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Volatile Compounds of Cassia grandis L. f. Fruit from

Cuba
a
J. A. Pino
a
Instituto de Investigaciones para la Industria Alimenticia , Carretera al Guatao km 3½,
La Habana, 19200, Cuba
Published online: 08 Dec 2011.

To cite this article: J. A. Pino (2010) Volatile Compounds of Cassia grandis L. f. Fruit from Cuba, Journal of Essential Oil
Research, 22:6, 599-601, DOI: 10.1080/10412905.2010.9700409

To link to this article: http://dx.doi.org/10.1080/10412905.2010.9700409

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 M. indica
M. indica var. coquinho leaf oil have been tested for cytotoxic
properties. It has been reported that a-humulene (7.2%) shows
activity against MCF-7, PC3, A-549, DLD-1, M4BEU and
CT-26 cell lines (14). Caryophyllene oxide (5.6%) exhibited a
modest cytotoxic activity, against tumor cell lines (15,16). The
elemene sesquiterpenes (1.7%) have also been reported to be
cytotoxic (17). Moreover, an interesting anticancer activity in
the leaf oil of M. indica var. coquinho was found, suggesting
the presence of very active sesquiterpenes.
Acknowledgements
The authors are grateful to Fundação de Apoio ao Desenvolvimento
de Ensino, Ciência e Tecnologia de Mato Grosso do Sul (FUNDECT/
MS) and UFMS for the financial support. The authors also thank to
CNPq for the IC and DCR scholarships.
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Volatile Compounds of Cassia grandis L. f. Fruit
from Cuba
J. A. Pino*
Instituto de Investigaciones para la Industria Alimenticia Carretera al Guatao km 3½, La Habana 19200, Cuba
Abstract
Volatile compounds were isolated from Cassia grandis fruit by simultaneous distillation-solvent extraction. The
volatile concentrate was examined by GC and GC/MS. A total of 108 compounds were identified (30.47 mg/kg), from
which linalool (31.5% of the total volatiles) was the major compound.
Key Word Index
Cassia grandis, Fabaceae, fruit volatiles, linalool.
*Address for correspondence
1041-2905/10/0006-0599$14.00/0­—© 2010 Allured Business Media
Vol. 22, November/December 2010 Journal of Essential Oil Research/599
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 Pino
Table I. Volatile compounds of Cassia grandis fruit
Compound RI mg/kg
isovaleraldehyde 650 1.41
2-methylbutanal 654 0.85
1-penten-3-ol 673 0.07
1-penten-3-one 678 0.12
2,3-pentanedione 700 t
pentanal 706 0.02
acetoin 720 t
acetal 730 0.04
isoamyl alcohol 740 0.45
2-methylbutanol 742 0.27
dimethyl disulfide 744 0.41
(E)-2-pentenal 754 0.03
ethyl isobutyrate 755 t
(Z)-2-pentenol 774 t
isobutyric acid 785 t
hexanal 802 0.14
2-furfural 837 0.17
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(E)-2-hexenal 855 0.12
(Z)-3-hexenol 859 t
hexanol 871 t
isovaleric acid 885 0.95
2-methylbutyric acid 887 1.13
valeric acid 918 t
a-pinene 939 t
camphene 954 0.05
1-propylbenzene 959 0.03
benzaldehyde 960 1.61
dimethyl trisulfide 970 1.39
sabinene 975 t
b-pinene 979 0.06
1-octen-3-ol 980 t
6-methyl-5-hepten-2-one 986 t
myrcene 991 0.05
dehydroxy-trans-linalool oxide 993 0.03
dehydroxy-cis-linalool oxide 1008 0.05
a-terpinene 1017 0.02
p-cymene 1025 0.04
1-propenylbenzene 1027 0.02
limonene 1029 0.18
1,8-cineole 1031 0.59
(Z)-b-ocimene 1036 0.12
benzyl alcohol 1038 t
phenylacetaldehyde 1042 0.57
(E)-b-ocimene 1050 0.09
g-terpinene 1060 0.04
acetophenone 1065 0.36
trans-linalool oxide (furanoid) 1073 0.27
cis-linalool oxide (furanoid) 1087 0.29
terpinolene 1089 t
o-guaiacol 1090 t
methyl benzoate 1093 t
linalool 1097 9.59
isoamyl isovalerate 1105 0.22
2-phenylethanol 1107 0.04
RI = Retention indices on HP-5MS; t = trace (< 0.01 mg/kg)
600/Journal of Essential Oil Research Vol. 22, November/December 2010
Compound RI mg/kg
amyl isovalerate 1108 0.21
camphor 1146 0.41
lilac aldehyde B 1148 0.14
lilac aldehyde A 1155 0.17
borneol 1169 t
ethyl benzoate 1173 0.08
trans-linalool oxide (pyranoid) 1176 0.05
terpinen-4-ol 1178 0.12
p-cymen-8-ol 1183 0.01
a-terpineol 1189 0.86
dimethyl tetrasulfide 1232 0.07
nerol 1234 0.12
(Z)-3-hexenyl 2-methylbutyrate 1235 t
hexyl 2-methylbutyrate 1236 t
1-phenyl-1-butanone 1251 t
geraniol 1254 0.31
geranial 1262 0.02
bornyl acetate 1289 0.02
lavandulyl acetate 1291 t
undecanal 1307 0.07
p-vinylguaiacol 1312 0.10
a-terpinyl acetate 1349 0.45
eugenol 1359 0.34
(E)-isosafrole 1375 t
a-copaene 1377 0.04
methyl (Z)-cinnamate 1379 0.09
b-elemene 1391 0.15
methyl eugenol 1404 0.17
b-caryophyllene 1419 0.41
(E)-cinnamic acid 1454 0.38
a-humulene 1456 0.26
ethyl (E)-cinnamate 1467 0.18
germacrene D 1485 0.05
b-selinene 1490 0.13
a-selinene 1498 0.10
g-cadinene 1514 t
d-cadinene 1523 0.02
dodecanoic acid 1567 0.08
spathulenol 1578 0.03
caryophyllene oxide 1583 0.23
isobutyl (E)-cinnamate 1642 0.07
b-eudesmol 1651 0.02
tridecanoic acid 1667 0.15
pentadecanal 1710 0.03
isoamyl (E)-cinnamate 1741 0.97
tetradecanoic acid 1780 0.10
ethyl tetradecanoate 1792 0.01
benzyl salicylate 1863 t
pentadecanoic acid 1878 0.08
hexadecanoic acid 1991 1.14
ethyl hexadecanoate 1995 0.10
isopropyl hexadecanoate 1999 0.02
ethyl octadecanoate 2197 0.04
 C. grandis
Plant Name and Source
Fruits of Cassia grandis L.f. (Fabaceae) (1 kg) were har-
vested on trees at El Cano, near Havana. A voucher specimen
of the plant was deposited at the Herbarium of the National
Botanic Garden in Havana.
Previous Work
Cassia grandis L.f., commonly named cañandonga (Cuba),
carao (Costa Rica), bukut or stinking toe (Belize), and pink
shower (Florida), is a medium-sized tree, up to 20 m tall,
semi-deciduous, young branches and inflorescence covered
with a rusty colored lanate indumentum. Leaves with 10–20
pairs of leaflets, petiole 2–3 cm long, lanate, leaflets subsessile,
elliptical-oblong, 3–5 cm x 1–2 cm, subcoriaceous, rounded at
both ends. Inflorescence a lateral raceme, 10–20 cm long, 20–40
flowered; flowers with sepals 5–8 mm long, petals initially red,
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fading to pink and later orange. Fruit pendent, compressed,
20–40 cm long, 3–5 cm in diameter, blackish, glabrous, woody,
rugose; inside, transversely oriented compartments with papery
walls contain flattened, round, tan-colored seeds (1.5 cm) as
well as large amounts of thick, strong-smelling, dark-colored
sweetish pulp. This fluid, whose odor can be characterized as
being unpleasant at best, is easily detected when pods have
fallen and broken under the trees. The pungent pulp found
abundantly in the pods is eaten alone or sometimes mixed with
milk and used as refreshment (1). The fruit is reputed to cure
anemia and is used as a natural herbal remedy for a variety of
ailments (2). Cassia grandis tree is mainly distributed from
southern Mexico, to Surinam and Brazil.
A review of the literature reveals that the fruit volatiles of
this species have not been the subject of previous studies.
Present Work
A portion of 100 g of fruits (without seeds) and 500 mL
of distilled water were immediately subjected to the isolation
of volatiles. The isolation was carried out by simultaneous
distillation-solvent extraction with 25 mL of previous distilled
diethyl ether for 30 min in a Likens-Nickerson apparatus.
Internal standard (0.87 mg of methyl nonanoate) was added
to the supernatant before isolation. The extract was dried over
anhydrous sodium sulfate and concentrated with a Kuderna-
Danish microapparatus with a 10-cm Vigreux column to 1 mL
and then, to 0.2 mL with a gentle nitrogen stream.
An HP 6890 Series II with flame ionization detector and with
a fused silica HP-5MS capillary column (60 m x 0.25 mm x 0.25
μm) was used. The temperature program was 2 min isothermal
at 50oC and then 40–220oC at a rate of 4°C/min. The carrier flow
rate was 1 mL/min. Injector and detector temperatures were
kept at 220oC. Volumes of 1 mL were injected with a split ratio
Vol. 22, November/December 2010 Journal of Essential Oil Research/601
of 1:10. Chromatographic retention indices were calculated of
separated compounds relative to a C6-C25 n-alkanes mixture.
Semiquantitative analysis of the compounds was performed
by assuming that component response factors were the same
as the response factor for the internal standard.
GC/MS was performed on a Hewlett-Packard series
6890 gas chromatograph equipped with an HP-5MS fused
silica column (30 m x 0.25 mm x 0.25 mm) and an HP-5973
mass-selective detector was used. The chromatographic condi-
tions were the same as those described for GC-FID. Carrier
gas (He) flow rate was 1 mL/min. The detector operated in
electron-impact mode at 70 eV by 1.8 scans/s. Detection was
performed in the scan mode between 30–400 Daltons. Con-
stituents were identified by comparison of their mass spectra
with those of authentic standards or those in NBS, Wiley, and
NIST libraries, and in-house Flavorlib library. Identification
was confirmed in many compounds by their relative retention
indices. Mass spectra and retention indices from the literature
(3) were also compared.
The volatile compounds identified in the fruits of C. grandis
grown in Cuba are tabulated in Table I. One-hundred-eight
volatiles were identified which constituted more than 98%
of the total composition (30.47 mg/kg). The most prominent
compound was linalool (31.5%). Other major compounds were
isovaleraldehyde (4.6%), isovaleric acid (3.1%), 2-methylbutyric
acid (3.7%), benzaldehyde (5.3%), dimethyl trisulfide (4.5%)
and hexadecanoic acid (3.7%). Linalool with its floral-woody
odor with a faintly citrusy note, isovaleraldehyde with its acrid-
pungent note, isovaleric acid and 2-methylbutyric acid with
their pungent-acid odor, benzaldehyde with its powerful sweet
note, reminiscent of freshly crushed almonds, and dimethyl
trisulfide with the penetrating odor of fresh onion (4), evidently
have an important contribution to the odor of the fruit; while
hexadecanoic acid is virtually odorless.
Acknowledgments
The author thanks Elda Roncal and Yojhansel Aragüez for their
technical assistance.
References
1. J.T. Roig, Diccionario Botánico de Nombres Vulgares Cubanos.
Editorial Cientifico-Técnica. La Habana, Cuba (1988).
2. J. Tillán-Capó, J. Rodríguez-Chanfrau, J. M. Gómez-Mirabal, Z.
Pardo-Ruíz and S. Agüero- Fernández, Actividad antianémica de la
Cassia grandis L. Rev. Cubana Farm. 38(3), 130-133 (2004).
3. R. P. Adams, Identification of Essential Oil Components by Gas
Chromatography/Quadrupole Mass Spectroscopy. Allured Publ.
Corp., Carol Stream, IL (2001).
4. S. Arctander, Perfume and Flavor Chemicals. Det Hoffensbergske
Etablissement, Copenhagen, Denmark (1969).