E u calyptu s citriodora - INFLIBNETshodhganga.inflibnet.ac.in/bitstream/10603/42381/11/11_chapter 6.pdf · EUCALYPTUS CITRIODORA HOOK. (MYRTACEAE) Introduction Eucalyptus is a large

E u c a l y p t u s citriodora

EUCALYPTUS CITRIODORA H O O K .

(MYRTACEAE)

In tro d u c tio n

Eucalyptus is a large genus belonging to the fem ily M yrtaceae. It com prises m ore

than 600 species and subspecies o f evergreen trees and shrubs, m ainly native to

A ustralia, Tasm ania, N ew Guinea and neighboring islands. (Bhalla, 1997).

The nam e Eucalyptus was coined by L. Fleritier, a French B otanist in tlie year 1789.

Eucalyptus is form ed by ‘eu ’ means ‘w ell’ and “kalyptus” m eaning “I cover” ; thus

referring to the lid o f operculum w hich seals the fSower till it bloom s. Eucalyptus was

first introduced to India in the Naiidi hills o f K arnataka by Tippu Sultan betw een 1782

to 1790. Later in 1843 its plantation was extended to the N ilgiri hills in southern

India. N early 170 species have been tried in India out o f w hich only five species, viz.

E. tereticornis, E. ccmaldensis, E. grandis, E. citriodom , and E. g lobulus have

received w ide acceptance,

E, c itr iodom is am ong the econom ically im portant species o f eucalyptus available

w orldw ide. Its m ain utility is in the perfum e industry due to its h ighest citronellal

content (>70 % ). The wood o f the plant is also an im portant tim ber and firewood.

Synonym s

E. m aculata Hook.

Lem on-scented gum or Lem on-scented Eucalyptus.

V e rn a c u la r N am es

B engali Eucalyptus.

H indi Eucalyptus.

K annada N ilgiri mara.

Sanskrit Sugandhapatra, Tailaparna, and Haritaparna,

Tam il K arupuram aram .

Chapter-6 E U C A LY P TU S CI TIUODORA

D escrip tion

It is a tall gracefiil tree with slender tapering trunk. It attains a height up to 60 ni \viih

u straight, clean bole and sm ooth bark peeling olT in long thin strips or sheets. The

leaves are leathery in texture, hang obliquely or vertically and are studded w ith g lands

containing a fragrant volatile oil. The young leaves are broad, opposite , sessile,

cordate-ovate, glacous-grey; the adult leaves (after 4 or 5 years) are sw ord-shapcd , 1 5

- 30 cm long, bluish-green in colour, alternate, vertical. The flowers in bud arc

covered with a cup-like m em brane, which is thrown olT as a lid when the Hovver

expands. The fruit is surrounded by a w oody, cup shaped receptacle and contains

num erous m inute seeds.

D is tr ib u tio n a n d H a b i ta t

Eucalyptus is a versatile genus. Its rapid growth and adaptability have led to its

widespread introduction in many countries. E. citriodora is native to A ustralia and

Tasm ania and introduced to India as firewood species. It has been planted in the

plains o f northern India and in the subm ountain tract. It has been successfu lly grow n

in M alabar, N ilg iris and Coorg. A sm all plantation o f E.citriodora is found at

Lucknow. It is one o f the m ost popular garden species in the plains. It is also

cultivated in A ssam , M adhya Pradesh, Bihar, Kerala, M aharashtra and other areas o f

U.P. It thrives best in the areas with considerable soil m oisture but grow's also on

fairly dry ground. It is sensitive to severe frost and excessive drought.

In general, Eucalyptus trees grow on soil o f low nutrient status, but they have the

capacity to respond with growth rates to m ore fertile conditions and especially to

higher levels o f nitrogen (N) and phosphorus (P). E. citriodora p refer well drained,

deep and fertile soil with an annual rainfall o f about 1500 m m .

Chemical Composition

The essentia! oil o f Eucalyptus is obtained by hydrodistillation o f the fresh leaves. It

is colourless or pale-yellow liquid. It has an arom atic and cam phoraceous odour: a

pungent, cam phoraceous taste followed by a sensation o f cold. T he yield o f oil varies

from species to species, place to place and w ith the season. Eucalyptus oil can be

classified under three m ain categories depending on the principal constituents present,

viz-

Chapier-6 EU C ALYPTU S C ITRIO D O RA

Chapter-6 E U C A LYP TU S C ITRIO D O RA

1) M edicinal oils o r Cineol containing oils.

2) Perfum ery oils or Citronellal containing oils.

3 ) industrial oils or Phellandrene containing oils.

The leaves o f E .cilriodora yield an essential oil (0.5-2.0) containing citronellal (65-80

% ), citronellol (15-20 % ) and esters (W ealth o f India, 1952). O ils poor in citronellal

are reported to contain guaicol. The Kino obtained from E. cilriodora contains 4H.2 %

tannin.

The chem ical com position o f the essential oils obtained from the leaves o f 12 species

o f eucalyptus including E. citiodora growing in Eithiopia were exam ined by capillary

GC and CjC-MS. The oil o f £ Cilriodora was found to l->e rich in citronellal (73.3 %),

and citronellol (16.2 %). (D agne et a l.,2000).

O ils obtained by solid phase m icro-extraction process from three E ucalyptus species

were analyzed in Australia. Five E. cilriodora leaves from the sam e tree over different

m onths gave very sim ilar analysis o f 72.9 - 80.5 % citronellal, 3.5 - 5 .4 %

citronellol, 1.0 - 3.8 % citronellyl acetate, 9.2 - 11.8 % caryophyllene and 1.4 - 1.7 %

bicyclogerm aerene. (Betts, 2000).

C itronellal and isopulegol was the m ost abundant constituents, (approxim ately 78 %

and 6 % respectively) out o f 18 constituents identified from E.cilriodora oil (Chalchat

el al.,1000). The com position o f essential oils o f m edicinal plants o f M adagaskar was

determ ined. A nalysis was perform ed coupling the data obtained by capillary GC and

'H and '^C N M R techniques. The oil o f £. cilriodora was found to contain a -p in en e

(1.4 % ), p-pinene (1.2 % ), lim onene (0.3 % ), 1,8-cineole (1,0 % ), y-terpinene (0.4 %),

p-eym ene (0.5 % ), citronellal (71.2 %), linalyl acetate (3.4 %), citronellyl acetate (6.6

% ), P“caryophyllene (1.4 %), estragole (1.4 % ), a-terp ineo l (0.4 %), and eugenol (0.3

% ) (M edici et a l , 1992).

Pharmacological Activities

The essential oil o f E. cilriodora was screened for its fungicidal activ ity against

Fusarium monidiforme, a post harvest fungal pathogen o f cereal crops. It w as found

very effective in inhibiting fungal grow th.(B aruah, 1996).

A clinical trial w as m ade to evaluate antifungal activity o f E .citriodora oil. T he oil

was foimd m ost effective against M icrosporum mamim, Trichophyton n m ita g ra p h v ta

and T. rubnm i. Pure oil killed all organism s in 20 sec, at their m inim um fungicidal

concentrations (M FCs). The oil in the form o f ointm ent was subjected to topical

application on patients attending in the out patient departm ent o f K.L.N.K4edical

College, A llahabad, India. At the end of the treatm ent, 55.5 % o f patient.s recovered

com pletely.

A ntim icrobial activity o f the essential oils o f 21 Eucalyptus species against E.coU.

S.aureus, BaciUus rnegatcrmm, Candida a lh icam , Saccharom yces cercvisicie,

Aspergillus niger and Zygorrhynchus sp. has been investigated. The m oulds and yeast

were in general m ore sensitive than bacteria to the inhibitory activity o f essential oils.

E. cilriodora oil was found to be more efficient (Hajji, et a i , 1993). C itriodora oil

from E. citriodora was tested for the first tim e as fum igants against C alloxohnichiis

m aciilatus and D ysdercus kom ig ii. It was found to be very effective w ith L D 50 value

o f 444/1000 ml and 160/1000 ml respectively (Pajni, et al., 1991).

A lcoholic extract o f E. citriodora leaves possesses significant anti-inflam m atory and

analgesic effects at the dose o f 100, 300, and 1000 m g/kg; injected i.p., in m ice

against carageenaii induced inflamm ation. Laboratory studies w ere carried out on the

toxicity o f plant oils against 3 stored product beetles. E. cilriodora oil was the m ost

toxic against Rhyzopertha dom inica and O ryzaepophilhis surinam ensis (T hakur a ,

al., 1995).

Uses

The volatile oil o f E. citriodira is em ployed in soap and perfum ery industries due to

its pleasant odour. It is also used as a starting m aterial for the p roduction o f

citronellol, hydroxycitronella, isopulegol and m enthol. As a source o f citronellal, this

oil can com pete w ith com m ercial citronella oil. In Kenya, the E. citriodora leaves or

their extracts are either sprayed or hanged on the ventilators to repel m osquitoes

(Ejobi et a l , 1997). C itriodora oil has lim ited m edicinal values; still it can be used as

analgesic, antineuralgic, antirheum atic, antiseptic, antispasm odic, antiviral, balsam ic,

deodorant, diuretic, expectorant, stim ulant and verm ifusal. Physical arom atherapy

uses include ath letes’ foot, cut and grazes, bronchitis, m uscular aches, cold and flu. It

is particularly useful for the respiratory system. (Patel et al., 1980).

Chapter-6 EU CAL YPTLJS C ITR IO D O R A

Discussion

'Fhe com ponents o f the oil, the percentage o f cach constituent and their retention

indices are sum m arized in Table 6.1. Their eight-peak index is given in table 6.2. The

constituents are arranged in order o f their elution on the Ulbon I IR-1 Silicone colum n.

A nalysis o f the oil by GC/M S resulted in the identification o f 22 com ponents ou t o f

30, com prising 99% o f the total volatiles. Q uantitatively the oil wa.s characterized h\'

a high am ount o f m onoterpenes (64.1?/o). Out o f 12 m onoterpenes idenliHed, there

were 9 m onoterpene hydrocarbons (44.3% ), 2 m onoterpene alcohols (3.8%i) and one

aldehyde (16.2% ). The predom inant m onoterpene being sahinene (23.4% ) followed

by citroneilal (16.2% ), a -thu jene (1 3 .1 % ),/;-cym ene (6.4‘%) and cx-terpineol (2.4%)).

Am ong 10 sesquiterpenes identified (30.5%>) there were 4 sesquiterpene hydrocarbons

(4.7% ) and 6 sesquiterpene alcohols (25.8%i). The predom inant sesquiterpene was

globulol (11.8% ) followed by epi-globulol (8.3%>), elem ol (5.4% ) and p-

caryopliyllene (3.7%>). The oil of leaves o f £ citriodora contained m ainly citroneilal

(71.2"80,5%)), citronellol (3.4“16.2%a), citronyl acetate (1-6.6% ), isopulegol (6-7.35% )

linalyl acetate (3.4%)) and caryophylline (9.2-11.85%)) (Ali, 2001; Betts 2000; et a i ,

2000; C halchat et a l , 1995; M edici, 1992). It is notew orthy that the flow er oil o f the

plant grow n in Delhi contained only citroneilal (16.2% ) and p-caryophyllene (3.7% )

o f the com m on com pounds in foliar oils. G lobulol, epi-globulol, ledol and elem ol are

reported for the first tim e in E. citriodora oil.

The mass spectra for the partially identified com ponents: ms m/z (rel. int.. Rf 965, 136

[M"](C,„H|rt), 93 (100), 92 (35.8), 91 (40.2), 79 (24.9), 77 (32.6), 63 (11.9), 43 (13.4),

42 (31.5); 136[M 'l(C ,oH,6), 81 (100), 80 (57.6), 71 (24.9), 69 (32.6), 57 (22.8), 55

(31.5), 43 (68.4), 42 (57.4); RI 1203, 136 [M ^](C ,oH ,6), 92 (100), 91 (98,2), 42 (72.8),

43 (68,3), 81 (59.7), 79 (56.5), 77 (31,5), 53 (34.7); RI 1210, 136 [M '"](CioHi6), 43

(100), 42 (32.6), 55 (11.9), 67 (10.8), 69 (10.8), 80 (23.9), 81 (59.7), 93 (15.2); RI

1280, 43 (100), 42 (27.1), 55 (17.3), 71 (18.4), 91 (14.1), 97 (11.9), 111 (16.3), 126

(14.1); RI 1445, 204 [M‘'](Ci5H24), 42 (100), 55 (51.1), 79 (50.3), 81 (53.2), 93 (63.0),

107 (5 L I ) , 133 (38,0), 189 (49.9); RI 1524, 222 [M’ KCisHif.O), 59 (100), 42 (58.6),

44 (65.2), 91 (33.6), 107 (31.5), 119 (39.1), 161 (57.8), 189 (20.6); RI 1560, 222

[M 'KCisHacO), 42 (100), 55 (51.1), 79 (49.9), 91 (65.2), 105 (54.3), 133 (56.5), 189

(70.6), 204 (28.2).

Chapler-6 _ _ _ _ _ E U C A LY P TU S Cm U O D ORA

T ab le 6,1 C hem ica l Com position of the volatile oil o f Eucalyptus ciirioclora

P e a k No. C on ipo iie iits R l

!. a~T hujene 922 13.12 . Sab inene 960 23.43. Sab inene isom er ‘‘ 965 0.1

4. P-Pineiie 970 0,15. P-M yrcene 975 0.36 . p -C y m en e 1005 6.47. (Z)- p -O cim ene 1014 0.18. a -T e ip in e n e i O l T 0.19. L inionetie 1018 t1 0 . C ltronellal 1136 16.21 1 . D i iiydropyrid ine derivati . 0.11 2 . 2 ,6-D iinethyi-2(3)"7-octadene O .li13. 4 -E thy l-3 ,4 -d im ethy l-2 -cyc lohexene-1 -one - 0.114. 4-T erp ineoi 1149 ^ ■ .415. T erp ineol 1160 2.4i 6 . C ,oH i4 “ 1203 t17. C ,oH ,6 “ 1 2 1 0 0.218. 4-M e th y l-1 (1 -m ethyl ethyl) bicyclo (3.3.0) hexane-3-ol 1250 t19. U nknow n 1280 t2 0 . a -C o p aen e 1369 0.012 1 . p”CaryophyIlene 1400 3.72 2 . a -H u m u len e 1431 0.323. A rom adendrene 1450 0.324. C 15H 24 ‘‘ 1455 0.325. lilem ol 1524 5.426. E lem ol derivative “ 1535 0.227. Epi-g lobulo l 1544 1 1 . 828. G lobuio l isom er “ 1560 t29. G lobulol 1580 8.330. Ledol 1581 0.1

Total (30) 93.5

t - trace < 0 ,01% , “Partially identified com ponents

M onoterpene H ydrocarbons (9) = 44.3%

O xygenated M onote ipenes (3) 2 0 .0%

Sesquiterpene H ydrocarbons (4) = 4.7%

O xygenated Sesquiterpenes (6) = 25. 8%

Total (30) 93.5

Table 6.2: Etglit Mass Peak Index of Volatile Oil of Eucalyptm dtriodora.

o. N a m e

o f C o m p o n e n t

a~Thujene

C ioH k,

136

Structural Formula

UFi;

Eight Peak Index

93, 91(57), 92 (38), 7 9 ( ! 5).

77(5!), 65(8), 52(9),

Sabinene

CioHir.

136

93, 92(27), 91(52), 77(41),

65(7), 51(6), 44(7), 42(15),

3. Sabinene isomer

CioHif)

136

A 'u

93, 92(35), 91(40), 79(24),

77(32), 63(11), 44(13),

42(31),

P-Pinene

Ci(|Hi6

136

CH, 93,121(49), 107(23),

91(36), 79(47), 77(30),

67(41), 42(64).

P“Myrcene

CioHif,

136

A 42, 54(9), 67(8), 69(43),

77(9), 79(8), 91(10),

93(44)

;?-Cymene

C,(,Hi6

136

A119,134(28), 120(9),

117(14), 91(26), 77(8),

65(9), 41 (II),

7. (Z y p-Ocim ene

C ioH|6

136

93, 121(79), 136(67),

91(68), 79(43), 77(52),

44(33), 42(58).

8, tx-Terpinene

Ci()H|6

136

93, 136(27), 121(21),

92(24), 91(56), 77 (42),

44(38), 42(33).

9. Lim onene

C,oH ,6

136

93 ,91(28), 79(27),

77(27), 69(43), 67(14),

53(15), 42(85).

10. Citronellal

CioHisO

154

42 ,44(98), 55(59),

69(35), 71(88), 80(24),

93(43), 82(13)

Dihydropyridine

derivative

C ,oH.6

136

r81,80(57), 71(24),

69(32), 57(22), 55(31),

44(68), 42(57)

12. 2,-6"D im ethyl-2(3), 7-

octadiene isom er

CioHig

138

44 ,42(34), 55(21),

69(20), 71(24), 81(21),

93(20), 121 (14)

13. 4-Ethy 1-3,4-dimetliy l-

2 -cyclohaxene-l -one

CcHifiO

C H .

H3C

C2H5

95, 1 1 0 (22 ), 81(11),

67(17), 55(15), 53(10),

44(22), 42(38),

14. 4-Terpineol

CioHi?

136

71 ,11(34), 93(36),

69(26), 67(20), 55(29),

44(71), 42(42).

15. Terpineol

C)oH j7

136

59, 136(22), 121(27),

81(28), 67(17), 44(48),

93(41), 42(22).

16, CioHi4

134

92, 91(98), 81(59),

79(56), 77(31), 53(34),

44(68), 42(72).

17. C ,oH,6

136

44, 42(32), 55(11),

67(10), 69(10), 80(23)

81(59), 93(15).

18. 4-Metliy 1-1 (1 -m ethyl

ethyl) bicyclo (3.3.0)

hexane 3 ol

44 ,42(36),

55(16),67(14), 93(24),

95(60), 121(19), 136(16).

19. U nknow n 44 ,42(27), 55(17),

71(18.47), 91(14.13), 97

(11), 111(16), 126(14).

20. a-C opaene

C,5H2,

204

105,119(77), 161 (66),

93(47), 91 (56), 81 (38),

44(39), 42 (80).

21. (3-Caryophyllene

C.5H24

204l !

42, 55(32), 69(66),

79(45), 91(45), 93(57),

105(29), 133(38).

22, a-Humulene

C,5H24

204 1

n93,91(21), 80(35),

79(22), 67(19), 53(19),

42(52), 121(20),

23. Aromadendrene

C 15H24

204

42, 55(48), 67(53),

79(61), 91(55), 93(60),

105(57), 161(35),

24. Cl 5 H 24 42, 55(51), 79 (50),

81(53), 93(63), 107(51),

133(38), 189(49),

25. Eleniol

C 15H26O

204

59, 42(58), 44(64),

91(45), 105 (43), 161

(89), 119 (99), 204 (70).

26. Elerno! derivative 59, 42(58), 44(65),

91(33), 107(31), 1 19(39),

161 (57), 189(20).

27. Epi-Globulol

C 15H26O

222

42. 55(51), 79(49),

91(65), 105 (54),

133(56), 189(70), 98(28).

28. Globulal isomer

Ci5l-l260

222 H3C

2

CH3

CH3

. CH3

42, 55(51), 79(49),

91(65), 105 (54),

133(56), 89(70),204(28),

29. Globuiol

C 15H26O

222

59, 42(23), 44(23),

67(14), 81(15), 93(14),

109(15), 149 (27).

30. Ledol V - O H 59, 42(28), 44(29),

C,5H260 f93(18), 149(32), 161(24),

189(22), 204(21),222

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References

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Chapter-6 _ _ _ EUCALYPTUS CITIUODORA

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