New bioactive coumarins from Kielmeyera albopunctata.
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.
Scio
Elita
E
Laboratório de Química de Produtos Naturais, CPqRR-FIOCRUZ, Avenida Augusto de Lima, 1715, 30190-002, Belo Horizonte, MG, Brazil.
Ribeiro
Antônia
A
Alves
Tânia M A
TM
Romanha
Alvaro J
AJ
Shin
Young G
YG
Cordell
Geoffrey A
GA
Zani
Carlos L
CL
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001938:Brazil; D014355:Chagas Disease / Q000097:blood / Q000188:drug therapy; D028084:Clusiaceae / Q000737:chemistry*; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D007624:KB Cells / Q000187:drug effects; D008175:Lung Neoplasms; D008297:Male; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D024301:Plant Bark / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011471:Prostatic Neoplasms; D014344:Trypanocidal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014349:Trypanosoma cruzi / Q000187:drug effects; D014407:Tumor Cells, Cultured / Q000187:drug effects
C478139:4-(1-methylpropyl)-5,7-dihydroxy-8-(4-hydroxy-3-methylbutyryl)-6-(3-methylbut-2-enyl)chromen-2-one; C478141:5,7-dihydroxy-8-(4-hydroxy-3-methylbutyryl)-6-(3-methylbut-2-enyl)-4-phenylchromen-2-one; C478140:9-(1-methylpropyl)-4-hydroxy-5-(4-hydroxy-3-methylbutyryl)-2-(1-hydroxy-1-methylethyl)-2,3-dihydrofuro(2,3-f)chromen-7-one; D000972:Antineoplastic Agents, Phytogenic; D003374:Coumarins; D014344:Trypanocidal Agents