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Article

Study of the Chemical Composition of Rosa beggeriana Schrenk’s Fruits and Leaves

by
Aigerim Aituarova
1,*,
Galiya E. Zhusupova
1,
Aizhan Zhussupova
2 and
Samir A. Ross
3,4
1
Department of Chemistry and Technology of Organic Substances, Natural Compounds and Polymers, NPJSC Al-Farabi Kazakh National University, Al-Farabi Ave. 71, Almaty 050040, Kazakhstan
2
Department of Molecular Biology and Genetics, NPJSC Al-Farabi Kazakh National University, Al-Farabi, Ave. 71, Almaty 050040, Kazakhstan
3
School of Pharmacy, University of Mississippi, P.O. Box 1848, Oxford, MS 38677, USA
4
School of Pharmacy, S.D. Asfendiyarov Kazakh National Medical University, Almaty 050000, Kazakhstan
*
Author to whom correspondence should be addressed.
Plants 2023, 12(18), 3297; https://doi.org/10.3390/plants12183297
Submission received: 9 August 2023 / Revised: 7 September 2023 / Accepted: 9 September 2023 / Published: 18 September 2023
(This article belongs to the Special Issue Valuable Sources of Bioactive Natural Products from Plants)
Browse Figures
Versions Notes

Abstract

:
Rosa species are widely used in folk medicine in different countries of Asia and Europe, but not all species are studied in-depth. For instance, Rosa beggeriana Schrenk, a plant which grows in Central Asia, Iran, and some parts of China, is little described in articles. Column and thin-layer chromatography methods were used to isolate biologically active substances. From a study of fruits and leaves of Rosa beggeriana Schrenk, a large number of compounds were identified, seven of which were isolated: 3β,23-dihydroxyurs-12-ene (1), β-sitosterol (2), betulin (3), (+)-catechin (4), lupeol (5), ethyl linoleate (6), and ethyl linolenoate (7). Their structures were elucidated by 1H, DEPT and 13C NMR spectroscopy, mass spectrometry, and GC-MS (gas chromatography–mass spectrometry). The study also identified the structures of organic compounds, including volatile esters and acids. Consequently, comprehensive data were acquired concerning the chemical constitution of said botanical specimen.

1. Introduction

The genus Rosa holds big commercial significance and is renowned in the domain of folk medicine. Numerous wild species within this genus have played a pivotal role in the development of valuable and economically viable cultivars of ornamental roses [1]. Despite the relative under-examination of certain rose species, several of them possess significant potential due to the presence of rosehip fruits. Commercially traded rosehip fruit is derived from several different species. They are long-lived woody perennials found mainly on forest margins and in disturbed habitats, such as roadsides and open fields. The genus Rosa (Rosaceae) has around 150–200 species [1,2,3]. Roses have also been cultivated since ancient times as medicinal plants in many countries across Europe and Asia. Rosehips contain many pharmacologically active compounds, such as organic acids, vitamin C and E, flavonoids, carotenoids, and tannins. Therapeutic properties and benefits of rosehips are their nourishing, mild laxative, mild diuretic, mild astringent, diuretic, ophthalmic and tonic effects [1,4,5,6]. Rosa extracts derived from these plants are also widely used in cosmetics, promising antioxidant and moisturizing effects [1,5,6,7,8]. All parts of this wild rose have been used in Asian folk medicine [4,5,9,10,11].
The intrinsic value of rosehip fruit has been acknowledged for centuries; however, efforts have only recently been made to domesticate and cultivate wild roses specifically for their fruit and to advance agronomic techniques in this regard. This shift in focus can be attributed to an enhanced comprehension of the pivotal role that dietary fruits play in enhancing human health and mitigating disease risks [12]. The Rosaceae family is one of the most employed as a consolidated source of phytoproducts with functional properties [13]. Within this family, the genus Rosa provides various species, and their essential oils possess a wide range of applications as flavor, fragrance, and additive in cosmetic and toiletries [14]. In addition to their aromatic composition, many Rosa species from all over the word have been evaluated for their food-related biological properties and multiple functional uses have been suggested [15,16,17,18,19]. For example, teas made from the fruits of Rosa canina have mild laxative and diuretic tendencies [12]. Rosehips have a longstanding history of utilization in folk medicine spanning centuries, primarily for the prevention and treatment of various ailments such as the common cold, influenza-like infections, fever, infectious diseases, vitamin C deficiency, general exhaustion, gastritis and gastric ulcers prevention, diarrhea, gallstones and gallbladder discomforts, urinary tract diseases and discomforts, as well as for their potential anti-inflammatory, anti-obesity, anticancer, and diabetes management properties. Furthermore, rosehips have been employed to address inadequate peripheral circulation concerns [5,6,15,16,17,18,20,21]. Mixed with small amount of vinegar, rosehips were used as an antidote for the treatment of iron toxicity [20,22]. For nutritional purposes, fruits are used for the production of different products like tea, marmalade, jam, stewed fruit, wine, and juices [23]. Ground in a hand mill and cooked with milk, they could be used as children’s snack and baby food as reported by the latter authors. The functional properties of some Rosa species are attributable to a wide range of bioactive ingredients, such as minerals, flavonoids, tannins, anthocyanin, organic acids, phenolic compounds fatty acids, volatile oils, ascorbic acid, phenols, and sugar. Through the examination of a species within the same taxonomic family as the subject of investigation, co-occurring within the identical geographical region, it becomes feasible to assess the potential anticancer properties of compounds derived from Begger’s rosehip [5,24,25,26,27,28].
Rosa beggeriana Schrenk is an indigenous species predominantly distributed in Central Asia (Kazakhstan, Kyrgyzstan), China (Xinjiang Uygur Autonomous Region), and Iran [29,30,31,32,33]. It has been identified as an essential resource for hybridization purposes, particularly in the development of cold-resistant germplasm, when combined with contemporary rose varieties [29]. Begger’s rosehip contains a large number of compounds with antioxidant activity, including activity against cancer cells. Rosehip hips have a high concentration of the carotenoid lycopene, which is considered a compound with a powerful antioxidant effect and is used as a therapeutic and prophylactic agent for various diseases, including cancer. Begger’s rosehip extracts display cytotoxicity and antiproliferative properties against human liver and breast cancer cells, which might be associated with the presence of polyphenols in it [34].
According to the studies mentioned earlier, we can tell that Begger’s rosehips have not been studied sufficiently even though other species are very well known in the folk medicine of different countries.

2. Results

2.1. Identification of the Isolated Compounds from Leaves of Rosa beggeriana Schrenk

Utilizing column chromatography, a total of seven distinct substances were successfully isolated from both the fruits and leaves of the wild rose species known as Begger (Rosa sp.). The isolated substances encompassed a diverse range of chemical classes, including triterpenoids, catechins, and fatty acid esters. Remarkably, 3β,23-dihydroxyurs-12-ene had not been previously reported in this particular plant species. Additionally, no NMR characterization data were available for this newly isolated substance [35,36,37]. Apart from this novel isolate, the triterpenoids, catechins, and a mixture of fatty acid esters were also successfully identified and isolated from the aforementioned plant material.

2.2. GC-MS Data

GC-MS analysis was used to obtain data on the fatty acid composition of the leaves (Table 1) and fruits (Table 2) of Rosa beggeriana Schrenk.
When comparing the two tables, a richer composition of the fatty acids in fruits can be observed (Table 1 and Table 2).

2.3. NMR Data

2.3.1. Identification of the Isolated Compounds from Leaves of Rosa beggeriana Schrenk

From the ethanol extract (45 g) of Rosa beggeriana Schrenk (553 g), 3β,23-dihydroxyurs-12-ene (1) [35,36,37] (21 mg) was isolated. The chemical structures are shown in Figure 1.
NMR data for Compound 1 were not found in literature. Hence, the analysis of the NMR spectra (Figures S1–S4) and the comparison of the spectroscopic data (Table 3) with those compounds that have a similar structure and described in the literature [35,36,37] allowed the identification of the compound 1. The mass spectra also allowed us to identify compound 1. Also, the melting point for compound 1 was 226–229 °C.
From the ethanol extract (45 g) of Rosa beggeriana Schrenk (553 g), betulin (3) [38,39] (42.5 mg) and (+)-catechin (4) [40,41,42] (40.0 mg) were isolated. The chemical structures are shown in Figure 2.
Compound 3 (betulin) was identified by its characteristic 1H NMR (400 MHz; CDCl3) δ: 1.57, 1.27 (2H, s, H-1), 1.70 (2H, s, H-2), 3.21 (2H, dd, H-2), 0.96 (1H, s, H-5), 1.38 (2H, s, H-6), 1.57, 1.38 (2H, s, H-7), 1.38 (2H, s, H-11), 1.38 (2H, s, H-12), 1.57, 1.27 (2H, s, H-15), 1.57, 1.27 (2H, s, H-16), 1.92 (1H, m, H-19), 1.57, 1.27 (2H, s, H-21), 1.57, 1.27 (2H, s, H-22), 0.78 (3H, s, H-24), 0.81 (3H, s, H-25), 0.96 (3H, s, H-23), 0.99 (3H, s, H-27), 1.05 (3H, s, H-26), 1.70 (3H, s, H-30), 3.20 (d, H-28a), 3.65 (d, H-28b), 4.58 (dd, H-29a), 4.71 (d, H-29b). 13C NMR (CDCl3) δ: 38.73 (C-1), 27.41 (C-2), 79.01 (C-3), 38.73 (C-4), 55.32 (C-5), 18.34 (C-6), 34.30 (C-7), 40.84 (C-8), 50.45 (C-9), 37.18 (C-10), 20.95 (C-11), 25.15 (C-12), 37.18 (C-13), 42.84 (C-14), 27.41 (C-15), 29.39 (C-16), 47.99 (C-17,C-19), 48.31 (C-18), 150.94 (C-20), 29.73 (C-21), 33.30 (C-22), 28.01 (C-23), 15.40 (C-24), 16.14 (C-25), 15.99 (C-26), 14.57 (C-27), 63.67 (C-28), 109.36 (C-29), 16.00 (C-30) (Figures S7–S14), all in agreement with values in the literature [39,43]. The melting point of compound 3 was 248–250 °C.
For compound 4 (m.p.175–177 °C, optical rotation [α]D +17.2°), a detailed analysis of the NMR data led to the proposed structure, confirmed by the analysis of the spectra and comparison of the NMR resonances (Figures S15–S18) with the literature data summarized in the Table 4 [40].

2.3.2. Identification of the Isolated Compounds from Fruits of Rosa beggeriana Schrenk

β-sitosterol (2), lupeol (5), ethyl linoleate (6), and ethyl linolenoate (7) were isolated from the ethanol extract (35 g) of Rosa beggeriana Schrenk (400 g). The chemical structures are shown in Figure 3.
Compound (2) was identified as β-sitosterol (Figures S5 and S6) according to the literature [44,45].
Lupeol (5) (m.p. 215–218°C): (Figures S19–S21) 1H NMR (CDCl3) δ: 0.77 (3H, s, H-24), 0.80 (3H, s, H-28), 0.84 (3H, s, H-25), 0.96 (3H, s, H-23), 0.98 (3H, s, H-27), 1.04 (3H, s, H-26), 1.69 (3H, s, H-30), 4.58 (1H, s, H-29a), 4.70 (1H, s, H-29b). 3.19 (1H, dd, H-3); 13C NMR (CDCl3, 400 MHz): δ 150.92 (C-20), 109.37 (C-29), 78.99 (C-3), 55.32 (C-5), 50.45 (C-9), 48.31 (C-18), 47.99 (C-19), 43.01 (C-17), 42.84 (C-14), 40.84 (C-8), 40.02 (C-22), 38.87 (C-13), 38.73 (C-4), 38.06 (C-1), 37.18 (C-10), 35.60 (C-16), 34.30 (C-7), 29.86 (C-21), 28.01 (C-23), 27.46 (C-15), 27.40 (C-12), 25.15 (C-2), 20.95 (C-11), 19.33 (C-30), 18.34 (C-6), 18.03 (C-28), 16.14 (C-25), 16.00 (C-26), 15.40 (C-24), 14.57 (C-27) [39,41,46,47]. Optical rotation [α]D +27.1°.
The analysis of the NMR spectra (Figures S22–S28) and the comparison of the spectroscopic data with those described in the literature allowed the identification of the mixture of two fatty acids known as ethyl linoleate (6) and ethyl linolenoate (7), and GC-MS helped to verify the accuracy of our assumptions. 1H NMR (CDCl3) δ: 2.30 (2H, t, H-2), 1.63 (2H, t, H-3), 1.35 (14H, s, H-4, 5, 6, 7, 15, 16, 17), 2.07 (4H, m, H-8, 14), 5.41— 5.30 (4H, m, H-9, 10, 12, 13), 2.77 (2H, t, J_7.0 Hz, H-11), 5.37 (4H, m, H-9, 10, 12, 13), 4.14 (2H, m, –OCH2–), 0.90 (3H, t, H-18) 1.26 (3H, m, H-20). 13C NMR: 174.06 (C-1), 33.76 (C-2) 25.21 (C-3) 26.84(C-4) 29.32 (C-5) 29.45 (C-6) 29.45 (C-7) 27.84 (C-8) 131.36(C-9) 129.49 (C-10) 25.81 (C-11) 129.56(C-12) 129.69 (C-13), 28.81(C-14) 29.45 (C-15) 31.74 (C-16) 22.40 (C-17) 59.97 (–OCH2–) 13.24 (C-18) 14.35 (C-20) [48].

3. Discussion

3.1. GC-MS Data

The GC-MS analysis uncovered a heterogeneous chemical composition encompassing various classes of volatile compounds, which has been meticulously documented and organized in Table 1 and Table 2. Considering the paucity of scholarly investigations on the phytochemical composition of R. beggeriana, the GC-MS data were juxtaposed with data obtained from other species belonging to the Rosa genus, as cited in [49,50,51,52]. The comparative analysis of compositions, specifically the leaves and fruits, revealed a higher degree of complexity in the composition of the latter. It is noteworthy that this study represents the inaugural examination of the fatty acids’ profiles pertaining to this plant species.
Table 1 presents the GC-MS data in the analysis of fractions L-2-1, L-2-11, L-2-27, CH-21, CH-39, and HIJK obtained from leaves of R. beggeriana. The richest one was L-2-11—n-hexane/ethyl acetate fraction (6/4).
The composition of leaves was found to include various compounds such as terpenoids, specifically (-)-aristolene, as well as phytosterols like stigmastan-3,5-diene. Additionally, saturated and unsaturated fatty acids, along with their corresponding esters, were identified. The majority of the fatty acids detected exhibited unsaturation, including 9-hexadecenoic acid methyl ester (Z)-, 9,12-octadecadienoic acid (Z,Z)-methyl ester, 9,12,15-octadecatrienoic acid methyl ester (Z,Z,Z)-, methyl linoleate, methyl linolenate, methyl elaidate, 9-octadecenoic acid methyl ester (E)-, 9-octadecenoic acid (Z)- methyl ester, 9,12,15-octadecatrienoic acid (Z,Z,Z)-, and cis-13-eicosenoic acid methyl ester.
The GC-MS data obtained from the analysis of ethanol extract (B) and various fractions (B-1, B-2, B-3, B-4, B-5, B-DCM, B-M1-16, B-M2-18, 26-A, 26-S8) derived from R. beggeriana fruits are presented in Table 2. Among these fractions, the most abundant one was B-4, which corresponded to the chloroform/ethyl acetate fraction with a ratio of 1:1.
The fruits of the plant exhibited a comprehensive array of both saturated and unsaturated fatty acids, along with their respective esters. Moreover, several additional fatty acids were identified, including myristic acid, palmitic acid, palmitoleic acid, ethyl linoleate, (e)-9-octadecenoic acid ethyl ester, ethyl oleate, alpha-linolenic acid, 11-octadecenoic acid (z)-, 11-octadecenoic acid (e)-, oleic acid (z)-, stearic acid, 9,12-octadecadienoic acid (z,z)-, and 2-hydroxy-1-(hydroxymethyl)ethyl ester. The abundance of unsaturated fatty acids in the composition of the fruits holds significant potential for application in the food industry.
In addition, the fruits were found to encompass phytosterols such as beta-sitosterol, gamma-sitosterol, stigmastan-3,5-diene, gamma-tocopherol, and lupeol.
Upon comprehensive analysis of the collective findings presented in Table 2 and Table 3, it becomes evident that both the leaves and fruits of R. beggeriana exhibited a substantial abundance of saturated and unsaturated acids, terpenoids, and various other substances. These results collectively indicate a highly diverse and rich composition within the examined plant components.

3.2. Isolation and Identification of Individual Compounds

Identification of the isolated compounds (1–5) was based on spectroscopic analyses (1H, DEPTQ, DEPT135, 13C NMR) compared with the data published in the literature.
In this study, the presence of 3β,23-dihydroxyurs-12-ene (compound 1—white and crystalline) in the leaves of R. beggeriana was established and confirmed using NMR data analysis, coupled with relevant literature sources [35,36,37]. A structurally similar compound, 3β,24-dihydroxyurs-12-ene, had been previously isolated from Protium heptaphyllum. By comparing the 1H- and 13C-NMR spectra of the two compounds, it was observed that all peaks were identical, except for those corresponding to C-23 and C-24. For 3β,23-dihydroxyurs-12-ene, the chemical shifts for C-23 and C-24 were 63.0 and 15.6 ppm, respectively, whereas for 3β,24-dihydroxyurs-12-ene, these values were reversed [35]. The presence of an oxygen moiety at C-23 in 3β,23-dihydroxyurs-12-ene was deduced based on the chemical shift at 63.0 ppm. The 1H-NMR spectrum displayed signals corresponding to seven methyl groups: 1.25 (H-24), 0.98 (H-25), 1.02 (H-26), 1.08 (H-27), 0.81 (H-28), 0.80 (H-29), and 0.81 (H-30). The 13C-NMR spectrum exhibited two peaks at 124.4 (C-12) and 139.5 (C-13), indicating the presence of a double bond in the ring. Overall, the number of observed peaks suggested the presence of 30 carbon atoms in compound 1. Importantly, this study represents the first isolation of 3β,23-dihydroxyurs-12-ene from the Rosa genus. Compound 1 was further compared to 3β,28-dihydroxyurs-12-ene, which contained a -CH2OH group at the 28th carbon atom, resulting in a chemical shift of 69.20 ppm. Consistent correlations were observed in the 1H-NMR spectra, supporting the structural analysis. High-resolution mass spectrometry (HR MS), as depicted in Figure S4, furnishes valuable insights pertaining to the molecular attributes of the compound under investigation. Specifically, it elucidated a molecular weight of 442 m/z, thereby affording a comprehensive breakdown of constituent particles within this compound. For instance, it is reasonable to deduce the presence of two highly mobile hydrogen atoms (m/z 440). Furthermore, the observation of protonation events at 424 [M + H2O]+ and 406 [M + H2O]+ suggests the existence of two hydroxyl (-OH) groups.
In addition, the HR MS data imitate the potential stability of a fragment with an m/z value of 273, indicative of a cleavage point that partitions the molecule into two relatively stable subunits. Moreover, the ensuing particles predominantly originated from the cleavage of the molecule at the central region of its third ring, yielding fragments with m/z values of 133, 189, 203, and 234. These findings contribute to a more intricate understanding of the compound’s structural composition and fragmentation pattern. Notably, structurally related compounds (although not identical) [37,43,53,54] have been identified within the Rosa family, specifically in the fruits of R. multiflora and the roots of R. taiwanensis, and have been associated with anti-inflammatory activity. Based on the available data, it is plausible to postulate that 3β,23-dihydroxyurs-12-ene may possess similar activities to those of the structurally related compounds mentioned earlier. However, further investigation and experimental studies are necessary to validate and ascertain its potential biological activities. This compound have potential for use in medicine because there many studies of almost structurally identical compounds that have different types of activities [37,55,56].
Betulin (3) and (+)-catechin (4) have been identified in various Rosa species, present not only in leaves, but also in the roots, stems, with (+)-catechin present in the fruits and flowers [43,57,58,59]. The identification of compound 3 (betulin—solid and white crystalline) was accomplished through the analysis of its characteristic 1H NMR (400 MHz; CDCl3) and 13C NMR (CDCl3) spectra. The carbon peaks were meticulously examined, revealing the presence of 30 carbon atoms in this compound. Utilizing the DEPT135 method, it was determined that betulin comprises 12 -CH2 groups, 5 unhydrolyzed carbons (because we can see them in 13C NMR spectra but not there), 13 -CH3 and/or -CH groups, two oxygenated carbons (63.06 and 79.01), and one double bond (109.35). Proton magnetic resonance spectra further confirmed these structural features. Specifically, the 1H NMR spectra exhibited signals corresponding to six methyl groups: 0.78 (3H, s, H-24), 0.81 (3H, s, H-25), 0.96 (3H, s, H-23), 0.99 (3H, s, H-27), 1.05 (3H, s, H-26), and 1.70 (3H, s, H-30). Additionally, signals of methylene groups were observed at 1.57, 1.27 (2H, s, H-1), 1.70 (2H, s, H-2), 3.21 (2H, dd, H-2), 1.38 (2H, s, H-6), 1.57, 1.38 (2H, s, H-7), 1.38 (2H, s, H-11), 1.38 (2H, s, H-12), 1.57, 1.27 (2H, s, H-15), 1.57, 1.27 (2H, s, H-16), 1.57, 1.27 (2H, s, H-21), 1.57, and 1.27 (2H, s, H-22). Based on the data presented in Figures S10–S14, encompassing 2D nuclear magnetic resonance (NMR) and gas chromatography-mass spectrometry (GC-MS) spectra, it is discernible that compound 3 corresponds to betulin. The GC-MS spectra provides essential information such as the retention time and molecular weight of this compound. Additionally, compound (+)-catechin (4) has been identified through a combination of NMR analysis, which was previously elucidated, and mass spectrometry. The mass spectra of compound 4 exhibited a discernible molecular weight of approximately 290 units. This determination is in accordance with our NMR-based assumption of it being catechin. Notably, the mass spectra also revealed distinct ions with molecular weights of 110, 138, and 55 units. These observations are congruent with the structural features of catechin, particularly with regard to the presence of vulnerable chemical bonds in its structure. Betulin was isolated from the roots of Rosa taiwanensis [43], and catechin was reported in the roots of R. taiwanensis [43], rosehips of Rosa canina [57,58]. Notably, betulin was reported to have anti-inflammatory and anticancer properties [60]. The structural identification of (+)-catechin (4) was established based on the analyses of the 1H NMR, DEPT135, and 13C NMR signals.
The NMR data of β-sitosterol (2) were subjected to a comprehensive comparison with relevant literature data [44,45,61].
Lupeol (5) is a triterpenoid that was found in the fruits of R. beggeriana and identified through comparison with NMR data from the literature data [39,46,47]. R. rugosa was also reported to have lupeol [62]. Using carbon nuclear magnetic resonance, it was found that the compound had 30 carbon atoms, 10 of which were methylene groups. The presence of a hydroxyl group and a double bond due to the presence of a shift was also established. Also, thanks to proton magnetic resonance, it was possible to establish the structure by calculating the number and area of peaks.
Ethyl linoleate (6) and ethyl linolenoate (7) were isolated together, and structure was elucidated by GC-MS data (Figures S21 and S22) and NMR, which were compared to literature [48].
Regardless of the precise study of several species, like R. canina, R. rugosa, and others, there are many species in the Rosa genus with minimal data. Many species of the Rosa family grow in diverse conditions, hence they can have different chemical composition [1,4,5].

4. Materials and Methods

4.1. Plant Material

The plant was harvested at a 23–25 °C temperature near Ili River and in the Almaty oblast N44°79.3959, E76°29.8245 in September 2021, by a biologist employee of the Botanical Garden in Almaty, Madina Ramazanova. Then, the plant was dried in the drying cabinet at 35 °C for 6 h and 48 h at room temperature, And it was deposited at the herbarium collection at the Institute of Botany and Phytointroduction of the Ministry of Higher Education and Science, Almaty, Kazakhstan (0002540).

4.2. General Experimental Procedures

Solvents used in this work, n-hexane, chloroform, dichloromethane (DCM), ethyl acetate (EtOAc), methanol (MeOH), and ethanol (EtOH), were purchased from Fisher Scientific, Waltham, MA USA. Deuterated solvents (Sigma-Aldrich, Darmstadt, Germany), including methanol (MeOD) and chloroform (CDCl3), were used for nuclear magnetic resonance (NMR) spectroscopic analyses. Column chromatography (CC) was performed using silica gel 60 (0.063–0.200 mm; Merck, Darmstadt, Germany) or Sephadex LH-20 (0.25–0.1 mm, GE Healthcare, Cytiva, Sweden). Vacuum liquid chromatography column (VLC) (diameter 15 cm × length 30 cm, 300 g) at room temperature was used to isolate substances from five main fractions. Thin-layer chromatography (TLC) analyses were carried out using pre-coated silica G plates w/UV254 (20 cm × 20 cm, 200 µm in thickness; Sorbent Technologies, Norcross, GA, USA). An ultraviolet lamp (UVP, LLC, Spectroline, Westbury, NY, USA) was used for the visualization of spots on thin-layer chromatograms at 254 and/or 365 nm. Spots were visualized by spraying with 2% vanillin–sulfuric acid in ethanol followed by heating at 110 °C on a hot plate. Moreover, 1H, DEPT135, DEPTQ and 13C NMR spectra were recorded on a Bruker Avance 400 MHz instrument (Bruker, MA, USA). An LTQ Orbitrap XL mass spectrometer (Agilent Technologies, Santa Clara, CA, USA) was used for high-resolution-electrospray ionization-mass spectrum (HR-ESI-MS). The GC-MS analysis was performed with a Agilent 7890A gas chromatograph (Agilent Technologies, Santa Clara, CA, USA) coupled with an Agilent 5975C single quadrupole mass spectrometer (Agilent Technologies, Santa Clara, CA, USA).

4.3. Extraction and Isolation

4.3.1. Extraction and Isolation of Leaves

The air-dried leaves (553.0 g) were macerated with ethanol 95% (1.5 L × 3 times) at room temperature. The ethanol extracts were combined, and the solvent was distilled under reduced pressure at low temperature to afford a 10.0 g yield.
The ethanol extract was processed using vacuum liquid chromatographic techniques with silica gel in a column (600 g, 0.063–0.200 mm; Merck, Darmstadt, Germany). The extract was eluted using a gradient system with n-hexane, DCM, ethyl acetate, and ethanol, with growing polarity as a mobile phase starting with 100% n-hexane and ending with 100% methanol, and 5 fractions were obtained. Fractions were grouped depending on their chemical similarity and monitored using thin-layer chromatography and concentrated using a rotary evaporator. The obtained fractions were L-F1 (1.35 g), L-F2 (0.56 g), L-F3 (0.74 g), L-F4 (1.85 g), and L-F5 (2.37 g).
L-F1, L-F2, and L-F3 were concentrated together to fraction L-F1 according to similar spots on TLC. L-F4 and L-F5 was collected to fraction L-F2. Then, each fraction was separated using chromatographic fractionation in a glass column with silica gel 60 (200 g, 0.063–0.200 mm; Merck, Darmstadt, Germany) and Sephadex LH-20 (Lipophilic, 25–100 µm, Sigma). The mobile phase was n-hexane and ethyl acetate, and 12 fractions were obtained.
Some fractions that were isolated from fractions L-F1 and L-F2 were studied by GC-MS. To analyze fatty acids by GC-MS, it was prepared by refluxing 20 mg of the isolated fractions with 20 mL CH3OH and 2 mL H2SO4 for 4 h.

4.3.2. Extraction and Isolation of Fruits

The air-dried fruits (400.0 g) were macerated with ethanol 95% (1.5 L ×3 times) at room temperature. The ethanol extracts were combined, and the solvent was distilled under reduced pressure at low temperature to afford a 15.0 g yield.
The ethanol extract was processed using vacuum liquid chromatographic techniques with silica gel premium-grade C18 (40–63 µm; 60Å; Sorbtech, Norcross GA, USA) in a column. The extract was eluted using a gradient system with DCM, methanol, and water, with decreasing polarity as a mobile phase starting with 100% water and ending with 100% DCM, and 6 fractions were obtained.
Fractions were grouped depending on their chemical similarity and monitored using thin-layer chromatography and concentrated using a rotary evaporator. The obtained fractions were B-F1 (2.32 g), B-F2 (2.56 g), B-F3 (2.15 g), B-F4 (1.85 g), and B-F5 (1.37 g).
Subsequently, the fractions were separated on Sephadex LH-20 (0.25–0.1 mm, GE Healthcare, Sweden) using methanol as the eluent. As a result, compounds 2, 5, 6, and 7 were obtained.
Some fractions that were isolated from fractions B-F1, B-F2, B-F3, B-F4, and B-F5 were studied by GC-MS. To analyze fatty acids by GC-MS, it was prepared by refluxing 20 mg of the isolated fractions with 20 mL CH3OH and 2 mL H2SO4 for 4 h.

5. Conclusions

Previously, this type of rosehip (Rosa beggeriana Schrenk) had not been studied in terms of chemical composition, hence there are no articles on isolated compounds from this plant. However, there are many research articles about species from the genus Rosa, which are very well known in traditional medicine. The fractionation of Rosa beggeriana Schrenk leaves and fruits resulted in the isolation and structural elucidation of seven compounds, including phytosterol, triterpenoids, polyphenol, and mixture of fatty acids. β-sitosterol (2), betulin (3), (+)-catechin (4), lupeol (5), ethyl linoleate (6) have already been isolated from the genus Rosa but not from Rosa beggeriana Schrenk. And compounds like 3β,23-dihydroxyurs-12-ene (1) and ethyl linolenoate (7) were isolated for the first time for both Rosa and Rosa beggeriana Schrenk.

Supplementary Materials

The following supporting information can be downloaded at: https://www.mdpi.com/article/10.3390/plants12183297/s1, Figure S1: 1H NMR spectrum of 3β,23-Dihydroxyurs-12-ene (1); Figure S2: DEPT135 NMR spectrum of 3β,23-Dihydroxyurs-12-ene (1); Figure S3: 13C NMR spectrum of 3β,23-Dihydroxyurs-12-ene (1); Figure S4: Mass spectrum of 3β,23-Dihydroxyurs-12-ene (1); Figure S5: 1H NMR spectrum of β-sitosterol (2); Figure S6: DEPTQ NMR spectrum of β-sitosterol (2); Figure S7: 1H NMR spectrum of Betulin (2); Figure S8: DEPT135 NMR spectrum of Betulin (2); Figure S9: 13C NMR spectrum of Betulin (2); Figure S10: HSQC NMR spectrum of Betulin (2); Figure S11: HSQC NMR spectrum of Betulin (2); Figure S12: HSQC NMR spectrum of Betulin (2); Figure S13: HSQC NMR spectrum of Betulin (2); Figure S14: GC-MS spectrum of Betulin (2); Figure S15: 1H NMR spectrum of (+)-Catechin (3); Figure S16: DEPT NMR spectrum (+)-Catechin (3); Figure S17: 13C NMR spectrum of (+)-Catechin (3); Figure S18: Mass spectrum of (+)-Catechin (3); Figure S19: 1H NMR spectrum of Lupeol (4); Figure S20: DEPT135 NMR spectrum of Lupeol (4); Figure S21: GC-MS Data of Lupeol (4); Figure S22: 1H NMR spectrum of Ehyl linoleate (5) and Ethyl linolenoate (6); Figure S23: 1H NMR spectrum of Ehyl linoleate (5) and Ethyl linolenoate (6); Figure S24: DEPT135 NMR spectrum of Ehyl linoleate (5) and Ethyl linolenoate (6); Figure S25: 13C NMR spectrum of Ehyl linoleate (5) and Ethyl linolenoate (6); Figure S26: GC-MS Data of Ethyl linoleate (5) and Ethyl linolenoate (6); Figure S27: GC-MS Data of Ethyl linolenoate(6); Figure S28: GC-MS Data of Ethyl linoleate(5).

Author Contributions

Conceptualization, A.A., G.E.Z. and S.A.R.; methodology, G.E.Z. and S.A.R.; software, G.E.Z. and S.A.R.; validation, A.Z., G.E.Z. and S.A.R.; formal analysis A.Z., G.E.Z. and S.A.R.; investigation, A.A.; resources, G.E.Z. and S.A.R.; data curation, A.A. and A.Z.; writing—original draft preparation, A.A.; writing—review and editing, A.Z., G.E.Z. and S.A.R.; visualization, A.A.; supervision, G.E.Z. and S.A.R.; project administration, G.E.Z.; funding acquisition, G.E.Z. and S.A.R. All authors have read and agreed to the published version of the manuscript.

Funding

This research has been/was/is funded by the Science Committee of the Ministry of Science and Higher Education of the Republic of Kazakhstan (Grant No. AP 19677518).

Data Availability Statement

Not applicable.

Acknowledgments

The authors want to express their gratitude to the junior researcher of the Plant Resources Laboratory, Institute of Botany and Phytointroduction (Almaty, Kazakhstan), Madina Ramazanova, for providing the plant material and identifying the plant.

Conflicts of Interest

The authors declare no conflict of interest.

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Plants 12 03297 g001
Figure 1. Chemical structure of 3β,23-dihydroxyurs-12-ene (1).
Figure 1. Chemical structure of 3β,23-dihydroxyurs-12-ene (1).
Plants 12 03297 g001
Plants 12 03297 g002
Figure 2. Chemical structure of betulin (3) and (+)-catechin (4).
Figure 2. Chemical structure of betulin (3) and (+)-catechin (4).
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Plants 12 03297 g003
Figure 3. Chemical structure of β-sitosterol (2), lupeol (5), ethyl linoleate (6), and ethyl linolenoate (7).
Figure 3. Chemical structure of β-sitosterol (2), lupeol (5), ethyl linoleate (6), and ethyl linolenoate (7).
Plants 12 03297 g003
Table 1. GC-MS data for the leaves of Rosa beggeriana Schrenk.
Table 1. GC-MS data for the leaves of Rosa beggeriana Schrenk.
RTCompound NameMatch FactorArea, %
L-2-1—Hexane fraction
40.944Octadeca-9,12,15-trienoic acid95.85.38
L-2-11—n-hexane/ethyl acetate fraction (6/4)
28.259Methyl dodecanoate98.00.95
32.897Methyl tetradecanoate 97.52.61
37.087Methyl hexadecanoate98.614.45
39.021Methyl heptadecanoate95.00.47
40.244Methyl octadeca-9,12-dienoate99.213.16
40.335Methyl octadeca-9,12,15-trienoate99.332.94
40,387Methyl trans-9-octadecenoate91.95.86
40.483Methyl (9Z)-9-octadecenoate96.53.06
40.878Methyl octadecanoate98.66.37
44.340Methyl icosanoate96.21.92
47.540Methyl docosanoate95.12.16
51.111Methyl tetracosanoate95.31.45
55.902Methyl Hexacosanoate90.31.67
CH-21—dichloromethane/ethyl acetate fraction (7/3)
37.078Methyl hexadecanoate90.45.04
CH-39—dichloromethane/ethyl acetate fraction (6/4)
14.4112-Ethylhexan-1-ol96.41.85
32.897Methyl tetradecanoate96.34.83
37.078Methyl hexadecanoate93.12.00
40.225Methyl octadeca-9,12-dienoate96.33.76
40.297Methyl octadeca-9,12,15-trienoate97.69.75
28.259Methyl dodecanoate96.60.58
35.5216,10,14-Trimethylpentadecan-2-one96.30.58
35.6497,11,15-Trimethyl-3-methylidenehexadec-1-ene92.90.33
36.125(2E,7R,11R)-3,7,11,15-Tetramethylhexadec-2-en-1-yl acetate92.30.53
36.5023,7,11,15-Tetramethyl-2-hexadecen-1-ol93.22.10
37.078Methyl hexadecanoate98.412.43
40.302Methyl octadeca-9,12,15-trienoate99.24.85
40.874Methyl octadecanoate96.813.58
41.440Ethyl (9Z,12Z)-octadeca-9,12-dienoate94.614.49
44.340Methyl icosanoate90.1 10.66
L-2-27—ethyl acetate/methanol fraction (8/2)
37.697Hexadecanoic acid94.16.28
40.926Octadeca-9,12,15-trienoic acid93.17.28
Table 2. GC-MS data for the fruits of Rosa beggeriana Schrenk.
Table 2. GC-MS data for the fruits of Rosa beggeriana Schrenk.
RTCompound NameMatch FactorArea, %
B—Ethanol extract
26.198Trimethyl 2-hydroxybutane-1,2,3-tricarboxylate91.713.47
39.397Ethyl hexadecanoate92.45.25
42.430Ethyl (9E,12E)-octadeca-9,12-dienoate92.56.71
42.506Ethyl (9E,12E,15E)-octadeca-9,12,15-trienoate90.06.55
39.397Ethyl hexadecanoate92.74.97
42.430Ethyl (9E,12E)-octadeca-9,12-dienoate92.66.47
42.506Ethyl (9E,12E,15E)-octadeca-9,12,15-trienoate91.66.29
42.430Ethyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate91.23.55
38.068Methyl hexadecanoate96.64.32
38.959Ethyl 9-hexadecenoate92.10.83
41.216Methyl octadeca-9,12-dienoate99.011.16
41.292Methyl octadeca-9,12,15-trienoate98.08.22
41.364Methyl (9Z)-9-octadecenoate93.54.57
41.864Methyl octadecanoate90.81.53
42.435Ethyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate97.915.56
42.516Ethyl (9E,12E,15E)-octadeca-9,12,15-trienoate98.311.37
42.573Ethyl (E)-octadec-9-enoate93.26.22
43.059Ethyl octadecanoate93.81.50
42.425Ethyl (9Z,12Z)-octadeca-9,12-dienoate90.64.82
42.430Ethyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate92.83.09
48.81114-(5-Ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo [8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol93.930.29
56.445Nonacosane92.113.69
B-M1-16—ethyl acetate/methanol fraction (1/1)
37.621Methyl (Z)-pentadec-8-enoate96.10.85
38.073Methyl hexadecanoate98.54.23
38.968Ethyl 9-hexadecenoate97.91.81
39.402Ethyl hexadecanoate98.77.97
41.221Methyl octadeca-9,12-dienoate99.25.82
41.297Methyl octadeca-9,12,15-trienoate98.87.00
41.373Methyl (9Z)-9-octadecenoate93.02.84
41.873Methyl octadecanoate92.20.53
42.449Ethyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate98.427.71
42.530Ethyl (9E,12E,15E)-octadeca-9,12,15-trienoate98.828.61
43.068Ethyl octadecanoate93.20.80
60.378(2R)-2,7,8-Trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol91.41.66
B-M2-18—ethyl acetate/methanol fraction (3/7)
32.478Methyl dodecanoate96.90.61
36.706Tetradecanoic acid99.63.22
38.321(9Z)-Hexadec-9-enoic acid97.93.81
38.854Hexadecanoic acid98.129.50
42.002(9Z,12Z)-Octadeca-9,12-dienoic acid97.727.43
42.135(E)-Octadec-9-enoic acid97.423.95
42.492(E)-Octadec-2-enoic acid96.63.19
26-A—ethyl acetate/methanol fraction (2/8)
40.549Hexadecanoic acid95.88.32
40.549Hexadecanoic acid98.629.85
43.535(9Z,12Z,15Z)-Octadeca-9,12,15-trienoic acid91.13.47
62.859(8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-Ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene90.06.04
Table 3. Spectral data of 1H NMR and 13C NMR of 3β,23-dihydroxyurs-12-ene (1) in CDCl3 and the structures of similar molecules.
Table 3. Spectral data of 1H NMR and 13C NMR of 3β,23-dihydroxyurs-12-ene (1) in CDCl3 and the structures of similar molecules.
No.13C NMR Compound 1Ref. 13C NMR
(3β,24-Dihydroxyurs-12-ene) [35]		Ref. 13C NMR (3β,28-Dihydroxyurs-12-ene) [36]1H NMR
Compound 1		Ref. 1H NMR
(3β,24-Dihydroxyurs-12-ene) [35]		Ref. 1H NMR (3β,28-Dihydroxyurs-12-ene) [36]
138.338.538.78 -
227.327.226.63 -
379.080.978.443.32, m3.45 dd, 11.5/4.4 Hz3.17
442.042.038.60---
555.255.855.15 -
618.418.618.20 -
732.933.132.72 -
840.040.039.86---
947.747.747.56 -
1036.936.636.75---
1123.423.623.22 -
12124.4124.2124.965.26, m5.12 br t, 3.6 Hz5.1
13139.5139.6138.67---
1442.742.742.32---
1528.128.026.24 -
1626.626.623.70 -
1733.733.737.79---
1859.159.054.07---
1939.639.539.62 -
2039.739.639.33 -
2131.231.230.80 -
2241.541.535.15 -
2363.022.427.893.72, m1.250.80
2415.664.516.441.33, s 4.23/3.34 d,11.0 Hz0.93
2515.716.215.511.06, s0.900.92
2616.916.716.441.10, s0.970.92
2723.323.323.701.16, s1.061.09
2828.828.769.200.89, s0.793.52
2917.517.517.230.88, s0.780.81
3021.421.421.200.89, s0.911.00
Table 4. Spectral data of 1H NMR and 13C NMR of (+)-catechin (4) in MeOD and chemical structures of the molecules.
Table 4. Spectral data of 1H NMR and 13C NMR of (+)-catechin (4) in MeOD and chemical structures of the molecules.
No.13C NMRRef. 13C NMR1H NMR
282.983.04.59 (d, J = 7.44 Hz)
368.968.94.00 (q, J = 8.2 Hz)
428.6 28.6 2.88 (dd, J = 16.12, 5.36 Hz)
2.52 (dd, J = 16.08, 8.08 Hz)
5157.6157.7
696.596.45.89 (d, J = 2.3 Hz)
7157.9157.9
895.795.65.96 (d, J = 2.3 Hz)
9157.0157.0
10101.0100.9
1′132.3132.3
2′115.4115.46.86 (d, J = 1.96 Hz)
3′146.3146.4
4′146.3146.3
5′116.3116.26.78 (d, J = 8.16 Hz)
6′120.2120.26.74 (dd, J = 8.16, 2.0 Hz)
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Aituarova, A.; Zhusupova, G.E.; Zhussupova, A.; Ross, S.A. Study of the Chemical Composition of Rosa beggeriana Schrenk’s Fruits and Leaves. Plants 2023, 12, 3297. https://doi.org/10.3390/plants12183297

AMA Style

Aituarova A, Zhusupova GE, Zhussupova A, Ross SA. Study of the Chemical Composition of Rosa beggeriana Schrenk’s Fruits and Leaves. Plants. 2023; 12(18):3297. https://doi.org/10.3390/plants12183297

Chicago/Turabian Style

Aituarova, Aigerim, Galiya E. Zhusupova, Aizhan Zhussupova, and Samir A. Ross. 2023. "Study of the Chemical Composition of Rosa beggeriana Schrenk’s Fruits and Leaves" Plants 12, no. 18: 3297. https://doi.org/10.3390/plants12183297

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