Abstract
From an extract prepared from the grain-based culture of Malbranchea flavorosea two new polyketides, namely, 8-chloroxylarinol A (1) and flavoroseoside (2), along with the known compounds xylarinol A (3), xylarinol B (4), massarigenins B and C (5 and 6), and clavatol (7), were isolated. The structures of 1 and 2 were elucidated using spectroscopic methods and corroborated by single-crystal X-ray diffraction analysis. In the case of compound 2 the absolute configuration at the stereogenic centers was established according to the method of Flack. In addition, the X-ray structure of compound 6 is reported for the first time. Compounds 3, 4, and 6 significantly inhibited yeast α-glucosidase. Compound 6 also inhibited the postprandial peak during an oral sucrose tolerance assay when tested in vivo, using normal and NA/STZ-induced hyperglycemic mice.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Benzoxepins / chemistry
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Benzoxepins / isolation & purification*
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Benzoxepins / pharmacology*
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Glycoside Hydrolase Inhibitors / chemistry
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Glycoside Hydrolase Inhibitors / isolation & purification*
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Glycoside Hydrolase Inhibitors / pharmacology*
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Hypoglycemic Agents / chemistry
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Hypoglycemic Agents / metabolism*
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Lactones / chemistry
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Lactones / isolation & purification*
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Lactones / pharmacology*
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Magnetic Resonance Spectroscopy
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Mice
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Molecular Structure
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Polyketides / chemistry
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Polyketides / isolation & purification*
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Polyketides / pharmacology*
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Spiro Compounds / chemistry
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Spiro Compounds / isolation & purification*
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Spiro Compounds / pharmacology*
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X-Ray Diffraction
Substances
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Benzoxepins
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Glycoside Hydrolase Inhibitors
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Hypoglycemic Agents
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Lactones
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Polyketides
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Spiro Compounds
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massarigenin C
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xylarinol A
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xylarinol B