Tabernines A−C, β-Carbolines from the Leaves of Tabernaemontana elegans

• Published in: Journal of natural products (Washington, D.C.) Vol. 72; no. 6; pp. 1147 - 1150
• Main Authors: Mansoor, Tayyab A, Ramalhete, Cátia, Molnár, Joseph, Mulhovo, Silva, Ferreira, Maria José U
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 26.06.2009; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: animal disease models; Animals; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; ATP-Binding Cassette, Sub-Family B, Member 1 - drug effects; Biological and medical sciences; Carbolines - chemistry; Carbolines - isolation & purification; Carbolines - pharmacology; cell lines; chemical structure; Chemistry, Medicinal; Drug Resistance, Multiple - drug effects; Drug Screening Assays, Antitumor; General pharmacology; Humans; indole alkaloids; Indole Alkaloids - chemistry; Indole Alkaloids - isolation & purification; Indole Alkaloids - pharmacology; leaves; Life Sciences & Biomedicine; lymphoma; Medical sciences; medicinal plants; medicinal properties; Mice; Molecular Structure; Mozambique; multiple drug resistance; nuclear magnetic resonance spectroscopy; Nuclear Magnetic Resonance, Biomolecular; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; plant extracts; Plant Leaves - chemistry; Plant Sciences; Science & Technology; Tabernaemontana; Tabernaemontana - chemistry; Tabernaemontana elegans; tabernines; Mozambique; Africa; CANCER-CELLS; DITERPENES; BISINDOLE ALKALOIDS; INDOLE ALKALOIDS; INHIBITORS; MULTIDRUG-RESISTANCE; TABERNAELEGANTININES; CHANNEL BLOCKERS; MARINE SPONGE; P-GLYCOPROTEIN; Antineoplastic agent; Angular nitrogen heterocycle; Nitrogen heterocycle; P Glycoprotein; Cytotoxicity; Lymphoblast; Medicinal plant; Apocynaceae; Alkaloid; Dicotyledones; Multiple resistance; Angiospermae; Aromatic compound; Inhibition; Tumor cell; Transmembrane protein; Pharmacognosy; Rodentia; Plant leaf; Tetracyclic compound; Tricyclic compound; In vitro; Biological activity; Vertebrata; Mammalia; Cell line; Mouse; Plant origin; MDR-1 gene; Isolation; Reversibility; Spermatophyta; Primary amine; Chemosensitizing agent; ABC transporter; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np9001477

Three novel β-carboline indole alkaloids (1−3) have been isolated from a MeOH extract of the leaves of Tabernaemontana elegans. The structures were established by means of spectroscopic techniques including 2D NMR experiments. Compounds 1 and 2 contain a two-carbon unit, attached to a structurally related β-carboline skeleton, as part of an additional six-membered ring in 1 and a seven-membered ring in 2. To the best of our knowledge, this is the first report of β-carboline indole alkaloids from the genus Tabernaemontana. Compounds 1−3 were evaluated for their ability to modulate multidrug resistance in mouse lymphoma cell lines. Compounds 1 and 3 exhibited a weak activity.