7,7-Dimethylaporphine and Other Alkaloids from the Bark of <i>Guatteria friesiana</i>

Costa, Emmanoel V.; Pinheiro, Maria Lúcia B.; Maia, Beatriz Helena Lameiro de Noronha Sales; Marques, Francisco A.; Ruiz, Ana Lúcia Tasca Góis; Marchetti, Gabriela M.; Carvalho, João Ernesto de; Soares, Milena Botelho Pereira; Costa, Carlos Maurício de Castro; Galvão, Alexandre F. C.; Lopes, Norberto P.; Koolen, Héctor H. F.; Bezerra, Daniel P.; Barison, Andersson

doi:10.1021/acs.jnatprod.5b01037

Cited by 24 publications

(18 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In fact, some of these alkaloids have been previously reported as cytotoxic agents. 27,[29][30][31] Moreover, the cytotoxicity of the mixture 6, 9 and 10 may due to the presence of the compound 9, which has reported with a potent cytotoxic activity. 31 Among the alkaloids evaluated, (+)-nornuciferine (1), and the mixture of 6, 9 and 10 displayed promising cytotoxicity activities with IC 50 values below to 17.0 µmol L -1 against HepG2, HL and K562.…”

Section: Resultsmentioning

confidence: 99%

ALKALOIDS FROM LEAVES OF Guatteria pogonopus (ANNONACEAE) AND THEIR CYTOTOXICITIES

et al. 2018

Self Cite

View full text Add to dashboard Cite

The phytochemical investigation of the alkaloid-rich fraction obtained from the leaves of Guatteria pogonopus Mart. (Annonaceae) allowed the isolation and identification for the first time in this species of: (+)-nornuciferine (1), a mixture of 1 and (+)-anonaine (2), (+)-isocorydine (3), (+)-nuciferine (4), (+)-roemerine (5), (−)-tetrahydropseudocolumbamine (6), a mixture of 6, liriodenine (9) and lysicamine (10), a mixture of 1,2,9-trimethoxy-10-hydroxyaporphine (7) and bulbocapnine (8), 9, 10, and (+)-N-methyllindicarpine (11). Compounds 6, 7, 8, and 11 have not been previously reported in the family Annonaceae. Furthermore, the formerly synthetic 1,2,9-trimethoxyaporfin-10-ol (7) is described for the first time as a natural aporphine alkaloid herein. The chemical structures were established by 1D and 2D NMR as well as in comparison with data previously reported in the literature. The cytotoxic activity of the alkaloids was evaluated against tumor (B16-F10, HepG2, HL-60, and K562) and non-tumor (PBMC) cell lines. Alkaloid 1 presented significant activity against HepG2 cell lines with IC 50 of 9.60 µmol L-1 while the mixture of 6, 9 and 10 displayed strong cytotoxic activity against HL-60 and K562 cell lines with IC 50 values of 3.41 an 8.50 µmol L-1 , respectively.

show abstract

Section: Resultsmentioning

confidence: 99%

ALKALOIDS FROM LEAVES OF Guatteria pogonopus (ANNONACEAE) AND THEIR CYTOTOXICITIES

et al. 2018

Self Cite

View full text Add to dashboard Cite

show abstract

“…Uma outra maneira de atuação dos alcaloides é afetar o citoesqueleto (microtúbulos ou microfilamentos). Ademais, os alcaloides podem se ligar com o DNA/RNA, podendo prevenir os processos de replicação e transcrição (WINK, 1998 (CASTEDO et al, 1991;CAVÉ 1985a;LÓPEZ et al, 1990) oxo-anolobina aporfina G. melosma Diels (ABD-EI_ATTI et al;PHOEBE et al, 1980) antiparasitário (CASTEDO et al, 1991;HOCQUEMILLER et al, 1984a;MAHIOU et al, 1994) asimilobina aporfina G. scandens Ducke (HOCGUEMILLER et al, 1982b CASSELS, 1989;CORDELL et al, 1989;COSTA et al, 2009;COSTA et al, 2010) CASSELS, 1989;COSTA et al, 2009;HOCGUEMILLER et al, 1984a) (GOULART et al, 1986; dielsiquinona azaantraquinona G. dielsiana R.E. Fr.…”

Section: L-tirosinaunclassified

“…Fr. (CORDELL et al, 1989;GOULART et al, 1986 -EI_ATTI et al, 1982;SLATKIN., 1983;CASTEDO et al, 1991;CAVÉ 1985a;COSTA et al, 2009;COSTA et al, 2010;DE CARVALHO BAYMA et al, 1987;GOULART et al, 1986;LÓPEZ et al, 1990;PHOEBE et al, 1980;WENIGER et al, 2000;ZHANG et al, 2002 (CALVÉ et al, 1989;CORTES et al, 1986;COSTA et al, 2010;LIMA et al, 2004;GARBARINO;PETZALL;SALAZAL, 1984;MONTENEGRO et al, 2003;ZHANG et al, 2002) N (CORTES et al, 1986;GOULART et al, 1986;LÓPEZ et al, 1990;LÓPEZ et al, 1992;WENIGER et al, 2000) desidro COSTA et al, 2010;COSTA et al, 2012;CORTES et al, 1986;HOQUEMILLER et al, 1984b;LÓPEZ et al, 1992;MONTENEGRO et al, 2003;SAEZ;BLAIR;SAEZ, 1997;RASAMIZAFY et al, 1986) (-)-nornuciferina aporfina G. diospyroides Baill.…”

Section: L-tirosinamentioning

confidence: 99%

“…Figura 51. Mecanismo de fragmentação LC-EM/EM da deidronantenina (JEONG et al, 2012;MA et al, 2008) O pico em RT=6,80 min apresentou fragmentos de massas em m/z=657, 613, 352, 247, (RABELO et al, 2014), G. friesiana (COSTA et al, 2013), G. pogonopus (SANTOS et al, 2015), G. blepharophylla (COSTA et al, 2011), G. multivenia (ZHANG et al, 2002), G. diospyroides (PERÉZ-AMADOR et al, 2004) e G. goudotiana (CASTEDO et al, 1991 (COSTA et al, 2010;COSTA et al, 2009;LIMA et al, 2004;MONTENEGRO et al, 2003;ZHANG et al, 2002;CAVÉ et al, 1989;CORDELL et al, 1989CORTES et al, 1986GARBARINO;PETZALL;SALAZAL, 1984;).…”

Section: Identificação Da Amostra 10unclassified

“…Esses resultados mostraram que os alcaloides totais de G. elliptica foram mais ativos do que fração de alcaloides dos galhos de G. fresiana contra C. albicans CIM>1 mg/mL), E. coli (CIM=0,75 mg/mL) e S. aureus (CIM=0,75 mg/mL). Porém, alcaloides totais de G. friesiana foram mais ativos contra P. aeruginosa com CIM de 0,375 mg/mL (COSTA et al, 2009). Além disso, os alcaloides totais de G. elliptica foram mais ativos do que alcaloides isolados (O-metilmoschatolina, lisicamina e liriodenina) de G. hispida, que apresentaram CIM > 1 mg/mL para C. albicans, S. aureus, E. coli e P. aeruginosa (COSTA et al, 2010).…”

Section: Atividade Antifúngica -Método Qualitativounclassified

See 2 more Smart Citations

Análise química e atividades biológicas de <i>Guatteria elliptica</i> R. E. Fries (Annonaceae)

Ferreira¹

View full text Add to dashboard Cite

show abstract

Characterization of aporphine alkaloids by electrospray ionization tandem mass spectrometry and density functional theory calculations

Neto

Andréo

Raftery

et al. 2019

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

Rationale Aporphine alkaloids represent a large group of isoquinoline natural products with important roles in biological and biomedical areas. Their characterization by electrospray ionization tandem mass spectrometry (ESI‐MS/MS) can contribute to their rapid identification in complex biological matrices. Methods We report the fragmentation of protonated 7,7‐dimethylaporphine alkaloids by ESI‐MS/MS, and the putative annotation of aporphine alkaloids in plant extracts. We used low‐ and high‐resolution MS/MS analyses to rationalize the fragmentation pathways, and employed the B3LYP/6‐31 + G(d,p) density functional theory (DFT) model to provide thermochemical parameters and to obtain the reactive sites. Results DFT calculations of a set of 7,7‐dimethylaporphine alkaloids suggested the heterocyclic amino group as the most basic site due to the proton affinity of the nitrogen atom. Collision‐induced dissociation experiments promoted •OCH3 elimination instead of the expected neutral loss of the heterocyclic amino group, pointing to the [M − 15 + H]•+ ion as the diagnostic fragment for 7,7‐dimethylaporphine alkaloids. The analysis of plant extracts led to the annotation of 25 aporphine alkaloids. Their fragmentation initiated with the loss of the amino group followed by formation of a cyclic carbocation. Further reactions derived from consecutive charge‐remote and/or charge‐induced fragmentations of the substituents attached to the aromatic system. The mechanisms were re‐examined based on plausible gas‐phase ion chemistry reactions. Conclusions Taken together, the diagnostic product ions and the series of radical and neutral eliminations provided information about the location of methylenedioxy, aromatic methoxy, and vicinal methoxy and hydroxy groups in aporphine alkaloids, assisting their characterization via MS/MS.

show abstract

7,7-Dimethylaporphine and Other Alkaloids from the Bark of Guatteria friesiana

Cited by 24 publications

References 27 publications

ALKALOIDS FROM LEAVES OF Guatteria pogonopus (ANNONACEAE) AND THEIR CYTOTOXICITIES

ALKALOIDS FROM LEAVES OF Guatteria pogonopus (ANNONACEAE) AND THEIR CYTOTOXICITIES

Análise química e atividades biológicas de <i>Guatteria elliptica</i> R. E. Fries (Annonaceae)

Characterization of aporphine alkaloids by electrospray ionization tandem mass spectrometry and density functional theory calculations

Contact Info

Product

Resources

About