Skip to content

Advertisement

Open Access

Chemical variability in the essential oil of leaves of Araçá (Psidium guineense Sw.), with occurrence in the Amazon

  • Pablo Luis B. Figueiredo1Email author,
  • Renan C. Silva2,
  • Joyce Kelly R. da Silva3,
  • Chieno Suemitsu4,
  • Rosa Helena V. Mourão5 and
  • José Guilherme S. Maia1
Chemistry Central Journal201812:52

https://doi.org/10.1186/s13065-018-0428-z

Received: 26 February 2018

Accepted: 30 April 2018

Published: 10 May 2018

Abstract

Background

Psidium guineense, known as Araçá, is a Brazilian botanical resource with commercial application perspectives, based on the functional elements of its fruits and due to the use of its leaves as an anti-inflammatory and antibacterial agent. The essential oils of leaves of twelve specimens of Araçá were analyzed by GC and GC-MS to identify their volatile constituents and associate them with the biological activities reputed to the plant.

Results

In a total of 157 identified compounds, limonene, α-pinene, β-caryophyllene, epi-β-bisabolol, caryophyllene oxide, β-bisabolene, α-copaene, myrcene, muurola-4,10(14)-dien-1-β-ol, β-bisabolol, and ar-curcumene were the primary components in descending order up to 5%. Hierarchical Cluster Analysis (HCA) and Principal Component Analysis (PCA) displayed three different groups with the following chemical types: limonene/α-pinene, β-bisabolene/epi-β-bisabolol, and β-caryophyllene/caryophyllene oxide. With the previous description of another chemical type rich in spathulenol, it is now understood that at least four different chemotypes for P. guineense should occur.

Conclusions

In addition to the use of the Araçá fruits, which are rich in minerals and functional elements, it should be borne in mind that the knowledge of the chemical composition of the essential oils of leaves of their different chemical types may contribute to the selection of varieties with more significant biological activity.

Keywords

Psidium guineense Myrtaceaeessential oil compositionchemical variability

Background

Myrtaceae comprises 132 genera and 5671 species of trees and shrubs, which are distributed mainly in tropical and subtropical regions of the world, particularly South America, Australia and Tropical Asia [1]. It is one of the most prominent families in Brazil, represented by 23 genera and 1034 species, with occurrence in all regions of the country [2, 3]. Psidium is a genus with at least 60 to 100 species, occurring from Mexico and Caribbean to Argentina and Uruguay. Therefore, it is naturally an American genus, although P. guajava, P. guineense and P. cattleyanum are subtropical and tropical species in many other parts of the world [4].

Psidium guineense Swartz [syn. Guajava guineensis (Sw.) Kuntze, Myrtus guineensis (Sw.) Kuntze, Psidium araca Raddi, P. guyanense Pers., P. laurifolium O. Berg, P. rotundifolium Standl., P. sprucei O. Berg, among others [5] (www.tropicos.org/Name/22102032) is a native shrub or small tree up to about 6 m high occurring in all Brazilian biomes, commonly known as Araçá. It has a berry-type fruit with yellow, red or purple peel and whitish pulp, rich in minerals and functional elements, such as vitamin C and phenolic compounds [69]. The leaves and pulp of Araçá have been used as an anti-inflammatory remedy for wound healing and oral antibacterial agent [10, 11], as well as it presented antibacterial activity against pathogenic microorganisms [1113]. Some essential oils of Araçá were previously described: Foliar oil from a specimen growing in Arizona, USA, with predominance of β-bisabolene, α-pinene and limonene [14]; foliar oil from a specimen collected in Roraima, Brazil, with β-bisabolol, epi-α-bisabolol and limonene as the main constituents [15]; and another foliar oil from a specimen sampled in Mato Grosso do Sul Brazil, where spathulenol was the primary volatile compound [16].

The present work aimed at investigating the variability of the chemical composition of the essential oils of different specimens of Psidium guineense, occurring in the Amazon region, to contribute to the knowledge of its chemical types.

Experimental

Plant material

The leaf samples of twelve Psidium guineense specimens were collected in Pará state, Brazil. Collection site and voucher number of each specimen are listed in Table 1. The plant vouchers after the identification were deposited in the Herbaria of Embrapa Amazônia Oriental, in Belém (IAN) and Santarém (HSTM), Pará state, Brazil. The leaves were dried for two days in the natural environment and, then, subjected to essential oil distillation.
Table 1

Identification data and collection site of the specimens of Psidium guineense

Samples

Collection site

Herbarium Nº

Local coordinates

PG-01

Curuçá, PA, Brazil

IAN-195396

0°72’65” S/47°84’07” W

PG-02

Curuçá, PA, Brazil

IAN-195397

0°43’40” S/47°50’58” W

PG-03

Curuçá, PA, Brazil

IAN-195398

0°72’67” S/47°85’13” W

PG-04

Curuçá, PA, Brazil

IAN-195399

0°72’57” S/47°84’84” W

PG-05

Curuçá, PA, Brazil

IAN-195400

0°72’57” S/47°84’07” W

PG-06

Santarém, PA, Brazil

HSTM-3611

2°27’48.7” S/54°44’04” W

PG-07

Monte Alegre, PA, Brazil

HSTM-6763

1°57’24.9” S/54°07’07.8” W

PG-08

Monte Alegre, PA, Brazil

HSTM-6763

1°57’24.9” S/54°07’07.8” W

PG-09

Santarém, PA, Brazil

HSTM-6775

2°25’14.6” S/54°44’25.8” W

PG-10

Santarém, PA, Brazil

HSTM-3603

2°25’08.4” S/54°44’28.3” W

PG-11

Santarém, PA, Brazil

HSTM-6769

2°29’16.8” S/54°42’07.9” W

PG-12

Ponta de Pedras, PA, Brazil

HSTM-6759

2°31’08.3” S/54°52’25.8” W

Isolation and analysis of the composition of oils

The leaves were ground and submitted to hydrodistillation using a Clevenger-type apparatus (3 h). The oils were dried over anhydrous sodium sulfate, and their yields were calculated by the plant dry weight. The moisture content of the samples was calculated using an Infrared Moisture Balance for water loss measurement. The procedure was performed in duplicate.

The oils were analyzed on a GCMS-QP2010 Ultra system (Shimadzu Corporation, Tokyo, Japan), equipped with an AOC-20i auto-injector and the GCMS-Solution software containing the NIST (Nist, 2011) and FFNSC 2 (Mondello, 2011) libraries [17, 18]. A Rxi-5ms (30 m x 0.25 mm; 0.25 μm film thickness) silica capillary column (Restek Corporation, Bellefonte, PA, USA) was used. The conditions of analysis were: injector temperature of 250 °C; Oven temperature programming of 60-240 °C (3 °C/min); Helium as carrier gas, adjusted to a linear velocity of 36.5 cm/s (1.0 mL/min); split mode injection for 1 μL of sample (oil 5 μL : hexane 500 μL); split ratio 1:20; ionization by electronic impact at 70 eV; ionization source and transfer line temperatures of 200 and 250 °C, respectively. The mass spectra were obtained by automatic scanning every 0.3 s, with mass fragments in the range of 35-400 m/z. The retention index was calculated for all volatile components using a homologous series of C8-C20 n-alkanes (Sigma-Aldrich, USA), according to the linear equation of Van den Dool and Kratz (1963) [19]. The quantitative data regarding the volatile constituents were obtained by peak-area normalization using a GC 6890 Plus Series, coupled to FID Detector, operated under similar conditions of the GC-MS system. The components of oils were identified by comparing their retention indices and mass spectra (molecular mass and fragmentation pattern) with data stored in the GCMS-Solution system libraries, including the Adams library (2007) [20].

Statistical analysis

The multivariate analysis was performed using as variables the constituents with content above than 5%. For the multivariate analysis, the data matrix was standardized by subtracting the mean and then dividing it by the standard deviation. For hierarchical cluster analysis, the complete linkage method and the Euclidean distance were used. Minitab software (free 390 version, Minitab Inc., State College, PA, USA), was used for these analyzes.

Results and discussion

Yield and composition of the oils

Psidium guineense is a botanical resource that presents commercial application perspectives, based on its fruits and functional elements, as well as due to the use of its leaves as anti-inflammatory and antibacterial agent [614]. For this study were selected twelve Araçá specimens, with occurrence in various localities of Pará state (PA), Brazil (see Table 1), and which showed different composition for the leaf oils. The yields of the oils from these twelve Araçá samples ranged from 0.1 to 0.9%, where the higher yields were from specimens sampled in the Northeast of Pará, Brazil (0.4-0.9%), and the lower yields were from plants collected in the West of Pará, Brazil (0.1-0.3%). The identification of the constituents of the oils by GC and GC-MS was 92.5% on average, with a total of 157 compounds, where limonene (0.3-47.4%), α-pinene (0.1-35.6%), β-caryophyllene (0.1-24.0%), epi-β-bisabolol (6.5-18.1%), caryophyllene oxide (0.3-14.1%), β-bisabolene (0.1-8.9%), α-copaene (0.3-8.1%), myrcene (0.1-7.3%), muurola-4,10(14)-dien-1-β-ol (1.6-5.8%), β-bisabolol (2.9-5.6%), and ar-curcumene (0.1-5.0%) were the primary components, in descending order up to 5% (see Figure 1 and Table 2). In general, the constituents identified in oils belong to the terpenoids class, with the following predominance: monoterpene hydrocarbons (0.9-76.9%), oxygenated sesquiterpenes (5.2-63.5%), sesquiterpene hydrocarbons (5.6-46.7%), and oxygenated monoterpenes (1.9-8.8%).
Figure 1
Fig. 1

Main constituents identified in the oils of P. guineense: (1) α-pinene, (2) myrcene, (3) limonene, (4) β-caryophyllene, (5) caryophyllene oxide, (6) α-copaene, (7) ar-curcumene, (8) β-bisabolene, (9) muurola-4,10(14)-dien-1-β-ol, (10) epi-β-bisabolol, (11) β-bisabolol

Table 2

Yield and volatile composition of twelve essential oil samples of P. guineense

RI(C)

RI(L)

Constituents (%)

PG-01

PG-02

PG-03

PG-04

PG-05

PG-06

PG-07

PG-08

PG-09

PG-10

PG-11

PG-12

848

846a

(2E)-Hexenal

    

0.3

0.1

      

850

850a

(3Z)-Hexenol

    

0.2

0.1

 

0.1

0.1

   

933

932a

α-Pinene

35.6

26.1

17.7

13.4

34.0

26.4

2.0

0.8

1.0

1.3

0.1

0.6

946

948a

α-Fenchene

0.1

 

0.1

 

0.1

       

957

952a

Benzaldehyde

0.3

0.5

1.1

0.8

0.9

0.6

0.1

0.4

0.3

0.3

0.5

0.1

977

974a

β-Pinene

2.1

1.8

1.4

1.3

1.7

3.9

0.1

    

0.3

985

981a

6-methyl-5-Hepten-2-one

  

0.2

 

0.1

 

0.1

0.4

0.1

 

0.1

0.1

990

988a

Myrcene

0.2

1.4

1.2

1.4

1.3

1.6

0.1

0.1

0.6

0.7

0.1

7.3

1005

1003a

p-Mentha-1(7),8-diene

 

0.5

0.9

1.0

0.7

0.3

0.1

0.2

0.7

1.2

 

0.1

1016

1014a

α-Terpinene

 

0.1

 

0.1

 

0.1

      

1023

1020a

p-Cymene

0.3

0.5

1.0

0.7

1.4

0.5

0.2

0.3

0.4

0.3

0.1

0.6

1028

1024a

Limonene

3.7

30.7

30.4

26.5

37.2

14.0

4.3

9.6

23.4

47.4

0.3

5.4

1031

1032b

1,8-Cineole

0.3

0.1

0.1

0.1

0.1

0.1

0.1

0.2

0.1

 

1.7

0.8

1035

1032a

(Z)-β-Ocimene

0.1

 

0.1

0.1

  

0.1

   

0.1

0.1

1046

1044a

(E)-β-Ocimene

0.1

 

0.2

0.1

 

0.1

0.8

   

0.1

0.1

1057

1054a

γ-Terpinene

0.6

0.4

0.7

0.6

0.3

0.9

  

0.2

0.2

0.1

0.1

1088

1086a

Terpinolene

0.1

0.1

0.2

0.1

0.1

0.3

  

0.1

  

0.1

1100

1095a

Linalool

0.1

 

0.1

0.1

 

0.1

 

0.2

0.1

 

0.1

0.1

1114

1114a

endo-Fenchol

0.1

0.1

0.1

 

0.1

0.1

      

1116

1113b

4,8-dimethyl-(E)-Nona-1,3,7-triene

0.1

 

0.1

         

1120

1122b

trans-p-Mentha-2,8-dien-1-ol

  

0.1

0.1

0.1

       

1125

1122a

α-Campholenal

0.1

 

0.1

 

0.1

0.1

      

1130

1131b

Limona ketone

       

1.6

    

1134

1133a

cis-p-Mentha-2,8-dien-1-ol

    

0.1

  

0.1

0.1

  

0.1

1138

1136a

trans-p-Menth-2-en-1ol

           

0.1

1139

1135a

trans-Pinocarveol

0.4

0.1

0.4

0.1

0.4

0.4

0.2

     

1148

1145a

Camphene hydrate

0.1

0.1

0.1

0.1

0.1

0.2

      

1161

1165b

Hydrocinnamaldehyde

  

0.9

1.5

0.5

       

1166

1165a

Borneol

0.2

0.1

0.2

0.1

0.2

0.3

      

1177

1174a

Terpinen-4-ol

0.1

0.1

0.2

0.1

0.2

0.3

  

0.1

   

1186

1187a

trans-p-Mentha-1(7),8-dien-2-ol

 

0.1

   

0.1

 

0.4

0.2

   

1187

1189a

trans-Isocarveol

  

0.4

 

0.2

       

1191

1186a

α-Terpineol

1.0

0.6

1.3

0.4

1.0

1.7

0.2

0.2

0.1

 

0.1

0.1

1218

1215a

trans-Carveol

  

0.2

 

0.1

0.1

 

0.1

0.1

   

1221

1218a

endo-Fenchyl acetate

0.7

0.2

0.4

0.3

0.4

0.7

      

1226

1227a

cis-p-Mentha-1(7),8-dien-2-ol

  

0.4

 

0.2

0.1

 

0.3

0.1

   

1243

1239a

Carvone

  

0.1

    

0.1

0.1

   

1267

1261a

cis-Chrysanthenyl acetate

 

0.1

0.1

0.1

0.1

0.4

     

0.1

1286

1287a

Bornyl acetate

1.5

0.6

0.7

0.5

0.9

1.5

0.1

    

0.1

1300

1298a

trans-Pinocarvyl acetate

1.5

0.3

0.3

0.2

0.8

1.6

      

1324

1322a

Methyl geranate

 

0.2

0.6

0.6

0.4

 

0.3

0.3

0.9

2.0

0.3

 

1326

1324a

Myrtenyl acetate

0.1

    

0.2

      

1336

1335a

δ-Elemene

0.2

0.1

  

0.1

0.1

 

0.1

 

2.3

  

1338

1339a

trans-Carvyl acetate

  

0.1

0.1

0.2

0.1

      

1364

1359a

Neryl acetate

0.1

0.1

0.1

  

0.1

      

1367

1369a

Cyclosativene

0.1

 

0.1

0.1

        

1378

1374a

α-Copaene

8.1

6.2

8.1

7.2

3.0

3.7

4.2

4.7

2.5

 

1.1

0.3

1383

1379a

Geranyl acetate

0.1

1.1

1.0

1.7

0.6

0.8

0.2

0.2

1.9

0.5

0.8

 

1401

1401a

iso-Italicene

      

0.5

0.6

0.6

0.2

0.1

 

1406

1405a

Sesquithujene

      

0.1

 

0.1

 

0.1

 

1412

1410a

α-Cedrene

      

0.8

0.8

1.0

0.4

0.5

 

1416

1407a

Acora-3,7(14)-diene

      

0.9

0.6

1.0

0.5

  

1423

1417a

β-Caryophyllene

6.1

2.8

0.1

0.1

0.8

5.2

1.4

 

1.0

0.9

1.1

24.0

1426

1419a

β-Cedrene

      

0.1

0.3

0.1

 

0.1

 

1431

1430a

β-Copaene

      

0.2

0.2

0.2

 

0.1

0.1

1435

1434a

γ-Elemene

           

0.2

1436

1432a

trans-α-Bergamotene

      

0.3

0.3

0.3

 

0.2

 

1436

1435b

Perillyl acetate

0.1

0.1

0.1

0.2

0.1

0.1

  

0.2

0.4

  

1440

1439a

Aromadendrene

0.2

0.1

 

0.2

 

0.2

0.2

0.2

    

1441

1439a

Phenyl ethyl but-2-anoate

           

0.4

1444

1440a

(Z)-β-Farnesene

      

0.2

     

1444

1442a

Guaia-6,9-diene

       

0.3

    

1447

1445a

epi-β-Santalene

      

0.1

 

0.1

 

0.1

 

1452

1449a

Amorpha-4,11-diene

      

0.3

 

0.3

   

1452

1453a

Geranyl acetone

  

0.1

       

0.2

 

1455

1452a

α-Humulene

0.9

0.7

0.3

0.5

0.1

0.9

0.4

 

0.1

 

0.2

2.8

1458

1454a

(E)-β-Farnesene

      

1.0

0.1

0.5

0.2

0.3

0.1

1460

1457a

β-Santalene

      

1.2

 

1.1

0.5

0.5

 

1461

1460a

allo-Aromadendrene

0.2

0.2

0.3

0.3

0.1

0.1

      

1464

1464a

α-Acoradiene

      

1.3

1.1

1.3

0.6

0.7

 

1467

1469a

β-Acoradiene

      

0.4

0.3

0.4

0.2

0.2

 

1471

1471a

4,5-di-epi-Aristolochene

   

0.1

 

0.1

0.1

0.1

   

0.1

1474

1474a

10-epi-β-Acoradiene

      

0.4

0.3

0.4

 

0.2

 

1477

1475a

γ-Gurjunene

 

0.3

   

0.3

      

1477

1476a

β-Chamigrene

           

1.0

1479

1478a

γ-Muurolene

  

0.4

0.8

0.1

 

0.3

0.5

0.2

 

0.1

 

1479

1481a

γ-Curcumene

      

0.4

 

1.1

0.8

0.7

 

1482

1479a

ar -Curcumene

      

5.0

4.6

2.5

0.6

1.6

0.1

1486

1481a

γ-Himachalene

1.0

0.9

        

0.4

 

1488

1488a

β-Selinene

0.7

0.8

1.0

3.8

0.5

3.2

3.0

3.7

0.1

  

3.2

1495

1493a

α-Zingiberene

        

0.4

0.3

0.7

 

1497

1498a

α-Selinene

  

0.9

3.7

0.3

2.7

4.3

2.4

   

3.2

1502

1500a

α-Muurolene

0.4

0.3

0.5

0.5

0.1

0.2

0.3

0.4

0.2

 

0.1

0.2

1502

1506a

(Z)-α-Bisabolene

0.1

     

0.8

0.3

1.0

0.7

0.6

0.1

1509

1505a

(E,E)-α-Farnesene

           

2.6

1509

1511a

δ-Amorphene

   

0.4

        

1510

1508b

β-Bisabolene

0.1

     

8.9

4.0

6.4

5.2

4.0

 

1512

1514a

β-Curcumene

      

2.0

0.1

3.6

2.9

2.5

 

1516

1513a

γ-Cadinene

0.3

0.3

0.3

0.4

0.1

0.2

2.9

0.5

   

0.2

1516

1514a

(Z)-γ-Bisabolene

      

0.9

 

1.1

1.0

1.0

 

1519

1520a

7-epi-α-Selinene

   

0.1

 

0.1

     

0.1

1522

1524a

δ-Cadinene

1.0

1.9

1.7

2.6

0.3

0.7

 

0.8

2.7

1.9

 

0.7

1525

1521a

β-Sesquiphellandrene

          

1.8

 

1532

1529a

(E)-γ-Bisabolene

      

2.7

 

2.3

2.0

1.4

0.1

1534

1533a

trans-Cadina-1,4-diene

0.1

0.1

0.1

0.1

 

0.1

      

1534

1536a

Italicene ether

      

0.2

0.5

0.2

 

0.5

 

1539

1540a

10-epi-cis-Dracunculifoliol

      

0.1

0.4

0.1

   

1543

1540b

(E)-α-Bisabolene

      

0.8

 

0.6

0.4

0.4

 

1543

1545a

Selina-3,7(11)-diene

           

0.8

1544

1544a

α-Calacorene

  

0.2

0.3

0.1

0.3

 

0.7

    

1559

1559a

Germacrene B

     

0.1

  

1.1

  

0.4

1565

1561a

E-Nerolidol

0.3

0.1

0.4

0.2

 

0.1

1.0

1.3

 

0.9

2.2

0.2

1570

1571a

Caryolan-8-ol

           

0.4

1572

1570a

Caryophyllenyl alcohol

0.3

    

0.2

      

1579

1578b

ar-Tumerol

      

0.3

0.6

0.1

   

1580

1577a

Spathulenol

0.7

     

0.4

0.6

    

1584

1590a

Globulol

 

0.1

 

0.4

        

1585

1586a

Gleenol

  

0.3

         

1586

1582a

Caryophyllene oxide

2.5

0.7

  

0.6

2.7

1.0

 

0.3

 

1.2

14.1

1589

1590a

β-Copaen-4-α-ol

  

0.5

0.1

0.2

0.3

0.2

0.8

    

1594

1592a

Viridiflorol

0.2

0.9

0.2

0.1

0.1

0.1

0.2

0.3

  

0.2

0.3

1596

1595a

Cubeban-11-ol

      

0.1

0.2

    

1599

1600a

Guaiol

           

0.5

1601

1600a

Cedrol

      

0.4

0.4

0.5

 

0.8

 

1609

1619a

(Z)-8-hydroxy-Linalool

      

0.9

0.7

0.1

   

1611

1613b

Humulene Epoxide

0.4

0.1

0.1

 

0.1

      

1.0

1615

1613b

Copaborneol

    

0.4

       

1617

1618a

1,10-di-epi-Cubenol

    

0.2

      

1.7

1625

1622a

10-epi-γ-Eudesmol

      

1.3

1.0

1.7

0.7

2.1

 

1630

1627a

epi-Cubenol

      

1.5

3.4

0.7

0.5

  

1631

1632a

α-Acorenol

      

1.5

1.1

1.8

1.2

4.3

 

1632

1630a

Muurola-4,10(14)-dien-1-β-ol

5.8

2.4

3.6

2.3

1.6

2.6

      

1635

1636a

β-Acorenol

      

0.4

0.5

0.3

 

0.8

 

1637

1636a

Gossonorol

      

1.0

1.6

0.5

0.3

1.1

 

1639

1638a

Caryophylla-4(12),8(13)-dien-5β-ol

1.3

0.3

  

0.3

2.1

     

1.5

1639

1642b

Caryophylla -4(12),8(13)-dien-5α-ol

3.1

           

1641

1638a

epi-α-Cadinol

1.9

1.8

1.7

1.7

0.6

1.3

1.1

1.6

0.4

0.8

1.4

 

1645

1640a

epi-α-Murrolol

1.1

0.9

    

1.2

 

0.3

  

2.6

1646

1640a

Hinesol

      

0.6

1.8

0.7

0.4

1.1

 

1649

1644a

α-Muurolol

  

1.2

1.1

0.4

0.8

  

1.1

1.0

1.6

3.1

1653

1649a

β-Eudesmol

   

0.1

 

0.1

0.2

0.1

   

0.7

1654

1652a

α-Cadinol

1.8

2.0

1.8

     

0.5

0.4

2.4

 

1655

1651a

Pogostol

      

3.8

4.8

 

0.1

  

1659

1658a

Selin-11-en-4α-ol

   

4.2

 

3.7

     

4.4

1659

1668b

Intermedeol

   

0.2

       

0.5

1660

1656a

α-Bisabolol Oxide B

          

2.3

 

1671

1670a

epi -β-Bisabolol

      

8.1

6.5

9.5

8.2

18.1

 

1674

1674a

β-Bisabolol

      

2.9

1.9

3.6

3.9

5.6

 

1675

1671a

14-hydroxy-9-epi-β-Caryophyllene

1.4

    

0.7

     

1.3

1677

1675a

Cadalene

     

0.1

 

0.6

    

1678

1674a

Helifolenol A

       

0.6

0.2

   

1680

1679a

Khusinol

  

0.3

0.2

        

1685

1683a

epi-α-Bisabolol

      

1.0

0.8

1.3

1.2

2.5

 

1687

1685a

α-Bisabolol

      

2.8

4.0

2.6

2.2

3.4

 

1692

1692a

Acorenone

           

0.2

1696

1696b

Juniper camphor

           

0.8

1698

1700a

Eudesm-7(11)-en-4-ol

      

0.1

    

0.1

1714

1713a

(2E,6Z)-Farnesal

0.2

1.3

1.5

2.7

0.2

   

1.0

0.4

2.8

 

1721

1722a

(2Z,6E)-Farnesol

  

3.7

4.6

0.2

      

0.1

1722

1724a

(2E,6E)-Farnesol

0.4

2.2

   

1.1

 

0.2

0.9

0.3

4.9

 

1741

1740a

(2E,6E)-Farnesal

0.3

1.9

2.1

3.6

0.4

  

0.7

1.4

0.6

3.8

 

1751

1751a

Xanthorrhizol

      

0.1

0.1

    

1757

1753a

Isobaeckeol

       

0.2

    

1767

1768a

β-Bisabolenal

 

0.1

0.2

0.2

      

0.1

 

1841

1832b

Farnesyl acetate

0.1

0.3

0.2

   

0.1

     

1843

1845a

(2E,6E)-Farnesyl acetate

   

0.7

 

0.1

0.1

 

0.1

 

0.1

 

1962

1958a

Geranyl benzoate

 

0.1

0.1

0.2

    

0.2

 

0.1

 

Monoterpenes hydrocarbons

42.9

61.6

54.0

45.5

76.9

48.1

7.8

11.0

26.4

51.1

0.9

14.6

Oxygenated monoterpenes

6.6

3.9

7.5

4.7

6.5

8.8

1.9

4.5

3.9

2.8

3.2

1.4

Sesquiterpene hydrocarbons

19.5

14.6

14.0

21.1

5.6

18.6

46.7

28.0

34.3

21.3

20.7

40.1

Oxygenated sesquiterpenes

21.8

15.1

17.8

22.5

5.2

15.9

31.2

36.5

30.2

23.0

63.5

33.6

Others

0.3

1.8

2.1

2.4

1.9

0.8

0.4

0.9

0.5

0.8

0.6

0.8

Total (%)

91.1

97.0

95.4

96.2

96.1

92.2

88.0

80.9

95.3

99.0

88.9

90.5

Yield of oil (%)

0.6

0.6

0.6

0.9

0.4

0.3

0.2

0.1

0.1

0.2

0.2

0.2

Italic: main constituents above 5%

RI(C) retention time calculated; RI(L) retention time of literature

a Adams [20]

b Mondello [18]

Comparing these results with the composition of other essential oils described for the same plant, a specimen of P. guineense sampled in Arizona, USA, has also been found to contain β-bisabolene, α-pinene, and limonene as its primary constituents [14]. In addition, the oil from another specimen collected in Roraima, Brazil, presented β-bisabolol as the main component, followed by limonene and epi-α-bisabolol [15]. On the other hand, a specimen sampled in Mato Grosso do Sul, Brazil, presented an essential oil with a very high value of spathulenol [16]. Therefore, it is possible that there is a significant variation in the essential oils of different types of Araçá.

Variability in oils composition

The multivariate analysis of PCA (Principal Component Analysis) (Fig. 2) and HCA (Hierarchical Cluster Analysis) (Fig. 3) were applied to the primary constituents present in oils (content ≥ 5.0%), for the evaluation of chemical variability among the P. guineense specimens.
Figure 2
Fig. 2

Dendrogram representing the similarity relation in the oils composition of P. guineense

Figure 3
Fig. 3

Biplot (PCA) resulting from the analysis of the oils of P. guineense

The HCA analysis performed with complete binding and Euclidean distance showed the formation of three different groups. These were confirmed by the PCA analysis, which accounted for 79.5% of the data variance. The three groups were classified as:

Group I Characterized by the presence of the monoterpenes α-pinene (13.4-35.6%) and limonene (3,7-37,2%), composed by the specimens PG-01 to PG-06, collected in Curuçá (PG -01 to PG-05) and Santarém (PG-06), Pará state, Brazil, with 49.2% similarity between the samples.

Group II Characterized by the presence of the sesquiterpenes β-bisabolene (4.0-8.9%) and epi-β-bisabolol (6.5-18.1%), consisting by PG-07 to PG-10 specimens collected in Monte Alegre (PG-07 and PG-08) and Santarém (PG-09 and PG-10), Pará State, Brazil, with 50.3% similarity between samples.

Group III Characterized by the presence of a significant content of β-caryophyllene (24.0%) and caryophyllene oxide (14.1%), constituted by the PG-12 specimen, collected in the city of Ponta de Pedras, Pará state, Brazil, which presented zero% similarity with the other groups.

Thus, based on the study of these essential oils, the multivariate analysis (PCA and HCA) has suggested the existence of three chemical types among the twelve specimens of P. guineense collected in different locations of the Brazilian Amazon. It would then be the chemical types α-pinene/limonene (Group I), β-bisabolene/epi-β-bisabolol (Group II) and β-caryophyllene/caryophyllene oxide (Group III). Taking into account that two essential oils with a predominance of α-pinene/limonene and β-bisabolene/epi-β-bisabolol, respectively, were previously described [14, 15], it is understood that adding these two chemical types to that one rich in β-caryophyllene + caryophyllene oxide, which was a product of this study, besides the other chemical type with a high value of spathulenol, before reported by Nascimento and colleagues (2018) [16], will be now, at least, four chemical types known for the P. guineense essential oils.

Several studies have demonstrated the anti-inflammatory activities of limonene, α-pinene and β-caryophyllene, the primary constituents found in the oils of P. guineense presented in this paper. Limonene showed significant anti-inflammatory effects both in vivo and in vitro, suggesting a beneficial role as a diet supplement in reducing inflammation [21]; limonene decreased the infiltration of peritoneal exudate leukocytes and reduced the number of polymorphonuclear leukocytes, in the induced peritonitis [22]. α-Pinene presented anti-inflammatory effects in human chondrocytes, exhibiting potential anti-osteoarthritic activity [23], and in mouse peritoneal macrophages induced by lipopolysaccharides [24], being, therefore, a potential source for the pharmaceutical industry. The anti-arthritic and the in vivo anti-inflammatory activities of β-caryophyllene was evaluated by molecular imaging [25].

Conclusion

In addition to the great use of the fruits of P. guineense, which are rich in minerals and functional elements, it is understood that the knowledge of the chemical composition of the essential oils of leaves of their different chemical types may contribute to the selection of varieties with more significant biological activity. The study intended to address this gap.

Abbreviations

HCA: 

Hierarchical Cluster Analysis

PCA: 

Principal Component Analysis

GC: 

Gas chromatography

GC-MS: 

Gas chromatography-Mass spectrometry

IAN: 

Herbarium of Embrapa Amazônia Oriental

HSTM: 

Herbarium of Santarém

Declarations

Authors’ contributions

PLBF participated in the collection and preparation the plants to the herbaria, run the laboratory work, analyzed the data and contributed to the drafted paper. RCS helped with lab work. JKRS guided the lab work and data analysis. CS identified the plants and managed their introduction in herbaria. RHVM helped with lab work and data analysis. JGSM proposed the work plan, guided the laboratory work and drafted the manuscript. All authors read and approved the final manuscript.

Acknowledgements

The authors would like to thank CAPES, a Brazilian Government’s research funding agency, for its financial support.

Competing interests

The authors declare that they have no competing interests.

Ethics approval and consent to participate

Not applicable.

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated.

Authors’ Affiliations

(1)
Programa de pós-graduação em Química, Universidade Federal do Pará, Belém, Brazil
(2)
Faculdade de Química, Universidade Federal do Pará, Belém, Brazil
(3)
Programa de Pós-Graduação em Biotecnologia, Universidade Federal do Pará, Belém, Brazil
(4)
Laboratório de Botânica, Universidade Federal do Oeste do Pará, Santarém, Brazil
(5)
Laboratório de Bioprospecção e Biologia Experimental, Universidade Federal do Oeste do Pará, Santarém, Brazil

References

  1. Govaerts R, Sobral M, Ashton P, Barrie F, Holst B, Landrum L, Lucas E, Matsumoto K, Mazine F, Proença C, Soares-Silva L, Wilson P, Niclughdha E: World checklist of selected plant families – Myrtaceae. Kew: The Board of Trustees of the Royal Botanic Gardens; 2013. http://wcsp.science.kew.org.
  2. Landrum LR, Kawasaki ML (1997) The genera of Myrtaceae in Brazil: an illustrated synoptic treatment and identification keys. Brittonia 49:508–536View ArticleGoogle Scholar
  3. Sobral M, Proença C, Souza M, Mazine F, Lucas E: Myrtaceae. Lista de espécies da flora do Brasil. Rio de Janeiro: Jardim Botânico do Rio de Janeiro; 2015. http://floradobrasil.jbrj.gov.br.
  4. Landrum LR (2017) The genus Psidium (Myrtaceae) in the state of Bahia, Brazil. Canotia 13:1–101Google Scholar
  5. Missouri Botanical Garden. www.tropicos.org/Name/22102032.
  6. Caldeira SD, Hiane PA, Ramos MIL, Ramos Filho MM (2004) Caracterização físico-química do Araçá (Psidium guineense Sw.) e do Tucumá (Vitex cymosa Bert.) do Estado de Mato Grosso do Sul. B CEPPA 22:145–154Google Scholar
  7. Genovese MI, Pinto MS, Gonçalves AESS, Lajolo FM (2008) Bioactive compounds and antioxidant capacity of exotic fruits and commercial frozen pulps from Brazil. Food Sci Technol Int 14:207–214View ArticleGoogle Scholar
  8. Gordon A, Jungfer E, da Silva BA, Maia JGS, Marx F (2011) Phenolic constituents and antioxidant capacity of four underutilized fruits from the Amazon region. J Agric Food Chem 59:7688–7699View ArticleGoogle Scholar
  9. Rivero-Maldonado G, Pacheco D, Martín LM, Sánchez-Urdaneta A, Quirós M, Ortega J, Colmenares C (2013) Bracho B (2013) Flavonoides presentes en especies de Psidium (Myrtaceae) de Venezuela. Rev Fac Agron 30:217–230Google Scholar
  10. Di Stasi LC, Oliveira GP, Carvalhaes MA, Queiroz-Junior M, Tien OS, Kakimari SH, Reis MS (2002) Medicinal plants popularly used in the Brazilian Tropical Atlantic Forest. Fitoterapia 73:69–91View ArticleGoogle Scholar
  11. Vieira TI, Gondim BLC, Santiago BM, Valença AMG (2012) In vitro antibacterial and non-stick activity of extracts from leaves of Psidium guineense Sw. and Syzygium cumini (L.) Skeels on oral microorganisms. Rev Gaúcha Odontol 60:359–365Google Scholar
  12. Anesini C, Perez C (1993) Screening of plants used in Argentine folk medicine for antimicrobial activity. J Ethnopharmacol 39:119–128View ArticleGoogle Scholar
  13. Fernandes TG, Mesquita ARC, Randau KP, Franchitti AA, Ximenes EA (2012) In vitro synergistic effect of Psidium guineense (Swartz) in combination with antimicrobial agents against methicillin-resistant Staphylococcus aureus strains. Sci World J 158237:7pGoogle Scholar
  14. Tucker O, Maciarelloa MJ, Landrumb LR (1995) Volatile leaf oils of American Myrtaceae. III. Psidium cattleianum Sabine, P. friedrichsthalianum (Berg) Niedenzu, P. guajava L., P. guineense Sw., and P. sartorianum (Berg) Niedenzu. J Essent Oil Res 7:187–190View ArticleGoogle Scholar
  15. da Silva JD, Luz AIR, da Silva MHL, Andrade EHA, Zoghbi MGB, Maia JGS (2003) Essential oils of leaves and stems of four Psidium spp. Flav Fragr J 18:240–243View ArticleGoogle Scholar
  16. do Nascimento KF, Moreira FMF, Santos JA, Kassuia CAL, Croda JHR, Cardoso CAL, Vieira MC, Ruiz ALTG, Foglio MA, de Carvalho JE, Formagio ASN (2017) Antioxidant, anti-inflammatory, antiproliferative and antimycobacterial activities of the essential oil of Psidium guineense Sw and spathulenol. J Ethnopharmacol 210:351–358View ArticleGoogle Scholar
  17. NIST - National Institute of Standards and Technology (2011) Mass Spectral Library (NIST/EPA/NIH, v.2.0d). The NIST Mass Spectrometry Data Center, Gaithersburg.Google Scholar
  18. Mondello L (2011) Flavors and fragrances of natural and synthetic compounds, Mass Spectral Database (FFNSC 2). John Wiley & Sons Inc, New YorkGoogle Scholar
  19. Van Den Dool H, Kratz PDJA (1963) Generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J Chromatogr A 11:463–471View ArticleGoogle Scholar
  20. Adams RP (2007) Identification of essential oil components by gas chromatography/mass spectrometry. Allured Publishing Corporation, Carol StreamGoogle Scholar
  21. d’Alessio PA, Ostan R, Bisson J-F, Schulzke JD, Ursini MV, Béné MC (2013) Oral administration of d-limonene controls inflammation in rat colitis and displays anti-inflammatory properties as diet supplementation in humans. Life Sci 92:1151–1156View ArticleGoogle Scholar
  22. Kummer R, Estevão-Silva CF, Bastos RL, Rocha BA, Spironello RA, Yamada AN, Bersani-Amado CA, Cuman RKN (2015) Alpha-pinene reduces in vitro and in vitro leukocyte migration during acute inflammation. Int Journal applied Res Nat Prod 8:12–17Google Scholar
  23. Rufino AT, Ribeiro M, Judas F, Salgueiro L, Lopes MC, Cavaleiro C, Mendes AF (2014) Anti-inflammatory and chondroprotective activity of (+)-pinene structural and enantiomeric selectivity. J Nat Prod 77:264–269View ArticleGoogle Scholar
  24. Kim DS, Lee HJ, Han YH, Kee JY, Kim HJ, Shin HJ, Lee BS, Kim SH, Kim SJ, Park SH, Choi BM, Park SJ, Um JY, Hong SH (2015) Alpha-pinene exhibits anti-inflammatory activity through the suppression of MAPKs and the NF-kB pathway in mouse peritoneal macrophages. Am J Chin Med 43:731–742View ArticleGoogle Scholar
  25. Dahham SS, Tabana YM, Khadeer Ahamed MB, Abdul Majid AMS (2015) In vivo anti-inflammatory activity of β-caryophyllene, evaluated by molecular imaging. Molecules & Medicinal Chemistry 1(e1001):6pGoogle Scholar

Copyright

© The Author(s) 2018

Advertisement