l. Essent.Oil Res.,18, 613-617 (Novernber/Decernber 2006)
ChemicalCompositionof the EssentialOilsof Four
PlumeriaSpeciesGrownon PeninsularMalaysia
NorsitaToharand KhalijahAwang*
Departm'entof Chemistry, Faanhy of Science,(Jniuersityif Malaya, 50603l(uala Lumpur,
Malagsia
MustafaA. Mohd.
Departm'entof Pharmncology,Faculty of Medicine, (Jniuersityof Malaya, 50605Kt^tala
Lumpur, Malaysia
lbrahimJantan
Department of Pharmncy,Faculty of Allted Health Sciences,(JniuersitiKebangsaanMalaysia,
Jalan Mucla AbctutAziz,
50300l(uala Lumpur, Malaysia
Abstract
Tlre fower oils of four Plurnerta L. species;P. obtusn L., P. acu,minataAit. (yellow
florver),p. ru,bra L. (pink
florT'er)and P ntbra (orangeflower) hydrodlstilledfrorn yrnqfr_
qrlyn on peninsularMalaysia,were analyzedby gas
chromatographyon two columnsof different polarity and cizuS. The oil if p. obturnwas
iound to be rich in benzyl
salicylate(a5.a%a)
and benzf benzoate(tl .ZW, bui alsominute concentrationsof alkanoicacids.Oil obtained
from
P. acuminata wasrich in palmitic acid (S6.2Va),
linoleic ac
1'he pink flowered P.rubra oil was similar to p. acuminata
benzoateand rich in alkanoicacidsbut linoleic acidwas ab
P. ntbra oil containedboth the non-telpene esters(benz1
and alkanoicacidsin significantamounts.The orangeflorve
(14.47o)and geraniol( .IEI) amongthe speciesstudied.
KeyWord Index
Plum'ertaobtusa,Plumeriaacuminata,Plumeriatubra, Apocymaceae,
essentialoil composition,ben4zlsalicylate,
ben'4i benzoate,hexadecanoicacid, tetradecanoicacid, dodecanoicacid, linoleic acid, (E)-nerolidol,
lntroduction
Phmwria L. (Farnily: Apoclmaceae)is indigenous to tropical America and is found frorn southern Mexico to northern
South Arnerica (1,2). However, due to its easeof propagation
through cuttings, many species and hybrids of phuneio ^r.
now widely cultivated and distributed in the warrner regions
of the world (2,3). Phnneria,the rnost celebrated of all tropical
forvers, are cornrnonly known asfiangipani (1,2). In Malaysia,
it is most farnously called 'kernboja,' but several other narnes
'pokok
such as
kubur' and 'bunga kubur' have been used to
refer to different species and hybrid s of phrm.eria (1,4). The
trees were introduced to Malaysia and at least three rnain
species are cornrllonly found: Plumeria obtusa, p. ntbra and
P. acuminafa (designated as P aattifulia poir. by Burhll and
revised asP. nrbra forrna acu,tifolia(Poir.) Woodson in Hortus
Third) (r,4,5).
All species are small trees with very thick, fleshy. stout
branches and produce a rnilkyjuice when the leavesor branches
are cut. The leaves are spirally arranged near the ends of the
.Address
swollen branches and fruits are as a pair of cylindrical, hornshaped with n-ranyflat seeds shortly winged at one end. In
general, fiangipani leavesare green and the fowers are large,
waxy,very fragrant, in terminal or lateral stalkedcluster (4.6i).
Phmteria obtu,sahas white fowers with small brilriant yelow
center,up to 9 cm in diarneter;the leavesare dark green, glossy,
obovate and obtuse at both ends. The tree
gio* to-about
* tall and partly deciduous at different""r
tirnes
of the year
9_9
(6). While, P. aatmi,nata is an evergreen or partly deciduous
tree up to 6- rn high; leaves are light green in color, elliptic
in shape with aculri'ate tips and the color of the flower ca'
vary frorn white to yellow (4,5). phmeria ntbra in contrast,
has fowers in various shadesof red, pink. orange anclyellow;
the leaves also have many different iirer, shapes and colors
(4,8). This speciesis a deciduous tree which can exceed l0 rn
tall in the tropics but in the subtropics, it is unlikely to reach
rnore than 4 rn high (8).
Plurnerias are believed to be brought to the Far East by
the Spanish not just as ornamental trees but more of their
rnedicinal properties (t). The indigenous rledical traditions
for correspondence
Received: February 2005
104 1 -29051
06/0006-0613$ 14.00/0-€ 2006 Ailured pubtishing Corp.
Vol. 18, November/December 2006
Revised: June 2005
Accepted: July 2005
Journalof EssentialOil Research/613
Tohar et al.
in Java and Madoera make use of decoction of the reaves
as
lotion for cracks and eruptions on the soles of the feet while
decoction of the bark is given for gonorrhoea, dropsical and
venereal affections. In the philippine Islands and ffest Indies
the rnilkylatex and decoction ofihe bark are reputed to possess
purgative, emlnenagogic, febrifugic and diuretic properties.
In India the plant zrlsofinds applications in treatrnent of skin
diseases,fevers, dispersed dr"psies and the flowers are even
eaten with betel leavesto cure ague(l,g). Siddiqui et al. isolated
a- amyrin from the leaves of p. obtu sa, a pentacyilic triteqpenoid
which was an antiturnor agent (r0). I; rgs& Fujirnoto et al.
obtained frorn the leaves of p. aattifolta two neirzantiturnor
agents which were plurneric acid and rnethyl plurnerate (g).
Lupeol and ursolic acid were two antirnutagenis found in the
leaves of P. aatntinata (ll). Rubrinol **, *"rr"* antibacterial
triterpenoid found in p. nrbra by Nargis et al. (r2). coppen et
al. (1983) cornrnunicated the antifouring properties ofihe leaf
extract of P. nrbra and further claimeJthafthe iridoids, isoplurnericin, plurnericin, plurnieride cournarateand plurnieride
cournarate glucoside found in this speciesporr"rr6d algicidal
properties(13,14).
Despite all the cornprehensivescie'tific stucliesconclucted,
very scarceinforrnation is available on the constituents of the
essentialoils of the genus plunwria. only a few studies on the
oils of Hawaiian, Indian and Egyptian piumerias frorn different specieshave been carried out (2,15-19).As far as we can
ascertain, no work on the chemistry of the essential oils of
M^alaysianPlunwria has been docurnented. Therefore, as part
of a continuing study to identify new perfurnery rnaterials fiorn
plants throughout Peninsular Malaysia,we describethe volatile
components of the fowers of p. obhtsa, p. aatrninata &ellow
fower) and P nrbra (pink ancl orange flowers).
Experimental
Plant m,aterial: The fiesh fowers of four phnnerda species
were collected frorn Kuala Lurnpur. phnneria obhtsa and p
nrbra (pink flower) were collected in october rgg7, rn,hilep
acuminata (yellow fower) were collected {iom Novernber-Decernber 1997 and P. nrbra (orange fo'r,er) in March lggg.
Voucher specirnenswere depositJd at the Herbariurn of the
Departrnent of Chemistry University of Malaya.
oilisolation.'The oiis were obtainetl from the fresh flowers by hydrodistillation using a clevenger-type apparatus for g
h. The oily layers were further dried o""r'".rhviious sodirrrn
sulfate.The aqueouslayerfrorn the distillatewasextractedusing
n-hexane. The hexane layer was dehydrated with anhydrous
sodiurn sulfate and then the solvent was removed undei vacuo
at a low ternperature to recover the dissolved oil. The vields
were averaged over three experirnents and calculated tar"d
on the dry weight of the plant rnaterials.
GC and, GC4MS analgsis: The oils were analyzed by GC
(Shirna&u GC 17A chrornatograph equipped *ith a FID detector) and GC/MS (ShirnadzuGC t7A MS
ep 5000 _70 ey
inlet) using two different fused-silica capillary colurnn:
$T"a
DB-l (30 rn x 0.32 rnrn,0.25 prn film thickness)and barbowax
20M (30 m x 0.32 rnrn, 0.25 pm fihn thickness).
The operational pararnetersfor the GC analysiswere: Noas
carrier gas at 2.0 rnl,/rrin and the injector split fatio was 1,23.
614/Journal of EssentialOil Research
The injector and detector temperatureswere 2s0"c and 250oc,
The oven ternperature was prograrnrned initially at
llspegtively.
60"c for 3 min, rising at 3oc/rnin to zsd"cl5 rnin) for
".r"lysi,
using DB-r column. As for exarnination using carbowax
20M
stalignarl phase colurnn, the oven *", progiurnrned initially
at75"c for 3 min, rising at 3oc/rnin to zsot (r0 min). peak
areas and retention tirnes were measured by electronic integration. The relative amounts of individual co,nponents were
based on the peak areas obtained, without the rto response
factor correction. The ternperature prograrn linear retention
indices of the compoundr *"r" arro dJt".nrined relative
to
n-alkanes.
The GC/MS analyses were carried out under sirnilar
conditions as described above with He as the carrier gas.The
identiffcati,n of the che'rical co'stit'ents was base<l,n
the
comparison of their massspectral data with those fro rn the wiley
rnassspectral database,the cornparisonof calculated retention
indices with the literature'ualres and the co-chromatography
of sorneconstituents with authentic cornponents on the DB-r
capillary colurnn (20).
Resultsand Discussion
Hydrodistillation of the fresh fowers of clifl'ere't species
of Plumeria L. yielded 0.rsvo (p. obarsa),0.03vo (p. ic*t*inat a-y ellow fl ower ), 0 .O6 Vo(p.nrb ra-pr' k fl owe r and 0.3g Zo
)
(P.rubra-orange flower) ol oils.
e'aliiative anclquantitative
analysesofthe oils in&cated that generany non-terpenoid esters
and,/oracids were the rnajor
of the oils.
"o*porr"rris
A total of 37 compounds werelde'tified
in the essentialoil
of P. obtusa by GC and GC/MS. The floral oil was dominated
by esterswith ben4d salicylateand benzyl benzoate being the
maJorcornponents,amounting to 4S.4Voandl7 .2%o,respectively.
Benzylsalicy'ate has a rnild sweet odorwhere", b".rrvl benzo_
ate is ahnost odorless (2r,22). Four other ester
"o,trpo,rrrds
contributedtoS.Svo of the overall proportion of the
oii. Neryl
phenylacetate (2.67o)was the onlyierpenoid detected arnong
the ester gro^up There were lr alcoholic compounds with the
total )neld of l4.0vo. This alcoholic group was',nade up of six
monoterpenoids(5.\vo) and five sesquiteqpenoids( r0. +.2 Li').
alool, present at r.gvo,has a light and refieshing, foral-*,oody
odor.with afaintly citrusy note (2). while g"."niol (2.svo) and
nerol (o.7Eo)produced flowery roselike odJr (but nerol is more
refreshing and more lernonlike) (2r,22). (E)-Neroli dol (Z.svo)
and (E'E)-farnesol (4.8To),werethe rnajor representativesof
sesquiterpenoidsin the floral oil of p.obtusa.Geranial,neral and
stearaldehyde arnounted to 0 .svo,0 .4vo and,o . r vo,r e spectively,
and were the only aldehyde cornponents occurred in tlie oil.
This flower hasa fresh f oral, flowery roselike and strong le'ron
scent. Obviously, ben4rl salicylate, (t, E )-farnesol, ( E -nZrohdol
)
and linalool were the most significantvolatile compoundswhich
characterized the fresh sweet foral scent. Geraniol and nerol
were responsiblefor the roselike scent while the strong lernon
scent was characterized by neral and geranial (2). rhe oil also
cornprised l0 hydrocarbons and six rniicellaneous cornpounds
but present in minute quantities and did not contributl to the
scent of the P.obtusa fo'r'ers. Kamariah et erl.reported the oil
content of P. obtu,safrorn Brunei Darussalarnand found that
the rnajor cornponents were benzyl salicylate, benzylbenzo_
Vol. 18, November/December 2006
Plumeria species
ate, farnesol and (E)-nerolidol which are in agreernent with
our findings (3).
The analysisof P.aarminata (yellowfo*,er) has resulted in
.
the identificationof 2i volatile cor'po'nds. The r'ai'courponents were alkanoic acids, accumulatedtoTs.gvo of the total
also supported by the ester cornpounds in which O.svo was
monoterpenes and 6.7va were non-telpenes (even though the
individual concentration was relatively low which is les! than
IVo concentration).
The analysis of P. nrbra (orange flower) has resuitecl in
the identification gf aL
The oir cornprised l0
"ntnpnnrds.
esters(43.3Vo),I I hydrocarbons
(8.l%o),l0 alcohols(2g.gTo),
four carboxylic acids (8.svo), two ethers (r.Tvo) and three
aldehydes (2.5vo). Benzyl salicylate, at 20.gva,was the rnost
abundant cornpound in this oil. other ester cornpounds that
Vol. 18, November/December 2006
(3.3Eo)and cr-fenchylalcohol (z.rEo). (E)-Nerolidol
was the
rnostabundant sesquiterpenefollowed by ( E, E
)-farnesol,both
accumulated to L4.4vo and4.4vo, respectively. Nerolidol has
a rnild foral, rvoody and longJasting tclor *hile {'arnesol
has
a pleasant floral odor (2r,22j. All of the zrlkanoicacids were
prf.senl aj an appreciable concentration (except for lauric
acid which was less than Lvo); rnyristic acid at z.bqo,pahnitic
acid at 4.4va and linoreic acid ai r.Lvo. Aldehyde grirrp **,
represented by benzaldehyde, geranial and neral, imounted
to I .4Vo,l.j%o and O.\Eo,^respectively.
This cultivars produced
sweet foral and faintly fresh aroma which obviousfwere
the
characteristicsofthe majorconstituents such asben4rl salicylate
and telpenoid alcohols.
As shown in Table I, cultivars that were absent from benzyl
salicylateand ben4rl benzoate, have very high concentrations
in alkanoic acids (lauric acid, rnyristic
acid and
linoleic acid). In fact those acidi were "cid,"pal,r,itic
the *"1o. constituents
of the oils, except for linoleic acid which *a,
in the
"bse.rt
pink fowered P' nrbra oil. p acurninata of the yeilow
fower
cultivar did not consist of ben4rl salicylate orben4rlbenzoate
just like the-pink flowered p. rubra tut possessei
very high
yield in linoleic acid (l6.8vo). The fo.ner also lacked ,r"il
phenylacetate and (E)-nerolidol and contained only rninute
amount of linalool (0.3lEo).Asfor p. nrbraof orangefower,
it
was rnade up rnainly of non-telpene esters (ben4,isalicylate,
benzyl benzoate and 2-phenyleihyl benzoate) and contained
sig,ificant ar'ounts of alkanoic acids.Ar'ong the speciesstuclt*'_a!" orange flower c'ltiva's has the high;st ccri-rcentrati,n
of (E)-nerolidol (l4.4%o)and geraniol U.lqd.
Althougli the fragrancegven off by the fresh f owerso{'each
Plunteria-speciesstudied in this
indicates the presence
"orr.i"
of oils which can be exploited for
comrnercial isolaiion, the
percentage yields of the oils were low. cornrnercial isolation
of either the oils or favorable compound(s) of the oils may not
be viable due to this factor. Nerre-rtheless,
if prope, steps a.e
taken to develop these trees into agriculturil
(as they
can be
propagated), the forJ oils might".op,
bi potential
"Tily
sourcesof raw rnaterialsto be incolporated into the pe.f,rrr,"
industry especially the oils of p. obilrsa and,p. nrbri (orange
fower) which possessedhigh concentrations of esters.
References
1. I'H. Burkiil,A Dictionaryof rhe Economicproductsof rhe Maray
Peninsular.
Vor.il(r-Z),pp.177t1778,crownAgentsforthecoronies,
London (1935).
2.
A Omata, K.Yomogida,S. Nakamu ra, S. Hashimoto,T.Arai and
K. Furukawa,
volatile components of plumeria Flowers. part l. plumeria rubra
forma
acutifolia (Poir) woodson cv.' co m m on yeilow'. Frav.Fragr.J,, 6, 277 -27g
(1se1).
3. A's. Kamariah,LindaB.L.Lim, K.H.c.Baser,T. ozek and B. Demirci,
compositionof the Essentiaroir of prumeriaobtusa L. Frav.Fragr.J., 14,
237-240(1999).
4. E.J.H.Corner,WaysideTreesOf Malaya.Vol.l, 147_14g(1952).
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158,University
of Hawaii,48(1983).
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Press,KualaLumpur,Malaysia
(199g).
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Garden.83(1992).
o S.Begum,
A. Naeed,B.S.Siddiqui
andS.Siddiqu
i, ChemicalConstituents
of theGenusPlumeria.
J. Chem.Soc.pakistan,16,280_299(1994).
Journal of EssentialOil Research/615
Tohar et al.
Tabfel. Percentagecomposition of the flora oits of ptumeriaspecies
Compound
0-thujene
sabinene
benzaldehyde
isobutylvalerate
cr.s-linalool
oxide (furanoid)
frans-linalooloxide (furanoid)
linalool
a-fenchylalcohol
terpinene-4-ol
o-terpineol
nerol
neral
geraniol
geranial
neryl formate
nerylacetate
B-geranicacid
(E)-methylcinnamate
a,-copaene
B-patchoulene
p-bourbonene
B-caryophyllene
B-santalene
y-himachalene
amyl salicylate
elemol
(E)-nerolidol
caryophylleneoxide
dodecanoicacid (lauricacid)
2-phenylethythexanoate
heptyloctanoate
(Z,E){arnesol
(Z,Z\larnesol
(E,E)-farnesol
benzyl benzoate
tetradecanoicacid (myristicacid)
2-phenylethylbenzoate
benzyl salicylate
1-octadecene
nonadecane
2,6,10, 14-tetramethylheptadecane
neryl phenylacetate
hexadecanoicacid (palmiticacid)
ercosane
hexadecanoate(ethytpatmitate)
cinnamylcinnamate
heneicosane
octadecanoate(methylstearate)
linoleicacid
docosane
octadecanal(stearaldehyde)
tricosane
docosene*
pentacosane
RI
926
976
1005
1040
1057
1068
1085
1110
11 6 5
1170
1210
1227
1237
1244
1267
1343
1359
1365
1369
1379
1405
1429
1449
1476
1507
1540
1550
1570
1604
1616
1666
1681
1690
1710
1730
1804
1841
1857
1885
1900
1935
1953
1997
2000
2030
2055
2100
2 13 0
2181
2200
2272
2300
2305
2500
Method of lD
t
t
0.1
t
a
1.9
0.3
t
0.3
0.7
0.4
2.3
0.5
t
t
0.3
t
t
0.1
t
t
0.1
0.1
0.1
0.2
4.8
0.3
t
1.4
0.3
t
1.0
t
0.1
0.2
1.4
0.1
0.6
0.4
3.3
2.1
0.3
0.2
0.3
0.1
4.1
1.0
0.1
1.4
0.4
0.2
t
0.2
0.1
0.1
0.1
t
0.2
0.5
0.2
2.5
0.4
0.1
1.5
10.4
30.8
0.3
0.3
0.3
1.5
1.4
4.8
17.2
0.5
10.3
17.4
45.4
2.0
1.6
2.0
8.2
2.6
1.2
36.2
9.8
0.7
2.2
0.3
0.5
3.7
0.2
0.1
1.4
0.3
0.5
0.6
1.4
1.2
4.4
16.8
5.1
0.8
8.1
14.4
3.1
0.1
0.3
0.4
4.4
8.6
2.9
3.9
20.9
0.8
2.8
4.1
4.4
2.8
3.1
0.5
0.9
1.6
1.1
0.4
2.8
o.7
0.3
2.0
0.9
0.2
2.7
5.6
MS,RI,CO
MS,Rl,Co
MS,RI,Co
MS,RI
MS,RI
MS,RI
MS,Rl,Co
MS,RI,CO
MS,RI,CO
MS,RI,CO
MS,RI,Co
MS,RI,Co
MS,RI,Co
MS,Rl,Co
MS,RI
MS,RI,CO
MS,RI
MS,RI
MS,RI,Co
MS,RI,Co
MS,RI,CO
MS,RI,CO
MS,RI,CO
MS,Rl,Co
MS,CO
MS,RI,CO
MS,RI,GO
MS,RI
MS,Co
MS,RI
MS,RI
MS,RI
MS,RI
MS,RI
MS,RI,CO
MS,Co
MS,Rl,Co
MS,CO
MS,Co
MS,RI,Co
MS,RI
MS,CO
MS,CO
MS,RI,CO
MS,RI
MS,RI,CO
MS,RI,Co
MS,RI
MS,CO
MS,Co
MS,Co
MS,CO
MS,Co
MS,Co
percentageswere obtained by peak-areanormalizationon a DB-1 capillarycolumn;the retentionindex
of compoundson the Carbowax20M was also determined;Rl =
retentionindices;MS = mdss fragmentation;Co = co-chromatographywith authenticsample; 1= Pobtusa;2= p
acuminara(yellowflower);j= p rubra(pintilower): a = p
rubra (orangeflower);'correct isomer not identified;t= trace (< O.O5%)
616/Journal of Essential Oil Research
Vol. 18, November/December 2006
Plumeria species
1 0 . S.Sicldiqui,
B,S.Siddiqui,
A.NaeedandS.Begum,Constituents
o/plumeria
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Phytochemistry,
22,17*1 82 ( 1983).
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Comrynents of Plumeria Flowers.pan 2. plumeria rubra L. cv.,lrma
Bryan'.Flav.Fragr.J., Z, gg-g5 (1992).
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Fragr.J., 9, 343-345 (1994).
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15,49-49 (1974),
20. R.P.Adams,ldentificationof EssentialOilsby GasChromatogruphy/Mass
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