Further Constituents Of Galianthe Thalictroides (rubiaceae) And Inhibition Of Dna Topoisomerases I And Iiα By Its Cytotoxic β-carboline Alkaloids

A new cytotoxic β-carboline alkaloid, 1-methyl-3-(2-hydroxypropan-2- yl)-2-(5-methoxy-9H-β-carbolin-1-yl)-cyclopentanol (1), was isolated from roots of Galianthe thalictroides, together with the alkaloid 1-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-2-(5-methoxy-9H-β-carbolin-1-yl) -cyclopentanol (2), the anthraquinones 1-methyl-alizarin and morindaparvin-A, the coumarin scopoletin, homovanillic alcohol, (-)-epicatechin, and the steroids stigmast-4-en-3-one, 4,22-stigmastadien-3-one, campest-4-en-3-one, stigmast-4-en-3,6-dione, 6-β-hydroxy-stigmast-4-en-3-one, stigmasterol, campesterol, β-sitosterol, and β-sitosterol-3-O-β-d- glucopyranoside. Among the previously known compounds, homovanillic alcohol is a novel finding in Rubiaceae, while 1-methyl-alizarin, morindaparvin-A, scopoletin, stigmast-4-en-3-one, 4,22-stigmastadien-3-one, campest-4-en-3-one, stigmast-4-en-3,6-dione, and 6-β-hydroxy-stigmast-4-en-3-one is reported for the first time in the genus Galianthe. The cytotoxic β-carboline alkaloids 1 and 2 exhibited potent antitopoisomerase I and IIα activities and strong evidence is provided for their action as topoisomerase IIα poisons and redox-independent inhibitors. © 2014 Elsevier Ltd. All rights reserved.24513581361Cabral, E.L., (2009) Ann. Missouri Bot. Garden, 96, p. 27Figueiredo, P.O., Garcez, F.R., Matos, M.F.C., Perdomo, R.T., Queiroz, L.M.M., Pott, A., Garcez, A.J.S., Garcez, W.S., (2011) Planta Med., 77, p. 1852Ishida, J., Wang, H.K., Bastow, K.F., Hu, C.Q., Lee, K.H., (1999) Bioorg. Med. Chem. Lett., 9, p. 3319Sobhani, A.M., Ebrahimi, S.A., Mahmoudian, M., (2002) J. Pharm. Pharm. Sci., 5, p. 19Cao, R., Peng, W., Chen, H., Ma, Y., Liu, X., Hou, X., Guan, H., Xu, A., (2005) Biochem. Biophys. Res. Commun., 338, p. 1557Cao, R., Peng, W., Wang, Z., Xu, A., (2007) Curr. Med. Chem., 14, p. 479Meester, C., (1995) Mutat. Res., 339, p. 139Taira, Z., Kanzawas, S., Dohara, C., Ishida, S., Matsumoto, M., Sakiya, Y., (1997) J. Toxicol. Environ. Health, 43, p. 83Balon, M., Munoz, M.A., Carmona, C., Guardado, P., Galan, M., (1999) Biophysics, 80, p. 41Siu, F.M., Pommier, Y., (2013) Nucleic Acids Res., 41, p. 10010Oppegard, L.M., Nguyen, T., Ellis, K.C., Hiasa, H., (2012) J. Nat. Prod., 75, p. 1485Auzanneau, C., Montaudon, D., Jacquet, R., Puyo, S., Pouységu, L., Deffieux, D., Elkaoukabi-Chaibi, A., Pourquier, P., (2012) Mol. Pharmacol., 82, p. 134Nitiss, J.L., (2009) Nat. Rev. Cancer, 9, p. 327Wang, J.C., (2009) Untangling the Double Helix, , Cold Spring Harbor Laboratory Press New York Chapter 6Holm, C., Goto, T., Wang, J.C., Botstein, D., (1985) Cell, 41, p. 553Nitiss, J.L., (2009) Nat. Rev. Cancer, 9, p. 338Pommier, Y., Leo, E., Zhang, H., Marchand, C., (2010) Chem. Biol., 17, p. 421Wijnsma, R., Verpoorte, R., (1986) Progress in the Chemistry of Organic Natural Products, 49, pp. 79-149. , W. Herz, H. Grisebach, G.W. Kirby, Ch. Tamm, Springer Vienna Chapter 2Chang, P., Lee, K.H., Shingu, T., Hirayama, T., Hall, I.H., Huang, H.C., (1982) J. Nat. Prod., 45, p. 206Chang, P., Lee, K.H., (1984) Phytochemistry, 23, p. 1733Vasconcelos, J.M.J., Silva, A.M.S., Cavaleiro, J.A.S., (1998) Phytochemistry, 49, p. 1421Pouchert, C.J., Behnke, J., (1993) The Aldrich Library of 13C and 1H FT NMR Spectra, , Aldrich Chemical Company Milwaukee p 412Tanaka, J.C.A., Da Silva, C.C., Dias Filho, B.P., Nakamura, C.V., De Carvalho, J.E., Foglio, M.A., (2005) Quim. Nova, 28, p. 834Cui, E.J., Park, H.J., Wu, Q., Chung, I.S., Kim, J.Y., Baek, N.I., (2010) J. Appl. Biol. Chem., 53, p. 77Yayli, N., Yildirim, N., Usta, A., Özkurt, S., Akgün, V., Turk, J., (2003) Chemistry, 27, p. 749Jain, P.S., Bari, S.B., (2010) Asian J. Plant Sci., 9, p. 163Monks, A., Scudiero, D., Skehan, P., Shoemaker, R., Paull, K., Vistica, D., Hose, C., Boyd, M., (1991) J. Natl. Cancer Inst., 83, p. 757Houghton, P., Fang, R., Techatanawat, I., Steventon, G., Hylands, P.J., Lee, C.C., (2007) Methods, 42, p. 377Bauer, D.L.V., Marie, R., Rasmussen, K.H., Kristensen, A., Mir, K.U., (2012) Nucleic Acids Res., 40, p. 11428Sinha, B.K., (1995) Drugs, 49, p. 11Baxter, J., Sen, N., Martínez, V.L., De Carandini, M.E.M., Schvartzman, J.B., Diffley, J.F.X., Aragón, L., (2011) Science, 331, p. 1328Ledzewicz, U., Schättler, H., Gahrooi, M.R., Dehkordi, S.M., (2013) Math. Biosci. Eng., 10, p. 803Wang, Y., Zhou, R., Liliemark, J., Gruber, A., Lindemalm, S., Albertioni, F., Liliemark, E., (2001) Leuk. Res., 25, p. 133Funayama, Y., Nishio, K., Wakabayashi, K., Nagao, M., Shimoi, K., Ohira, T., Hasegawa, S., Saijo, N., (1996) Mutat. Res., 349, p. 183Wang, H., Mao, Y., Chen, A.Y., Zhou, N., Lavoie, E.J., Liu, L.F., (2001) Biochemistry, 40, p. 3316Bandele, O.J., Osheroff, N., (2007) Biochemistry, 46, p. 609

Estudos morfoanatômicos da semente e da plântula de espécies de Anileiras (Indigofera L., Leguminosae) Morpho-anatomical studies of seeds and seedlings of wild indigo, "anileira", Indigofera- Leguminosae

O nome popular "anileira" designa Indigofera anil L., I. suffruticosa Mill. e I. truxillensis Kunth, muito semelhantes quanto à morfologia externa. Este trabalho teve por objetivo avaliar se caracteres da semente e plântula apresentavam valor diagnóstico para este grupo, já que tais caracteres têm sido muito utilizados na Taxonomia de Leguminosae. A superfície e morfoanatomia de sementes e cotilédones foram estudadas por microscopias eletrônica de varredura e de luz, e as etapas do desenvolvimento das plântulas descritas. Embora as plântulas sejam semelhantes, caracteres de sementes (tamanho, forma, ornamentação da superfície, forma do hilo e tamanho do embrião) e cotilédones (forma, organização do parênquima lacunoso na nervura central e distribuição de metabólitos nos tecidos) apresentaram valor diagnóstico para as espécies. I. anil distingue-se de I. suffruticosa por suas sementes maiores e cotilédones com borda acuminada. I. truxillensis caracteriza-se por apresentar sementes cilíndricas e cotilédones reniformes contendo gotas de óleo e alcalóides. Nossos dados, a morfologia externa dos frutos (curvos em I. anil e I. suffruticosa, e retos em I. truxillensis) e, ainda, a anatomia foliar (células parenquimáticas grandes e fenólicas no floema de I. suffruticosa e sua ausência em I. anil) sugerem que I. anil, I. suffruticosa e I. truxillensis não devem ser sinonimizadas.<br>The common name "wild indigo" specifies Indigofera anil L., I. suffruticosa Mill. (legitimate name) and I. truxillensis Kunth (legitimate name) that are very similar due to their external morphology. This work analyzed diagnostic characteristics of seeds and seedlings of these species since such features are widely used in taxonomic approaches within Leguminosae. We studied surface features and morpho-anatomy of seeds and cotyledons with scanning electronic microscopy and light microscopy, and described seedling phases. Although seedlings are similar, seed characteristics (size, shape, surface ornamentation, shape of the hilum and embryo size) and cotyledon characteristics (shape, trichome ornamentation, organization of spongy parenchyma along central veins and metabolite distribution in the tissues) have diagnostic features for the species. I. anil differs from I. suffruticosa in its larger seeds and acuminate-margined cotyledons. I. truxillensis is recognized by its cylindrical seeds and kidney-shaped cotyledons with large oil drops. We assume that the characteristics examined, plus fruit morphology and foliar anatomy suggest that I. anil, I. suffruticosa and I. truxillensis should not be synonymized