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Cited by 148Synthesis and bioactivity of alkaloidsAlkaloids: synthesis and pharmacologyPhytochemistry and Biological Activities

Banisteriopsis caapi, a unique combination of MAO inhibitory and antioxidative constituents for the activities relevant to neurodegenerative disorders and Parkinson's disease

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Samoylenko, Volodymyr, Rahman, Md. Mostafizur, Tekwani, Babu L., Tripathi, Lalit M., Wang, Yan-Hong, Khan, Shabana I., Khan, Ikhlas A., Miller, Loren S. +2 more·2010·Journal of Ethnopharmacology
DOI 10.1016/j.jep.2009.10.030PMC PMC2828149
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Abstract

Aim of the study Parkinson's disease is a neurological disorder mostly effecting the elder population of the world. Currently there is no definitive treatment or cure for this disease. Therefore, in this study the composition and constituents of the aqueous extract of Banisteriopsis caapi for monoamine oxidases (MAO) inhibitory and antioxidant activities were assessed, which are relevant to the prevention of neurological disorders, including Parkinsonism. Materials and methods The aqueous extract of Banisteriopsis caapi stems was standardized and then fractionated using reversed-phase (RP) chromatography. Pure compounds were isolated either by reversed-phase (RP) chromatography or centrifugal preparative TLC, using a Chromatotron. Structure elucidation was carried out by 1D and 2D NMR, Mass, IR and Circular Dichroism spectroscopy and chemical derivatization. Chemical profiling of the extract was carried out with RP-HPLC. The inhibitory activity of MAO-A, MAO-B, acetylcholinesterase, butyrylcholinesterase and catechol-O-methyl transferase enzymes, as well as antioxidant and cytotoxic activities of both Banisteriopsis caapi extract and isolated compounds was evaluated. Results An examination of the aqueous extracts of Banisteriopsis caapi cultivar Da Vine yielded two new alkaloidal glycosides, named banistenoside A (1) and banistenoside B (2), containing "azepino[1,2-a]tetrahydro-beta-carboline" unique carbon framework. One additional new natural tetrahydronorharmine (4), four known beta-carbolines harmol (3), tetrahydroharmine (5), harmaline (6) and harmine (7), two known proanthocyanidines (-)-epicatechin (8) and (-)-procyanidin B2 (9), and a new disaccharide beta-d-fructofuranosyl-(2-->5)-fructopyranose (14) together with known sacharose (15) and beta-d-glucose (16) were also isolated. In addition, the acetates of 1, 2, 8, 9, 14 and 15 (compounds 10-13, 17, 18) were also prepared. Harmaline (6) and harmine (7) showed potent in vitro inhibitory activity against recombinant human brain monoamine oxidase (MAO)-A and -B enzymes (IC(50) 2.5 and 2.0 nM, and 25 and 20 microM, respectively), and (-)-epicatechin (8) and (-)-procyanidin B2 (9) showed potent antioxidant and moderate MAO-B inhibitory activities (IC(50)<0.13 and 0.57 microg/mL, and 65 and 35 microM). HPLC analysis revealed that most of the dominant chemical and bioactive markers (1, 2, 5, 7-9) were present in high concentrations in dried bark of large branch. Analysis of regular/commercial Banisteriopsis caapi dried stems showed a similar qualitative HPLC pattern, but relatively low content of dominant markers 1, 2, 7, and 9, which led to decreased MAO inhibitory and antioxidant potency. Conclusion Collectively, these results give additional basis to the existing claim of Banisteriopsis caapi stem extract for the treatment of Parkinsonism, including other neurodegenerative disorders.

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  • Banisteriopsis caapi supplies various β-carboline alkaloids (harmine, tetrahydroharmine, and harmaline) that act as reversible inhibitors of MAO type A (IC50 2 nM).

    “However, Banisteriopsis caapi supplies various β-carboline alkaloids (harmine (44), tetrahydroharmine (45), and harmaline (46)) that act as reversible inhibitors of MAO type A (IC50 2 nM [129]).”

    From Molecular and Functional Imaging Studies of Psychedelic Drug Action in Animals and Humans. (2021) · cites this paper as [129]

    The Introduction identifies harmine, harmaline and tetrahydroharmine as β-carbolines found in B. caapi. Section 3.2 reports MAO-A IC50 values of 2.0 nM for harmine and 2.5 nM for harmaline, but says tetrahydroharmine is much weaker. The passages do not establish that their inhibition is reversible, and the 2 nM value does not apply to all three. (LLM, conf=0.90)

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Research works printed but not linked: 29

  1. Atta-ur-Rehman Tayyaba B Imine-enamine tautomerism in harmaline Pakistan Journal of Scientific and Industrial Research 1972 15 9 10
  2. Baddeley TC Howie RA Skakle JMS Wardell JL 1,2,3,4-Tetra-O-acetyl-beta-D-glucopyranuronic acid monohydrate at 120 K and anhydrous 1,2,3,4-tetra-O-acetyl-beta-D-glucopyranose at 292 K Acta Crystallographica, Section C: Crystal Structure Communications C61 2005 o711 o714 16330855
  3. Barrett MW Klyne W Scopes PM Fletcher AC Porter LJ Haslam E Plant proanthocyanidines Part 6. Chiroptical studies. Part 95. Circular dichroism of procyanidines Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry 1979 2375 2377
  4. Borenfreund E Babich H Martin-Alguacil N Rapid chemosensitivity assay with human normal and tumor cells in vitro. In vitro cellular and developmental biology Journal of the Tissue Culture Association 1990 26 1030 1034 2177465
  5. Brown RT Fraser SB Anthocephalus alkaloids: cadambine and 3α-dihydrocadambine Tetrahedron Letters 1974 23 1957 1959
  6. Callaway JC Brito GS Neves ES Phytochemical analyses of Banisteriopsis caapi and Psychotria viridis Journal of psychoactive drugs 2005 37 145 150 16149327
  7. Cho ES Lee KW Lee HJ Cocoa procyanidins protect PC12 cells from hydrogen-peroxide-induced apoptosis by inhibiting activation of p38 MAPK and JNK Mutation Research, Fundamental and Molecular Mechanisms of Mutagenesis 2008 640 1–2 123 130 18272186
  8. Ellman GL Courtney KD Andres V Jr Featherstone RM A new and rapid colorimetric determination of acetylcholinesterase activity Biochemical Pharmacology 1961 7 88 95 13726518
  9. Heo HJ Lee CY Epicatechin and catechin in cocoa inhibit amyloid β-protein induced apoatosis Journal of Agricultural and Food Chemistry 2005 53 5 1445 1448 15740021
  10. Hochstein FA Paradies AM Alkaloids of Banisteria caapi and Prestonia amazonicum Journal of the American Chemical Society 1957 79 5735
  11. Hou WC Lin RD Chen CT Lee MH Monoamine oxidase B (MAO-B) inhibition by active principles from Uncaria rhynchophylla Journal of Ethnopharmacology 2005 100 216 220 15890481
  12. Kawanishi K Uhara Y Hashimoto Y Shihunine and dihydroshihunine from Banisteriopsis caapi Journal of Natural Products 1982 45 637 639
  13. Khokhar S Venema D Hollman PC Dekker M Jongen W A RP-HPLC method for the determination of tea catechins Cancer Letters 1997 114 171 172 9103282
  14. Learmonth DA Palma PN Vieira-Coelho MA Soares-da-Silva P Synthesis, biological evaluation and molecular modeling of a novel, peripherally selective inhibitor catechol-O-methyltransferase Journal of Medicinal Chemistry 2004 47 6207 6217 15566291
  15. Lee CM Trager WF Beckett AH Corynantheidine-type alkaloids. II. Absolute configuration of mitragynine, speciociliatine, mitraciliatine and speciogynine Tetrahedron 1967 23 375 385 6037287
  16. Mabberley DJ The Plant Book A Portable Dictionary of the Higher Plants 1997 Second Edition Cambridge Cambridge Univ. Press 858
  17. Pahkla R Harro J Rago L Behavioural effects of pinoline in rat forced swimming, open field and elevated plus-maze test Pharmacological Research 1996 34 73 78 8981559
  18. Rosenkranz AR Schmaldienst S Stuhlmeier KM Chen W Knapp W Zlabinger GJ A microplate assay for the detection of oxidative products using 2’, 7’-dichloroflurescin-diacetate Journal of Immunological Methods 1992 156 39 45 1431161
  19. Rothchild R Proton and carbon-13 NMR studies of some tryptamines, precursors, and derivatives: Ab initio calculations for optimized structures Spectroscopy letters 2005 38 521 537
  20. Sánchez-Ramos JR Banisterine and Parkinsons disease Clinical Neuropharmacol 1991 14 391 402 1742748
  21. Schultes RE The Botanical and Chemical Distribution of Hallucinogens Annual Review of Plant Physiology 1970 21 571 598
  22. Schultes RE Hofmann A Plants of the Gods Their Sacred, Healing and Hallucinogenic Powers 1992 Rochester, VT Healing Arts Press 124 135
  23. Schultes RE Raffauf RF Vine of the Soul: Medicine Men, Their Plants and Rituals in the Colombian Amazon 1992 Oracle, AZ Synergetic Press
  24. Schultes RE Siri von Reis Ethnobotany, Evolution of a Discipline 1995 Portland, OR Dioscorides Press
  25. Schwarz MJ Houghton PJ Rose S Jenner P Lees AD Activities of extract and constituents of Banisteriopsis caapi relevant to Parkinsonism Pharmacology, Biochemistry and Behavior 2003 75 627 633 12895680
  26. Scudiero DA Shoemaker RH Paull KD Monks A Tierney S Nofziger TH Evalualtion of a soluble tetrazolium/ formazan assay for cell growth and drug sensitivity in culture using human and other cell lines Cancer Research 1988 48 4827 4833 3409223
  27. Serrano-Dueñas M Cardozo-Pelaez F Sanchez-Ramos JR Effects of Banisteriopsis caapi extract on Parkinson’s disease The Scientific Review of Alternative Medicine 2001 5 127 132
  28. Szabó LF Rigorous biogenetic network for a group of indole alkaloids derived from strictosidine Molecules 2008 13 1875 1896 PMC6245392 18794791
  29. Timmermans JW Slaghek TM Lizuka M Van den Ende W De Roover J Van Laere A Isolation and structural analysis of new fructans produced by chicory Journal of Carbohydrate Chemistry 2001 20 375 395

Cited by

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Authors
Samoylenko, V., Rahman, M. M., Tekwani, B. L., Tripathi, L. M., Wang, Y.-H., Khan, S. I., Khan, I. A., Miller, L. S., Joshi, V. C., & Muhammad, I.
Affiliations
University of Mississippi (US)
Corresponding author
Muhammad, Ilias
ORCID
Venue
Journal of Ethnopharmacology
Publisher
Elsevier BV
Published
2010-02
Volume
127
Issue
2
Pages
357-367
ISSN
0378-8741 (ISSN-L)
DOI
10.1016/j.jep.2009.10.030
PMC
PMC2828149
OpenAlex
W2048857700
Cited by
148
References
1
Citations by year
2026: 8 · 2025: 4 · 2024: 7 · 2023: 14 · 2022: 13 · 2021: 12 · 2020: 16 · 2019: 8 · 2018: 12 · 2017: 6 · 2016: 12 · 2015: 6 · 2014: 6 · 2013: 8 · 2012: 10
FWCI
2.00
Type
journal article
Language
en
Open access
Licence
www.elsevier.com/tdm/userlicense/1.0/ (tdm)
Locations
  • Journal of Ethnopharmacology (publishedVersion)
  • PubMed (publishedVersion)
  • PubMed Central (acceptedVersion)
Funders
  • National Institutes of Health (5r21at003409-02)
  • National Center for Complementary and Alternative Medicine
  • National Center for Complementary and Integrative Health (R21 AT003409, 5R21AT003409-02)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Synthesis and bioactivity of alkaloids
  • Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Alkaloids: synthesis and pharmacology
  • Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry and Biological Activities
Keywords
Banisteriopsis caapi, monoamine oxidase inhibition, antioxidant activity, Parkinson's disease, neurodegenerative diseases, harmine, harmaline, harmol, tetrahydroharmine, β-carbolines, proanthocyanidins, catechol-O-methyltransferase inhibition, acetylcholinesterase inhibition, butyrylcholinesterase inhibition, cytotoxicity, aqueous stem extract
MeSH terms
Animals, Antioxidants, Chlorocebus aethiops, Humans, Monoamine Oxidase Inhibitors, Parkinson Disease, Plant Extracts, Swine, Vero Cells, LLC-PK1 Cells, Plant Leaves, Plant Stems, Neurodegenerative Diseases, Banisteriopsis, Plant Components, Aerial, Cell Line, Tumor

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