Essential oil composition of fruit colour



Yüklə 178.02 Kb.
PDF просмотр
tarix01.08.2017
ölçüsü178.02 Kb.

Moreno et al.

428


Sci. Agric. (Piracicaba, Braz.), v.64, n.4, p.428-432, July/August 2007

Note

ESSENTIAL OIL COMPOSITION OF FRUIT COLOUR

VARIETIES OF Eugenia brasiliensis Lam.

Paulo Roberto H. Moreno

1

*; Marcos Enoque Leite Lima



1

; Marcos Sobral

2

; Maria Cláudia



Marx Young

3

; Inês Cordeiro



3

; Miriam Anders Apel

1,4

; Renata Pereira Limberger



4

; Amélia


Teresinha Henriques

4

1



USP - Instituto de Química, C.P. 26077 - 05585-900 - São Paulo, SP - Brasil.

2

UFMG - Depto. de Botânica, C.P. 486 - 31270-901- Belo Horizonte, MG - Brasil.

3

SMA/SP - Instituto de Botânica, C.P. 3005 - 01061-970 - São Paulo, SP - Brasil.

4

UFRGS - Programa de Pós-Graduação em Ciências Farmacêuticas, Av. Ipiranga, 2752 - 90610-000 - Porto

 Alegre, RS - Brasil.

*Corresponding author

ABSTRACT:  Eugenia brasiliensis Lam. is a variable species concerning fruit colour, with three

recognized varieties. However, the definition of varieties is not easy for Myrtaceae species and not

widely accepted. Two fruit colour varieties (purple and yellow) of E. brasiliensis had their essential oil

composition analysed in order to give support to the existence of varieties for this species. Although,

the major components in the leaf oil are the same monoterpenes for both varieties, 

α-pinene, β-pinene

and 1,8-cineol, the purple fruit variety accumulates more oxygenated sesquiterpenes (33.9%) than

the one with yellow fruits (3.8%). The major differences occurred in purple fruits that present as

major components caryophyllene oxide (22.2%) and 

α-cadinol (10.4%), not found in the leaf oil, and

the yellow fruit oil presented a similar composition as observed for the leaves. These fruit colour

varieties of E. brasilensis can be considered as two distinct chemotypes, since the sesquiterpene

pathway is more operant in the purple variety than in the yellow one, in which monoterpenes are

mainly accumulated.

Key words: Myrtaceae, chemotypes, terpenes, pinenes, caryophyllene oxide



COMPOSIÇÃO DOS ÓLEOS ESSENCIAIS DE VARIEDADES

DE COLORAÇÃO DE FRUTOS DE Eugenia brasiliensis Lam.

RESUMO: A espécie Eugenia brasiliensis Lam. apresenta a coloração dos frutos variável, sendo

reconhecidas três variedades. Entretanto, a definição de variedades não é fácil para espécies de

Myrtaceae e também não é amplamente aceita. Duas variedades de Eugenia brasiliensis, baseado na

cor dos frutos (roxos e amarelos), tiveram a composição de seus óleos essenciais analisadas com a

finalidade de obter indícios de variedade botânica para esta espécie. Embora, os componentes principais

nos óleos das folhas fossem os mesmos monoterpenos para ambas as variedades, 

α-pineno, β-pineno

e 1,8-cineol, a variedade com frutos roxos acumulou maior quantidade de sesquiterpenos oxigenados

(33,9%) do que aquela com frutos amarelos (3,8%). As diferenças principais ocorreram nos frutos

roxos que apresentaram como componente principal o óxido de cariofileno (22,2%) e o 

α-cadinol

(10,4%), não detectados no óleo das folhas, e o óleo dos frutos amarelos apresentou uma composição

similar àquela observada para as folhas. Estas variedades de coloração dos frutos de E. brasilensis

podem ser considerados como dois quimiotipos distintos, uma vez que na variedade com frutos roxos

a rota biossintética para sesquiterpenos encontra-se mais operante do que naquela com frutos amarelos,

onde são acumulados principalmente os monoterpenos.

Palavras-chave: Myrtaceae, quimiotipos,terpenos, pinenos, óxido de cariofileno



INTRODUCTION

Eugenia brasiliensis Lam. is a variable species

concerning fruit characters which is found in coastal

Brazilian forests, commonly known as “Grumixama”

or Brazilian-cherry. Three varieties were recognized by

Cambessèdes (1832-1833) according to their fruit

colours: 1. 

α-variety, with purple fruits, most com-

mon; 2. 


β-variety, with red fruits and 3. γ-variety, with

white fruits. Not much attention has been given to

these varieties this time, although more recently Mattos

(1984) considered that the variety 

γ, described by him

v64n4a13.pmd

2/7/2007, 10:29

428


Essencial oil composition of fruit colour varieties

429


Sci. Agric. (Piracicaba, Braz.), v.64, n.4, p.428-432, July/August 2007

as having yellowish rather than white fruits, should be

recognized as a variety, and it is even called by plant

breeders as “grumixama-branca” (white “grumixama”).

Nevertheless, varieties are not easily definable entities

in the Myrtaceae family and are not widely accepted;

much of the variation that can be considered in only

one species by an author may deserve not only vari-

etal but also specific recognition by others. For in-

stance, the delimitation of Blepharocalyx salicifolius

(Kunth) O. Berg, as considered by Landrum (1986),

encompasses not only the three varieties of this spe-

cies recognized by Legrand & Klein (1978) but also

what they consider as two additional distinct species,



B. suaveolens (Cambess.) Burret and B. picrocarpus

O. Berg.


The essential oil composition of E. brasiliensis

has previously been investigated in specimens collected

in southern and south eastern Brazil. In the southern

specimens, the main components were 

α- and β-

pinene (10.3% and 10.4%, respectively), spathulenol

(7.7%) and 

τ-cadinol (7.1%) (Vérin, 1996; Apel et al.,

2004) and in a specimen collected in São Paulo the

major constituents were 

α- and β-selinene (14.8 and

17.3%) (Fischer et al., 2005). In these previous in-

vestigations, there was no indication of the fruit colour.

In order to correlate the varietal concept to

chemical composition, the essential oil composition of

the two fruit colour varieties from both, leaves and

fruits, were analysed.

MATERIAL AND METHODS

The leaves of both purple and yellow fruit



Eugenia brasiliensis Lam., were collected from six

specimens for each variety cultivated in Martinho

Prado, Moji-Guaçu, SP, between 22°10’43’’ and

22°18’19’’S; 47°8’5’’ and 47°11’34’’W, in October

2000 during the morning. The identification was per-

formed by Marcos Sobral and voucher specimens

(Fischer 13 and 14, respectively) were deposited at the

Herbarium of the Universidade Federal do Rio Grande

do Sul (ICN).

The essential oils were obtained from a pool

of leaves and fruits of the six specimens for each va-

riety by hydro-distillation during 5h using a Clevenger-

type apparatus. The oil from the purple fruit specimens

presented a yield of 0.17 % for leaves and 0.002% for

fruits while the yellow fruit specimens yielded 0.34%

for leaves and 0.15% for fruits.

For component identification, the essential oils

were submitted to Gas Chromatography (GC) and

Mass Spectrometry (GC/MS) analysis. GC analysis

was performed in a Shimadzu GC-17A chromatograph

equipped with Shimadzu GC 10 software, using a fused

silica capillary column (30 m 

× 0.25 mm × 0.25 μm,

coated with DB-5), and a flame ionization detector. In-

jector and detector temperatures were set at 220ºC and

250ºC, respectively; the oven temperature was pro-

grammed from 60º-300ºC at 3ºC min

-1

 and helium was



employed as carrier gas (1 mL min

-1

). The percent-



age compositions were obtained from electronic inte-

gration measurements using flame ionization detection

without taking into account relative response factors.

GC/MS analysis was performed using a

Shimadzu GC-quadrupole MS system (QP 5000), EI

operating at 70 eV; GC carried out in the same condi-

tions as described above. The compound identification

was performed by comparing retention indices (Kóvats

Index (KI), determined relatively to the retention times

of a series of n-alkanes) and mass spectra with those

of authentic samples and with literature data (Adams,

1995; Jennings & Shibamoto, 1980).



RESULTS AND DISCUSSION

The chromatographic analysis of the oils from

both specimens identified (Table 1) fifty-nine com-

pounds representing 93.0 - 100% of the total oil com-

ponents. Clear differences in the pattern of terpenes

were observed for both fruit colour varieties. Although

the major components in the leaf oil are the same for

both varieties (

α-pinene, β-pinene and 1,8-cineol), in

the leaf oil from the purple fruit variety a higher amount

of oxygenated sesquiterpenes (33.9%) was observed

as compared to the yellow fruit variety, in which the

majority of the identified compounds were monoter-

pene hydrocarbons (55.6%) and oxygenated monot-

erpenes (32.6%) and only 3.8% of oxygenated ses-

quiterpenes. In the fruit oils, this difference can be

seen more clearly. The purple fruit oil contained almost

exclusively sesquiterpenes (57.3% oxygenated and

34.1% hydrocarbons) while the yellow fruit oil was

composed in the majority by monoterpenes (42.9%

hydrocarbons and 18.5% oxygenated). The essential

oil composition of the oil from fruits and leaves of the

yellow fruit variety were very similar while in the

purple fruit variety the fruit oil composition was quite

different from that observed in the leaves. In this va-

riety, the major fruit oil components were

caryophyllene oxide (22.2%) and 

α-cadinol (10.4%),

these compounds were not observed in the leaves oil.

In this oil, the major component was the sequiterpene

globulol (6.7%), not found in fruit oil, and very low

amount of monoterpenes were detected.

As the fruit colour alone is a weak character

for the establishment of a variety or the recognition

of two different species, our results might support the

varietal concept for this species due to the remarkable

v64n4a13.pmd

2/7/2007, 10:29

429


Moreno et al.

430


Sci. Agric. (Piracicaba, Braz.), v.64, n.4, p.428-432, July/August 2007

Table 1 - Volatile oil composition of leaves and fruits from two fruit colour varieties of Eugenia brasiliensis.

Continue...

d

n



u

o

p



m

o

C



*

K

I



t

r

a



P

t

n



a

l

P



s

e

v



a

e

L



s

t

i



u

r

F



y

t

e



i

r

a



V

e

l



p

r

u



P

y

t



e

i

r



a

V

w



o

l

l



e

Y

y



t

e

i



r

a

V



w

o

l



l

e

Y



y

t

e



i

r

a



V

e

l



p

r

u



P

e

t



a

t

e



c

a

l



y

h

t



e

0

9



7

7

.



2

9

.



0

2

.



0

e

n



e

l

c



y

c

i



r

t

5



0

9

2



.

0

2



.

0

α



e

n

e



n

i

p



-

4

1



9

8

.



8

1

5



.

3

3



4

.

5



1

6

.



0

α

e



n

e

h



c

n

e



f

-

5



2

9

2



.

0

β



e

n

e



n

i

p



-

3

5



9

0

.



1

1

4



.

4

1



3

.

9



2

.

0



e

n

e



c

r

y



m

6

6



9

6

.



0

0

.



5

7

.



0

1

p

e

n

e



m

y

c



-

2

0



0

1

4



.

0

7



.

0

e



n

e

n



o

m

i



l

6

0



0

1

6



.

8

7



.

2

4



.

4

7



.

0

l



o

e

n



i

c

-



8

,

1



9

0

0



1

6

.



9

2

.



8

2

5



.

7

3



.

0

(-



)

β

e



n

e

m



i

c

o



-

2

2



0

1

3



.

0

(-



)

β

e



n

e

m



i

c

o



-

3

3



0

1

2



.

0

e



n

e

l



o

n

i



p

r

e



t

1

6



0

1

8



.

0

l



o

o

l



a

n

i



l

2

7



0

1

5



.

1

e



n

e

l



i

r

e



p

3

7



0

1

9



.

0

3



.

0

o



x

e

l

o



h

c

n



e

f

-



6

8

0



1

4

.



0

(E

l

o

n



i

b

a



s

-

)



1

1

1



1

4

.



0

l

o



-

4

-



n

e

n



i

p

r



e

t

7



4

1

1



8

.

0



α

l

o



e

n

i



p

r

e



t

-

1



6

1

1



4

.

5



4

.

4



2

.

0



1

5

.



0

e

t



a

t

e



c

a

-



2

l

y



h

t

e



l

y

n



e

h

p



4

2

2



1

6

.



0

α

e



n

e

a



p

o

c



-

4

4



3

1

4



.

0

1



.

1

6



.

1

β



e

n

e



m

e

l



e

-

0



6

3

1



0

.

2



β

e

n



e

l

l



y

h

p



o

y

r



a

c

-



9

8

3



1

1

.



2

7

.



1

4

.



5

2

.



9

α

e



n

e

l



u

m

u



h

-

2



2

4

1



7

.

0



4

.

1



1

.

2



(-

)

β



e

n

e



s

e

n



r

a

f



-

5

2



4

1

2



.

0

o



l

l

a

e

n



e

r

d



n

e

d



a

m

o



r

a

-



9

2

4



1

4

.



0

γ

e



n

e

l



o

r

u



u

m

-



5

4

4



1

8

.



1

D

e



n

e

r



c

a

m



r

e

g



0

5

4



1

5

.



0

r

a

e

n



e

m

u



c

r

u



c

-

2



5

4

1



3

.

0



β

e

n



e

n

i



l

e

s



-

6

5



4

1

9



.

0

e



n

e

r



o

l

f



i

d

i



r

i

v



6

6

4



1

0

.



1

5

.



0

7

.



1

α

e



n

e

l



o

r

u



u

m

-



1

7

4



1

4

.



0

4

.



1

β

e



n

e

l



o

b

a



s

i

b



-

9

7



4

1

6



.

0

6



.

9

γ



e

n

e



n

i

d



a

c

-



3

8

4



1

5

.



0

δ

e



n

e

n



i

d

a



c

-

4



9

4

1



8

.

1



3

.

4



(Z

e

n



e

n

e



m

a

l



a

c

-



)

6

9



4

1

4



.

2

(E



l

o

d



i

l

o



r

e

n



-

)

8



3

5

1



3

.

0



6

.

1



l

o

d



e

l

9



3

5

1



9

.

0



e

n

e



l

l

y



h

p

o



y

r

a



c

-

y



x

o

r



d

i

h



3

4

5



1

0

.



1

l

o



n

e

l



u

h

t



a

p

s



8

4

5



1

2

.



5

4

.



4

I

N



1

2

5



5

1

4



.

5

e



d

i

x



o

e

n



e

l

l



y

h

p



o

y

r



a

c

5



5

5

1



9

.

0



2

.

2



2

l

o



l

u

b



o

l

g



7

5

5



1

7

.



6

2

.



1

v64n4a13.pmd

2/7/2007, 10:29

430


Essencial oil composition of fruit colour varieties

431


Sci. Agric. (Piracicaba, Braz.), v.64, n.4, p.428-432, July/August 2007

difference in the chemical composition of the essen-

tial oils for both fruit colour varieties of E.

brasiliensis, mainly in the fruits. These results indi-

cate that these fruit colour varieties have a distinct

biochemical regulation or even a different genomic

of their secondary metabolism, since in the purple fruit

variety the sesquiterpene pathway is more operant

than in the yellow one, in which mainly monoterpe-

nes are accumulated. Additionally, the phenolic path-

way seems to be different in these two varieties, in

the purple variety this biochemical pathway leads to

the accumulation of anthocyanidins, noticed by the

dark purple colour of the fruits, whether in the yel-

low one these metabolites are apparently not present.

These observations together with the essential oil

analysis may indicate that these two fruit colour va-

rieties are indeed two chemotypes of this species. A

more detailed taxonomic study, such as DNA analy-

sis, is required to define whether we are dealing with

two taxonomic varieties or two distinct species.

Table 1 - Continuation.

i

p

e

l

o



l

u

b



o

l

g



-

4

6



5

1

4



.

2

7



.

1

-



5

-

i

p

e

7

i



p

e

-

-

α



l

o

m



s

e

d



u

e

-



2

7

5



1

1

.



1

7

.



1

C

5



1

H

6



2

)

l



o

m

s



e

d

u



e

(

O



2

5

7



5

1

6



.

1

I



I

e

d



i

x

o



e

n

e



l

u

m



u

h

8



7

5

1



5

.

1



-

i

d



-

0

1



,

1

i



p

e

l

o



n

e

b



u

c

-



3

9

5



1

3

.



0

4

.



2

-

0



1

i

p

e

l

o



m

s

e



d

u

e



-

a

m



a

g

-



5

9

5



1

9

.



0

-

1



i

p

e

l

o



n

e

b



u

c

-



6

9

5



1

8

.



2

7

.



1

1

.



3

γ

l



o

m

s



e

d

u



e

-

9



9

5

1



6

.

0



o

s

i

l

o



n

e

l



u

h

t



a

p

s



-

3

0



6

1

4



.

0

5



.

0

τ



l

o

n



i

d

a



c

-

1



1

6

1



8

.

6



2

.

3



9

.

9



l

o

n



e

b

u



c

2

1



6

1

4



.

1

0



.

1

α



l

o

l



o

r

u



u

m

-



7

1

6



1

1

.



3

5

.



2

2

.



2

α

l



o

n

i



d

a

c



-

0

3



6

1

4



.

0

1



C

5

1



H

2

2



)

l

o



n

e

n



e

m

e



l

a

c



(

O

3



8

3

6



1

9

.



0

C

5



1

H

2



2

)

l



o

n

e



n

e

m



e

l

a



c

(

O



4

3

4



6

1

6



.

0

8



.

0

β



l

o

n



e

l

o



b

a

s



i

b

-



3

8

7



1

6

.



0

e

t



a

o

n



a

c

e



d

a

x



e

h

l



y

h

t



e

8

6



9

1

6



.

0

l



a

t

o



T

0

.



0

0

1



5

.

3



9

0

.



3

9

3



.

5

9



s

d

n



u

o

p



m

o

c



c

i

t



a

h

p



i

l

A



9

.

2



0

.

0



1

.

1



4

.

1



s

n

o



b

r

a



c

o

r



d

y

h



e

n

e



p

r

e



t

o

n



o

M

4



.

9

3



6

.

5



5

9

.



2

4

8



.

1

s



e

n

e



p

r

e



t

o

n



o

m

d



e

t

a



n

e

g



y

x

O



3

.

7



1

6

.



2

3

5



.

8

1



8

.

0



s

n

o



b

r

a



c

o

r



d

y

h



e

n

e



p

r

e



t

i

u



q

s

e



S

1

.



7

7

.



1

1

.



3

1

1



.

4

3



s

e

n



e

p

r



e

t

i



u

q

s



e

s

d



e

t

a



n

e

g



y

x

O



9

.

3



3

8

.



3

8

.



7

1

3



.

7

*



IK = Kóvats Retention Index

1

NI (non-identified) – m/z (rel. int., 70 eV): 41(100), 53(21), 67(14), 91(38), 105(28), 117(17), 131(30), 145(19), 159 (3).



2

Correct isomer not determined – m/z (rel. int., 70 eV): 41(52), 59(100), 81(31), 93(29), 107(38), 149(33), 161(19), 204(9).

3

Correct isomer not determined – m/z (rel. int., 70 eV): 41(100), 43(62), 55(37), 91(27), 105(17), 131(15), 187(7), 202(3).



4

Correct isomer not determined – m/z (rel. int., 70 eV): 41(100), 43(61), 55(37), 91(26), 105(18), 131(16), 187(8), 202(1).



ACKNOWLEDGEMENTS

To the BIOTA/FAPESP Program for the finan-

cial support and to CNPq for the grants awarded.

REFERENCES

ADAMS R.P. Identification of essential oil components by



gas chromatography/ion trap mass spectrometry. Carol

Stream: Allured Pub., 1995. 469p.

APEL, M.A.; SOBRAL, M.; MENUT, C.; BESSIERE, J.-M.;

SCHAPOVAL, E.E.S.; HENRIQUES, A.T. Essential oils from



Eugenia species. Part VII: Sections Phyllocalyx and Stenocalyx.

Journal of Essential Oil Research, v.16, p.135-138, 2004.

CAMBESSÈDES, J. Myrtaceae. In: SAINT-HILAIRE, A. (Org.)



Flora Brasiliae Meridionalis. Paris: A. Belin, 1832-1833.

v.2, p.277-384.

FISCHER, D.C.H.; LIMBERGER, R.P.; HENRIQUES, A.T.;

MORENO, P.R.H. Essential oils from leaves of two Eugenia



brasiliensis specimens from Southeastern Brazil. Journal of

Essential Oil Research, v.17, p.499-500, 2005.

JENNINGS, W.; SHIBAMOTO, T. Qualitative analysis of flavor



and fragrance volatiles by glass capillary gas

chromatography. New York: Academic Press, 1980, 184p.

v64n4a13.pmd

2/7/2007, 10:29

431


Moreno et al.

432


Sci. Agric. (Piracicaba, Braz.), v.64, n.4, p.428-432, July/August 2007

LANDRUM, L.R. Campomanesia, Pimenta, Blepharocalyx,



Legrandia, Acca,  Myrrhinium and Luma.  Flora Neotropica,

v.45, p.1-178, 1986.

LEGRAND, C.D.; KLEIN, R.M. Mirtáceas - Myrciaria,

Pseudocaryophyllus, Blepharocalyx, Espécies suplementares,

espécies cultivadas, generalidades. In: REITZ, R. (Org.) Flora



Ilustrada Catarinense. Itajaí: Herbário Barbosa Rodrigues,

1978. p.731-876.

Received September 13, 2006

Accepted April 20, 2007

MATTOS, J.R. Myrtaceae do Rio Grande do Sul. Roessléria, v.6,

p.3-394, 1984.

VÉRIN, P. Étude chimique des constitutants volatils de plantes

aromatiques du Brésil. Montpellier: Université de Montpellier

II, 1996. 312p. (Ph.D. Thesis.).

v64n4a13.pmd



2/7/2007, 10:29

432


Verilənlər bazası müəlliflik hüququ ilə müdafiə olunur ©azkurs.org 2016
rəhbərliyinə müraciət

    Ana səhifə