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      Lycodine-Type Alkaloids from Lycopodiastrum casuarinoides and Their Acetylcholinesterase Inhibitory Activity

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          Abstract

          Four new lycodine-type alkaloids, namely 16-hydroxyhuperzine B ( 1), N-methyl-11-acetoxyhuperzine B ( 2), 8,15-dihydrolycoparin A ( 3) and (7 S, 12 S, 13 R)-huperzine D-16- O-β- d-glucopyranoside ( 4), along with ten known analogues 5− 14, were isolated from the whole plant of Lycopodiastrum casuarinoides. The structures of the new compounds were elucidated by means of spectroscopic techniques (IR, MS, NMR, and CD) and chemical methods. Compounds 1 and 2 possessed four connected six-membered rings, while compounds 3 and 4 were piperidine ring cleavage products. In particular, compound 4 was a lycopodium alkaloidal glycoside which is reported for the first time. Among the isolated compounds N-demethylhuperzinine ( 7), huperzine C ( 8), huperzine B ( 9) and lycoparin C ( 13) possessed significant inhibitory activity against acetylcholinesterase, and the new compound 1 showed moderate inhibitory activity. The structure activity relationships were discussed.

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          The Lycopodium alkaloids.

          David R. Gang, Xiaoqiang Ma (2004)
          Lycopodium alkaloids are quinolizine, or pyridine and alpha-pyridone type alkaloids. Some Lycopodium alkaloids are potent inhibitors of acetylcholinesterase (AChE). Huperzine A (HupA) is reported to increase efficiency for learning and memory in animals, and it shows promise in the treatment of Alzheimer's disease (AD). 201 Lycopodium alkaloids from 54 species of Lycopodium (sensu lato) have been reported so far. This review is intended to to cover the chemical, pharmacological and clinical research on Lycopodium alkaloids reported in the literature from the spring of 1993 to August 2004. Structures of 81 new Lycopodium alkaloids are presented, classified and analyzed. The structural characters and biogenetic relationships of the four major Lycopodium alkaloid groups (lycopodine, lycodine, fawcettimine and miscellaneous) are discussed. Bioactivities of Lycopodium alkaloids, especially HupA, are summarized. In particular, the effect of HupA and other cholinesterase inhibitors (anti-AD drugs) on acetylcholine esterase (AChE) activity in the rat cortex and butylcholine esterase activity are compared. Structure-activity relationships and structure modifications of HupA and its analogs are described. Information on clinical trials with HupA and its derivative ZT-1 is presented. The state of HupA availability and recent advances in in vitro propagation of HupA producing plants are outlined. Finally, hypotheses about Lycopodium alkaloid biosynthetic pathways are discussed.
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            Acetylcholinesterase and butyrylcholinesterase inhibitory activity of some Turkish medicinal plants.

            B. Sener, M Choudhary, I Orhan … (2004)
            The chloroform:medianol (1:1) extracts of a number of the plant species belonging to eight families, namely Corydalis solida (L.) Swartz subsp. solida and Glaucium corniculatum (L.) J. H. Rudolph (Papaveraceae), Rhododendron ponticum L. subsp. ponticum and Rhododendron luteum Sweet. (Ericaceae), Buxus sempervirens L. (Buxaceae), Vicia faba L. (Fabaceae), Robinia pseudoacacia L. (Caeselpiniaceae), Tribulus terrestris L. and Zygophyllum fabago L. (Zygophyllaceae), Lycopodium clavatum L. (Lycopodiaceae), Fumaria vaillantii Lois., Fumaria capreolata L., Fumaria kralikii Jordan, Fumaria asepala Boiss., Fumaria densiflora DC., Fumaria flabellata L., Fumaria petteri Reichb. subsp. thuretii (Boiss.) Pugsley, Fumaria macrocarpa Boiss. ex Hausskn., Fumaria cilicica Hauskkn., Fumaria parviflora Lam. and Fumaria judaica Boiss. (Fumariaceae) were screened for their anticholinesterase activity on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes by in vitro Ellman method at 10 microg/ml and 1 mg/ml concentrations. The extracts did not show any noticeable inhibitory activity against both of the enzymes at 10 microg/ml. The extracts of Rhododendron ponticum subsp. ponticum, Rhododendron luteum, Corydalis solida subsp. solida, Glaucium corniculatum, and Buxus sempervirens showed remarkable inhibitory activity above 50% inhibition rate on AChE at 1 mg/ml. Among them, Rhododendron ponticum subsp. ponticum, Corydalis solida subsp. solida and Buxus sempervirens were the most active extracts against BChE having 95.46 +/- 1.03%, 93.08 +/- 0.97%, and 93.45 +/- 0.88% inhibition rates, respectively. Among the extracts screened, all of the Fumaria extracts displayed highly potent inhibition against both of the enzymes at 1 mg/ml concentration compared to the standard.
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              Current drug targets for Alzheimer's disease treatment

              Debomoy Lahiri, Nigel Greig, Kumar Sambamurti … (2002)
              Article 0 comments Cited 29 times – based on 0 reviews     Review now
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                Author and article information

                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 10 July 2014
                Publication date Collection: July 2014
                Volume: 19
                Issue: 7
                Pages: 9999-10010
                Affiliations
                [1 ]State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China
                [2 ]School of Biotechnology and Chemical Engineering, Ningbo Institute of Technology, Zhejiang University; Ningbo 315100, China
                Author notes
                [* ]Authors to whom correspondence should be addressed; E-Mails: chenjj@ 123456lzu.edu.cn (J.-J.C.); npchem@ 123456lzu.edu.cn (K.G.); Tel.: +86-931-891-2592 (K.G.); Fax: +86-931-891-2582 (K.G.).
                Article
                Publisher ID: molecules-19-09999
                DOI: 10.3390/molecules19079999
                PMC ID: 6271639
                PubMed ID: 25014530
                SO-VID: c2be7fb0-567b-4db8-bc0e-007b302e118e
                Copyright © © 2014 by the authors.
                License:

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/4.0/).

                History
                Date received : 23 May 2014
                Date revision received : 18 June 2014
                Date accepted : 27 June 2014
                Categories
                Subject: Article

                Keywords: lycopodiastrum casuarinoides,lycopodiaceae,lycodine alkaloid,acetylcholinesterase,16-hydroxyhuperzine b,n-methyl-11-acetoxyhuperzine b,8,15-dihydrolycoparin a,(7s, 12s, 13r)-huperzine d-16-o-β-d-glucopyranoside
                Data availability:
                Keywords: lycopodiastrum casuarinoides, lycopodiaceae, lycodine alkaloid, acetylcholinesterase, 16-hydroxyhuperzine b, n-methyl-11-acetoxyhuperzine b, 8,15-dihydrolycoparin a, (7s, 12s, 13r)-huperzine d-16-o-β-d-glucopyranoside

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