Milli q plus filter system

The Liquid Chromatography system consisted of a three-pump Shimadzu chromatograph model LC-20AR Prominence equipped with a SIL-10AF autosampler, a CTO-20A column oven, a CBM-20A communications bus module, a DGU-20A3R inline degasser, and an SPD-M20A photodiode array detector. The LC solution® software (version 1.25) was used to process the data. The analyses were conducted on a Shim-pack 5 μm; Shimadzu) . Acetonitrile (chromatographic grade) was supplied by Mallinkrodt Baker Inc. (Phillipsburg, NJ, USA). Water was purified with a Milli-Q-plus filter system (Millipore, Bedford, MA, USA). Classic and Vacuum liquid chromatography (respectively CC and VLC; glass columns of 450 X 25 mm and 50-100 mm i.d.) were used to purify the compounds 1b-8b (Figure S1) by using silica gel 60 (Merck, art. 9385 ) and silica gel 60H (Merck, art. 7736) . Commercial hexanes and ethyl acetate (EtOAc) were purified by distillation in our facilities. The NMR spectra were run on a Bruker DPX 400 spectrometer (400 MHz for 1 H and 100 MHz for 13 C). The samples were dissolved in CDCl3, and the spectra were calibrated with the solvent signals at 7.26 ( 1 H) and 77.0 ( 13 C). HPLC grade Manool (Figure S1, IS), a natural labdane diterpene that is not found in Copaifera oleoresins, was used as internal standard, and was acquired from GlycoSyn (≥98% purity, Wellington, New Zealand).

The Liquid Chromatography system consisted of a two-pump Shimadzu chromatograph model LC-20A Prominence equipped with a SIL-20A auto sampler, a column oven CTO-20A, a CBM-20A communications bus module, a DGU-20A3 in-line degasser, and an SPD-M20A photodiode array detector. The LC solution ® software was used to process the data. The analyses were conducted on a LiChrospher 5 μm) .
Acetonitrile (chromatographic grade) was supplied by Mallinkrodt Baker Inc. (Phillipsburg, NJ, USA). Water was purified with a Milli-Q-plus filter system (Millipore, Bedford, MA, USA). The NMR spectra were run on a Bruker DPX 400 spectrometer (400 MHz for 1 H and 100 MHz for 13 C). The samples were dissolved in Dimetilsulfóxido (DMSO).

The Liquid Chromatography system consisted of a three-pump Shimadzu chromatograph model LC-20AR Prominence equipped with a SIL-10AF auto sampler, a CTO-20A column oven, a CBM-20A communications bus module, a DGU-20A3R in-line degasser, and an SPD-M20A photodiode array detector. The Lab solution ® software was used to process the data. The analyses were conducted on a Shim-pack VP-ODS column (250 × 4.6 mm i.d., 5 μm; Shimadzu) . Acetonitrile (chromatographic grade) was supplied by Mallinkrodt Baker Inc.
(Phillipsburg, NJ, USA). Water was purified with a Milli-Q-plus filter system (Millipore, Bedford, MA, USA). HPLC grade coumarin (Figure1B), a natural product that is not found in O. vulgare leaves and that was used as Internal Standard and rosmarinic acid (1) (Figure S1), the analytical standard, were both acquired from Sigma-Aldrich (≥98% purity, Darmstadt, Germany). The blood glucose levels were determined using One Touch strips quantified in a One Touch Basic Meter (Lifescan Johnson and Johnson, Inc.) .