Published October 31, 2020
| Version v1
Journal article
Restricted
Tropane alkaloids from the stem bark of Erythroxylum bezerrae
Creators
- 1. * & Departamento de Química Org^anica e Inorg^anica, Centro de Ci^encias, Universidade Federal do Cear�a, 60440-900, Fortaleza, CE, Brazil
Description
Brito, Luana San de O., Pinto, Francisco das Chagas L., de Filho, Manoel Odorico M., Rocha, Danilo D., Mendoza, Maria Fernanda M., Ayala, Alejandro Pedro, Bezerra, Beatriz Pinheiro, Loiola, Maria Iracema B., Canuto, Kirley M., Silveira, Edilberto R., Pessoa, Otilia Deusdenia L. (2020): Tropane alkaloids from the stem bark of Erythroxylum bezerrae. Phytochemistry (112458) 178: 1-9, DOI: 10.1016/j.phytochem.2020.112458, URL: http://dx.doi.org/10.1016/j.phytochem.2020.112458
Files
Restricted
The record is publicly accessible, but files are restricted to users with access.
Linked records
Additional details
Identifiers
- LSID
- urn:lsid:plazi.org:pub:4326FFA594301346B47D4731FFAA795A
References
- Bringmann, G., Gunther, C., Muhlbacher, J., Gunathilake, M.D.L.P., Wickramasinghe, A., 2000. Tropane alkaloids from Erythroxylum zeylanicum O. E. Schulz (Erythroxylaceae). Phytochemistry 53, 409-416. https://doi.org/10.1016/S0031- 9422(99)00561-0.
- Ch� avez, D., Cui, B., Chai, H.-B., Garcia, R., Mejia, M., Farnsworth, N.R., Cordell, G.A., Pezzuto, J.M., Kinghorn, A.D., 2002. Reversal of multidrug resistance by tropane alkaloids from the stems of Erythroxylum rotundifolium. J. Nat. Prod. 65, 606-610. https://doi.org/10.1021/np0104774.
- Chin, Y., Jones, W.P., Waybright, T.J., Mccloud, T.G., Cragg, G.M., Cassady, J.M., Kinghorn, A.D., 2009. Tropane aromatic ester alkaloids obtained from a large-scale recollection of Erythroxylum pervillei stem bark collected in Madagascar. J. Nat. Prod. 69, 414-417. https://doi.org/10.1021/np050366v.
- Christen, P., Roberts, M.F., Phillipson, J.D., Evans, W.C., 1993. Alkaloids of Erythroxylum zambesiacum stem-bark. Phytochemistry 34, 1147-1151. https://doi.org/10.1016/ S0031-9422(00)90733-7.
- Closs, G.L., 1959. The configurational equilibrium of the N-methyl group in some tropane Deuteriohalides1 . J. Am. Chem. Soc. 20, 5456-5461. https://doi.org/ 10.1021/ja01529a052.
- Cocinero, E.J., Lesarri, A., Ecija � , P., Grabow, J.U., Fern� andez, J.A., Casta~ no, F., 2010. NMethyl stereochemistry in tropinone: the conformational flexibility of the tropane motif. Phys. Chem. Chem. Phys. 12, 6076-6083. https://doi.org/10.1039/ C000528B.
- Cordeiro, L.S., Loiola, M.I.B., 2018. Flora do Cear� a, brasil: Erythroxylaceae. Rodriguesia 69, 881-903. https://doi.org/10.1590/2175-7860201869242.
- Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., Puschmann, H., 2009.
- de Oliveira, S.L., Tavares, J.F., Branco, M.V.S.C., Lucena, H.F.S., Barbosa-Filho, J.M., Agra, M. de F., do Nascimento, S.C., dos S, Aguiar J., da Silva, T.G., de Simone, C.A., de Araujo-Junior, J.X., da Silva, M.S., 2011. Tropane alkaloids from Erythroxylum caatingae plowman. Chem. Biodivers. 8, 155-165. https://doi.org/10.1002/ cbdv.200900400.
- Farrugia, L.J., 1997. Ortep-3 for windows - aversion of Ortep - III with a graphical user interface (GUI). J. Appl. Cryst. 30, 565. https://doi.org/10.1107/ S0021889897003117.
- Flack, H.D., Bernardinelli, G., 2008. The use of X-ray crystallography to determine absolute configuration. Chirality 20, 681-690. https://doi.org/10.1002/chir.20473.
- Geng, H., Liu, Y.C., Li, D.S., Xiao, C.J., Liu, Y., Li, X.N., Li, S.H., 2020. Unusual glycosidic labdane diterpenoids with cytotoxicity from the root of Phlomoides betonicoides.
- Glaser, R., Shiftan, D., Drouin, M., 1999. Conformational pseudopolymorphism and solid-state CPMAS NMR studies for determination of solvent-dependent solutionstate conformational preferences for ( )-scopolamine hydrobromide/hydrochloride salts. Org. Chem. 64, 9217-9224. https://doi.org/10.1021/jo9912956.
- Griffin, W.J., Lin, G.D., 2000. Chemotaxonomy and geographical distribution of tropane alkaloids. Phytochemistry 53, 623-637. https://doi.org/10.1016/S0031-9422(99) 00475-6.
- Grynkiewicz, G., Gadzikowska, M., 2008. Tropane alkaloids as medicinally useful natural products and their synthetic derivatives as new drugs. Pharmacol. Rep. 60, 439-463. https://doi.org/10.1002/chin.200940262.
- Hrynchuk, R.J., Barton, R.J., Robertson, B.E., 1983. The crystal structure of free base cocaine, C17H21NO4. Can. J. Chem. 61, 481-487. https://doi.org/10.1139/v83-085.
- Kohnen-Johannsen, K.L., Kayser, O., 2019. Tropane alkaloids: chemistry, pharmacology, biosynthesis and production. Molecules 24, 796. https://doi.org/10.3390/ molecules24040796.
- Lakstygal, A.M., Kolesnikova, T.O., Khatsko, S.L., Zabegalov, K.N., Volgin, A.D., Demin, K.A., Shevyrin, V.A., Wappler-Guzzetta, E.A., Kalueff, A.V., 2019. Dark classics in chemical neuroscience: atropine, scopolamine, and other anticholinergic deliriant hallucinogens. ACS Chem. Neurosci. 10, 2144-2159. https://doi.org/ 10.1021/acschemneuro.8b00615.
- Loiola, M.I.B., Agra, M. de F., Baracho, G.S., Queiroz, R.T. de, 2007. Flora da Paraiba, Brasil: erythroxylaceae Kunth. Acta Bot. Bras. 21, 473-487. https://doi.org/ 10.1590/s0102-33062007000200020.
- Mi, Q., Cui, B., Silva, G.L., Lantvit, D., Lim, E., Chai, H., Hollingshead, M.G., Mayo, J.G., Kinghorn, A.D., Pezzuto, J.M., 2002. Pervilleines B and C, new tropane alkaloid aromatic esters that reverse the multidrug-resistance in the hollow fiber assay. Canc. Lett. 184, 13-20. https://doi.org/10.1016/S0304-3835(02)00202-1.
- Mosmann, T., 1983. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 65, 55-63. https://doi.org/10.1016/0022-1759(83)90303-4.
- Oliveira, A.C., Sena-Filho, J.G., Mendes-Junior, L.G., Anjos, R.M., Ribeiro, T.P., Barbosa-Filho, J.M., Braga, V.A., Medeiros, I.A., 2012. Erythroxylum pungens elicits vasorelaxation by reducing intracellular calcium concentration in vascular smooth muscle cells of rats. Braz. J. Pharmacog. 22, 436-442. https://doi.org/10.1590/ S0102- 695X2012005000005.
- Payo-Hill, A.L., Dominguez, R.S., Suarez, M.O., Batista-Baez, M., Castro, H.T.V., Rastrelli, L., Aquino, R., 2002. Tropane alkaloids from the leaves and stem bark of Erythroxylon alaternifolium and Erythroxylon rotundifolium. Phytochemistry 54, 927-932. https://doi.org/10.1016/s0031-9422(00)00087-x.
- Plowman, T., Hensold, N., 2004. Names, types, and distribution of neotropical species of Erythroxylum (Erythroxylaceae). Brittonia 56, 1-53. https://doi.org/10.1663/0007- 196x(2004)056[0001:ntadon]2.0.co;2.
- Ribeiro, E.M. de O., Lima, L.S., David, J.M., Vale, A.E. do, Lopes, L.M.X., David, J.P., 2013. A new tropane alkaloid and other constituents of Erythroxylum rimosum (Erythroxylaceae). Phytochem. Lett. 6, 232-235. https://doi.org/10.1016/j. phytol.2013.02.008.
- Sena-Filho, J.G., Da Silva, M.S., Tavares, J.F., Oliveira, S.L., Romero, M.A.V., Xavier, H. S., Barbosa-Filho, J.M., Braz-Filho, R., 2010. Cytotoxic evaluation of pungencine: a new tropane alkaloid from the roots of Erythroxylum pungens. O. E. Schulz. Helv. Chim. Acta 93, 1742-1744. https://doi.org/10.1002/hlca.200900434.
- Sidorowicz, K., Ratkiewicz, A., Nodzewska, A., Lazny, R., 2015. Determination of the Ninvertomer stereochemistry in N-substituted nortropanones and norgranatanones using computational and NMR methods. C. R. Chim. 18, 693-704. https://doi.org/ 10.1016/j.crci.2014.10.006.
- Silva, G.L., Cui, B., Ch� avez, D., You, M., Chai, H.B., Rasoanaivo, P., Lynn, S.M., O' Neill, M.J., Lewis, J.A., Besterman, J.M., Monks, A., Farnsworth, N.R., Cordell, G. A., Pezzuto, J.M., Kinghorn, A.D., 2001. Modulation of the multidrug-resistance phenotype by new tropane alkaloid aromatic esters from Erythroxylum pervillei. J. Nat. Prod. 64, 1514-1520. https://doi.org/10.1021/np010295t .
- Sheldrick, G.M., 2008. A short history of ShelX. Acta Crystallogr. A64, 339-341. https:// doi.org/10.1107/S0108767307043930.
- Sheldrick, G.M., 2015. ShelXT-Integrated space-group and crystal-structure determination. Acta Crystallogr. A71, 3-8. https://doi.org/10.1107/ S2053273314026370.
- Wang, X., Jin, X.Y., Zhou, J.C., Zhu, R.X., Qiao, Y.N., Zhang, J.Z., Li, Y., Zhang, C.Y., Chen, W., Chang, W.Q., Lou, H.X., 2020. Terpenoids from the Chinese liverwort Heteroscyphus coalitus and their antivirulence activity against Candida albicans. Phytochemistry 174, 112324. https://doi.org/10.1016/j.phytochem.2020.112324.
- Wee, S., Carroll, F.I., Woolverton, W.L., 2006. A reduced rate of in vivo dopamine transporter binding is associated with lower relative reinforcing efficacy of stimulants. Neuropsychopharmacology 31, 351-362. https://doi.org/10.1038/sj. npp.1300795.
- Zhao, L., Johnson, K.M., Zhang, M., Flippen-Anderson, J., Kozikowski, A.P., 2000. Chemical synthesis and pharmacology of 6- and 7-hydroxylated 2-carbomethoxy-3- (p -tolyl) tropanes: Antagonism of cocaine' s locomotor stimulant effects. Med. Chem. 43, 3283-3294. https://pubs.acs.org/doi/10.1021/jm000141b.