FLAVOUR AND FRAGRANCE JOURNAL, VOL.

8,17-24 (1993)

On the Genuineness of Citrus Essential Oils. Part XL. The

Composition of the Coumarins and Psoralens of Calabrian
Bergamot Essential Oil (Citrus bergamia Risso)
Luigi Mondello, Ildefonsa Stagno d’Alcontres, Rosa Del h c e
Dipartimento Farmaco-chimico, Facolrb a? Farmacia, Universirb di Messina, Italy

Francesco Crisp
Consorzw del Bergamotto, Reggio Calabria, Italy

The content of bergamottin, 5-geranyloxy-7-methoxycoumarin,citropten and bergapten in Calabrian bergamot

essential oil was determined by HPLC. 128 genuine bergamot essential oils, cold-pressed during the year 1992,
were analysed; for each sample the date and area of production of the fruits is known.
The percentage of bergamottin ranges between 1.02% and 2.75%. 5-geranyloxy-7-methoxycoumarinbetween
0.08 and 0.22%, citropten between 0.14% and 0.35%, bergapten between 0.11YO and 0.32%. The mean content of
bergamottin and 5-geranyloxy-7-methoxycoumarindid not vary during the production period, while that of
citropten and bergapten decreased considerably from January to March. There does not seem to be any evident
correlation between the production areas of the fruits and the coumarin composition. The presence of some peaks
absent in genuine bergamot essential oils, has been detected in three bergamot oils, available on the market,
probably because of lime oil addition.
KEY WORDS Cirrus bergamiu Risso Calabrian bergamot oil Coumarins Psoralens Bergamottin
5-Geranyloxy-7-methoxycoumarin Citropten Bergapten Reconstituted bergamot oils

INTRODUCTION and bergamottin (5-geranylo~ypsoralen)~~~ but

only three report quantitative results for 5-geranyl-
The non-volatile residue is a natural odour fixa- 0xy-7-methoxycoumarin.~
tive, which influences the olfactory properties of In recent papers the most successful analytical
citrus essential oils. technique has been high-pressure liquid chroma-
Knowledge of the composition of the non- tography. The most important studies are those of
volatile residue can give useful indications about Di Giacomo and Calvarano3 and of Calvarano el
the genuineness and quality of citrus essential oils aL9 about essential oil produced during the years
and for bergamot oil can represent, moreover, an 1976 and 1977, because these have been carried
objective reference for the evaluation of the prob- out on a large number of samples which represent
lems linked with the photosensitizing activity of the whole production season.
coumarins and psoralens.’ In 1976and 1977 ‘Femminello’and ‘Castagnaro’
Early studies (from 1831 to 1938) about the were the most important cultivars for bergamot oil
composition of the coumarins and psoralens in production in Calabria; but, now, the ‘Fantastico’
bergamot essential oil have been reviewed by cultivar represents more than 90% of the produc-
Giacomo and Calvarano3 and by Lawrence. r
Mossman and Bogert,2 and in later work b Di tive plants. However, the name ‘Fantastico’
sometimes indicates new hybridizations not yet
Most of the studies camed out on the non- classified.
volatile residue of bergamot essential oil have Therefore, we have examined the coumarins
been because of its supposed photosensitizing and psoralens of Calabrian bergamot essential oil
activity and report only the content of bergapten samples which represent the present industrial
(5-metho~ypsoralen).~~~~ Many papers report also production.
the level of citropten (5,7-dimethoxycoumarin)
0882-5734/93/01OO17--08$09 .OO Received 3 July I992
@ 1993 by John Wiley & Sons, Ltd. Accepted 2 October 1992
18 L. MONDELLO ET A L.

EXPERIMENTAL matograms of bergamot oils found on the market

This research was carried out on 128 genuine ber-
gamot essential oils produced during the season
1991/92, which each represent at least 50 kg of
essential oil and 3 commercial bergamot essential
oils which certainly contained reconstituted oils
because GC analysis with a chiral capillary col-
umn showed the presence of both enantiomers of
1ina101.'~
All sampleshave been analysed by normal phase
HPLC, using Waters Associates equipment com-
posed of a 519 pump, gradient controller 600E,
U6K manual injector and a spectrophotometric
detector mod. 484.
Peak integration and quantitative calculation
have been executed by Maxima 825 (W.A.) sys-
tem, using calibrated curve obtained for each
dosed component against a coumarin standard.
The column was a 30cm x 3.9mm i.d. p-Porasil
with particle size of 10 pm. Mobile phase-eluent
A: hexane:ethyl acetate, 9:l; eluent B: hexane:
ethyl alcohol, 9:l.HPLC analyses of genuine ber-
gamot oil samples were performed using eluent A
for 7 minutes, then under a linear gradient of 5 9 5
eluent A:B in 20 minutes with a subsequent hold
for 5 minutes; flow rate 1ml/min; column press-
ure 356 psi; column temperature 30°C; injection
volume 20 pl of a solution obtained diluting to a
value of 4 ml hexane-ethyl acetate (7525) about
200 mg of the genuine essential oil, accurately
weighed, and 0.5ml of a coumarin solution of
known concentration. Detection was by UV
absorbance at 315nm x 2.000 AUFS. The chro-
were performed at 0.500 AUFS.
Five determinations were camed out on the
same solutions of a bergamot oil to check the
reproducibility of the results of the chromato-
graphic analyses (Table 1). Five solutions of the
same bergamot oil were prepared and analysed to
check the reproducibility of the preparation of the
samples (Table 2). Tables 1 and 2 show an excel-
lent reproducibility of results.
Coumarin, bergapten, citropten and berga-
mottin were supplied by Extrasynthese (Genay,
France); 5-geranyloxy-7-methoxycoumarin was
isolated from a sample of Mexican lime essential
oil by chromatography on silica gel column, using
as eluent hexane:ethyl acetate 75:25, and then
purified by crystallization (m.p. 86437°C).
The identity of the 5-geranyloxy-7-methoxy-
coumarin was confirmed by NMR and mass spec-
trometry.
RESULTS
Figure 1 is an HPLC chromatogram of one of
the genuine bergamot oil analysed showing good
resolution of bergamottin, 5-geranyloxy-7-
methoxycoumarin, citropten and bergapten.
Table 3 reports the content of bergamottin,
5-geranyloxy-7-methoxycoumarin, citropten
and bergapten of all the genuine oils examined.
The essential oil production period and the
fruit production areas are indicated for each
sample.

Table 1. Results (percentage content) of five chromatographic analyses carried out

on the same bergamot oil solution
~~ ~~ ~~

Bergamottin 5-Geranyloxy-7- Citropten Bergapten

methoxycoumarin

X 1.73 0.10 0.17 0.18

S 0.038 0.005 0.005 0.007

Table 2. Results (percentage content) of chromatographic analyses carried out

on five samples of the same bergamot oil

Bergamottin 5-Geranyloxy-7- Citropten Bergapten

methoxycoumarin

X 1.73 0.10 0.17 0.18

S 0.049 0.008 0.005 0.012
 COUMARINS AND PSORALENS FROM BERGAMOT OIL 19

Fig. 1. HPLC chromatogram of coumarin fraction of a genuine bergamot essential oil. 1, bergamottin; 2, 5-geranyloxy-7-
methoxycoumarin; 3, citropten; 4, bergapten

Table 3. Percentage content of bergamottin, 5-geranyloxy-7-methoxycoumarin,

citropten and bergapten in genuine bergamot
essential oils
~~

No. of Production Bergamot Bergamottin 5-Geranyloxy-7- Citropten Bergapten

the period of the production methoxycoumarin
sample oils areas"
~~~

1 17 Jan 92 Macellari 1.60 0.12 0.29 0.31

2 17 Jan 92 Pellaro 1.84 0.12 0.20 0.29
3 17 Jan 92 Occhio di Pellaro 1.% 0.13 0.23 0.25
4 17 Jan 92 Ligoni 1.87 0.13 0.23 0.22
5 17 Jan 92 Bovalino 1.86 0.12 0.30 0.27
6 17 Jan 92 Condofuri 1.66 0.12 0.28 0.31
7 17 Jan 92 Curduma 1.20 0.09 0.30 0.22
8 17 Jan 92 San Leo 1.69 0.12 0.27 0.29
9 17 Jan 92 Ligoni 1.99 0.15 0.29 0.25
10 17 Jan 92 Filici 2.14 0.17 0.24 0.16
llb I8 Jan 92 Valanidi 1.75 0.13 0.25 0.20
126 18 Jan 92 Condofuri 1.16 0.08 0.29 0.25
13 18 Jan 92 Filici 1.86 0.13 0.27 0.31
14' 20 Jan 92 Ligoni 1.54 0.11 0.28 0.30
15 20 Jan 92 Filici 1.98 0.14 0.30 0.28
16 20 Jan 92 Pantanello 2.13 0.13 0.24 0.26
17 20 Jan 92 Melito P.S. I .02 0.08 0.35 0.23
18 20 Jan 92 Bovalino 1.66 0.10 0.26 0.26
19 20 Jan 92 Bovetto 2.03 0.13 0.20 0.17
20 20 Jan 92 Cataforio 2.09 0.13 0.24 0.28
21 20 Jan 92 unknown 2.00 0.14 0.26 0.29
22 20 Jan 92 Occhio di Pellaro 1.99 0.12 0.24 0.27
23 20 Jan 92 Filici 2.02 0.13 0.24 0.26
24 20 Jan 92 Mortara 1.84 0.13 0.24 0.21
25 20 Jan 92 cuzzo 1.% 0.12 0.18 0.13
26 21 Jan 92 Spirito Santo . 1.80 0.11 0.19 0.20
27 21 Jan 92 Siderno 1.95 0.15 0.26 0.17
28 21 Jan 92 Filici 1.78 0.12 0.22 0.21
29 21 Jan 92 Bersaglio 2.08 0.15 0.24 0.15
30 21 Jan 92 Filici 2.08 0.13 0. I9 0.19
31 21 Jan 92 Bovetto 1.93 0.14 0.24 0.20
32 21 Jan 92 Macellari 1.60 0.10 0.24 0.31
20 L. MONDELLO ET AL.

Table 3. (conrinued)

No. of Production Bergamot Bergamottin 5-Geranyloxy-7- Citropten Bergapten

the period of the production methoxycoumarin
sample oils areas"

33 21 Jan 92 Filici 2.41 0.18 0.24 0.18

34 22 Jan 92 Brancaleone I .86 0.11 0.20 0.20
35 22 Jan 92 Condofuri 1.31 0.09 0.28 0.25
36 22 Jan 92 Brancaleone 1.57 0.11 0.28 0.26
37 22 Jan 92 Melito P.S. 2.15 0.22 0.29 0.20
38 22 Jan 92 Luppinari 2.08 0.17 0.28 0.23
39 22 Jan 92 Bovalino 1.73 0.11 0.23 0.23
40 22 Jan 92 Luppinari 1.94 0.15 0.29 0.21
41 22 Jan 92 Cartisano 1.70 0.11 0.24 0.26
42 22 Jan 92 Bovetto 1.76 0.11 0.19 0.24
43 23 Jan 92 San Giovanni 1.67 0.11 0.23 0.32
44 23 Jan 92 Brancaleone 1.so 0.11 0.34 0.21
45 23 Jan 92 Spinto Santo 1.52 0.08 0. I6 0.20
46 23 Jan 92 Cataforio 1.63 0.09 0.21 0.21
47 23 Jan 92 Ravagnese 1.94 0.11 0.21 0.19
48 23 Jan 92 Macellari 2.01 0.12 0.21 0.28
49 24 Jan 92 Filici 1.87 0.14 0.25 0.23
50 24 Jan 92 Cataforio 1.60 0.11 0.23 0.32
51 24 Jan 92 Ligonl 1.91 0.14 0.23 0.22
52 24 Jan 92 Melito P.S. 2.14 0.19 0.27 0.16
53 24 Jan 92 Luppinari 2.04 0.17 0.29 0.21
54 24 Jan 92 Cataforio 1.88 0.12 0.22 0.23
55 24 Jan 92 Siderno 1.81 0.17 0.32 0.21
56 24 Jan 92 Cannavb 1.75 0.09 0.15 0.23
57 28 Jan 92 Melito P.S. 2.13 0.14 0.19 0. I8
58 1 Feb 92 Vibo Valentia 1.43 0.08 0.19 0.24
59 3 Feb 92 Mortara 1.76 0.09 0.17 0.18
60 3 Feb 92 Ligoni 1.91 0.14 0.22 0.17
61 3 Feb 92 Siderno 2.04 0.13 0.20 0.23
62 3 Feb 92 Lauaro 2.10 0.13 0.19 0.21
63 3 Feb 92 Vito 1.so 0.09 0.23 0.20
64 4 Feb 92 Pellaro 1.75 0.13 0.22 0.19
65 4 Feb 92 Trumbad 1.61 0.11 0.21 0.15
66 4 Feb 92 Cuzzetta 1.76 0.13 0.25 0.18
67 4 Feb 92 Trapeui 1.61 0.11 0.26 0.24
68 4 Feb 92 Macellari 1.91 0.11 0.18 0.22
69 4 Feb 92 San Giovanni 1.86 0.13 0.23 0.20
70 5 Feb 92 Cuuetta 2.20 0.14 0.19 0.17
71 5 Feb 92 Siderno 1.74 0.14 0.30 0.23
72 5 Feb 92 Valanidi 2.03 0.13 0.21 0.19
73 5 Feb 92 Filici 1.93 0.13 0.21 0. I9
74 5 Feb 92 Spirito Santo 1.73 0.10 0.17 0.18
75 5 Feb 92 Macellari 1.76 0.11 0.21 0.I9
76 5 Feb 92 Filici 2.15 0.13 0.19 0.20
77 5 Feb 92 Ligoni 2. 15 0.13 0.20 0.18
78 5 Feb 92 Filici 1.88 0.12 0.22 0.24
79 6 Feb 92 Siderno 2.09 0.16 0.22 0.15
80 6 Feb 92 Siderno 2.04 0.1 1 0.18 0.22
81 6 Feb 92 Montebello Jonico 1.64 0.13 0.24 0.21
82 6 Feb 92 Bovalino 1.79 0.10 0.22 0.22
83 6 Feb 92 Roccella 1.70 0.11 0.23 0.19
84 6 Feb 92 Cataforio 1.92 0.10 0.17 0.28
85 6 Feb 92 Valanidi 1.48 0.10 0.23 0.22
86 7 Feb 92 Macellari 2.13 0.16 0.22 0.18
87 7 Feb 92 Cataforio 1.88 0.10 0.18 0.25
88 7 Feb 92 Siderno 1.81 0.11 0.21 0. I8
89 7 Feb 92 Valanidi 1.86 0.13 U.21 0.25
90 7 Feb 92 Spirito Santo 1.66 0.09 0.16 0.15
 COUMARINS AND PSORALENS FROM BERGAMOT OIL 21

Table 3. (conrinrced)

No. of Production Bergamot Bergarnottin 5-Geranyloxy-7- Citropten Bergapten

the period of the production methoxycoumarin
sample oils areas”

91 7 Feb 92 Valanidi 1.% 0.12 0.22 0.24

92 7 Feb 92 Macellari 1.98 0.11 0.15 0.19
93 10 Feb 92 Macellari 2.12 0.14 0.19 0.18
94 10 Feb 92 Filici 1.91 0.15 0.16 0.12
95 10 Feb 92 Ligonl 1.63 0.10 0.26 0.23
% 10 Feb 92 Ligonl 2.26 0.12 0.16 0.23
97 10 Feb 92 Montebello Jonico 1.65 0.11 0.24 0.23
98 10 Feb 92 Trapezzi 2.25 0.17 0.19 0.14
99 11 Feb 92 Filici 2.75 0.21 0.27 0.18
100 11 Feb 92 Roccella 1.69 0.12 0.25 0.22
101 11 Feb 92 Cuzzetta 2.03 0.14 0.21 0.18
102 11 Feb 92 Trapezzi 2.45 0.19 0.23 0.15
103 11 Feb92 Fosse di Comi 1.a 0.11 0.20 0.18
104 11 Feb92 Macellari 2.04 0.13 0.17 0.17
105 11 Feb 92 San Giorgio 2.38 0.16 0.19 0.15
106 11 Feb 92 Anno 2.14 0.15 0.22 0.21
107 12 Feb 92 Bovalino 1.85 0.11 0.22 0.20
108 12 Feb 92 Stignano 1.80 0.09 0.18 0.23
109 12 Feb 92 Roccella 1S O 0.09 0.20 0.21
110 12 Feb 92 Valanidi 2.32 0.14 0.20 0.21
111 12 Feb 92 Trapezzi 1.98 0.12 0.21 0.16
112 12 Feb 92 Montebello Jonico 1.78 0.13 0.21 0.17
113 13 Feb 92 Bovetto 2.32 0.18 0.23 0.14
114 14 Feb 92 Melito P.S. 1.84 0.11 0.22 0.22
115 14 Feb 92 Cuzzetta 2.01 0.14 0.21 0.12
116 14 Feb 92 Stignano 1.81 0.09 0.16 0.19
117 14 Feb 92 Bovalino 1.78 0.11 0.21 0.21
118 14 Feb 92 Macellari 2.01 0.14 0.19 0.15
119 14 Feb 92 Melito P.S. 1.79 0.11 0.22 0.22
120 19 Feb 92 Lume 1.85 0.13 0.19 0.14
121 29 Feb 92 Brancaleone 1.57 0.11 0.18 0.18
122 2 Mar 92 Roccella Jonica 1.53 0.10 0.22 0.23
123 4 Mar 92 Cuuetta 2.25 0.13 0.17 0.11
124 4 Mar 92 Pellaro 1.79 0.10 0.15 0.14
125 4 Mar 92 San Giovanni 1.74 0.11 0.14 0.14
126 5 Mar 92 Sidemo 2.34 0.16 0.20 0.17
127 5 Mar 92 Pavigliana 2.01 0.14 0. I9 0.13
I28 5 Mar 92 Pavigliana 1.% 0.13 0.19 0.16

x 1.87 0.13 0.22 0.21

S 0.261 0.026 0.042 0.047
Min. 1.02 0.08 0.14 0.11
Max. 2.75 0.22 0.35 0.32

“A map of the production areas was given in previous papers. ‘5s’6

bAll the samples were from the ‘Fantastico’ cultivar except Nos 11, 12 and 14 which were from the Castagnaro cultivar.

In Table 3 only three samples of essential
oil (Nos 11, 12 and 14) were obtained from ‘Cas-
tagnaro’ fruits and none from the ‘Femminello’
variety; all the others were obtained from ‘Fan-
tastico’ fruits. The same table reports the aver-
age, the standard deviation and the highest and
the lowest values for each component.
In Table 4 our results are compared with those
reerted in the literature and relative to at least
ten certainly genuine oils. From the results given
in Table 4 it seems clear that our results obtained
from bergamottin, 5-geranyloxy-7-methoxycou-
marin and citropten agree with those of the litera-
ture; our results on bergapten agree with those of
Calabrd et d.’* (obtained by TLC), but they have
an average lower than those (statistically more
22 L. MONDELLO ET AL.

Table 4. Our results (percentage content) compared with those from literature

Bergamottin 5-Geranyloxy-7- Citropten Bergapten

methoxycoumarin
X Min. Max. X Min. Max. X Min. Max. X Min. Max.

Our results (1992) 1.87 1.02 2.75 0.13 0.08 0.22 0.22 0.14 0.35 0.21 0.11 0.32
Calvarano' (1%1) 0.29 0.25 0.35 0.61 0.44 0.75
Calabrb e CurrbI2
(1975) 1.8 1.4 2.2 0.12 0.10 0.15 0.18 0.14 0.24 0.22 0.15 0.33
Di Giacomo and
Calvarano3 (1978) 0.29 0.20 0.48
Calvarano, Ferlazzo,
Di Giacomo' (1979) 2.03 1.14 2.73 0.23 0.16 0.30 0.25 0.16 0.40
~ ~ ~

Table 5. Monthly average content per cent of coumarins in bergamot essential oils analysed

January February March

x s Min. Max. X s Min. Max. 2 s Min. Max.

Bergamottin 1.82 0.264 1.02 2.41 1.91 0.254 1.43 2.75 1.95 0.286 1.53 2.34
5-Geranyloxy-7-
rnethoxycoumarin 0.13 0.027 0.08 0.22 0.12 0.025 0.08 0.21 0.12 0.022 0.10 0.16
Citropten 0.24 0.042 0.15 0.35 0.21 0.029 0.15 0.30 0.18 0.W 0.14 0.22
Bergapten 0.23 0.047 0.13 0.32 0.19 0.034 0.12 0.28 0.15 0.039 0.11 0.23

Table 6. Percentage content of cournarins and psoralens of lected in groups containing samples produced in
the samples of reconstituted oils analysed the same month. The average and the standard
deviations of the results were calculated for each
1 2 3
group. Table 5 reports the average values and the
Bergamottin 0.68 1.04 1.16 lowest and the highest values for each parameter.
5-Geran yloxy-7-rnethoxycoumarin 0.37 0.18 0.18 The table demonstrates that the level of 5-
S-GeranyIoxy-8-methoxypsoralen + + + geranyloxy-7-methoxycoumarin remains constant
5-lsopentenyloxy-7-methoxycoumarin + + + for the whole period considered, bergamottin
5-Isopentenyloxy-8-methoxypralen + + +
Citropten 0.10 0.12 0.13 shows a slight not meaningful increase and citrop-
8-Geran y loxypsoralen + + + ten and bergapten respectively show a significant
Herniarin + + + decrease to about 93 of the original content, from
Bergapten 0.04 0.10 0.10 January up to March.
Isopinpinellin + + +
Oxypeucedanin + + +
+ = present. Coumarin Content in Relation to the Production
Areas of the Fruits
significative) reported in l i t e r a t ~ r e ~ and
.~ We tried to check if altitude or latitude of the
obtained by HPLC. fruit production areas influences the composition
We suggest that the changes in bergamot culti- of the coumarin fraction, as it does the volatile
vation in recent years have brought about this fraction of the essential but we found no
lowering of the bergapten content in Calabrian evident connection between the production areas
bergamot essential oils. and the coumarin content of the oils.

Coumarin Content According to the Harvest Reconstituted Oils

Period of the Fruit
The commercial oils examined certainly con-
All the samples were ordered according to tained reconstituted oils since both enantiomers
essential oil production period and they were col- of linalol were present, l4
 COUMARINS AND PSORALENS FROM BERGAMOT OIL 23

11

A 3
4 6
A
Fig. 2. HPLC chromatogram of a reconstituted bergamot oil (A) and of a lime oil (B). 1, bergamottin; 2, 5-geranyloxy-7-
methoxycoumarin; 3, 5-geranyloxy-8-methoxypsoralen;4, 5-isopentenyloxy-7-methoxycoumarin;5 , 5-isopentenyloxy-8-
methoxypsoralen; 6 , citropten; 7, 8-geranyloxypsoralen; 8, herniarin; 9, bergapten; 10, isopinpinellin; 11, ox ucedanin.
(Identification of peaks 3, 4, 5, 7,8, 10 and 11 was done according the paper of McHale and Sheridan.T.)

Reconstituted bergamot essential oils are gener-
ally obtained by mixing terpenes and distilled oils
of different origins, citrus essential oil other than
bergamot oil, linalol, linalyl acetate, and, at times,
small amounts of natural bergamot essential oils.
Table 6 reports the results pertaining to the
samples of reconstituted oils and Figure 2 shows
the chromatograms of a reconstituted oil and of a
Brazilian lime oil. The results reported in Table 6
show that the values of citropten and bergapten
are less than the lowest values of genuine oils in
all samples of reconstituted oils.
Moreover Figure 2 points out that in the recon-
stituted oils there are some peaks that do not
appear in the chromatogram of genuine bergamot
oils, due, according to McHale and Sheridan,’j to
S-geranyloxy-8-rnethoxypsoralen, 5-isopentenyl-
oxy-7-methoxycoumarin, 5-isopentenyloxy-8-meth-
oxycoumarin, herniarin (7-methoxycoumarin)
and isopinpinellin, which, on the contrary, are
present in the chromatogram of lime oil. We sus-
pect that in the reconstituted oils we analysed
there had been addition of lime oil in order to
imitate the spectrophotometric characteristics of
the genuine oils.
Acknowledgements-This research was supported by ‘Minis-
tero dell’Universit8 e della Ricerca Scientifica’of Italy (60%
and 40% research funds) and by National Research Council of
Italy, Special Project ‘Chimica Fine e Secondaria’.
24 L. MONDELLO E T A L.

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