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B.

aromatica

The Volatile Constituents From the Leaves, Bark


and Fruits of Bursera aromatica (Proctor) Found in
Jamaica
Grace-Ann O. Junor and Roy B.R. Porter,*
Department of Chemistry, The University of the West Indies, Mona, Kingston, Jamaica

Trevor H. Yee,
Natural Product Institute, The University of the West Indies, Mona, Kingston, Jamaica

Timon Waugh,
Coffee Industry Board, Kingston, Jamaica
Abstract
The essential oil from the leaves, bark and fruits of Bursera aromatica (Burseraceae) collected from the Cockpit
Country region of Jamaica were obtained by hydrodistillation in 0.03%, 0.09% and 1.12% (w/w) yields, respectively,
and were analyzed by GC-FID and GC/MS. Thirty-eight constituents of the leaf oil (92.1%), 26 constituents of the
bark oil (96.5%), and 27 constituents of the fruit oil (93.5%) were identified. The predominant compounds were
nonane (14.7%, 5.2% and 23.7%), a-copaene (15.8%, 23.7% and 14.0%), b-caryophyllene (21.7%, 12.8% and 6.8%),
d-cadinene (11.3%, 21.5% and 4.3%) and viridiflorol (5.9%, 11.8% and 7.9%) in the oils from the leaves, bark and
fruits, respectively. In addition to the components listed above, b-pinene (7.0%) and limonene (8.0%) were also among
the major components of the fruit oil.
Key Word Index
Bursera aromatica, Burseraceae, essential oil composition, nonane, a-copaene, b-caryophyllene, d-cadinene,
viridiflorol.

Introduction
Bursera aromatica, an endemic species of Bursera found in
Jamaica and colloquially known as Siboney, is a perennial plant
belonging to the family Burseraceae. This family is comprised
of approximately 20 genera and 600 species (1). The plant is
an aromatic resinous tree that grows up to 13 m in height with
smooth, grey bark and green, compound leaves of approximately
7cm long. The tree is commonly found in limestone regions
of the northwestern parts of the island (i.e., in the parishes
of Hanover, St. James and Trelawny) (1). Plants of this genus
have long been used in folk medicine for the treatment of
ulcer, venereal disease (2,3), diarrhea, cold, fever and flu (4).
In addition, they are used to alleviate the discomfort of insect
bites, sunburn, rashes and skin sores (5). Resins from this genus
have been reported to show anti-inflammatory activity (6,7)
and antibacterial activity (8,9).
The Bursera genera contain several aromatic species and owe
their economical value to the essential oils they produce(10).

Frankincense and myrrh are two traditional incenses that are


both extracted from species of this family, Boswellia and Commiphora spp., respectively (11). The oils of this genus have been
used in perfumes and cosmetics, for the scenting of soaps, and
in food and beverage flavorings (12). The commercial isolation
of essential oils from species such as B. delphechiana Poiss.
ex Engl. [B. penicillata (D.C.) Engl.], B. simaruba (L.) Sarg.,
and B. aloexylon (Schiede ex Scltdl.) is well-known to the perfumery trade in the western hemisphere (12,13). The major
component of these oils is linalool (6070%), a sought after
perfumery raw material. However, a report on the analysis of
the fruit oil of a Costa Rican type of B. simaruba indicated that
a-terpinene (26.2%), g-terpinene (20.4%), a-pinene(18.2%)
and p-cymene (15.9%) were the major components (14). As
part of their investigation on aromatic and medicinal plants of
Jamaica, the authors hereby report on the chemical composition of the volatiles isolated from the leaves, bark and fruits
of the endemic species, Bursera aromatica.

Received: December 2007

*Address for correspondence

Revised: January 2008


1041-2905/10/0001-019$14.00/0 2010 Allured Business Media
Vol. 22, January/February 2010

Accepted: July 2008


Journal of Essential Oil Research/19

Porter et al.

Experimental
Plant material: Bursera aromatica material (leaves, bark
and fruits) was collected from the Cockpit Country region of
Trelawny, Jamaica. The sample was authenticated at the Herbarium in the Department of Life Sciences, The University
of the West Indies, Mona, Jamaica as Bursera aromatica. A
voucher specimen was deposited at the Herbarium (Accession#UCWI35225).
Analysis: The collected plant materials were separated
into leaves (2.02 kg), bark (1.12 kg) and fruits (0.41 kg). The
fresh plant parts were then separately milled, weighed and

hydrodistilled for 3 h using a Clevenger-type apparatus. The


oils obtained were dried over anhydrous sodium sulfate to
give clear yellow oils and stored at 4C in the refrigerator. The
yields (w/w) were (0.55 g) 0.03%, (1.02 g) 0.09% and (4.72 g)
1.15% for leaves, bark and fruits, respectively.
Analytical GC-FID: GC analyses were carried out on a
Varian CP-3800 gas chromatograph fitted with a WCOT CPSIL 8 fused silica capillary column (30 m 0.25 mm; 0.25mm
film thickness). Helium was used as the carrier gas with a
flow rate of 1 mL/min. The temperature program employed
was 50C (3 min) to 190C (3 min) at a rate of 4C/min, with
injection and detector temperatures maintained at 250C and

Table I. Percentage composition of the volatile constituents from the leaves, bark and fruits of Bursera aromatica grown in Jamaica

Percentage

Components
a

RI
b

nonane
899
a-pinene
933
camphene
947
b-pinene
976
limonene
1027
undecane
1096
a-terpineol
1197
decanol
1208
d-elemene
1331
a-cubebene
1343
cyclosativene
1366
a-copaene
1375
b-cubebene
1384
sativene
1386
a-gurjunene
1400
b-caryophyllene
1414
a-humulene
1451
allo-aromadendrene
1455
d-muurolene
1470
trans-cadinena-1(6),4-diene
1476
viridiflorene
1484
trans-muurola-4(14),5-diene
1486
epi-cubebol
1490
a-muurolene
1493
d-cadinene
1515
trans-calamenene
1518
a-calacorene
1537
b-calacorene
1558
trans-cadinene ether
1566
caryophyllene oxide
1578
globulol
1599
viridiflorol
1604
1-epi-cubenol
1623
a-epi-cadinol
1638
a-epi-muurolol
1640
a-muurolol
1643
a-cadinol
1652
cis-calamenen-10-ol
1653
trans-calamenen-10-ol
1661
8-hydroxy-isobornyl-isobutyrate 1680
Total
Yield (%w/w)

Leaf oil

Bark oil

Fruit oil

IDc

14.7
0.8
tr
1.4
0.4
0.4
0.3
0.2
tr
0.4
1.6
15.8
1.1
-
0.3
21.7
4.4
2.1
0.9
0.8
0.2
-
tr
0.5
11.3
0.3
0.5
0.2
tr
3.1
0.4
5.9
0.9
tr
tr
tr
0.8
tr
0.4
0.3
92.1
0.03

5.2
tr
tr
0.5
tr
tr
tr
-
tr
0.6
0.3
23.7
3.7
tr
tr
12.8
3.7
3.3
1.4
1.3
tr
-
tr
0.7
21.5
-
0.5
tr
tr
2.4
0.6
11.8
0.1
0.5
tr
tr
1.2
tr
0.7
-
96.5
0.09

23.7
4.3
tr
7.0
8.0
-
4.8
-
tr
tr
1.8
14.0
2.3
-
-
6.8
0.9
1.8
0.8
-
-
tr
-
tr
4.3
-
-
-
-
5.2
-
7.9
tr
tr
tr
tr
0.6
0.5
0.6
-
93.5
1.12

GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI
GC/MS, RI

a
Elution order on CPSIL 8 capillary column; b Retention index relative to n-alkane series (C8C25) on the DB-5 column; c GS/MS, tentative identification by gas
chromatography/mass spectrometer; tr = trace (< 0.05%).

20/Journal of Essential Oil Research

Vol. 22, January/February 2010

B. aromatica

220C, respectively. Injection volume for all samples was 1 mL.


Quantitative data were obtained by electronic integration of
FID area counts without the use of correction factors.
GC/MS analysis: The volatiles were analyzed by GC/
MS using a Varian Saturn 2200 instrument interfaced to a
Varian CP-3800 gas chromatograph. The gas chromatograph
was equipped with a WCOT CP-SIL 8 fused silica capillary
column(30 m 0.25 mm; 0.25 mm film thickness). Helium
was used as the carrier gas with a flow rate of 1 mL/min. The
temperature program employed was 50C (3 min) to 190C (3
min) at a rate of 4C/min. The mass spectral data were obtained
on a Saturn 2000 ion trap mass spectrometer with ionization
energy of 70 eV and a mass range of 30450 amu.
Calculation of retention indices (RI): The oils were spiked
with a standard mixture of homologous n-alkane series(C8C25)

and analyzed by GC under the above-mentioned conditions.


Retention indices were directly obtained by the application of
Kovats procedure as described by Sun et al. (15).
Component identification: The components of the oils
were identified by comparison of mass spectral data with
those of NIST 98 library or with authentic compounds and
were confirmed by comparison of their retention indices with
published data in literature (16).

Results and Discussion


The volatile components, percentage composition and
retention indices for the oils from the leaves, bark and fruits
of B. aromatica are listed in Table I. The components are arranged in order of the elution on the WCOT CP-SIL 8 fused
silica capillary column. Analysis of the oils from the leaves,

Table II. The chemical distribution of terpenes and other components in the volatiles from the leaves, bark and fruits of
Bursera aromatica
Compound Class

Leaves

Bark

Fruits

No. of compd.

No. of compd.

No. of compd.

Monoterpenes
Hydrcarbons
Alcohols
Acetates
Total

2.6
0.3
0.3
3.2

4
1
1
6

0.5
trace
-
0.5

4
1
-
5

19.3
2.8
-
22.1

4
1
5

Sesquiterpenes
Hydrocarbons
Alcohols
Oxides
Total

62.1
8.4
3.1
73.6

17
10
2
29

73.5
14.9
2.4
90.8

17
10
2
29

32.7
9.6
5.2
47.5

12
8
1
21

Other

15.3

5.2

23.7

compd. = compound.

Table III. Distribution of the major terpenes and other components in the volatiles from the leaves, bark and fruits of
Bursera aromatica
Component Class

Leaves

Barks

Fruits

mj. comp.

RI

mj. comp.

RI

mj. comp.

RI

Monoterpenes
Hydrcarbons
Alcohol
Acetate

b-pinene
a-terpinol
HII

1.4
0.3
0.3

933
1197
1680

b-pinene
a-terpinol
-

0.5
trace
-

933
1197
-

limonene
a-terpinol
-

8.0
4.8
-

1027
1197
-

Sesquiterpenes
Hydrocarbons
Alcohol
Oxide

b-caryo.
vir. florol
c.oxide

21.7
5.9
3.1

1414
1604
1578

a-copaene
vir. florol
c. oxide

23.7
11.8
2.4

1375
1604
1578

a-copaene
vir. florol
c. oxide

14.0
7.9
5.2

1375
1604
1578

Other

nonane

14.7

899

nonane

5.2

899

nonane

23.7

899

mj. = major; comp. = component; HII = 8-hydroxy-isobornyl-isobutyrate; b-caryo. = b-caryophylene; vir. florol = viridiflorol; c. oxide = caryophyllene oxide.

Vol. 22, January/February 2010

Journal of Essential Oil Research/21

Porter et al.

bark and fruits resulted in the identification of 38, 36 and 27


components, comprising 92.1%, 96.5% and 93.3% of the total
volatiles, respectively.
Qualitatively, the oils were characterized by a high portion
of sesquiterpenes (73.6%, 90.8% and 47.5%). The predominant
ones were a-copaene (15.8%, 23.7% and 14.0%), b-caryophyllene (21.7%, 12.8% and 6.8%), d-cadinene (11.3%, 21.5%
and 4.3%), and viridiflorol (5.9%, 11.8% and 7.9%). Among the
29, 29 and 21 sesquiterpenes identified in the three oils, there
were 17 (62.1%), 17 (73.5%) and 12 (32.7%) hydrocarbons,
10 (8.4%), 10 (14.9%) and 8 (9.6%) alcohols, and 2 (3.1%),
2(2.4%) and 1 (5.2%) oxide.
For the 6, 5 and 5 monoterpenes identified in the leaf,
bark and fruit oils, respectively, there were 4 (2.6%), 4 (0.5%)
and 4(19.3%) hydrocarbons and 1 (0.3%), 1 (tr) and 1 (2.8%)
alcohol. In addition, a monoterpene acetate (0.3%) was present
in the leaf oil. The percentage concentration of the monoterpenes[limonene (8.0%), b-pinene (7.0%), a-terpineol (4.8%)
and a-pinene (4.3%)] in the fruit oil was much higher than
those of the leaf and bark oils (tr1.5%).
The predominant aliphatic constituent was nonane (14.7%,
5.2% and 23.7%) followed by undecane (0.4% and tr), which
were present only in the leaf and bark oils, and decanol (0.2%),
which was present only in the leaf oil. These results are summarized in Table II and Table III.
To the best of the authors knowledge, no previous reports
have been made regarding the essential oil composition from the
leaves, bark or fruits of this plant. However, the components of
the oils from B. aromatica bear significant resemblance to the
volatile components of the fruit oil extracted from B. simaruba
found in Costa Rica. The oils thus support the classification of
the plant belonging to this genus (14).
Acknowledgments

References
1. C.D. Adams, Flowering Plants of Jamaica. pp. 391392, The University
of the West Indies, Mona, Jamaica (1972).
2. H. Pitter, Common plants of Costa Rica. pp. 180182, Editorial Costa
Rica, San Jose, Costa Rica (1978).
3. E. Nunez-Melendez, Medicinal plants of Costa Rica and their folklore. pp.
103105, Editorial Universitaria, Cuidad Universartaria Rodgrigo Facio,
Costa Rica (1975).
4. M. Balick and R. Arvigo, The Rainforest. Lotus Press, New York, NY (1998).
5. M.J. Abad, P. Bermelo, E. Carretero, C. Martinez-Acitores, B. Noguera
and A. Villar, Anti-inflammatory activity of some medicinal plant extracts
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6. S. Sosa, M.J. Balick, R. Arvigo, R.G. Esposito, C. Pizza, G. Altinier and
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(2003).
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from frankincense (Boswellia sp., Burseraceae). Phytochemistry, 62,
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11. A.A. Farooqi, Cultivation of Medicinal and Aromatic Crops. pp. 300307.
University Press, India (2001).
12. M.P. Shiva, A. Lehri and A. Shiva, Aromatic and Medicinal Plants. Intl.
Book Distribution, Dehradun, India (2002).
13. K. Rosales and J.F. Cicci, The volatile oil of the fruits of Bursera simaruba
(L.) Sarg. (Burseraceae) from Costa Rica. Ing. Cienc. Quim., 20, 6061
(2002).
14. Y. Sun, R. Zhang and Q. Wang, Programmed-temperature gas
chromatographic retention index. J. Chromatogr. A, 657, 115 (1993).
15. R.P. Adams, Identification of Essential Oil Components by Gas
Chromatography/Quadruple Mass Spectroscopy. Allured Publ. Corp.,
Carol Stream, IL (2001).

The authors wish to thank The University of the West Indies (U.W.I.),
Mona, for financial assistance to carry out this work. The authors would
also like to thank Patrick A. Lewis from the Herbarium, Department
of Life Sciences, U.W.I. for authenticating the plant materials and the
Coffee Industry Board, Kingston, Jamaica for their generosity towards
the use of their Varian GC/MS instrument.

22/Journal of Essential Oil Research

Vol. 22, January/February 2010

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