Bioactive alkyl phenols and embelin from Oxalis erythrorhiza.
The benzoquinone embelin and four alkyl phenols were isolated from an Argentinean collection of Oxalis erythrorhiza. 3-Heptadecyl-5-methoxy-phenol is reported for the first time. The structures were determined by spectroscopic methods. Embelin presented inhibitory effect on methicillin-resistant Staphylococcus aureus, Escherichia coli and the dermatophytic fungi Epidermophyton floccosum, Microsporum canis, Microsporum gypseum, Trichophyton mentagrophytes and Trichophyton rubrum with MICs ranging between 50 and 100 microg/ml. Furthermore, embelin was active against Trypanosoma cruzi trypomastigotes with 100% lysis at 100 microg/ml and cytotoxicity below the trypanocidal concentration. The new alkyl phenol 3-heptadecyl-5-methoxy-phenol was active towards Leishmania amazonensis and Leishmania donovani promastigotes with 100% lysis at 100 microg/ml. The cytotoxicity (IC50) of embelin and the new alkyl phenol on human lung fibroblasts were 739 and 366 microM, respectively. The plant is used to treat heart complains, a symptomatology related to Chagas' disease which is endemic in the San Juan Province, Argentine.
Feresin
Gabriela Egly
GE
Instituto de Ciencias Básicas, Universidad Nacional de San Juan, Avda. Ignacio de La Roza 230 Oeste, C.P. 5400 San Juan, Argentina. gferesin@unsj.edu.ar
Tapia
Alejandro
A
Sortino
Maximiliano
M
Zacchino
Susana
S
de Arias
Antonieta Rojas
AR
Inchausti
Alba
A
Yaluff
Gloria
G
Rodriguez
Jaime
J
Theoduloz
Cristina
C
Schmeda-Hirschmann
Guillermo
G
D000900:Anti-Bacterial Agents / Q000302:isolation & purification / Q000494:pharmacology / Q000633:toxicity; D000890:Anti-Infective Agents / Q000302:isolation & purification / Q000494:pharmacology* / Q000633:toxicity; D000935:Antifungal Agents / Q000302:isolation & purification / Q000494:pharmacology / Q000633:toxicity; D000981:Antiprotozoal Agents / Q000302:isolation & purification / Q000494:pharmacology / Q000633:toxicity; D016227:Benzoquinones / Q000302:isolation & purification / Q000494:pharmacology* / Q000633:toxicity; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D008826:Microbial Sensitivity Tests; D021261:Parasitic Sensitivity Tests; D010636:Phenols / Q000302:isolation & purification / Q000494:pharmacology* / Q000633:toxicity; D010936:Plant Extracts / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D000981:Antiprotozoal Agents; D016227:Benzoquinones; D010636:Phenols; D010936:Plant Extracts; C010945:embelin