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Annonaceae Essential Oils: A Review

a a a
Gilbert Fournier , Michel Leboeuf & André Cavé
a
Laboratoire de Pharmacognosie, URA 1843 CNRS (BioCIS),
Faculté de Pharmacie, 5 rue J.-B. Clément, F-92296,
Châtenay-Malabry Cedex, France
Published online: 09 Dec 2011.

To cite this article: Gilbert Fournier , Michel Leboeuf & André Cavé (1999) Annonaceae
Essential Oils: A Review, Journal of Essential Oil Research, 11:2, 131-142, DOI:
10.1080/10412905.1999.9701092

To link to this article: http://dx.doi.org/10.1080/10412905.1999.9701092

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 J . Essent. Oil Res., 11, 131-142 (Mar/Apr 1999)

Annonaceae Essential Oils: A Review

Gilbert F o d e r , ' Michel Leboeuf and An& Cav6

Laboratoire de Phanacognosie, VRA 1843 CNRS (BioCIS>,Facultt? de Phanacie
5 rueJ.-B. Clhent, F-92296 ChBtenay-Malabry Cedex, France

Abstract
Many species among the Tropical Annonaceae family are odorous; this property
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is due to the presence of essential oils which are mainly composed of mono- and
sesquiterpene compounds. The aim of this work is to give an overview of all
published studies on the chemical composition of essential oils of various plant
parts taken from numerous species belonging to different genera of Annonaceae.
In the Annonaceae, the main compounds are usually monoterpene hydrocarbons
in fruit and seed oils, sesquiterpene hydrocarbons in leaf oils, and oxygenated
sesquiterpenes in bark and root oils. Most constituents identified are c o m o n , such
as a-pinene, limonene, P-pinene, P-caryophyllene, p-cymene and caryophyllene
oxide. Other components seem to be more specific to a particular Annonaceae genus.
Key Word Index
Annonaceae, Xylopia, Annona, essential oil composition, monoterpenes,
sesquiterpenes.

Introduction
Annonaceae is a large family comprising ca 130 genera and more than 2,000 species. Numerous
chemical studies have been made about Annonaceae and a review was published in 1982 (1). This
review covered all the constituents of primary metabolism such as carbohydrates, lipids, amino acids
and proteins, and especially secondary metabolites such as alkaloids, and non-alkaloidal compounds
(polyphenols, terpenes, aromatic compounds, etc.). Numerous other substances belonging to these
same phytochemical groups have been isolated since the publication of this review; in fact a new class
of constituents named acetogenins has been discovered since 1982 in the Annonaceae (2-4).
Numerous species among the Annonaceae are odorous; these fragrances are the consequence of the
presence of essential oils, mainly containing terpene compounds. Few volatile substances have been
studied so far in comparison with alkaloids and acetogenins.
Several reviews have been dedicated to these volatile substances: first, a general review published
in 1989 (5), and three further studies on Cananga odoratu flower oil (6-81, as a consequence of the
economic importance of this species which supplies Ylang-Ylang oil to the perfume industry. Most
studies have been made on oils obtained by steam distillation (in 3/4 of cases), the other works concern
volatile fractions extracted by organic solvents.
To the best of our knowledge, more than 150 studies (more than 30 of which were on the flowers
of Cananga odorafu)have been dedicated to oils isolated from various parts taken from 50 Annonaceae
species belonging to 20 distinct genera (Table I>. The species belonging to Xylopia and Annona genera
are the most numerous.

'Address for correspondence

Received: November 1997
Recefved: Manb 1998
1 0 4 1 - 2 9 0 5 / 9 9 / 0 0 0 2 - 0 1 4 9 $ 0 4 . 0 0 / ~ ~Allured
1~ Publishing C o p . Accepted: May 1998
 132 FOURNWET AL.

Table 1. The essential oils of Annonaceae species studied

Genus Number of species Genus Number of species

Xylopia 12 Cleistopbolis 1
Annona 8 Dennettia 1
Artabotrys 6 Enantia 1
Monodora 4 Fitzalania 1
Guatteria 3 Haplosticbantbus 1
Monantbolaxis 2 Hexalobus 1
Uvaria 2 Miliusa 1
A naxagorea Pacbypodantbium 1
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1
Asimina 1 Polyaltbia 1
Cananga 1 Unonopsis 1

Since Ekundayo’s review published in 1989 (51, numerous studies have been dedicated to
Annonaceae oils; the object of this work is to update the knowledge by making here a different and
supplementary presentation. This presentation is limited to oils sensu stricto(that is, according to I.S.O.,
obtained by steam distillation) and on the other hand to the presence of constituents in the oils in
significant proportion (22%).
Results and Discussion
All the results published concerning the constituents of Annonaceae oils are shown in Table 11. There
are seven columns, namely:
Annonaceae species and references;
studied part and essential oil content; note that this last result doesn’t always appear in all
publications;
number of identified compounds;
identified constituent percentage sum;
main constituents identified in the oils ( i . e .compounds in which the content is above 2%; these
constituents are classified in decreasing proportional order;
nonoxygenated terpene (CxHS us. oxygenated terpene proportions (CxHyO);
monoterpene (C,J us. sesquiterpene (C,,) proportions.
These two last columns concern only terpene constituents. In fact, most Annonaceae oils contain
mainly mono- and sesquiterpenes (Table 11). However, other constituents of a different biogenetic origin
have been identified in some Annonaceae oils extracted by steam distillation. When their content is
1 2%, they are given in Table 11. There are few phenylpropane derivatives and also aliphatic derivatives
which are specially present in large amounts in Annona muricata oils (9-11) and in Asimina friloba
fruit oil (12).
From the data presented in Table I1 it can be seen that fruits are the organs which are most studied
because many Annonaceae fruits are edible. On the Contrary, few studies have been performed on
flowers. Apart from Xylopia longiJolia flowers (78), only Cananga odorala flowers have been studied,
and most studies performed on the oils of this species are mentioned in three reviews (6-8). The oil
contents vary greatly according to the species and the organ: from 0.01% in Annona muricata leaves (19)
to 6.8% in Monodora myristica seeds (19).
The number of identified compounds in the oils can vary: from one or two (in old studies) to more
than one hundred for Cananga odorala oil. This, of course, is due to the economic importance of this
species (vide supra). In more recent studies, the percentage sum of identified compounds ranged
between 75% and 95%. This value is far smaller (or not mentioned) in most of the former works which
were not carried out by modern analytical methods such as GC.
 Table II. AnnoMc(M essential oils obtained by steam distillation

AnnonaMe
5-i- (nt)

Anaxagoma
dolichocarpa
fruit
0.5
I 37 I 93,9 I Scadinol. caryophylleneoxide, Scadinene. acopaene,
y-muumlene, spathulenol, pcymene. guaiene I 46.5
46.9 I 11.3
82.1
(13)
I yf
~~

Annona arnbotay 2.3

stem 12 45.6 pcaryophyllene, y-elemene. pelemene, y-muumlene
(14) 43.3
Annona aternoya germacrene D, (E)-p-ocimene, a-pinene. bpinene, 84.4 59.3
fNit
(15) 2o O0 bicyclogennacrene, limonene, (Z)-p-ocimene. myrcene 15.6 40.7
Annona aternoya 4o 96,3 a-pinene, p-pinena, bicyclogennacrene, gennacrene D, 89.7 66.3
fNit
(16) limonene, bornyl acetate. myrcene. (E)-p-ocimene 6.6 30.0
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Innona chenrndia leaf 28 92,5 elemd, p-eudesrnol, spathulenol, a-eudesmol, calyophyllene 13.1 7.9
(17) 0.4 oxide. guaiol, lirnonene. ymuurolene 79.2 84.4
Innona cherirndia
fNfi 208
(18 )
Annona
haernatantha (17)

Annona rnuricata
(9)

p-caryophyllene. Gcadinene. a-rnuumlene, (E)-2-hexenol,

Annona rnuricata
(11)

Annone rnuricata
(19)
Annona reticu/aiT
(10 ) I 1 I , ..-
Annona leaf 46.8 linalool, a-famesene, acadinol. geraniol. p-pinene, I 15.2 25.0
senegalensis (20) 0.02 a-terpineol. caryophyllenolI, caryophyllenol~~,ij-harene I 31.6 21.8
AnnOna
leaf 39 96.7 a-phellandrene. myrcene, (Z)-p-ocimene. a-pinene, 90.7 71.O
senegalensis
0.5 (E)-p-ocimene, 1,8cineole. limonene. a-gujunene 5.8 25.5
(19.21)
fNa aphellandrene. a-pinerm, myrcene, (E)-p-oclmene, 84.0 67.3
0.08 41 97'1 (Z)-p-cmnene, l.&ineole, limonene, p-caryoptiyilene,ppinene 13.1 29.8
Innona sauamosa

(23)-
-~

Innona squarnosa
(24.25)
Innona squarnosa

germacrene D, p-elemene, a-elemene. elemene, p-pinene.

leaf 36 78.3 pcaryophyllene. a-muurolene. methyl 3-hydroxybutyrate,
acopaene, camphene,. a-pinene
7::; 23.6
53.3
~ -~ -. .
bnona squarnosa 46 82.2 spathulenol. bomyl acetate. myrtenol. bomeol. pinocarveol. 7.0 33.5
peel
(2829) a-campholenic aldehyde 67.0 40.5
spathulenol, germacrene D, elemene. p-pinene,
14.1
fNfi 46 83.3 methyl isoeugenol, a-tetpinene. bornyl acetate, pqmene. 36.6
28'9 51.4
~~~ -. ~~ - y+d!nezp
 134 FOURNIEI m AL.

Table II.Continued

bntifiedl Main compounds (a%)

35 r-cadinol, r-muumlol. spamulenol, acopaene. a-terpineol.

globulol, famesol, viridiflorol 76.4 74.5
pcaryophyllene, a-pinene. a-humulene. a-gujunene. 84.2 20.6
lnnona squamsa root
22 96.3 limonene, yelemene, caryophyllene oxide. camphene.
(3031) 75.7
- peudesmol. a-eudesmd
I ~cedrene,Bcaryophyllene. (€.€)-famesol. cadina-1.4-diene
28 allc-ammadendrene, calamenene, p-elemene, a-bisatmlene
a-humulene, pbisabolene, methyl eugenol
15
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1,5-epoxysaIvial-l-(14)-ene, p-elemene
1,5eponpahrial-l2-(14)-ene.widdrol, camphene, spathulenol
18 Scadinol, linalod, cyperenone, p-elemene. verbenone,
- I caryophyllenol
cyperene. cyperenone, caryophyllene oxide. cadalene.
17 78.6 Belemene, p-guaiena, germacrene D, guaiene. acalacorent
32.7 98.9
Emuurolene. ymuurdene. elemol
Arrabarys
25
cyperene. cyperermone. caryophylleneoxide.
cadalene. mvnenol. cis-caweol. B-caNODhvIlene.

caryophyllene oxide, B-caryophyllene, 1,59poxysalvial-l-(14:

27.3
51.1 I 16.1
62.3

25 ene, acopaenetl-01. caryophyllenol,germacrene D,

phumulene, salvial-l-(l4)-en-l one, spathulenol, Scadinol
1.5-epoxysalvial-l-(14)-ene.camphene, palustrol, cyperenom
25 spamulenol. Scadinol, cyperene. pcaryophyllene, p-cyrnens
ciscarveol

&
nabotrys v e n u e stem bark 20

58
1,5-epoxysahrial4(14)-ene.camphene. ledol, salvial4-(14)
en-1-one. carywhvllene oade. DcafVODhvllene. a-Dinem.
caryophyllenol, spatiulenol
ethyl hexanoate, ethyl octanoate, ethyl bulyrate
p-caryophyllene. ymuumlene, a-famesene, germacrene D.
~~
22.1
63.4 ~
14.6
70.5

aliph. 97.7
_.

Iinalwl, pcresyl-methyl-ether, benzyl benzoate, benzyl

acetate. geranyl acetate, methyl benzoate, benzyl salicylate
Cananga odorate
>lo0 a-humulene. Gcadinene, ycadinene. famesol, (E.0-famesy >>
(64) flower
acetate. geraniol, pfamesene. a-bergamotene. a-muurolene
(+ ref. enclosed)
p-copaene. methyl sallcylate. pinethyl-ansole. mcresyl
acelate, ocresyl acetate, acadinene. neml. eugenol.
(Z)emnamylalcohol, (Epfamesol, phenyl methyl ~ _ _ benozate
_ _ _

--Y
-
54
p-caryophyllene - y-cadinene
benzyll benzoate - a-humulene
Iinalool. tetradecane, germacrene-D, tenzyl acetate. benzyl
benzoate. p-methylanisole, a-pinene, methyl benzoate,
72
Bcaryophyllene, cinnamyl acatate, p-pnena, geranyl acetate
(E,E)-a-famesene, benzyl alcohol
: I linalool. benzvl benzoate. oermacrene D. benzvl acetate.
n-tetradecani, p-methylanLole. cinnamyl ace&. methyl
Cananga odorab
90
(37) ~ benzoate, B-caryophyllene. geranyl acetate.
~~ (€.€)-a-famesene,
- __.a-humulene.
- - - benzyl salicylate -
p-caryophyllene. a-pinene, germacrene D. hexanol,
30 96 1 a-humulene, P-pinene, (Z)-3-hexenol. acopaene,
- ~~
b E d i E e , (E)-Ehexenol
sabinene, myrcene, a-pnene. terpinen-4-ol, yterpinene.
18 98
~
a-terpinene.
-~ p-pinene, hexanol. (Z)-p-ocimene
~ ~ ~ _ _ _ _ _ _ _
y-cadinene. ammadendrene. cyperene. spathulenol.
50
bomyl acetate. acadinol, &famesene, nemlidol
10 ^I I
YY.0
D-famesene. a-phellandrene. Dcadinene.
2.6-dimethyl-2.4,6-oatnene,a-famesene, humulene
(E)-p-xirnene. p-caryophyllene, linalool. germacrene D,
40
a-terpineol. Scadinene. (Z)-3-hexenol.hexanal. acadinol
linalool. trans-linalwl oxide. cis-linalool oxide, a-terpineol.
34 ~~

-
1 stem bark
0.2
43
pocimene. gennacrene D, myrcene. pcaryophyllene.
Gcadinene. Iimonene, a-cadinol, acopaene, a-terpineol.

- - _..
 ESSE".
ANNONACEAE Ons 135

Table Ii.Continued

Analyzed
Annonaceae
ampie yidc
(ref)

Dennenia tripefala fNlt

11 95 p-phenylnitmethane,linalool. nemlidol
14.3) 0.27
1,5-epoxy-4(14)-salvialene. acadinol. spathulenol,
caryophyllene oxide, humulene oxide, a-muuroiene, cyperene,
Enanfia chloranfha Stem bark 25,1 4.0
39 99 p-elemene. calamenene alcohol, 4(14)-salvialen-l-one,
0.2 86.1
(44) S-elemene, cyperenone, a-humulene, r-muuroioi, , 65.0
pcaryophyllene.r-cadomp, torreyoi ~. -
Fifzalania leaf 78.5 0.0
heferopefala (45) to 0.15
0.05_
_ - 4.4 -82.9
__
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Guaneria wregou root bark caryophyllene oxide. a-cadinoi. trans-carveol. spaihuienol, 8.5 21.7
(46) 0.2 Gcadinol. cuminaidehyde, cadalene 69.6 56.4
Guaneria sagofianr fNlt y-terpinene, p-cymene. caryophyllene oxide, pcaryophyllene, 72.6 70.2
nl I
(46) 0.6 L4.J 26.7
~ ~ - - a-terpinez
~ p -
stem bark 87,0 borneol. S-3carene, caryophyliene oxide, limonene. 42.7 62.6
3o
0.3 p-cymene, S-cadinol, camphene 44.3 21.1
Guaneria
wachenheirni (46)

-
leaf
04
33 88.3
pcaryophyllene,caryophyllene oxide, spathulenol,
a-humulene. bomeol, a-pinene, pcymen-8-ol. acopaene,
Seadinene, acubebene
:::; 22.0
65.7
Haplosfichanfhus leaf 2.3,4.5-telrarnethoxyal~l~nzene, eiemicin,
32 98.1
johnsonii (47) 15 acopaene. p-elemene I
Hexalobus leaf geranial. neral, linalool. (E)-anethole, geranioi. I 5.7 79.1
39 95.3
monopatalus(48) 0.53 seiin-11-en4a-ol. caryop[hyllene oxide 84.0 10.6
Miliuse fornenfosa' leaf ,
1,I-cineole
(49) 0 23
Monanfhofaxis (E)-4-phenylb~-3-en-Z-ylacetate. (E)-4-phenyIbut-3%n-2-01,
leaf 18 99.9
cape# (50) __ 4-phenyibutan-2-ylacetate
trans-pinocarveol. spathulenol. cedrol, 6cadinene.
root bark 15.8 37.2
32 81.0 acopaene. acopaen-11-01, caryophyliene oxide,
03 65.2 43.8
Monanfhofaxis __ camphene. bornyl acetate
didine (51) velbenone, caryophyllene oxide, p-humulene. a-humulene.
fNlt 41.0 40.2
34 88.3 pcaryophyllene. pcymene. trans-pinocarveol,
0 35 1 47.3 48.1
~p acopaen-1 1-01, bomeol, acopaene. spathulenol .- .~
ieaf 1.7
18 99.3 (E.E)-a-farnesene,(z)-p-ccimene. myrcene, limonene 98'6 0.0
Monodore brevipes - 002 96.9 ~

(19.21) seed a-phellandrene, a-pinene, myrcene, limonene. tp-p

1 95.2~- 97.9
3.4
20 99.3
a-thujene. p q m e n e ,4.1 1.4
Monodora
seed p-cymene. a-phellandrene.camphene, carvacrol
grandiflora (52)
~

Monodora rnyrisfic; seed

p-phellandrene.1,8cineole
(52) 5
Monodora mynsfie fNlt 99,3 a-phellandrene. a-pinene, limonene, myrcene. a-thujene, 96.1 98.7
14
(219) 40 pcyrnene. linalool 3.2 0.6
Monodora rnyrislics I 21.3 36.7
seed 52 42 pcymene, linalool i mn
(55) 4.6
Monodora rnynsficz a-phdlandrene,pqmene, a-pinene. myrcene,
fNlt 80.6
29 98 4 germacrene D-4-01, spathulenol, Iimonene, p-phellandrene,
(56) 4 56 17.8
&cadinene, a-thujene
leaf 98 P-caryophyllene. a-humulene, a-copaene. a-ptnene. 96 8 6.8
21
Monodora rnynsticz 0 02 a-cubebene, 6-cedinene 12 91.2
(19) seed 97 9 96.8
23 996 a-pheilandrene, a-pinene, myrcene. limonene
_ _

Monodora tenurfoliz
p
- se~

root
~p -
camphene, 3-prenylindole. 6-prenyiindole, nerolidol,
- 1 -17
47 0
-2 : L
16.8
41
(57) _ _ ~-
003 86 a-santaiene. (E)-p-ocimene, p-bisabolene,geranioi. p-selinenel
~ ~~ 22 9- ~
53.1
Mirdora tenurfolu fNlt 84 germacrene D. Gelemene, Scadinene, ycadinene. 82 5 3.2
33
( 5 8 ) 14 -~
a-santalene,
~______
pcaryophyllene 24 ~~
81.7
root 2.45 tnmethoxysiyrene & 3 c a r e x p
20 991
Pachypodanfhiurn 21 p-caryophyllene,linalool
sfaudfir (59) stem bark
24 97 2,4.5-tnmethoxysiyrene. p caryophyllene. 6 3 carene.
14 menthyl acetate. y-terptnene. p-terpinene
leaf 22 99 a-humulene. p caryophyllene, (3-p-ocimene, myrcene, 98 4 21.5
Polyalfhia acopaene. Iimonene, S-cadinene 09 77.8
suaveolen9 (60) myrcene, a-pinene. (Z) p-ocimene, a-humulene, 95 9 77.2
24 994
p-caryophyllene,Iimonene,- p-pinene 35 22.2
~
 136 Fou~lvre~
ET AL..

Annonaceae Analyzed c.v c,3

.amplo y l ~ dMenUlkd ldentltled Main compounds (>2%) C%
, ~' P Z
specl= (ret) camps CIS%
*
(%) ounds
26 85.7 Gcadinol. terpinen-4-ol. caryophyllene oxide, p-humulene. 21.1 22.7
rod
cadina-l,4diene. carvone. a-humulene 64.6 63.0
Unonopsis
gualterioides pcaryophyllene. a-pinene. cyperene. caryophyllene oxide.
a-humulene, p-pinene, pulegone. acopaene. 68.5 24.3
(51) frun 29 90.7
cadina-1 Adiene. y-elemene. valencene, 22.2 66.4
Gcadinene, farnesd
root thymoquinddimethyl ether, benzyl benzoate. bornyl acetate. 0.0 35.6
0.05 l6 74.7 rcadinol, methoxylatedbenzyl benzoate. thymol methyl ether 40.0 4.4
Uvaria charnae 6-cadinene, acadinol. caryophyllene oxide. acopaene.
(61) leaf r-muumlol. pcaryophyllene. calamenene. cubenol, 39.0 10.0
40 70
I 0.1 D-elemene, 6-methyl-5-he~ten9-on~. cadinenol. 31.O 60.0
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~ p-cymene. 1,&cineole
~~~ ~~~~ ~~

bornyl acetate, palchoulenone, cyperene. pcaryophyllene,

Uvaria namrn root barlc 29.1 20.5
21 57.6 borneol, a-gujunene, calamenene, a-muurolene,
(62) 28.5 37.1
p-bisabolene
pcaryophyllene,benzoic acid, benzyl benzoate. a-bulnesene.
Uvaria namrn leaf
66 . p-elemene. a-copaene, germacrene D. caryophyllene oxide, 51.5 8.3
(63) I 0.11 bornyl acetate, 3-hexenol. (E)-P-farnesene. S-elemene. 14.4 57.6
a-guaiene, a-gujunene
Kylopia aethiopica fruit
IMI dl a-pinene, 1&cineole
Kylopia aethiopica
fruit cuminic aldehyde
(65)
Ky/opia aethiopica terpinen-4-01, 1,Bcineole, p-pinene, a-terpineol, 21.6 74.0
fruit
(66) 85.8 cuminic aldehyde. linalool. cuminyl alcohol, bisabolene 54.4 2.0
Kylopia aethiopica i fruit
22
oo sabinene, p-pinene, terpinen-4-ol, a-terpineol. a-pinene, 74.9 91.7
(21.54) I p-phellandrene,a-muurolene,y-terpinene. 1.&cineole 25.1 8.3
Ky/opia aethiopica
fc71 i d: :s P-pinene, a-pinene, a-copaene, 1,8cineole, germacrene D
kylopia aethiopica
f68)
. . I frua
0.4-0.6 1 41 1 82'2 I sabinene, 1,8cineole, terpinen-4-01,
.B-pinene.
. a-pinene. linalool
p-pinene. a-pinene, sabinene. a-phellandrene. 1,&cineole.
I 53.4
28.8
75.6
6.6

74,1 84.1
(69) 4.0 15.2 5.2
trans-pinocarveol,terpinen-4-ol. myrtenol
60.4
34.0 ~

c,,
>>
CIS
28.2
32.5
68.7
0.0

93.4
Xy/opia aromarica 0.9
48.7
43.5

acubenene. Gcadinol. Iimonene. elemol. p-cymene, 19.0

Xylopia frutescens 43.8
90.2 verbenone. P-caryophyllene, germacrene D. Gcadinene. 46.4 71.2
(77) borneol. carvml, p-terpineol,a-humulene, Pcedrene
-
~

trans-pinocarveol, myrtenal, a-pinene. p-cymene, verbenone,

26.9 87.6
88.3 myrtenol. Iimonene, a-terpineol, p-pinene. a-campholenal.
61 4 0.7
- camphene. 1,8cineole. pinocarvone, pinocamphone
Xylopia longifolia 11.9 42.3
94.1 S-cadinol. bornyl acetate. camphene. elemol. cadalene
~ (78) ~~ ________ _ _ ~~- ~~
82;2 ~ 51.8
a-piene, trans-pinocarveol,spamulend;myrtenol,
26.7 83.8
91.8 p-menthadien-Z-ol, terpinen-4-ol, p-pinene, pcymene.
65.1 8.0
- verbenone, acampholenal, pnocarvone, pmenth4,(8)-en-2-onel
~

~~ . - .~
 Ess-
A”ONA(EAE Ons 137

~~

Tablo II. Continud

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:,HI = terpene hydrocarbons; C,H,O, = oxygenated tefpenes;“C,, = mondefpenes, C,, = sesquiterpenes;

diliusa tomentare: syn. Saccopelalum tomenlosum;‘Monanthotaxis cepea: syn. Popowia capan; ‘PoIyaHhia suavmlens: syn. Greenwnycnjendron
rawolens; ‘Xy/opia slaudlii: syn. Xyfopia mayombensis
~~ ~~~~ -~ ~- -~~

Table 111 presents the analysis of some results given in Table 11. About one third of the results from
Table I1 are not included in Table 111 either because constituent proportions were not mentioned, or
the percentage sums of identified constituents were too small (< 70%) to give judicious analysis. When
results are identical for the same species in distinctly different studies, only one is counted. Finally, when
identified constituents are not mainly of terpenic origin, they are not included. In fact, Table 111 shows
all results of only 76 analyses made on several organs from 40 species belonging to 15 genera. Terpene
hydrocarbons and oxygenated terpenes on one hand, monoterpenes and sesquiterpenes on the other
hand, are singled out. Notations CxHy= CxHYOz,and C,, = C,,, are used when the difference between
the contents is below 10%. Finally, it can be concluded from the results presented in Table 111 that fruit
and seed oils contain mainly monoterpene hydrocarbons; leaf oils, sesquiterpene hydrocarbons; and
bark and root oils, oxygenated sesquiterpenes.
The most frequent terpene constituents (those monoterpenes and sesquiterpenes whose yield is
above 2%and are mentioned in more than 5 different studies) are shown in Table N.The skeleton of each
 Table 111. Distribution of hydrocarbons, oxygenated monoterpenes
and sesauiterwnes in different organs of Annonaceae oils

-> < > - <

Organ nb 96 cxys cxys syoz '15 '15 Interpretation
-- '15
-
fruit 22 29 13 5 4 16 1 5 monoterpene hydrocarbons
leaf 21 28 14 2 5 6 1 14 sesquiterpene hydrocarbons
bark and stem bark 16 21 3 3 10 5 2 9 oxygenated sesquiterpenes
root and root bark 11 14 3 0 8 3 1 7 oxygenated sesquiterpenes
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seed 3 4 3 0 0 3 0 0 monoterpenehydrocarbons
flower 2 3 0 0 2 1 0 1
peel 1 1 0 0 1 0 1 0

nb 76 36 10 30 34 6 36
% 100 47 13 40 45 8 47

terpene is also given for all these constituents. These compounds are a-pinene, limonene, p-pinene,
caryophyllene, p-cymene and caryophyllene oxide. These terpenes are present in many oils, therefore
have no special significance in the Annonaceae oils. On the contrary, it can be seen from Table I1 that
some constituents are less common and seem to be more specific to some Annonaceae species; so:
in Annona haematantha, argentilactone is the main constituent of root and stem bark oils.
This rare lactone has still not been found in any other Annonaceae oil;
in all Artabotrys species, 1,5-epoxysalvial-4-(14)-ene is present in a significant amount;
the salvialane skeleton (= isodaucane) of this sesquiterpene is rare;
2,4,5-trimethoxystyrene is a rather rare aromatic compound, which is found in a significant amount
in root and stem bark of Pachypodanthiurn staudtit oils. We have to note that this compound has also
been identified in another Pachypodanthiurn, P. confine (S), but this study is not mentioned in Table I1
because in this particular case the extraction was made by a solvent. Another aromatic compound is
present in a significantamount 2,3,4,5-tetramethoxyallylbemene in Ha~~~ttichanthusjoh~oniileafoil(47).
This study mainly concerns mono- and sesquiterpenes of Annonaceae oils. But in these oils
constituents with other biogenetic origins such as aromatic and aliphatic compounds can be found.
Furthermore, in numerous Annonaceae species, other compounds of terpenoid origin (di- and
triterpenes) have been described, but they are not steam distilled and so they are not present in the oils.
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 139

Table IV. Frequency of principal identified terpenoid compounds in Annonacaae oils

Monoterpenes Skeleton Sesquiterpenes Skeleton

limonene : 32 kadinene : 19
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a-phellandrene : 14 a-cadinol : 10
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caweol : 6 caryophyllane
cuminaldehyde : 6 caryophylleneoxide : 25

a-pinene : 42
b-pinene : 30 1
p-elemene : 17
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3 elemane

J
myrtenol : 1 1 pinane humulene : 22 humulane
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myrcene : 16
(Z)-b-ocimene : 1 1
(E)-p-ocimene : 10
camphene : 16
I. acyclic
cyperene : 8 '

1,5-epoxysalvial-4-(14)-ene: 8
patchoulane
salvialane

bomyl acetate : 1 1
bomeol : 10
89-carene : 9
1 camphane

carane

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