Pycnalin, a new α-glucosidase inhibitor from Acer pycnanthum.

Ai Ogawa, Yusaku Miyamae, Atsushi Honma, Tomoyuki Koyama, Kazunaga Yazawa, Hideyuki Shigemori

Graduate School of Life and Environmental Sciences, University of Tsukuba, Japan.

Chemical & pharmaceutical bulletin 2011

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A new compound, pycnalin (1), together with four known compounds, ginnalins A (2), B (3), C (4), and 3,6-di-O-galloyl-1,5-anhydro-D-glucitol (3,6-di-GAG) (5), were isolated from Acer pycnanthum. The structure of 1 was determined on the basis of 2D-NMR spectral data and synthesis of 1. Pycnalin (1) is the first 1,5-anhydro-D-mannitol linked to a gallic acid, while compounds 2-5 were 1,5-anhydro-D-glucitol linked to gallic acids. All compounds were tested in vitro for α-glucosidase inhibitory and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activities. Pycnalin (1) exhibited moderate α-glucosidase inhibitory activity as well as free radical scavenging activity. Ginnalin A (2) and 3,6-di-GAG (5), which have two galloyl groups, exhibited potent α-glucosidase inhibition, compared to those of other compounds 1, 3, and 4 containing a galloyl group. These results suggest that α-glucosidase inhibition is influenced by the number of galloyl groups.

Citation

Ai Ogawa, Yusaku Miyamae, Atsushi Honma, Tomoyuki Koyama, Kazunaga Yazawa, Hideyuki Shigemori. Pycnalin, a new α-glucosidase inhibitor from Acer pycnanthum. Chemical & pharmaceutical bulletin. 2011;59(5):672-5