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Anti-Cancer Agents in Medicinal Chemistry

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ISSN (Print): 1871-5206
ISSN (Online): 1875-5992

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Research Article

Evaluation of Antiproliferative Activity of Lac Dye Fractions against MDA-MB-231 and SiHa Cell Lines

Author(s): Pankaj Dagur and Manik Ghosh*

Volume 22, Issue 14, 2022

Published on: 31 March, 2022

Page: [2577 - 2585] Pages: 9

DOI: 10.2174/1872210516666220224095221

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Abstract

Background: Laccifer lacca (Kerr) produces a mixture of polyhydroxy anthraquinones (laccaic acid) known as lac dye. Literature suggests that these laccaic acids have a structural resemblance with the anticancer drug Adriamycin (ADR). Hence, they may possess potential anticancer activity.

Methods: This study was designed to explore the in vitro anticancer activity of the three fractions of lac dye, i.e., chloroform (C), methanol (M), and water (W) fractions, and isolation of constituents from bioactive fraction.

Results: SRB (Sulforhodamine B) assay method was employed to evaluate the inhibitory action of all three fractions. However, only methanolic showed promising inhibitory action with GI50 <10; this runs in parallel with Adriamycin inhibition (GI50 <10). Two active constituents of the methanolic extract were isolated using column chromatography and were characterized using UV (UV visible spectrophotometer), IR (Infrared spectroscopy), NMR (nuclear magnetic resonance), and mass spectrometry methods. The final structure of the isolated constituents (laccaic acid D and laccaic acid B) was confirmed by 13C and 2D NMR data.

Conclusion: Conclusively, only the methanol fraction (M) showed promising anticancer activity against in vitro MDAMB- 231 and SiHa cell lines compared to the standard adriamycin.

Keywords: Anticancer, SRB, MDA-MB-231, SiHa, laccaic acid B, laccaic acid D, DEPT, 2D NMR.

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[1]
Lozano, R.; Naghavi, M.; Foreman, K.; Lim, S.; Shibuya, K.; Aboyans, V.; Abraham, J.; Adair, T.; Aggarwal, R.; Ahn, S.Y.; Alvarado, M.; Anderson, H.R.; Anderson, L.M.; Andrews, K.G.; Atkinson, C.; Baddour, L.M.; Barker-Collo, S.; Bartels, D.H.; Bell, M.L.; Benjamin, E.J.; Bennett, D.; Bhalla, K.; Bikbov, B.; Bin Abdulhak, A.; Birbeck, G.; Blyth, F.; Bolliger, I.; Boufous, S.; Bucello, C.; Burch, M.; Burney, P.; Carapetis, J.; Chen, H.; Chou, D.; Chugh, S.S.; Coffeng, L.E.; Colan, S.D.; Colquhoun, S.; Colson, K.E.; Condon, J.; Connor, M.D.; Cooper, L.T.; Corriere, M.; Cortinovis, M.; de Vaccaro, K.C.; Couser, W.; Cowie, B.C.; Criqui, M.H.; Cross, M.; Dabhadkar, K.C.; Da-hodwala, N.; De Leo, D.; Degenhardt, L.; Delossantos, A.; Denenberg, J.; Des Jarlais, D.C.; Dharmaratne, S.D.; Dorsey, E.R.; Driscoll, T.; Duber, H.; Ebel, B.; Erwin, P.J.; Espindola, P.; Ezzati, M.; Feigin, V.; Flaxman, A.D.; Forouzanfar, M.H.; Fowkes, F.G.; Franklin, R.; Fran-sen, M.; Freeman, M.K.; Gabriel, S.E.; Gakidou, E.; Gaspari, F.; Gillum, R.F.; Gonzalez-Medina, D.; Halasa, Y.A.; Haring, D.; Harrison, J.E.; Havmoeller, R.; Hay, R.J.; Hoen, B.; Hotez, P.J.; Hoy, D.; Jacobsen, K.H.; James, S.L.; Jasrasaria, R.; Jayaraman, S.; Johns, N.; Karthikeyan, G.; Kassebaum, N.; Keren, A.; Khoo, J.P.; Knowlton, L.M.; Kobusingye, O.; Koranteng, A.; Krishnamurthi, R.; Lipnick, M.; Lipshultz, S.E.; Ohno, S.L.; Mabweijano, J.; MacIntyre, M.F.; Mallinger, L.; March, L.; Marks, G.B.; Marks, R.; Matsumori, A.; Matzopoulos, R.; Mayosi, B.M.; McAnulty, J.H.; McDermott, M.M.; McGrath, J.; Mensah, G.A.; Merriman, T.R.; Michaud, C.; Miller, M.; Miller, T.R.; Mock, C.; Mocumbi, A.O.; Mokdad, A.A.; Moran, A.; Mulholland, K.; Nair, M.N.; Naldi, L.; Narayan, K.M.; Nasseri, K.; Norman, P.; O’Donnell, M.; Omer, S.B.; Ortblad, K.; Osborne, R.; Ozgediz, D.; Pahari, B.; Pandian, J.D.; Rivero, A.P.; Padilla, R.P.; Perez-Ruiz, F.; Perico, N.; Phillips, D.; Pierce, K.; Pope, C.A., III; Porrini, E.; Pourmalek, F.; Raju, M.; Ranganathan, D.; Rehm, J.T.; Rein, D.B.; Remuzzi, G.; Rivara, F.P.; Roberts, T.; De León, F.R.; Rosenfeld, L.C.; Rushton, L.; Sacco, R.L.; Salomon, J.A.; Sampson, U.; Sanman, E.; Schwebel, D.C.; Segui-Gomez, M.; Shepard, D.S.; Singh, D.; Singleton, J.; Sliwa, K.; Smith, E.; Steer, A.; Taylor, J.A.; Thomas, B.; Tleyjeh, I.M.; Towbin, J.A.; Truelsen, T.; Undurraga, E.A.; Venketasubramanian, N.; Vijayakumar, L.; Vos, T.; Wagner, G.R.; Wang, M.; Wang, W.; Watt, K.; Weinstock, M.A.; Weintraub, R.; Wilkinson, J.D.; Woolf, A.D.; Wulf, S.; Yeh, P.H.; Yip, P.; Zabetian, A.; Zheng, Z.J.; Lopez, A.D.; Murray, C.J.; AlMazroa, M.A.; Memish, Z.A. Global and regional mortality from 235 causes of death for 20 age groups in 1990 and 2010: A systematic analysis for the Global Burden of Disease Study 2010. Lancet, 2012, 380(9859), 2095-2128.
[http://dx.doi.org/10.1016/S0140-6736(12)61728-0] [PMID: 23245604]
[2]
Anitha, S.S. Pharmacological activity of vinca alkaloids. J. Pharmacogn. Phytochem., 2016, 4, 27-34.
[3]
Kalantari, S.; Roufegarinejad, L.; Pirsa, S.; Gharekhani, M. Green extraction of bioactive compounds of pomegranate peel using β-Cyclodextrin and ultrasound. Main Group Chem., 2020, 19(1), 61-80.
[http://dx.doi.org/10.3233/MGC-190821]
[4]
NISCAIR. Available from: http://nsdl.niscair.res.in/jspui/bitstream/123456789/219/1/LAC%20CULTURE.pdf
[5]
Wang, X.; Li, J.Z.; Fan, Y.M.; Jin, X.J. Present research on the composition and application of lac. For. Stud. China, 2006, 8(1), 65-69.
[http://dx.doi.org/10.1007/s11632-006-0012-9]
[6]
Dey, S.; Ghosh, M. An anticancer agent from laccifer lacca (Kerr): Laccaic acid-A. Indian J. Tradit. Knowl., 2019, 18(4), 677-685.
[7]
Fagan, R.L.; Cryderman, D.E.; Kopelovich, L.; Wallrath, L.L.; Brenner, C. Laccaic acid A is a direct, DNA-competitive inhibitor of DNA methyltransferase 1. J. Biol. Chem., 2013, 288(33), 23858-23867.
[http://dx.doi.org/10.1074/jbc.M113.480517] [PMID: 23839987]
[8]
Jimtaisong, A.; Janthadee, R.; Nakrit, T. In vitro antioxidant activities of laccaic acids and its aluminum lake. Food Sci. Biotechnol., 2013, 22(4), 1055-1061.
[http://dx.doi.org/10.1007/s10068-013-0183-9]
[9]
Sekido, C.; Nishimura, N.; Takai, M.; Hasumi, K. Inhibition of plasma hyaluronan-binding protein autoactivation by laccaic acid. Biosci. Biotechnol. Biochem., 2010, 74(11), 2320-2322.
[http://dx.doi.org/10.1271/bbb.100373] [PMID: 21071862]
[10]
Burwood, R.; Read, G.; Schofield, K.; Wright, D.E. The pigments of stick lac. Part I. Isolation and preliminary examination. J. Chem. Soc., 1965, 6067-6073.
[http://dx.doi.org/10.1039/JR9650006067]
[11]
Burwood, R.; Read, G.; Schofield, K.; Wright, D.E. The pigments of stick lac. Part II. The structure of laccaic acid A. J. Chem. Soc. C, 1967, 842-851.
[http://dx.doi.org/10.1039/J39670000842]
[12]
Bhide, N.S.; Pandhare, E.D.; Rama Rao, A.V.; Shaikh, I.N.; Srinivasan, R. Lac pigments: Part IV. Constitution of laccaic acid B. Indian J. Chem., 1969, 7(10), 987-995.
[13]
Mehandale, A.R.; Rao, A.R.; Shaikh, I.N.; Venkataraman, K. Desoxyerythrolaccin and laccaic acid D. Tetrahedron Lett., 1968, 9(18), 2231-2234.
[http://dx.doi.org/10.1016/S0040-4039(00)89727-0]
[14]
Oka, H.; Ito, Y.; Yamada, S.; Kagami, T.; Hayakawa, J.; Harada, K.; Atsumi, E.; Suzuki, M.; Suzuki, M.; Odani, H.; Akahori, S.; Maeda, K.; Nakazawa, H.; Ito, Y. Separation of lac dye components by high-speed counter-current chromatography. J. Chromatogr. A, 1998, 813(1), 71-77.
[http://dx.doi.org/10.1016/S0021-9673(98)00311-2] [PMID: 9697316]
[15]
Oka, H.; Ito, Y.; Yamada, S.; Kagami, T.; Hayakawa, J.; Harada, K.; Atsumi, E.; Suzuki, M.; Suzuki, M.; Odani, H.; Akahori, S.; Maeda, K.; Tanaka, T.; Mizuno, M. Identification of lac dye components by electrospray high performance liquid chromatography-tandem mass spectrometry. J. Mass Spectrom. Soc. Jpn., 1998, 46(1), 63-68.
[http://dx.doi.org/10.5702/massspec.46.63]
[16]
Hirata, K.; Uematsu, Y.; Suzuki, K.; Iida, K.; Kamata, K. Analysis of lac color in diets and feces of rats for toxicity studies Shokuhin Eiseigaku Zasshi 2002, 43(2), 110-113.
[http://dx.doi.org/10.3358/shokueishi.43.110] [PMID: 12092412]
[17]
Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J.T.; Bokesch, H.; Kenney, S.; Boyd, M.R. New color-imetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 1990, 82(13), 1107-1112.
[http://dx.doi.org/10.1093/jnci/82.13.1107] [PMID: 2359136]
[18]
Vichai, V.; Kirtikara, K. Sulforhodamine B colorimetric assay for cytotoxicity screening. Nat. Protoc., 2006, 1(3), 1112-1116.
[http://dx.doi.org/10.1038/nprot.2006.179] [PMID: 17406391]
[19]
Birkinshaw, J.H. Ultraviolet absorption spectra of some polyhydroxyanthraquinones. Biochem. J., 1955, 59(3), 485-486.
[http://dx.doi.org/10.1042/bj0590485] [PMID: 14363123]
[20]
Khurana, R.G.; Singh, A.N.; Upadhye, A.B.; Mhaskar, V.V.; Dev, S. Chemistry of lac resin-III: Lac acids-3: An integrated procedure for their isolation from hard resin; chromatography characteristics and quantitative determination. Tetrahedron, 1970, 26(17), 4167-4175.
[http://dx.doi.org/10.1016/S0040-4020(01)93058-3]
[21]
Wadia, M.S.; Khurana, R.G.; Mhaskar, V.V.; Dev, S. Chemistry of lac resin-I: Lac acids (part 1): Butolic, jalaric and laksholic acids. Tetrahedron, 1969, 25(17), 3841-3853.
[http://dx.doi.org/10.1016/S0040-4020(01)82916-1]

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