Ceramides and cytotoxic constituents from Ficus glumosa Del. (Moraceae)

Article abstract of DOI:10.1590/S0103-50532012000300015

Chemical investigation of the stem bark of Ficus glumosa (Moraceae) yielded two new ceramides (2R,7E)-2-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxyhexadecan-2- yl]hexacos-7-enamide and (2R)-N-{(2S,3S,4R,9Z)-1-O-[(β-D-glucopyranosyl]-3, 4-dihydroxyheptadec-9-en-2-yl}-2-hydroxypentacosanamide together with twenty one known compounds. The structures were established using NMR data, mass spectrometry, chemical transformation and by comparison with the reported data. Twenty one compounds were further tested against the prostate cancer PC-3 cell line and six of them revealed cytotoxic effect. Dongnoside E was the most active compound with an IC₅₀ 0.75 μmol L^-1 against the cancer cells line PC-3 while the reference drug doxorubicin displayed 0.91 μmol L^-1. This compound also proved to inhibit the cell growth of the fibrosarcoma cancer HT1080 (IC₅₀ 0.7 μmol L^-1).

Full text of DOI:10.1590/S0103-50532012000300015

J. Braz. Chem. Soc., Vol. 23, No. 3, 482-487, 2012.
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Article
A
Ceramides and Cytotoxic Constituents from Ficus glumosa Del. (Moraceae)
Frédéric Nana,a,b Louis Pergaud Sandjo,*,a Félix Keumedjio,a Pantaléon Ambassa,a
Rizwana Malik,b Victor Kuete,c Vincent Rincheval,d Muhammad Iqbal Choudharyc and
Bonaventure Tchaleu Ngadjui*,a,e
aDepartment of Organic Chemistry, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon
bH. E. J. Research Institute of Chemistry, International Center for Chemical and Biological
Sciences, University of Karachi, Karachi, Pakistan
cDepartment of Biochemistry, University of Dschang, P.O. Box 67, Dschang, Cameroon
dLaboratoire de Génétique et Biologie Cellulaire Bâtiment Fermat - Maison 4, Niveau 2, 45,
Avenue des Etats-Unis, 78035 Versailles Cedex, University of Versailles St Quentin-en-Yvelines, France
eDepartment of Pharmaceutical Sciences and Traditional Pharmacopeia, Faculty of Medicine and
Biomedical Sciences, University of Yaoundé I, P.O. Box 8664, Yaoundé, Cameroon
A investigação química da casca do caule de Ficus glumosa (Moraceae) deu origem a duas
novas ceramidas (2R,7E)-2-hidróxi-N-[(2S,3S,4R)-1,3,4-trihidróxihexadecano-2-il]hexacos-7-
enamida e (2R)-N-{(2S,3S,4R,9Z)-1-O-[(β-D-glucopiranosil]-3,4-dihidróxiheptadec-9-eno-2-il}-
2-hidróxipentacosanamida, em conjunto com vinte e um compostos conhecidos. As estruturas
foram estabelecidas usando-se dados de RMN, espectrometria de massas, transformação química
e por comparação com dados relatados. Vinte e um compostos foram posteriormente testados
contra células de câncer de próstata PC-3 e seis deles revelaram efeito citotóxico. Dongnósido
E foi o composto mais ativo, com IC50 de 0,75 µmol L-1 contra células de câncer PC-3, enquanto
o medicamento de referência doxorrubicina, apresentou IC50 de 0.91 µmol L-1. Este composto
também demonstrou inibir o crescimento de células do câncer de fibrossarcoma HT1080 (IC50
0,7 µmol L-1).
Chemical investigation of the stem bark of Ficus glumosa (Moraceae) yielded two new
ceramides (2R,7E)-2-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxyhexadecan-2-yl]hexacos-7-enamide
and (2R)-N-{(2S,3S,4R,9Z)-1-O-[(β-D-glucopyranosyl]-3,4-dihydroxyheptadec-9-en-2-yl}-
2-hydroxypentacosanamide together with twenty one known compounds. The structures were
established using NMR data, mass spectrometry, chemical transformation and by comparison with
the reported data. Twenty one compounds were further tested against the prostate cancer PC-3
cell line and six of them revealed cytotoxic effect. Dongnoside E was the most active compound
with an IC50 0.75 µmol L-1 against the cancer cells line PC-3 while the reference drug doxorubicin
displayed 0.91 µmol L-1. This compound also proved to inhibit the cell growth of the fibrosarcoma
cancer HT1080 (IC50 0.7 µmol L-1).
Keywords: Ficus glumosa, ceramides, glumoamide, glumoside, dongnoside E, cytotoxicity
Introduction
Coast, the aqueous decoction of the leaves of F. glumosa is
prescribed in traditional pharmacopeia to relieve chest pain
and to treat lung diseases such as bronchitis, pneumonia
and cough.2 The aqueous decoction of its stem bark is
rather used in Central African Republic as oral solution
to cure gingivitis, caries, and tooth aches.3 Additionally,
the methanolic extract of the stem bark of F. glumosa has
demonstrated in vivo antidiabetic and in vitro antioxidant
Ficus glumosa is a small to medium-sized tree with 5
to 10 m tall; it may become a large tree reaching 20 m with
a trunk of about 2 m of girth. Ficus species also produce
white latex like commonly see in the Moraceae.1 In Ivory
*e-mail: plsandjo@yahoo.fr, ngadjuibt@yahoo.fr

Vol. 23, No. 3, 2012
Nana et al.
483
activities.4 The positive reactions of the diluted crude
extract to FeCl3, Liebermann Burchard, and Molish reagent
associated to the traditional uses prompted us to look for
the secondary metabolites of this plant and to evaluate
their cytotoxicity.
We herein report the structure elucidation of two new
ceramides and the cytotoxicity of some compounds isolated
from F. glumosa.
with a gradient from Hex-EA to EA, afforded 15 (6 mg),
11 (5.5 mg), 13 (6.3 mg), 14 (5.7 mg), 22 (4.6 mg) and 19
(10 mg). Fraction D was loaded on reverse phase silica
RP18 CC and eluted with a gradient H2O-MeOH, yielding
20 (3.1 mg), 21 (3.8 mg), 18 (5.4 mg), 23 (12 mg), and
17 (7 mg).
(2R,7E)-2-Hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxy-
hexadecan-2-yl]hexacos-7-enamide (1)
Experimental
Whitepowder;mp127.0-127.3°C;Rf (2/3, DCM-MeOH
19:1); [α] +10.5 (c 0.03, THF); IR (KBr disc) νmax/cm-1:
3330, 3203, 2918, 2850, 1620, 1544, 1263; HR-ESI-MS m/z
682. 6319 [M + H]+, 668.6182 [M – CH2 + H]+, 654.6033
General procedure
1
Melting points (mp): electro thermal IA 9000 apparatus,
uncorrected; optical rotation: JESCO P-2000 polarimeter ;
IR (KBr disc): JASCO A-302 spectrophotometer;
HR-EI-MS and LR-EI-MS: JOEL MS and FLINNIGAN
MAT SSQ-700 apparatus, respectively; 1 and 2D NMR:
Brüker AM-300 and DRX-400 MHz with TMS as internal
reference. Preparative TLC and analytical TLC plates silica
G60 type MERCK. Columns chromatography: normal
phase SiO2 0.063-0.200 mm, reverse phase silica RP18.
[M – C2H4 + H]+, 640.5844 [M – C3H6 + H]+; H and
13C NMR see Table 1.
Acetylation and oxidative cleavage of 1
An amount of 3 mg of 1 was dissolved in 3 mL of
pyridine and treated with 3 mL acetic anhydride under
magnetic stirring for 6 h at room temperature. The
acetylated compound was obtained by concentration of
medium under vacuum. Comparative TLC revealed the
formation of a non polar compound which was further
dissolved in 4 mL of THF-H2O (9:1) and treated with
5 equiv. of KMnO4 and NaIO4 each. The medium was
stirred at room temperature overnight and poured onto
water. The organic layer obtained by extraction with
n-butanol was subjected to de-acetylation using MeONa
in MeOH overnight at room temperature. The medium was
concentrated under vacuum, treated with aqueous solution
of 1 mol L-1 HCl and extracted with EA yielding compound
1a which was characterized by ESI-MS which gave the
pseudo-molecular ion at m/z 448.
Plant material
The stem bark of F. glumosa was collected in March
2009 in Makenene, central region of Cameroon and
identified by the national herbarium where a specimen
was deposited under the registration 28151/SRF/Cam
(Makenene 1972).
Extraction and isolation
Air-dried powder (5 kg) of the stem bark of F. glumosa
was macerated in a CH2Cl2-MeOH (1:1, 6 L) mixture for
48 h. The diluted extract was concentrated under reduced
pressure to afford 405 g of a dark residue which was
dissolved in water and extracted successively with hexane
(Hex), CH2Cl2 (DCM), ethyl acetate (EA) and n-butanol
to give fractions A (12 g), B (15.3 g), C (20 g), and D
(89.4 g), respectively. Fraction A was subjected to silica
gel column chromatography (CC) eluted in the gradient
conditions with Hex, Hex-DCM and DCM-EA, affording
compounds 3 (3.5 mg), 16 (3.7 mg), 4 (4.0 mg), 5 (4.0 mg),
6 (3.2 mg), and 7 (5.3 mg), in order of elution. Compounds
1 (7.5 mg) and 2 (6.8 mg) were precipitated with acetone
in the sub-fractions eluted with DCM-EA 19:5 and 9:1,
respectively. Fraction B was subjected to silica gel CC and
eluted in the gradient conditions with Hex-DCM, DCM and
DCM-MeOH to give compounds 8 (5.4 mg), 9 (5.1 mg), 10
(6.2 mg), and 12 (4.5 mg). SiO2 CC of fraction C, eluted
(2R)-N-{(2S,3S,4R,9Z)-1-O-[(β-D-glucopyranosyl]-3,4-
dihydroxyheptadec-9-en-2-yl}-2-hydroxypentacosanamide
(2)
White powder; mp 199.6-199.8 °C; Rf (2.5/3,
DCM-MeOH 9:1) [α] +17 (c 0.035, THF); IR (KBr disc)
ν
max/cm-1: 3402, 1620, 1544; HR-ESI-MS m/z 844.6897
[M+H]+; 1H and 13C NMR see Table 1.
Methanolysis of 1 and 2
An amount of 1.5 mg of 1, and 2 mg of 2 were separately
refluxed in 2 mL of MeOH and 2 mL of aqueous solution
of 1 mol L-1 HCl for 18 h under magnetic stirring at 70 °C.
An aqueous solution of NaHCO3 was used to neutralize
the medium which was further extracted with DCM. The
organic fractions were purified by CC on silica gel eluted

484
Ceramides and Cytotoxic Constituents from Ficus glumosa Del. (Moraceae)
J. Braz. Chem. Soc.
OH
1
3
OH
O
4
16
HN
OH
1'
8'
26'
HO
3'
7'
Compound 1
25'
2'
1
HO
O
OH
O
6''
3''
NH OH
OH
HO
HO
10
O
1''
11
5
OH
17
Compound 2
O
O
OH
O
OH
O HO
OH
O
HO
HO
O
O
O
O
OH
HO
O
HO
OH
HO
OH
Compound 23
with Hex-EA (4:1). The residual oil of both compounds
were identified by EI-MS from peaks at m/z 424 [C27H52O3]+.
and 426.3 [C27H54O3]+., corresponding to the fatty acid
methyl esters (2R)-2-hydroxyhexacos-7-enoic acid methyl
ester 1b and (2R)-2-hydroxypentacos-7-enoic acid methyl
ester 2a.
diphenyltetrazolium bromide)5 assay for the prostate cancer
PC-3 cell line and flow cytometry for the fibrosarcoma
cancer HT1080 cell line.6 The compounds were dissolved
with DMSO and incubated with the cells for 48 h. The
drug references used were doxorubicin and etoposide for
PC-3 and HT1080, respectively. Furthermore, the IC50
were calculated to evaluate the cytotoxicity of each natural
product. The concentration of sample required to inhibit
50% of the cell proliferation (IC50) was calculated from a
calibration curve by a linear regression7 using Microsoft
Excel. Three independent experiments are carried out for
each sample.
Disulfenylation of 2
To a solution of 2 (1 mg) dissolved in toluene (2 mL)
were added 5 mg of FeCl3 and 2 mL of dimethyl disulfide;
the reaction mixture was stirred at room temperature
and monitored by TLC. After 24 h, the medium was
concentrated under reduced pressure and the residue was
treated with a saturated aqueous solution of NaHCO3 and
extracted with EA. The colorless amorphous solid 2b
obtained was analyzed by EI-MS.
Results and Discussion
The crude organic extract was subjected to repeated
columns chromatography yielding two new ceramides (1, 2)
together with twenty one known compounds namely lanosta-
7,24-dien-3-one(3),8 lanosta-8,24-dien-3-one(4),8 β-amyrine
(5),9 lupeol (6),9 6-prenylpinocembrin (7),10 bergapten (8),11
chiricanine A (9),12 genistein (10),13 wighteone (11),13
6-prenylapigenin (12),14 3,4-dihydroxybenzoic acid (13),15
Cytotoxicity assays
The cytotoxicity of the compounds was evaluated
using MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-

Vol. 23, No. 3, 2012
Nana et al.
485
2,4,5-trihydroxybenzoic acid (14),16 alpinumisoflavone
(15),17 4’-O-methylalpinumisoflavone (16),13 luteolin (17),18
catechine (18),19 β-sitosterol-3-O-(6’-O-heptadecanoyl)-β-
D-glucopyranosyl (19),20 polystachyol (20),21 lyoniresinol-
2a-O-β-D-xylopyranoside (21),21 β-sitosterol-3-O-β-D-
glucopyranoside (22),22 and dongnoside E (23).23
methanolysis product of 1, which displayed a molecular
ion at m/z 424 [C27H52O3]+.. The position D7’ of this double
bond was assigned from its oxidative cleavage (1a) which
formed a fragment with a pseudo-molecular ion at m/z 448
[M+H]+ (Scheme 1). NOESY correlations and comparison
of 1H and 13C NMR data with those of the literature allowed
to deduce the relative and absolute configuration at C-2,
C-3, C-4, and C-2’to be (S), (S), (R), and (R) respectively.24
The foregoing data led to identify 1 as (2R,7E)-2-hydroxy-
N-[(2S,3S,4R)-1,3,4-trihydroxyhexadecan-2-yl]hexacos-7-
enamide, trivially named glumoamide.
Compound 2 was isolated as a white solid. Its molecular
formula C48H93NO10 was determined on the basis of HR-
ESI-MS which displayed a pseudo-molecular ion peak
at m/z 844.6897 [M+H]+, and the NMR data (Table 1)
accounting for three double bond equivalents. The presence
of OH and NH functions with absorption bands on the IR
spectrum at 3402, 1620 and 1544 cm-1 was characteristic
of cerebrosides.25
This compound gave a positive test to Molish reagent
indicative of glycosides. The NMR spectra of 2 presented
similar signals to those of 1, with additional shifted
resonances at dH/dC 4.22 (d, 7.6)/102.9, 3.21 (br d, 7.2)/73.2,
3.36 (t, 8.0)/76.1, 3.36 (t, 8.0)/69.5, 3.22 (br s)/76.0,
3.69 (m), and 3.78 (br d, 11.2)/61.1 characteristic of a
β-D-glucopyranosyl moiety.25 Methanolysis of 2 led to a
saturated fatty acid methyl ester (2a) identified by the EI-MS
molecular ion at m/z 426 ([C27H54O3]+.). The position of the
double bond observed on the NMR spectra at dH/dC 5.27
(2H, br s)/129.2, 130.1 was determined to be D10 from the
ESI-MS of the sulfenylated derivative (2b), which exhibited
a pseudo-molecular ion at m/z 145 (Scheme 2). The olefin
cis-geometry was assigned on the basis of the carbon
chemical shifts of allylic methylene groups at dC 27.0 and
27.1 which are around 33 ppm in the trans configuration.25
Further correlation between the anomeric proton at dH 4.22
and the carbon at dC 68.6 allowed to connect the sugar
moiety at C-1. The relative configuration was deduced by
NOESY correlations and the absolute configuration at C-2,
Compound 1was obtained as a white powder. Its positive
mode HR-ESI-MS spectrum gave a pseudo-molecular ion
at m/z 682.6319 (calc. 682.6344) corresponding to the
molecular formula [C42H84O5N+H]+ accounting for 2 double
bond equivalents. The IR spectrum exhibited characteristic
absorption bands for free OH group (3330 cm-1), olefinic
function (1649 cm-1) and secondary amide (3203, 1620
and 1544 cm-1). The 1H and 13C NMR spectra (Table 1) of
1 displayed a triplet of 6H at dH/dC 0.82, (t, 6.3 Hz)/14.0
assigned to the two terminal CH3 groups, a broad singlet
at dH/dC 1.10-1.30/(29.3-29.6) corresponding to a sequence
of CH2 groups, an exchangeable nitrogen-attached proton
appearing as doublet at dH 7.38 (J 8.7 Hz) and a proton
geminated to the amide at dH/dC 4.03 (m)/51.8. Furthermore,
an oxymethylene group was observed at dH/dC 3.66 (dd,
4.8, 11.4), and 3.75 (dd, 4.2, 11.7)/61.3, along with three
oxymethine groups at dH/dC 3.44 (br s) 75.8,3.47 (br s)/72.4,
and 3.98 (dd, 3.6, 8.4)/72.0, and a carbonyl at dC 175.5
suggesting a phytoceramide structure.24 The ceramide core
was confirmed by long-range correlations exhibited on the
HMBC spectrum between the proton at dH 7.38 and the
carbonyl at dC 175.5. Moreover, the proton of oxymethine
group at dH 3.47 (H-4) correlated with the carbons at dC
61.3 (C-1), 51.8 (C-2), and 75.8 (C-3) which matched
with a trihydroxylamine-sphingosine in the phytoceramide
skeleton. The sphingosine was attached to a α-hydroxyfatty
acyl by an amide function since both protons at dH 4.03
(H-2) and 3.98 (H-2’) showed correlations with the
carbonyl at dC 175.5.
The resonances of two overlapped olefin protons in
trans-geometry21 were further observed at dH/dC 5.34
(br s)/129.7 and 5.34 (br s)/130.8 and located in the fatty
acid chain, as deduced from the mass spectrum of the
OH
1
3
OH
O
4
16
a. (CH3CO)2O/C5H5N
b. KMnO4/NaIO4 in THF-H2O (9:1)
HN
OH
1a
1'
OH
m/z 448
Compound 1
HO
3'
c. MeONa - MeOH
O
+
O
HO
Scheme 1. Oxidative cleavage of 1.

486
Ceramides and Cytotoxic Constituents from Ficus glumosa Del. (Moraceae)
J. Braz. Chem. Soc.
Table 1. 1H NMR (300 MHz) and 13C NMR (75 MHz) spectral data of 1 and 2 (CDCl3+CD3OD; d in ppm, J in Hz)
Compound 1
dH
Compound 2
Position
dC
-
Position
dH
dC
-
NH
1
7.38 (d, 8.7)
NH
1
7.53 (d, 8.8)
3.66 (dd, 4.8, 11.4, Ha)
3.75 (br d, 11.2, Hb)
61.3
3.73.(m)
4.01 (dd, 5.2, 11.4)
68.6
2
4.03 (m)
3.44 (br s)
51.8
75.8
2
4.14 (br d, 3.6)
3.52 (t, 10.4)
3.46 (br d, 10.3)
1.10-1.30 (br s)
1.10-1.30 (br s)
1.10-1.30 (br s)
1.98 (m)
50.0
74.1
3
3
4
3.47 (br s)
72.4
4
72.0
5
1.13 (m, Ha), 1.51 (m, Hb)
1.10-1.30 (br s)
1.10-1.30 (br s)
1.10-1.30 (br s)
1.10-1.30 (br s)
0.82 (t, 6.3)
33.1
5
32.5
6
25.7
6
25.9
7-13, 10′-23′
29.3-29.6
32.5
7-8, 13-14, 5′-22′
29.2-29.6
27.0, 27.1
129.2
130.1
31.8, 32.0
22.5
14, 24′
9, 12
15, 25′
22.6
10
5.27 (br s)
16, 26′ (CH3)
14.0
11
5.27 (br s)
1′ (C=O)
-
175.5
72.0
15, 23′
1.10-1.30 (br s)
1.10-1.30 (br s)
0.80 (t, 6.4)
2′
3.98 (dd, 3.6, 8.4)
1.50 (m, Ha), 1.73 (m, Hb)
1.35 (m)
16, 24′
3′
34.4
17, 25′ (CH3)
13.9
4′, 5′
6′
25.2
1′ (C=O)
-
175.6
72.0
1.61 (m, Ha), 1.94 (m, Hb)
5.34 (br s)
32.7
2′
3.96 (dd, 3.6, 8.0)
1.10-1.30 (br s)
1.10-1.30 (br s)
7′
129.7
130.8
32.5
3′
34.2
8′
5.34 (br s)
4′
25.2
9′
1.33 (m, Ha), 1.87 (m, Hb)
Glucosyl
1″
2″
3″
4″
5″
6″
4.22 (d, 7.6)
3.21 (br d, 7.2)
3.36 (t, 8.0)
102.9
73.2
76.1
69.5
76.0
61.1
3.36 (t, 8.0)
3.22 (br s)
3.69 (m), 3.78 (br d, 11.2)
2'
1
HO
O
C23H47
m/z 145
OH
6''
FeCl3, Me2S2
S
NH OH
Compound 2
O
HO
HO
Toluene, rt
S
O
1''
3''
5
OH
OH
17
2b
Scheme 2. Determination of double bond location by disulfenylation and MS analysis.
C-3, C-4, and C-2’ was determined as being (S), (S), (R),
and (R) according to the 1H and 13C NMR data compared
with those of the literature.24, 25 The above mentioned data
led to characterize 2 as (2R)-N-{(2S,3S,4R,9Z)-1-O-[(β-
D-glucopyranosyl]-3,4-dihydroxyheptadec-9-en-2-yl}-
2-hydroxypentacosanamide, trivially named glumoside.
The structures of known compounds were identified by
using their NMR data and by comparison of those reported
in the literature.
a significant antiproliferative activity with an IC50 of
0.75 µmol L-1, while the value obtained with the reference
drug doxorubicin was 0.91 µmol L-1. In contrast,
lanosta-7,24-dien-3-one (3), β-amyrine (5), lupeol (6),
6-prenylapigenin (12) and luteolin (17) showed moderated
activities, whereas other compounds were not active.
Compound 23 was further tested against fibrosarcoma
cancer HT1080 cells lines and presented an interesting
antiproliferative cells growth with 0.7 µmol L-1 as IC50
after 48 h. This natural product was more active than the
reference drug etoposide which showed an IC50 1 µmol L-1.
Some of compounds were tested against the prostate
cancer PC-3 cells (Table 2). Dongnoside E (23) showed

Vol. 23, No. 3, 2012
Nana et al.
487
Table 2. Cytotoxicity of isolated compounds and doxorubicin against
prostate cancer PC-3 cell line
2. Koné, W. M.; Atindehou, K. K.; S. Afr. J. Bot. 2008, 74, 76.
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Compound
IC50 / (µmol L-1)
1
2
> 30
> 30
4. Madubunyi, I. I.; Onoja, S. O.;Asuzu, I. U.; Comp. Clin. Pathol.
2010, DOI 10.1007/s00580-010-1103-5.
3
4
28.53 0.16
> 30
5. Forguson, L. R.; Mutat. Res. 1994, 307, 395.
6. Bras, M.; Queenan, B.; Susin, S. A.; Biochemistry (Moscow)
2005, 70, 231.
5
6
7
19.86 0.22
21.58 0.35
> 30
7. Joshi, S. C.;Verma, A. R.; Mathela, C. S.; Food Chem. Toxicol.
2010, 48, 37.
8
9
11
12
> 30
> 30
> 30
8. Mendes, C. C.; Sandes, L. Q.; Cruz, F. G.; Roque, N. F.; Chem.
Biodivers. 2009, 6, 1463.
25.06 0.01
> 30
13
9. Mahato, S. B.; Kundu, A. P.; Phytochemistry 1994, 37, 1517.
10. Caffaratti, M.; Ortega, M. G.; Scarafia, M. E.; Espinar, L. A.;
Juliani, H. R.; Phytochemistry 1994, 36, 1083.
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Prod. 2001, 64, 710.
14
15
16
17
18
19
20
23
> 30
> 30
> 30
28.10 0.28
> 30
> 30
> 30
0.75 0.06
0.91 0.12
Doxorubicin
13. Lane, G. A.; Newman, R. H.; Phytochemistry 1987, 26, 295.
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Conclusions
15. Zhu, C.-C.; Wang, K.-J.; Wang, Z.-Y.; Li, N.; Bull. Korean
Chem. Soc. 2010, 31, 224.
The higher concentration of flavonoids, benzoic acid
derivatives, saponine, steroids and triterpenes highlights
the use of this plant in traditional remedy against lung
diseases, since several compounds belonging to the above-
mentioned classes are present in plants having antitussive
and expectorant activities.26 Besides, some polyphenols
are active against viral respiratory infections, bacteria and
fungi.27 The foregoing results clearly indicated that Ficus
glumosa is a promising source of drug development, and
23 can be a potential antitumour lead.
16. Saito, S.; Kawabata, J.; Helv. Chim. Acta 2009, 89, 1395.
17. El-Masry, S.;Amer, M. E.;Abdel-Kader, M. S.; Zaatout, H. H.;
Phytochemistry 2002, 60, 783.
18. Peng, W.; Han, T.; Wang, Y.; Xin, W.-B.; Zheng, C.-J.; Qin,
L.-P.; Chem. Nat. Compd. 2011, 46, 959.
19. Nechepurenko, I. V.; Polovinka, M. P.; Komarova, N. I.;
Korchagina, D. V.; Salakhutdinov, N. F.; Nechepurenko, S. B.;
Chem. Nat. Compd. 2008, 44, 31.
20. Chen, L.; Wang, J.-J.; Zhang, G.-G.; Song, H.-T.; Qin, L.-P.;
Nat. Prod. Res. 2009, 23, 1330.
Acknowledgments
21. Sadhu, S. K.; Choudhuri, P. P. M. S. K.; Ishibashi, T. O. M.;
J. Nat. Med. 2006, 60, 258.
The authors thank T. W.A. S. (TheAcademy of Sciences
for the Developing World) for the fellowship providing to
Frederic Nana.
22. Bayoumi, S.A. L.; Rowan, M. G.; Beeching, J. R.;, Blagbrough,
I. S.; Phytochemistry 2010, 71, 598.
23. Ding,Y.; Chen,Y.-Y.;Wang, D.-Z.;Yang, C.-R.; Phytochemistry
1989, 28, 2787.
Supplementary Information
24. Wang, R.-F.; Liu, R.-N.; Zhang, T.; Wu, T.; Molecules 2010,
15, 7467.
Spectra (1D/2D NMR and MS) and NMR data
of compounds (1-23) are available free of charge at
http://jbcs.sbq.org.br as PDF file.
25. Liu, A.; Zou, Z.-M.; Xu, L.-Z.;Yang, S.-L.; J. Asian Nat. Prod.
Res. 2005, 7, 861.
26. Gairola, S.; Gupta, V.; Bansal, P.; Singh, R.; Maithani, M.; Int.
J. Pharm. Sci. Rev. Res. 2010, 5, 5.
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Submitted: September 7, 2011
Published online: January 24, 2012