Oligostilbenoids with Acetylcholinesterase Inhibitory Activity from Dipterocarpus alatus

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

• 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