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Hydroxyalkenylresorcinols from Stylogyne turbacensis.
J Nat Prod. 2007 Aug; 70(8):1249-52.JN

Abstract

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.

Authors+Show Affiliations

Jiménez-Romero 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 D
No affiliation info available
Ureña González LD
No affiliation info available
Ortega-Barría E
No affiliation info available
McPhail KL
No affiliation info available
Gerwick WH
No affiliation info available
Cubilla-Rios L
No affiliation info available

MeSH

AnimalsAntiprotozoal AgentsChlorocebus aethiopsFemaleHumansLeishmaniaNuclear Magnetic Resonance, BiomolecularPanamaPlants, MedicinalPrimulaceaeResorcinolsTrypanosoma cruziVero Cells

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

17629327

Citation

Jiménez-Romero, Carlos, et al. "Hydroxyalkenylresorcinols From Stylogyne Turbacensis." Journal of Natural Products, vol. 70, no. 8, 2007, pp. 1249-52.
Jiménez-Romero C, Torres-Mendoza D, Ureña González LD, et al. Hydroxyalkenylresorcinols from Stylogyne turbacensis. J Nat Prod. 2007;70(8):1249-52.
Jiménez-Romero, C., Torres-Mendoza, D., Ureña González, L. D., Ortega-Barría, E., McPhail, K. L., Gerwick, W. H., & Cubilla-Rios, L. (2007). Hydroxyalkenylresorcinols from Stylogyne turbacensis. Journal of Natural Products, 70(8), 1249-52.
Jiménez-Romero C, et al. Hydroxyalkenylresorcinols From Stylogyne Turbacensis. J Nat Prod. 2007;70(8):1249-52. PubMed PMID: 17629327.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Hydroxyalkenylresorcinols from Stylogyne turbacensis. AU - Jiménez-Romero,Carlos, AU - Torres-Mendoza,Daniel, AU - Ureña González,Luis David, AU - Ortega-Barría,Eduardo, AU - McPhail,Kerry L, AU - Gerwick,William H, AU - Cubilla-Rios,Luis, Y1 - 2007/07/13/ PY - 2007/7/17/pubmed PY - 2007/10/5/medline PY - 2007/7/17/entrez SP - 1249 EP - 52 JF - Journal of natural products JO - J Nat Prod VL - 70 IS - 8 N2 - 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. SN - 0163-3864 UR - https://www.unboundmedicine.com/medline/citation/17629327/Hydroxyalkenylresorcinols_from_Stylogyne_turbacensis_ L2 - https://doi.org/10.1021/np070081d DB - PRIME DP - Unbound Medicine ER -