Hydroxyalkenylresorcinols from Stylogyne turbacensis

• Published in: Journal of natural products (Washington, D.C.) Vol. 70; no. 8; pp. 1249 - 1252
• Main Authors: Jiménez-Romero, Carlos, Torres-Mendoza, Daniel, González, Luis David Ureña, Ortega-Barría, Eduardo, McPhail, Kerry L, Gerwick, William H, Cubilla-Rios, Luis
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-08-2007; Glendale, AZ American Society of Pharmacognosy
• Subjects: Animals; Antiprotozoal Agents - chemistry; Antiprotozoal Agents - isolation & purification; Antiprotozoal Agents - pharmacology; Biological and medical sciences; Cercopithecus aethiops; Female; General pharmacology; Humans; Leishmania - drug effects; Medical sciences; Myrsinaceae - chemistry; Nuclear Magnetic Resonance, Biomolecular; Panama; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plants, Medicinal - chemistry; Resorcinols - chemistry; Resorcinols - isolation & purification; Resorcinols - pharmacology; Trypanosoma cruzi - drug effects; Vero Cells; Central America; Panama; America; Antineoplastic agent; Lung; Resorcinol derivatives; Cytotoxicity; Diphenols; Medicinal plant; Antiprotozoal agent; Dicotyledones; Angiospermae; Mammary gland; Secondary alcohol; Tumor cell; Kinetoplastida; Human; Protozoa; Aliphatic compound; Pharmacognosy; Plant leaf; Dienic compound; In vitro; Biological activity; Trypanosoma cruzi; Cell line; Leishmania; Absolute configuration; Plant origin; Parasiticide; Benzenic compound; Isolation; Spermatophyta; Myrsinaceae; Ethylenic compound; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np070081d

Two new compounds, 5-(11‘(S)-hydroxy-8‘-heptadecenyl)resorcinol (3) and 5-(12‘(S)-hydroxy-8‘,14‘-heptadecadienyl)resorcinol (4), were isolated from the leaves of Stylogyne turbacensis together with the known analogue metabolites 1 and 2. Compounds 3 and 4 showed the strongest activity in the leishmania assay, 7 and 3 μM, respectively, while compounds 1, 2, and 4 showed moderate activity against a drug-resistant strain of Trypanosoma cruzi with IC50 values of 30, 25, and 22 μM, respectively. Additional testing in MCF-7 and NCI-H460 was performed for compounds 3 and 4. The structures of compounds 1−4 were elucidated using NMR, MS, and other spectroscopic data. The absolute stereochemistry of compounds 3 and 4 was also investigated using the Mosher ester approach. Peracetylated derivatives of these four metabolites were produced and their activities determined in the Trypanosoma cruzi assay.