Planta Med 2010; 76(15): 1762-1764
DOI: 10.1055/s-0030-1249814
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Alkaloids from Roots of Stephania rotunda and Their Cholinesterase Inhibitory Activity

Tran Manh Hung1 , Nguyen Hai Dang2 , Jin Cheol Kim3 , Han-Su Jang4 , Sung-Woo Ryoo5 , Jeong Hyung Lee5 , Jae Sue Choi6 , KiHwan Bae7 , Byung Sun Min1
  • 1College of Pharmacy, Catholic University of Daegu, Gyeongbuk, Korea
  • 2Institute of Natural Product Chemistry, Vietnamese Academy of Science and Technology, Hanoi, Vietnam
  • 3Korea Research Institute of Chemical Technology, Daejeon, Korea
  • 4Gyeongbuk Institute for Bio Industry, Gyeongbuk, Korea
  • 5College of Natural Sciences, Kangwon National University, Kangwon, Korea
  • 6Faculty of Food Science and Biotechnolgy, Pukyoung National University, Busan, Korea
  • 7College of Pharmacy, Chungnam National University, Daejeon, Korea
Further Information

Publication History

received July 13, 2009 revised March 8, 2010

accepted March 15, 2010

Publication Date:
13 April 2010 (online)

Abstract

In the course of screening plants used in folk medicine as memory enhancers, a 70 % ethanolic extract of Stephania rotunda roots showed significant AChE inhibitory activity. Repeated column chromatography led to the isolation of a new protoberberine alkaloid, which we named stepharotudine (1), and seven known compounds (28). The chemical structures of the isolated compounds were elucidated based on extensive 1D and 2D NMR spectroscopic data. Compounds 18 were investigated in vitro for their anticholinesterase activity using a rat cortex AChE enzyme.

References

  • 1 Becker R, Giacobini E, Elble R, McIlhany M, Sherman K. Potential pharmacotherapy of Alzheimer disease. A comparison of various forms of physostigmine administration.  Acta Neurol Scand. 1988;  116 (Suppl.) 19-32
  • 2 Giacobini E. Cholinestrases and cholinesterase inhibitors. Cholinesterase inhibitors: from the calabar bean to Alzheimer therapy. London; Martin Dunitz, Ltd. 2000: 181-226
  • 3 Oh M H, Houghton P J, Whang W K, Cho J H. Screening of Korean herbal medicines used to improve cognitive function for anti-cholinesterase activity.  Phytomedicine. 2004;  11 544-548
  • 4 Houghton P J, Ren Y, Howes M J. Acetylcholinesterase inhibitors from plants and fungi.  Nat Prod Rep. 2006;  23 181-189
  • 5 Dy Phon P. Dictionnaire des plantes utilisées au Cambodge. Phnom Penh; Olympic 2000: 915
  • 6 Perry L M. Medicinal plants of East and Southeast Asia. Cambridge; MIT Press 1980: 620
  • 7 Chea A, Hout S, Bun S S, Tabatadze N, Gasquet M, Azas N, Elias R, Balansard G. Antimalarial activity of alkaloids isolated from Stephania rotunda.  J Ethnopharmacol. 2007;  112 132-137
  • 8 Hout S, Chea A, Bun S S, Elias R, Gasquet M, Timon-David P, Balansard G, Azas N. Screening of selected indigenous plants of Cambodia for antiplasmodial activity.  J Ethnopharmacol. 2006;  107 12-18
  • 9 Matsuno T. Alkaloids of Menispermaceae plants. LXXIII. Rotundine, an alkaloid of Stephania rotunda, 2.  Yakugaku Zasshi. 1944;  64 52-53
  • 10 Tomita M, Kozuka M. Alkaloids of menispermaceous plants. CCXXVII. Alkaloids of Stephania rotunda.  Yakugaku Zasshi. 1966;  86 871-873
  • 11 Kozuka M, Miyaji K, Sawada T, Tomita M. Studies on the alkaloids of menispermaceous plants. Part 283. A major alkaloid of the leaves and stems of Stephania rotunda.  J Nat Prod. 1985;  48 341-342
  • 12 Luger P, Weber M, Dung N X, Moi L D, Khoi T T, Phuong D L. (±)-Tetrahydropalmatine monohydrate.  Acta Crystallogr C. 1998;  54 1977-1980
  • 13 Nguyen T V, Pham T K, Bui K L, Chu D K. Cycleanine, a new alkaloid extracted from tuber Stephania rotunda from Vietnam.  Tap Chi Duoc Hoc. 1999;  3 7-9
  • 14 Thuy T T, Porzel A, Franke K, Wessjohann L, Sung T V. Isoquinolone and protoberberine alkaloids from Stephania rotunda.  Pharmazie. 2005;  60 701-704
  • 15 Thuy T T, Sung T V, Franke K, Wessjonann L. Morphinane and oxoaporphine alkaloids from Stephania rotunda Lour.  J Chem. 2006;  44 110-114
  • 16 Thuy T T, Franke K, Porzel A, Wessjohann L, Sung T V. Quaternary protoberberine alkaloids from Stephania rotunda.  J Chem. 2006;  44 259-264
  • 17 Bun S S, Laget M, Chea A, Bun H, Ollivier E, Elias R. Cytotoxic activity of alkaloids isolated from Stephania rotunda.  Phytother Res. 2009;  23 587-590
  • 18 Chang J K, Chang N C. Total synthesis of (+)-gusanlung D.  Tetrahedron. 2008;  64 3483-3487
  • 19 Zhang J S, Le Men-Olivier L, Massiot G. Isoquinoline alkaloids from Acangelisia gusanlung.  Phytochemistry. 1995;  39 439
  • 20 Zhao Q, Tang X C. Effects of huperzine A on acetylcholinesterase isoforms in vitro: comparison with tacrine, donepezil, rivastigmine and physostigmine.  Eur J Pharmacol. 2002;  455 101-107
  • 21 Ellman G L, Courtney K D, Andres Jr V, Featherstone R M. A new and rapid colorimetric determination of acetylcholinesterase activity.  Biochem Pharmacol. 1961;  7 88-90
  • 22 Giacobini E. The cholinergic system in Alzheimer disease.  Prog Brain Res. 1990;  84 321-332
  • 23 LeDoux J E. Emotional memory systems in the brain.  Behav Brain Res. 1993;  58 69-79
  • 24 Ito C, Mizuno T, Wu T S, Furukawa H. Alkaloids from Corydalis.  Phytochemistry. 1990;  29 2044-2045
  • 25 Kuznetsova L P, Nikol'skaia E B, Sochilina E E, Faddeeva M D. Inhibition by various alkaloids of acetylcholinesterase and butyrylcholinesterase from human blood.  J Evol Biochem Physiol. 2002;  38 28-31
  • 26 Kim S R, Hwang S Y, Jang Y P, Park M J, Markelonis G J, Oh T H, Kim J C. Protopine from Corydalis ternata has anticholinesterase and antiamnesic activities.  Planta Med. 1999;  65 218-221
  • 27 Adsersen A, Kjølbye A, Dall O, Jäger A K. Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Corydalis cava Schweigg. & Kort.  J Ethnopharmacol. 2007;  113 179-182
  • 28 Hung T M, Na M, Dat N T, Ngoc T M, Youn U, Kim H J, Min B S, Bae K. Cholinesterase inhibitory and anti-amnesic activity of alkaloids from Corydalis turtschaninovii.  J Ethnopharmacol. 2008;  119 74-80
  • 29 Hung T M, Ngoc T M, Youn U J, Min B S, Na M, Thuong P T, Bae K. Anti-amnestic activity of pseudocoptisine from Corydalis Tuber.  Biol Pharm Bull. 2008;  31 159-162
  • 30 Broadwell R D, Sofroniew M V. Serum proteins bypass the blood-brain fluid barriers for extracellular entry to the central nervous system.  Exp Neurol. 1993;  120 245-263

Prof. Byung Sun Min

College of Pharmacy
Catholic University of Daegu

330 Geumnak 1-ri

Gyeongbuk 712–702

Korea

Phone: + 82 5 38 50 36 13

Fax: + 82 5 38 50 36 02

Email: bsmin@cu.ac.kr

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