Azaphenanthrene alkaloids with antitumoral activity from Anaxagorea dolichocarpa Sprague & Sandwith (Annonaceae)

Phytochemical investigation of Anaxagorea dolichocarpa Sprague & Sandwith led to isolation of three azaphenanthrene alkaloids: eupolauramine, sampangine and imbiline 1. Their chemical structures were established on the basis of spectroscopic data from IR, HR-ESI-MS, NMR (including 2D experiments...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2011-08, Vol.16 (8), p.7125-7131
Main Authors: Lúcio, Ana Silvia Suassuna Carneiro, Almeida, Jackson Roberto Guedes da Silva, Barbosa-Filho, José Maria, Pita, João Carlos Lima Rodrigues, Branco, Marianna Vieira Sobral Castello, Diniz, Margareth de Fátima Formiga Melo, Agra, Maria de Fátima, da-Cunha, Emidio V L, da Silva, Marcelo Sobral, Tavares, Josean Fechine
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Alkaloids - isolation & purification
Alkaloids - pharmacology
Anaxagorea dolichocarpa
Annonaceae
Annonaceae - chemistry
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
antitumor activity
Aza Compounds - chemistry
Aza Compounds - isolation & purification
Aza Compounds - pharmacology
azaphenanthrene alkaloid
Cancer
Cell Line, Tumor
Cell Survival - drug effects
Communication
Drug Screening Assays, Antitumor
Heterocyclic Compounds, 4 or More Rings - chemistry
Heterocyclic Compounds, 4 or More Rings - isolation & purification
Heterocyclic Compounds, 4 or More Rings - pharmacology
Humans
Molecular Structure
Natural products
Pharmaceuticals
Phenanthrenes - chemistry
Phenanthrenes - isolation & purification
Phenanthrenes - pharmacology
Phytochemicals
Plant Bark - chemistry
Plant Extracts - chemistry
Plant Extracts - isolation & purification
Plant Extracts - pharmacology
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Summary:Phytochemical investigation of Anaxagorea dolichocarpa Sprague & Sandwith led to isolation of three azaphenanthrene alkaloids: eupolauramine, sampangine and imbiline 1. Their chemical structures were established on the basis of spectroscopic data from IR, HR-ESI-MS, NMR (including 2D experiments) and comparison with the literature. Sampangine and imbiline 1 are being described in the Anaxagorea genus for the first time. Eupolauramine and sampangine show concentration-dependent antitumoral activity in leukemic cells K562 with IC(50) of 18.97 and 10.95 µg/mL, respectively.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules16087125