Hydroxyalkenylresorcinols from Stylogyne turbacensis.
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 microM, respectively, while compounds 1, 2, and 4 showed moderate activity against a drug-resistant strain of Trypanosoma cruzi with IC(50) values of 30, 25, and 22 microM, 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.
Jiménez-Romero
Carlos
C
Laboratory of Tropical Bioorganic Chemistry, Faculty of Natural, Exact Sciences and Technology, Apartado 0824-10835, University of Panama, Panama City, Republic of Panama.
Torres-Mendoza
Daniel
D
Ureña González
Luis David
LD
Ortega-Barría
Eduardo
E
McPhail
Kerry L
KL
Gerwick
William H
WH
Cubilla-Rios
Luis
L
D000818:Animals; D000981:Antiprotozoal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002522:Chlorocebus aethiops; D005260:Female; D006801:Humans; D007891:Leishmania / Q000187:drug effects*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010176:Panama; D010946:Plants, Medicinal / Q000737:chemistry*; D029623:Primulaceae / Q000737:chemistry*; D012118:Resorcinols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014349:Trypanosoma cruzi / Q000187:drug effects*; D014709:Vero Cells
C522941:5-(11'(S)-hydroxy-8'-heptadecenyl)resorcinol; C522939:5-(12'(S)-hydroxy-8',14'-heptadecadienyl)resorcinol; D000981:Antiprotozoal Agents; D012118:Resorcinols