Subscribe to RSS
DOI: 10.1055/s-0031-1280473
© Georg Thieme Verlag KG Stuttgart · New York
Antiplasmodial Alkaloids from the Stem Bark of Strychnos malacoclados
Publication History
received August 8, 2011
revised Dec. 1, 2011
accepted Dec. 6, 2011
Publication Date:
22 December 2011 (online)
![](https://www.thieme-connect.de/media/plantamedica/201204/lookinside/thumbnails/10.1055-s-0031-1280473-1.jpg)
Abstract
From the stem bark of Strychnos malacoclados, one new bisindole alkaloid, 3-hydroxylongicaudatine Y (1), was isolated along with the known alkaloids vomicine (2), bisnordihydrotoxiferine (3), divarine (4), longicaudatine (5), longicaudatine Y (6), and longicaudatine F (7). All the compounds were tested for their antimalarial activity against the chloroquine-sensitive 3D7 and -resistant W2 strains of Plasmodium falciparum. Longicaudatine was the most active compound with IC50 values of 0.682 and 0.573 µM, respectively. The activity of compounds 1, 3, 4, 6, and 7 against the two strains ranged from 1.191 to 6.220 µM and 0.573 to 21.848 µM, respectively. Vomicine (2), the only monomer isolated, was inactive. The alkaloids of the longicaudatine-type (1, 5–7) were more active than those of the caracurine-type (3–4). The presence of the ether bridge in the molecule seems to increase the antiplasmodial activity. Compounds 1, 5, and 7 were tested against the WI-38 human fibroblast cell line. Longicaudatine was the most cytotoxic compound with an IC50 of 2.721 µM. Longicaudatine F was 40–46 times more active against the two strains of P. falciparum than against the human fibroblasts and was thus considered as the more selective alkaloid. The structures of the compounds were determined based on the analysis of their spectral data.
Key words
Strychnos malacoclados - Loganiaceae - Plasmodium falciparum - 3-hydroxylongicaudatine Y - antiplasmodial activity - cytotoxicity
References
- 1 Leeuwenberg A J M. The loganiaceae of Africa VIII. Strychnos III. Wageningen: Mededelingen Landbouwhogeschool Wageningen; 1969: 171-174
- 2 Verpoorte R, Svendsen A B. 11-methoxydiaboline in Strychnos malacoclados. Phytochemistry. 1974; 13 2011
- 3 Verpoorte R. Communication. In: Massiot G, Delaude C, Brossi A, editors The alkaloids. New York: Academic Press; 1988: 211-239
- 4 Frédérich M, Hayette M P, Tits M, De Mol P, Angenot L. In vitro activities of Strychnos alkaloids and extracts against Plasmodium falciparum. Antimicrob Agents Chemother. 1999; 43 2328-2331
- 5 Frédérich M, De Pau M C, Llabrès G, Tits M, Hayette M P, Brandt V, Penelle J, De Mol P, Angenot L. New antimalarial and cytototoxic sungucine derivatives from Strychnos icaja roots. Planta Med. 2000; 6 262-269
- 6 Philippe G, Angenot L, De Mol P, Goffin E, Hayette M P, Tits M, Frédérich M. In vitro screening of some Strychnos species for antiplasmodial activity. J Ethnopharmacol. 2005; 97 535-539
- 7 Massiot G, Zèches M, Mirand C, Le Men-Olivier L, Delaude C, Baser K H C, Bavovada R, Bisset N G, Hylands P J, Strombom J, Verpoorte R. Occurrence of longicaudatine, a new-type of bis-indole base and bisnor-C-alkaloid in Strychnos species. J Org Chem. 1983; 48 1869-1872
- 8 Massiot G, Thepenier P, Jacquier M-J, Lounkokobi J, Mirand C, Zèches M, Le Men O. Further alkaloids from Strychnos longicaudata and Strychnos ngouniensis. Tetrahedron. 1983; 39 3645-3656
- 9 Massiot G, Massouma B, Jacquier M-J, Thépénier P, Le Men-Olivier L, Delaude C, Verpoorte R. Alkaloids from roots of Strychnos matopensis. Phytochemistry. 1988; 25 3293-3304
- 10 Mukherjee R, Das B C, Keifer P A, Shoolery J N. Structure and stereochemistry of divarine: Another new bisindole alkaloid from Strychnos divaricans Ducke. Heterocycles. 1994; 38 1965-1970
- 11 Delaude C, Delaude L. Les Strychnos africains et leurs alcaloïdes. Bull Soc Roy Sci Liège. 1997; 66 183-286
- 12 Bisset N G, Das B C, Parello J. Alkaloids from the leaves of Strychnos icaja Baill. Tetrahedron. 1973; 29 4137-4148
- 13 Mukherjee R, da Silva T M S, Guimarães J B L, de J Oliveira E, Keifer P A, Shoolery J N. Tertiary alkaloid fraction of Strychnos atlantica: Confirmation of the identity and structures of indole alkaloids by high field nuclear magnetic resonance spectroscopy. Phytochem Anal. 1997; 8 115-119
- 14 Massiot G, Thepenier P, Jacquier M-J, Le Men-Olivier L, Delaude C. Alkaloids from the roots of Strychnos potatorum. Phytochemistry. 1992; 31 2873-2876
- 15 Tavernier D, Anteunis M J O, Tits M J G, Angenot L J G. The 1H NMR spectra of the Strychnos alkaloids retuline isoretuline, and their n-deacetyl compounds. Bull Soc Chim Belg. 1978; 87 595-607
- 16 Philippe G, De Mol P, Zèches-Hanrot M, Nuzillard J M, Tits M H, Angenot L, Frédérich M. Indolomonoterpenic alkaloids from Strychnos icaja roots. Phytochemistry. 2003; 62 623-629
- 17 Wenkert E, Bringi N V. A stereochemical interpretation of the biosynthesis of indol. Chem Soc. 1959; 81 1474-1481
- 18 Frédérich M, Jacquier M J, Thépenier P, De Mol P, Tits M, Philippe G, Delaude C, Angenot L, Zèches M. Antiplasmodial activity of alkaloids from various Strychnos species. J Nat Prod. 2002; 65 1381-1386
- 19 Jonville M C, Kodja H, Humeau L, Fournel J, De Mol P, Cao M, Angenot L, Frédérich M. Screening of medicinal plants from Reunion Island for antimalarial and cytotoxic activity. J Ethnopharmacol. 2008; 120 382-386
Dr. Alembert T. Tchinda
Laboratory of Phytochemistry
Center for Studies on Medicinal Plants and Traditional Medicine
Institute of Medical Research and Medicinal Plants Studies
PO Box 6163
Yaoundé
Cameroon
Phone: +23 7 76 92 59 29
Email: alembertt2002@yahoo.fr