Bannisteriopis cappi insight

1. TAIWO, MICHAEL ADEDAYO

2. Introduction
Banisteriopsis caapi : diagram, general features and taxonomic
Study on Banisteriopsis caapi
General features of Banisteriopsis caapi
Active compounds
Traditional uses
Medical uses
Example of study
Critic: Vine of the Soul
Search on databases
Structures of the alkaloids
Mechanism of action
Plants Chemically Related
Adverse effects of Banisteriopsis caapi alkaloids
Biosynthesis of β-carboline alkaloids
Bibliograhy

3. The Banisteriopsis caapi
Flowering Banisteriopsis caapi

4. Taxonomic classification of Banisteriopsis caapi
 Kingdom: Plantae
 Order: Malpighiales
 Family: Malpighiaceae
 Genus: Banisteriopsis
 Species: B. caapi
COMMON NAMES: Ayahuasca Vine, Bejuco de Oro,
Biaxa, Boa Vine, Caapi, Dapa, Doctor, Kaapi, Kahi,
Maridi, Mihi, Natema, Nepe, Pinde, Totenliane, Vine
of the Dead, Vine of the Soul, Yage, Yahe, Yaje,
Yaxe.

5. There are two scientifically accepted varieties:
I. Banisteriopsis caapi var. caupuri with knotty stems
II. Banisteriopsis caapi var. tukunaka with smooth stems
i ii

6. General features of Banisteriopsis caapi
Banisteriopsis caapi is a South American shrub of the
family Malpighiaceae
The bark is usually chocolate-brown and smooth.
Banisteriopsis caapi produces opposite, oval
shaped leaves to 8-20 cm long and 3-9 cm wide.
The flowers are pink petalled to 12-14 mm in
diameter and 2.5-3 mm long.
The Ayahuasca vine's fruit is a nut that grows to
5mm long.
Banisteriopsis caapi is often propagated through
vegetative cuttings and sometimes by seed
glabrous stems

7. Banisteriopis caapi flowers

8. TRADITIONAL USES:
Amazonian peoples uses Banisteriopsis caapi, as
sacramental beverage for its “magicalpowers”.
Surgeries conducted by native healers take place
at night. These healers carefully screen their
prospective patients and will not allow those
suffering from extreme mental disorders to take
part for fear of disrupting the entire healing
session due to hallucinogenic property of the
drink.

9. In war due to the psychoactive effects of these
native preparations.
Ayahuasca is also used for its curative powers.
Hoasa is believed to have been in use since the
first aborigines in Brazil and prior to the invasion
of the Spanish explorers, it was used by shaman
for magic, divination, sorcery and to both detect
and treat illnesses.

10. • The serious scientific study of ayahuasca began with the
field investigations of the English botanist Richard Spruce
throughout the 1850s.
• Among the medical uses we can count: Anticanceter
(Harmine showed cytotoxicity against HL60 and K562 cell
lines), psychotherapy, Parkinson's disease, stress, fevers,
wounds, it also acts as purgative, and the alkaloids can be
used as an MAOI (MonoAmine Oxidase Inhibitor) to
facilitate the ingestion of N,N-Dimetiltryptamine (DMT) and
other tryptamines
Medical
uses

11. Active compounds
Alkaloids
 Harmine, 0.31-8.43%
 Harmaline, 0.03-0.83%
 Tetrahydroharmine, 0.05-2.94% (Callaway et
al,2005).
 Others include:
Harmilinic acid:7-Methoxy-3,4-dihydro-beta-carboline1-
carboxylic acid
Harmanamide:1-Carbamoyl-7-methoxy-beta-carboline
Acetylnorharmine: 1-Acetyl-7-methoxy-beta-carboline
Harmalol:1-Methyl-4,9-dihydro-3H-pyrido[3,4-
b]indol-7-ol (McKenna, Callaway, & Grb 2007)

12. Harmine
Harmalol
Harmaline
Tetrahydroharmine
Harmalan
They are reversible inhibitors of MAO-A (RIMA).

14.  We now know that the
"divinity" resident in
special plants is chemical
in nature.
It is of importance,
therefore, to seek out
these primitive races and
ascertain the plants which
they have found available
in their economic life, in
order that perchance the
valuable properties they
have utilized in their wild
life may fill some vacant
niche in our own."

15. It is generally accepted that the main
neurobiology mechanism of action of
hallucinogens is acting as agonistis of the 5-
HT2A receptors located at the pyramidal
glutamatergic neurons of the layer V of the
prefrontal cortex. When 5-HT2A receptors
are activated, a release of the excitatory
neurotransmitter glutamate occurs,
increasing the neural firing all along the
frontal cortex (5)

16. The harmala alkaloid harmine which was once
known as Telepathine and Banisterine is a
naturally occurring beta-carboline alkaloid that is
structurally related to harmaline, and also found
in the vine Banisteriopsis caapi.
Tetrahydroharmine is also found in B. caapi and
P. harmala. Dr. Alexander Shulgin has suggested
that harmine may be a breakdown product of
harmaline. Harmine and harmaline are reversible
MAOIs of the MAO-A isoform of the enzyme, and
can stimulate the central nervous system by
inhibiting the metabolism of monoamine
compounds such as serotonin and
norepinephrine.

17. Main targets and actions (data from
Harmine is a RIMA, a reversible inhibitor of
monoamine oxidase A (MAO-A), an enzyme which
breaks down monoamines. Harmine selectively
binds to MAO-A but does not inhibit the variant
MAO-B.
It is generally accepted that the main neurobiology
mechanism of action of hallucinogens is acting as
agonistis of the 5-HT2A receptors located at the
pyramidal glutamatergic neurons of the layer V of the
prefrontal cortex. When 5-HT2A receptors are
activated, a release of the excitatory neurotransmitter
glutamate occurs, increasing the neural firing all
along the frontal cortex.

18. Derivatives of lysergic acid include structural
elements of both tryptamine and
phenylethylamine and thus act on the whole
group of the 5-HT receptors, adrenoceptors
(mostly of type α) and dopamine receptors
(mostly type D2) (B. T. Larson et al. 1995). So
ergotamine is a partial agonist of α-
adrenergic and 5-HT2 receptors, and thus
narrows blood vessels and stimulates
constriction of the uterus.

19. Ribbon diagram of an MAO-A
monomer, with FAD and
clorgiline bound
Harmine, and plants containing significant
amounts of harmine and other harmala
alkaloids are generally not considered safe
treatments for depression within the
medical community. This bias however is
primarily built on previous decades of
experience with pharmaceutical non-specific
MAOIs that block both MAO-A
and MAO-B. Inhibiting MAO-A or MAO-B
(in high enough doses) while consuming
tyramine-laden foods e.g. cheese, can
cause tyramine, ordinarily metabolized by
these enzymes, to accumulate to
dangerous levels. Because harmine
reversibly inhibits MAO-A, the harmala
alkaloids (including harmine) are less
likely to induce this "cheese syndrome".

20. Harmal contains β-carboline alkaloids
Alstonia macrophylla contains
Corynanthe alkaloids
 Rauwolfia serpentina contains Corynanthe alkaloid
Catharanthus roseus contains
monoterpenoid indole alkaloids

21. The graphs correspond to 15 of the total 18
participants enrolled in the study. To avoid
the miscalculation of pharmacokinetic
parameters, data from three volunteers were
excluded from the analysis due to vomiting
occurring after administration of the low dose
(volunteer 6) and the high dose (volunteers 4
and 18). An additional subject (volunteer 12)
was excluded from the calculation of
harmalol parameters. Plasma levels for this
volunteer after the high dose showed a
plateau between 6 and 24 h, precluding
parameter assessment.

24. Biosynthesis of β-carboline alkaloids occurs
through the formation of Schiff base from
tryptamine and aldehyde (or keto acid) and
subsequent intramolecular Mannich reaction
In the formation of simple β-carboline alkaloids,
such as harmine and harmaline, pyruvic acid acts
as the keto acid. In the synthesis of
monoterpenoid indole alkaloids, secologanin
plays the role of the aldehyde. Pirroloindole
alkaloids are synthesized in living organisms in a
similar way (Tadeusz , 2007).

26. Uncovering the Greatest
Secret of the Ancient
World
By Luke A. Myers,
calibre [http://calibre-ebook.
com]
Over the years Banisteriopsis caapi has
become widespread throughout the
Amazon and has found its way into the
magical practices of suburban mestizo.
Banisteriopsis caapi, the sacred vine of the
souls. Those who partake of it can enter
the world of the spirits by climbing down
the stem of this liana to the underworld.
In Brazil a the urban use of Ayahuasca has
given rise to a whole new religious
movement, known as the Daime Church,
which is a strange amalgamation of
Christianity, afro-brazilian folk-beliefs and
traditional Indian practices, that uses
Ayahuasca as a sacrament.

27. The Ayahuascero sits in the circle of
attendants and invokes the plant spirits
by singing their icaros, their magical
songs. He asks them to lend their power
to his brew and to guide the visions of
the attendants. The attendants have all
fasted during the day, or at the very
least abstained from certain foods, and
prepared themselves psychologically for
the ceremony. The air is laden with
anticipation and anguish. Will the plant
spirits be gentle?
The Ayahuascero purifies the space and
casts blessings and spells of protection.
He blows tobacco smoke and sprinkles
fragrant flower waters as he chants his
invocations.

28. Abstract Gerardy J, "Effect of moclobemide on rat brain monoamine oxidase A
and B: comparison with harmaline and clorgyline.", Department of Pharmacology,
University of Liège, Sart Tilman, Belgium.
B. T. Larson et al. (1995). "Ergovaline Binding and Activation of D2 Dopamine
Receptors in GH4ZR7 Cells". J Anim Sci 73 (5): 1396–1400.
Callaway JC, Brito GS & Neves ES (2005). Phytochemical analyses of Banisteriopsis
caapi 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): 138–143.
Herraiz T, González D, Ancín-Azpilicueta C, Arán VJ, Guillén H. (2010). "beta-
Carboline alkaloids in Peganum harmala and inhibition of human monoamine
oxidase (MAO).". Food Chem Toxicol. 48 (3): 839–43.
http://www.sciencedirect.com/science?
Li Y, Sattler R, Yang EJ, Nunes A, Ayukawa Y, Akhtar S, Ji G, Zhang PW, Rothstein
JD. (18 June 2011). "Harmine, a natural beta-carboline alkaloid, upregulates
astroglial glutamate transporter expression". Neuropharmacology 60: 1168-75.

29. 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): 1940–4.
McKenna, Callaway, & Grb. "Scientific Investigation of Ayahuasca", Scientific Investigation of
Ayahuasca, retrieved 2007-06-03.
R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical
Publications, Foster City, CA, 2008, pp. 727-728.
Shulgin, Alexander and Shulgin, Ann (1997). TiHKAL: The Continuation. Transform Press.
ISBN 0963009699. Pages 713–714
Shulgin, Alexander. "13 Harmaline", Erowid Online Texts: TiHKAL 13 HARMALINE, retrieved
November 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 potential
anti-cancer agent". Phytochemistry 66 (13): 1581.

30. Harmaline and harmine
fluoresce under
ultraviolet light.