Alstoboonine, an Ulean-Type Indole Alkaloid from Alstonia boonei Leaves

Alstoboonine, an Ulean-Type Indole Alkaloid from Alstonia boonei Leaves

Alstonia boonei De Wild is a common plant in West Africa used in traditional medicine for various indications. While the stem bark has frequently been investigated, not much is known about the phytochemistry and bioactivity of the leaves. Within the current study, the major alkaloids of a hydroethan...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2024-03, Vol.87 (3), p.514-519
Main Authors: Grimm, Manuel, Börner, Ramona, Addotey, John N., Schmidt, Thomas J., Spiegler, Verena
Format: Article
Language:eng
Subjects:
Alkaloids - pharmacology
Alstonia - chemistry
Animals
Humans
Indole Alkaloids - chemistry
Indole Alkaloids - pharmacology
MCF-7 Cells
Plant Extracts - chemistry
Plant Extracts - pharmacology
Plant Leaves
Plasmodium falciparum
Rats
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Summary:Alstonia boonei De Wild is a common plant in West Africa used in traditional medicine for various indications. While the stem bark has frequently been investigated, not much is known about the phytochemistry and bioactivity of the leaves. Within the current study, the major alkaloids of a hydroethanolic leaf extract were therefore isolated and characterized by MS, NMR, and ECD. This led to the identification of alstoboonine 1, a new ulean-type alkaloid, along with eight previously reported indole alkaloids, 15-hydroxyangustilobine A (2), 6,7-seco-angustilobine B (3), 6,7-seco-19,20-α-epoxyangustilobine B (4), alstrostine E (5), alstrostine C (6), alstrostine D (7), 12-methoxyechitamidine (8), and 19-oxo-12-methoxyechitamidine (9). 1 was moderately active in vitro against Plasmodium falciparum NF54 (IC50 6.9 μM), but inactive against other protozoan parasites (Trypanosoma brucei, Trypanosoma cruzi, Leishmania donovani). No significant cytotoxic effects were observed in L6 rat skeletal myoblast cells and MCF-7 breast cancer cells. Similarly, compounds 3 to 9 did not show cytotoxicity in MCF-7 cells. Due to the reported traditional use of the plant as an anthelmintic, the major alkaloids 2, 5, 6, and 8 were tested against the nematode Caenorhabditis elegans. Nematicidal effects were observed for 6 (LC50 400 μM), whereas 2, 5, and 8 were inactive.
ISSN:0163-3864
1520-6025