Planta Med 2014; 80 - PC11
DOI: 10.1055/s-0034-1382393

New antimalarial benzopyran derivatives from the endophytic fungus Alternaria phragmospora

A Metwaly 1, H Kadry 1, A El-Hela 1, A Elsalam 1, S Ross 2
  • 1Pharmacognosy Department, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt
  • 2National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, USA

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

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