The essential oil from the leaves of Callicarpa arborea Roxb. growing wild in Viet
Nam, was obtained by hydrodistillation and analyzed by gas chromatography – mass
spectrometry. The major constituents of leaves of C. arborea were β-selinene (23.9 %), arturmerone (17.5 %) and α-copaene (8.9 %), with lesser concentrations of caryophyllene oxide
(4.9 %) and ar-turmerol (3.9 %). The chemical composition of this essential oil sample is being
reported for the first time.
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Vietnam Journal of Science and Technology 58 (6A) (2020) 280-288
doi:10.15625/2525-2518/58/6A/15626
CHEMICAL COMPOSITION OF THE ESSENTIAL OIL FROM
LEAVES OF CALLICARPA ARBOREA ROXB. GROWING IN
VIETNAM
Nguyen Huy Hung
1, 2, *
, Do Ngoc Dai
3, 4
, Prabodh Satyal
5
, Nguyen Thanh Chung
3
,
Bui Van Nguyen
6
, Vu Thi Hien
7
, William N Setzer
5, 8, *
1
Center for Advanced Chemistry, Institute of Research and Development, Duy Tan University,
03 Quang Trung, Da Nang, Viet Nam
2
Department of Pharmacy, Duy Tan University, 03 Quang Trung, Da Nang, Vietnam
3
Graduate University of Science and Technology, Vietnam Academy of Science and Technology,
18 Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam
4
Faculty of Agriculture, Forestry and Fishery, Nghe An College of Economics, 51-Ly Tu Trong,
Vinh City, Nghe An Province, Viet Nam
5
Aromatic Plant Research Center, 230 N 1200 E, Suite 102, Lehi, UT 84043, USA
6
University of Khanh Hoa, 01 Nguyen Chanh, Nha Trang, Khanh Hoa, Viet Nam
7
Faculty of Hydrometerology, Ho Chi Minh City University of Natural Resources and
Environment, Ho Chi Minh City 70000, Viet Nam
8
Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA
*
Emails: 1.nguyenhuyhung@duytan.edu.vn, 2.wsetzer@chemistry.uah.edu
Received: xx xx 2020; Accepted for publication: xx xx 2020
Abstract. The essential oil from the leaves of Callicarpa arborea Roxb. growing wild in Viet
Nam, was obtained by hydrodistillation and analyzed by gas chromatography – mass
spectrometry. The major constituents of leaves of C. arborea were β-selinene (23.9 %), ar-
turmerone (17.5 %) and α-copaene (8.9 %), with lesser concentrations of caryophyllene oxide
(4.9 %) and ar-turmerol (3.9 %). The chemical composition of this essential oil sample is being
reported for the first time.
Keywords: Verbenaceae, Callicarpa arborea, essential oil.
Classification numbers: 1.4.6.
1. INTRODUCTION
Callicarpa arborea Roxb., was formerly placed in the Verbenaceae, but is now in the
Lamiaceae [1]. The plant is a shrub or small tree (Figure 1), 6 - 8 m in height and is distributed
in Pakistan, Nepal, Bhutan, India, Sri Lanka, Bangladesh, Myanmar, China, Thailand, Laos,
Cambodia, Viet Nam, Peninsular Malaysia, Singapore, Sumatra, the Philippines, Sulawesi, and
New Guinea [2, 3]. In Viet Nam, the plant has been recorded from Lao Cai, Cao Bang, Bac
Kan, Vinh Phuc, Ha Noi, Hoa Binh, Hai Duong, Ninh Binh, Thanh Hoa, Nghe An, Kon Tum,
Leaf essential oil composition of Callicarpa arborea
281
and Ba Ria-Vung Tau provinces [4,5]. In Chinese traditional medicine (TCM), a powder of C.
arborea leaves is used externally to stop traumatic bleeding [6]. In western Mizoram, India, the
juice from the bark is taken internally to treat stomach pain, dysentery, and vomiting [7], while
the Banrajis of Pithoragarh, Uttarakhand, India, take the fruit of C. arborea to treat sore throat
and mouth sores [8]. In Viet Nam, the plant is used to treat rheumatism and to cure nosebleeds
[9]. Iridoids [6] and triterpenoids [10] have been reported from C. arborea. As part of our
continuing investigation on essential oils from species of the Verbenaceae and Lauraceae in
Viet Nam, we have obtained the leaf essential oil of C. arborea. To our knowledge, this is the
first report of the essential oil composition of C. arborea.
Figure 1. Photograph of Callicarpa arborea (Photograph by Nguyen Bao Chau).
2. MATERIALS AND METHODS
2.1. Plant materials
Leaves of C. arborea were obtained from plants growing in the wild from Dong Van
Commune, Que Phong District, Pu Hoat Nature Reserve, Nghe An province, on October 2018
(19°50ʹ45″ N, 105°06′09″ E, 511 m elevation). The plant was identified by Do Ngoc Dai and a
voucher specimen (DND743) has been deposited in the plant specimen room, Faculty
Agriculture, Forestry, and Fishery, Nghe An, College of Economics. The fresh leaves (3.0 kg),
immediately after collection, were shredded and hydrodistilled for 4 h using a Clevenger type
apparatus (Witeg Labortechnik, Wertheim, Germany) to give a pale-yellow essential oil which
was dried over anhydrous Na2SO4 and stored in a sealed glass vial at 4 °C until analyzed.
2.2. Gas chromatography – Mass spectrometry
The leaf essential oil of C. arborea was analyzed by gas chromatography – mass
spectrometry (GC-MS) as previously described [11]: Shimadzu GCMS-QP2010 Ultra operated
in the electron impact (EI) mode (electron energy = 70 eV), scan range = 40–400 atomic mass
units, scan rate = 3.0 scans/s, and GC–MS solution software; ZB-5 fused silica capillary
column (30 m length × 0.25 mm inner diameter) with a (5 % phenyl)-polymethylsiloxane
stationary phase and a film thickness of 0.25 μm; helium carrier gas with a column head
pressure of 552 kPa and flow rate of 1.37 mL/min. The injector temperature was 250 °C and
the ion source temperature was 200 °C. The GC oven temperature was programmed to have an
initial temperature of 50 °C, and the temperature increased at a rate of 2 °C/min to 260 °C. A
5 % w/v solution of the sample in CH2Cl2 was prepared, and 0.1 μL was injected with a splitting
mode (30:1). Identification of the oil components was based on their retention indices
determined by reference to a homologous series of n-alkanes, and by comparison of their mass
Nguyen Huy Hung, et al.
282
spectral fragmentation patterns with those reported in the databases [12 - 15], with RI values
within ± 10 units and with matching factors > 80 %. The concentrations of the essential oil
components were calculated from raw peak areas, normalized to 100 %, without
standardization.
3. RESULTS AND DISCUSSION
Hydrodistillation of the leaves of C. arborea gave a pale-yellow essential oil in 0.015 %
yield. The chemical composition of the leaf oil was determined using GC-MS and is
summarized in Table 1. A total of 62 compounds were identified in the essential oil accounting
for 92.3 % of the composition. Sesquiterpene hydrocarbons (45.2 %) and oxygenated
sesquiterpenoids (39.4 %) dominated the leaf oil composition. The major components in the
essential oil were β-selinene (23.9 %), ar-turmerone (17.5 %), and α-copaene (8.9 %).
Table 1. Chemical composition of the leaf essential oil of Callicarpa arborea from central Viet Nam.
RIcalc RIdb Compound %
932 933 α-Pinene tr
972 972 Sabinene tr
977 978 β-Pinene 0.1
989 991 Myrcene tr
1005 1006 Octanal 0.1
1025 1025 p-Cymene 0.2
1029 1030 Limonene 0.4
1032 1032 1,8-Cineole 0.2
1046 1046 (E)-β-Ocimene 0.1
1071 1076 1-Octanol 0.1
1087 1086 trans-Linalool oxide (furanoid) 0.1
1091 1093 p-Cymenene 0.2
1100 1101 Linalool 0.5
1106 1107 Nonanal 0.3
1114 1110 2,4-Dimethylanisole 0.3
1120 1120 3-Octyl acetate 0.1
1154 1153 p-Vinylanisole 0.5
1186 1187 (3Z)-Hexenyl butyrate 0.6
1187 1188 4′-Methylacetophenone 0.3
1189 1189 p-Cymen-8-ol 1.0
1231 1231 (3Z)-Hexenyl 2-methylbutanoate 0.1
1257 1257 p-Anisaldehyde 0.5
1285 1285 Bornyl acetate 0.1
1289 1287 Dihydroedulan IA 0.2
1294 1294 Dihydroedulan IIA 0.2
1377 1375 α-Copaene 8.9
1389 1390 trans-β-Elemene 0.3
1406 1403 9,10-Dehydroisolongifolene 0.4
1418 1422 β-Ylangene 0.3
1427 1430 γ-Maaliene 0.4
1430 1430 β-Copaene 0.7
Leaf essential oil composition of Callicarpa arborea
283
1439 1438 Aromadendrene 3.6
1460 1457 allo-Aromadendrene 1.1
1470 1473 4,5-di-epi-Aristolochene 0.3
1476 1478 γ-Muurolene 1.4
1483 1482 ar-Curcumene 1.0
1492 1492 β-Selinene 23.9
1497 1497 α-Selinene 0.7
1499 1500 α-Muurolene 0.3
1514 1512 γ-Cadinene 0.8
1522 1519 trans-Calamenene 0.5
1562 1560 (E)-Nerolidol 0.9
1572 1568 Palustrol 0.8
1580 1582 ar-Turmerol 3.9
1585 1587 Caryophyllene oxide 4.9
1588 1592 Globulol 3.2
1590 1591 β-Copaen-4α-ol 0.3
1596 1594 Viridiflorol 1.4
1598 1599 Cubeban-11-ol 0.4
1604 1594 anti,anti,anti-Helifolen-12-al B 0.5
1606 1605 Ledol 0.5
1608 1609 Rosifoliol 0.3
1612 1613 Humulene epoxide II 0.5
1615 1615 Zingiberenol 0.5
1623 1620 anti,syn,syn-Helifolen-12-al C 0.5
1628 1632 Muurola-4,10(14)-dien-1β-ol 1.5
1669 1668 ar-Turmerone 17.5
1675 1677 Cadalene 0.5
1677 1676 Mustakone 1.1
1745 1742 (6S,7R)-Bisabolone 0.5
1842 1841 Phytone 1.1
2109 2109 Phytol 0.7
Monoterpene hydrocarbons 0.9
Oxygenated monoterpenoids 1.8
Sesquiterpene hydrocarbons 45.2
Norsesquiterpenoids 0.3
Oxygenated sesquiterpenoids 39.4
Norditerpenoids 1.1
Diterpenoids 0.7
Benzenoid aromatics 1.6
Others 1.4
Total identified 92.3
RIcalc = Retention Indices determined with respect to a homologous series of n-alkanes on an HP-5ms column; RIdb =
Retention Indices from the databases [12 - 15]; tr = trace (< 0.05 %).
Nguyen Huy Hung, et al.
284
This is the first report of the leaf essential oil composition of C. arborea.
Our team had previously analyzed the leaf essential oil compositions of eight Callicarpa
species from central Viet Nam (C. bodinieri, C. candicans, C. formosana, C. longifolia, C.
nudiflora, C. petelotii, C. rubella, and C. sinuata) [16] (Table 2). With the exception of C.
nudiflora, the leaf oils of these Callicarpa species were also dominated by sesquiterpene
hydrocarbons and oxygenated sesquiterpenoids. β-Selinene and caryophyllene oxide are
common components in the leaf essential oils of Vietnamese Callicarpa species. Although β-
selinene was a major component in the leaf oils of C. arborea (23.9 %), C. bodinieri (8.9 %), C.
candicans (4.5 - 6.2 %), C. longifolia (3.2 - 13.2 %), and C. petelotii (4.0%), it was a relatively
minor component in C. formosana (0.1 %), C. nudiflora (0.1 %), C. rubella (0.8 - 1.6 %), and
C. sinuata (1.8 %) essential oils. Caryophyllene oxide is relatively abundant in all Callicarpa
essential oils. α-Copaene was also found in all of the Callicarpa leaf oils from Viet Nam, and
was a major component in C. bodinieri (5.4 %), C. arborea (8.9 %) and C. sinuata (12.6 %).
Caryophyllene oxide, α-copaene, and β-selinene are relatively common sesquiterpenes, so they
cannot be considered to be signature compounds for the Callicarpa genus.
Curiously, (E)-caryophyllene was relatively abundant in all Callicarpa essential oils except
for C. arborea where it was not detected. α-Humulene was also found in all Callicarpa essential
oils except for C. arborea. In contrast, however, ar-turmerone was found in only minor
quantities in C. bodinieri (0.5 %), C. formosana (0.3 %), and C. sinuata (0.2 %), and was not
detected in the leaf oils of C. candicans, C. longifolia, C. nudiflora, C. petelotii, or C. rubella
but presented as the major component in the leaf oil of C. arborea (17.5 %). Thus, there do not
seem to be any essential oil components that would serve to define the chemistry of the
Callicarpa genus.
The sesquiterpenoid ar-turmerone has shown anti-inflammatory activity by suppressing
inflammatory cytokine production [17], inhibition of cyclooxygenase 2 (COX-2) and inducible
nitric oxide synthase (iNOS) [18], and may support the traditional use of C. arborea in Viet
Nam to treat rheumatism. However, ar-turmerone has also been shown to inhibit platelet
aggregation [19], which belies the use of C. arborea to treat nosebleeds.
Figure 2. The gas chromatogram of Callicarpa arborea essential oil.
Leaf essential oil composition of Callicarpa arborea
285
Table 2. The main essential oil components of some Callicarpa species from central Viet Nam.
RIdb Compound C. b C. c C. f C. l C. n C. p C. r C. s C. a
NL NĐ ĐL HV NL NĐ ĐN ST TG NG BM TG ST PH
932 α-Pinene 1.5 --- tr --- 0.6 0.4 0.1 8.1 0.4 0.1 0.5 1.1 0.1 tr
974 β-Pinene 1.7 --- 0.1 --- 0.3 --- --- 34.2 0.4 0.3 2.4 1.7 tr 0.1
1024 Limonene 8.0 --- 0.1 --- 0.1 0.5 0.1 1.0 0.4 0.1 0.4 0.8 0.1 0.4
1195 Myrtenal 0.3 --- --- --- --- --- --- 6.8 --- 0.1 --- --- --- ---
1345 α-Cubebene 0.1 --- --- --- --- --- --- --- tr 0.1 0.4 17.4 0.2 ---
1374 α-Copaene 5.4 0.1 0.1 --- 0.1 0.4 0.6 0.3 0.1 0.4 0.1 4.6 12.6 8.9
1417 (E)-Caryophyllene 1.0 19.0 7.1 15.3 6.5 11.8 28.0 2.9 2.7 0.3 7.1 18.0 3.8 ---
1452 α-Humulene 0.6 2.4 1.2 1.9 0.6 1.9 1.6 0.2 53.8 0.1 0.9 2.0 24.8 ---
1489 β-Selinene 8.9 6.2 5.7 4.5 0.1 3.2 13.2 0.1 4.0 1.6 0.9 0.8 1.8 23.9
1498 α-Selinene 0.9 --- 1.0 1.7 0.2 --- --- --- 12.8 --- 0.7 --- --- 0.7
1500 Bicyclogermacrene --- 3.0 --- --- --- --- 5.9 --- --- --- --- 4.6 4.0 ---
1502 trans-β-Guaiene --- --- --- --- --- 22.2 0.4 --- --- --- --- --- --- ---
1505 β-Bisabolene 0.2 --- --- --- 18.6 1.2 0.3 --- --- 0.7 25.0 0.1 --- ---
1559 Germacrene B --- 6.1 0.1 5.1 --- 1.3 2.1 --- --- --- 4.6 0.1 --- ---
1577 Spathulenol 2.3 0.7 2.1 1.0 --- 1.1 5.3 2.9 0.1 3.9 0.2 2.7 5.9 ---
1582 Caryophyllene oxide 9.8 2.9 13.4 3.4 38.9 1.7 6.1 20.1 2.0 25.1 3.0 2.7 1.9 4.9
1608 Humulene epoxide II 2.6 0.3 1.6 0.4 1.5 0.3 --- 0.5 8.1 3.8 0.4 0.2 6.7 0.5
1657 Atractylone --- 37.7 4.2 42.4 --- --- --- --- --- --- --- --- --- ---
1658 Selin-11-en-4α-ol --- --- --- --- --- 8.0 7.4 --- --- --- --- --- 0.7 ---
1668 ar-Turmerone 0.5 --- --- --- 0.3 --- --- --- --- --- --- --- 0.2 17.5
1693 Germacrone --- 0.3 --- 0.2 --- 2.7 --- --- --- --- 22.1 --- --- ---
1704 cis-Thujopsenol --- --- --- --- --- --- --- --- --- 8.8 --- --- --- ---
1734 1(10),11-Eremophiladien-9-one --- 0.5 --- --- --- 6.7 --- --- --- --- --- --- --- ---
1884 Corymbolone --- --- --- --- --- --- --- --- --- 5.6 --- --- --- ---
RIdb = Retention Indices from the databases [12–15]; tr = trace (< 0.05%). NL: Ngoc Linh Nature Reserve; ĐL: Dai
Loc district, Quang Nam province; HV: Hoa Vang district, Da Nang city; NĐ: Nghia Dan District, Nghe An
province; ĐN: Da Nang City; ST: Son Tra Peninsula, Da Nang City; TG: Tay Giang District, Quang Nam province;
NG: Nam Giai Commune, Que Phong district, Pu Hoat Nature Reserve, Nghe An province; BM: Bach Ma National
Park, Phu Loc District, Thua Thien Hue province; PH: Pu Hoat Nature Reserve, Nghe An province. C. b: C.
bodinieri; C. c: C. candicans; C. f: C. formosana; C. l: C. longifolia; C. n: C. nudiflora; C. p: C. petelotii; C. r: C.
rubella; C. s: C. sinuate; C. a: C. arborea.
Vietnam Journal of Science and Technology 58 (6A) (2020) 280-288
doi:10.15625/2525-2518/58/6A/15626
4. CONCLUSIONS
This is the first report on the leaf essential oil composition of Callicarpa arborea. As with
most other Callicarpa species, the leaf oil was rich in sesquiterpene hydrocarbons and
oxygenated sesquiterpenoids. In contrast to other Callicarpa essential oils, the leaf oil of C.
arborea had a large concentration of ar-turmerone.
Acknowledgements. This research was funded by Vietnam National Foundation for Science and
Technology Development (NAFOSTED), grant number 106.03-2019.25. P.S. and W.N.S. participated in
this work as part of the activities of the Aromatic Plant Research Center (APRC,
https://aromaticplant.org/). The Callicarpa arborea photo was kindly provided by Nguyen Bao Chau.
CRediT authorship contribution statement. Nguyen Huy Hung: Methodology, Investigation, Funding
acquisition. Do Ngoc Dai: Formal analysis. Prabodh Satyal: Methodology, Investigation. Nguyen Thanh
Chung: Formal analysis. Bui Van Nguyen: Supervision. Vu Thi Hien: Investigation. William N. Setzer:
Methodology, Investigation, Formal Analysis.
Declaration of competing interest. The authors declare that they have no known competing financial
interests or personal relationships that could have appeared to influence the work reported in this paper.
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