Aspergillusol A, an alpha-glucosidase inhibitor from the marine-derived fungus Aspergillus aculeatus.
A new tyrosine-derived metabolite, aspergillusol A (4), was isolated on a gram scale, together with a methyl ester of 4-hydroxyphenylpyruvic acid oxime (5) and secalonic acid A, from the marine-derived fungus Aspergillus aculeatus CRI323-04. The tetraol in 4 was identified as erythritol by comparison of the 1H NMR spectrum of its benzoylated derivative with those of benzoylated erythritol (7) and D-threitol (8), as well as by cellulose-based chiral HPLC analysis. Aspergillusol A (4) selectively inhibited alpha-glucosidase from the yeast Saccharomyces cerevisiae, but it was inactive toward the alpha-glucosidase from the bacterium Bacillus stearothermophilus.
Ingavat
Nattha
N
Chulabhorn Graduate Institute and the Center for Environmental Health, Toxicology and Management of Chemicals (ETM), Chemical Biology Program, Vibhavadi-Rangsit Road, Laksi, Bangkok 10210, Thailand.
Dobereiner
Jeffrey
J
Wiyakrutta
Suthep
S
Mahidol
Chulabhorn
C
Ruchirawat
Somsak
S
Kittakoop
Prasat
P
D001230:Aspergillus / Q000737:chemistry*; D001411:Geobacillus stearothermophilus / Q000187:drug effects / Q000201:enzymology*; D065089:Glycoside Hydrolase Inhibitors; D008386:Marine Biology; D015394:Molecular Structure; D012441:Saccharomyces cerevisiae / Q000187:drug effects / Q000201:enzymology*; D013237:Stereoisomerism; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D044004:Xanthones / Q000302:isolation & purification
D065089:Glycoside Hydrolase Inhibitors; D044004:Xanthones; C545427:aspergillusol A; D014443:Tyrosine; C009218:secalonic acid