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Chemical Composition of Essential Oil from the Rhizomes and Leaves of


Newmania sontraensis H.Ð.Trân, Luu & Škornick (Zingiberaceae) from
Vietnam

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DOI: 10.1080/0972060X.2022.2026253

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Chemical Composition of Essential Oil from the


Rhizomes and Leaves of Newmania sontraensis
H.Ð.Trân, Luu & Škornick (Zingiberaceae) from
Vietnam

Doan Quoc Tuan, Dinh Dien, Ty Viet Pham, Thang Quoc Le, Duc Viet Ho, Le
Trong Nhan, Le Tuan Anh, Phung Thanh Huong & Nguyen Thi Hoai

To cite this article: Doan Quoc Tuan, Dinh Dien, Ty Viet Pham, Thang Quoc Le, Duc Viet Ho, Le
Trong Nhan, Le Tuan Anh, Phung Thanh Huong & Nguyen Thi Hoai (2021) Chemical Composition
of Essential Oil from the Rhizomes and Leaves of Newmania�sontraensis H.Ð.Trân, Luu & Škornick
(Zingiberaceae) from Vietnam, Journal of Essential Oil Bearing Plants, 24:6, 1260-1268, DOI:
10.1080/0972060X.2022.2026253

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J. Essent. Oil-Bear. Plants 24 (6) 2021 pp 1260 - 1268 1260

Journal of Essential
Oil-Bearing Plants
ISSN: 0972-060X (Print); ISSN: 0976-5026 (Online) https://www.tandfonline.com/loi/teop

Article

Chemical Composition of Essential Oil from the Rhizomes and Leaves


of Newmania sontraensis H.Ð.Trân, Luu & Škornick (Zingiberaceae) from
Vietnam

Doan Quoc Tuan 1, Dinh Dien 2, Ty Viet Pham 3, Thang Quoc Le 3, Duc Viet
Ho 1, Le Trong Nhan 1, Le Tuan Anh 4, Phung Thanh Huong 5, Nguyen Thi
Hoai 1*

1
Faculty of Pharmacy, Hue University of Medicine and Pharmacy, Hue University,
06 Ngo Quyen, Hue City, Viet Nam
2
Faculty of Forestry, Hue University of Agriculture and Forestry, Hue University,
102 Phung Hung, Hue City, Vietnam
3
Faculty of Chemistry, University of Education, Hue University, 34 Le Loi, Hue
City, Vietnam
4
Mientrung Institute for Scientific Research, Vietnam National Museum of
Nature, VAST, Hue 530000"
5
Hanoi University of Pharmacy, 13-15 Le Thanh Tong Street, Hanoi, Vietnam
* Corresponding Author: nthoai@hueuni.edu.vn (Nguyen Thi Hoai)
Received 16 August 2021; Received in revised form 28 December 2021; Accepted 05 January 2022

Abstract: This research aims to identify the volatile compounds from rhizomes and leaves of Newmania
sontraensis. The constituents of essential oil from the rhizomes and leaves of N. sontraensis were analyzed by
Gas Chromatography-Mass Spectrometry (GC/MS). Thirty-one compounds were identified in the rhizomes
compared to the leaves which showed thirty-two volatile compounds corresponding to 83.28 % and 76.41 % of
the oil content, respectively. The chemical composition of the rhizome oil was characterized by hydrocarbon
monoterpenes accounting for 36.26 %. The major compounds found in the rhizome oil included β-pinene (22.41
%), 1,8-cineole (8.32 %), bicyclogermacrene (6.94 %), α-terpinyl acetate (5.74 %), α-pinene (5.71 %), and camphene
(5.58 %). Meanwhile, sesquiterpene hydrocarbons were the main compounds found in the leaf oil accounting
for 54.18 %. Bicyclogermacrene (14.60 %), δ-elemene (9.89 %), β-elemene (7.26 %), and α-terpinyl acetate (4.27
%) were determined to be the main components found in leaf oil. This was the first report on the chemical
constituents of essential oils from rhizomes and leaves of N. sontraensis.
Keywords: Newmania sontraensis, essential oil, β-pinene, 1,8-cineole, bicyclogermacrene.

Introduction Southeast Asia and can be found in a variety of


Zingiberaceae is the largest family of the order forest ecosystems ranging from lowlands to high
Zingiberales comprising 53 genera and more than mountainous areas 1,2. Most of the members of
1600 species. It is distributed in tropical and Zingiberaceae are perennial rhizomatous herbs
subtropical areas 1,2. The greatest concentration that grow on the ground in moist shady regions.
of ginger species occurs in the islands of Several species are well-known as spices, medi-
J. Essent. Oil-Bear. Plants 2021, 24, 1260-1268 © 2021 Har Krishan Bhalla & Sons
DOI: 10.1080/0972060X.2022.2026253
Doan Quoc Tuan et al. / J. Essent. Oil-Bear. Plants 24 (6) 2021 pp 1260 - 1268 1261
cinal plants, food, cosmetics, and decoration 3. Materials and methods
There are more than 144 species of Zingiber- The rhizomes (0.5 kg) and leaves (0.5 kg) of N.
aceae belonging to 19 genera found in Vietnam 4. sontraensis H.Ð.Trân, Luu & Škornick were
In recent years, several new Zingiberaceae species collected from Phong Dien district, Thua Thien
have been discovered in Vietnam 5-16. The chemi- Hue province in February 2021 (16°28’1.10" N
cal compositions of essential oils have only been 107°20’3.35E), identified by Dr. Nguyen Tien
studied for one of these species 17,18. Most of the Chinh, Viet Nam National Museum of Nature. A
essential oil from Zingiberaceae is extracted from voucher specimen (PD-T121) was deposited at
rhizomes and leaves 2 and the common technique the Faculty of Pharmacy, Hue University of
for extracting essential oil from these species is Medicine and Pharmacy, Hue University, Viet
hydrodistillation. Numerous constituents from Nam.
essential oils (EO) of Zingiberaceae have been
reported previously including terpenes, ketones, Hydrodistillation of the essential oils
alcohols, phytoestrogens and flavonoids 19. In this process, the fresh rhizomes and leaves of
Newmania Ngoc Sâm Lý & Škornicková is a N. sontraensis were separately hydrodistilled using
new endemic Vietnamese ginger genus that was a Clevenger-type apparatus according to speci-
first discovered and illustrated in 2011 by com- fication 21. The distillation time was three hours
paring morphological characters and analyzing at normal pressure. The essential oils were treated
molecular structures 5. Up to now, six species with anhydrous sodium sulfate to remove moisture
have been described from central Vietnam, namely content and kept in the refrigerator at 4oC until
N. rthostachys, N. serpens, N. sessilanthera, N. further analysis. Each experiment was repeated
cristata, N. gracilis and N. sontraensis 13 . in triplicate.
Therein, N. sontraensis H.Ð.Trân, Luu &
Škornick is a new ginger species that was recorded Analysis of the essential oils
in 2018 in Central Vietnam 13. N. sontraensis is a The chemical composition of the essential oil was
terrestrial herb found in the forests of central analyzed using the GCMS-QP2010 Plus system
Vietnam. Most of the specimens of N. sontraensis (Shimadzu, Kyoto, Japan) equipped with Equity-
were seen in the evergreen forest at 250 to 660 5 capillary column (30 m × 0.25 mm, 0.25 μm film
m above sea level. N. sontraensis has the follow- thickness) and coupled with a mass spectrometer
ing morphological characteristics: 160 cm tall with (MSD QP2010 Plus) used for GC/MS analysis.
2-5 leafy shoots per rhizome; subterranean The oil was diluted with n-hexane in a ratio of
rhizome, branched, light-brown externally, cream 1:100, and 1 μL was used for analysis. The analyti-
white internally; N. sontraensis flowers are cal conditions were as follows: carrier gas helium
cream white with a dark red-purple reticulate (1.5 mL/min), injector temperature of 280°C,
pattern (pedicel and ovary 8-10.5 cm long), interface temperature of 280°C, and a column
flowering was recorded beginning in April, temperature programmed from 60°C (2 min hold)
fruiting in May and may extend to throughout to 240°C at 3°C/min (10 min hold) and then
June; inflorescence rises from the rhizome at the increased to 280°C at 5°C/min (40 min hold).
base of the leafy shoot. It was provisionally Samples were injected using a splitless mode. The
proposed to treat N. sontraensis as Endangered, MS conditions were as follows: ionization voltage
B1ab(iii) +2ab(iii) 13,20 . Remarkably, since 70 eV; acquisitions scan mass range of 45-500
Newmania was discovered and recorded in 2011, (m/z) at a sampling rate of 1.0 scan/s. The retention
no chemical data on the essential oil compositions indices (RI) of constituents were determined by
of this genus including N. sontraensis, has been co-injection with reference to a homologous series
reported. This is the first study on the chemical of n-alkanes (C8 - C38) under the same conditions.
compositions of essential oils from the rhizomes The identification of components was carried
and leaves of N. sontraensis collected in out by comparison of their RI values with those in
Vietnam. the literature 22. Further identification was
Doan Quoc Tuan et al. / J. Essent. Oil-Bear. Plants 24 (6) 2021 pp 1260 - 1268 1262
performed by comparison of their mass spectra α-pinene (5.71 %), and camphene (5.58 %). On
with those from NIST 11 and WILEY 7 stored in the contrary, sesquiterpene hydrocarbons were the
the GC/MS database. Quantification was main type in the leaves with nineteen components
performed using the relative peak area percentage. that account for 54.18 % of the oil content. The
dominant constituents were found as bicyclo-
Results and discussion germacrene (14.60 %), δ-elemene (9.89 %), β-
The yields of essential oils, based on fresh weight elemene (7.26 %), and α-terpinyl acetate (4.27
(w/w) from the rhizomes and leaves of N. %). Most of the major substances in the rhizome
sontraensis were 0.11 ± 0.02 % and 0.06 ± 0.02 essential oils are present in the leaf essential oils,
%, respectively. The essential oils of both parts except for α-pinene (Table 1). A significant amount
were obtained as pale-yellow liquid with a charac- of β-pinene (22.41; 3.05 %), bicyclogermacrene
teristic odor and lighter density than water. (6.94; 14.60 %) and α-terpinyl acetate (5.74; 4.27
The GC/MS analysis indicated that the number %) was identified in both oils.
of constituents identified in the essential oil from β-Pinene is a bicyclic monoterpene isomer, found
the rhizomes and leaves of N. sontraensis was in many plants and this is the main component of
thirty-one and thirty-two, accounting for 83.28 % various essential oils, such as Pinus spp., Piper
and 76.41 % of the whole composition, respecti- spp, Santiria trimera, Hornstedtia bella 23-27.
vely (Table 1). The constituents were classified β-Pinene against Candida strains with MIC values
into five groups based on their structures, including from 56.25 to 1800 μmol/L, Staphylococcus
monoterpene hydrocarbons, oxygenated mono- aureus (MRSA) with the MIC value of 6.25 μg/
terpenes, sesquiterpene hydrocarbons, oxygenated mL 28,29. The essential oil from Piper aequale
sesquiterpenes, and other compounds. The mono- containing β-pinene (15.56 %) and α-pinene
terpene hydrocarbons (36.26 %) were the most (12.57 %) exhibited strong cytotoxic activity
abundant class identified in the rhizomes, whereas against the human cancer cell lines HCT-116 and
these compounds only accounted for a very small ACP03 with IC50 values of 8.69 and 1.54 μg/mL,
proportion (4.44 %) in the leaf oil. The major respectively 25 . The essential oil of Salvia
compounds were found in rhizome oil including aramiensis with 10.3 % β-pinenes demonstrated
β-pinene (22.41 %), 1,8-cineole (8.32 %), bicyclo- DPPH inhibition with an IC50 value of 12.2 ± 1.0
germacrene (6.94 %), α-terpinyl acetate (5.74 %), μg/mL30. Furthermore, β-pinenes has shown an

Table 1. Chemical composition of the essential oil


from the rhizomes and leaves of N. sontraensis

Concentration(%)
No. Compoundsa RT RI b RI c Rhizome Leaf

1 α-Pinene 6.769 932 929 5.71 0.56


2 Camphene 7.247 946 944 5.58 0.41
3 β-Pinene 8.389 974 981 22.41 3.05
4 Myrcene 8.659 988 990 1.05 0.2
5 Limonene 10.038 1024 1026 - 0.78
6 1,8-Cineole 10.230 1026 1031 8.32 0.64
7 γ-Terpinene 11.260 1054 1057 0.57 -
8 Terpinolene 12.492 1086 1088 0.94 -
9 α-Terpineol 17.001 1186 1191 1.28 -
10 Geraniol 19.839 1249 1255 0.7 -
11 Isononyl acetate 21.212 1283 1286 0.95 -
12 δ-Elemene 23.574 1335 1329 1.28 9.89
Doan Quoc Tuan et al. / J. Essent. Oil-Bear. Plants 24 (6) 2021 pp 1260 - 1268 1263
table 1. (continued).

Concentration(%)
No. Compoundsa RT RI b RI c Rhizome Leaf

13 α-Terpinyl acetate 23.696 1346 1341 5.74 4.27


14 α-Copaene 25.130 1374 1377 0.22 0.64
15 β-Elemene 25.930 1389 1393 1.2 7.26
16 α-Gurjunene 26.541 1409 1410 0.34 0.71
17 (E)-Caryophyllene 26.968 1417 1421 1.52 4.62
18 γ-Elemene 27.571 1434 1435 - 0.63
19 α-Guaiene 27.776 1437 1440 - 0.78
20 α-Humulene 28.388 1452 1455 1.56 1.48
21 allo-Aromadendrene 28.735 1458 1462 - 3.16
22 10-epi-β-Acoradiene 29.373 1474 1479 0.85 2.54
23 β-Selinene 29.832 1489 1488 0.57 3.57
24 Bicyclogermacrene 30.272 1500 1501 6.94 14.60
25 (E,E)-α-Farnesene 30.638 1505 1510 - 2.05
26 γ-Cadinene 30.897 1513 1517 - 0.60
27 δ-Cadinene 31.267 1522 1526 1.26 1.65
28 Germacrene D-4-ol 33.346 1574 1580 - 1.57
29 Spathulenol 33.427 1577 1581 2.13 1.04
30 Thujopsan-2-β-ol 33.637 1588 1587 - 1.41
31 Globulol 33.631 1590 1587 1.94 -
32 Viridiflorol 33.928 1592 1594 1.56 0.59
33 Ledol 34.355 1602 1605 0.95 0.76
34 β-Oplopenone 34.571 1607 1611 - 0.63
35 β-Acorenol 35.701 1636 1642 1.21 -
36 epi-α-Muurolol 35.825 1640 1645 - 1.11
37 epi-α-Cadinol 36.321 1640 1646 1.75 1.96
38 α-Cadinol 36.346 1652 1659 2.53 -
39 ar-Turmerone 36.646 1668 1667 0.64 -
40 n-Tetradecanol 37.023 1671 1677 - 0.51
41 5-neo-Cedranol 36.868 1683 1673 0.85 -
42 (Z)-β-Santalol acetate 42.293 1818 1826 0.9 -
43 Phytol 51.587 2116 2111 2.74
Total number of constituents/% identify 31 32
Monoterpene hydrocarbons (Sr. no. 1-5, 7, 8) 36.26 5.00
Oxygenated monoterpene (Sr. no. 6, 9,10) 10.30 0.64
Sesquiterpene hydrocarbons (Sr. no. 12, 14-27) 15.57 54.18
Oxygenated sesquiterpenes (Sr. no. 28-39, 41) 13.56 9.07
Others (Sr. no.11, 13, 40, 42, 43) 7.59 7.52
Total 83.28 76.41

a
Elution order on Equity-5 column
b
Retention Indices on Equity-5 column
c
Literature retention indeices
RT retention time on Equity-5 column
- Not identified
Doan Quoc Tuan et al. / J. Essent. Oil-Bear. Plants 24 (6) 2021 pp 1260 - 1268 1264
insecticidal activity against the fly Musca domes- contaning β-elemene (10.0 %) displayed anti-
tica, the fruit fly Bemisia argentifolii, and cock- microbial activity against the bacteria Staphylo-
roaches 31. Bicyclogermacrene is a sesquiterpene coccus aureus and Escherichia coli with MIC
derived from germacrene. It is the main value of 112.5 μg/mL and 225 μg/mL respectively
component in essential oils of species such as 42
. The essential oil from leaves of Croton hetero-
Annona spp., Piper spp., Lantana camara, and calyx containing δ-elemene and β-elemene with
Nectandra leucantha 32-35 . According to 9.2 % and 8.2 %, respectively, showed a strong
Emmanoel et al., Annona vepretorum oil contains growth inhibition against the bacterium Staphylo-
43.7 % bicyclogermacrene and the essential oil coccus aureus and the fungi Candida albicans
displayed a potent trypanocidal activity (IC50 value and Aspergillus niger with MIC value of 91.6
of 31.9±1.3 μg/mL) and antimicrobial activity μg/mL, 100 μg/mL and 73.4 μg/mL, respectively
against Candida tropicalis (MIC value of 100 43
. Besides, δ-elemene were demonstrated strong
μg/mL) 36. The essential oils of leaves and flowers cytotoxic activity against Hela, DLD-1 and HL-
from Annona cherimola have shown inhibition 60 cell lines with IC50 values of 157.9 μM, 159.8
against Staphylococcus aureus and Entero- μM and 200 μM, respectively 44-46. 1,8-Cineole
coccus faecalis with MIC value of 0.125 - 0.5 (cineole) is a terpenoid oxide present in many plant
mg/mL and the major constituents in this essential essential oils especially, Eucalyptus, Rosemary,
oil contain 11.73 - 18.2 % bicyclogermacrene 37. and Psidium 47. Previous research has shown that
Simone et al. reported that bicyclogermacrene and 1,8-cineole from essential oils of Eucalyptus
Nectandra leucantha oil displayed significant nicholii, Melaleuca fulgens, Callistemon sieberi,
cytotoxic activity against HeLa (IC50 of 12.4 ± Eucalyptus blakelyi, and Melaleuca armillaris
0.3 and 60 ± 12 μg/mL, respectively), B16F10- with high 1,8-cineole concentration (82.19 %,
Nex2 (IC 50 of 3.1 ± 0.2 and 33 ± 1 μg/mL, 77.50 %, 58.99 %, 56.92 % and 42.77 % respecti-
respectively), and U87 (IC50 of 6.7 ± 0.4 and 75.95 vely) have potent fumigant toxicity against three
± 0.03 μg/mL, respectively) 35. The essential oil stored-grain insects Sitophilus oryzae, Tribolium
from Schinus terebinthifolius leaves with castaneum and Rhyzopertha dominica with
bicyclogermacrene (15.0 %) showed cytotoxic LD50 and LD95 value between (19.0-30.6 ml/l and
effects in several cell lines, including B16F10- 43.6-56.0 ml/l; 13.7-17.4 ml/l and 16.5-20.3 ml/l;
Nex2, A2058, MCF7, HL-60, and HeLa with MIC 7.8-10.4 ml/l and 14.3-21.1 ml/l, respectively) 48.
values of 38.0 ± 0.1, 40.1 ± 0.2, 40.2 ± 0.5, 45.3 ± Furthermore, 1,8-cineole can attenuate cerulein-
0.2, and 20.0 ± 0.1, respectively 38. The essential induced acute pancreatitis via an anti-inflammatory
oil of Lantana camara contains bicyclo- mechanism and has been effective against
germacrene (19.42 %) showed inhibitory activity influenza virus infection in mice via attenuation of
to Escherichia coli (MIC value of 512 μg/mL) pulmonary inflammatory responses 49,50. In addition,
and Staphylococcus aureus (MIC value of 256 the antiseptic properties of chlorhexidine gluconate
μg/mL) 39. Elemene is a natural sesquiterpene and (CHG) increased when combined with 1,8-cineole
its isomers were isolated from the Chinese herbal 51
.
medicine plant Curcuma sp.40. Without Curcuma In summary, in the present work, we identified
sp. species, essential oils from Nigella the chemical compositions of essential oils from
damascena L., Magnolia figo (Lour.) DC, N. sontraensis with major components of potential
Alisma orientalis Sam. and Solidago decurrens biological activities such as α-pinene, β-pinene,
Lour are also the rich source β-elemene and its 1,8-cineole, bicyclogermacrene, β-elemene and δ-
isomers δ-elemene 40. The essential oil of Nigella elemene. However, we have not studied the
damascena containing β-elemene (47.37 %) biological activities of these essential oils. Instead,
showed antibacterial activity against the bacteria the current research provides an overview of the
Mycobacterium tuberculosis H37Ra with MIC chemical compositions of N. sontraensis oils.
value of 256 μg/mL41. Another study showed that Hence, there remains a range of experiments that
essential oil from Hornstedtia havilandii can be implemented in future studies, such as
Doan Quoc Tuan et al. / J. Essent. Oil-Bear. Plants 24 (6) 2021 pp 1260 - 1268 1265
investigating the pharmacological effects of the cineole (8.32 %), bicyclogermacrene (6.94 %),
oils and main components of N. sontraensis to α-terpinyl acetate (5.74 %), α-pinene (5.71 %),
confirm and build upon the encouraging results of and camphene (5.58 %), while the leaf oil was
this work. There is significant opportunity to dominated by bicyclogermacrene (14.60 %), δ-
expand upon this analysis of essential oils found elemene (9.89 %), β-elemene (7.26 %), and α-
in the rhizomes and leaves of N. sontraensis. terpinyl acetate (4.27 %). This study is reporting
these results for the first time.
Conclusion
The chemical constituents of essential oils from Acknowledgments
the rhizomes and leaves of N. sontraensis from We are grateful to Dr. Vu Tien Chinh (Viet Nam
Vietnam have been identified with thirty-one and National Museum of Nature) for identifying the
thirty-two constituents accounting for 83.28 % and scientific name of Newmania sontraensis and
76.41 %, respectively. The major constituents of Dr. Megan Butler (Lake Superior State University
the rhizome oil were β-pinene (22.41 %), 1,8- - USA) for language checking and editing.

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