American Journal of Analytical Chemistry, 2010, 2, 70-72
doi:10.4236/ajac.2010.12009 Published Online August 2010 (
Copyright © 2010 SciRes. AJAC
A New Sesquiterpene from Trichilia casarettii (Meliaceae)
Ivo José Curcino Vieira1,2*, Elaine Rodrigues Figueiredo2, Virginia Rodrigues Freitas2,
Leda Mathias1, Raimundo Braz-Filho3, Renata Mendonça Araújo4
1Laboratório de Ciências Químicas-CCT, Universidade Estadual do Norte Fluminense Darcy Ribeiro,
Campos dos Goytacazes, Brazil
2Laboratório de Tecnologia de Alimentos-CCTA, Universidade Estadual do Norte Fluminense Darcy Ribeiro,
Campos dos Goytacazes, Brazil
3Universidade Estadual do Norte Fluminense Darcy Ribeiro, Campos dos Goytacazes, Brazil
4Departamento de Química-CCET, Universidade Federal do Rio Grande do Norte, Natal, Brazil
Received July 1, 2010; revised July 27, 2010; accepted August 2, 2010
The dichloromethane extract of the air-dried stems of Trichilia casarettii afforded a new sesquiterpene (1),
lupeol, stigmasterol, campesterol and sitosterol. The structure of 1 was elucidated by extensive one-and two-
dimensional nuclear magnetic resonance and mass spectrometry.
Keywords: Trichilia Casarettii, Meliaceae, Sesquiterpene
1. Introduction
The Meliaceae family has attracted much interest among
bioproduction phytochemists because of its very com-
plex and diverse chemical structures and its biological
activity, mainly against insects [1-3]. The Trichilia genus
(Meliaceae) includes about 230 species distributed
throughout tropical America which are recognized for
their significant economic importance and high commer-
cial value. The genus is rich in terpenoids, including
triterpenes, limonoids, steroids and other terpenes de-
rivatives [3-5].
In previous the activity of aqueous extract of leaves
and twigs from T. casarettii was evaluated on Spodop-
tera frugiperda (J. E. Smith) development in laboratory
conditions [6]. To the best of our knowledge, the litera-
ture reports no chemical investigation evaluation of T.
casarettii native of Americas [7]. This stimulated our
interest in the present work, involving isolation and
structural elucidation of the constituents of the stems of
this species. Then, we report the isolation of new ses-
quiterpene 1 (Figure 1) of T. casarettii DC. The stems
also afforded lupeol, stigmasterol, campesterol, sitosterol
and fatty acid esters.
The stems from T. casarettii DC., was collected on
November 2006, at Vale do Rio Doce Cia., Linhares
City, Espírito Santo State, Brazil. A voucher specimen
(No 449) was deposited at Vale do Rio Doce Cia. Her-
2. Results and Discussion
Comound 1 (Figure 1) was obtained as white powder
(MeOH), mp 121-122C, and which is optically active
with an = -18.1 (CHCl3, c 0.002). Its IR spectrum
(KBr disk) obtained in spectrometer Shimadzu, model
FTIR-8300, showed bands at max 3433 (O-H stretching),
3394 (O-H stretching) cm-1. Comparative analysis using
spectrometer Brüker, DRX model [(operating at 400 (1H)
and 100 (13C) MHz, respectively, in pyridine-d5)] of the
{1H}- and DEPT 135°-13C NMR spectra (Table 1) re-
vealed signals corresponding to 15 carbon atoms. These
data allowed us to recognize the presence of signals cor-
responding to three nonhydrogenated carbons [(C)3: all sp3
(including two bound to an oxygen atoms at
C 71.51 and
71.58)], two methine [(CH)2: all sp3, two α to a carbinolic
carbon atom at
C 55.64/
H 1.58 and
C 51.14/
H 1.60,
correlated in the HMQC spectrum with 1H chemical
][ D
10 9
Figure 1. Chemical structure of ambrosanoli-10, 11-diol (1).
Copyright © 2010 SciRes. AJAC
Table 1. 13C (100 MHz) and 1H NMR (400 MHz) data of compound 1 in pyridine-d5,
in ppm, J in Hz and multiplicities, in
5 35.08 - 2H-4; 3H-15 H-7
10 71.51 - 2H-9; 3H-14
11 71.58 - H-7; 3H-12; 3H-13
1 55.64 1.60-1.52 (m) 2H-9; 3H-14; 3H-15
7 51.14 1.62-1.54 (m) 3H-12; 3H-13
2 21.01 1.60-1.56 (m)
1.54-1.50 (m)
3 23.47 1.85 (br s, 11.0)
1.60-1.57 (m) 2H-2; 2H-4
4 45.77 1.44-1.40 (m)
1.14-1.12 (m) 2H-3 3H-15
6 42.08 1.38-1.36 (m)
1.10-1.02 (m) 2H-4; 3H-15
8 22.58 2.64 (br s, 12.0)
1.39-1.37 (m)
9 44.55 1.98 (br s, 12.0)
1.75-1.78 (m) 3H-14
12 28.24 1.38 (s) H-7; 3H-13
13 28.20 1.38 (s) H-7; 3H-12
14 23.51 1.31 (s) 2H-9
15 19.56 0.93 (s) 2H-4; 2H-6
shifts, respectively], six methylene [(CH2)6, including
one α to a carbinolic carbon atom at
C 44.55/
H 1.98 and
1.72] and four methyl [(CH3)4: including three linked to a
carbinolic carbon atom at
C 28.24/
H 1.38,
C 28.20/
1.38 and
C 23.51/
H 1.31] carbon atoms, allowing us to
deduce the expanded molecular formulae (C)(C-OH)2
(CH)2 (CH2)6 (CH 3)4 = C15H28O2 for 1. The high-resolu-
tion electrospray ionization mass spectra (HR-ESIMS) of
1 obtained in mass spectrometer, model LCMS-IT-TOF
(225- 07100-34, Shimadzu) showed a pseudomolecular
ion at m/z 263.1988 [M+Na]+, with the calculated value
for C15H28O2Na being 263.1987. The molecular formula
indicated an index of hydrogen deficiency of two. Thus,
with 1H and 13C NMR spectral data and the compound
bicyclic is compatible with the carbon skeleton ses-
quiterpenic of the ambrosanolide type [8].
In the 1H NMR spectrum, three singlet signals were
observed at
H 1.38 and
H 1.31, characteristic of a
methyl groups linked to two carbinolic carbons, and one
singlet signal at
H 0.93, corresponding to the signals at
C 28.24 (CH3-12), 28.20 (CH3-13), 23.51 (CH3-14) and
19.56 (CH3-15) in the 13C NMR spectrum, suggesting the
presence of two hydroxyl groups. The HMBC spectrum
allowed us to confirm these long-range correlations (Ta-
ble 1) through the signals corresponding to C-10 (
71.51) with the singlet observed at
H 1.31 (3H-14, 2JCH)
and C-11 (
C 71.58) with the two singlets observed at
1.38 (3H-12 and 3H-13, 2JCH). This deduction was cor-
roborated by the long-range correlations of methyne
carbons CH-1 (
C 55.64) with both 3H-14 and 3H-15 (
1.31 and 0.93, 3JCH) and CH-7 (
C 51.14) with both
3H-12 and 3H-13 (
H 1.38, 3JCH) observed in the HMBC
spectrum (Table 1). Thus, these data allowed us to rec-
ognize the presence of hydroxyl groups at C-10 (δC 71.51)
and C-11 (δC 71.58).
The relative stereochemistry of 1 was determined from
the spatial dipolar interaction revealed by the 1H-1H-
NOESY spectrum, summarized in Figure 2. The 1H-1H-
NOESY spectrum of 1 allowed characterization of the
ring-junction (CH-1 with C-5) of the bicyclic system in-
volving the seven and five-rings as trans. The relative
stereochemistry indicated in 1 was deduced by the spatial
dipolar interaction observed in the 1H-1H-NOESY spec-
trum between hydrogen atom H-7 with H3-14 and H3-15
indicating that both are -oriented. The spatial dipolar
interaction observed between H-1 and H-6b and absence
of spatial interaction between H-1 with both, H3-14 and
H3-15, respectively, indicating that H-1 was -oriented in
agreement with a trans ring-junction.
Figure 2. Selected NOESY correlations and relative stereo-
chemistry for compound 1. Arrows denote the main NOESY
Additional spatial interaction is shown in Figure 2.
Therefore, the structure of the new sesquiterpene (Figure
1) isolated from T. casarettii was defined as am-
brosanoli-10,11-diol (1) (30 mg, 0.0433%).
The structures of lupeol [9], -sitosterol [10] and
stigmasterol [10] were deduced by comparison of their
1H and 13C NMR spectral data with those reported in the
3. Acknowledgements
The authors are grateful to Fundação de Amparo à Pes-
quisa do Estado do Rio de Janeiro (FAPERJ) for grants
and to Conselho Nacional de Desenvolvimento Científico
(CNPq-Brazil) for a research fellowship and grants.
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