Anti-Hyperglycemic Activity of Major Compounds from Calea ternifolia.

Demethylisoencecalin ( 1 ) and caleins A ( 4 ) and C ( 5 ) (3.16-31.6 mg/kg, p.o.), the major components from an infusion of Calea ternifolia controlled postprandial glucose levels during an oral sucrose tolerance test (OSTT, 3 g/kg) in normal and nicotinamide/streptozotocin (NA/STZ, 40/100 mg/kg) hyperglicemic mice. The effects were comparable to those of acarbose (5 mg/kg). During the isolation of 1 , 4 , and 5 , four additional metabolites not previously reported for the plant, were obtained, namely 6-acetyl-5-hydroxy-2-methyl-2-hydroxymethyl-2 H -chromene ( 3 ), herniarin ( 6 ), scoparone ( 7 ), and 4',7-dimethylapigenin ( 8 ). In addition, the structure of calein C ( 5 ) was confirmed by X-ray analysis. Pharmacological evaluation of the essential oil of the species (31.6-316.2 mg/kg, p.o.) provoked also an important decrement of blood glucose levels during an OSTT. Gas chromatography coupled with mass spectrometry (GC-MS) analysis of the headspace solid phase microextraction (HS-SPME)-adsorbed compounds and active essential oil obtained by hydrodistillation revealed that chromene 1 was the major component (19.92%); sesquiterpenes represented the highest percentage of the essential oil content (55.67%) and included curcumene (7.10%), spathulenol (12.95%) and caryophyllene oxide (13.0%). A suitable High Performance Liquid Chromatography (HPLC) method for quantifying chromenes 1 and 6-hydroxyacetyl-5-hydroxy-2,2-dimethyl-2 H -chromene ( 2 ) was developed and validated according to standard protocols.