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DOI: 10.1055/s-0034-1382393
New antimalarial benzopyran derivatives from the endophytic fungus Alternaria phragmospora
Five new (2 – 6) benzopyran derivatives as well four new (7 – 10) α-pyrone derivatives have been isolated from the endophytic fungus Alternaria phragmospora. The isolated compounds were chemically identified to be monocerin (1), 6-O-demethyl monocerin (2), 11-α-hydroxymonocerin (3), fusarentin (3R, 4S) 6,7 dimethylether-4-hydroxy-10-one (4), fusarentin (3S) 6,7 dimethylether-10-one (5), fusarentin (3S, 4R, 10R) 4,10-dihydroxy-6,7 dimethyl ether (6), 5-butyl-4-methoxy-6-methyl-2 H-pyran-2-one (7), 5-butyl-6-(hydroxymethyl)-4-methoxy-2 H-pyran-2-one (8), 5-(1-hydroxybutyl)-4-methoxy-6-methyl-2 H-pyran-2-one (9), 4-methoxy-6-methyl-5-(3-oxobutyl)-2 H-pyran-2-one (10). Compounds 1 and 5 showed antimalarial activities against Plasmodium falsiparum D6 clone with IC50 values of 0.097 and 3.27 µg/mL, respectively and W2 clone with IC50 values of 0.076 and 2.517 µg/mL, respectively.
R |
R1 |
R2 |
R3 |
R |
R1 |
R2 |
R |
R1 |
R2 |
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1 |
CH3 |
H |
H |
OH |
4 |
α H |
α OH |
O |
7 |
CH2CH3 |
CH3 |
H |
2 |
H |
H |
H |
OH |
5 |
α H |
H |
O |
8 |
CH2CH3 |
CH2OH |
H |
3 |
CH3 |
β OH |
H |
OH |
6 |
β H |
β OH |
βO H |
9 |
CH2CH3 |
CH3 |
α OH |
10 |
COCH3 |
CH3 |
H |