Poster
peripheral 1-bond cleavages of the molecule. The spectral data
and elemental analysis of 3 is in complete agreement with the
structure and lenticellarine is being proposed.
References
1. Powell, R. G., (1972) Phytochemistry 11, 1467.
2. Aladesanmi, A. J., Kelley, C. J. and Leary, J. D. (1983) J. Nat.
Prod. 46, 127.
3. Langlois, N., Das, B. C., Potier, P. and Lacombe, L., (1970) Bull.
Soc. Chim France 3535.
P39 A New Alkaloid from Psychotria forsteriana
Adjibade Y.', Kuballa B.', Cabalion P.2, Anton R'.
Laboratoire de Pharmacognosie, Faculte de Pharmcie, Universite
Louis Pasteur, B. P. 10, 67048 Strasbourg Cedex
2
Orstom, Vanuatu (New-Hebrides)
The study of the alkaloidal extract from the leaves of this plant
showed that they elaborate original alkaloids: polymers con-
taining three, four or five pyrrolidinoindoline units (1). Ac-
cording to some preliminary pharmacological tests, these com-
pounds present some interesting properties i. e. cytotoxicity
(1), platelets antiaggregation activity (2).
A first alkaloid was isolated from the stem bark and iden-
tified as calycanthine (3), an uncommon alkaloid in this family
only related to the usually occuring class of substances in this
group by its presumed biosynthetic pathway from tryptophan
(4).
The present communication concerns the extraction, charac-
terization and identification of a probably new polyindolinic
type alkaloid from the stem bark of Psychotria forsteriana A.
Gray (Rubiaceae) which usually occurs in Vanuatu (New-Heb-
rides).
The total alkaloidal content of the stem bark was isolated on
the basis of a classical but selective alkaloid extraction proce-
dure as reported in a previous communication (3).
Various column chromatographies on silica gel, aluminium
oxyde, gel filtration on Sephadex LH 20 and high performance
liquid chromatography were performed.
The spectral evidences suggest a polyindolinic type structure
probably a polymer of more than eight pyrrolidinoindoline
units. Ultraviolet and infrared absorptions are charasteristic of
the indoline nucleus and the chemical shifts in proton nuclear
magnetic resonance (NMR) spectrometry are similar to those
of the alkaloids of the leaves of this plant.
The mass spectra shows a singular fragmentation by both
electron impact and chemical ionization. The parent molecular
ion peak being above mle 1552.
References
1. Roth A. (1984), Doctorat de 3e cycle, Université Louis Pasteur,
Strasbourg
2. Beretz A., Roth A., Corre G., Kuballa B., Anton R., Cazenave
J.P. (1985), Planta Med., 4,300—303
3. Adjibade Y., Kuballa B., Cabalion P., Anton R. (1985), Acta
Agron. Hung.,34 (suppl.), 81
4. Hall E.S. et al. (1967), Tetrahedron, 23,4131—4141
523
P40 New Alkaloids from Crinum asiaticum
D. Beutner and A. W. Frahm
Institut für Pharmazeutische Chemie der UniversitSt Bonn, Kreuz-
bergweg 26, D-5300 Bonn I
A reinvestigation of Crinum asiaticum L. (Amaryllidaceae) (1,
2), the leaves and bulbs of which have been collected in Thai-
land, has enlarged in special the knowledge of the distribution
pattern of the minor alkaloids. So far eight alkaloids have been
isolated, as well as three phenanthridones (3), two of which are
newly discovered in this plant. Among the former are three
new amaryllidaceae alkaloids of the (—)-crinane type 1 and of
the (+)-crinane type 2 respectively, together with flexinine,
which has been found in this species for the first time.
Lycorine, ubiquitously found in the Amaryllidaceae family,
together with the (+)- and (—)-crinane representatives ermine,
haemanthamine and crinamine have been reidentified.
Downloaded by: University of Pennsylvania Libraries. Copyrighted material.
2
The sterically demanding structures of the new alkaloids
could be elucidated by means of modern spectroscopic
techniques with stress on 2D-homo and 2D-hetero-NMR-spec-
troscopy.
References
1. K. Tanaka (1937); J. Pharm. Soc. Japan, 57, 139
Chem. Zentr., 1937, II, 3322
2. H.-G. Boit, W. DOpke and W. Stender (1957) Chem. Ber. 90,2203
3. for comparison see:
S. Ghosal, (1981) (Special lecture) Sixth Indo-Soviet Symp. on
Chemistry of Natural Products, pp. 71—72, NCL, Puna, India.
P41 Ipobscurines, Non-ergoline Type Indole Com-
pounds from the Seeds of Ipomoea obscura
Eckart Eich, Hans-Joachim Sattler and Erwin Henn
Fachbereich Pharmazie der Universitat Mainz, Saarstr. 21, D-6500
Mainz
It is well-known that ergoline alkaloids are secondary products
in seeds of certain tropical Convolvulaceae species (1). Inves-
tigating phytochemical and chemotaxonomic points of view in
this plant family we collected seeds of Ipomoea obscura Ker-
Gawl. in Sri Lanka. Leaves of this species (Singhal.:
Mahamadu; Tamil.: Chirudali) are used in the Ayurvedic
medicine against different diseases. From the seeds of this latex
containing plant we could isolate two indole type compounds
(total content: 0.006%). As these compounds showed positive
van Urk's reactions it seemed to be obvious to assume new er-
goline type structures. However, structural elucidation studies
(1H- and '3C-NMR data, positive ion fast bombardement
(FAB) mass spectral data) surprisingly led to an identification
as amide type hydroxycinnamic acid conjugates with serotonin.
One compound with a M of 322 is shown to be Nb-(E)-p-
coumaroyl-serotonin (structural formula given) for which we
propose the trivial name ipobscurine A. The second conjugate
(M: 518), ipobscurine B, possesses a more complicated struc-