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Agrimony pilosa Ledeb. (Rosaceae) - Chemical Composition, Biological Effects and Anatomy
Abstract
Two fractions of polysaccharide have been extracted by the method of sequential extraction from the underground part of the plant; the monomeric composition of these fractions has been defined by the acid hydrolysis of these fractions and the following application of paper chromatography. The anatomy structure of Agrimonia pilosa Ledeb rootstocks and roots has been researched by the method of light microscopy. The fascicular rootstock structure has been defined; the primary and secondary roots structures have been described.
... Nowadays, The AP is routinely applied on the treatment of diseases, such as stomatitis, hepatitis, enteritis, hematischesis and nephritis caused by bacteria and virus infection. It has also been used as an anti-inflammatory agent in Bulgaria and Great Britain, as anti-parasitic in Korean medicine, as a hemostatic agent in China and Vietnam medicine [10] . ...
... Kaempferol-3-O-glucoside Flavonoid [1] 12 Rutin Flavonoid [13] 13 Apigenin Flavonoid [13] 14 Apigenin-7-O-β-D-glucoside Flavonoid [12] 15 Apigenin-7-O-β-D-glucuronide Flavonoid [12] 16 Agriflavone Flavonoid [12] 17 Luteolin Flavonoid [10] 18 Luteolin-7-O-β-D-glucopyranoside Flavonoid [10] 19 Luteolin-7-O-β-D-glucoside Flavonoid [12] 20 Luteolin-7-O-β-D-glucuronide Flavonoid [12] 21 Luteolin-7-O-β-D-glucuronide methyl ester Flavonoid [12] 22 Luteolin-7-O-β-D-glucuronide butyl ester Flavonoid [12] 23 ...
... Kaempferol-3-O-glucoside Flavonoid [1] 12 Rutin Flavonoid [13] 13 Apigenin Flavonoid [13] 14 Apigenin-7-O-β-D-glucoside Flavonoid [12] 15 Apigenin-7-O-β-D-glucuronide Flavonoid [12] 16 Agriflavone Flavonoid [12] 17 Luteolin Flavonoid [10] 18 Luteolin-7-O-β-D-glucopyranoside Flavonoid [10] 19 Luteolin-7-O-β-D-glucoside Flavonoid [12] 20 Luteolin-7-O-β-D-glucuronide Flavonoid [12] 21 Luteolin-7-O-β-D-glucuronide methyl ester Flavonoid [12] 22 Luteolin-7-O-β-D-glucuronide butyl ester Flavonoid [12] 23 ...
Agrimonia pilosa Ledeb (Rosaceae, AP) has long been used as a widely herbal medicine in Asian countries for treatment of various diseases. AP contains many valuable secondary metabolites, such as flavonoids, triterpenoid, phenols and phenolic acids and has antioxidant, antibacterial, antiviral, anti-tumor, anti-diabetic properties and effects on alzheimer’ s disease. In the recently decades, a series of analytical methods have been developed to evaluate the quality of AP based on its bioactive components. This review aims to present an up-to-date and comprehensive overview of the ethnopharmacology, phytochemistry and pharmacology of AP, which should be useful for the greater development of AP, especially in the development of new drugs and therapeutics for various diseases.
... The chromatogram of the total flavonoid extracted from the A. pilosa Ledeb is shown in Figure 1. Compared with the mass spectrum data and literatures, 10 flavonoid compounds were found in the total flavonoid extracted from the A. pilosa Ledeb, including apigenin [22], kaempferol [23], kaempferol-3-O-glucoside [24], luteolin [25], quercetin [26], taxifolin [27], tiliroside [28], isoquercetin [29], rutin [27], and vitexin [30] (Table S1). The total ion chromatogram of the total flavonoid is available in the Supplementary Materials ( Figure S1). ...
(1) Background: Methicillin-resistant Staphylococcus aureus (MRSA) is a zoonotic pathogen that causes endocarditis, pneumonia, and skin diseases in humans and livestock. (2) Methods: The antibacterial effect of the total flavonoid against MRSA (ATCC43300) extracted from the Agrimonia pilosa Ledeb. (A. pilosa Ledeb) was evaluated by the microdilution method. The oxidative stresses in MRSA were evaluated by the levels of intracellular hydrogen peroxide (H2O2), reactive oxygen species (ROS), and oxidative stress-related genes. The DNA oxidative damage was tested by the 8-hydroxy-2′-deoxyguanosine (8-OHdG) and DNA gel electrophoresis. The differentially expressed proteins were determined by the method of SDS-PAGE and NanoLC-ESI-MS/MS, while the mRNAs of differential proteins were determined by Real-Time PCR. The changes of ultra-structures in MRSA were observed by Transmission Electron Microscope (TEM). (3) Results: The minimum inhibitory concentration (MIC) of the total flavonoid against MRSA was recorded as 62.5 μg/mL. After treatment with the total flavonoid, the levels of intracellular H2O2 and ROS were increased and the gene expressions against oxidative stress (SodA, katA, TrxB) were decreased (p < 0.01), while the gene expression for oxidative stress (PerR) was increased (p < 0.01). The level of intracellular 8-OHdG in MRSA was increased (p < 0.01) and the DNA was damaged. The results of TEM also showed that the total flavonoid could destroy the ultra-structures in the bacteria. (4) Conclusions: The total flavonoid extracted from the A. pilosa Ledeb can induce the oxidative stress that disturbed the energy metabolism and protein synthesis in MRSA.
The antitumor activities of various extracts from the roots of Agrimonia pilosa LEDEB. were studied. Each extract was given intraperitoneally to mice once at 4 d before the intraperitoneal inoculation of mouse mammary carcinoma MM2 cells, and the non-sugar fractions with median polarity showed antitumor activity. Agrimoniin was isolated from the antitumor active fractions. Agrimoniin itself showed antitumor activity when given as a pre- or posttreatment ; a single dose of 10 to 30 mg/kg of agrimoniin resulted in almost complete rejection of the tumor by the test mice. Agrimoniin also possessed a high degree of cytotoxicity but this activity was significantly reduced by the addition of serum to the culture medium.
A new phenolic lactone, m.p. 173.5°, was isolated from the fresh subterranean part of Agrimonia pilosa LEDEB. and was named agrimonolide (I). Molecular formula of (I) agrees with C18H18O5, possessing one methoxyl and two phenolic hydroxyls, one of which is chelated to a lactonic C=O and is not easily methylated. It is a γ- or δ- lactone and the acid obtained on cleavage of the lactone ring easily undergoes decarboxylation to form a compound of m.p. 169°, C17H20O4, which was named agrimonol.
Bromination of (I) easily afforded a dibromo (VI) and tribromo (VII) derivatives, while oxidation of (I) and (VI) gave anisic acid (VIII). Oxidation of (VII) afforded 3-bromo-4-methoxybenzoic acid. Oxidation of the dimethyl derivative of (I) formed anisic acid and 3, 5-dimethoxyphthalic acid (XIII). Since potassium salt of the acid obtained on lactone-cleavage of (IV) is levorotatory, it is clear that asymmetric carbon is present in (I). There is no C-methyl group in (I). It was thereby concluded that the structure of agrimonolide would correspond to one of the formulae (XVI), (XVII), and (XVIII).
Potentillin (3), which has an α-glucosyl linkage, and its dimer, agrimoniin (1) have been isolated from Agrimonia pilosa ledeb. and Potentilla kleiniana Wight et Arnott., and their structures elucidated.
Phytochemical investigation of the methanolic extract from the aerial parts of Agrimonia pilosa led to the isolation of three compounds, (-)-aromadendrin 3-O-β-D-glucopyranoside, desmethylagrimonolide 6-O-β-D-glucopyranoside, and 5,7-dihydroxy-2-propylchromone 7-O-β-D-glucopyranoside, together with nine known compounds, agrimonolide 6-O-glucoside, takanechromone C, astragalin, afzelin, tiliroside, luteolin, quercetin, isoquercetrin, and quercitrin. Their structures were determined by various spectroscopic analysis and chemical transformations.
To study the chemical constituents in Agrimonia pilosa.
The compounds were isolated and purified by various column chromatographic methods and elucidated on the basis of chemical and spectroscopic evidences.
Nine flavonoids were obtained and identified as tiliroside (1), kaempferol 3-O-alpha-L-rhampyranoside (2), quercetin 3-O-alpha-L-rhampyranoside (3), quercetin 3-O-beta-D-glucopyranoside (4), kaempferol 3-O-beta-D-glucopyranoside (5), kaempferol (6), apigenin (7), luteolin (8), quercetin (9).
Compounds 1-3, 5, 6 and 8 were isolated from this plant for the first time.
Five compounds were isolated from the petroleum ether extract of the root-sprouts of Agrimonia pilosa Ledob. A new compound, (R)-(-)-agrimol B (III), was elucidated by means of physical and chemical properties, spectroscopy (MS, IR, PMR, UV) and total synthesis. Four known compounds were identified as agrimophol (I), n-nonacosane (II), beta-sitosterol (IV) and pseudo-aspidin (V), the last one being previously known only as a synthetic entity. (S)-(+)-Agrimol B also was synthesized.
Two flavonoid glucosides were isolated from the stems and leaves of Agrimonia pilosa LEDEBOUR var. japonica NAKAI (Rosaceae), which did not yet bear any flower, by 6-Nylon column chromatography and were identified as luteolin 7-β-D-glucoside and apigenin 7-β-D-glucoside by mixed fusion and IR spectra. Its whole herb is in general called Ryugeso.