FLAVOUR AND FRAGRANCE JOURNAL

Flavour Fragr. J. 2001; 16: 241–244

DOI: 10.1002/ffj.986

Essential oil constituents of Melia dubia, a wild relative

of Azadirachta indica growing in the Eastern Ghats of
Peninsular India
M. A. H. Nagalakshmi, D. Thangadurai, T. Anuradha and T. Pullaiah∗
Department of Botany, Sri Krishnadevaraya University, Anantapur 515 003, Andhra Pradesh, India
Received 26 September 2000
Revised 3 January 2001
Accepted 9 January 2001

ABSTRACT: The leaf essential oil of Melia dubia Cav. (Meliaceae) has been studied by GC–MS. The leaf
essential oil consists chiefly of monoterpenes (35.71%) and oxygenated monoterpenes (27.98%), accompanied by
a relatively much smaller amount of alkanes (11.17%), sesquiterpene hydrocarbons (9.26%) and phenylpropanoids
(3.90%). The monoterpene camphene occurs as a major constituent (21.68%) of this leaf essential oil. It is
accompanied by a noticeable amount of ˛- and ˇ-pinene (3.12% and 5.13%, respectively) and a much smaller
amount of sabinene (2.75%). The oxygenated monoterpenes are distinctly dominated by the presence of the
bicyclic ketone camphor (17.85%), while iso-borneol and borneol are detected in much smaller amounts (4.15%
and 1.12%, respectively). Copyright  2001 John Wiley & Sons, Ltd.
KEY WORDS: Melia dubia Cav.; Meliaceae; essential oils; GC–MS; camphene; camphor

Introduction antibacterial,28 anitprotozoal23 and antiviral29 properties,

Meliaceae, a versatile family of great importance in bio-
organic research, comprising 50 genera and 550 species,
is distributed in tropical and subtropical regions of the
world. In India, the family is represented by 17 genera
and 72 species, found scattered only in moist and tropical
forests of hilly areas in Eastern and Western Ghats, of
which approximately 18% are endemic to Peninsular
India.1
The family Meliaceae was intensively studied for
its nimbinene, 6-deacetyl nimbinene, Nimbandiol,
6-O-acetyl nimbandiol, nimbolide, 28-deoxonimbolide,
terpenoids, flavanone, 15-acetoxy-7-deacetoxydihydro-
azadirone, quercetin, meldenin, isomeldenin, limocinol,
limocinone, limocin A and B, limocinin cyclopentate-
trahydrobenzofurans, odorine, odorinol, dehydroodorin
and limonoids.2 – 24 Plants of the Meliaceae are charac-
terized by the synthesis of modified triterpenes known
as limonoids. Over 300 limonoids have been iso-
lated to date and they are more diverse and abun-
dant in this particular family than in any other family.
They attract considerable interest, particularly because
of their antileishmanial,25 antimalarial,26 antifungal,27
*Correspondence to: T. Pullaiah, Department of Botany, Sri Krish-
nadevaraya University, Anantapur 515 003, Andhra Pradesh, India.
E-mail: tpullaiah@usa.net
Contract/grant sponsor: University Grants Commission, Government
of India.
and are used as immunomodulators,27 cytotoxics30 and
insect antifeedants.31
Melia dubia Cav. (Meliaceae) is a majestic and
densely foliaceous deciduous tree. The wood is very soft
and useful for making plywood and musical instruments.
The pulp of the fruit is a favourite remedy for colic and
is said to relieve pain most effectively among the labour-
ing classes. It also acts as an anthelminthic. The pulp of
the fruit, a measure of sulphur and an equal quantity of
curds heated together in a copper pot is used to cure
scabies and sores.32 The stem bark extract mixed with
opium (Papaver somniferum) in the ratio of 4 : 1 (2–3
spoonsful twice a day for 9 days) is given for rheumatic
pains by the aboriginal tribals of Eastern Ghats, Konda
Reddis and Koyas.33
Although the chemical constituents have not yet been
thoroughly investigated, the essential oils and their com-
ponents are becoming increasingly popular as naturally
occurring antimicrobial agents. In this work, the chem-
ical composition of Melia dubia leaves and its main
components were determined.
Experimental
Plant Material
Leaves of Melia dubia were collected from the moist
deciduous forests in Rollapenta of Kurnool District,

Copyright  2001 John Wiley & Sons, Ltd.

242 M. A. H. NAGALAKSHMI ET AL.

Andhra Pradesh, India, in April 1999 and an identified Table 1. Composition of the leaf essential oil of Melia
voucher specimen (No. 21708) documenting this col- dubia Cav. (Meliaceae)
lection has been deposited in the Sri Krishnadevaraya Peak No. Compound RIa (%)
University herbarium.
1 ˛-Thujene 924 trb
2 ˛-Pinene 930 3.12
3 1,2,3-Trimethyl benzene 955 0.31
Oils Preparation 4 Camphene 957 21.68
5 Oct-1-en-3-ol 961 trb
6 Sabinene 967 2.75
The leaves (300 g), in small pieces, were subjected to 7 ˇ-Pinene 971 5.13
hydrodistillation for 8 h, adopting the Egyptian Pharma- 8 Myrcene 983 0.20
copoeia (1984) method. 9 3-Carene 1000 trb
10 ˇ-Phellandrene 1005 trb
11 Cis-ˇ-Ocimene 1017 0.66
12 Limonene 1020 trb
Determination of Physical Constants 13 MW 222 1023 2.76
14 trans-ˇ-Ocimene 1027 trb
15 -Terpinene 1035 1.86
Specific rotation, [˛]22
D , was performed on the methono- 16 Terpinolene 1064 trb
lic solution of the oil (1%) and measured in 1 dM 17 Linalool 1085 0.26
tubes at the Sodium D Line using a Perkin-Elmer 141 18 Undecane 1100 1.31
19 Camphor 1132 17.85
polarimeter. Specific gravity was determined using a 20 trans-2-Nonenal 1136 trb
micro-specific gravity bottle. 21 iso-Borneol 1154 4.15
22 Borneol 1166 1.12
23 ˛-Terpineol 1171 trb
24 Dodecane 1200 7.56
Gas Chromatographic Analyses (GC) 25 Decanal 1204 1.18
26 Thymol 1272 1.38
27 Bornyl acetate 1277 1.12
A Varian 3300 gas chromatograph equipped with FID 28 Tridecane 1300 trb
and a fused silica capillary column (28 m ð 0.25 mm 29 ˛-Terpenyl acetate 1334 0.92
i.d.) coated with bonded phase DB-1 of 0.25 m film 30 ˛-Copane 1376 trb
31 ˛-Cubebene 1382 0.76
thickness. Injection of hexane solution (1 ml, 2.8 mg/ml) 32 ˛-Bourbonene 1383 0.38
was applied and the chromatogram was produced by 33 Pacifigoria-1(6),10-diene 1418 2.13
holding the oven temperature at 50 ° C for 1 min, then 34 ˇ-Caryophyllene 1420 trb
programmed from 50–270 ° C at 40 min. Helium was 35 -Decalactone 1428 0.21
36 ˛-Bergamotene 1434 trb
used as a carrier gas at a linear flow rate of 30 ml/s, 37 ˛-Humulene 1447 2.06
measured at 150 ° C, with a split ratio of 1 : 30, and the 38 ˇ-Cubebene 1474 1.13
septum sweep was held constant at 10 ml/min. Quan- 39 Germacrene D 1480 2.80
40 Shyobunone 1491 trb
tification and retention time determinations were carried 41 Caryophyllene epoxide 1537 0.60
out with a Spectra Physics SP 4290 integrator. 42 MW 236 1539 1.12
43 Proisocalamendiol 1587 1.83
44 Myristicin 1606 3.90
45 Aristol-9-en-3-ol 1651 trb
Calculation of Kováts Retention Indices(IR ) 46 ˇ-Bisabolol 1668 4.50
47 Heptadecane 1700 2.30
Identified Components 99.04
The oil was spiked with a standard mixture of Grouped components
homologous n-alkane series (C8–C23) and analysed by Monoterpene hydrocarbons 35.71
GC under the above-mentioned conditions. Retention Oxygenated monoterpenes 27.98
Sesquiterpene hydrocarbons 9.26
indices were directly obtained by application of Kováts Oxygenated sesquiterpenes 7.14
procedure.34,35 Phenylpropanoids 3.90
Alkanes 11.17
Others 3.88
Oil yield 0.97
Gas Chromatographic–Mass Spectrometric
Analysis (GC–MS) a
Retention index, relative to –C8 C23 n-alkanes on the DB-1 column.
b
Trace < 0.20.%
tr, traces.
A Girdel series 32 gas chromatograph (Delsi, France)
coupled with Nermag R10-10C mass spectrometer was Components Identification
used and spectra was produced under the same con-
ditions mentioned above to obtain comparable results. The oil constituents were identified by matching their
Mass spectral analysis was run by EI technique at mass spectral and retention indices data with those
70 eV. reported in the literature.36 – 38

Copyright  2001 John Wiley & Sons, Ltd. Flavour Fragr. J. 2001; 16: 241–244

Table 2. Mass spectra of unidentified compounds of Melia dubia
Peak No. RI MW
13 1023 222 93(100), 43(66), 162(49), 91(49), 41(48), 105(32), 119(31)
42 1539 236 175(100), 41(45), 57(35), 41(29), 109(28), 77(20), 85(17), 55(11)
Results and Discussion
Leaves of Melia dubia gave, on hydrodistillation, pale
yellow oil (0.97% v/w) which was lighter than water and
had a pungent odour; [˛]22 °
D  20.02 (C D 1, CH3 OH);
specific gravity, 0.928 at 25 ° C. GC of the freshly dis-
tilled oil revealed the presence of as many as 47 compo-
nents, 32 of which were identified, accounting for about
95.16% of the oil composition (Table 1).
The leaf essential oil consists chiefly of monoter-
pene hydrocarbons (35.71%) and oxygenated monoter-
penes (27.98%), accompanied by relatively much smaller
amounts of alkanes (11.17%), sesquisterpene hydrocar-
bons (9.26%) and phenylpropanoids (3.90%).
The monoterpene hydrocarbons are present in a sur-
prisingly significant amount (35.71%), with camphene
as the major constituent (21.68%). It is accompanied by
a noticeable amount of ˛- and ˇ-Pinene (3.12% and
5.13%, respectively) and a much smaller amount of
sabinene (2.75%). The oxygenated monoterpenes are dis-
tinctly dominated by the presence of a bicyclic ketone,
camphor (17.85%), while iso-borneol and borneol are
detected in much lower amounts (4.15% and 1.12%,
respectively).
The oxygenated sesquiterpenes are only represented
by ˇ-bisabolol (4.50%), and ˛-humulene (2.96%) as
major constituents in the leaf essential oil. The presence
of low concentration of shyobunones (0.09%), proiso-
calamendiol (1.83%) and phenylpropanoid, myristicin
(3.90%) could be considered as characteristic chemotax-
onomic marker of the studied genus, Melia of the Meli-
aceae. The presence of alkanes in higher concentrations,
such as dodecane (7.56%) and heptadecane (2.30%),
are also noticeable. The unidentified components were
detected in lower concentrations (3.88%) (Table 2).
Camphene, the major constituent (21.68%) in Melia
dubia occurs widely in nature also, with wide applica-
tions in all kinds of technical preparation. It has been
stated that the other major constituent of this oil, cam-
phor, although produced in very large quantities from
camphor oil (camphor tree), is not widely distributed in
other volatile oils, but in Melia dubia it occurs as 17.5%
of the essential oil. It is used widely in countless medic-
inal preparations as a local anaesthetic and a remedy for
rheumatic conditions and muscular strains. Internally it
serves as a circulatory stimulant and as a calmative. ˛-
and ˇ-pinene, which occur in noticeable amounts are
also used as a disinfectant and insecticide.39 – 41 Further
research will be necessary to elucidate the structure of
unknown compounds of the essential oil.
Copyright  2001 John Wiley & Sons, Ltd.
ESSENTIAL OIL OF MELIA DUBIA 243
m/z (Rel. int., 70 eV)
Acknowledgements—We are grateful to the University Grants Com-
mission, Government of India, for financial assistance in the form of
a Senior Research Fellowship to M.A.H. Nagalakshmi.
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