Abstract:
Five new polyoxygenated marine steroids-punicinols A-E (1-5)-were isolated from the gorgonian Leptogorgia punicea and characterized by spectroscopic methods (IR, MS, 1H, 13C and 2-D NMR). The five compounds induced in vitro cytotoxic effects against lung cancer A549 cells, while punicinols A and B were the most active, with IC50 values of 9.7 μM and 9.6 μM, respectively. The synergistic effects of these compounds with paclitaxel, as well as their effects on cell cycle distribution and their performance in the clonogenic assay, were also evaluated. Both compounds demonstrated significant synergistic effects with paclitaxel. © 2014 by the authors licensee MDPI Basel Switzerland.
Registro:
Documento: |
Artículo
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Título: | Polyoxygenated steroids from the octocoral leptogorgia punicea and in vitro evaluation of their cytotoxic activity |
Autor: | Moritz, M.I.G.; Marostica, L.L.; Bianco, É.M.; Almeida, M.T.R.; Carraro, J.L.; Cabrera, G.M.; Palermo, J.A.; Simões, C.M.O.; Schenkel, E.P. |
Filiación: | Post-Graduation Program in Pharmacy, Federal University of Santa Catarina, Florianópolis, SC, 88040-900, Brazil Invertebrates Department National Museum, Federal University of Rio de Janeiro, Rio de Janeiro RJ, 20940-040, Brazil MYMFOR-Department of Organic Chemistry, FCEN, University of Buenos Aires, Buenos Aires, C1428EGA, Argentina
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Palabras clave: | A549 cells; Cytotoxic effects; Leptogorgia punicea; Lung cancer cells; Octocoral; Polyoxygenated steroids; cytotoxic agent; paclitaxel; punicinol A; punicinol B; punicinol C; punicinol D; punicinol E; unclassified drug; paclitaxel; steroid; A549 cell line; antiproliferative activity; Article; biological activity; carbon nuclear magnetic resonance; clonogenic assay; controlled study; coral; drug cytotoxicity; drug effect; drug isolation; drug potentiation; drug structure; IC50; in vitro study; infrared spectroscopy; Leptogorgia punicea; mass spectrometry; nonhuman; physical chemistry; proton nuclear magnetic resonance; animal; Anthozoa; cell cycle; chemistry; drug effects; human; Lung Neoplasms; nuclear magnetic resonance spectroscopy; procedures; tumor cell line; Gorgonia; Leptogorgia punicea; Animals; Anthozoa; Cell Cycle; Cell Line, Tumor; Drug Synergism; Humans; Lung Neoplasms; Magnetic Resonance Spectroscopy; Paclitaxel; Steroids |
Año: | 2014
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Volumen: | 12
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Número: | 12
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Página de inicio: | 5864
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Página de fin: | 5880
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DOI: |
http://dx.doi.org/10.3390/md12125864 |
Título revista: | Marine Drugs
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Título revista abreviado: | Mar. Drugs
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ISSN: | 16603397
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CODEN: | MDARE
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CAS: | paclitaxel, 33069-62-4; Paclitaxel; Steroids
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_16603397_v12_n12_p5864_Moritz |
Referencias:
- Rocha, J., Peixe, L., Gomes, N.C.M., Calado, R., Cnidarians as a source of new marine bioactive compounds-An overview of the last decade and future steps for bioprospecting (2011) Mar. Drugs, 9, pp. 1860-1886
- Blunt, J.W., Copp, B.R., Keyzers, R.A., Munro, M.H.G., Prinsep, M.R., Marine natural products (2014) Nat. Prod. Rep., 31, pp. 160-258
- Pérez, C.D., Primeiro registro de Leptogorgia punicea (Milne-Edwards & Haime) (Cnidaria, Octocorallia) para o estado do Maranhão, Brasil (2005) Rev. Bras. Zool., 22, pp. 810-811
- Breedy, O., Guzman, H.M., Leptogorgia ignita, a new shallow-water coral species (Octocorallia: Gorgoniidae) from the tropical eastern Pacific (2008) J. Mar. Biol. Assoc. UK, 88, pp. 893-899
- Ksebati, M.B., Ciereszko, L.S., Schmitz, F.J., 11β, 12β-Epoxypukalide, a furanocembranolide from the gorgonian Leptogorgia setacea (1984) J. Nat. Prod., 47, pp. 1009-1012
- Gutiérrez, M., Capson, T.L., Guzmán, H.M., González, J., Ortega-Barría, E., Quiñoá, E., Riguera, R., Leptolide, a new furanocembranolide diterpene from leptogorgia alba (2005) J. Nat. Prod., 68, pp. 614-616
- Dorta, E., Díaz-Marrero, A.R., Brito, I., Cueto, M., D'Croz, L., Darias, J., The oxidation profile at C-18 of furanocembranolides may provide a taxonomical marker for several genera of octocorals (2007) Tetrahedron, 63, pp. 9057-9062
- Shapo, J.L., Moeller, P.D., Galloway, S.B., Antimicrobial activity in the common seawhip, Leptogorgia virgulata (Cnidaria: Gorgonaceae) (2007) Comp. Biochem. Physiol., 148, pp. 65-73
- Ortega, M.J., Zubía, E., Sánchez, M.C., Carballo, J.L., Cembrane diterpenes from the gorgonian leptogorgia laxa (2008) J. Nat. Prod., 71, pp. 1637-1639
- Epifanio, R.A., Maia, L.F., Fenical, W., Chemical defenses of the endemic brazialian gorgonian lophogorgia violacea pallas (octocorallia, gorgonacea) (2000) J. Braz. Chem. Soc., 11, pp. 584-591
- Díaz-Marrero, A.R., Porras, G., Cueto, M., Croz, L.D., Lorenzo, M., San-Martín, A., Darias, J., Leptogorgolide, a biogenetically interesting 1,4-diketo-cembranoid that reinforces the oxidation profile of C-18 as taxonomical marker for octocorals (2009) Tetrahedron, 65, pp. 6029-6033
- Keyzers, R.A., Gray, C.A., Schleyer, M.H., Whibley, C.E., Hendricks, D.T., Davies-Coleman, M.T., Malonganenones A-C, novel tetraprenylated alkaloids from the Mozambique gorgonian Leptogorgia gilchristi (2006) Tetrahedron, 62, pp. 2200-2206
- Cimino, G., De Rosa, S., De Stefano, S., Sodano, G., 18-Hydroxy steroids from the Mediterranean gorgonian Leptogorgia sarmentosa (1984) Experientia, 40, pp. 246-248
- Benvegnu, R., Cimino, G., De Rosa, S., De Stefano, S., Guggulsterol-like steroids from the Mediterranean gorgonian Leptogorgia sarmentosa (1982) Experientia, 38, pp. 1443-1444
- Epifanio, R.A., Maia, L.F., Pinto, A.C., Hardt, I., Fenical, W., Nature products from the gorgonian lophogorgia punicea: Isolation and structure elucidation of an unusual 17-hydroxy sterol (1998) J. Braz. C. Soc., 9, pp. 187-192
- Garrido, L., Zubia, E., Ortega, M.J., Salva, J., Isolation and structure elucidation of new cytotoxic steroids from the gorgonian Leptogorgia sarmentosa (2000) Steroids, 65, pp. 85-88
- Stonik, V.A., Marine polar steroids (2001) Russ. Chem. Rev., 70, pp. 673-715
- Gupta, A., Kumar, B.S., Negi, A.S., Current status on development of steroids as anticancer agents (2013) J. Steroid Biochem. Mol. Biol., 137, pp. 242-270
- Salvador, J.A.R., Carvalho, J.F.S., Neves, M.A.C., Silvestre, S.M., Leitão, A.J., Silva, M.M.C., Melo, M.L.S. Anticancer steroids: Linking natural and semi-synthetic compounds (2013) Nat. Prod. Rep., 30, pp. 324-374
- Pettit, G.R., Inoue, M., Kamano, Y., Herald, D.L., Arm, C., Dufresne, C., Christie, N.D., Krup, T.S., Isolation and structure of the powerful cell growth inhibitor cephalostatin 1 (1988) J. Am. Chem. Soc., 110, pp. 2006-2007
- Boonananwong, S., Kongkathip, B., Kongkathip, N., First synthesis of 3,16,20-polyoxygenated cholestanes, new cytotoxic steroids from the gorgonian Leptogorgia sarmentosa (2008) Steroids, 73, pp. 1123-1127
- Mellado, G.G., Zubia, E., Ortega, M.J., López-González, P.J., New polyoxygenated steroids from the Antarctic octocoral Dasystenella acanthine (2004) Steroids, 69, pp. 291-299
- Bianco, E.M., Oliveira, S.Q., Rigotto, C., Tonini, M.L., Guimarães, T.R., Bittencourt, F., Gouvea, L.P., Moritz, M.I.G., Anti-Infective potential of marine invertebrates and seaweeds from the Brazilian coast (2013) Molecules, 18, pp. 5761-5778
- Kasal, A., Budesinski, M., Griffiths, W.J., Spectroscopic methods of steroid analysis (2010) Steroid Analysis, 102p. , Makin, H.L.J., Gower, D.B. Springer: London, UK
- Yoshikawa, K., Kanekuni, S., Hanahusa, M., Arihara, S., Ohta, T., Polyhydroxylated sterols from the octocoral dendronephthya gigantean (2000) J. Nat. Prod., 63, pp. 670-672
- Li, R., Shao, C., Qi, X., Li, X., Li, J., Sun, L., Wang, C., Polyoxygenated sterols from the south china sea soft coral sinularia sp (2012) Mar. Drugs, 10, pp. 1422-1432
- Chen, W., Wang, S., Duh, C., Polyhydroxylated steroids from bamboo coral isis hippuris (2011) Mar. Drugs, 9, pp. 1829-1839
- Moldowan, J.M., Tan, W.L., Djerassi, C., 24å-Methylcholestane-3β,5α,6β,25-Pentol 25-monoacetate, a novel polyoxygenated marine sterol (1975) Steroids, 26, pp. 107-128
- Iwamaru, A., Iwado, E., Kondo, S., Newman, R., Vera, B., Rodríguez, A., Kondo, Y., Eupalmerin acetate, a novel anticancer agent from Caribbean gorgonian octocorals, induces apoptosis in malignant glioma cells via the c-Jun NH2 terminal kinase pathway (2007) Mol. Cancer Ther., 6, pp. 184-192
- Wang, P., Tang, H., Liu, B.S., Li, T.J., Sun, P., Zhu, W., Luo, Y.P., Zhang, W., Tumor cell growth inhibitory activity and structure-activity relationship of polyoxygenated steroids from the gorgonian Menella kanisa (2013) Steroids, 78, pp. 951-958
- Franken, N.A.P., Rodermond, H.M., Stap, J., Haveman, J., Van Bree, C., Clonogenic assays of cells in vitro (2006) Nat. Protoc., 1, pp. 2315-2319
- Chou, T.C., Theoretical basis, experimental design, and computerized simulation of synergism and antagonism in drug combination studies (2006) Pharmacol. Rev., 58, pp. 621-681
- Carvalho, J., Silva, M.M.C., Moreira, J.N., Simões, S., Sá E Melo, M.L., Selective cytotoxicity of oxysterols through structural modulation on rings a and b. Synthesis, in vitro evaluation and SAR (2011) J. Med. Chem., 54, pp. 6375-6393
- Liu, T.F., Lu, X., Tang, H., Zhang, M.M., Wang, P., Sun, P., Liu, Z.Y., Rui, Y.C., 3β,5α,6β-Oxygenated sterols from the south china sea gorgonian muriceopsis flavida and their tumor cell growth inhibitory activity and apoptosis-inducing function (2013) Steroids, 78, pp. 108-114
- Vichai, V., Kirtikara, K., Sulforhodamine b colorimetric assay for cytotoxicity screening (2006) Nat. Protoc., 1, pp. 1112-1116
Citas:
---------- APA ----------
Moritz, M.I.G., Marostica, L.L., Bianco, É.M., Almeida, M.T.R., Carraro, J.L., Cabrera, G.M., Palermo, J.A.,..., Schenkel, E.P.
(2014)
. Polyoxygenated steroids from the octocoral leptogorgia punicea and in vitro evaluation of their cytotoxic activity. Marine Drugs, 12(12), 5864-5880.
http://dx.doi.org/10.3390/md12125864---------- CHICAGO ----------
Moritz, M.I.G., Marostica, L.L., Bianco, É.M., Almeida, M.T.R., Carraro, J.L., Cabrera, G.M., et al.
"Polyoxygenated steroids from the octocoral leptogorgia punicea and in vitro evaluation of their cytotoxic activity"
. Marine Drugs 12, no. 12
(2014) : 5864-5880.
http://dx.doi.org/10.3390/md12125864---------- MLA ----------
Moritz, M.I.G., Marostica, L.L., Bianco, É.M., Almeida, M.T.R., Carraro, J.L., Cabrera, G.M., et al.
"Polyoxygenated steroids from the octocoral leptogorgia punicea and in vitro evaluation of their cytotoxic activity"
. Marine Drugs, vol. 12, no. 12, 2014, pp. 5864-5880.
http://dx.doi.org/10.3390/md12125864---------- VANCOUVER ----------
Moritz, M.I.G., Marostica, L.L., Bianco, É.M., Almeida, M.T.R., Carraro, J.L., Cabrera, G.M., et al. Polyoxygenated steroids from the octocoral leptogorgia punicea and in vitro evaluation of their cytotoxic activity. Mar. Drugs. 2014;12(12):5864-5880.
http://dx.doi.org/10.3390/md12125864