- |
|
Myrcene |
990 |
988 |
--- |
--- |
--- |
1,7 (1,6) |
--- |
1,1 (0,6) |
--- |
1,6 (2,4) |
--- |
|
α-felandreno |
1005 |
1002 |
--- |
--- |
--- |
0,8 (0,8) |
--- |
--- |
--- |
(0,3) |
--- |
|
δ-3-carene |
1009 |
1011 |
--- |
--- |
--- |
--- |
1,3 (1,3) |
--- |
--- |
--- |
--- |
|
α-terpinene |
1016 |
1018 |
--- |
--- |
--- |
0,4 (0,4) |
--- |
--- |
--- |
(0,2) |
--- |
|
p-cymene |
1023 |
1022 |
--- |
--- |
--- |
0,4 (0,4) |
--- |
--- |
--- |
0,9 (0,6) |
--- |
|
Limonene |
1027 |
1024 |
--- |
1,6 |
--- |
5,0 (4,8) |
2,4 (2,3) |
2,2 (1,5) |
--- |
3,3 (4,5) |
--- |
|
1,8-cineole |
1029 |
1030 |
--- |
--- |
--- |
1,3 (1,6) |
--- |
--- |
--- |
--- |
--- |
|
γ- terpinene |
1056 |
1054 |
--- |
--- |
--- |
0,9 (0,9) |
--- |
--- |
--- |
0,2 (0,3) |
--- |
|
Terpinolene |
1086 |
1088 |
--- |
0,6 |
--- |
0,4 |
0,5 (1,8) |
--- |
--- |
--- |
--- |
|
α-pinene oxide |
1099 |
1099 |
--- |
--- |
--- |
--- |
--- |
0,6 (1,0) |
--- |
--- |
--- |
|
Linalol |
1100 |
1095 |
2,5 |
--- |
--- |
1,0 (1,0) |
--- |
--- |
--- |
--- |
--- |
|
trans-pinocarveol |
1136 |
1135 |
--- |
--- |
--- |
--- |
--- |
(2,8) |
--- |
--- |
--- |
|
Pinocarvone |
1161 |
1160 |
--- |
--- |
--- |
--- |
--- |
1,8 (2,8) |
--- |
--- |
--- |
|
4-terpineol |
1178 |
1174 |
--- |
--- |
--- |
1,7 (1,6) |
--- |
--- |
--- |
1,9 (1,3) |
--- |
|
α-terpineol |
1190 |
1186 |
--- |
--- |
--- |
1,3 (1,4) |
--- |
4,3 (3,9) |
--- |
--- |
--- |
|
Mirtenal |
1196 |
1195 |
--- |
--- |
--- |
--- |
--- |
1,5 (1,5) |
--- |
--- |
--- |
|
Verbenone |
1208 |
1204 |
--- |
--- |
--- |
--- |
--- |
1,5 (1,9) |
--- |
--- |
--- |
|
Sabine trans-hydrate acetate |
1252 |
1253 |
--- |
--- |
--- |
--- |
0,6 (0,3) |
--- |
--- |
--- |
--- |
|
Safrole |
1285 |
1285 |
--- |
--- |
--- |
--- |
(7,3) |
--- |
--- |
--- |
--- |
|
α-copaene |
1371 |
1374 |
--- |
--- |
--- |
--- |
0,7 (0,3) |
(0,4) |
--- |
0,5 (0,3) |
--- |
|
β-elemene |
1391 |
1389 |
1,2 |
0,9 |
--- |
--- |
--- |
--- |
3,7 (2,9) |
0,9 (0,3) |
--- |
|
α-gurjunene |
1401 |
1409 |
--- |
--- |
--- |
--- |
0,7 (0,3) |
--- |
--- |
0,5 |
--- |
|
(E)-β-caryophyllene |
1417 |
1417 |
3,5 (1,6) |
5,1 (7,2) |
(2,7) |
6,7 (5,7) |
17,2 (9,7) |
1,3 (0,5) |
4,1 (7,8) |
1,8 (1,1) |
5,6 |
|
β-copaene |
1430 |
1430 |
--- |
--- |
--- |
1,0 (0,7) |
--- |
2,0 (0,5) |
1,3 (1,5) |
1,2 (0,3) |
--- |
|
Aromadendreno |
1435 |
|
--- |
(1,0) |
--- |
1,8 (1,4) |
2,5 (1,5) |
--- |
--- |
--- |
--- |
|
α-humulene |
1450 |
1452 |
1,1 (0,9) |
1,4 (1,2) |
(1,1) |
1,9 (1,3) |
2,9 (1,7) |
0,6 (0,7) |
1,0 (1,5) |
0,6 (0,3) |
--- |
|
Allo-aromadendreno |
1454 |
1458 |
--- |
0,7 (0,9) |
--- |
--- |
1,0 (0,4) |
--- |
(0,5) |
0,9 (0,4) |
--- |
|
4,5-di-epi-aristolochene |
1465 |
1471 |
--- |
--- |
--- |
--- |
(0,7) |
--- |
--- |
--- |
--- |
|
γ-muurolene |
1474 |
1478 |
--- |
(1,8) |
--- |
0,9 (0,6) |
--- |
(0,5) |
1,5 (1,9) |
0,5 |
3,1 |
|
Ar-curcumene |
1480 |
1479 |
--- |
--- |
--- |
--- |
--- |
--- |
4,2 (5,0) |
--- |
2,2 |
|
γ-curcumene |
1481 |
1481 |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
6,1 |
|
Germacreno D |
1482 |
1484 |
1,4 (0,9) |
(1,0) |
(2.3) |
--- |
--- |
--- |
--- |
1,4 (1,4) |
--- |
|
β-selinene |
1483 |
1489 |
1,3 (1,3) |
3,4 (1,8) |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
|
cis-β-guaiene |
1492 |
1492 |
--- |
--- |
--- |
--- |
--- |
0,5 |
2,9 (5,3) |
7,4 (4,0) |
--- |
|
Bicyclogermacrene |
1493 |
1494 |
2,8 (1,4) |
3,8 (5,6) |
(5,1) |
2,3 (1,6) |
3,7 (4,0) |
--- |
(1,1) |
0,7 (0,3) |
--- |
|
Viridiflorene |
1497 |
1496 |
--- |
--- |
--- |
--- |
--- |
--- |
(0,5) |
--- |
--- |
|
α-muurolene |
1498 |
1500 |
1,0 |
--- |
--- |
0,8 |
--- |
--- |
(0,8) |
--- |
--- |
|
δ-amorphene |
1504 |
1511 |
--- |
--- |
--- |
0,9 |
--- |
--- |
--- |
--- |
--- |
|
γ-cadinene |
1509 |
1513 |
--- |
(1,6) |
(1,4) |
0,9 (0,7) |
--- |
--- |
(1,5) |
4,5 (2,7) |
--- |
|
Cubebol |
1509 |
1514 |
--- |
--- |
--- |
--- |
(0,4) |
--- |
--- |
--- |
--- |
|
trans-calamenene |
1518 |
1521 |
--- |
--- |
--- |
--- |
4,4 (2,4) |
--- |
--- |
--- |
--- |
|
δ-cadineneo |
1520 |
1522 |
1,2 (0,8) |
3,0 (3,2) |
(3,7) |
3,4 (2,7) |
(0,3) |
--- |
--- |
--- |
2,7 |
|
trans-1,4-cadinadiene |
1527 |
1533 |
--- |
--- |
--- |
0,9 |
--- |
--- |
--- |
--- |
--- |
|
α-calacorene |
1541 |
1544 |
--- |
--- |
--- |
1,2 (1,2) |
--- |
--- |
--- |
--- |
--- |
|
Dracunculifoliol |
1541 |
1541 |
--- |
1,3 |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
|
Elemol |
1549 |
1548 |
--- |
--- |
--- |
--- |
--- |
0,8 (1,1) |
--- |
--- |
--- |
|
Elemicin |
1553 |
1555 |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
17,9 (22,9) |
--- |
|
Germacreno B |
1555 |
1559 |
--- |
(2,0) |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
|
Geranoyl Butanoate |
1559 |
1562 |
--- |
--- |
--- |
--- |
2,6 (1,4) |
--- |
--- |
--- |
--- |
|
(E)-nerolidol |
1563 |
1561 |
5,4 |
(2,6) |
--- |
--- |
--- |
--- |
1,1 (0,9) |
--- |
4,7 |
|
Maaliol |
1566 |
1566 |
--- |
--- |
(2,7) |
--- |
--- |
--- |
2,0 (1,4) |
--- |
--- |
|
Spathulenol |
1575 |
1577 |
5,6 (3,1) |
1,6 (4,0) |
(13,0) |
9,1 (9,7) |
11,4 (7,0) |
16.9 (23,5) |
10,3 (5,8) |
5,6 (4,9) |
7,9 |
|
Caryophyllene oxide |
1580 |
1582 |
--- |
(9,2) |
(14,5) |
--- |
10,8 (5,6) |
--- |
--- |
--- |
--- |
|
Globulol |
1586 |
1590 |
6,9 (2,1) |
6,0 (5,7) |
(5,0) |
6,4 (6,5) |
2,2 (1,2) |
--- |
16,1 (12,1) |
7,7 (4,6) |
16,7 |
|
Viridiflorol |
1587 |
1592 |
2,7 (1,9) |
3,1 |
--- |
--- |
--- |
--- |
--- |
--- |
10,1 |
|
Cubeban-11-ol |
1590 |
1595 |
1,4 |
--- |
--- |
--- |
--- |
1,8 (2,2) |
6,6 (5,0) |
5,1 (2,4) |
1.0 |
|
Guaiol |
1595 |
1600 |
2,0 (2,9) |
--- |
(2,3) |
--- |
--- |
--- |
--- |
--- |
--- |
|
Rosifoliol |
1596
|
1600 |
--- |
(1,8) |
(2,8) |
--- |
1,8 (1,0) |
(1,1) |
1,9 (1,5) |
2,9 (1,7) |
4,7 |
|
Khusimone |
1598 |
1604 |
2,4 (1,0) |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
|
Humulene oxide II |
1604 |
1608 |
--- |
--- |
(2,2) |
--- |
1,8 (1,2) |
--- |
--- |
--- |
--- |
|
Jumenol |
1614 |
1618 |
(1,6) |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
2,4 |
|
1-epi-cubebol |
1622 |
1627 |
1,9 (1,2) |
4,4 (3,8) |
(6,2) |
2,5 (2,9) |
2,4 (1,6) |
--- |
2,3 (2,2) |
0,9 (0,6) |
2,1 |
|
Eremoligenol |
1629 |
1629 |
1,4 (1,3) |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
|
γ-eudesmol |
1630 |
1630 |
--- |
--- |
(1,1) |
--- |
--- |
--- |
1,7 (1,6) |
(0,5) |
--- |
|
Epi-α-muurolol |
1638 |
1640 |
3,9 (2,9) |
(3,2) |
(9,3) |
--- |
--- |
--- |
--- |
4,3 (2,4) |
6,9 |
|
α-muurolol |
1640 |
1644 |
3,8 |
--- |
--- |
--- |
0,6 |
(1,7) |
7,2 (6,2) |
--- |
2,2 |
|
Cubenol |
1640 |
1645 |
--- |
--- |
--- |
--- |
1,7 (0,9) |
--- |
--- |
--- |
--- |
|
β-eudesmol |
1646 |
1649 |
3,1 (3,2) |
--- |
(6,0) |
--- |
--- |
--- |
--- |
--- |
--- |
|
α-cadinol |
1647 |
1652 |
10,3 (8,5) |
5,0 (6,9) |
(10,2) |
2,6 (3,3) |
--- |
--- |
27,9 (25,5) |
8,5 |
7,4 |
|
Selin-11-en-4-ol |
1647 |
1654 |
--- |
--- |
--- |
--- |
(2,7) |
--- |
--- |
--- |
--- |
|
Epi-zizanone |
1661 |
1668 |
8,2 (6,4) |
8,7 |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
|
Muscatone |
1674 |
1676 |
--- |
(9,9) |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
|
Germagrena-4(15),5,10(14)-trien-1-alpha-ol |
1683 |
1685 |
--- |
--- |
(2,8) |
--- |
--- |
--- |
--- |
--- |
--- |
|
Ciperotundone |
1687 |
1695 |
--- |
(5,3) |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
|
Vetiselinenol |
1717 |
1730 |
--- |
2,5 |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
|
Khusimol |
1735 |
1741 |
(10,6) |
11,7 |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
|
Drimenol |
1755 |
1766 |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
2,6 |
--- |
|
(E)-isovalencenol |
1784 |
1793 |
(2,2) |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
|
Vitevenic acid |
1805 |
1811 |
(11,8) |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
--- |
|
Monoterpenes (%) |
|
24,9 (11,2) |
2,2 (---) |
--- (---) |
32,2 (31,6) |
24,4 (19,5) |
62,0 (45,7) |
--- (---) |
19,4 (27,4) |
--- (---) |
|
|
Oxygenated Monoterpenes (%) |
|
2,5 (---) |
--- (---) |
--- (---) |
5,3 (5,6) |
0,6 (7,6) |
9,7 (13,9) |
--- (---) |
1,9 (1,4) |
--- (---) |
|
|
Sesquiterpenes (%) |
|
13,5 (6,9) |
19,6 (27,3) |
--- (16,3) |
24,4 (17,6) |
34,4 (23,0) |
4,4 (2,6) |
18,7 (30,3) |
20,9 (11,1) |
19,7 (---) |
|
|
Oxygenated Sesquiterpenes (%) |
|
59,0 (60,7) |
45,8 (52,4) |
--- (78,1) |
20,6 (22,4) |
35,3 (22,6) |
19,5 (29,6) |
77,1 (62,2) |
55,5 (40,0) |
66,1 (---) |
|
|
Total compounds identified (%) |
|
98.9 (78,8) |
67,6 (79,7) |
--- (94,4) |
83,7 (78,2) |
94,7 (72,7) |
96,1 (92,3) |
95,8 (92,5) |
97,9 (80,4) |
85,8 (---) |
|
a IR = Retention Index calculated; b IR= Retention Index of literature; c Species: M. deli= Myrciaria delicatula (DC.) O. Berg; C. aure= Campomanesia aurea O. Berg.; C. xanto= Campomanesia xantocarpha O. Berg.; C. clusi=Calyptranthes clusiifolia O. Berg; M. tene= Myrciaria tenella (D.C) O. Berg; M. reit= Myrceugenia reitzii D. Legrand; E. osor= Eugenia osoriana Mattos & D. Legrand; C. conc= Calyptranthes concinna DC; M. sple= Myrcia splendens (Sw.) DC. .
d Values in parentheses correspond to the composition of the essential oil from dried samples.
4 Conclusions
Among the evaluated species, Myrceugenia reitzii presents average content of superior essential oil. The essential oil content in samples of Myrtaceae family species is higher after drying. The chemical composition of the essential oil of the species presents mono and sesquiterpenes, being the sesquiterpenes occur in a greater percentage in these species. On the other hands, drying affects the chemical composition of the essential oil of the species studied.
Acknowledgment
This research was supported by the funding from the Graduate Program in Agronomy of University of Parana. The authors acknowledge the funding by CAPES – Brazilian Agency Foundation for Research, Brazil – who sponsored the senior author’s graduate studies. We are also gratefully acknowledging the “Environment Institute of Parana State” for providing the license to collect and transport the plant material from “The Private Reserve of Natural Heritage Butuguara”, Parana State.
.
References
SIMÕES CMO. Farmacognosia: do produto natural ao medicamento. 1ª ed. Porto Alegre: Artmed;2017.
SACCHETTI G. Comparative evaluation of 11 essential oils of different origin as functional antioxidants, antiradicals and antimicrobials in foods. Food Chemistry. 2005; 91: 621-632.
GOBBO-NETTO L, LOPES N. Plantas medicinais: Fatores de influência no conteúdo de metabólitos secundário. Química Nova. 2007. 30(2): 374-381.
BIASI LA,DESCHAMPS C. Plantas aromáticas do cultivo à produção de óleo essencial. 1ª edição. Curitiba : Layer Studio Gráfico e Editora Ltda;2009.
YUNES RA, CECHINEL FILHO V. Química de produtos naturais: novos fármacos e a moderna farmacognosia. 5ª Ed. Itajaí: Univali; 2016.
TAIZ L, ZEIGER E. Fisiologia Vegetal.4 ed. Porto Alegre: Artmed; 2009.
BIZZO HR. HOVELL AM. REZENDE CM. Óleos essenciais no Brasil: Aspectos gerais, desenvolvimento e perspectivas. Química Nova. 2009. 32(3): 588-594.
SOUZA CV, LORENZI H. Botânica Sistemática: Guia ilustrado para identificação das famílias de fanerógamas nativas e exóticas no Brasil, baseado em APG II. 2ª edição, Nova Odessa: Editora Plantarum; 2008.
BANDONI AL, CZEPAK MP. Os recursos aromáticos no Brasil: seu aproveitamento industrial para a produção de aromas e sabores. 1ª edição Vitoria: Editores, BANDONI A. L.; CZEPAK M. P. EDUFES; 2008.
FORZZA RC. New Brazilian Floristic List Highlights Conservation Challenges. BioScience. 2012; 62(1):39-45. Fundação Instituto Brasileiro de Geografia e Estatística. Manual técnico da vegetação brasileira. Manuais técnicos em Geociências, numero 1, Rio de Janeiro, 1992. 92p.
PILLAR VP. Estado atual e desafios para a conservação dos campos. Workshop. Instituto de Biociências da Universidade Federal do Rio Grande do Sul, 2006.
SANGWAN NS. Regulation of essential oil production in plants. Plant Growth Regulation. 2001; 34: 3-21.
BAKKALI F. AVERBECK D. IDAOMAR M. Biological effects of essential oils - a revieqw. Food. Chem. Toxicol. 2008; 46(2): 446-475.
PRINS CL,VIEIRA IJC, FREITAS SP. Reguladores de crescimento e produção de óleos essenciais. Brazilian J. Plant Physiology. 2010; 22(2):91-102.
LIMA DM. Substratos e concentrações de ácido naftaleno acético no enraizamento de estacas semilenhosas de Calliandra selloi e Calliandra tweediei. Scientia Agraria. 2006; 7(12):105-111.
KURTZ BC, ARAÚJO DSD. Composição florística e estrutura do componente arbóreo de um trecho de Mata Atlântica na Estação Ecológica Estadual do Paraíso, Cachoeiras de Macacu, Rio de Janeiro, Brasil. Rodriguésia. 2000; 51(78-115):69-112.
ROMAGNOLO MB, SOUZA MC. Os gêneros Calycorectes O.Berg, Hexachlamys O. Berg., Myrciaria O.Berg e Plinia L. (Myrtaceae) na planície alagável do alto rio Paraná, Brasil. Acta Botânica Brasílica. 2004; 18(3):613- 627.
LIMA HC, GUEDES-BRUNI RR. Diversidade de plantas vasculares na reserva ecológica de Macaé de Cima. In: LIMA HC, GUEDES-BRUNI RR (eds.) Serra de Macaé de Cima: Diversidade florística e conservação em Mata Atlântica. 1ª Ed. Rio de Janeiro: Jardim Botânico do Rio de Janeiro; 1997. p.28-39.
LOMBARDI JA, GONÇALVES M. Composição florística de remanescentes de Mata Atlântica do Sudeste de Minas Gerais, Brasil. Revista Brasileira de Botânica. 2000; 23(3):255-282.
CRUZ AVM, KAPLAN MAC. Uso medicinal de espécies das famílias Myrtaceae e Melastomataceae no Brasil. Floresta e Ambiente. 2004; 11(1):47-52.
GUBERT C. Prospecção e Propagação Vegetativa de Espécies Aromáticas da Floresta Ombrófila densa na região Litorânea do Paraná. Curitiba: Dissertação (Mestrado) Curso de Pós-Graduação em Produção Vegetal, Universidade Federal do Paraná; 2010.118p
Wiley Registry of Mass Spectral Data, 6th edn. Wiley Interscience, New York, 1994.
NIST Chemistry Webbook, edited by P. J. Linstrom and W. G. Mallard, available in http://webbook.nist.gov.
ADAMS RP. Identification of essential oil components by gas chromatography/mass spectroscopy. 5th edition. Carol Stream : Allured Publishing Corporation; 2007.
SILVA FAS. Assistat – assistência estatística, versão 7.6 (Beta). 1.aed. Campina Grande: UFCG; 2011.
ASSIS ALA. Secagem, embalagem e armazenamento de folhas de pitangueira. Curitiba. Dissertation. Curitiba: Curso de Pós-Graduação em Produção Vegetal, Universidade Federal do Paraná; 2012.74p.
FIUZA T.S. Caracterização farmacognóstica das folhas de Eugenia uniflora L. (Myrtaceae). Revista Eletrônica de Farmácia.2008; 5(2): 21-31.
DE FAVERI ACA. Eugenia neonitida Sobral and Eugenia rotundifolia Casar. (Myrtaceae) Essential Oils: Composition, Seasonality Influence, Antioxidant Activity and Leaf Histochemistry. Journal of the Brazilian Chemical Society. 2011; 22(8):1531-1538.
LIMA TP. Avaliação da composição química de óleos essenciais de espécies da família Myrtaceae nativas do cerrado com potencial de uso econômico. available from: http://www.iac.sp.gov.br/areadoinstituto/pibic/anais/2010/Artigos/RE10136.pdf