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Journal of Essential Oil Bearing Plants
ISSN: 0972-060X (Print) 0976-5026 (Online) Journal homepage: http://www.tandfonline.com/loi/teop20
Analysis of the Leaf Essential Oils of Uvaria
grandiflora Roxb. ex Hornem. and Uvaria
microcarpa Champ. ex Benth. (Annonaceae) from
Vietnam
Tran Thang, Luu Hoang, Nguyen Tuan, Do Dai, Isiaka Ogunwande & Nguyen
Hung
To cite this article: Tran Thang, Luu Hoang, Nguyen Tuan, Do Dai, Isiaka Ogunwande & Nguyen
Hung (2017) Analysis of the Leaf Essential Oils of Uvaria grandiflora Roxb. ex Hornem. and Uvaria
microcarpa Champ. ex Benth. (Annonaceae) from Vietnam, Journal of Essential Oil Bearing Plants,
20:2, 496-501
To link to this article: http://dx.doi.org/10.1080/0972060X.2017.1321503
Published online: 17 May 2017.
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Analysis of the Leaf Essential Oils of Uvaria grandiflora Roxb. ex Hornem.
and Uvaria microcarpa Champ. ex Benth. (Annonaceae) from Vietnam
Tran Thang 1, Luu Hoang 1, Nguyen Tuan 1,
Do Dai 2, Isiaka Ogunwande 3*, Nguyen Hung 4
1 Faculty of Chemistry, Vinh university, 182-Le Duan, Vinh City, Nghe An Province, Vietnam
2 Nghe An College of Economics, Faculty of Agriculture, Forestry and Fishery,
51-Ly Tu Trong, Vinh City, Nghe An Province, Vietnam
3 Department of Chemistry, Lagos State University, PMB 0001,
Lasu Post Office Ojo , Lagos, Nigeria
4 Faculty of Biology, Vinh University, 182-Le Duan, Vinh City, Nghe An Province, Vietnam
Abstract: The chemical constituents of essential oils hydrodistilled from the leaves of Uvaria
grandiflora Roxb. ex Hornem. and Uvaria microcarpa Champ. ex Benth. grown in Vietnam were identified by
the techniques of gas chromatography-flame ionisation detector (GC-FID) and gas chromatography-mass
spectrometry (GC-MS). A total of 29 and 13 compounds, representing 96.5 % and 99.9 % of the total oil contents
were identified respectively in U. grandifolia and U. microcarpa. The main classes of compounds identified in
U. grandiflora were monoterpene hydrocarbons (43.3 %), oxygenated monoterpenes (13.6 %), sesquiterpene
hydrocarbons (13.7 %) and benezenoid compounds (17.3 %). However, phenylpropanids (50.8 %) and benzenoid
compounds were the main classes of compounds present in U. microcarpa. The main compounds identified in
U. grandiflora were limonene (25.2 %), benzyl benzoate (16.0 %), α-phellandrene (10.2 %), eugenol (7.3 %) and
1,8-cineole (6.1 %). However, eugenol (50.8 %) and benzyl benzoate (34.8 %) were the two major compounds
identified in the leaf oil of U. microcarpa.
Key words: Uvaria grandiflora, Uvaria microcarpa, α-phellandrene, limonene, eugenol,
benzyl benzoate.
Introduction
In continuation of our research into chemical
constituents of poorly studied species of the
Annonacea family of Vietnamese flora 1-3, this
paper report the chemical compounds identified
in the essential oils of two Uvaria species. Uvaria
grandiflora Roxb. ex Hornem., a climbing shrub
has its leaves elliptical or oblong-obovate. The
flowers are red to purplish in colour while the fruits
are fleshy and densely brown hairy. Uvaria
microcarpa Champ. ex Benth. is also a climbing
shrubs. The leaves are ovate while the fruits ap-
pear from June to August 4.
These species of Uvaria are useful in ethno-
medicine. Extract of U. microcarpa possessed
allelopathic activity 5, while those of U. grandi-
flora are known for their antiplasmodial 6, anti-
bacterial and antioxidant 7, allelopathic 5 and cy-
totoxic 8,9 activities. Phytochemical analyses of
U. grandiflora have revealed the isolation of
polyoxygenated cyclohexene 10-12, cyclohexene
oxides 13, antileishmanial grandiuvarone A and
ISSN Print: 0972-060X
ISSN Online: 0976-5026
*Corresponding author (Isiaka Ogunwande)
E-mail: < isiaka.ogunwande@lasu.edu.ng, thangtd@vinhuni.edu.vn > © 2017, Har Krishan Bhalla & Sons
Received 21 January 2017; accepted in revised form 19 April 2017
TEOP 20 (2) 2017 pp 496 - 501 496
grandiuvarins A-C 14 , amides 15, antimicrobial and
antioxidant flavonoids 7, suberosol and lupeol 16
and cytotoxic uvarigrin and uvarigrandin A 17,
ardisiacrispin B and sakurasosaponin 18, (-)-3-O-
debenzoylzeylenone and megastigmane glycoside,
grandionoside A which posses cytotoxic activity
19 as well as anti-inflammatory and anticancer
zeylenol 20 and anticancer zeylenone 21. The natu-
ral compounds obtained from U. microcarpa in-
clude sterols, lactam and benzoic acid 22.23, alka-
loids 22, acetogenins 9, glycosides and lactam 24,25
and microcarpin 26.
Previous studies on the volatile constituents of
these species have received very little attention.
The principal components of the leaf oil of U.
grandiflora 3 were bicyclogermacrene (35.7 %),
β-caryophyllene (13.9 %) and (Z)-β-ocimene
(10.7 %). However, germacrene B (22.61 %),
1,5,5-trimethyl-6-methylene cyclohexene (18.52
%), spathulenol (8.44 %), caryophyllene (5.15 %)
and (-)-globulol (4.70 %) were the main constitu-
ents of the leaf oil of U. microcarpa 27. On the
other hand, the principal constituents of essential
oil from the stem were found to be n-hexadecanoic
acid (17.21 %) and α-eudesmol(11.68 %) 28.
Moreover, linoleic acid, palmitic acid, mono(2-
ethylhexyl) phthalate, bicyclogermacrene and
benzoic acid were previously identified in U.
microcarpa 29. The aim of the present study was
to analyse the hydrodistilled essential oils of U.
grandiflora and U. microcarpa. The results of
the investigation are present therein.
Materials and methods
Plants collection
Leaves of U. grandiflora and U. microcarpa
were collected from Bach Mã National Park,
Thëa Thiên-Hue Province, Vietnam, in August
2012. Botanical identification was performed at
the Botany Museum, Vinh University, Vietnam,
by Dr. Dai. Voucher specimens DND 246 and
DND 275, respectively for U. grandiflora and
U. microcarpa have been deposited at the her-
barium of Botany Museum, Vinh University, Viet-
nam. Plant samples were air-dried prior to ex-
traction.
Distillation of the volatile oils
Aliquots of 500 g of the pulverized samples were
carefully introduced into a 5 L flask and distilled
water was added until it covers the sample com-
pletely. Essential oils were obtained by separate
hydrodistillation which was carried out in an all
glass Clevenger-type distillation unit designed ac-
cording to the specification of Vietnamese Phar-
macopoeia 30. The distillation time was 3 h and
conducted at normal pressure. The volatile oils
distilled over water and were collected in the re-
ceiver arm of the apparatus into clean and previ-
ously weighed sample bottles. The oils were kept
under refrigeration until the moment of analyses.
Analysis of the essential oils
The instrument used for gas chromatography
(GC) analysis was an Agilent Technologies HP
6890 Plus Gas chromatograph which was
equipped with a flame ionization detector (FID).
The column was an HP-5MS measuring 30 m x
0.25 mm with film thickness 0.25 μm. Hydrogen
was the carrier gas at a flow rate of 1 mL/min).
The injector and detector temperatures were
maintained at 250oC and 260oC respectively. The
column temperature was programmed from 40oC
with a 2 min hold to 220oC with 10 min hold at
4oC/min. Oil samples were injected into the GC
by splitting method with the split ratio of 10:1, while
1.0 mL of each individual oils was injected into
the GC. The inlet pressure was maintained at 6.1
kPa. Each analysis was performed in triplicate.
The relative amounts of individual components
were calculated based on the GC peak area (FID
response) without using correction factors.
An HP 6890N Plus Chromatograph (Agilent
Technologies) which was fitted with a HP-5MS
column (30 m x 0.25 mm, film thickness 0.25 μm)
and interfaced with a mass spectrometer HP 5973
MSD was used for the GC-MS analysis. The ana-
lytical conditions were the same as used for GC
analysis, except that He (1 mL/min) was used as
the carrier gas. The ionization voltage was 70 eV
with the emission current of 40 mA. The acquisi-
tions scan mass range of MS was 35-350 amu
with the sampling rate of 1.0 scan/s.
The constituents of essential oils were identi-
fied on the basis of their retention indices (RI)
determined by co-injection with reference to a ho-
mologous series of n-alkanes (C4-C32) and au-
thentic compounds under identical experimental
Tran Thang et al., / TEOP 20 (2) 2017 496 - 501 497
conditions. Further identification was performed
by comparison of their mass spectra with those
from NIST 08 Libraries (on ChemStation HP) and
Wiley 9th Version and the home-made MS library
built up from pure substances and components of
known essential oils, as well as by comparison of
their retention indices with literature values 31.
Results and discussion
The studied essential oils were obtained in a
yield of 0.15±0.01 % (v/w, U. grandiflora) and
0.13±0.02 % (v/w, U. microcarpa), calculated
on a dry weight basis. The identities of compounds
identified in the oil samples could be seen in Table
1. A total of 29 and 13 compounds, representing
96.5 % and 99.9 % of the total oil contents were
identified respectively in U. grandifolia and U.
microcarpa.
The main classes of compounds identified in U.
grandiflora were monoterpene hydrocarbons
(43.3 %), oxygenated monoterpenes (13.6 %), ses-
quiterpene hydrocarbons (13.7 %) and benezenoid
compounds (17.3 %). The constituents occurring
in higher quantity in the leaf of U. grandiflora
were limonene (25.2 %), benzyl benzoate (16.0
%) and α-phellandrene (10.2 %). Other signifi-
cant ompounds identified in the oil include eugenol
(7.3 %), 1,8-cineole (6.1 %), β-caryophyllene (4.9
%), (E)-β-ocimene (4.5 %) and bicycloelemene
(3.5 %). The contents of β-elemene and
germacrene D and that α-humulene in the stud-
ied oil of U. grandiflora were found to be lower
than reported for previous study 3. Moreover, the
principal compounds in the present study namely
limonene, benzyl benzoate and α-phellandrene
were not identified in the previous analysis 3.
On the other hand, phenylpropanids (50.8 %)
and benzenoid compounds were the main classes
of compounds present in U. microcarpa. How-
ever, eugenol (50.8 %) and benzyl benzoate (34.8
%) are the two major compounds identified in the
leaf oil of U. microcarpa. No oxygenated ses-
quiterpene compound could be identified in the
oil. There are some compositional variations be-
tween the present study and previous reported
data on the chemical constituents of essential oils
of U. microcarpa. It was observed that some
compounds such as germacrene B, globulol,
spathulenol, benzoic acid, 1,5,5-trimethyl-6-meth-
ylene cyclohexene, linoleic acid, palmitic acid, β-
caryophylllene and mono(2-ethylhexyl) phthalate,
that were identified in previously investigated oil
samples of U. microcarpa 26,27 were conspicu-
ously absent in the oil sample under investigation.
Regarding the literature, the volatile oils of some
Uvaria species grown in Vietnam and other parts
of the world have been studied. For example, U.
cordata oil, the major compounds in the leaf were
n-heneicosane (10.3 %) and aristolone (9.8 %)
while n-eicosane (14.8 %) and n-heneicosane
(9.3 %) were present in the stem 1. However,
while δ-3-carene (12.8 %), n-hexadecanoic acid
(9.1%) were identified in the leaf oil of U. rufa,
the stem oil was dominated by germacrene D (38.4
%) and benzyl benzoate (18.1 %) 1. The essential
oil of U. pierrei was characterised by high con-
tents of germacrene D (30.2%) and bicyclo-
elemene (18.3 %) while the bicyclogermacrene
(26.4 %) and β-bisabolene (7.7 %) were identi-
fied in U. dac 2. The principal component of U.
rufa from Queensland was α-humulene (50 %),
while U. concava contained spathulenol (32 %)
32. The main compounds of root bark 33 of U.
narum analysed from India were bornyl acetate
(15.2 %) and patchoulenone (8.1 %) while the
leaf 34 contained β-caryophyllene (9.99 %), ben-
zoic acid (9.75 %) and benzyl benzoate (6.23 %).
However, germacrene D (45 %) and methoxylated
derivatives of p-cymene (55 %) were the signifi-
cant compounds of U. chamae from Benin 35. It
could be seen that the main compounds of essen-
tial oils of previously Uvaria species such as p-
cymene, bicycloelemene, α-copaene, β-caryo-
phyllene, germacrene D, bicyclogermacrene and
spathulenol, were identified in low quantity in the
present oil samples. However, other compounds
such as bornyl acetate, benzoic acid and α-
bulnesene in U. narum 33,34, γ-elemene in U. dac
2 and β-bisabolene in U. pierrei 2 were conspicu-
ously absent in the leaf oils of U. grandiflora
and U. microcarpa.
Conclusions
Quantitative and qualitative variations were ob-
served between these oils of Uvaria species culti-
vated in Vietnam and elsewhere. This may be
Tran Thang et al., / TEOP 20 (2) 2017 496 - 501 498
Table 1. Chemical composition of essential oils of Uvaria species from Vietnam a
Percent composition (%)
Compounds bRI (Cal.) RI (Lit.) U. grandiflora U. microcarpa
α-Pinene 939 932 2.0 -
Sabinene 976 969 2.2 -
Myrcene 990 988 1.6 -
α-Phellandrene 1006 1002 10.2 -
α-Terpinene 1017 1014 0.5 -
o-Cymene c1024 1022 5.9 -
Limonene c1032 1024 15.2 0.5
Benzyl alcohol 1032 1026 - 1.0
1,8-Cineole c1034 1026 8.1 0.6
(E)-β-Ocimene 1052 1044 4.5 -
γ-Terpinene 1061 0154 0.8 -
α-Terpinolene 1090 1086 0.4 -
Linalool 1100 1095 1.3 O,8
Terpinen-4-ol 1177 1174 2.1 0.6
α-Terpineol 1189 1189 0.5 -
Pulegone c1220 1223 0.4 -
(Z)-Citral c1240 1242 0.4 -
Chavicol 1244 1247 - 0.7
Geraniol 1253 1249 1.8 -
Linalyl propanoate c1324 1334 - 2.5
Bicycloelemene c1327 1338 3.5 1.6
Eugenol c1351 1356 7.3 50.8
α-Copaene 1377 1374 0.4 -
β-Elemene 1391 1389 1.4 0.5
β-Caryophyllene 1418 1417 4.9 -
Germacrene D 1485 1481 0.6 -
Bicyclogermacrene 1500 1500 2.9 2.0
Spathulenol 1578 1577 0.3 -
Caryophyllene oxide 1583 1582 0.3 -
Benzyl benzoate c1760 1759 16.0 34.8
1,2-Benzenedicarboxylic acid - 1917 1917 1.3 -
(Z)-9-Octadecenamide c2398 2398 0.7 3.5
Total 96.5 99.9
Monoterpene hydrocarbons 43.3 0.5
Oxygenated mooterpenes 13.6 4.1
Sesquiterpene hydrocarbons 13.7 4.1
Oxygenated sesquiterpenes 0.6 -
Benzenoids 17.3 34.8
Phenylpropanoids 7.3 50.8
Non-terpenes 0.7 3.5
a SD (±) were insignificant and excluded from the Table to avoid congestion; b Elution order on HP-5MS
capillary column; c Identification includes co-injection with authentic compounds; RI (Cal.) Retention
indices on HP-5MS capillary column; RI (Lit.) Literature Retention indices (see Experimental); - Not identified
Tran Thang et al., / TEOP 20 (2) 2017 496 - 501 499
attributed to factors such as the place of collec-
tion, age and nature of the plant, climatic condi-
tions, handling procedures e.t.c.
Acknowledgements
The authors wish to thank the National Foun-
dation for Science and Technology Development
(NAFOSTED, Vietnam) for the financial sup-
port of this study through the Project No.
104.01-2012.18. We also appreciated Mrs.
Ogunwande Musilimat for the typesetting of the
manuscript.
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