Phenolic Profile of Potentilla anserina L. (Rosaceae) Herb of Siberian Origin and Development of a Rapid Method for Simultaneous Determination of Major Phenolics in P. anserina Pharmaceutical Products by Microcolumn RP-HPLC-UV

Abstract

A chemical study of Potentilla anserina L. herb (Rosaceae) of Siberian origin led to the isolation of 17 compounds. Three ellagitannins-potentillin, agrimonic acid A and B-are reported for the first time in this species. With a view to rapid quantitative analysis, a new method was developed for simultaneous determination of major phenolic compounds in P. anserina, including caffeic acid, myricetin-3-O-glucuronide, agrimoniin, ellagic acid, miquelianin, isorhamnetin-3-O-glucuronide, and kaempferol-3-O-rhamnoside. The quantitative determination was conducted by microcolumn reversed phase high-performance liquid chromatography with UV detection. Separation was performed using a ProntoSIL-120-5-C18 AQ column (60 mm × 1 mm × 5 μm) with six-step gradient elution of aqueous 0.2 М LiClO4 in 0.006 M HClO4 and acetonitrile as mobile phases. The components were quantified by HPLC-UV at 270 nm. All calibration curves showed good linearity (r 2 > 0.999) within test ranges. The reproducibility was evaluated by intra-and inter-day assays, and RSD values were less than 2.8%. The recoveries were between 97.15 and 102.38%. The limits of detection ranged from 0.21 to 1.94 μg/mL, and limits of quantification ranged from 0.65 to 5.88 μg/mL, respectively. Various solvents, extraction methods, temperatures, and times were evaluated to obtain the best extraction efficiency. OPEN ACCESSMolecules 2015, 20 225The developed method was successfully applied for the analysis of selected pharmaceutical products: 12 batches of P. anserina herb collected from three Siberian regions (Yakutia, Buryatia, Irkutsk), two commercial samples of P. anserina herb, and some preparations (liquid extract, tincture, decoction, infusion, and dry extract).

Phenolome of Asian Agrimony Tea (Agrimonia asiatica Juz., Rosaceae): LC-MS Profile, α-Glucosidase Inhibitory Potential and Stability

“…The following chemicals were acquired from Aktin Chemicals Inc. (Chengdu, China): kaempferol-3- O -(6″-p-coumaroyl)-glucoside ( 56 , tiliroside); Chemwill Asia Co., Ltd. (Beijing, China): agrimoniin ( 36 ); ChemFaces (Wuhan, China): apigenin 7- O -(6″- O -malonylglucoside) ( 59 ); Extrasynthese (Lyon, France): 5- O -caffeoyl quinic acid ( 14 , neochlorogenic acid); kaempferol-3- O -glucoside ( 49 ); kaempferol-3- O -rhamnoside ( 54 ); luteolin-7- O -glucoside ( 43 , cynaroside); procyanidin B3 ( 12 ); quercetin-3- O -glucoside ( 41 , isoquercitrin); quercetin-3- O -rhamnoside ( 48 ); Sigma-Aldrich (St. Louis, MO, USA): acarbose; apigenin-7- O -glucoside ( 50 , cosmosiin); apigenin-7- O -glucuronide ( 51 ); bovine serum albumin (BSA); 4- O -caffeoylquinic acid ( 8 ); catechin ( 13 ); 1,3-di- O -caffeoylquinic acid ( 26 ); 3,5-di- O -caffeoylquinic acid ( 46 ); ellagic acid ( 38 ); epicatechin ( 23 ); epicatechin gallate ( 37 ); epigallocatechin ( 15 ); 1- O -galloyl-glucose ( 2 ); kaempferol-3- O -(6″- O -rhamnosyl)-glucoside ( 47 , nicotiflorin); luteolin-7- O -glucuronide ( 44 ); procyanidin B1 ( 10 ); procyanidin B2 ( 16 ); quercetin-3- O -glucuronide ( 42 ); quercetin-3- O -(6″-malonyl)-glucoside ( 45 ); di-sodium hydrogen phosphate; α-glucosidase from Saccharomyces cerevisiae (type 1, 10 U/mg); lithium perchlorate; 4-nitrophenyl-α- d -glucopyranoside; perchloric acid; potassium dihydrogen phosphate; sodium carbonate. 2-Pyrone-4,6-dicarboxylic acid ( 6 ), pedunculagin ( 7 ), and potentillin ( 32 ) were isolated previously from C. palustre [ 22 ]; tellimagrandins ( 11 , 19 , 31 , 40 ) were isolated earlier from Filipendula ulmaria [ 23 ]; gemin A ( 34 ), agrimonic acid A ( 33 ), agrimonic acid B ( 35 ) were isolated from Potentilla anserina [ 24 ], 6-hydroxyluteolin-7- O -glucoside ( 28 ) was isolated from Rhaponticum uniflorum [ 26 ].…”

“…Although herbal products are generally considered safe due to their natural origin, they are a complex mixture of different substances for which detailed chemical profiling demands serious research [ 21 ]. As a part of our continued investigation of antidiabetic plant constituents of Rosaceous plants [ 22 , 23 , 24 , 25 ], the present work aimed to perform chromato-mass-spectrometric profiling of A. asiatica herb with high-performance liquid chromatography with photodiode array and electrospray triple quadrupole mass-spectrometric detection (HPLC-PDA-ESI-tQ-MS), as well as analysis of A. asiatica herb for inhibitory activity against digestive enzyme α-glucosidase. This multisectoral approach is an important basis for promoting the bioactive compounds of A. asiatica herb for use in future antidiabetic drugs.…”

A comprehensive review of agrimoniin

“…The extraction procedures applied for agrimoniin determination in plants and commercial products (Table ) are generally solid–liquid extraction (SLE) using acetone, 70% acetone solution, 60% acetone solution, 50% aqueous methanol solution, pure methanol, pure water, or hot water . It has been reported that ellagitannins may be unstable if treated with higher temperatures, resulting in their decomposition to ellagic acid .…”

“…Olennikov and colleagues studied all parameters that can influence the extraction efficiency for phenolics and agrimoniin, such as solvent type, liquid‐to‐solid ratio, extraction temperature, and extraction time. Detailed experiments led to the conclusion that the optimal condition for agrimoniin extraction from P. anserina herb is sonification with 60% acetone in a liquid‐to‐solid ratio of 1:40 at 40 °C for 30 minutes …”

“…From the analytical viewpoint, tannin compounds can be determined using different procedures, such as high‐performance liquid chromatography (HPLC) coupled with DAD or photodiode array (PDA) detectors . In addition to studies that report liquid chromatography (also in the UHPLC configuration) or HPLC‐DAD coupled with mass spectrometry (MS), there is also one paper reporting more complex instrument configurations, such as HPLC coupled with DAD, charged aerosol detector (CAD), and mass spectroscopy (MS) operating in fragmentation mode (HPLC‐DAD‐CAD–MS) .…”