Assessing Chemical Constituents of Mimosa caesalpiniifolia Stem Bark: Possible Bioactive Components Accountable for the Cytotoxic Effect of M. caesalpiniifolia on Human Tumour Cell Lines
Abstract
:1. Introduction
2. Results and Discussion
2.1. Phytochemical Analysis
2.1.1. Non-Polar Compounds and Acid Derivatives of M. caesalpiniifolia by GC-qMS
Chemical Constituents | Molecular Formula | EIMS [M+•] | Rt (min) | HEX (%) | DCM (%) | ||
---|---|---|---|---|---|---|---|
1 | Methyl hexadecanoate C16:0 | C17H34O2 | 270 | 20.16 | 6.05 | 0.33 | |
2 | Ethyl hexadecanoate C16:0 | C18H36O2 | 284 | 22.23 | 2.43 | ||
3 | Methyl heptadecanoate C17:0 | C18H36O2 | 284 | 23.14 | 0.34 | ||
4 | Methyl (9Z,12Z) octadeca-9,12-dienoate C18:2 | C19H34O2 | 294 | 24.98 | 8.05 | 0.32 | |
5 | Methyl (9Z)-octadec-9-enoate C18:1 | C19H36O2 | 296 | 25.15 | 5.13 | 0.13 | |
6 | Methyl (11Z)-octadec-11-enoate C18:1 | C19H36O2 | 296 | 25.27 | 0.62 | ||
7 | Methyl octadecanoate C18:0 | C19H38O2 | 298 | 25.84 | 1.73 | ||
8 | Ethyl (9Z,12Z)-octadeca-9,12-dienoate C18:2 | C20H36O2 | 308 | 26.63 | 2.04 | ||
9 | Ethyl (9Z)-octadec-9-enoate C18:1 | C20H38O2 | 310 | 26.78 | 1.21 | ||
10 | Ethyl(11Z)-octadec-11-enoate C18:1 | C20H38O2 | 310 | 26.94 | 0.44 | ||
53 | Unidentified | 26.97 | 2.17 | ||||
11 | Ethyl octadecanoate C18:0 | C20H40O2 | 312 | 27.46 | 0.53 | ||
12 | Methyl (10Z,13Z)-nonadeca-10,13-dienoate C19:2 | C20H36O2 | 308 | 27.92 | 0.08 | ||
13 | Methyl nonadecanoate C19:0 | C20H40O2 | 312 | 28.23 | 0.17 | ||
14 | Methyl eicosanoate C20:0 | C21H42O2 | 326 | 30.49 | 0.75 | ||
15 | Ethyl eicosanoate C20:0 | C22H44O2 | 340 | 31.89 | 0.14 | ||
16 | Methyl heneicosanoate C21:0 | C22H44O2 | 340 | 32.56 | 1.14 | ||
54 | Unidentified | 32.62 | 1.32 | ||||
17 | Methyl docosanoate C22:0 | C23H46O2 | 354 | 34.63 | 3.85 | ||
55 | Unidentified | 34.64 | 1.76 | ||||
18 | Ethyl docosanoate C22:0 | C24H48O2 | 368 | 35.84 | 0.84 | ||
19 | Methyl tricosanoate C23:0 | C24H48O2 | 368 | 36.49 | 0.49 | ||
56 | Unidentified | 36.56 | 0.79 | ||||
57 | Unidentified | 36.87 | 0.76 | ||||
20 | Methyl tetracosanoate C24:0 | C25H50O2 | 382 | 38.36 | 4.95 | 2.16 | |
58 | Unidentified | 38.78 | 1.21 | ||||
21 | Ethyl tetracosanoate C24:0 | C26H52O2 | 396 | 39.45 | 1.29 | ||
22 | Methyl pentacosanoate C25:0 | C26H52O2 | 396 | 40.06 | 0.49 | ||
59 | Unidentified | 40.62 | 1.73 | ||||
23 | Ethyl pentacosanoate C25:0 | C27H54O2 | 410 | 41.14 | 0.1 | ||
24 | Methyl hexacosanoate C26:0 | C27H54O2 | 410 | 41.78 | 3.29 | 3.08 | |
25 | Ethyl hexacosanoate C26:0 | C28H58O2 | 424 | 42.78 | 0.74 | ||
26 | Stigmastatriene | C29H46 | 394 | 43.13 | 0.04 | ||
27 | Methyl heptacosanoate C27:0 | C28H56O2 | 424 | 43.37 | 0.22 | ||
60 | Unidentified | 43.93 | 2.82 | ||||
28 | Stigmastadiene | C29H48 | 396 | 44.10 | 0.06 | ||
29 | α-Tocopherol (vitamin E) | C29H50O2 | 430 | 44.83 | 0.02 | ||
30 | Methyl octacosanoate C28:0 | C29H58O2 | 438 | 44.99 | 1.88 | 3.19 | |
31 | Ethyl octacosanoate C28:0 | C30H60O2 | 452 | 45.95 | 0.36 | ||
32 | Campesterol | C28H48O | 400 | 46.36 | 1.67 | ||
33 | Campestanol | C28H50O | 402 | 46.52 | 0.07 | ||
34 | Stigmasterol | C29H48O | 412 | 46.81 | 4.75 | ||
61 | Unidentified | 47.01 | 3.47 | ||||
35 | Sitosterol | C29H50O | 414 | 47.76 | 2.97 | ||
36 | β-Amyrenone | C30H48O | 424 | 47.81 | 0.4 | ||
37 | β-Amyrin | C30H50O | 426 | 48.36 | 1.05 | ||
38 | Campestenone | C28H46O | 398 | 48.41 | 0.87 | ||
39 | Lupenone | C30H48O | 424 | 48.74 | 5.35 | ||
40 | Stigmasta-4,22-dien-3-one | C29H46O | 410 | 48.97 | 2.47 | ||
41 | Lupeol | C30H50O | 426 | 49.42 | 14.7 | 3.26 | |
42 | Sitostenone | C29H48O | 412 | 50.01 | 2.74 | ||
43 | 3-Oxo-olean-18-en-28-oic acid methyl ester | C31H48O3 | 468 | 50.75 | 0.56 | ||
44 | 3-Oxo-olean-12-en-28-oic acid methyl ester | C31H48O3 | 468 | 51.54 | 0.26 | ||
45 | 3-Oxo-lup-20(29)-en-28-oic acid methyl ester | C31H48O3 | 468 | 51.91 | 1.20 | ||
46 | 3β-Hydroxy-lup-20(29)-en-28-oic acid methyl ester | C31H50O3 | 470 | 52.81 | 4.25 | 70.3 | |
47 | 3-Oxo-urs-12-en-28-oic acid methyl ester | C31H48O3 | 468 | 53.05 | 0.24 | ||
48 | 3β-Acetoxy-olean-18-en-28-oic acid methyl ester | C33H52O4 | 512 | 53.49 | 2.76 | ||
49 | Stigmastane-3,6-dione | C29H48O2 | 428 | 53.62 | 0.36 | ||
50 | 3β-Acetoxy-olean-12-en-28-oic acid methyl ester | C33H52O4 | 512 | 54.43 | 0.71 | ||
51 | 3β-Acetoxy-lup-20(29)-en-28-oic acid methyl ester | C33H52O4 | 512 | 54.80 | 0.99 | ||
52 | 3β-Acetoxy-urs-12-en-28-oic acid methyl ester | C33H52O4 | 512 | 56.16 | 2.20 | 1.24 |
2.1.2. Total Phenolic and Flavonoid Contents of M. caesalpiniifolia Stem Bark
Samples | TPC mg GAE/g DPM | TFC mg RE/g DPM |
---|---|---|
Ethanolic extract | 14.80 ± 0.30 | 1.81 ± 0.14 |
Hexane fraction | 0.16 ± 0.02 | - |
Dichloromethane fraction | 0.56 ± 0.01 | 0.35 ± 0.01 |
Ethyl acetate fraction | 3.17 ± 0.04 | 0.34 ± 0.02 |
Aqueous fraction | 6.42 ± 0.09 | 0.68 ± 0.03 |
2.1.3. Identification of Phenolic Compounds in M. caesalpiniifolia by ESI(−)-LTQ-Orbitrap-MS
2.2. Cytotoxic Activity
3. Experimental Section
3.1. General
3.2. Plant Material
3.3. Extraction and Isolation of Chemical Constituents
3.4. Analysis of Non-Polar Fractions of M. caesalpiniifolia by Gas Chromatography-Quadrupole Mass Spectrometry (GC-qMS)
3.5. Determination and Identification of Polyphenols
3.5.1. Total Phenol Content
3.5.2. Total Flavonoid Content
3.5.3. Direct Infusion Mass Spectrometry Analysis of Ethanolic Extract of M. caesalpiniifolia Stem Bark by ESI(−)-LTQ-Orbitrap-MS
3.6. Cytotoxicity Assay
3.6.1. Cell Culture
3.6.2. Evaluation of Cell Proliferation by MTT Assay
3.7. Statistical Analysis
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Monção, N.B.N.; Araújo, B.Q.; Silva, J.D.N.; Lima, D.J.B.; Ferreira, P.M.P.; Airoldi, F.P.d.S.; Pessoa, C.; Citó, A.M.d.G.L. Assessing Chemical Constituents of Mimosa caesalpiniifolia Stem Bark: Possible Bioactive Components Accountable for the Cytotoxic Effect of M. caesalpiniifolia on Human Tumour Cell Lines. Molecules 2015, 20, 4204-4224. https://doi.org/10.3390/molecules20034204
Monção NBN, Araújo BQ, Silva JDN, Lima DJB, Ferreira PMP, Airoldi FPdS, Pessoa C, Citó AMdGL. Assessing Chemical Constituents of Mimosa caesalpiniifolia Stem Bark: Possible Bioactive Components Accountable for the Cytotoxic Effect of M. caesalpiniifolia on Human Tumour Cell Lines. Molecules. 2015; 20(3):4204-4224. https://doi.org/10.3390/molecules20034204
Chicago/Turabian StyleMonção, Nayana Bruna Nery, Bruno Quirino Araújo, Jurandy Do Nascimento Silva, Daisy Jereissati Barbosa Lima, Paulo Michel Pinheiro Ferreira, Flavia Pereira da Silva Airoldi, Cláudia Pessoa, and Antonia Maria das Graças Lopes Citó. 2015. "Assessing Chemical Constituents of Mimosa caesalpiniifolia Stem Bark: Possible Bioactive Components Accountable for the Cytotoxic Effect of M. caesalpiniifolia on Human Tumour Cell Lines" Molecules 20, no. 3: 4204-4224. https://doi.org/10.3390/molecules20034204