Bis (Isothiocyanatomethyl) Benzene, A Plant Derived Anti-Neoplastic Compound: Purified from Moringa Oleifera Leaf Extract

Author(s): Samrat Paul , Piyali Basak* , Namrata Maity , Chayan Guha , Nandan Kumar Jana .

Journal Name: Anti-Cancer Agents in Medicinal Chemistry

Volume 19 , Issue 5 , 2019

Become EABM
Become Reviewer

Graphical Abstract:


Abstract:

Background: Moringa oleifera lam, commonly known as “Sajina”, is an indigenous species to India. In our folk medicine, it is used for the treatment of Canker (cancer). The Moringa oleifera leaf extract contains many phyto-compounds, with some being anti-neoplastic in nature.

Objective: Our preliminary study showed that the leaf extract significantly kills cancer cells compared to normal cells. On searching for the new phyto-compound, Bis-isothiocyanatomethyl) benzene was purified and isolated.

Methods: The sequential process of fractional distillation, column chromatography, followed by TLC and HPLC is performed for purification. Every fraction from each step was tested on HeLa cell line for evaluating the presence of the phyto-compound.

Results and Conclusion: FTIR peak analysis of a single phyto-compound shows the presence of thiocyanate group, aromatic carbon group. 1H & 13C NMR peak analysis along with High-resolution mass spectroscopy (HRMS) calculation confirm the chemical structure with IUPAC name [Bis (Isothiocyanatomethyl) benzene]. Previously, Isothiocyanatomethyl- benzene solely or in conjugation with sugar molecule has been reported, but its dimeric form in nature hasnot yet been published anywhere. It shows anticancer activity by retarding cancer cell growth & inhibits carcinogenesis on HeLa, MCF-7, and MDA-MB-231 cell lines by caspase 3 apoptotic pathway and showed comparatively less cytotoxicity to PBMC cell. It shows anticancer activity almost the same as the market available drug Cis-Platin. Therefore, further extrapolating its activity with different concentrations may result in its use as a drug formulation for the treatment of cancer.

Keywords: Moringa oleifera, purification, phyto-compound, chemical analysis, anti- neoplastic agent, HPLC, NMR, FTIR.

[1]
Cragg, G.M.; Newman, D.J. Plants as a source of anti-cancer agents. J. Ethnopharmacol., 2005, 22, 72-79.
[2]
Ramalingum, N.; Mahomoodally, M.F. The therapeutic potential of medicinal foods. Adv. Pharmacol. Sci., 2014, 2014354264
[3]
Rathi, B.; Bodhankar, S.; Deheti, A.M. Evaluation of aqueous leaves extract of M. oleifera lin for wound healing in albino rats. Indian J. Exp. Biol., 2006, 44, 898-901.
[4]
Bose, C.K. Possible role of Moringa oleifera lam. Root in epithelial ovarian cancer. MedGenMed, 2007, 9, 26.
[5]
Sreelatha, S.; Jeyachitra, A.; Padma, P.R. Antiproliferation and induction of apoptosis by Moringa oleifera leaf extract on human cancer cells. Food Chem. Toxicol., 2011, 49, 1270-1275.
[6]
Al-Asmari, A.H.; Albalawi, S.M.; Md Tanwir, A.; Khan, A.Q.; Al-Shahrani, M.; Islam, M. Moringa oleifera as an anti-cancer agent against breast and colorectal cancer cell lines. PLoS One, 2015, 10e0135814
[7]
Gopalakrishnanb, L.; Doriyaa, K.; Devarai, S.K. Moringa oleifera: A review on nutritive importance and its medicinal application. Food Sci. Hum. Wellness, 2016, 5, 49-56.
[8]
Hossain. 2012. Preparation of extract (Leaf & Bark) of Plant. Available at: http://forum.daffodilvarsity.edu.bd/index.php/topic, 9946.msg39456.html?PHPSESSID=j3lobms49vlgl3ppst1ob2fp82# msg 39456 Accessed: October 12, 2018.
[9]
Kuan-Hung, L.; Hao, Y.; Su-Yi, L.; Chi-Ming, Y.; Hsiang-Ju, T.; Jia-Jen, T.; Pi-Yu, C. Antioxidant activities of methanol extracts from selected taiwanese herbaceous plants. J. Food Nutr. Res., 2014, 2, 435-442.
[10]
Paini, W.; Tarsisius, D.W.B.; Fenny, A.K.; Evelyn, L.W. Difference of solvent polarity to phytochemical content and antioxidant activity of Pluchea Indicia less leaves extracts. Int. J. Pharmacog. Phytochem. Res, 2014, 6(4), 850-855.
[11]
Vijayalakshmi, M.; Periyanayagam, K.; Kavitha, K.; Akilandeshwari, K. Phytochemical analysis of ethanolic extract of Dichrostachys Cinerea W and Arn leaves by a thin layer chromatography, high performance thin layer chromatography and column chromatography. Anc. Sci. Life, 2013, 32, 227-233.
[12]
Sharma, V.; Paliwal, R. Isolation and characterization of saponins from moringa oleifera (moringaeceae) pods. Int. J. Pharma Sci., 2013, 5, 179-183.
[13]
Jorge, F.; Ferreira, S.; Gonzalez, J.M. Analysis of underivatized artemisinin and related sesquiterpene lactones by high-performance liquid chromatography with ultraviolet detection. Phytochem. Anal., 2009, 20, 91-97.
[14]
Burdall, S.E.; Hanby, A.M.; Lansdown, M.R.J.; Valerie, S. Breast cancer cell lines: Friend or foe? Breast Cancer Res., 2003, 5, 89-95.
[15]
Riss, T.L.; Moravec, R.A.; Niles, A.L.; Duellman, S.; Benink, H.A.; Worzella, T.J.; Minor, L. Cell viability assays.In: Assay Guidance Manual.[Internet]; Eli Lilly & Company and the National Center for Advancing Translational Sciences: USA, 2013, pp. 1-31.
[16]
Vijayarathna, S.; Sasidharan, S. Cytotoxicity of methanol extracts of Elaeis guineensis on MCF-7 and vero cell lines. Asian Pac. J. Trop. Biomed., 2012, 2(10), 826-829.
[17]
Eloff, N.J. Which extractant should be used for the screening and isolation of antimicrobial components from plants? J. Ethnopharmacol., 1998, 60, 1-8.
[18]
Sankhalkar, S.; Vernekar, V. Quantitative and qualitative analysis of phenolic and flavonoid content in Moringa oleifera Lam and Ocimum tenuiflorum L. Pharmacol. Res., 2016, 8(1), 16-21.
[19]
Consolacion, Y.; Ragasa, R.M.; Levida, M.J.D.; Chang, C.S. Cytotoxic isothiocyanates from Moringa oleifera Lam Seeds. Philipp. Sci. Lett., 2012, 5, 46-52.
[20]
Waterman, C.; Diana, M.C.; Patricio, R.S.; Poulev, A.; Dreifus, J.; Lila, M.A.; Raskina, I. Stable, water extractable isothiocyanates from Moringa oleifera leaves attenuate inflammation in vitro. Phytochemistry, 2014, 103, 114-122.
[21]
Navarro, S.L.; Lampe, W.J. Mechanisms of action of isothiocyanates in cancer chemoprevention: An Update. Food Funct., 2011, 2(10), 579-587.
[22]
Bones, A.M.; Hara, M.; John, T.R.; Ralph, K. Editorial: Physiology and cellular mechanisms of isothiocyanates and other glucosinolate degradation products in plants. Front. Plant Sci., 2015, 6, 1105.
[23]
Costa, L.A.; Ottoni, H.F.M.; dos Santos, M.G.; Meireles, A.B.; de-Almeida, G.V.; Pereira, F.W.; de Avelar-Freitas, A.B.; Brito-Melo, E.A.G. Dimethyl Sulfoxide (DMSO) decreases cellproliferation and TNF-, IFN-, and IL-2, cytokines production in cultures of peripheral blood lymphocytes. Molecules, 2017, 22, 1789.
[24]
Sakai, H.; Kokura, S.; Ishikawa, T.; Tsuchiya, R.; Okajima, M.; Matsuyama, T.; Adachi, S.; Katada, K.; Kamada, K.; Uchiyama, K.; Handa, O. Effects of anticancer agents on cell viability, proliferative activity and cytokine production of peripheral blood mononuclear cells. J. Clin. Biochem. Nutr., 2013, 52, 64-71.
[25]
Porter, A.G.; Jänicke, R.U. Emerging roles of caspase-3 in apoptosis. Cell Death Differ., 1999, 6, 99-104.


Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 19
ISSUE: 5
Year: 2019
Page: [677 - 686]
Pages: 10
DOI: 10.2174/1871520619666190206164137
Price: $58

Article Metrics

PDF: 16
HTML: 3