New bioactive coumarins from Kielmeyera albopunctata

Elita Scio; Antônia Ribeiro; Tânia M A Alves; Alvaro J Romanha; Young G Shin; Geoffrey A Cordell; Carlos L Zani

doi:10.1021/np020597r

New bioactive coumarins from Kielmeyera albopunctata

J Nat Prod. 2003 May;66(5):634-7. doi: 10.1021/np020597r.

Authors

Elita Scio¹, Antônia Ribeiro, Tânia M A Alves, Alvaro J Romanha, Young G Shin, Geoffrey A Cordell, Carlos L Zani

Affiliation

¹ Laboratório de Química de Produtos Naturais, CPqRR-FIOCRUZ, Avenida Augusto de Lima, 1715, 30190-002, Belo Horizonte, MG, Brazil.

PMID: 12762797
DOI: 10.1021/np020597r

Abstract

The CH(2)Cl(2) extract of the stem bark of Kielmeyera albopunctata was subjected to a bioassay-linked LC-MS dereplication procedure using the KB cell line to afford the new coumarins 4-(1-methylpropyl)-5,7-dihydroxy-8-(4-hydroxy-3-methylbutyryl)-6-(3-methylbut-2-enyl)chromen-2-one (1), 9-(1-methylpropyl)-4-hydroxy-5-(4-hydroxy-3-methylbutyryl)-2-(1-hydroxy-1-methylethyl)-2,3-dihydrofuro[2,3-f]chromen-7-one (2), and 5,7-dihydroxy-8-(4-hydroxy-3-methylbutyryl)-6-(3-methylbut-2-enyl)-4-phenylchromen-2-one (3). Coumarins 1 and 3 showed moderate cytotoxicity, while 2 was inactive at 20 microg/mL. Compound 1was active in vitro against the trypomastigote form of the parasite Trypanosoma cruzi, killing 80% of the parasites after 24 h contact at 4 degrees C when added at 125 microg/mL to infected murine blood.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification*
Antineoplastic Agents, Phytogenic / pharmacology
Brazil
Chagas Disease / blood
Chagas Disease / drug therapy
Clusiaceae / chemistry*
Coumarins / chemistry
Coumarins / isolation & purification*
Coumarins / pharmacology
Humans
KB Cells / drug effects
Lung Neoplasms
Male
Mice
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Bark / chemistry
Plant Stems / chemistry
Plants, Medicinal / chemistry*
Prostatic Neoplasms
Trypanocidal Agents / chemistry
Trypanocidal Agents / isolation & purification*
Trypanocidal Agents / pharmacology
Trypanosoma cruzi / drug effects
Tumor Cells, Cultured / drug effects

Substances

4-(1-methylpropyl)-5,7-dihydroxy-8-(4-hydroxy-3-methylbutyryl)-6-(3-methylbut-2-enyl)chromen-2-one
5,7-dihydroxy-8-(4-hydroxy-3-methylbutyryl)-6-(3-methylbut-2-enyl)-4-phenylchromen-2-one
9-(1-methylpropyl)-4-hydroxy-5-(4-hydroxy-3-methylbutyryl)-2-(1-hydroxy-1-methylethyl)-2,3-dihydrofuro(2,3-f)chromen-7-one
Antineoplastic Agents, Phytogenic
Coumarins
Trypanocidal Agents