Indolomonoterpenic alkaloids from Strychnos icaja roots

[en] In the course of our search for new antiplasmodial alkaloids from Strychnos icaja, we have isolated five alkaloids: three monomers, protostrychnine and genostrychnine, previously described in Strychnos nux-vomica, pseudostrychnine, already found in the leaves of the plant, a new bisindolic alkaloid, named strychnogucine C, and the first naturally occurring trimeric indolomonoterpenic alkaloid: strychnohexamine. This latter trimeric alkaloid presented an antiplasmodial activity against the FCA Plasmodium falciparum line near I muM. (C) 2002 Elsevier Science Ltd. All rights reserved.

Disciplines :

Phytobiology (plant sciences, forestry, mycology...)
Biochemistry, biophysics & molecular biology

Author, co-author :

Philippe, Geneviève ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie

De Mol, Patrick ; Université de Liège - ULiège > Département des sciences biomédicales et précliniques > Microbiologie médicale et virologie médicale

Zeches-Hanrot, M.

Nuzillard, J. M.

Tits, Monique

Angenot, Luc ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie

Frederich, Michel ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie

Language :

English

Title :

Indolomonoterpenic alkaloids from Strychnos icaja roots

Publication date :

February 2003

Journal title :

Phytochemistry

ISSN :

0031-9422

eISSN :

1873-3700

Publisher :

Pergamon-Elsevier Science Ltd, Oxford, United Kingdom

Volume :

Issue :

Pages :

623-629

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 04 June 2009

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Bibliography

Baser, K.H.C.; Bisset, N.G., 1982. Alkaloids of Sri-Lankan Strychnos nux-vomica. Phytochemistry 21, 1423-1429.
Baser, K.H.C., Bisset, N.G., Hylands, P.J., 1979. Protostrychnine, a new alkaloid from Strychnos nux-vomica. Phytochemistry 18, 512-514.
Bisset, N.G., 1976. The Asian species of Strychnos. Part IV. The alkaloids. Lloydia 39, 263-315.
Bisset, N.G., Das, B., Parello, J., 1973. Alkaloids from the leaves of Strychnos icaja Baill. Tetrahedron 29, 4137-4148.
Datta, B., Bisset, N.G., 1990. Alkaloids of Strychnos ignatii. Planta Med. 56, 133.
Desjardins, R.E., Canfield, C.J., Haynes, J.D., Chulay, J.D., 1979. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique. Antimicrob. Agents Chemother. 16, 710-718.
Frédérich, M., Hayette, M.P., Tits, M., De Mol, P., Angenot, L., 1999. In vitro activities of Strychnos alkaloids and extracts against Plasmodium falciparum. Antimicrob. Agents Chemother. 43, 2328-2331.
Frédérich, M., Depauw-Gillet, M.C., Llabres, G., Tits, M., Hayette, M.P., Brandt, V., Penelle, J., De Mol, P., Angenot, L., 2000. New antimalarial and cytotoxic sungucine derivatives from Strychnos icaja roots. Planta Med. 66, 262-269.
Frédérich, M., De Pauw, M., Prosperi, C., Tits, M., Brandt, V., Penelle, J., Hayette, M., De Mol, P., Angenot, L., 2001. Strychnogucines A and B, two new antiplasmodial bisindole alkaloids from Strychnos icaja. J. Nat. Prod. 64, 12-16.
Greenwood, B., Mutabingwa, T., 2002. Malaria in 2002. Nature 415, 670-672.
Heimberger, S.I., Scott, A.I., 1973. Biosynthesis of strychnine. J. Chem. Soc. Chem. Commun., 217-218.
Kambu, K., Coune, C., Angenot, L., 1980. Nouveaux alcaloïdes des racines du Strychnos icaja. Planta Med. 37, 161-164.
Klyne, W., Buckingham, J., 1974. Atlas of Stereochemistry: Absolute Configurations of Organic Molecules. Chapman & Hall, London.
Klyne, W., Swan, R., Bycroft, B., Schmid, H., 1965. Ermittlung der absoluten Konfiguration von Indolinalkaloiden durch Vergleich der optischen Rotationdispersionen ihrer N(8a)-Acylderivative. Helv. Chim. Acta 49, 833-841.
Klyne, W., Swan, R., Gorman, A., Schmid, H., 1968. Optische Rotationsdispersion von Indolinalkaloiden mit Ketogruppen. Helv. Chim. Acta 51, 1168-1184.
Massiot, G., Massoussa, B., Jacquier, M.J., Thépénier, P., Le Men Olivier, L., Delaude, C., Verpoorte, R., 1988. Alkaloids from roots of Strychnos matopensis. Phytochemistry 27, 3293-3304.
Mirovsky, P., Gay, F., Bustos, D., Mazier, D., Gentilini, M., 1990. Cloning of a fresh isolate of Plasmodium falciparum and drug sensitivity of the clones. Trans. Roy. Soc. Trop. Med. Hyg. 84, 511-515.
Neuwinger, H.D., 1996. African Ethnobotany: Poisons and Drugs, Chemistry, Pharmacology, Toxicology. Chapman & Hall, London.
Philippe, G., Prost, E., Nuzillard, J.M., Zéches-Hanrot, M., Tits, M., Angenot, L., Frédérich, M., 2002. Strychnohexamine from Strychnos icaja, a naturally occurring trimeric, indolomonoterpenic alkaloid. Tetrahedron Lett.43, 3387-3390.
Sandberg, F., Kristianson, K., 1970. A comparative study of the convulsant effects of Strychnos alkaloids. Acta Pharm. Suec. 7, 329-336.
Sandberg, F., Lunell, E., Ryrberg, K.J., 1969. Pharmacological and phytochemical investigations of African Strychnos species. Acta Pharm. Suec. 6.79-102.
Schübel, H., Fahn, W., Stöckigt, J., 1989. Formation of the first trimeric monoterpenoid indole alkaloids. Helv. Chim. Acta 72, 147-150.
Trager, W., Jensen, J.B., 1976. Human malaria parasites in continuous culture. Science 193, 673-675.
Verpoorte, R., 1980. Assignment of 13C NMR spectra of strychnine and brucine. J. Pharm. Sci. 69, 865-867.
Verpoorte, R., Hylands, P.J., Bisset, N.G., 1977. Carbon-13 NMR spectroscopy of some Strychnos alkaloids. Org. Magn. Res. 9, 567-571.