1. TAIWO, MICHAEL ADEDAYO 2. IntroductionBanisteriopsis caapi : diagram, general features and taxonomicStudy on Banisteriopsis caapiGeneral features of Banisteriopsis caapiActive compoundsTraditional usesMedical usesExample of studyCritic: Vine of the SoulSearch on databasesStructures of the alkaloidsMechanism of actionPlants Chemically RelatedAdverse effects of Banisteriopsis caapi alkaloidsBiosynthesis of -carboline alkaloidsBibliograhy 3. The Banisteriopsis caapiFlowering Banisteriopsis caapi 4. Taxonomic classification of Banisteriopsis caapi Kingdom: Plantae Order: Malpighiales Family: Malpighiaceae Genus: Banisteriopsis Species: B. caapiCOMMON NAMES: Ayahuasca Vine, Bejuco de Oro,Biaxa, Boa Vine, Caapi, Dapa, Doctor, Kaapi, Kahi,Maridi, Mihi, Natema, Nepe, Pinde, Totenliane, Vineof the Dead, Vine of the Soul, Yage, Yahe, Yaje,Yaxe. 5. There are two scientifically accepted varieties:I. Banisteriopsis caapi var. caupuri with knotty stemsII. Banisteriopsis caapi var. tukunaka with smooth stemsi ii 6. General features of Banisteriopsis caapiBanisteriopsis caapi is a South American shrub of thefamily MalpighiaceaeThe bark is usually chocolate-brown and smooth.Banisteriopsis caapi produces opposite, ovalshaped leaves to 8-20 cm long and 3-9 cm wide.The flowers are pink petalled to 12-14 mm indiameter and 2.5-3 mm long.The Ayahuasca vine's fruit is a nut that grows to5mm long.Banisteriopsis caapi is often propagated throughvegetative cuttings and sometimes by seedglabrous stems 7. Banisteriopis caapi flowers 8. TRADITIONAL USES:Amazonian peoples uses Banisteriopsis caapi, assacramental beverage for its magicalpowers.Surgeries conducted by native healers take placeat night. These healers carefully screen theirprospective patients and will not allow thosesuffering from extreme mental disorders to takepart for fear of disrupting the entire healingsession due to hallucinogenic property of thedrink. 9. In war due to the psychoactive effects of thesenative preparations.Ayahuasca is also used for its curative powers.Hoasa is believed to have been in use since thefirst aborigines in Brazil and prior to the invasionof the Spanish explorers, it was used by shamanfor magic, divination, sorcery and to both detectand treat illnesses. 10. The serious scientific study of ayahuasca began with thefield investigations of the English botanist Richard Sprucethroughout the 1850s. Among the medical uses we can count: Anticanceter(Harmine showed cytotoxicity against HL60 and K562 celllines), psychotherapy, Parkinson's disease, stress, fevers,wounds, it also acts as purgative, and the alkaloids can beused as an MAOI (MonoAmine Oxidase Inhibitor) tofacilitate the ingestion of N,N-Dimetiltryptamine (DMT) andother tryptaminesMedicaluses 11. Active compoundsAlkaloids Harmine, 0.31-8.43% Harmaline, 0.03-0.83% Tetrahydroharmine, 0.05-2.94% (Callaway etal,2005). Others include:Harmilinic acid:7-Methoxy-3,4-dihydro-beta-carboline1-carboxylic acidHarmanamide:1-Carbamoyl-7-methoxy-beta-carbolineAcetylnorharmine: 1-Acetyl-7-methoxy-beta-carbolineHarmalol:1-Methyl-4,9-dihydro-3H-pyrido[3,4-b]indol-7-ol (McKenna, Callaway, & Grb 2007) 12. HarmineHarmalolHarmalineTetrahydroharmineHarmalanThey are reversible inhibitors of MAO-A (RIMA). 13. We now know that the"divinity" resident inspecial plants is chemicalin nature.It is of importance,therefore, to seek outthese primitive races andascertain the plants whichthey have found availablein their economic life, inorder that perchance thevaluable properties theyhave utilized in their wildlife may fill some vacantniche in our own." 14. It is generally accepted that the mainneurobiology mechanism of action ofhallucinogens is acting as agonistis of the 5-HT2A receptors located at the pyramidalglutamatergic neurons of the layer V of theprefrontal cortex. When 5-HT2A receptorsare activated, a release of the excitatoryneurotransmitter glutamate occurs,increasing the neural firing all along thefrontal cortex (5) 15. The harmala alkaloid harmine which was onceknown as Telepathine and Banisterine is anaturally occurring beta-carboline alkaloid that isstructurally related to harmaline, and also foundin the vine Banisteriopsis caapi.Tetrahydroharmine is also found in B. caapi andP. harmala. Dr. Alexander Shulgin has suggestedthat harmine may be a breakdown product ofharmaline. Harmine and harmaline are reversibleMAOIs of the MAO-A isoform of the enzyme, andcan stimulate the central nervous system byinhibiting the metabolism of monoaminecompounds such as serotonin andnorepinephrine. 16. Main targets and actions (data fromHarmine is a RIMA, a reversible inhibitor ofmonoamine oxidase A (MAO-A), an enzyme whichbreaks down monoamines. Harmine selectivelybinds to MAO-A but does not inhibit the variantMAO-B.It is generally accepted that the main neurobiologymechanism of action of hallucinogens is acting asagonistis of the 5-HT2A receptors located at thepyramidal glutamatergic neurons of the layer V of theprefrontal cortex. When 5-HT2A receptors areactivated, a release of the excitatory neurotransmitterglutamate occurs, increasing the neural firing allalong the frontal cortex. 17. Derivatives of lysergic acid include structuralelements of both tryptamine andphenylethylamine and thus act on the wholegroup of the 5-HT receptors, adrenoceptors(mostly of type ) and dopamine receptors(mostly type D2) (B. T. Larson et al. 1995). Soergotamine is a partial agonist of -adrenergic and 5-HT2 receptors, and thusnarrows blood vessels and stimulatesconstriction of the uterus. 18. Ribbon diagram of an MAO-Amonomer, with FAD andclorgiline boundHarmine, and plants containing significantamounts of harmine and other harmalaalkaloids are generally not considered safetreatments for depression within themedical community. This bias however isprimarily built on previous decades ofexperience with pharmaceutical non-specificMAOIs that block both MAO-Aand MAO-B. Inhibiting MAO-A or MAO-B(in high enough doses) while consumingtyramine-laden foods e.g. cheese, cancause tyramine, ordinarily metabolized bythese enzymes, to accumulate todangerous levels. Because harminereversibly inhibits MAO-A, the harmalaalkaloids (including harmine) are lesslikely to induce this "cheese syndrome". 19. Harmal contains -carboline alkaloidsAlstonia macrophylla containsCorynanthe alkaloids Rauwolfia serpentina contains Corynanthe alkaloidCatharanthus roseus containsmonoterpenoid indole alkaloids 20. The graphs correspond to 15 of the total 18participants enrolled in the study. To avoidthe miscalculation of pharmacokineticparameters, data from three volunteers wereexcluded from the analysis due to vomitingoccurring after administration of the low dose(volunteer 6) and the high dose (volunteers 4and 18). An additional subject (volunteer 12)was excluded from the calculation ofharmalol parameters. Plasma levels for thisvolunteer after the high dose showed aplateau between 6 and 24 h, precludingparameter assessment. 21. Biosynthesis of -carboline alkaloids occursthrough the formation of Schiff base fromtryptamine and aldehyde (or keto acid) andsubsequent intramolecular Mannich reactionIn the formation of simple -carboline alkaloids,such as harmine and harmaline, pyruvic acid actsas the keto acid. In the synthesis ofmonoterpenoid indole alkaloids, secologaninplays the role of the aldehyde. Pirroloindolealkaloids are synthesized in living organisms in asimilar way (Tadeusz , 2007). 22. Uncovering the GreatestSecret of the AncientWorldBy Luke A. Myers,calibre [http://calibre-ebook.com]Over the years Banisteriopsis caapi hasbecome widespread throughout theAmazon and has found its way into themagical practices of suburban mestizo.Banisteriopsis caapi, the sacred vine of thesouls. Those who partake of it can enterthe world of the spirits by climbing downthe stem of this liana to the underworld.In Brazil a the urban use of Ayahuasca hasgiven rise to a whole new religiousmovement, known as the Daime Church,which is a strange amalgamation ofChristianity, afro-brazilian folk-beliefs andtraditional Indian practices, that usesAyahuasca as a sacrament. 23. The Ayahuascero sits in the circle ofattendants and invokes the plant spiritsby singing their icaros, their magicalsongs. He asks them to lend their powerto his brew and to guide the visions ofthe attendants. The attendants have allfasted during the day, or at the veryleast abstained from certain foods, andprepared themselves psychologically forthe ceremony. The air is laden withanticipation and anguish. Will the plantspirits be gentle?The Ayahuascero purifies the space andcasts blessings and spells of protection.He blows tobacco smoke and sprinklesfragrant flower waters as he chants hisinvocations. 24. Abstract Gerardy J, "Effect of moclobemide on rat brain monoamine oxidase Aand B: comparison with harmaline and clorgyline.", Department of Pharmacology,University of Lige, Sart Tilman, Belgium.B. T. Larson et al. (1995). "Ergovaline Binding and Activation of D2 DopamineReceptors in GH4ZR7 Cells". J Anim Sci 73 (5): 13961400.Callaway JC, Brito GS & Neves ES (2005). Phytochemical analyses of Banisteriopsiscaapi and Psychotria viridis Journal of Psychoactive Drugs 37(2): 145-150.Eric Yarnell, Kathy Abascal (April 2001). "Botanical Treatments for Depression".Alternative & Complementary Therapies 7 (3): 138143.Herraiz T, Gonzlez D, Ancn-Azpilicueta C, Arn VJ, Guilln H. (2010). "beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamineoxidase (MAO).". Food Chem Toxicol. 48 (3): 83943.http://www.sciencedirect.com/science?Li Y, Sattler R, Yang EJ, Nunes A, Ayukawa Y, Akhtar S, Ji G, Zhang PW, RothsteinJD. (18 June 2011). "Harmine, a natural beta-carboline alkaloid, upregulatesastroglial glutamate transporter expression". Neuropharmacology 60: 1168-75. 25. Louis ED; Zheng, W; Jurewicz, EC; Watner, D; Chen, J; Factor-Litvak, P; Parides, M (2002)."Elevation of blood beta-carboline alkaloids in essential tremor.". Neurology 59 (12): 19404.McKenna, Callaway, & Grb. "Scientific Investigation of Ayahuasca", Scientific Investigation ofAyahuasca, retrieved 2007-06-03.R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, BiomedicalPublications, Foster City, CA, 2008, pp. 727-728.Shulgin, Alexander and Shulgin, Ann (1997). TiHKAL: The Continuation. Transform Press.ISBN 0963009699. Pages 713714Shulgin, Alexander. "13 Harmaline", Erowid Online Texts: TiHKAL 13 HARMALINE, retrievedNovember 26, 2006.Tadeusz Aniszewski (2007). Alkaloids secrets of life. Amsterdam: Elsevier. p. 39. ISBN 978-0-444-52736-3.Xanthomicrol is the main cytotoxic component of Dracocephalum kotschyii and a potentialanti-cancer agent". Phytochemistry 66 (13): 1581. 26. Harmaline and harminefluoresce underultraviolet light.