Planta Med 2012; 78(10): 1015-1019
DOI: 10.1055/s-0031-1298623
Natural Product Chemistry
Letters
Georg Thieme Verlag KG Stuttgart · New York

Polyphenolic Acetylcholinesterase Inhibitors from Hopea chinensis

Tong Yan
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, China
,
Ting Wang
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, China
,
Wei Wei
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, China
,
Nan Jiang
2   School of Pharmacy, Nanjing Medical University, Nanjing, China
,
Yan Hua Qin
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, China
,
Ren Xiang Tan
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, China
,
Hui Ming Ge
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, China
› Author Affiliations
Further Information

Publication History

received 02 December 2011
revised 17 April 2012

accepted 07 May 2012

Publication Date:
24 May 2012 (online)

Abstract

Bioassay-guided investigation of the stem bark of Hopea chinensis led to the isolation of two new polyphenols, hopeachinols C (1) and D (2), together with ten known compounds (312). Compounds 1 and 2 were determined by extensive analysis of spectroscopic data and computational methods. All of these phytochemicals were tested for acetylcholinesterase inhibitory activity, and five resveratrol-derived compounds (1 and 710) exhibited significant activity with their IC50 values ranging from 4.81 to 11.71 µM.

Supporting Information

 
  • References

  • 1 Whitehouse PJ, Price DL, Struble RG, Clarke AW, Coyle JT, DeLong MR. Alzheimers-disease and senile dementia – loss of neurons in the basal forebrain. Science 1982; 215: 1237-1239
  • 2 Davis KL, Mohs RC. Enhancement of memory processes in Alzheimers-disease with mulitiple-dose intravenous physostigmine. Am J Psychiatry 1982; 139: 1421-1424
  • 3 Thal LJ, Fuld PA, Masur DM, Sharpless NS. Oral physostigmine and lecithin improve memory in Alzheimer-disease. Ann Neurol 1983; 13: 491-496
  • 4 Ha GT, Wong RK, Zhang Y. Huperzine A as potential treatment of Alzheimerʼs disease: an assessment on chemistry, pharmacology, and clinical studies. Chem Biodivers 2011; 8: 1189-1204
  • 5 Ge HM, Zhu CH, Shi DH, Zhang LD, Xie DQ, Yang J, Ng SW, Tan RX. Hoeahainol A: an acetylcholinesterase inhibitor from Hopea hainanensis . Chem Eur J 2008; 14: 376-381
  • 6 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
  • 7 Tanaka T, Ito T, Nakaya M, Iinuma M, Chelladurai V. Hopeafuran and a C-glucosyl resveratrol isolated from stem wood of Hopea utilis . Chem Pharm Bull 2001; 49: 785-787
  • 8 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
  • 9 Tanaka T, Ito T, Idoa Y, Son TK, Nakaya K, Iinuma M, Ohyama M, Chelladuraic V. Stilbenoids in the stem bark of Hopea parviflora . Phytochemistry 2000; 53: 1015-1019
  • 10 Weber JF, Wahab IA, Marzuki A, Thomas NF, Kadir AA, Hadi AH, Awang K, Latiff AA, Richommee P, Delaunaye J. Heimiol A, a new dimeric stilbenoid from Neobalanocarpus heimii . Tetrahedron Lett 2001; 42: 4895-4897
  • 11 Luo HF, Zhang LP, Hu CQ. Five novel oligostilbenes from the roots of Caragana sinica . Tetrahedron 2001; 57: 4847-4854
  • 12 Kitanaka S, Ikezawa T, Yasukawa K, Yamanouchi S, Takido M, Sung HK, Kim H. (+)-Viniferin, an anti-inflammatory compound from Caragana chamlagu root. Chem Pharm Bull 1990; 38: 432-435
  • 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; 88: 2910-2917
  • 14 Tanaka T, Ito T, Nakaya K, Iinuma M, Takahashi Y, Naganawab H, Riswanc S. Six new heterocyclic stilbene oligomers from stem bark of Shorea hemsleyana . Heterocycles 2001; 55: 729-740
  • 15 Moreno-Labanda JF, Mallavia R, Perez-Fons L, Lizama V, Saura D, Micol V. Determination of piceid and resveratrol in Spanish wines deriving from Monastrell (Vitis vinifera L.) grape variety. J Agric Food Chem 2004; 52: 5396-5403
  • 16 Wang YH, Zhang ZK, He HP, Wang JS, Zhou H, Ding M, Hao XJ. Stilbene C-glucosides from Cissus repens . J Asian Nat Prod Res 2007; 9: 631-636
  • 17 Song S, Li Y, Feng Z, Jiang J, Zhang P. Hepatoprotective constituents from the roots and stems of Erycibe hainanesis . J Nat Prod 2010; 73: 177-184
  • 18 Ito T, Tanaka T, Ido Y, Nakaya K, Iinuma M, Riswan S. Stilbenoids isolated from stem bark of Shorea hemsleyana . Chem Pharm Bull 2000; 48: 1001-1005
  • 19 Zhong XN, Otsuka H, Ide T, Hirata E, Takushi A, Takeda Y. Hydroquinone glycosides from leaves of Mysine seguinii . Phytochemistry 1998; 49: 2149-2153
  • 20 Zhong XN, Otsuka H, Ide T, Hirata E, Takeda Y. Hydroquinone diglycoside acyl esters from the leaves of Myrsine seguinii . Phytochemistry 1999; 52: 923-927
  • 21 Ren Y, Houghton PJ, Hider RC, Howes MJR. Novel diterpenoids acetylcholinesterase inhibitors from Salvia miltiorhiza . Planta Med 2004; 70: 201-204
  • 22 Raves ML, Harel M, Pang YP, Silman I, Kozikowski AP, Sussman JL. Structure of acetylcholinesterase complexed with the nootropic alkaloid, (−)-huperzine A. Nat Struct Biol 1997; 4: 57-63
  • 23 Oritz de Montellano PR, Reich NO. Inhibition of cytochrome P450 enzymes. In: Oritz de Montellano PR, editor Cytochrome P450: structure, mechanism and biodiversity. New York: Plenum Press; 1986: 273-313