' i !

Cymbopogon citratus

Chapter-4 CYM BOPOGON CITRA TUS

CYM BOPOGONCITRATUS(DC.) STAFF.

( P O A C E A E )

Cvmbopogon is an important genus o f aromatic grasses belonging to the family Poaceae

with about 140 species and many varieties having a varied combination of both terpcnes

and non-terpenes phenolic constituents in their essentia! oils which are used in

perfumery, cosmetics and pharmaceutical and flavouring industries, 'fliere exist a lot o!'

genetic variability in naturally occurring Cymhopogon with respect o f oil yield, herb

yield, oil quality and chemical constituents. The chemical composition of this genus is

not species specific. Same species o f different localities may have different constituents

and different species having different geographical distribution have similar constituents

in their oil (Anonymous, 2000). The genus Cymbopogon has been divided into three

series, i.e., Schoenanthi, Rusae and Citrati. based on the nature o f their essential oils

(Handaand Kaul, 1996).

Synonym s

Andfopogon d tra tus DC., lemongrass

V ernacu lar Nam es

Bengali Gandhabena

Mindi Gandhatrina

Punjabi Kliawi

Sanskrit Abiclihatraka, Aligandha, Bhustrina, Badhira,

Tamil Karpurappillu, Vasanapillu

Telugu Chippagaddi, Nimmagaddi

Malayalam Vasanappula, Shanbarapulla

English Lemongrass, Melissagrass

Gujarati Lilacha, Lilicha (Kirtikar and Basu, 2(

37

P is ir ib u tion

Cymbopogon species are generally distributed in tropical and sub-tropical regions

(Ekundayo, 1985), In India, Cymbopogon are known to grow in the wild state in all

regions extending frotn sea level to 4,200 rn high where there is abundant rainfall.

Several species are endemic to India. The habitat diffcrcnce affects the vitality, life span,

yield and quality o f oil (Anonymous, 2000).

cUratiis is considered to be o f Indian origin but is now distributed over the tropics o!'

both the hemispheres. It is only known in cultivated state. In India, it is cultivated in

Kerala and the region along the western coast o f India (Handa and Kaul, 1996 ; Kii'tikar

and Basu, 2000).

Tw'o types of lemongrass oil are recognised in commerce:

(i) East Indian or Cochin lemongrass oil obtained from C. jlexiiosus Stapf and is also

known as Malabar or Cochin grass and is indigeneous to India.

(ii) West Indian lemongrass oil obtained from C. ciuxtfus Stapf.

Both oils contain 75-85% of aldehydes, chiefly citral, but they differ slightly in that the

East Indian oil is usually less soluble in 70% alcohol than the W est Indian oil. The low'er

solubility o f the latter is due to the presence o f myrcene (Virrnani et a i , 1979).

M orphology

The name Cymbopogon is derived from two Greek words ‘Kymbe’ meaning a boat and

‘Pogon’ meaning a beard, the first one refers to the boat shape spatheolcs that arc a

conspicuous feature of the inflorescences while the second refers to the many awned

infloresence.

C. citratus is a large, coarse, glaucous, perennial, densely tufted grass, It is tall perennial,

throwing up dense fascicles o f leaves from a short; oblique annulate, sparingly branched

rhizome, usually barren, but occasionally giving rise to a stout erect culm up to over 1.8

metre high, 7-8 noded and simple below the panicle. Leaf blades linear, long attenuated

towards the base and tapering upwards to a long setaceous point, up to over 90 cm long

by 16-18 mm wide, very firm, glaucous green, glabrous, smooth or more or less rough

upwards and along the margins ; midrib somewhat stout below, whitish on the upper side.

Chapter-4 CYMBOPOGON C ITIU TU S

38

The panicles are 30-80 cm long, interrupted below the branchlets and branches are

soemwhat nodding. The perfect spikeiets are linear, lanceolate, pointed, not awned, and

about 6 cm long (Barnabas, 1981; Kirtikar and Basu, 2000).

Cliemicsil Com position

Lemongrass oil is a yellow or amber liquid obtained by distillation o f air-dried leaves o f

C.citrates. Oil contains 75-85 % of aldehydes, chiefly citral (Virmani et al., 1979), The

percentage o f citral varies with locality. Essential oil content varies with the age ttf tlie

grass ; optimum age 18-24 months giving oil with citral content 71-75%. Dry material

yields 0.4% essential oil content with 72.3% citral (Chopra el al., 1956). The odour o f

lemongrass oil is basically lemon-like and is ascribed to aldehyde citral ('Forres and

Ragadio, 1996)

By using a combination o f gas chromatography and mass spectrometry the chemical

composition o f hidian lemongrass oil w as, determined as: rayrcene (1.5%), citronellol

(1.5%), methylheptenone (0,2%), nero! (0.8%), linalool (1.2%), geranly Acetate (1.8%o),

linalyl acetate (0.1%), neral (43.50%), 2-undecanone (0.3%), geranial (28.8%), geranyl

Acetate (0.1%) (Zamureenko et al. 1981; Lawrcnce, 1984)

Two triterpenoids were isolated from leaf wax o f C.citratus a ketone, cymbopogoiie, and

an alcohol, cymbopogonol (Hanson e/« /., 1976).

Flavonoids were isolated from the alcoholic concentrate o f fresh aerial parts o f C.

citratm. They were identified as luteolin and its 6-C-glucoside. This was the first record

of isolation o f glycotlavones; although their presence has been indicated before

(Barnabas et a l , 1981).

Composition o f oil o f the Ethiopian C. citratus is quite different from all the other

reported geographical varieties and is more comparable in constitution to the oil of C.

nardus. It contains geraniol (40%) as the main constituent and only 13% citral. Second

major component was a-oxobisabolene (12%), Menthone and iiienthol, rarely found in

other varieties, were found in low quantities (Abegaz and Yohannes, 1983).

Ekundayo (1985), found that the citral (neral and geranial) contents o f N igerian grown C.

citratus was 57% o f the oil, which is relatively lower than the 70% or more recorded for

the African samples. He also reported the presence o f two non-terpenoid compounds, 6-

Chapter-4 CYM BOPOGON CITRA TUS

39

methyl"5-hepten-2"One and 3-methyl-2-heptanone, the latter was reported as a natural

product for the first time.

Ayoub and Yankov (1984) found that exposure to sunlight progressively increased the oil

content in the leaves of Sudanese C. citraliis. The citral content was maximum on the

fifth day o f drying. In emother study by Martins et al. (2002), it was shown that drying at

60 C increased the oil yield by 21% whereas a 5% increase in citral content was observed

al 40 C. The drying air velocity did not effect the oil content and amount o f citral.

An exi:ieriment was carried out to study essential oil content in different parts ol'

lemongrass. The essential oil contents o f the leaf blade and leaf sheath were 0.42 and

0.13%, respectively. Mean citral contents of the blade and sheath essential oils were

87.28 and 82.39%, respectively. In the leaf blade, essential oil droplet were observed in

the epidermis and mesophyll cells, and at a lower frequency in the buliform cells and

phloem, hi the leaf sheath, droplets were observed in parenchyma cells, phloem tissue

and in idioblast. (Ming et a l, 1996).

Chemical analysis o f essential oil o f Philippine C. citraius was carried out and citral was

identified as the main component with 69.39% concentration (Torres et a l , 1996).

The yield o f leaf oil from Zambian C. dtratus was 3.0%. It contained geranial (39%o) and

neral (29.4“/o) which together represent 68.4% of citral in the oil, as major component,

followed by myrcene (18%). The content o f citral (68,4'M)) was less than the minimum

requirement (75%) (Chisowa et a l, 1998).

The major components from C citratus cultivated in Zimbabwe were geranial (37.7-

41.3%), neral (30.0-33.4%)) and myrcene (5.6-18.6%). Geranial (2.5-6.7%) was a notably

minor component. The corresponding yield was 0.4-0.6%) (v/w). The total citral content

was 70.9-73.l%o (Chagonda et a l , 2000).

Lewinsohn et a l (1998) found that single parcnchymatous oil bearing cells were found

embedded in the adaxial side o f the leaf mesophyll. Citral accumulation only occurred in

particular single cells. The leaves yielded essential oil o f which the major components

were citral (71%), myrcene(50%o) and geraniol (5%).

Chapter-4 ____________ CYM BOPOGON CITRATUS

40

Medicina! Properties and Uses

The grass is pungent, bitter, sliarp, hot; laxative, appetizer alexipharmic, aphrodisiac,

anthelmintic; useful in bronchitis, leprosy, epileptic fits; causes burning sensation .In

flatulent and spasmodic affections o f the bowels, and in gastric irritability, the oil is a

remedy o f value. In cholera it proves serviceable, not only by allaying and arresting the

vomiting, but by aiding the process of reaction, When externally applied, it forms an

excellent embrocation in chronic rheumatism, neuralgia, sprains and other painful

affections (Anonymous, 2000),

In the Gold coast, the leaves are often boiled in water like tea and the liquor is drunk to

cure fever, It is sometimes put into hot bath water and the patient stands in the hot vapour

given off, This is a good cure for fever (Kirtikar and Basu, 2000; Bentley and Trinien,

2000 ).

An infusion of the fresh leaves on oral administration produced dose-dependent

analgesia in rats. The analgesic activity, caused by myrcene present in leaf essential oil,

supported the use o f lemongrass tea as a sedative in folk medicine. Leaf extract also

exhibited potential nematicidal activity. The essential oil from the leaves exhibit potential

anti-carcinogenic activity, d-limonene and geranial from oil induce the activity o f

glutathione S-transfera,se, a detoxifying enzyme, which is believed to be a m ajor factor

for chemical carcinogen detoxification (Anonymous, 2000).

Antibacterial property of the oil was studied by Onawunmi et al. (1984), geranial and

neral showed antibacterial acivity against E. coli, S. aureus and B. subtilis : but myrcejie

was only active against S. aureus. Myrcene enhanced the antibacterial activities o f

geranial and neral when combined with them. The leaves are used by the Cuban

population as an antihypertensive and antiinflammatory agent in folk medicine. A 10% or

20% decoction o f the leaves showed some dose-related hypertensive effects in rats when

given intravenously and some weak diuretic and antiinflammatory effects when given

orally (Carbajal et al., 1989).

Citral and citronellal constituents o f lemongrass oil showed good antifungal activity

while dipentene and myrcene exhibited no activity. Exposure o f the spores o f A.

fum igatus to 0,1% lemongrass oil for 5 mnutes resulted in 93% o f not germinated spores

(Onawunmi, 1989).

Chapter-4 CYM BOPOGON C JT M TV S

41

A herbal tea prepared from lemongrass leaves is not toxic and lacks hypnotic or

anxioiytic property (Leite et al., 1986).

Lemongrass oil is used in perfumery, flavouring and pharmaceutical preparations, Citral

is used for the synthesis o f ionones which leads to the formation o f vitamin A. lonones

are frequently used in perfumery, confectionary and liquors (Handa and Kaul, 1996).

Tlie spent grass is a good cattle food and can be converted to silage. It is also an excellent

source o f manure. It is also used fo rmanufacturing o f cardboard papers (Ansari ej a!..

1996).

The w'aste lemongrass is also used as a fuel for distillation after drying and as a cheap

packing material for glassware or other fragile objects (Farooqui et a i , 2001).

Lemongrass is effective in repelling mosquitoes and is used as an ingredient o f mosquito

repellant (Ansari el a i , 1995),

Chapter-4 __________ CYMBOPOGON CITRATUS

42

Discussion

The composition o f the oil, their retention index and percentage are summarized in Table

4T. The components are arranged in order o f GC elution on IJlbon HR-1 column. Eight-

peak index of volatile constituents along with their structures are given in table 4.2.

GLC and GC-MS analysis o f the oil revealed it to be a coniplcx mixture o f .several

components mainly rnonoterpenes and sesquiterpenes. A total o f 25 components

amounting to 97.8% and of total volatiles were identified. The oil was characterized by a

high percentage of monoterpene fraction, amounting to about 91%, dominated by ten

oxygenated monoterpenes (86.7%). Neral (41.7%) was the main constituent followed by

nerol (23.6%), 1,8-cineole (9%) and geraniol (6.9%). Five monoterpene hydrocarbon

amounting to 4,4%) consisted o f 3,7-dimethyl-l,6-octadiene, myrcene, p-cym ene, 1-

limonene and £’-(P)-ocimene. It is noteworthy to state that the higher oxygenated

monoterpene content in the oil especially the aldehydes (Table 4.1) are responsible for

lemon-like odour (I’orres and Ragadio, 1996).

The Sesquiterpene fraction is represented by three hydrocarbons (2.8%)) consisted o f

mainly /ra/vi’-P-caryophyllene (2.3%). Oxygenated Sesquiterpenes were not found in the

present studyt. Only one component was partially identified while 2-methyI-3-penten-ol

(0,4%) represented the nonterpenyl fraction of the oil. Earlier m ethyl-heptanones have

been reported by Ekundayo (1985) in a concentration ranging from 0.2-0.3%.

The composition of the oil in the present srudy is generally similar to that reported in

earlier reports, except that several terpenes were identified in the lemongrass oil for the

first time (Rulsi and Nurdjannah, 1993; Virmani el ah, 1979; Lawrence, 1984).

Chapter-4 CYM BOPOGON CTTRA TUS

43

4.1: Clicmicai composition of Cymbopogon cUratus oil

Peak No. Compotieiits R.I1 Formic acid 406 1.82 a-Thujene 922 0.63 a-Pinene 925 0.74 3,7-Dim elyl-l,6“OCtadienc 946 1.25 Myrcene 977 0,86 /?"Cymenc 1005 0.47 1,8-Cineole 1016 9.08 l"Limonene 1022 0.59 £'-(P)-Ocimene 1024 0.210 Linalool 1085 1.811 Citronellal 1136 0.412 Verbenone 1171 0.213 2-Methyl-3-penten-ol - 0.414 ;2eo-Diliydrocarveol 1177 0.815 Dihydrocarveol 1180 1.916 Bornyl acetate 1205 0.417 Nerol 1218 23.618 Neral 1220 41.719 C i2H20O2‘ - 0.320 Geraniol 1237 6.921 /m«5-P-Caryophyllene 1403 2.322 a-Humulene 1435 0.223 P-Selinene 1439 0.324 1,2-benzene dicarboxylicacid - 0.225 Palmitic acid - 1.2

Total (25) 97.8* Partially!identified

Monoterpene Hydrocarbon (7)

Oxygenated Monoterpenes (10)

Sesquiterpene Hydrocarbons (3)

Others (5)

Total (25)

4.4%

86.7%

2 .8%

3.9%

97.8%

Table 4.2: Eight mass peak index o f Cymbopogon citratus oil

N am e of S truc tu reF ragm enta tion

Formic acidCH2O246

H C O O H 45, 46(37), 43(20), 42(8), 44(6), 40(5), 38(5), 39(3)

a-T hujeneC 10H 16

U

93,91(45), 92(37), 77(35), 42(33), 79(30), 53(17), 80(11)

a-PiiieneC ,oH,6136

93,41(59), 121(51),79(46), 67(40), 91(36), 77(34), 107(24)

3 ,7-Dimethyl-1,6-octadineC , oH,6136

43,41(58), 55(24), 69(18), 58(13), 108(13), 67(19), 55(17)

MyrceiieC , oH,6136

41,69(35), 93(31), 67(19), 55(17), 43(14), 53(13), 79(12)

/7-CymeneC 10H 16136 6 119,91(34),

134(24), 41(17), 117(15), 65(13), 76(12), 120(11)

1,8-CineoleC|()HikO154

43,6 8(84),6 7(70), 41(60). 93(54). 79(36), 81(33). 53(34)

1-Lim oneneCioHifi136

93, 41(92). 79(85). 77(72), 91(61). 80(48), 53(39). 51(33)

£-(P)-OcimeneC ,oH,6136

93, 91(71), 121(67), 79(52), 136(51), 77(49), 41(47), 53(30)

10 LinaloolC|oH|gO154

CitronellalCioHisO154

43,41(89), 69(31), 93(30), 91(10), 53(10), 77(9), 79(9)

041, 69(46), 55(32), 95(19), 43(19), 56(19), 67(17), 53(11)

CHO

12 VerbenoneC ioH mO150

41,69(49), 108(48), 67(38), 109(37), 93(29), 95(28), 53(25)

2-Methyl-3-penten~l-ol

I C I W

41,69(58), 70(10), 53(11), 111(9), 81(8), 67(11), 112(11)

14

15

mo-DihydrocarvcolCioHigO154

DihydrocarvcolC„,H,aO154

41, 67(54), ?3(40). 81(35), 94(33), 53(27), 109(26), 79(24),

41, 69(59), 55(25), 67(22), 43(22), 68(14), 56(13), 55(11)

16 Bornyl acetateCioHigO172

COCH 41, 43(87), 59(52), 55(39), 68(31), 57(30), 67(30), 42(27)

17 NerolCioHigO154

C f tO

41,69(45), 67(19), 53(13), 59(1 1), 55(9), 84(11), 94(11)

18 NeralC ,oH,60152

41, 69(58), 84(14), 53(11), 94(8), 83(7), 67(8), 55(6)

CHO

19 C 12H20O2196

43, 41(54), 95(39), 58(31), 93(22), 69(17), 59(11), 67(11)

20 GeraniolCioHigO154 0

69,41(87), 43(83), 68(38), 67(18), 80(17), 93(19), 12(10)

21

22

CaryophylleaeC 15H24204

a-HumuleneC 1 5 H20188

/

41,81(64), 79(57).91(4S), 93(47), 67(46), 68(46). 53(46)

93,41(48). 80(44), 79(28), 91(27). 53(26), 77(23). 121(23)

p-selineneC 15H24204

41,43(76), 79(57), 91(43), 43(39), 69(33), 67(28), 77(27)

24 B is-1,2"benzene dicarboxylic acid.

149, 57(34), 41(26). 150(11), 76(9), 56(8), 104(8), 65(6)

25 Palmitic acidC 16H32O2256

CH3(CH,)h c o o h 43,41(69), 60(66), 57(60), 73(56), 55(51), 77(24), 69(24)

rooo

oo

..■;.. ..... : l:...... ! I-

Response {mVj

5,70

o ..H

o

oo-id0

1

§:

S

os

I ^ I . -

o01

03o

6

oo

Q

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Referejices

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Chapter-4 CYM BO PO G O N CITRA TUS

44

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Chapter-4 CYMBOPOGON CITRATUS

4 5

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169,

Chapter-4 CYM BOPOGON CITRATUS

46