Pycnalin, a new α-glucosidase inhibitor from Acer pycnanthum

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

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)672-675
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume59
Issue number5
DOIs
Publication statusPublished - 2011 May
Externally publishedYes

Fingerprint

Acer
Glucosidases
Gallic Acid
Scavenging
Free Radicals
Nuclear magnetic resonance
pycnalin
ginnalin A
1,5-anhydroglucitol

Keywords

  • α-glucosidase inhibition
  • 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity
  • Acer pycnanthum
  • Ginnalin
  • Pycnalin

ASJC Scopus subject areas

  • Drug Discovery
  • Chemistry(all)

Cite this

Ogawa, A., Miyamae, Y., Honma, A., Koyama, T., Yazawa, K., & Shigemori, H. (2011). Pycnalin, a new α-glucosidase inhibitor from Acer pycnanthum. Chemical and Pharmaceutical Bulletin, 59(5), 672-675. https://doi.org/10.1248/cpb.59.672

Pycnalin, a new α-glucosidase inhibitor from Acer pycnanthum. / Ogawa, Ai; Miyamae, Yusaku; Honma, Atsushi; Koyama, Tomoyuki; Yazawa, Kazunaga; Shigemori, Hideyuki.

In: Chemical and Pharmaceutical Bulletin, Vol. 59, No. 5, 05.2011, p. 672-675.

Research output: Contribution to journalArticle

Ogawa, A, Miyamae, Y, Honma, A, Koyama, T, Yazawa, K & Shigemori, H 2011, 'Pycnalin, a new α-glucosidase inhibitor from Acer pycnanthum', Chemical and Pharmaceutical Bulletin, vol. 59, no. 5, pp. 672-675. https://doi.org/10.1248/cpb.59.672
Ogawa A, Miyamae Y, Honma A, Koyama T, Yazawa K, Shigemori H. Pycnalin, a new α-glucosidase inhibitor from Acer pycnanthum. Chemical and Pharmaceutical Bulletin. 2011 May;59(5):672-675. https://doi.org/10.1248/cpb.59.672
Ogawa, Ai ; Miyamae, Yusaku ; Honma, Atsushi ; Koyama, Tomoyuki ; Yazawa, Kazunaga ; Shigemori, Hideyuki. / Pycnalin, a new α-glucosidase inhibitor from Acer pycnanthum. In: Chemical and Pharmaceutical Bulletin. 2011 ; Vol. 59, No. 5. pp. 672-675.
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