Isolation of Chemical Compounds and Essential Oil from Agrimonia asiatica Juz. and Their Antimicrobial and Antiplasmodial Activities

Agrimonia asiatica is a perennial plant with deep green color and covered with soft hairs and has a slightly aromatic odor. This genus Agrimonia has been used in traditional medicines of China, Greece, and European countries. It was mainly used as a haemostatic, a tonic for asthenia, and an astringent for diarrhea. Agrimony is part of the division Magnoliophyta; class is represented by order Rosales, family Rosaceae, of the genus Agrimonia. Family Rosaceae—or pink eels—is one of the largest families of flowering plants, including about 100 genera and 3000 species. Rosaceae is common in almost all areas of the globe where flowering plants can grow, but most of them are concentrated in the temperate and subtropical zones of the Northern Hemisphere. Phytochemical investigation on ethanolic extract of A. asiatica led to isolation of four flavonoid derivatives (kaempferol-3-glycoside, quercetin-3-O-α-arabinofuranosyl-β-D-galactopyranoside, 3-O-kaempherol 2,3-di-O-acetyl-4-O-(cis-p-coumaroyl)-6-O-(trans-p-coumaroyl)-β-D-glucosopyranoside, and catechin) alongside of sucrose. All the extracts, fractions, and isolated compounds were tested for antimicrobial and antiplasmodial activities. We also studied the chemical composition of essential oil obtained from the aerial part of A. asiatica. The essential oil constituents from the aerial part of A. asiatica were obtained using a steam-distillation method in wild growing conditions in Kazakhstan. The essential oil extracted from the aerial part of the plant was analyzed by gas chromatography-mass spectroscopy and its major components amounting to 100% were found to be β-selinene (36.370%), α-panasinsene (21.720%), hexadecanoic acid (7.839%), and 1,2-nonadiene (6.199%). Neither the extract nor the isolated compounds showed antimicrobial and antiplasmodial activities.


Introduction
Asian agrimony (Agrimonia asiatica Juz.) is a perennial herb reaching a height of up to 140 cm, rhizomatous, erect stem, densely dressed, like leaf stalks, long, stiff hairs with an admixture of shorter and softer hairs. e leaves are green above, below grayish-green, broken-pinnate, from top to bottom slightly pubescent, velvety-pubescent with a mixture of small pieces of iron. e flowers are yellow, collected in spike-shaped inflorescences. e fruits are drooping; the Catechin [13] 2 e Scientific World Journal upper surface of the fruit is convex, with spines arranged in several rows, of which the outer spines are shorter than the inner ones. A. asiatica is rich in polysaccharides and glycosides which grows in Central Asia and widely used in folk medicine to prevent and cure diseases connected with gastrointestinal tract, in high blood pressure, and as immunostimulant, astringent. It grows on the slopes of mountains, ditches, gardens, along roads, and on the edges of birch forests, walnut forests. It blooms in June-July. Phytochemical composition of Agrimonia genus includes mainly polysaccharides up to 20% and tannins in the range of 3.1-10.8% [1]. In Kazakhstan, A. asiatica extracts were found to have antioxidant activity [2]; suppression of plasma GR activity and an alloxan-induced increase in erythrocyte GP activity were encountered [3]. Previous investigation on essential oil composition of this genus plants A. eupatoria, A. pilosa wild leaves were reported to have caryophyllene, caryophyllene oxide, humulene, and E-farnesene, and in the cultivated leaves oil α-pinene, β-caryophyllene, E-β-farnesene, and cumin aldehyde were found [4,5]. However, this is the first report on essential oil composition from this plant. In continuation to our previous work on essential oil composition of Kazakhstan medicinal plants [6], we were interested to continue working on A. asiatica. Agrimoniin was first isolated in 1982 from roots of A. pilosa, a plant traditionally used in Japan and China as an antidiarrheal, haemostatic, and antiparasitic agent. Agrimoniin is a constituent of medicinal plants, which are often applied orally in the form of infusions, decoctions, or tinctures. It is also present in commonly consumed food products, such as strawberries and raspberries. It is metabolized by human gut microbiota into a series of low-molecular-weight urolithins with proven anti-inflammatory and anticancer in vivo and in vitro bioactivities. Agrimoniin is an important component of plants belonging to the Rosaceae family, which have been used since antiquity in traditional medicine to treat a variety of ailments. Owing to a series of highly interesting activities described in detail, agrimoniin is an attractive research candidate for a full exploration of its therapeutic effects [7]. After drying, the raw material was chopped till 3-4 mm using laboratory mill IKA M20.

Antimicrobial and Antiplasmodial
Activities. e extract and isolated compounds were screened for antimicrobial and antiplasmodial activities using the reported methods by [8,9].

Result and Discussion
Phytochemical investigation on ethanolic extract of Agrimonia asiatica led to isolation of four flavonoid derivatives. All the isolated compounds were identified by analyzing their spectral data analysis as follows: (3), catechin (4), and sucrose (5) (see Tables 1-5 and their NMR spectra given in Supplementary Materials Figures 1-19).
All the extracts, fractions, and isolated compounds were tested for antimicrobial and antiplasmodial activities. None of the extracts and isolates exhibited significant activity (see Tables 6 and 7). e oil components were identified by comparing their mass spectra with the NIST Library as well as with authentic compounds.
is was confirmed by comparison of their retention indices with those of authentic compounds as well as with data published in the literature [14]. e identified compounds, their retention indices, and their percentage compositions were summarized in Table 8.

Data Availability
e data used to support the findings of this study are included within the article.