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2/8/2017 Journal of Chemical and Pharmaceutical Research | Synthesis pterocarpan compounds from Erythrina crista-galli L and their action towards …
Journal of Chemical and Pharmaceutical Research (ISSN : 0975-7384) Search results for Synthesis pterocarpan compounds from Erythrina crista-galli L and their action towards Plasmodium falciparumRelevant Articles [1]
Author(s): Tjitjik Sri Tjahjandarie, Ratih Dewi Saputri and Mulyadi Tanjung Synthesis of the naturally occurred 3-acetyl sandwicensin(2) and 2,7- dibromosandwicensin(3)was carried out by acetylation and bromination reaction, respectively. The pterocarpan synthesized in this ..
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Available online www.jocpr.com Journal of Chemical and Pharmaceutical Research, 2015, 7(1):666-670
ISSN : 0975-7384 Research Article CODEN(USA) : JCPRC5 Synthesis pterocarpan compounds from Erythrina crista-galli L and their action towards Plasmodium falciparum * Tjitjik Sri Tjahjandarie , Ratih Dewi Saputri and Mulyadi Tanjung Natural Products Chemistry Research Group, Organic Chemistry Division, Department of Chemistry, Faculty of Science and Technology, Universitas Airlangga, Surabaya, Indonesia
_____________________________________________________________________________________________ ABSTRACT Synthesis of the naturally occurred 3-acetyl sandwicensin(2) and 2,7- dibromosandwicensin(3)was carried out by acetylation and bromination reaction, respectively. The pterocarpan synthesized in this study was andwicensin(1) isolated from stem bark of Erythrina crista galli L. Their structures were established on the basis of spectroscopic evidence. Compounds 1–3 were evaluated for their antimalarial properties against Plasmodium palcifarum, showing their IC were 1.83, 34.81 and 12.9 µg/mL, respectively. 50 Keywords: 3-acetyl sandwicensin, 2,7-dibromosandwicensin, acetylation reaction, bromination reaction, antimalarial activity.
_____________________________________________________________________________________________
INTRODUCTION Malaria remains world one of the most devastating human parasitic infection affecting more than 500 million people and causing about 1-3 million deaths each year [1]. Plasmodium is transmitted by anopheline mosquitoues and undergoes a complex sexual developmental cycle in the insect host. Recently, chloroquine and artemisinin have used as antimalarial drug and show resistance against Plasmodium parasites in Indonesia. Erythrina belongs to the family of Leguminosae and Erythrina crista galli L is one species of Erythrina. This plant has been shown to produce a number of pterocarpan and alkaloid compounds that showed activity as anticancer, antioxidant, and antimalarial. Sandwicensin is a mayor compound which has been isolated from Erythrina crista galliand its activity as antimalarial [2]. In continuation of these chemical investigations, we will continue research to synthesize mayor compounds that is sandwicensin with acetylation and bromination method. This paper discusses the structure elucidation of the two compounds synthesized from the reaction of acetylation and bromination and their antimalarial activity.
EXPERIMENTAL SECTION
Synthesis of pterocarpan derived from sandwicensin compounds produced from stem bark of Erythrina crista galli was carried out by acetylation and bromination reaction, respectively. In the acetylation synthetic route, 3 mg sandwicensin compound is added to 0.2 ml of pyridine with the addition of 0.2 ml of anhydride acetate. It was cooled to room temperature and poured over crushed ice. The separated solid was filtered, washed with distilled water, dried and it was crystallized with ether-methanol to form a 3-acetyl sandwicensin [3]. Bromination synthetic route, in the fume hood, 0.1 g or 0.2 ml of sandwicensin compound is added to 2 ml of carbon tetrachloride and 5%
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Tjitjik Sri Tjahjandarie et al J. Chem. Pharm. Res., 2015, 7(1):666-670
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solution of bromine in carbon tetrachloride is added drop wise, with shaking, and reflux for 5h until the bromine
color persist and to form 2,7- dibromosandwicensin [4].4 AcO O
4 HO O 4a
6 4a
6 H 11b
H 6a
11b 6a 11a 6b
1 11a 6b H
1 10a H
(i)
9 O 10a
9 O
OCH 3
(ii)
OCH 3 , ,
2
2 , , , ,
4
5
4
5 Figure-1.Preparation of compound 3-acetyl sandwicensin (2),colorless solid :(i) pyridine,anhydride acetate,temperature o
37 C; (ii) crystallized eter-metanol 4 4 O
HO HO O 4a 6 4a 6 Br H 11b 6a H 11b 6a 1 11a 6b Br 1 11a 6b H H 10a 9 10a 9 O O (i)
OCH 4 , , 2 , OCH 5 3 (ii) 4 , , 2 , 5 3 Sandwicensin 2,7-Dibromo sandwicensin
Figure-2. Preparation of compound 2,7-dibromo sandwicensin (3), yellow solid: (i) CCl , 5% Br in CCl ;
4 2 4 (ii) reflux 5h, bromine color persist- + Sandwicensin(1), yellow solid,1H NMR (500 MHz, CDCl 3 ) data, see Table-1; UV (MeOH) λmax nm (log ɛ) : 223
(4.60), 285 (3.84), and 287 nm (3.89).HR-ESI-mass spectra (m/z 339.1642 [M+H] , calcd. for C H O 325.1440).
21 23 4,
3-Acetyl sandwicensin(2), colourless solid, 1H-NMR (500 MHz,CDCl ) data, see Table-1;UV (MeOH) λmax nm
3 (log ɛ) : 285 (3.90), and 289 nm (4,10).2,7-Dibromo sandwicensin(3) ,yellow solid,1H-NMR (500 MHz, CDCl 3 ) data, see Table-1;UV (MeOH) λmax nm (log ɛ) : 229 (4.13), 286 (3.84), and 289 nm (3.86).
Antimalarial properties ofcompound1-3 against Plasmodium palcifarum were obtained from the Institute of Tropical
Diseases, Universitas Airlangga, Surabaya, Indonesia. In vitro antimalarial activity against Plasmodium palcifarum
was carried out according to a modified method of Trager and Jensen using RPMI 1640medium with10% O+ serum
[5]. The antimalarial activity of three phenolic compounds and chloroquine (positive control) were measured in
triplicate. Fresh red blood cells were used as a negative control. The active compound was dissolved in DMSO and
diluted with RPMI 1640 medium to prepare a series of concentration. Parasitaemia was evaluated after 48 by
Giemsa stain and the average percentage suppression of parasitaemia was calculated by following equation [6,7]: 100 × % − %% = %
The influence of the active compound on the growth of parasites were expressed by the 50% inhibitory
concentrations (IC ) which were determined using linier regression analysis. 50
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Tjitjik Sri Tjahjandarie et al J. Chem. Pharm. Res., 2015, 7(1):666-670
______________________________________________________________________________
RESULTS AND DISCUSSION
Sandwicensin is a mayor compound produced from stem bark Erythrina crista galli L [8]. Sandwicensin (1)was
+isolated as a yellow solid, and its UV spectrum exhibited absorption maxima (nm) (log ε): 223 (4.60), 285
λ maks
(3.84), and287 nm (3.89) a typical for a pterocarpan. From HR-ESI-mass spectra (m/z 339.1642 [M+H] , calcd. for
1 13 C H O 325.1440).The H and C NMR can be seen in Table 1. There is one methoxyl groups attached to the 21 23 4,aromatic ring from compound 1 that showed proton signal at δ 3.81 and the carbon signal at 55.9.The placement of
Ha methoxy group in the C-3or C-9 confirmed by the HMQC and HMBC spectra. The HMBC spectrum shows a
correlation between the proton signal at δ 3.81with carbonoxyaril signal at 155.8. Furthermore, the correlation
H δ Cbetween aromatic proton signals at δ 7.02 (d, 8.1, H-7)with oxyaril carbon signal at 155.8 indicated that the
H δ C methoxyl group attached at C-9.HO O
H
H O OCH3 Figure 3.The significant HMBC correlations of 1
3-Acetyl sandwicensin(2) produced from synthesis sandwicensin (1) using acetylation methods. 3-Acetyl
sandwicensin obtained as colourless solid, its UV spectrum exhibited absorption maxima (nm) (log ε): 223
λ maks (4.60), 285 (3.84), and287 nm (3.89). 1 Based on H-NMR proton spectrum showed four proton signal at 5.46 (1H, d, J = 6.7 Hz); 4.25 (1H, t, J = 10.8 δ H 1 Hz; 3.64 (1H, dd, J = 10.8 Hz); and 3.54 (1H, m)which is typical for pterocarpan structure. H-NMR spectrum of
compound 1 shows two signals of aromatic unit, there are a pair of doublet signals ortho (J = 8.1 Hz) at 7.01 dan
δ H
6.40 and the presence of three other aromatic proton signals with ABX system at 7.54 (1H, d, J = 8.4 Hz); 6.78
δ H
(1H, dd, J = 8.4 and 2.4 Hz); and6.68 ppm (1H, d, J = 2.4 Hz). The presence of the methyl group 1.56 at C-3
δ H shows that acetyl bond to sandwicensin skeleton and compound 2 was identified 3-acetyl sandwicensin.
2,7-Dibromo sandwicensin(3) produced from synthesis sandwicensin (1)using bromination methods. 2,7-Dibromo
sandwicensin isolated as yellow solid, its UV spectrum exhibited absorption maxima λ maks (nm) (log ε): 229 (4.13),
1 1 13286 (3.84), and 289 nm (3.86). Based on H-NMR spectral data of compounds 3 shows similar pattern of the H and
C chemical shifts of NMR with compound 2. The difference with compound 3 is the addition of two bromide
groups. Two proton singlets at 7.59(1H, H-1) and 6.25 (1H, H-4) showed the presence of four substituents
δ H
attached to the ring A and also shows that the presence of bromide group attached to the C-2. The presence of one
proton singlets 7.31 at H-8 and methoxy group at C-9 showed that the bromide group in the position at C-7. Based
δ H on 1D NMR data, compound 3 was identified 2,7-dibromo sandwicensin.
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Tjitjik Sri Tjahjandarie et al J. Chem. Pharm. Res., 2015, 7(1):666-670
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4 4a 6 6a
5 , 2,7-dibromo sandwicensin
4 ,
2 ,
11b
9 6b 10a 11a
4 4a 6 6a
1
3 H H
O HO O OCH
5 , 3-acetyl sandwicensin
4 ,
2 ,
11b
9 6b 10a 11a
1
669
Figure 4.Synthesis of pterocarpan derived from sandwicensin
Table 1. NMR spectroscopic data of sandwicensin(1), 3-acetyl sandwicensin (2), and 2,7-dibromo sandwicensin(3) in CDCl
3 No.H δ H (mult, J Hz) Sandwicensin (1) δH (mult, J Hz)
3 H H
O AcO O OCH
Compound 1 isolated from the stem bark of E.crista-galli and synthesis compound 2-3 was assessed for their
antimalarial activity against Plasmodium falciparum. The results are presented in Table-3.Compounds 1–3 were
evaluated for their antimalarial properties against Plasmodium palcifarum, showing their IC 50 were 1.83, 34.81, and 12.9 µg/mL, respectively (chloroquine as a positive control, IC 50 1.02 µg/mL). These antimalarial data suggested that the compound 1-3 showed activity against Plasmodium palcifarum.9-OCH 3 3.81 (s) 3.78 (s) 3.83 (s) 3-CH 3 - 1.56 (s) -
11b - - - 1’ 3.31 (d, 7.9) 3.26 (d, 6.4) 3.31 (d;8.6) 2’ 5.26 (t, 7.2) 5.21 (t, 8.3) 5.54 (d;6.9) 3’ - - - 4’ 1.78 (s) 1.74 (s) 1.57 (s) 5’ 1.67 (s) 1.64 (s) 1.41 (s)
10a - - - 11a 5.46 (d, 6.8) 5.46 (d, 6.7) 5.48(d; 7.4)
8 6.42 (d,8.1) 6.40 (d,8.1) 7.31 (s) 9 - - - 10 - - -
3.26 (dd,8) 6a 3.52 (m) 3.54 (m) 3.53 (m) 6b - - - 7 7.02 (d, 8.1) 7.01 (d, 8.1) -
3.64 (dd,10.8) 4.48 (dd;8);
3.66 (dd,10.9; 5.1) 4.25 (t, 10.8);
6 4.23 (t, 10.9);
4a - - -
1 7.41 (d, 8.4) 7.54 (d, 8.4) 7.59 (s) 2 6.58 (dd, 8.4; 2.4) 6.78 (dd, 8.4; 2.4) - 3 - - - 4 6.44 (d, 2.4) 6.68 (d, 2.4) 6.05 (s)
3-Acetyl sandwicensin (2)
δ H (mult, J Hz) 2,7-Dibromo sandwicensin (3)Br Br
Tjitjik Sri Tjahjandarie et al J. Chem. Pharm. Res., 2015, 7(1):666-670
______________________________________________________________________________
13 Table 2. C-NMR spectroscopic data of sandwicensin(1), and 3-acetyl sandwicensin(2) in CDCl δ δ C C 3 No.C (Sandwicensin) (3-Acetyl sandwicensin)1 132.3 132,2 2 109.9 110.6 3 157.5 158.4 4 103.1 103.1
4a 156.5 156.4
6
66.4
66.6 6a
39.9
40.0 6b 119.4 119.0 7 122.3 122.2
8 103.5 103.0 9 155.8 156.3 10 112.6 111.2
10a 158.5 158.6 11a
78.0
77.8 11b 113.3 113.4
1’
22.9
22.8 2’ 121.6 121.7 3’ 132.2 132.0 4’
17.4
18.4 5’
25.8
26.3 9-OCH 3
55.9
56.0 3-CH - 3
21.3 Table 3. Antimalarial and DPPH scavenging assay of 1-3
Antimalarial Compound
IC 50 (µg/mL)
Sandwicensin
1.83 3-Acetyl sandwicensin
34.81 2,7-Dibromo sandwicensin
12.9 Chloroquine
1.02 CONCLUSION
In summary, 3-Acetyl sandwicensin(2) and 2,7-dibromo sandwicensin(3)can be performed by acetylation and
bromination of sandwicensin. Evaluation for their antimalarial properties against Plasmodium palcifarum, showing
their IC 50 were 34.81, and 12.9 µg/mL which activities are lower than sandwicensin with IC 50 of 1.83.Acknowledgements
This research was supported by Directorate of Higher Education, Ministry of Education and Culture, Republic of
Indonesia (AUPT Universitas Airlangga, 2014). We would like to thank to Mr. Ismail Rachman from the Herbarium
Bogoriense, Botanical Garden, Bogor, Indonesia for identifying the species.
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