Isolation and structure elucidation of a novel antimalarial macrocyclic polylactone, menisporopsin A, from the fungus Menisporopsis theobromae.
An antimalarial macrocyclic polylactone, menisporopsin A (1), was isolated from a cell extract of the seed fungus Menisporopsis theobromae. The structure of 1 was elucidated on the basis of spectroscopic analysis and chemical transformations, with the absolute configuration established by application of the modified Mosher method and by using chiral HPLC. Menisporopsin A (1) possesses an unprecedented residue, 2,4-dihydroxy-6-(2,4-dihydroxy-n-pentyl)benzoic acid. This compound exhibited antimalarial activity, with an IC(50) value of 4.0 microg mL(-1), and antimycobacterial activity (MIC value of 50 microg mL(-1)).
Chinworrungsee
Maneekarn
M
Department of Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
Kittakoop
Prasat
P
Isaka
Masahiko
M
Maithip
Pacharee
P
Supothina
Sumalee
S
Thebtaranonth
Yodhathai
Y
D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005658:Fungi / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D018942:Macrolides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010963:Plasmodium falciparum / Q000187:drug effects; D013785:Thailand
D000962:Antimalarials; D018942:Macrolides; C485925:menisporopsin A