Chrobisiamone A, a new bischromone from Cassia siamea and a biomimetic transformation of 5-acetonyl-7-hydroxy-2-methylchromone into cassiarin A.
A new bischromone, chrobisiamone A (1) with an antiplasmodial activity has been isolated from the leaves of Cassia siamea and the structure was elucidated by 2D NMR analysis. Cyclization of 5-acetonyl-7-hydroxy-2-methylchromone (2) in the presence of ammonium acetate resulted in generation of cassiarin A (3) with an unprecedented tricyclic skeleton, supporting a biogenetic pathway proposed for 3.
Oshimi
Shiori
S
Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan.
Tomizawa
Yuichiro
Y
Hirasawa
Yusuke
Y
Honda
Toshio
T
Ekasari
Wiwied
W
Widyawaruyanti
Aty
A
Rudyanto
Marcellino
M
Indrayanto
Gunawan
G
Zaini
Noor Cholies
NC
Morita
Hiroshi
H
D000962:Antimalarials / Q000494:pharmacology*; D032701:Biomimetics; D002366:Cassia / Q000378:metabolism*; D002626:Chemistry, Pharmaceutical / Q000379:methods; D002867:Chromones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D015195:Drug Design; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008288:Malaria / Q000517:prevention & control; D008956:Models, Chemical; D008958:Models, Molecular; D010936:Plant Extracts / Q000737:chemistry*; D018515:Plant Leaves / Q000378:metabolism
C531396:5-acetonyl-7-hydroxy-2-methylchromone; D000962:Antimalarials; D002867:Chromones; D006575:Heterocyclic Compounds, 3-Ring; D010936:Plant Extracts; C524027:cassiarin A; C531395:chrobisiamone A