Rapid and Easy Identification of Isomers of Coumaroyl- and Caffeoyl-D-quinic Acid by Gas Chromatography/Mass Spectrometry

Cypellocarpins A−C, Phenol Glycosides Esterified with Oleuropeic Acid, from Eucalyptus cypellocarpa

“…These differences, along with a downfield shift of a tertiary methyl signal (δ 2.07) compared to that of 2, indicated that 3 is a dehydrated derivative of 2. This structure is consistent with its UV spectrum (λ max 286, 314 nm), indicative of an extended conjugation system com- The known compounds, 2-endo-cineolylol glucoside, 9 chlorogenic acid, 5-O-coumaroylquinic acid, 10 rutin, quercetin 3-O-β-D-glucuronide, 11 isobiflorin (6), 12 and chromene glucoside (7), were also isolated. Except for 7, these were identified by comparing their spectral data with those reported in the literature.…”

“…The known compounds, 2-endo-cineolylol glucoside, chlorogenic acid, 5- O -coumaroylquinic acid, rutin, quercetin 3- O -β- d -glucuronide, isobiflorin ( 6 ), and chromene glucoside ( 7 ), were also isolated. Except for 7 , these were identified by comparing their spectral data with those reported in the literature.…”

Steroidal saponins and pseudoalkaloid oligoglycoside from Brazilian natural medicine, “fruta do lobo” (fruit of Solanum lycocarpum)

“…After partition of the methanolic extract with an EtOAc and water mixture, the aqueous phase was subjected to HP-20 cc to give an acetone-eluted fraction (0.08%), methanol-eluted fraction (2.5%), and a water-eluted fraction (2.3%). The methanol-eluted fraction was further subjected to normal and reversed-phase column chromatographies and finally HPLC to provide lyconosides Ia (1, 0.0059% from the dried fruit), Ib (2, 0.0005%), II (3, 0.0012%), III (4, 0.0004%), and IV (5, 0.0014%), lobofrutoside (6, 0.0047%), solamargine (7, 0.2827%), robeneoside A (8, 0.0268%), and solasonine (9, 0.4456%) together with kaempferol 3-O-a-L-rhamnopyranosyl(1?6)-b-D-glucopyranoside (0.0018%) (Markham et al, 1978) and 5-O-caffeoyl-D-quinic acid (0.0198%) (Fuchs and Spiteller, 1996).…”

Solvent effects in the structure dereplication of caffeoyl quinic acids

“…More solvent was then added to the final sample volume of 0.7 ml corresponding to a filling height of 40 mm in 5 mm tubes (Norell 507). The following solvents were used: methanol-d 4 The spectra were obtained under the following conditions: 1 H 30°pulse, delay after acquisition (D1) 1 s, processing with 0.3 Hz line broadening (LB) or with Lorentz-Gauss resolution enhancement and zero-filling, acquisition using 16 K (SI) data points in a spectral window of ca. 8 ppm yielded a digital resolution better than 0.2 Hz, water peak suppression was achieved by presaturation setting the HDO signal on resonance (O1); 13 C 30°p ulse, D1 3 s, collecting a spectral window of 250 ppm into 32 K data points and processing with 1.2-3 Hz LB or with Lorentz-Gauss resolution enhancement after zerofilling; 1 H 2D COSY SW 6 ppm, D1 1.2 s, 1 K ð 512 or 256 t 1 increments, 90°shifted sinebell-squared apodization, zero-filling in t 1 dimension during processing.…”

“…The latter is widely covered by publications in the field of HPLC, 1 capillary electrophoresis, 2 NMR spectroscopy 3 and mass spectrometry. 4 Enduring attention is given to both the widespread occurrence of CQAD and their diverse biological effects, for example, in the protection against lipid peroxidation 5 or as inhibitors of the hepatic glucose-6-phosphate translocase. 6 Nevertheless, as will be shown in the following, dereplication of these compounds is not always straightforward Chlorogenic acid (1)-amorphous colorless solid: C 16…”