Oligostilbenoids with Acetylcholinesterase Inhibitory Activity from Dipterocarpus alatus

Chao Jun Chen; Rong Jiang; Gang Wang; Rui Hua Jiao; Chompoonuch Tancharoen; Kanokorn Sudto; Sranya Vajarothai; Supa Hannongbua; Hui Ming Ge; Ren Xiang Tan

doi:10.1055/s-0034-1383194

Planta Medica, Table of Contents

Planta Med 2014; 80(17): 1641-1646
DOI: 10.1055/s-0034-1383194

Natural Product Chemistry

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Oligostilbenoids with Acetylcholinesterase Inhibitory Activity from Dipterocarpus alatus

Chao Jun Chen

¹Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, China

,

Rong Jiang

¹Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, China

,

Gang Wang

¹Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, China

,

Rui Hua Jiao

¹Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, China

,

Chompoonuch Tancharoen

²Department of Chemistry, Faculty of Science, Kasetsart University and Center of Nanotechnology, Kasetsart University, Bangkok, Thailand

,

Kanokorn Sudto

³Interdisciplinary Graduate Program in Genetic Engineering, The Graduate School, Kasetsart University, Bangkok, Thailand

,

Sranya Vajarothai

⁴Department of Botany, Faculty of Science, Kasetsart University, Bangkok, Thailand

,

Supa Hannongbua

²Department of Chemistry, Faculty of Science, Kasetsart University and Center of Nanotechnology, Kasetsart University, Bangkok, Thailand

,

Hui Ming Ge

¹Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, China

,

Ren Xiang Tan

¹Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, China

› Author Affiliations

Abstract

Phytochemical investigation of the stem wood of Dipterocarpus alatus led to the isolation and characterization of four new oligostilbenoids, dipterocarpols A–D (1–4), together with two known resveratrol oligomers, hopeahainol (5) and hopeafuran (6). The structures of the new compounds were determined by comprehensive spectral analysis including 1D and 2D NMR, and high-resolution MS. The absolute configurations were determined by NOESY and CD spectra. Dipterocarpol A (1) and hopeahainol A (5) showed moderate acetylcholinesterase inhibitory activity with IC₅₀ values of 8.28 µM and 11.28 µM, respectively. Furthermore, the discovery of compound 3 gave the first evidence that the biosynthetic origin of resveratrol aneuploids is related to the loss of a half resveratrol unit by oxidative cleavage.

Key words

Dipterocarpus alatus - Dipterocarpaceae - oligostilbenoids - acetylcholinesterase inhibitory activity

Full Text

References

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