Antileishmanial Germacranolides fromCalea zacatechichi

Abstract

Phytochemical study of the leaves and stems of Calea zacatechichi Schl. (Asteraceae) led to the isolation of a series of six germacranolides (1-6) with significant antileishmanial activity. The structure of a new compound named by us as calealactone D (1) was determined by NMR and MS, and its absolute configuration by X-ray crystallography. In addition, calealactone E (5) was discovered as a new naturally occurring compound, and the absolute configuration of calealactone C (2) was also determined by X-ray crystallography. All compounds were biologically evaluated in antimicrobial and antiprotozoal assays.

The genus Calea L.: A review on traditional uses, phytochemistry, and biological activities

“…Sesquiterpenes lactones constitute the largest group of metabolites found in Calea species, and several biological activities have been assigned for this chemical class (Lima et al, ; Ohguchi et al, ; Umemura et al, ; Wu et al, ). One hundred forty‐three (1–143) compounds belonging to this chemical category have been isolated in Calea plants, including 63 heliangolides (1–63), 44 germacranolides (64–107), 24 guianolides (108–131), and 12 eudesmanolides (132–143).…”

“…Wu et al () investigated antileishmanial, antiplasmodial, antimycobacterial, and antimicrobial activities of six germacranolide sesquiterpene lactones (73, 75, 85–87, and 90) isolated from methanol extract of C. zacatechichi aerial parts. Isolated compounds were tested against 11 strains.…”

The genus Calea L.: A review of isolated compounds and biological activities

“…All the compounds possessed leishmanicidal effects compared with the positive control pentamidine. The crude methanol extract obtained by percolation was sequentially extracted with chloroform and hexane and subjected to vacuum liquid chromatography on silica gel, eluting successively with gradient n-hexane-ethyl acetate mixtures of increasing polarities (Wu et al, 2011).…”

Chromenes from leaves of Calea pinnatifida and evaluation of their leishmanicidal activity

“…This genus has been reported in the literature to possess various biological properties, such as anti-inflammatory (Gomes and Gil, 2011), antiplasmodial (Kohler et al, 2002), antileishmanial (Wu et al, 2011), acaricidal (Ribeiro et al, 2011), antifungal (Flach et al, 2002), antidiabetic (Ramos et al, 1992), antimicrobial (Do Nascimento et al, 2004), antihypertensive (Guerrero et al, 2002), and cytotoxic activities (Nakagawa et al, 2005).…”