The chemical constituents of the essential oil from Cyperus kyllingia Endl. were analyzed by a GC, GC-MS. Twenty-three compounds were identified, accounting for 93.75% of the total oil that consisted mainly of oxygenated sesquiterpenes (53.52%), particularly sesquiterpene hydrocarbons (38.97%), and carboxylic acid (1.26%). The most representative compounds were α-cadinol (19.32%), caryophyllene oxide (12.17%), α-muurolol (11.58%), α-humulene (9.85%), and α-atlantone (6.07%). The oil showed significant activities against Plasmodium falcipalum (K1, multi drug resistant strain) and NCI-H187 (Small Cell Lung Cancer) with the IC50 values of 7.52 and 7.72 μg/mL, respectively. The oil exhibited highly active against Staphylococcus aureus ATCC25923 and moderately active against Escherichia coli ATCC25922, Pseudomonas aeruginosa ATCC27553, Aspergillus flavus and Candida albicans

Garson, Mary J.

Khamsam, Sorachai

Liawruangrath, Boonsom

Liawruangrath, Saisunee

Pyne, Stephen G.

Teerawutkulrag, Aphiwat

University of Queensland eSpace

University of Wollongong
Research Online
Faculty of Science - Papers (Archive) Faculty of Science, Medicine and Health
2011
Antimalarial, Anticancer, Antimicrobial activities
and chemical constituents of essential oil from the
aerial parts of Cyperus kyllingia Endl
Stephen G. Pyne
University of Wollongong, spyne@uow.edu.au
Boonsom Liawruangrath
Chiang Mai University
Saisunee Liawruangrath
Chiang Mai University
M Garson
University of Queensland
S Khamsan
Chiang Mai University
See next page for additional authors
Research Online is the open access institutional repository for the
University of Wollongong. For further information contact the UOW
Library: research-pubs@uow.edu.au
Publication Details
Khamsan, S., Liawruangrath, B., Liawruangrath, S., Teerawutkulrag, A., Pyne, S. G. & Garson, M. J. (2011). Antimalarial, Anticancer,
Antimicrobial activities and chemical constituents of essential oil from the aerial parts of Cyperus kyllingia Endl. Records of Natural
Products, 5 (4), 324-327.
Antimalarial, Anticancer, Antimicrobial activities and chemical
constituents of essential oil from the aerial parts of Cyperus kyllingia Endl
Abstract
The chemical constituents of the essential oil from Cyperus kyllingia Endl. were analyzed by a GC, GC-MS.
Twenty-three compounds were identified, accounting for 93.75% of the total oil that consisted mainly of
oxygenated sesquiterpenes (53.52%), particularly sesquiterpene hydrocarbons (38.97%), and carboxylic acid
(1.26%). The most representative compounds were -cadinol (19.32%), caryophyllene oxide (12.17%), -
muurolol (11.58%), -humulene (9.85%), and -atlantone (6.07%). The oil showed significant activities against
Plasmodium falcipalum (K1, multi drug resistant strain) and NCI-H187 (Small Cell Lung Cancer) with the
IC50 values of 7.52 and 7.72 g/mL, respectively. The oil exhibited highly active against Staphylococcus aureus
ATCC25923 and moderately active against Escherichia coli ATCC25922, Pseudomonas aeruginosa
ATCC27553, Aspergillus flavus and Candida albicans. Copyright Published 04 15/2011 EISSN: 1307-6167.
Keywords
Antimalarial, Anticancer, Antimicrobial, activities, chemical, constituents, essential, oil, from, aerial, parts,
Cyperus, kyllingia, Endl, CMMB
Disciplines
Life Sciences | Physical Sciences and Mathematics | Social and Behavioral Sciences
Publication Details
Khamsan, S., Liawruangrath, B., Liawruangrath, S., Teerawutkulrag, A., Pyne, S. G. & Garson, M. J. (2011).
Antimalarial, Anticancer, Antimicrobial activities and chemical constituents of essential oil from the aerial
parts of Cyperus kyllingia Endl. Records of Natural Products, 5 (4), 324-327.
Authors
Stephen G. Pyne, Boonsom Liawruangrath, Saisunee Liawruangrath, M Garson, S Khamsan, and A
Teerawutkulrag
This journal article is available at Research Online: http://ro.uow.edu.au/scipapers/3770
SHORT REPORT                                                                                     
 
The article was published by Academy of Chemistry of Globe Publications 
www.acgpubs.org/RNP © Published  04 15/2011 EISSN: 1307-6167 
 
 
 
 
Rec. Nat. Prod. 5:4 (2011) 324-327 
 
 
Antimalarial, Anticancer, Antimicrobial Activities and Chemical 
Constituents of Essential Oil from the Aerial Parts of  
Cyperus kyllingia Endl. 
 
Sorachai Khamsan1, Boonsom Liawruangrath1*, Saisunee Liawruangrath2, 
Aphiwat Teerawutkulrag2, Stephen G. Pyne3 and Mary J. Garson4  
 
1Faculty of Pharmacy, Department of Pharmaceutical Science, Chiang Mai University, Chiang Mai, 
50200 Thailand 
2Faculty of Science, Department of Chemistry and center for Innovation in Chemistry, Chiang Mai 
University,Chiang Mai, 50200 Thailand 
3Faculty of Science, Department of Chemistry,University of Wollongong, Wollongong, NSW, 2522 
Australia 
4School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, QLD, 4072 
Australia 
 
 (Received August 18, 2010; Revised March 28, 2011; Accepted March 31, 2011) 
 
Abstract:  The chemical constituents of the essential oil from Cyperus kyllingia Endl. were analyzed by a GC, 
GC-MS. Twenty-three compounds were identified, accounting for 93.75% of the total oil that consisted mainly 
of oxygenated sesquiterpenes (53.52%), particularly sesquiterpene hydrocarbons (38.97%), and carboxylic acid 
(1.26%). The most representative compounds were α-cadinol (19.32 %), caryophyllene oxide (12.17%), α-
muurolol (11.58 %), α-humulene (9.85%), and α-atlantone (6.07%). The oil showed significant activities against 
Plasmodium falcipalum (K1, multi drug resistant strain) and NCI-H187 (Small Cell Lung Cancer) with the IC50 
values of 7.52 and 7.72 µg/mL, respectively. The oil exhibited highly active against Staphylococcus aureus 
ATCC25923 and moderately active against Escherichia coli ATCC25922, Pseudomonas aeruginosa 
ATCC27553, Aspergillus flavus and Candida albicans.  
 
Keywords: Cyperus kyllingia Endl.; essential oil; antimalarial activity; anticancer activity; antimicrobial activity 
 
1. Plant Source 
 
Cyperus kyllingia Endl. (Cyperaceae) is commonly found in tropical regions of the world. 
According to ethnomedical investigation this plant was found to have numerous biological activities, 
such as antidiarrhoeal, diuretic, stomachic, anthelmintic and expectorant activities. It is also used in 
fever, hepatopathy, splenopathy, diabetes and tumors [1].  
                                               
*
 Corresponding author:  E-Mail: boonsom@pharmacy.cmu.ac.th; Phone: +66-53-944342-3;  Fax: +66-53-222741 
Khamsan, S. et al., Rec. Nat. Prod. (2011) 5:4 325-328 
  
 
325
The aerial parts of C. kyllingia Endl. were collected in July 2008 from Chiang Mai University, 
Thailand. The plant material was identified by J. F. Maxwell. A voucher specimen was deposited at 
the Herbarium of Chiang Mai University, Chiang Mai, Thailand (No. S. Khamsan 2).  
 
2. Previous Studies 
 
 The oils of C. brevifolius and C. kyllingia f. Humulis underground parts contain terpenes 
including α-cyperone, β-selinene and α-humulene [2]. More recently, the phytochemical investigation 
of the plant was found that the ethanolic extract of the rhizomes possesses flavonoids, triterpenoids 
and glycosides. The petroleum ether extract was found to possess triterpenoids and glycosides [1].  
 There is no report on chemical investigation and biological activities of the essential oil 
from C. kyllingia Endl.. This is the first report on chemical constituents and its biological activity.
  
3. Present Study 
 
The fresh aerial parts (500 g) were subjected to hydrodistillation in a modified Clevenger-type 
apparatus for 4 h. The oil was collected, dried over anhydrous Na2SO4 and stored at 4°C for further 
analysis. 
The oil was analyzed on a Hewlett-Packard GC-6850 gas chromatograph (FID) equipped with 
a HP-1 (HP 19091S-933E) fused silica capillary column, 30 m × 0.25 mm, 0.25 µm film thickness, 
programming from 80°C (4 min) to 260°C at 8°C/min, 20 min hold, ending at 260°C (15 min); carrier 
gas He, constant flow rate of 20.0 mL/min; injector port and detector temperature were 250°C and 
280°C, respectively. Samples were injected by splitting mode (1:20).  
The GC-MS analysis was performed on Hewlett-Packard 6850GC coupled with a Hewlett-
Packard 5973N mass selective detector under the same conditions as for GC. Significant quadrupole 
MS operating parameters: interface temperature 240°C; electron impact ionization at 70 eV with scan 
mass range of 35-550 m/z at a sampling rate of 1.0 scan/s; carrier gas He, constant flow rate of 1.0 
mL/min and the split ratio was 1:20.  
The components of the oil were identified by comparing of their retention indices (RI) relative 
to n-alkane indices on HP-1 column and by a comparison of mass spectra from libraries (Wiely7n.1 
and NIST) with literature data [5-9].  
Antimalarial activity against P. falcipalum (K1) was determined by microculture radioisotope 
techniques (Desjardins et al.) [3]. The anticancer activity against the NCI-H187 was performed using 
the method described by Brien et al. [4]. The preliminary antimicrobial activities were also evaluated 
using the agar diffusion method. The microorganisms used were: Escherichia coli ATCC25922, 
Staphylococcus aureus ATCC25923, Pseudomonas aeruginosa ATCC27553, Candida albican, 
Aspergillus flavus and Trichophyton mentagrophyte.  
The qualitative and quantitative analysis of the essential oil were listed in order of elution in 
the HP-1 column (Table 1) with a yielded of 0.26% (w/w). In total, 23 compounds were identified, 
corresponding to 93.75% of the total oil that consisted mainly of oxygenated sesquiterpenes (53.52%) 
particularly sesquiterpene hydrocarbons (38.97%), and carboxylic acid (1.26%) including α-cadinol 
(19.32%), caryophyllene oxide (12.17%), α-muurolol (11.58%), α-humulene (9.85%), and α-
atlantone (6.07%) as the major components. 
The oil showed significant activities against P. falcipalum (K1) and NCI-H187 (Small Cell 
Lung Cancer) with the IC50 values of 7.52 and 7.72 µg/mL, respectively (Tabel 2). The potent 
activities of the oil might be attributable to its high sesquiterpene content (92.49%). The bioactivity of 
some sesquiterpenes present in this essential oil has been reported that α- cadinol, α-humulene and 
β−caryophyllene exhibited anticancer activity [10].  
 
 
Essential oil from Cyperus kyllingia Endl. 
 
326
 
Table 1 Chemical constituents of C. kyllingia Endl. essential oil 
Compound HP1a DB5b % Identificationc References 
Sesquiterpene hydrocarbons      
α−Cubebene 1353 1351 1.11 RI, MS [5] Fraternale et al., Fitoterapia. 
(2007) 78, 443−335.  
α−Copaene 1370 1377 1.01 RI, MS [6] Vian et al., J. Chromatogr. A. 
(2008) 1190, 14−17.  
β−Bourbonene 1379 1388 0.74 RI, MS [6] 
β−Elemene 1387 1391 3.78 RI, MS [6] 
β−Caryophyllene 1415 1419 1.43 RI, MS [6] 
α−Humulene 1464 1455 9.85 RI, MS [5] 
γ−Muurolene 1474 1477 0.86 RI, MS [5] 
Germacrene D 1493 1480 5.51 RI, MS [5] 
β−Selinene 1496 1485 2.26 RI, MS [5] 
α−Valencene  1490 1496 3.09 RI, MS [5] 
α−Muurolene 1498 1500 2.26     RI, MS [7] Bendimerad et al., J. Agric. 
Food Chem. (2005) 53, 2947−2952.  
γ-Cadinene 1500 1511 0.63 RI, MS [7] 
(Z)-Calamenene 1509 1512 0.76 RI, MS [8] 
δ−Amorphene 1519 1518 4.20 RI, MS [8] 
δ−Cadinene 1528 1523 1.48 RI, MS [5] 
Oxygenated sesquiterpenes      
Spathulenol 1567 1578 0.81 RI, MS [6] 
Caryophyllene oxide 1572 1581 12.17 RI, MS [6] 
Τ−Muurolol 1627 1608 1.8 RI, MS [8] Boyom et al., Phytochemistry. 
(2003) 64, 1269−1279.  
α− Muurolol  1628 1645 11.58 RI, MS [8] 
α− Cadinol  1639 1653 19.32 RI, MS [8] 
α−Atlantone 1679 1717 6.07 RI, MS [8] 
Farnesol 1691 1746 1.77 RI, MS [8] 
Carboxylic acid      
Palmitic acid 1940 1963 1.26 RI, MS [7] 
Sesquiterpene hydrocarbons   38.97   
Oxygenated sesquiterpenes   53.52   
Carboxylic acid   1.26   
Total   93.75   
aRI retention indices on HP1 column; relative to n-alkane, bRI retention indices on DB5 column [9]: Adams 
(2001), c Methods of identification: MS, comparison of the mass spectrum with MS libraries; RI of literature. 
  
Table 2 Antimalarial and anticancer activity of C. kyllingia Endl. essential oil 
Sample IC50a (µg/mL) 
P. falciparum (K1)                         NCI-H187 
C. kyllingia Endl. oil 
Dihydroartemisininb 
Ellipticinec 
Doxorubicined 
7.52 
0.0012 
- 
- 
7.72 
-                           
1.18 
0.058 
 aConcentration that killed 50% of cell lines,  bAntimalarial drug used as positive control 
c,d
 Anticancer drug used as positive control  
The oil possessed strong antimicrobial activity against S. aureus and showed moderately 
active against all bacteria and fungi strains with their respective diameter of the inhibition zones 
(Table 3), but did not inhibit the growth of T. mentagrophyte. 
Khamsan, S. et al., Rec. Nat. Prod. (2011) 5:4 325-328 
  
 
327
According to this result the essential oil of C. kyllingia Endl. exhibited significant antimalarial, 
anticancer and antimicrobial activites. Thus, essential oil from this plant might be another potential 
source for the discovery of new drugs to treat infectious diseases. 
 
Table 3 Antimicrobial activity of C. kyllingia Endl. essential oil 
Sample test Concentration 
 
Zone of inhibition (mm)a 
Bacteria strains Fungi strains 
E. 
coli 
S. 
aureus 
P. 
aeruginosa 
A. 
flavus 
C. 
calbican 
T. 
mentagrophyte 
Oil 10 mg/mL 15 25 15 12 16 - 
10%  DMSOb - - - - - - - 
Gentamicinc 75 µg/mL 27 35 27 - - - 
Ketoconazoled 250 µg/mL - - - 25 37 16 
a
 Diameter of inhibition zones (mm); bNegative control;  c,dAntibiotic used as positive control   
 
Acknowledgments 
The authors gratefully acknowledge to Commission on Higher Education and Graduate School 
Chiang Mai University for financial support.  
 
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[8]  F. F. Boyom, V. Ngouana, P. H. Amvam Zollo, C. Menut, J. M. Bessiere, J. Gut and P. J. Rosenthal (2003). 
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