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Planta Med 2016; 82(14): 1286-1294
DOI: 10.1055/s-0042-111393
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Alkaloids from the Fungus Penicillium spathulatum as α-Glucosidase Inhibitors[*]

Paulina Del Valle
1   Facultad de Química, Universidad Nacional Autónoma de México, Ciudad de México, México
,
Ana-Laura Martínez
1   Facultad de Química, Universidad Nacional Autónoma de México, Ciudad de México, México
,
Mario Figueroa
1   Facultad de Química, Universidad Nacional Autónoma de México, Ciudad de México, México
,
Huzefa A. Raja
2   Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, North Carolina, USA
,
Rachel Mata
1   Facultad de Química, Universidad Nacional Autónoma de México, Ciudad de México, México
› Institutsangaben
Weitere Informationen

Publikationsverlauf

received 11. Mai 2016
revised 22. Juni 2016

accepted 23. Juni 2016

Publikationsdatum:
11. Juli 2016 (online)

Auch verfügbar auf
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Abstract

Benzomalvin A (1), quinolactacins A1 (2), A2 (3) and B (4), quinolonimide (5), asperphenamate (6), and a new halogenated polyhydroxyanthraquinone, namely 2-chloro-6-[2′(S)-hydroxypropyl]-1,3,8-trihydroxy-anthraquinone (7), were isolated from an organic extract obtained from the solid culture of Penicillium spathulatum B35. Compounds 2 and 3 were isolated as an epimeric mixture, and compound 4 as a racemate. The structure of 7 was elucidated using 1D and 2D NMR, combined with computational methods (density functional theory). Compound 1, the mixture of 2 and 3, racemate 4, and compound 6 inhibited the yeast α-glucosidase in a concentration-dependent fashion with IC50 values of 383.2, 273.3, 57.3, and 8.3 µM, respectively. The α-glucosidase inhibitory properties of 1 were confirmed in vivo with an oral sucrose tolerance test in normal and hyperglycemic mice (p < 0.05). Furthermore, docking studies predicted that the most stable conformers of 1 bind to yeast and mammalian α-glucosidases with a higher affinity than acarbose. Finally, 1 also showed antihyperalgesic activity when tested in the formalin assay in hyperglycemic mice (p < 0.05).

Key words

Penicillium spathulatum - Trichocomaceae - benzomalvin A - α-glucosidase inhibitors - antihyperglycemic effect - antihyperalgesic activity

* Taken, in part, from the PhD thesis of P. Del Valle.


Supporting Information

 

  • References

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