Date: Sat, 14 Jun 1997 22:48:24 -0700
From: Mulga <mulga@shaman.lycaeum.org>
To: Multiple recipients of list <ibogaine@ibogaine.org>
Subject: re: Ibogaine in Trachelospermum jasminoides
On Sat, 14 Jun 1997 Chris Jenks <jenks@indigo.ucdavis.edu> wrote:
>
> At 11:17 AM 6/14/97 -0700, you wrote:
> >Concerning previous posts relating to Ibogaine being present in jasmine, a
> >friend provided me with the following citation.
> >
> >Alkaloids from Trachelospermum jasminoides, Atta-ur-Rahman et al., Planta
> >Medica, 54(4):364, 1988.
> >
> >The authors have found that Ibogaine is present, along with
> >tabernaemontanine, vobasine and voacangine-7-hydroxyindolenine.
> >
> >The authors do not indicate the percentage of alkaloids.
> >
> >Howard
>
> Unfortunately this article is only one page long, but below are some
> excerpts. In essence, 50 kg of apparently fresh leaves and stems were
> extracted and purified to obtain 20 grams of a mixture of alkaloids, a
> major one of which was ibogaine. There may have been grams of ibogaine, or
> just a few milligrams. The extractions given below are quite practical, but
> the chromatography of the alkaloid mixture is very expensive and practical
> only on an analytical or research scale. Two things need to be determined:
> Is the amount of ibogaine in 50 kg of leaves significant, and if other
> substances in the plant are toxic, how can they be removed in a practical
> manner?
> Thank you, Howard, for bringing this very encouraging news to our
> attention. I've seem the very page in Ott's book that you mentioned, but I
> didn't realize he was referring to a common domestic plant.
>
> - Chris
>
> Atta-ur-Rahman; Fatima, T.; Crank, George and Wasti, Shaheen. "Alkaloids
> from Trachelospermum jasminoides.", Planta Medica, (1988), 54(4), 364.
>
> "From the leaves and stems of Trachelospermum jasminoides Lem
> (Apocynaceae) (1), four indole alkaloids, namely ibogaine,
> tabernaemontanine, vobasine, and voacangine-7-hydroxyindolenine, have been
> isolated. [...]"
> "Leaves and stems (50 kg) were dried in the shade and extracted with
> ethanol. The crude alcoholic extracts were concentrated and partitioned
> between 10% hydrochloric acid and chloroform (pH 1). The chloroform layer
> was dried with anhydrous sodium sulfate and concentrated to a gum (25 g,
> F1). The aqueous acidic layer was basified with aqueous ammonia and
> extracted into chloroform at various pH values (5, 7, 9, and 11). The
> fraction obtained at pH-5 (20 g, F2) was found to contain major alkaloids.
> We have recently reported five indole alkaloids from this plant (2)."
> "The crude alkaloidal fraction (F1, 25 g) was subjected to flash
> chromatography. [...] The alkaloid isolated was identified as
> voacangine-7-hydroxyindolenine by comparison of its spectral data with
> those reported in the literature (3). [...] Voacangine-7-hydroxyindolenine
> may have been formed by air oxidation during the extraction and isolation
> process."
> "Fraction F2 (20 g) was also loaded on a silica column (750 g) and was
> eluted with increasing polarities of mixtures of petroleum ether,
> chloroform, ethyl acetate, and methanol."
> "The fraction obtained on elution with chloroform:ethyl acetate (3:1)
> consisted of a mixture of four alkaloids. This fraction was subjected to a
> flash chromatography which was eluted with increasing polarities of
> mixtures of petroleum ether in acetone. The fraction obtained on elution
> with 70% petroleum ether in acetone was found to contain two major
> alkaloids. These alkaloids were separated by preparative TLC on silica gel
> (petroleum ether:acetone:ammonia, 6:3.95:0.05). The faster moving alkaloid
> was identified as ibogaine by comparison of its spectral data with those
> reported in the literature (7) while the slower moving alkaloid was
> identified as tabernaemontanine (8)."
> "Further elution of the same column with 60% petroleum ether in acetone
> afforded another alkaloid which was further purified by preparative TLC on
> silica gel (petroleum ether:acetone:ammonia, 1:1:0.02). This alkaloid
> exhibited spectral data identical to those of vobasine (9)."
Well, just after reading this post whilst walking down the street a
local hardware/ gardening shop I passed had two Trachelospermum
jasminoides plants on special (they don't anymore:), and a cursory glance
at some gardening books would suggest that this species is in fact a
widely planted climber commonly known as Chinese Star Jasmine in Australia
A little info here, from a review of the Voacanga genus, on
tabernaemontanine and vobasine, the other alkaloids reported.
"Dregamine (a stereo-isomer of tabernaemontanine)has convulsant and
respiratory-stimulant properties and is said to inhibit fatigue; it
antagonizes prochlorperazine (but not reserpine) catalepsy, and , like
vobasine, when administered together with Rigidyl (diethylaminoethyl
benz-hydryl ether hydrochloride) causes head shaking in mice.
Tabernaemontanine causes peripheral vasodilation in chloralised dogs; it
is claimed to be of use when given orally in certain geriatric conditions
(arteriosclerosis, cerebral trauma (headache, vertigo, memory
difficulties, etc), peripheral circulatory irregularities). The mixture of
the hydrochloride salt with those of vobasine and ochropamine is stated to
have anti-inflammatory, ant-pyretic and analgesic activity compareable
with that of acetylsalicyclic acid but longer lasting. Vobasine on it's
own has little or no anti-inflammatory activity and its antipyretic and
analgesic actions are at best modest. High doses of the alkaloid give rise
to central (including respiratory) depression; the autonomous nervous
system is not affected. The compound has no diuretic activity. Perivine,
tabernaemontanine and vobasine appear to be devoid of antiviral and
anticancer activity."
I don't understand everything mentioned here, and I wonder what if any
value can be obtained from giving these alkaloids to "chloralised
dogs"(!), but it seems at least that only high doses would be of much
concern, and a side affect may just be an improved memory...
50kg is a lot of plant material, and the yield seems low compared to
other Apocynaceae containing alkaloids.
There is a variegated variey available also, and there may be different
cultivars, which from what I understand are more likely to have at least
qualitatively similar alkaloids, and between different types maybe some
variation both qualitatively and quantitavely.
One guess what climber I'll recommend folks plant in their garden,
ornamental and fragrant flowers to boot ;)
bye
> "(1) Perry, Z. M. (1895) Medicinal Plants of East and South East Asia, 31,
> MIT Press, Cambridge."
>
> "(2) Rahman, A. U., Fatima, T., Nisa, M., Wasti, S., Cranck, G. (1987)
> Planta Med. 53, 57."
>
> "(3) Agwada, V. C., Morita, Y., Renner, U., Hesse, M., Schmid, H. (1975)
> Helv. Chim. Acta 58, 1001."
> [...]
> "(7) Biemann, K., Friedmann-Spiteller, M. (1961) J. Am. Chem. Soc. 83, 4805."
>
> "(8) Husson, A., Lauglois, Y., Riche, C., Husson, H. P., and Potier, P.
> (1973) Tetrahedron 29, 3095."
>
> "(9) Renner, U., Prins, D. A., Burlingame, A. L., Biemann, K. (1963) Helv.
> Chim. Acta 46, 2186."
>
>
> ------------------------------
>
> End of IBOGAINE Digest 255
> **************************
>