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EDITOR-IN-CHIEF
DR. PAWAN K AGRAWAL
Natural Product Inc.
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agrawal@naturalproduct.us
EDITORS
PROFESSOR ALEJANDRO F. BARRERO
Department of Organic Chemistry,
University of Granada,
Campus de Fuente Nueva, s/n, 18071, Granada, Spain
afbarre@ugr.es
PROFESSOR ALESSANDRA BRACA
Dipartimento di Chimica Bioorganicae Biofarmacia,
Universita di Pisa,
via Bonanno 33, 56126 Pisa, Italy
braca@farm.unipi.it
PROFESSOR DEAN GUO
State Key Laboratory of Natural and Biomimetic Drugs,
School of Pharmaceutical Sciences,
Peking University,
Beijing 100083, China
gda5958@163.com
PROFESSOR YOSHIHIRO MIMAKI
School of Pharmacy,
Tokyo University of Pharmacy and Life Sciences,
Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan
mimakiy@ps.toyaku.ac.jp
PROFESSOR STEPHEN G. PYNE
Department of Chemistry
University of Wollongong
Wollongong, New South Wales, 2522, Australia
spyne@uow.edu.au
PROFESSOR MANFRED G. REINECKE
Department of Chemistry,
Texas Christian University,
Forts Worth, TX 76129, USA
m.reinecke@tcu.edu
PROFESSOR WILLIAM N. SETZER
Department of Chemistry
The University of Alabama in Huntsville
Huntsville, AL 35809, USA
wsetzer@chemistry.uah.edu
PROFESSOR YASUHIRO TEZUKA
Institute of Natural Medicine
Institute of Natural Medicine, University of Toyama,
2630-Sugitani, Toyama 930-0194, Japan
tezuka@inm.u-toyama.ac.jp
PROFESSOR DAVID E. THURSTON
Department of Pharmaceutical and Biological Chemistry,
The School of Pharmacy,
University of London, 29-39 Brunswick Square,
London WC1N 1AX, UK
david.thurston@pharmacy.ac.uk
HONORARY EDITOR
PROFESSOR GERALD BLUNDEN
The School of Pharmacy & Biomedical Sciences,
University of Portsmouth,
Portsmouth, PO1 2DT U.K.
axuf64@dsl.pipex.com
ADVISORY BOARD
Prof. Berhanu M. Abegaz
Gaborone, Botswana
Prof. Viqar Uddin Ahmad
Karachi, Pakistan
Prof. yvind M. Andersen
Bergen, Norway
Prof. Giovanni Appendino
Novara, Italy
Prof. Yoshinori Asakawa
Tokushima, Japan
Prof. Lee Banting
Portsmouth, U.K.
Prof. Julie Banerji
Kolkata, India
Prof. Anna R. Bilia
Florence, Italy
Prof. Maurizio Bruno
Palermo, Italy
Prof. Csar A. N. Cataln
Tucumn, Argentina
Prof. Josep Coll
Barcelona, Spain
Prof. Geoffrey Cordell
Chicago, IL, USA
Prof. Ana Cristina Figueiredo
Lisbon, Portugal
Prof. Cristina Gracia-Viguera
Murcia, Spain
Prof. Duvvuru Gunasekar
Tirupati, India
Prof. Kurt Hostettmann
Lausanne, Switzerland
Prof. Martin A. Iglesias Arteaga
Mexico, D. F, Mexico
Prof. Leopold Jirovetz
Vienna, Austria
Prof. Vladimir I Kalinin
Vladivostok, Russia
Prof. Niel A. Koorbanally
Durban, South Africa
NPC
2013
Vol. 8
No. 2
239 - 242
Department of Food Technology, Faculty of Chemistry, Vinh University, 182-Le Duan, Vinh City,
Nghe An Province, Vietnam
b
Institute of Ecology and Biological Resources, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet,
Cau Giay, Hanoi, Vietnam
c
Natural Products Research Unit, Department of Chemistry, Faculty of Science, Lagos State University,
Badagry Expressway, Ojo, P.M.B. 0001, Lasu Post office, Ojo, Lagos, Nigeria
thangtd@vinhuni.edu.vn; isiaka.ogunwande@lasu.edu.ng
Received: November 12th, 2012; Accepted: December 30th, 2012
The essential oils obtained by hydrodistillation from the leaves of five species of Annonaceace grown in Vietnam were analyzed by gas chromatography
(GC) coupled with mass spectrometry (GC/MS). The main constituents of Artabotrys hongkongensis Hance were the sesquiterpenes spathulenol (13.1%),
-caryophyllene (6.6%), -elemene (6.3%) and -cadinene (6.3%). -Caryophyllene (12.1%), bicycloelemene (11.2%) and bicyclogermacrene (11.6%) were
the predominant components of the oil of Melodorum fruticosum Lour, whereas the oil of Polyalthia longifolia var. pendula Hort was comprised mainly of
-caryophyllene (30.0%), -zingiberene (21.7%), aromadendrene (15.2%) and -selinene (9.1%). The main constituents of Fissistigma maclurei Merr. were
germacrene D (26.1%), -terpinene (8.2%), spathulenol (10.0%), and bicyclogermacrene (6.6%), while -santalene (14.3%), -caryophyllene (6.3%),
terpinen-4-ol (6.3%), caryophyllene oxide (5.7%), trans--bergamotene (5.3%) and allo-ocimene (5.3%) were identified in significant quantity from
Fissistigma rufinerve (Hook.f. & Thomson) Merr.
Keywords: Artabotrys hongkongensis, Melodorum fruticosum, Polyalthia longifolia var. pendula, Fissistigma maclurei, Fissistigma rufinerve.
Thang et al.
RI a
926
930
939
953
976
980
990
1006
1011
1017
1026
1028
1032
1034
1043
1052
1061
1089
1100
1141
1144
1169
1189
1205
1300
1327
1337
1351
1353
1362
1375
1376
1377
1381
1387
1388
1391
1393
1408
1412
1418
1419
1434
1435
1437
1440
1441
1447
1451
1454
1457
1457
1461
1477
1481
1483
1485
1486
1489
1490
1493
1494
1494
1496
1496
1498
1500
1501
1502
1503
1506
1506
1513
1514
1515
RI b
921
923
932
946
969
974
988
1002
1008
1014
1020
1025
1024
1026
1032
1044
1054
1086
1095
1137
1140
1165
1186
1204
1300
1338+
1335
1345
1350
1359
1373
1374
1374
1381+
1387
1387
1389
1392
1407
1410
1416
1417
1431
1432
1434
1437
1439
1445
1449
1452
1454
1455
1458
1475
1479
1481
1483
1484
1487
1489
1492
1492
1493
1496
1495
1498
1500
1500
1501
1502
1505
1505
1514
1514
-
1
1.6
0.4
0.4
0.7
1.5
2.5
0.4
0.5
0.4
0.4
0.4
0.8
0.6
1.9
0.4
0.8
0.6
0.4
1.8
6.6
6.3
1.0
1.4
1.5
4.7
1.7
0.7
0.5
1.6
0.8
2.0
0.5
1.6
1.0
0.7
2
3.0
2.7
2.8
3.2
11.2
2.8
5.5
4.0
12.1
3.8
2.8
3.7
3.4
2.8
4.0
2.0
11.6
-
1523
1525
1530
1546
1550
1561
1576
1583
1585
1593
1599
1605
1608
1608
1521
1522
1528
1544
1548
1559
1577
1582
1590
1592
1599
1600
1602
1607
2.9
6.3
0.3
13.1
0.6
1.3
4.9
3.1
-
3
tr
1.6
0.7
tr
tr
0.5
tr
tr
0.1
tr
1.1
tr
tr
tr
0.1
0.2
Tr
0.1
1.2
0.1
0.7
0.2
30.0
0.2
1.9
0.2
15.2
2.7
0.3
1.1
2.0
0.9
9.1
21.7
0.1
0.1
3.3
0.1
0.1
0.2
0.5
4
0.6
0.1
0.3
0.2
0.5
8.2
0.1
0.7
0.2
0.3
0.1
0.2
0.1
0.1
0.1
0.3
0.1
0.5
4.2
6.5
4.6
0.2
3.0
0.4
0.4
0.7
26.1
0.7
0.1
6.6
1.0
0.1
1.1
1.0
5
1.9
0.8
1.0
0.6
0.8
1.5
0.7
0.8
0.6
0.9
0.8
0.6
0.6
0.6
5.8
0.7
0.5
0.4
0.8
0.6
0.6
0.6
0.7
14.8
6.8
5.8
1.3
3.8
3.6
3.4
0.5
1.0
1.0
1.6
1.5
2.0
0.8
3.5
0.7
0.7
2.4
1.0
0.1
0.8
0.4
0.6
-
4.2
0.3
0.1
0.3
0.6
10.0
2.4
-
1.0
2.2
6.2
0.9
0.2
-
allo-Aromadendrene
1641
1639
4.7
epoxide
-Muurolol
1644
1644
2.6
3.5
5.9
Valerianol
1675
1656
3.1
2.8
0.1
(E,Z)-Farnesol
1718
1714
0.7
Benzyl benzoate
1760
1759
5.5
6.1
Guaizulene
1781
1779
1.2
Phytol
1946
1942
0.8
Eicosane
2000
2000
0.7
n-Heneicosane c
2100
0.6
Total
94.4
99.8
99.2
93.3
90.1
Monoterpene hydrocarbons
8.4
11.7
4.1
10.9
16.2
Oxygenated monoterpenes
2.1
2.8
0.2
3.7
Sesquiterpene hydrocarbons
49.6
64.9
92.6
62.7
55.8
Oxygenated sesquiterpenes
26.7
14.3
2.3
19.7
12.6
Diterpenes
0.8
Others
5.5
6.1
1.0
*
Compounds identified by RI from column, co-injection, literature MS pattern and literature retention
indices (RIb), except where stated; a Retention indices on HP-5MS capillary column; b Literature
Retention indices (Adams [30]); + Found in Joulain and Koenig [32]; - Not present; tr, trace < 0.1%;
c
identified by column RI, co-injection, MS pattern and comparison with authentic MS data collection
in our library; 1. A. hongkongensis; 2. M. fruticosum; 3. P. longifolia var. pendula; 4. F. maclurei ; 5.
F. rufinerve
Species a
A. odoratissimus
A. hexapetalus b
A. hexapetalus b
A. lastoursvillensis
A. insignis, A.
pierreanus, A. rufus,
A. thomsoni, A.
venustus
A. hongkongensis
A. vinhensis
Major components
-caryophyllene (14.717.3%), -copaene (6.49.3%), caryophyllene oxide
(3.2-16.8%)
-caryophyllene (11.4%),
caryophyllene oxide (31.5%)
caryophyllene oxide
(36.2%), -copaene (10.9%),
-caryophyllene (7.8%), asarone (6.1%)
cyperene (25.9%),
cyperenone (11.1%)
cyperenone , 1,5epoxysavial-4(14)-ene
Origin
India
Ref
[18]
Vietnam
[15]
Vietnam
[16]
Gabon
[19]
[20]
Vietnam
This
study
Vietnam
[17]
(7.2-17.2%), (Z)--ocimene (9.1-10.4%), p-methylanisole (7.018.0%), linalool (4.5-7.4%) and -cadinene (4.1-4.3%) as
prominent compounds. From Table 3, a noteworthy observation is
the fact that bicyclogermacrene, caryophyllene and spathulenol
have featured prominently among the volatiles of other species,
such as Melodorum sp. (Claudie River B.P), Melodorum sp. (Topaz
G. Sankowsky), Melodorum sp. (Font Hills G. Sankowsky), M.
leichhardtii and M. uhrii from Australia [23].
Sesquiterpenes, represented by -caryophyllene (30.0%), zingiberene (21.7%), aromadendrene (15.2%) and -selinene
(9.1%), are the dominant class of compound in P. longifolia var.
pendula. Nguyen et al. [12] have reported high quantities of cadinene (24.5%), zingiberene (19.6%) and aromadendrene (19.1%)
in the oil. However, -cadinene was conspicuously absent in our
result, while caryophyllene was identified in low quantity in a
previous study [12].
From Table 4, four chemical forms of the oils of Polyalthia species
may be proposed. These are oils with an abundance of
sesquiterpene hydrocarbons, such as P. longifolia var. pendula [12],
P. longifolia [24], P. suaveolens [25] and P. nitidissima [26]; oils
with relative large amounts of hydrocarbon and oxygenated
sesquiterpenes, as exemplified by P. australis and Polyalthia sp.
(Wyvuri B.P.) [26]; oils dominated by oxygenated sesquiterpenes,
as seen in P. michaelii [26]; and oils consisting of monoterpene
hydrocarbons, as found in the fruit of P. suaveolens [25] and
P. nitidissima [26].
Essential oils from the leaves of five species of Annonaceace grown in Vietnam
Species
Melodorum sp.
(Claudie River B.P)
Melodorum sp.
(Topaz G.
Sankowsky)
M. uhrii
M. leichhardtii
Major components
bicyclogermacrene (29.3%), caryophyllene (26.7%)
bicyclogermacrene (34-50%),
-caryophyllene (11-16%)
Origin
Australia
Ref
[23]
Australia
[23]
bicyclogermacrene (45%),
Australia
[23]
germacrene D (6-10%),
Australia
[23]
bicyclogermacrene (15-19%)
M. fruticosum
-caryophyllene (12.1%),
Vietnam
This
bicyclogermacrene (11.6%),
study
bicycloelemene (11.2%),
(6.1%), -cubebene (5.5%)
-eudesmol (9-5%), Australia
[23]
Oils containing
Melodorum sp.
eudesmol (7-11%), monoterpene- and (Font Hills G.
Sankowsky)
caryophyllene (10-16%),
sesquiterpenes
bicyclogermacrene (1-9%), pinene (14-15%)
Oils rich in
Melodorum sp L.W. benzyl benzoate (20%), benzyl
Australia
[23]
benzenoid
Jessup)
salicylate (2.7%)
compounds
M. fruticosum *, a
1-pheny butanone (20.52),
Thailand
[21]
benzyl alchol (8.75), linalool
(9.27%), -cadinol (5.04%),
globulol (4.25%)
a
Flower sample while others are from the leaves; * contain appreciable amount of monoterpenes and
sesquiterpenes.
Species
P. longifolia
var. pendula
Major components
-caryophyllene (30.0%),
zingiberene (21.7%),
aromadendrene (15.2%) and
-selinene (9.1%)
P. longifolia
-cadinene (24.5%), zingiberene
var. pendula
aromadendrene (19.1%)
P. longifolia
allo-aromadendrene (19.7%),
caryophyllene oxide (14.4%),
and -caryophyllene (13.0%)
P. longifolia a
-copaene/ -muurolol (ca. 8.7%)
(8.6%), viridiflorene (8.1%),
-guaiene (7.8%) and
allo-aromadendrene/-cadinene
(ca.7.4%)
P. suaveolens
-caryophyllene and humulene
(both 34%)
#
P. nitidissima
-caryophyllene, aromadendrene,
D, bicyclogermacrene,
-cadinene, and spathulenol
Oils with relatively P. australis #
-caryophyllene, germacrene D,
large amounts of
bicyclogermacrene,
hydrocarbon and
caryophyllene oxide and
oxygenated
spathulenol
sesquiterpenes
Polalthia sp. (Wyvu -elemene, germacrene D,
bicyclogermacrene,
germacrene B, ledol, globulol
and spathulenol.
Oils dominated by o P. michaelii #
spathulenol
sesquiterpenes
#
Oils consisting of P. nitidissima
-pinene, limonene and
hydrocarbons
()--ocimene
#, b
P. suaveolens
myrcene, -pinene and limonene
Origin
Vietnam
Ref
This
study
Vietnam
[12]
Nigeria
[24]
Nigeria
[24]
Gabon
[25]
Australia
[26]
Australia
[26]
Australia
[26]
Australia
[26]
Gabon
[25]
Stem bark sample ; b Fruit sample; Others are from the leaves; # Quantitative data not
available.
Thang et al.
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Essential Oil of Flowers of Anaphalis contorta, an Aromatic and Medicinal Plant from India
Rajesh K. Joshi
Composition of Essential Oils from Seeds of Abies koreana
Anna Wajs-Bonikowska, Karol Olejnik, Radosaw Bonikowski and Piotr Banaszczak
Chemical Composition of Hypericum richeri subsp. grisebachii Essential Oil from Croatia
Igor Jerkovi, Maja Marasovi, Zvonimir Marijanovi, Kroata Hazler Pilepi, eljan Male and Mladen Milo
Chemical Composition of the Essential Oils from Two Vietnamese Asarum Species: A. glabrum and A. cordifolium
Tran Huy Thai, Ophlie Bazzali, Tran Minh Hoi, Nguyen Anh Tuan, Flix Tomi, Joseph Casanova and Ange Bighelli
Essential Oils from Five Species of Annonaceae from Vietnam
Tran D. Thang, Do N. Dai, Tran M. Hoi and Isiaka A. Ogunwande
Essential Oils from the Leaves of Six Medicinal Plants of Nigeria
Isiaka A. Ogunwande, Nudewhenu O. Avoseh, Guido Flamini, Alimot-Sadiat O. Hassan, AbdulRazaq O. Ogunmoye,
Akindele O. Ogunsanwo, Kamorudeen O. Yusuf, Atuonwu O. Kelechi, Zainab A. Tiamiyu and Godgift O. Tabowei
Comparative Study on In Vitro Activities of Citral, Limonene and Essential Oils from Lippia citriodora and L. alba on
Yellow Fever Virus
Luz Angela Gmez, Elena Stashenko and Raquel Elvira Ocazionez
TLC-Bioautographic Evaluation of In Vitro Anti-tyrosinase and Anti-cholinesterase Potentials of Sandalwood Oil
Biswapriya B. Misra and Satyahari Dey
Composition, Mosquito Larvicidal, Biting Deterrent and Antifungal Activity of Essential Oils of Different Plant Parts of
Cupressus arizonica var. glabra (Carolina Sapphire)
Abbas Ali, Nurhayat Tabanca, Betul Demirci, K. Husnu Can Baser, Jane Ellis, Sandra Gray, Brett R. Lackey, Christine Murphy,
Ikhlas A. Khan and David E. Wedge
Composition of Cassia fistula Oil and its Antifungal Activity by Disrupting Ergosterol Biosynthesis
Md. Irshad, Aijaz Ahmad, Md. Zafaryab, Farah Ahmad, Nikhat Manzoor, Man Singh and M. Moshahid A. Rizvi
Chemical Composition and Biological Activity of the Essential Oil of Amomum biflorum
Chakkrapat Singtothong, Michel J. Gagnon and Jean Legault
Chemical Composition and Antibacterial Activity of Essential Oils from Myrcia alagoensis (Myrtaceae)
Aline do N. Silva, Ana Paula T. Uetanabaro and Anglica M. Lucchese
Composition, in-vitro Anticancer, and Antimicrobial Activities of the Leaf Essential Oil of Machilus mushaensis from Taiwan
Yu-Chang Su, and Chen-Lung Ho
Chemical Constituents and Cytotoxic Evaluation of Essential Oils from Leaves of Porcelia macrocarpa (Annonaceae)
Erica Biolcati P. da Silva, Alisson L. Matsuo, Carlos R. Figueiredo, Mariana H. Chaves, Patricia Sartorelli and Joo Henrique G. Lago
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Book Review
Medicinal Plants of China, Korea, and Japan: Bioresources for Tomorrows Drugs and Cosmetics by Chritophe Wiart, PharmD, PhD
Stephen Pyne
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