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, Inhaltsverzeichnis

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

Authors

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

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

Volltext

Referenzen

References
1 Ge HM, Chen X, Wang XT, Huang B, Tan RX. Hopeanol: a potent cytotoxin with a novel skeleton from Hopea exalata . Eur J Org Chem 2006; 2006: 5551-5554
2 Zgoda-Pols JR, Freyer AJ, Killmer LB, Porter JR. Antimicrobial resveratrol tetramers from the stem bark of Vatica oblongifolia ssp. oblongifolia . J Nat Prod 2002; 65: 1554-1559
3 Ito T, Tanaka T, Iinuma M, Nakaya K, Takahashi Y, Sawa R, Naganawa H, Chelladurai V. Two new oligostilbenes with dihydrobenzofuran from the stem bark of Vateria indica . Tetrahedron 2003; 59: 1255-1264
4 Huang KS, Lin M, Yu LN, Kong M. Four novel oligostilbenes from the roots of Vitis amurensis . Tetrahedron 2000; 56: 1321-1329
5 Ge HM, Yang WH, Zhang J, Tan RX. Antioxidant oligostilbenoids from the stem wood of Hopea hainanensis . J Agric Food Chem 2009; 57: 5756-5761
6 Ge HM, Yang WH, Shen Y, Jiang N, Guo ZK, Luo Q, Xu Q, Ma J, Tan RX. Immunosuppressive resveratrol aneuploids from Hopea chinensis. Chem Eur J 2010; 16: 6338-6345
7 Dai JR, Hallock YF, Cardellina JH, Boyd MR. HIV-inhibitory and cytotoxic oligostilbenes from the leaves of Hopea malibato . J Nat Prod 1998; 61: 351-353
8 Yan T, Wang T, Wei W, Jiang N, Qin YH, Tan RX, Ge HM. Polyphenolic acetylcholinesterase inhibitors from Hopea chinensis . Planta Med 2012; 78: 1015-1019
9 Qin YH, Zhang J, Cui JT, Guo ZK, Jiang N, Tan RX, Ge HM. Oligostilbenes from Vatica mangachapoi with xanthine oxidase and acetylcholinesterase inhibitory activities. RSC Adv 2011; 1: 135-141
10 Ge HM, Sun H, Jiang N, Qin YH, Dou H, Yan T, Hou YY, Griesigner C, Tan RX. Relative and absolute configuration of vatiparol (1 mg): a novel anti-inflammatory polyphenol. Chem Eur J 2012; 18: 5213-5221
11 Ge HM, Zhu CH, Shi DH, Zhang LD, Xie DQ, Yang J, Ng SW, Tan RX. Hopeahainol A: an acetylcholinesterase inhibitor from Hopea hainanensis . Chem Eur J 2008; 14: 376-381
12 Tanaka T, Ito T, Ido Y, Nakaya K, Iinuma M, Chelladurai V. Hopeafuran and a C-glucosyl resveratrol isolated from stem wood of Hopea utilis . Chem Pharm Bull 2001; 49: 785-787
13 Liu JY, Ye YH, Wang L, Shi DH, Tan RX. New resveratrol oligomers from the stem bark of Hopea hainanensis . Helv Chim Acta 2005; 11: 2910-2917
14 Naohito A, Tetsuro I, Kenji O, Minori N, Yuichi M, Masayoshi O, Yoshinori N, Masafumi I, Munekazu I. Resveratrol oligomers from Vatica albiramis . J Nat Prod 2010; 73: 1499-1506
15 Ito T, Ali Z, Tanaka T, Nakaya K, Murata J, Darnaedi D, Iinuma M. Stilbenoids with one epoxy group from Cotylelobium lanceolatum. Heterocycles 2006; 68: 1617-1630
16 Ito T, Tanaka T, Ido Y, Nakaya K, Iinuma M, Takahashi Y, Naganawa H, Riswan S. Five new oligostilbenes with one or two dihydrofurans from the stem bark of Vatica rassak . Heterocycles 2001; 55: 557-566
17 Ellman GL, Courtney KD, Andres V, Featherstone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961; 7: 88-95

Zusatzmaterial

Supporting Information (PDF)