Biologically active alkylated coumarins from Kayea assamica.
Four coumarin derivatives, theraphins A (1), B (2), C (3), and D (4), along with three known xanthones, 2-hydroxyxanthone, 1,7-dihydroxyxanthone, and 5-hydroxy-1-methoxyxanthone, were isolated from the bark of Kayea assamica (Clusiaceae) native to Myanmar. Their structures were determined using spectroscopic and chemical techniques. The absolute configuration of 1 was established by the modified Mosher ester method. Theraphins A (1), B (2), and C (3) exhibited good cytotoxicity against Col2, KB, and LNCaP human cancer cell lines. Theraphin D (4) showed mild activity only against the KB cell line. The coumarins also exhibited mild antimalarial activities.
Lee
Kyung-Hee
KH
Program for Collaborative Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA.
Chai
Hee-Byung
HB
Tamez
Pamela A
PA
Pezzuto
John M
JM
Cordell
Geoffrey A
GA
Win
Khin Khin
KK
Tin-Wa
Maung
M
D000478:Alkylation; D000818:Animals; D000962:Antimalarials / Q000302:isolation & purification / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D002738:Chloroquine / Q000494:pharmacology; D028084:Clusiaceae / Q000737:chemistry*; D003374:Coumarins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007624:KB Cells; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D002052:Myanmar; D024301:Plant Bark / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D010963:Plasmodium falciparum / Q000187:drug effects / Q000235:genetics; D014407:Tumor Cells, Cultured
D000962:Antimalarials; D000972:Antineoplastic Agents, Phytogenic; D003374:Coumarins; D002738:Chloroquine