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Article

The Volatile Compounds Composition of Different Parts of Wild Kazakhstan Sedum ewersii Ledeb.

by
Tatyana Kobylina
1,2,
Andriy Novikov
3,
Gulbanu Sadyrova
4,
Elzira Kyrbassova
5,
Saltanat Nazarbekova
1,
Elmira Imanova
5,†,
Meruyert Parmanbekova
5,† and
Bekzat Tynybekov
1,6,*
1
Faculty of Biology and Biotechnology, Al-Farabi Kazakh National University, Al-Farabi Ave. 71, Almaty 050040, Kazakhstan
2
Laboratory of Pharmacological Research, Institute of Physiology and Genetics, Al-Farabi Ave. 93, Almaty 050060, Kazakhstan
3
Department of Biosystematics and Evolution, State Natural History Museum NAS of Ukraine, Teatralna Str. 18, 79008 Lviv, Ukraine
4
Department of Ecology UNESCO for Sustainable Development, Al-Farabi Kazakh National University, Al-Farabi Ave. 71, Almaty 050040, Kazakhstan
5
Department of Biology of the Institute of Naatural Sciences, NPJSC, Kazakh Women’s Teacher Training University, A05C9Y7, St. Gogol, Almaty 114 k1, Kazakhstan
6
Biomedical Research Centre, Al-Farabi Kazakh National University, Al-Farabi Ave. 71, Almaty 050040, Kazakhstan
*
Author to whom correspondence should be addressed.
†
These authors contributed equally to this work.
Separations 2024, 11(7), 208; https://doi.org/10.3390/separations11070208
Submission received: 27 May 2024 / Revised: 26 June 2024 / Accepted: 2 July 2024 / Published: 5 July 2024
(This article belongs to the Special Issue Research Progress for Isolation of Plant Active Compounds)
Browse Figures
Versions Notes

Abstract

:
The chemical composition of Sedum ewersii Ledeb., a plant indigenous to Kazakhstan and traditionally utilized in folk medicine, was comprehensively investigated, with a focus on its various plant parts. Fresh samples collected in May 2023 from the Almaty region underwent hydrodistillation to extract volatile components, followed by analysis using gas chromatography coupled with mass spectrometric detection, which identified a total of 71 compounds across different plant parts, including the root (underground part), root (aerial part), leaf, stem, and flowering aerial part. The predominant biologically active compound identified across all plant parts was Ethyl α-D-glucopyranoside. Monoterpenes, recognized as primary secondary metabolites, were notably abundant in each plant part, with varying compositions: the root (underground part) contained 28.58% aliphatic monoterpenes, 54.41% oxygenated monoterpenoids, 1.42% diterpenoids, and 15.59% other compounds; the root (aerial part) exhibited 1.34% aliphatic monoterpenes, 31.28% oxygenated monoterpenoids, 6.16% diterpenoids, and 61.22% other compounds; the stem and leaves showed 3.06% aliphatic monoterpenes, 21.49% oxygenated monoterpenoids, 17.99% diterpenoids, and 57.46% other compounds; and the flowering aerial part displayed 8.20% aliphatic monoterpenes, 53.18% oxygenated monoterpenoids, 23.75% diterpenoids, and 14.87% other compounds. Diterpenes, particularly Phytol, were prominently present in the leaf, stem, and flowering aerial parts. Additionally, a diverse array of organic acids, ketones, and phenolic compounds were identified across the plant parts, each potentially offering distinct pharmacological benefits. The presence of exclusive compounds in specific plant parts, such as Dihydroxyacetone in the root (aerial part), underscored the pharmacological diversity of S. ewersii. This study provides valuable insights into the chemical diversity and pharmacological potential of S. ewersii, suggesting promising applications in pharmaceutical and medicinal fields. Further research aimed at elucidating the individual and synergistic pharmacological effects of these compounds is crucial to fully harness the therapeutic benefits of this plant.

1. Introduction

Sedum L., or stonecrops, is a genus of flowering plants in the Crassulaceae family [1]. About 400 species of succulent plants make up this varied genus, which is found all over the Northern Hemisphere, with Mexico and South America having the highest diversity [2]. Originating from the Latin word “sedo”, which means “to sit”, the name “sedum” accurately depicts the low-growing habit of many species, which are frequently found nestled against walls or in rocky crevices [3]. Succulent leaves are a distinguishing feature of Sedum species; they retain water and help the plants grow in a variety of harsh conditions, such as rocky and arid ones. They are attractive options for drought-tolerant gardens and green roofs because of their ability to adapt to water-stressed environments. Sedums grow in a variety of forms and sizes, displaying a broad range of growth patterns from creeping groundcovers to upright clumps [4]. Depending on the species and cultivar, Sedum plants have star-shaped flowers that range in color from white and yellow to pink and red and are usually seen in clusters at the tops of the stems. These plants are prized for their ecological significance in addition to their esthetic appeal. With their nectar-rich blooms, sedums draw pollinators like bees and butterflies, promoting biodiversity and the health of ecosystems. Certain kinds of Sedum are used in landscaping and gardening, but they also have historic medicinal purposes. For instance, biting stonecrop, or Sedum acre, has been used in traditional medicine to treat a variety of illnesses, including skin disorders and warts [5].
Sedum plants are popular choices for inexperienced gardeners and those looking for low-maintenance landscaping because they are reasonably easy to grow and require little care. Depending on the species, they can grow in full sun to moderate shade and well-draining soil. Seed planting, division, and stem or leaf cuttings are some methods of propagation [6].
All things considered, Sedum L. is a varied and adaptive genus of plants with ecological and esthetic significance, enhancing the beauty of gardens and landscapes while also promoting biodiversity and environmentally friendly gardening techniques [7].
Sedum L. is a botanical species that exhibits variations in chemical composition based on the location within the plant. The lower portion of the plant has a higher content of cellulose, whereas the upper half of the plant has higher quantities of lignin and extractive, according to Guo, Xinyu et al., and Hu, Ying [8,9]. The different portions of the Sedum L. plant may have distinct physiological characteristics or serve different purposes, as shown by this difference in chemical makeup. Furthermore, the middle lamella, primary wall, and secondary wall that make up Sedum L.’s cell wall structure affect the plant’s chemical makeup [10]. Different plant species, tissues, and stages of the Sedum L. plant’s growth might have quite different structures and chemical compositions for each of these layers. This illustrates the intricacy of Sedum L.’s chemical composition and emphasizes how crucial it is to research its chemical makeup in order to comprehend its biological roles and possible advantages. Moreover, it is significant to remember that Sedum L.’s chemical makeup influences both its biological activities and its therapeutic qualities [11].
Sedum L. produces secondary metabolites, including sulfur-containing chemicals, alkaloids, phenolic compounds, and terpenoids [12]. Given that Sedum L. contains several times more alkaloids than other species within its genus, it is not considered a promising medicinal plant in domestic medicine due to its caustic nature [13]. However, Sedum L. has been utilized in folk medicine as a diuretic, anti-inflammatory, stimulant, and restorative agent [14]. Additionally, it is used in homeopathy for treating hemorrhoids. Infusions made from Sedum L. are recommended for addressing constipation, hypotension, and malaria, and for external application on infected purulent wounds, eczema, trophic ulcers, and hyperkeratosis [15]. Diluted fresh plant juice is taken internally to treat anemia, vitamin deficiencies, vascular atherosclerosis, and intestinal paresis. Moreover, fresh juice is applied to remove papillomas and warts, and to lighten pigmented areas of the skin. The extract of Sedum L. has served as the foundation for the production of a biostimulating drug known as “Biosed.” Belarusian residents have also recognized the healing properties of Sedum L.: Sedum tea is consumed to address cardiovascular diseases, hepatitis, and skin ailments. An ointment composed of dried plant materials, camphor, and lard is suitable for treating intermittent fever and tumors [16]. Hungarians utilize Sedum L. externally to manage thyroid disorders. Oriental medicine practitioners believe that Sedum L., with medicinal properties resembling those of cinchona, may possess antimalarial effects [17]. In Bulgaria, traditional healers use the plant as a pain reliever for hemorrhoids, epilepsy, atherosclerosis, and scurvy, and apply it externally as a poultice for neoplasms [18]. Regarding contraindications and side effects, the use of Sedum L. is not recommended for individuals with hypertension or increased nervous excitability, during pregnancy, or while lactating. Treatment with Sedum L. is also contraindicated in children in Kazakhstan. Overdosing on this plant may result in vomiting, stomach cramps, diarrhea, disruptions in cardiovascular functioning, and difficulty breathing. When using Sedum L. externally, caution is advised as fresh plant sap can cause local irritation, burns, and blisters on healthy skin [19].
Numerous chronic diseases are linked to oxidative stress, which is caused by an imbalance between the body’s capacity to neutralize reactive oxygen species (ROS) and their generation, including cardiovascular disorders, neurodegenerative conditions, and cancer. Consequently, the search for natural sources of antioxidants has become a subject of intense research interest. Simultaneously, the membrane-stabilizing properties of bioactive compounds have gained prominence for their ability to protect cell membranes from damage, thereby contributing to cellular health [20,21].
In this study, the chemical composition of the aerial parts of the plant S. ewersii (Figure 1), which grows wild in Kazakhstan and is used in folk medicine, was studied for the first time.

2. Materials and Methods

2.1. Plant Material

The aerial parts of S. ewersii at full flowering stage were collected in May 2023 in the Almaty region. A voucher specimen (Number E-2333) was identified by Prof. A. Ametov, Biodiversity and Bioresources Department, Al-Farabi Kazakh National University (Kazakhstan). Plant materials were air-dried at room temperature for later analysis.

2.2. Preparation of Plant Extracts

Fresh samples (50 g) were cut and ground in a Waring blender and then subjected to hydrodistillation for 3 h using distilled water (≈100 g), according to the standard procedure described in the European Pharmacopoeia (2020) [22]. Hydrodistillation is a widely accepted method for extracting volatile compounds; however, the identification of these compounds is tentative pending further confirmation using additional analytical techniques or standards. Quantification of volatile compounds was performed by integrating peak areas obtained from gas chromatography analysis. Each analysis was conducted in triplicate for robustness and to ensure the reliability of the results. The EOs (essential oils) were dried over anhydrous sodium sulfate and stored in sealed vials under N 2, at −20 °C, ready for the GC and GC-MS analyses; the samples yielded 0.04% of EO (w/w).

2.3. GC-MS Analyses

Samples were analyzed by gas chromatography with mass spectrometric detection (7890A/5975C). Sample volume was 0.5 µL and sample injection temperature was 250 °C, without flow splitting. Separation was carried out using a DB-WAXetr chromatographic capillary column with a length of 30 m, an internal diameter of 0.25 mm, and a film thickness of 0.25 μm at a constant carrier gas (helium) rate of 1 mL/min. The chromatography temperature was programmed from 40 °C with a heating rate of 5 °C/min to 260 °C (holding time 5 min). Analysis time was 49 min. Detection was carried out in SCAN mode m/z 34–850. HP-Chemstation software (Agilent Technologies, Santa Clara, CA, USA) was used to control the gas chromatography system and record and process the results, and data were obtained. Data processing included determination of retention times and peak areas, as well as processing of spectral information obtained using a mass spectrometric detector. To interpret the obtained mass spectra, the Wiley 7th edition and NIST’02 libraries were used (the total number of spectra in the libraries is more than 550 thousand).

3. Results and Discussion

Table 1 displays the findings from the investigation of the chemical composition of S. ewersii. Hydrodistillation of various parts of S. ewersii, including its flowering aerial parts, root (underground part), root (aerial part), and stem + leaves, led to the identification of 71 compounds, as listed in Table 1. Specifically, 40 compounds were derived from the root (underground part), 41 from the root (aerial part), 41 from the leaf and stem, and 31 from the flowering aerial part. Ethyl α-D-glucopyranoside emerged as the most prevalent biologically active substance across all four plant parts, constituting 28.79% in the root (underground part), 20.36% in the root (aerial part), 12.95% in the leaf and stem, and 22.04% in the flowering aerial part. This compound, also known as α-EG, is commonly found in sake (Japanese rice wine) and is recognized for its moisturizing and skin conditioning effects [23].
A class of isoprenoids known as monoterpenes (or monoterpenoids) is created when different monoterpene synthases convert geranyl diphosphate (GPP, C10) into monoterpenes. Monoterpenes are useful substances that are used as ingredients in medications, culinary flavorings, cleaning supplies, and cosmetics. Monoterpenes and their derivatives play a crucial role in the development of novel physiologically active compounds [24]. In S. ewersii, monoterpene hydrocarbons accounted for 16.44% of the root (underground part) composition, with notable constituents such as (-)-cis-Myrtanol (3.67%), geraniol (1.9%), p-Cymen-7-ol (0.76%), benzyl alcohol (0.97%), benzofuran, 2,3-dihydro- (1.42%), 2,3-Dihydro-4-hydroxy-2(3H)-furanone (0.67%), and octacosane (5.94%). Similarly, the root (aerial part) contained 16.83% monoterpene hydrocarbons, including (-)-cis-Myrtenol (0.71%), geraniol (3.32%), p-Cymen-7-ol (0.73%), benzofuran, 2,3-dihydro- (4.60%), 2,3-Dihydro-4-hydroxy-2(3H)-furanone (1.06%), and octacosane (4.45%). Each of these compounds has unique pharmacological properties and potential applications. (-)-cis-Myrtanol is a naturally occurring alcohol with a complex fragrance [25]. It may have antimicrobial, anti-inflammatory, or antioxidant properties. It is commonly used in perfumery and aromatherapy [26]. Octacosane is a straight-chain hydrocarbon, a type of alkane, found in various plant waxes [27]. It has been studied for its potential biological activities, including antioxidant and anti-inflammatory properties [28]. Geraniol is a monoterpene alcohol found in various essential oils, such as rose oil and citronella oil. It has been studied for its potential antimicrobial, antioxidant, and anti-inflammatory properties [29]. In the leaf and stem, the principal class constituted 15.11% monoterpene hydrocarbons, comprising geraniol (1.54%), benzofuran, 2,3-dihydro- (12.43%), and 2,3-Dihydro-4-hydroxy-2(3H)-furanone (1.14%). Notably, (-)-cis-Myrtenol, benzyl alcohol, p-Cymen-7-ol, and octacosane were absent in this part. 2,3-Dihydro-4-hydroxy-2(3H)-furanone is also known as gamma-hydroxybutyrolactone (GHB). It is a central nervous system depressant and has been used medically as a sedative–hypnotic and anesthetic. However, it is also commonly abused as a recreational drug due to its euphoric effects. In the flowering aerial part, 15.53% of monoterpene hydrocarbons were identified, with (-)-cyclopropyl carbinol (0.76%), and benzofuran, 2,3-dihydro- (14.77%) being the principal components. However, benzyl alcohol, (-)-cis-Myrtenol, geraniol, p-Cymen-7-ol, 2,3-Dihydro-4-hydroxy-2(3H)-furanone, and octacosane were not detected. Among the identified compounds, benzofuran derivatives are noteworthy for their diverse pharmacological activities, including potential anti-inflammatory, antioxidant, and antimicrobial properties [30]. Additionally, several compounds showed potential antioxidant and antimicrobial properties. These compounds have also found application in the food industry as flavoring agents [31].
In Figure 2, high peaks of compounds such as (-)-myrtenol (19.82%) at a retention time of 116.4 min and ethyl α-D-glucopyranoside (28.79) at 42.9 min can be observed. Oxygenated monoterpenes in the root (underground part) were present in a significant amount (37.18%, Figure 2), with compounds such as Butanoic acid, 4-hydroxy-(0.77%), 2-Furanmethanol (1.33%), 2(5H)-Furanone (0.83%), (-)-Myrtenol (19.82%), 2,6-Octadien-1-ol, 3,7-dimethyl-, (Z)- (0.44%), Propanoic acid, 2-methyl-, 3-hydroxy-2,4,4-trimethylpentyl ester (0.94%), Phenylethyl Alcohol (0.43%), 1-Cyclohexene-1-methanol, 4-(1-methylethenyl)-(0.57%), 1,4-Cyclohexadiene-1-methanol, 4-(1-methylethyl)-(1.11%), 1,3-Cyclohexadiene-1-methanol, 4-(1-methylethyl)-(1.64%), 2-Hydroxy-gamma-butyrolactone (3.60%), 2-Methoxy-4-vinylphenol (1.41%), 2-Propen-1-ol, 3-phenyl-(1.56%), Ethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate (0.71%), 4-((1E)-3-Hydroxy-1-propenyl)-2-methoxyphenol (0.38%), and p-Hydroxycinnamic acid ethyl ester (0.74%). Butyrolactone, n-Amyl ether, 5-Hydroxymethylfurfural, o-Methoxy-α,α-dimethyl benzyl alcohol, 2-Furanmethanol, 5-ethenyltetrahydro-α,α,5-trimethyl-, cis-, 2-Furancarboxylic acid, 1-Octanol, and Ethyl 2,3-epoxybutyrate were not found. Among them, 2-Furanmethanol, 2(5H)-Furanone, (-)-Myrtenol, 2,6-Octadien-1-ol, 3,7-dimethyl-, (Z)-, Phenylethyl alcohol, 1-Cyclohexene-1-methanol, 4-(1-methylethenyl)-, 1,4-Cyclohexadiene-1-methanol, 4-(1-methylethyl)-, 1,3-Cyclohexadiene-1-methanol, 4-(1-methylethyl)-, 2-Methoxy-4-vinylphenol, 4-((1E)-3-Hydroxy-1-propenyl)-2-methoxyphenol, 2-Furanmethanol, 5-ethenyltetrahydro-α,α,5-trimethyl-, and cis- 5-Hydroxymethylfurfural, cis- have been studied for their potential antioxidant and antimicrobial properties. Additionally, these compounds are used in the food industry as flavoring agents [32].
Figure 3 shows the chromatogram of the identified compounds; high peaks with retention time (minutes) can be noted: 2-Hydroxy-gamma-butyrolactone (6.50%) at 23.4 min, 2-Propen-1-ol, 3-phenyl-(6.71%) at 25.6 min, and Ethyl α-d-glucopyranoside (20.36%) at 42.9 min. Oxygenated monoterpenes in the root (aerial part, Figure 3) were present in a significant amount (25.05%). Notable compounds included 2-Furanmethanol (1.58%), 2(5H)-Furanone (1.64%), 2,6-Octadien-1-ol, 3,7-dimethyl-, (Z)- (0.39%), Phenylethyl Alcohol (0.99%), 1-Cyclohexene-1-methanol, 4-(1-methylethenyl)- (0.56%), 1,3-Cyclohexadiene-1-methanol, 4-(1-methylethyl)-(0.78%), 2-Hydroxy-gamma-butyrolactone (6.50%), 2-Propen-1-ol, 3-phenyl-(6.71%), p-Hydroxycinnamic acid, ethyl ester (1.20%), Butyrolactone (0.89%), n-Amyl ether (2.53%), 5-Hydroxymethylfurfural (0.82%), o-Methoxy-α,α-dimethyl benzyl alcohol (0.46%), 2-Furanmethanol, and 5-ethenyltetrahydro-α,α,5-trimethyl-, cis- (1.11%). Butanoic acid, 4-hydroxy-, (-)-Myrtenol, Propanoic acid, 2-methyl-, 3-hydroxy-2,4,4-trimethylpentyl ester, 1,4-Cyclohexadiene-1-methanol, 4-(1-methylethyl)-, 2-Methoxy-4-vinylphenol, Ethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate, 1-Octanol, and Ethyl 2,3-epoxybutyrate were not found. Among them, the compounds 2-Hydroxy-gamma-butyrolactone, 2-Propen-1-ol, 3-phenyl-, Ethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate, p-Hydroxycinnamic acid, ethyl ester, Butyrolactone, n-Amyl ether, o-Methoxy-α,α-dimethyl benzyl alcohol, 1-Octanol, and Ethyl 2,3-epoxybutyrate have potential applications as solvents or in organic synthesis, as well as in fragrance formulation [33].
Oxygenated monoterpenes in the leaf and stem were present in a substantial amount (15.99%, Figure 4). Noteworthy compounds included Butanoic acid, 4-hydroxy- (0.82%), 2-Furanmethanol (2.15%), 2(5H)-Furanone (0.66%), (-)-Myrtenol (1.64%), Phenylethyl Alcohol (0.42%), 1-Cyclohexene-1-methanol, 4-(1-methylethenyl)- (0%), 1,4-Cyclohexadiene-1-methanol, 4-(1-methylethyl)- (2.03%), 1,3-Cyclohexadiene-1-methanol, 4-(1-methylethyl)- (0%), 2-Hydroxy-gamma-butyrolactone (4.52%), 2-Methoxy-4-vinylphenol (1.13%), 2-Propen-1-ol, 3-phenyl- (0.51%), 4-((1E)-3-Hydroxy-1-propenyl)-2-methoxyphenol (0.38%), Butyrolactone (1.39%), 5-Hydroxymethylfurfural (0.66%), 2,6-Octadien-1-ol, 3,7-dimethyl-, (Z)-, and 2-Furancarboxylic acid (0.38%). p-Hydroxycinnamic acid, ethyl ester, Ethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate, Propanoic acid, 2-methyl-, 3-hydroxy-2,4,4-trimethylpentyl ester, n-Amyl ether, o-Methoxy-α,α-dimethyl benzyl alcohol, 2-Furanmethanol, 5-ethenyltetrahydro-α,α,5-trimethyl-, cis-, 1-Octanol, Ethyl 2,3-epoxybutyrate were not found. Butanoic acid, 4-hydroxy- is also known as gamma-hydroxybutyric acid (GHB), it is a central nervous system depressant and has been used medically as a sedative–hypnotic and anesthetic. However, it is also commonly abused as a recreational drug due to its euphoric effects [34].
Figure 4 shows us a chromatogram of the identified compounds, which shows high peaks with the retention times (minutes) of such compounds as 1,3-Dioxol-2-one,4,5-dimethyl-(5.13%)—22.6 min; 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl-(4.95%)—25.0 min; Benzofuran, 2,3-dihydro-(12.43%)—27.4 min; Phytol (5.56%)—31.6 min; 1-Deoxy-d-arabitol 11.83%)—33.6 min; and Ethyl α-d-glucopyranoside (12.95%)—42.9 min. Oxygenated monoterpenes in the flowering aerial part were present in a significant amount (13.85%, Figure 5). Notable compounds included 2-Furanmethanol (1.54%), 2,6-Octadien-1-ol, 3,7-dimethyl-, (Z)- (1.31%), Phenylethyl Alcohol (0.41%), 1-Cyclohexene-1-methanol, 4-(1-methylethenyl)- (0.48%), 2-Hydroxy-gamma-butyrolactone (2.21%), 2-Methoxy-4-vinylphenol (0.58%), 2-Propen-1-ol, 3-phenyl- (2.90%), p-Hydroxycinnamic acid, ethyl ester (0%), Butyrolactone (0.39%), 5-Hydroxymethylfurfural (0.63%), 1-Octanol (0.69%), and Ethyl 2,3-epoxybutyrate (1.71%),. Butanoic acid, 4-hydroxy-, 2(5H)-Furanone,(-)-Myrtenol, Propanoic acid, 2-methyl-, 3-hydroxy-2,4,4-trimethylpentyl ester, 1,4-Cyclohexadiene-1-methanol, 4-(1-methylethyl)-, 1,3-Cyclohexadiene-1-methanol, 4-(1-methylethyl)-, Ethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate, 4-((1E)-3-Hydroxy-1-propenyl)-2-methoxyphenol, n-Amyl ether, o-Methoxy-α,α-dimethyl benzyl alcohol, 2-Furanmethanol, 5-ethenyltetrahydro-α,α,5-trimethyl-, and cis-, 2-Furancarboxylic acid were not found. Oxygenated monoterpenes and monoterpene hydrocarbon compounds play a crucial role in biological and medical applications. It is also known that monoterpenes and their derivatives exhibit anti-inflammatory, antimicrobial, anticonvulsant, analgesic, antiviral, antitumor, antituberculosis, and antioxidant biological activities [35].
The chromatogram of S. ewersii’s flowering aerial part (Figure 5) shows high peaks with the retention times (minutes) of compounds such as Bicyclo[3,1,1]hept-2-ene-2-methanol, 6,6-dimethyl- (5.95%)—16.3 min; 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- (5,26%)—25.0 min; Benzofuran, 2,3-dihydro- (14.77%)—27.5 min; 9,12,15-Octadecatrienoic acid, ethyl ester, (Z,Z,Z)- (9.41%)—31.1 min; Phytol (8.98%)—31.6 min; and Ethyl α-d-glucopyranoside (22.04%)—42.9 min. Depending on their skeletal core, diterpenes can be categorized as linear, bicyclic, tricyclic or tetracyclic, pentacyclic, and macrocyclic [36]. Of the diterpenes found in this plant, Phytol, which is present in the root (aerial part) at 1.56%, at 5.56% in the leaf and stem, and 8.98% in the flowering aerial part, in the root (underground part), was not found. Natural diterpenes have a variety of biological effects, including anti-inflammatory, antibacterial, and antispasmodic effects [37]. Numerous diterpenes have demonstrated significant effects on the cardiovascular system. They include marrubenol, which inhibits smooth muscle contraction by blocking L-type calcium channels; eleganolone and 14-deoxyandrographolide, which exhibit vasorelaxant qualities; and grayanotoxin I, which elicits positive inotropic responses [38]. Two hydrocarbon substituents joined to a carbonyl atom form a ketone. The body produces ketones when cells do not receive enough glucose, which is the body’s main energy source. Blood or urine can contain ketones, and elevated levels of these compounds may signify ketoacidosis [39]. Ketones were found in varying amounts across different parts of S. ewersii. In the root (underground part), ketones were present at a level of 6.72%, with notable compounds including 4-Cyclopentene-1,3-dione (0.78%), 2-Cyclopenten-1-one, 2-hydroxy-(1.16%), 2,5-Dimethyl-4-hydroxy-3(2H)-furanone (0.43%), 1,3-Dioxol-2-one,4,5-dimethyl-(2.44%), and 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl-(1.91%). 4-(p-Acetoxy phenyl)-2-butanone was not found. In the root (aerial part), ketones were more abundant at 13.54%, featuring similar compounds but with differing concentrations: 4-Cyclopentene-1,3-dione (1.34%), 2-Cyclopenten-1-one, 2-hydroxy- (2.23%), 2,5-Dimethyl-4-hydroxy-3(2H)-furanone (0.65%), 1,3-Dioxol-2-one,4,5-dimethyl- (5.66%), and 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- (3.66%). 4-(p-Acetoxy phenyl)-2-butanone was not detected. Similarly, in the leaf and stem, ketones were present at 13.57%, with notable compounds such as 4-Cyclopentene-1,3-dione (0.94%), 2-Cyclopenten-1-one, 2-hydroxy-(1.48%), 2,5-Dimethyl-4-hydroxy-3(2H)-furanone (1.07%), 1,3-Dioxol-2-one,4,5-dimethyl-(5.13%), and 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- (4.95%). 4-(p-Acetoxy phenyl)-2-butanone was not found. Ketones in the flowering aerial part were also present in similar amount (13.52%), showcasing various compounds including 4-Cyclopentene-1,3-dione (0.70%), 2-Cyclopenten-1-one, 2-hydroxy- (0.84%), 2,5-Dimethyl-4-hydroxy-3(2H)-furanone (2.89%), 1,3-Dioxol-2-one,4,5-dimethyl- (2.75%), 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl- (5.26%), and 4-(p-Acetoxy phenyl)-2-butanone (1.08%). These ketones may possess diverse pharmacological properties, potentially including antioxidant, antimicrobial, or anti-inflammatory effects [40].
Organic acids are organic compounds that possess acidic qualities; they are categorized according to the quantity of carboxylic functionalities. Organic acids are typically weak acids. But compared to carboxylic acids, organic acids including phenol, enol, alcohol, and thiol groups are weaker. The amount of carbon–carbon double bonds and hydroxy or carboxyl functional groups that are present in the structures of organic acids varies [41]. In the root (aerial part), the following compounds were identified: Butanoic acid, 4-hydroxy- (0.77%), Propanoic acid, 2-methyl-, 3-hydroxy-2,4,4-trimethylpentyl ester (0.94%), and Ethyl 9,12,15-octadecatrienoate (0.92%). Notably, Butanoic acid, 4-hydroxy- is also known as gamma-hydroxybutyric acid (GHB), it is a central nervous system depressant and has been used as a treatment for narcolepsy and alcohol withdrawal. However, it is prone to abuse due to its euphoric and sedative effects [34]. Among the organic acids in the root (aerial part), only Ethyl 9,12,15-octadecatrienoate (2.07%) was detected, which is an essential fatty acid. This compound, also known as linolenic acid, plays crucial roles in physiological processes and offers potential health benefits, including anti-inflammatory and cardioprotective properties [42]. In the leaf and stem, the following compounds were identified: Butanoic acid, 4-hydroxy-(0.82%), Ethyl 9,12,15-octadecatrienoate (3.10%), Propanoic acid (0.47%), Butanoic acid 2-methyl- (0.84%), Butanoic acid, 3-methylbutyl ester (2.60%), and Butanoic acid, 2-oxo-(1.71%). Butanoic acid, 2-methyl- and Butanoic acid, 3-methylbutyl ester are used in fragrance compositions and as a flavoring agent in the food industry [43]. Additionally, Butanoic acid, 2-oxo- is known as butyric acid; it is involved in various physiological processes and has been studied for its potential role in gastrointestinal health. It may have anti-inflammatory and anticancer properties [44]. In the flowering aerial part, two organic acids were identified: Butanoic acid, 2-methyl- (1.63%) and 9,12,15-Octadecatrienoic acid, ethyl ester, (Z,Z,Z)- at 9.41%; this compound is an ethyl ester derivative of linolenic acid, similar to ethyl 9,12,15-octadecatrienoate. It may have similar health benefits attributed to linolenic acid, including anti-inflammatory properties. Simultaneously, other chemical compounds were detected [45]. Among them, Urea, 1-methylcyclopropyl- (2.86%), (2,2,6-Trimethyl-bicyclo[4,1,0]hept-1-yl)-methanol (0.88%), and 5-Oxotetrahydrofuran-2-carboxylic acid, ethyl ester (0.48%) were exclusively found in the underground part of the root. These compounds lack well-documented pharmacological properties and are primarily utilized as chemical intermediates in organic synthesis rather than as pharmaceutical agents [46].
The findings of a study on molecular formulas of actual phytochemical compounds of the plant S. ewersii are shown in Figure 1, Figure 2, Figure 3 and Figure 4. In the root (aerial part), the most prevalent substances were Bicyclo[3,1,1]hept-2-ene-2-methanol, 6,6-dimethyl- (5.6%), Glycerin (1.96%), 1,2-Ethanediol, 1-(2-furanyl)-(1.9%), and Dihydroxyacetone (1.62%). Bicyclo[3,1,1]hept-2-ene-2-methanol, 6,6-dimethyl-, and 1,2-Ethanediol, 1-(2-furanyl)- (also known as furan-2-ylmethanediol) lack common usage in pharmacology, and their pharmacological properties remain poorly documented [47]. Glycerin exhibits several pharmacological properties, including its use as a topical emollient and moisturizer due to its capacity to attract and retain moisture [48]. Dihydroxyacetone (DHA) is chiefly recognized for its role as the active ingredient in sunless tanning products, where it reacts with amino acids in the skin to produce a temporary tan appearance [49].
Various other substances exclusively found in stems and leaves, include 1-Deoxy-d-arabitol (11.83%), 1,3-Cyclopentanediol, cis- (2.71%), β-D-Ribopyranoside, methyl (2.47%), β-d-Lyxofuranoside, methyl (1.90%), (S)-(+)-2′,3′-Dideoxyribonolactone (0.63%), 2-Cyclopenten-1-one, 2-hydroxy-3-methyl- (0.32%), 1,2,3-Propanetriol, 1-acetate (0.32%), and Phenol (0.14%). Researchers hypothesize that these substances may possess various biological activities, potentially applicable in medicinal chemistry. Each compound may exhibit a spectrum of pharmacological effects depending on its specific chemical properties, concentrations, and interactions with biological systems [50].
In the flowering aerial part, two organic acids were identified: The first is 9,12-Octadecadienoic acid, ethyl ester (2.94%); this compound is an ethyl ester derivative of linoleic acid, which is an essential fatty acid. Linoleic acid is involved in various physiological processes and has potential health benefits, including cardiovascular health and anti-inflammatory properties [51]. The second is Phenol, 2,4-bis(1,1-dimethylethyl)- (1.35%); this compound is commonly known as 2,4-di-tert-butylphenol. It has antioxidant properties and is often used as a stabilizer in various products such as fuels, lubricants, and plastics Additionally, it may exhibit antimicrobial properties. 7-Oxabicyclo[4,1,0]heptane, 1-methyl-4-(2-methyloxiranyl)- (1.08%) is a bicyclic compound containing an oxirane (epoxide) functional group, indicating potential reactivity that could lead to various biological activities or applications in medicinal chemistry. 3,4-Dihydroxy-5-methyl-dihydrofuran-2-one (0.98%), also known as 5-methyl-3,4-dihydroxy-2(5H)-furanone or 5-methyl-2,3-dihydro-4H-pyran-4-one, is a derivative of furanone with potential antioxidant or antimicrobial properties [52]. Furanones have been investigated for their potential health benefits and applications in food preservation [53].
Ethyl β-d-riboside (ranging from 0.98% to 2.12%) and Phenol, 2,6-dimethoxy- (ranging from 0.45% to 1.19%) were identified in all parts of S. ewersii. Ethyl β-d-riboside, a derivative of ribose, a type of sugar molecule, may exert various pharmacological effects depending on its metabolism and interactions within the body [54]. Ribose derivatives are sometimes investigated for their potential applications in nucleoside synthesis or as pharmaceutical intermediates [55]. Phenol, 2,6-dimethoxy-, a derivative of phenol, a widely studied chemical compound with diverse pharmacological properties, may have altered biological activity due to the addition of methoxy groups at positions 2 and 6 of the phenol ring [56]. Phenolic compounds, including methoxyphenols, are recognized for their antioxidant, antimicrobial, and potentially anti-inflammatory properties [52]. However, the specific pharmacological effects of 2,6-dimethoxyphenol would depend on factors such as concentration, route of administration, and target biological systems.
Monoterpenes were abundant across the plant parts, with distinct compositions: the root (underground part) contained 28.58% aliphatic monoterpenes, 54.41% oxygenated monoterpenoids, 1.42% diterpenoids, and 15.59% other compounds; the root (aerial part) exhibited 1.34% aliphatic monoterpenes, 31.28% oxygenated monoterpenoids, 6.16% diterpenoids, and 61.22% other compounds; the stem and leaves showed 3.06% aliphatic monoterpenes, 21.49% oxygenated monoterpenoids, 17.99% diterpenoids, and 57.46% other compounds; and the flowering aerial part displayed 8.20% aliphatic monoterpenes, 53.18% oxygenated monoterpenoids, 23.75% diterpenoids, and 14.87% other compounds. Diterpenes, notably Phytol, were prominently present in the leaf, stem, and flowering aerial parts. Additionally, a diverse array of organic acids, ketones, and phenolic compounds were identified, each potentially offering distinct pharmacological benefits. In the study of biologically active substances in medicinal plants, it is crucial to initially investigate their growth environment, populations, raw materials, and the environmental and anthropogenic factors that impact them [57,58,59]. Moreover, factors such as the cultivation methods of medicinal plants, the required soil conditions, biohumus, and phytohormones should also be considered [60,61,62]. This study underscores the pharmacological diversity of S. ewersii and suggests its potential applications in the pharmaceutical and medicinal fields [63], highlighting the need for further research to elucidate the specific and combined pharmacological effects of these compounds.

4. Conclusions

The volatile compound composition and medicinal potential of S. ewersii, growing wild in Kazakhstan, were explored through hydrodistillation of various plant parts, including its flowering aerial parts, root (underground part), root (aerial part), and stem + leaves. Analysis revealed the presence of 71 compounds, as detailed in Table 1. Notably, the root (underground part) yielded 40 compounds, the root (aerial part) yielded 41 compounds, the leaf and stem yielded 41 compounds, and the flowering aerial part yielded 31 compounds. Among these, ethyl α-D-glucopyranoside emerged as the predominant biologically active substance across all four plant parts, constituting 28.79%, 20.36%, 12.95%, and 22.04% in the root (underground part), root (aerial part), leaf and stem, and flowering aerial part, respectively. This compound, also referred to as α-EG, is commonly found in sake (Japanese rice wine) and is recognized for its moisturizing and skin conditioning effects. Ethyl α-D-glucopyranoside emerged as the predominant biologically active compound, found consistently across all plant parts. Monoterpenes, a class of secondary metabolites known for their diverse pharmacological properties, were abundant, with compounds such as (-)-cis-Myrtanol, geraniol, and (-)-cyclopropyl carbinol identified. Diterpenes, categorized based on their skeletal core, were also detected, with Phytol notably present in the leaf and stem as well as the flowering aerial part. Organic acids, ketones, and other chemical compounds were found in varying amounts across different plant parts, each potentially offering unique pharmacological properties.
The primary class of secondary metabolites identified in S. ewersii is monoterpenes, which encompass hydrocarbons frequently present in essential oils. These findings contribute to our understanding of the chemical composition and potential therapeutic properties of S. ewersii, laying a foundation for further research into its pharmacological applications and medicinal uses.

Author Contributions

Conceptualization, B.T. and A.N.; methodology, T.K.; software, G.S.; validation, E.K.; formal analysis, E.I.; investigation, M.P.; resources, B.T.; data curation, E.I. and M.P.; writing—original draft preparation, T.K.; writing—review and editing, B.T.; visualization, S.N.; supervision, B.T. and A.N. All authors have read and agreed to the published version of the manuscript.

Funding

This research was supported by the project “AP23484931” financed by the Scientific Committee of the Ministry of Science and Higher Education of the Republic of Kazakhstan.

Data Availability Statement

The data presented in this study are available on request from the corresponding author.

Acknowledgments

The community of authors would like to thank this institution and the Biomedical Research Centre, Al-Farabi Kazakh National University.

Conflicts of Interest

The authors declare that they have no conflicts of interest.

References

  1. Karahan, F.; Öz, I.; Demircan, N.; Stephenson, R.A.Y. Succulent Plant Diversity in Turkey I. Stonecrops (Crassulaceae). Haseltonia 2006, 12, 41–54. [Google Scholar] [CrossRef]
  2. Walker, C. An introduction to Mexican Sedums. N. Z. Cactus Succul. J. 2022, 75, 28–34. [Google Scholar]
  3. Mo, E.K.; Kim, S.M.; Yang, S.A.; Oh, C.J.; Sung, C.K. Assessment of antioxidant capacity of sedum (Sedum sarmentosum) as a valuable natural antioxidant source. Food Sci. Biotechnol. 2011, 20, 1061–1067. [Google Scholar] [CrossRef]
  4. Horvath, B. The Plant Lover’s Guide to Sedums; Timber Press: Portland, OR, USA, 2014; Volume 120. [Google Scholar]
  5. Berganayeva, G.; Kudaibergenova, B.; Litvinenko, Y.; Nazarova, I.; Sydykbayeva, S.; Vassilina, G.; Izdik, N.; Dyusebaeva, M. Medicinal Plants of the Flora of Kazakhstan Used in the Treatment of Skin Diseases. Molecules 2023, 28, 4192. [Google Scholar] [CrossRef] [PubMed]
  6. Cabahug, R.A.M.; Nam, S.Y.; Lim, K.B.; Jeon, J.K.; Hwang, Y.J. Propagation techniques for ornamental succulents. Flower Res. J. 2018, 26, 90–101. [Google Scholar] [CrossRef]
  7. Nagase, A.; Koyama, S. Attractiveness and preference of extensive green roofs depend on vegetation types and past experience with plants in Japan. Urban For. Urban Green. 2020, 51, 126658. [Google Scholar] [CrossRef]
  8. Guo, X.; Zhang, S.; Luo, J.; Pan, M.; Du, Y.; Liang, Y.; Li, T. Integrated glycolysis and pyrolysis process for multiple utilization and cadmium collection of hyperaccumulator Sedum alfredii. J. Hazard. Mater. 2022, 422, 126859. [Google Scholar] [CrossRef] [PubMed]
  9. Hu, Y.; Zhou, X.; Shi, A.; Yu, Y.; Rensing, C.; Zhang, T.; Yang, W. Exogenous silicon promotes cadmium (Cd) accumulation in Sedum alfredii Hance by enhancing Cd uptake and alleviating Cd toxicity. Front. Plant Sci. 2023, 14, 1134370. [Google Scholar] [CrossRef]
  10. Parrotta, L.; Guerriero, G.; Sergeant, K.; Cai, G.; Hausman, J.F. Target or barrier? The cell wall of early-and later-diverging plants vs cadmium toxicity: Differences in the response mechanisms. Front. Plant Sci. 2015, 6, 133. [Google Scholar] [CrossRef]
  11. Minzanova, S.T.; Mironov, V.F.; Arkhipova, D.M.; Khabibullina, A.V.; Mironova, L.G.; Zakirova, Y.M.; Milyukov, V.A. Biological activity and pharmacological application of pectic polysaccharides: A review. Polymers 2018, 10, 1407. [Google Scholar] [CrossRef]
  12. Odeh, A.A.; Al-Jaber, H.I.; Barhoumi, L.M.; Shakya, A.K.; Al-Qudah, M.A.; Al-Sanabra, O.M. Phytochemical and bioactivity evaluation of secondary metabolites and essential oils of Sedum rubens growing wild in Jordan. Arab. J. Chem. 2023, 16, 104712. [Google Scholar] [CrossRef]
  13. Akhmetova, A.; Mukhitdinov, N.; Ydyrys, A. Anatomical indicators of the leaf structure of Ferula iliensis, growing in the eastern part of Zailiyskiy Alatau (Big Boguty Mountains). Pak. J. Bot 2015, 47, 511–515. [Google Scholar]
  14. Gras, A.; Parada, M.; Rigat, M.; Valles, J.; Garnatje, T. Folk medicinal plant mixtures: Establishing a protocol for further studies. J. Ethnopharmacol. 2018, 214, 244–273. [Google Scholar] [CrossRef] [PubMed]
  15. Leporatti, M.L.; Ivancheva, S. Preliminary comparative analysis of medicinal plants used in the traditional medicine of Bulgaria and Italy. J. Ethnopharmacol. 2003, 87, 123–142. [Google Scholar] [CrossRef]
  16. Akhmetova, A.B.; Mukhitdinov, N.M.; Ydyrys, A.; Ametov, A.A.; Inelova, Z.A.; Öztürk, M. Studies on the root anatomy of rubber producing endemic of Kazakhstan, Taraxacum kok-saghyz LE Rodin. JAPS J. Anim. Plant Sci. 2018, 28, 1400. [Google Scholar]
  17. Szőke, A. Complex Assesment of Green Roofs and of Applied Sedum Species. Doctoral Dissertation, Corvinus University of Budapest, Budapest, Hungary, 2015. [Google Scholar]
  18. Angeliev, V.; Cesmedziev, I. On the ornamental qualities and reproductive characteristics of some Bulgarian Sedum species. Nauc. Trudove Viss Sel. Stop. Inst. “V. Kolarov” Plovdiv. 1970, 19, 47–53. [Google Scholar]
  19. Kubentayev, S.A.; Kotukhov, Y.A.; Danilova, A.N.; Suleimenov, A.N.; Sumbembayev, A.A. Phytocoenotic structure and stocks of main medical plants in southern part of Altai Mountain System (East Kazakhstan). J. Comput. Theor. Nanosci. 2019, 16, 2822–2834. [Google Scholar] [CrossRef]
  20. Ydyrys, A.; Zhaparkulova, N.; Aralbaeva, A.; Mamataeva, A.; Seilkhan, A.; Syraiyl, S.; Murzakhmetova, M. Systematic analysis of combined antioxidant and membrane-stabilizing properties of several Lamiaceae family Kazakhstani plants for potential production of tea beverages. Plants 2021, 10, 666. [Google Scholar] [CrossRef]
  21. Ydyrys, A.; Zhamanbayeva, G.; Zhaparkulova, N.; Aralbaeva, A.; Askerbay, G.; Kenzheyeva, Z.; Tussupbekova, G.; Syraiyl, S.; Kaparbay, R.; Murzakhmetova, M. The Systematic Assessment of the Membrane-Stabilizing and Antioxidant Activities of Several Kazakhstani Plants in the Asteraceae Family. Plants 2024, 13, 96. [Google Scholar] [CrossRef]
  22. Leong, F.; Hua, X.; Wang, M.; Chen, T.; Song, Y.; Tu, P.; Chen, X.J. Quality standard of traditional Chinese medicines: Comparison between European Pharmacopoeia and Chinese Pharmacopoeia and recent advances. Chin. Med. 2020, 15, 76. [Google Scholar] [CrossRef]
  23. Kirimura, K.; Cao, W.; Onda, Y.; Yoshioka, I.; Ishii, Y. Selective and high-yield production of ethyl α-d-glucopyranoside by the α-glucosyl transfer enzyme of Xanthomonas campestris WU-9701 and glucose isomerase. J. Biosci. Bioeng. 2022, 134, 220–225. [Google Scholar] [CrossRef] [PubMed]
  24. Maqbool, Z.; Arshad, M.S.; Ali, A.; Aziz, A.; Khalid, W.; Afzal, M.F.; Lorenzo, J.M. Potential role of phytochemical extract from saffron in development of functional foods and protection of brain-related disorders. Oxid. Med. Cell. Longev. 2022, 2022, 6480590. [Google Scholar] [CrossRef] [PubMed]
  25. Metlyaeva, S.A.; Rodygin, K.S.; Lotsman, K.A.; Samoylenko, D.E.; Ananikov, V.P. Biomass-and calcium carbide-based recyclable polymers. Green Chem. 2021, 23, 2487–2495. [Google Scholar] [CrossRef]
  26. Jovanović, S.Č.; Jovanović, O.P.; Mitić, Z.S.; Golubović, T.D.; Zlatković, B.K.; Stojanović, G.S. Volatile profiles of the orpines roots: Hylotelephium telephium (L.) H. Ohba, H. maximum (L.) Holub and H. spectabile (Boreau) H. Ohba x telephium (L.) H. Ohba. Flavour Fragr. J. 2017, 32, 446–450. [Google Scholar] [CrossRef]
  27. Miller, A.A.; Lawton, E.J.; Balwit, J.S. The Radiation Chemistry of Hydrocarbon Polymers: I. Polyethylene, Polymethylene and Octacosane. J. Phys. Chem. 1956, 60, 599–604. [Google Scholar] [CrossRef]
  28. Okechukwu, P.N. Evaluation of anti-inflammatory, analgesic, antipyretic effect of eicosane, pentadecane, octacosane, and heneicosane. Asian J. Pharamath. Clin. Res. 2020, 13. [Google Scholar] [CrossRef]
  29. Lei, Y.; Fu, P.; Jun, X.; Cheng, P. Pharmacological properties of geraniol—A review. Planta Medica 2019, 85, 48–55. [Google Scholar] [CrossRef] [PubMed]
  30. Dawood, K.M. Benzofuran derivatives: A patent review. Expert Opin. Ther. Pat. 2013, 23, 1133–1156. [Google Scholar] [CrossRef] [PubMed]
  31. Zahra, N.; Iqbal, J.; Arif, M.; Abbasi, B.A.; Sher, H.; Nawaz, A.F.; Calina, D. A comprehensive review on traditional uses, phytochemistry and pharmacological properties of Paeonia emodi Wall. ex Royle: Current landscape and future perspectives. Chin. Med. 2023, 18, 23. [Google Scholar] [CrossRef]
  32. Joint FAO/WHO Expert Committee on Food Additives; World Health Organization. Evaluation of Certain Food Additives and Contaminants: Fifty-Third Report of the Joint FAO/WHO Expert Committee on Food Additives; World Health Organization: Geneva, Switzerland, 2000. Available online: https://iris.who.int/handle/10665/42378 (accessed on 1 July 2024).
  33. Noriega, P. Terpenes in essential oils: Bioactivity and applications. In Terpenes and Terpenoids—Recent Advances; IntechOpen: London, UK, 2020. [Google Scholar] [CrossRef]
  34. Couper, F.J.; Marinetti, L.J. gamma-Hydroxybutyrate(GHB)—Effects on Human Performance and Behavior. Forensic Sci. Rev. 2002, 14, 101–121. [Google Scholar]
  35. Zielińska-Błajet, M.; Feder-Kubis, J. Monoterpenes and their derivatives—Recent development in biological and medical applications. Int. J. Mol. Sci. 2020, 21, 7078. [Google Scholar] [CrossRef] [PubMed]
  36. Devappa, R.K.; Makkar, H.P.; Becker, K. Jatropha diterpenes: A review. J. Am. Oil Chem. Soc. 2011, 88, 301–322. [Google Scholar] [CrossRef]
  37. Lanzotti, V. Diterpenes for therapeutic use. In Natural Products; Springer: Berlin/Heidelberg, Germany, 2013; pp. 3173–3191. [Google Scholar]
  38. de Oliveira, A.M.; Tirapelli, C.R.; Ambrosio, S.R.; da Costa, F.B. Diterpenes: A therapeutic promise for cardiovascular diseases. Recent Pat. Cardiovasc. Drug Discov. (Discontin.) 2008, 3, 1–8. [Google Scholar] [CrossRef] [PubMed]
  39. Bartikova, H.; Hanusova, V.; Skalova, L.; Ambroz, M.; Bousova, I. Antioxidant, pro-oxidant and other biological activities of sesquiterpenes. Curr. Top. Med. Chem. 2014, 14, 2478–2494. [Google Scholar] [CrossRef] [PubMed]
  40. Doores, S. Organic acids. In Food Science and Technology-New York-Marcel Dekker; CRC Press: Boca Raton, FL, USA, 2005; Volume 145, p. 91. [Google Scholar]
  41. Godara, P.; Dulara, B.K.; Barwer, N.; Chaudhary, N.S. Comparative GC-MS Analysis of Bioactive Phytochemicals from Different Plant Parts and Callus of Leptadenia reticulata Wight and Arn. Pharmacogn. J. 2019, 11, 129–140. [Google Scholar] [CrossRef]
  42. Shukla, R.; Chauhan, N.; Rajak, C.; Flora, S.J.S. Flavors and Fragrances: Natural and Food-Grade Ingredients for Nutraceuticals Applications. In Flavor Development for Functional Foods and Nutraceuticals; CRC Press: Boca Raton, FL, USA, 2019; pp. 141–165. [Google Scholar]
  43. Gheibi, N.; Saboury, A.A.; Haghbeen, K.; Rajaei, F.; Pahlevan, A.A. Dual effects of aliphatic carboxylic acids on cresolase and catecholase reactions of mushroom tyrosinase. J. Enzym. Inhib. Med. Chem. 2009, 24, 1076–1081. [Google Scholar] [CrossRef] [PubMed]
  44. Sivakumar, C.; Jeganathan, K. Phytochemical profiling of cat whisker’s (Orthosiphon stamineus) tea leaves extract. J. Pharmacogn. Phytochem. 2018, 7, 1396–1402. [Google Scholar]
  45. Urquilla, A.; Merrer, D.C.; Sumner, R.; Denton, R.W. Synthesis and Biological Activity of 2-(2-Amino-2-phenylethyl)-5-oxotetrahydrofuran-2-carboxylic Acid: A Microwave-Assisted 1, 3-Dipolar Cycloaddition Approach. Synlett 2021, 32, 1735–1740. [Google Scholar]
  46. Malo de Molina, P.; Gradzielski, M. Gels Obtained by Colloidal Self-Assembly of Amphiphilic Molecules. Gels 2017, 3, 30. [Google Scholar] [CrossRef]
  47. Silva, C.L.; Pereira, J.C.; Ramalho, A.; Pais, A.A.; Sousa, J.J. Films based on chitosan polyelectrolyte complexes for skin drug delivery: Development and characterization. J. Membr. Sci. 2008, 320, 268–279. [Google Scholar] [CrossRef]
  48. Wittgenstein, E.; Berry, H.K. Reaction of dihydroxyacetone (DHA) with human skin callus and amino compounds. J. Investig. Dermatol. 1961, 36, 283–286. [Google Scholar] [CrossRef] [PubMed]
  49. Sharifi-Rad, J.; Seidel, V.; Izabela, M.; Monserrat-Mequida, M.; Sureda, A.; Ormazabal, V.; Cho, W.C. Phenolic compounds as Nrf2 inhibitors: Potential applications in cancer therapy. Cell Commun. Signal. 2023, 21, 89. [Google Scholar] [CrossRef] [PubMed]
  50. Calder, P.C.; Albers, R.; Antoine, J.M.; Blum, S.; Bourdet-Sicard, R.; Ferns, G.A.; Zhao, J. Inflammatory disease processes and interactions with nutrition. Br. J. Nutr. 2009, 101, 1–45. [Google Scholar] [CrossRef] [PubMed]
  51. Posadino, A.M.; Giordo, R.; Pintus, G.; Mohammed, S.A.; Orhan, I.E.; Fokou, P.V.T.; Sharopov, F.; Adetunji, C.O.; Gulsunoglu-Konuskan, Z.; Ydyrys, A.; et al. Medicinal and mechanistic overview of artemisinin in the treatment of human diseases. Biomed Pharmacother. 2023, 163, 114866. [Google Scholar] [CrossRef] [PubMed]
  52. Pezzani, R.; Jiménez-Garcia, M.; Capó, X.; Gürer, E.S.; Sharopov, F.; Rachel, T.Y.L.; Woutouoba, D.N.; Rescigno, A.; Peddio, S.; Zucca, P.; et al. Anticancer properties of bromelain: State-of-the-art and recent trends. Front. Oncol. 2023, 12, 1068778. [Google Scholar] [CrossRef] [PubMed]
  53. Batool, Z.; Xu, D.; Zhang, X.; Li, X.; Li, Y.; Chen, Z.; Li, L. A review on furan: Formation, analysis, occurrence, carcinogenicity, genotoxicity and reduction methods. Crit. Rev. Food Sci. Nutr. 2021, 61, 395–406. [Google Scholar] [CrossRef] [PubMed]
  54. Wierzchowski, J.; Stachelska-Wierzchowska, A.; Wielgus-Kutrowska, B.; Bzowska, A. 1,N6-ethenoadenine and other fluorescent nucleobase analogs as substrates for purine-nucleoside phosphorylases: Spectroscopic and kinetic studies. Curr. Pharm. Des. 2017, 23, 6948–6966. [Google Scholar] [CrossRef] [PubMed]
  55. Pires, S.M.; Reis, R.S.; Cardoso, S.M.; Pezzani, R.; Paredes-Osses, E.; Seilkhan, A. Sharifi-Rad, Phytates as a natural source for health promotion: A critical evaluation of clinical trials. Front. Chem. 2023, 11, 1174109. [Google Scholar] [CrossRef] [PubMed]
  56. Rajkovic, J.; Novakovic, R.; Grujic-Milanovic, J.; Ydyrys, A.; Ablaikhanova, N.; Calina, D.; Al-Omari, B. An updated pharmacological insight into calotropin as a potential therapeutic agent in cancer. Front. Pharmacol. 2023, 14, 1160616. [Google Scholar] [CrossRef]
  57. Ydyrys, A.; Abdolla, N.; Seilkhan, A.; Masimzhan, M.; Karasholakova, L. Importance of the geobotanical studying in agriculture (with the example of the Sugaty region). In E3S Web of Conferences; EDP Sciences: Les Ulis, France, 2020; Volume 222, p. 04003. [Google Scholar]
  58. Ydyrys, A.; Mukhitdinov, N.; Ametov, A.A.; Tynybekov, B.M.; Akhmetova, A.B.; Abidkulova, K.T. The States of coenpopulations of endemic, relict and rare species of plant Limonium michelsonii and their protection. World Appl. Sci. J. 2013, 26, 934–940. [Google Scholar]
  59. Ydyrys, A.; Serbayeva, A.; Dossymbetova, S.; Akhmetova, A.; Zhuystay, A. The effect of anthropogenic factors on rare, endemic plant species in the Ile Alatau. In E3S Web of Conferences; EDP Sciences: Les Ulis, France, 2020; Volume 222, p. 05021. [Google Scholar]
  60. Bukenova, E.A.; Bassygarayev, Z.M.; Akhmetova, A.B.; Altybaeva, N.A.; Zhunusbayeva, Z.K.; Ydyrys, A. Development of the method of obtaining the endogenic biostimulator from wheat green spike glumes. Res. Crops 2019, 20, 210–214. [Google Scholar]
  61. Yeszhanov, B.; Baymurzaev, N.; Sharakhmetov, S.; Mautenbaev, A.; Tynybekov, B.; Baidaulet, T. Technology of landscaping in arid zones by using biohumus from sheep wool. In E3S Web of Conferences; EDP Sciences: Les Ulis, France, 2020; Volume 169, p. 02012. [Google Scholar]
  62. Ydyrys, A. An Overview of Medical Uses and Chemical Composition of Arctium tomentosum mill. Eng. Sci. 2023, 26, 984. [Google Scholar] [CrossRef]
  63. Cao, X.; Tsukamoto, T.; Seki, T.; Tanaka, H.; Morimura, S.; Cao, L.; Tatematsu, M. 4-Vinyl-2, 6-dimethoxyphenol (canolol) suppresses oxidative stress and gastric carcinogenesis in Helicobacter pylori-infected carcinogen-treated Mongolian gerbils. Int. J. Cancer 2008, 122, 1445–1454. [Google Scholar] [CrossRef]
Separations 11 00208 g001
Figure 1. The growth of S. ewersii Ledeb. in Kazakhstan.
Figure 1. The growth of S. ewersii Ledeb. in Kazakhstan.
Separations 11 00208 g001
Separations 11 00208 g002
Figure 2. Chromatogram of S. ewersii root (underground part).
Figure 2. Chromatogram of S. ewersii root (underground part).
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Separations 11 00208 g003
Figure 3. Chromatogram of S. ewersii root (aerial part).
Figure 3. Chromatogram of S. ewersii root (aerial part).
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Separations 11 00208 g004
Figure 4. Chromatogram of S. ewersii (stem + leaves).
Figure 4. Chromatogram of S. ewersii (stem + leaves).
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Separations 11 00208 g005
Figure 5. Chromatogram of S. ewersii flowering aerial part.
Figure 5. Chromatogram of S. ewersii flowering aerial part.
Separations 11 00208 g005
Table 1. Chemical composition (%) S. ewersii L.: 1—root (underground part); 2—root (aerial part); 3—stem + leaves; 4—flowering aerial part.
Table 1. Chemical composition (%) S. ewersii L.: 1—root (underground part); 2—root (aerial part); 3—stem + leaves; 4—flowering aerial part.
№CompoundsMolecular FormulaPercentage Content, %
1234
14-Cyclopentene-1,3-dioneC5H4O20.781.340.940.70
2Butanoic acid, 4-hydroxy-C4H8O30.77-0.82-
32-FuranmethanolC5H6O21.331.582.151.54
42(5H)-FuranoneC4H4O20.831.640.66-
52-Cyclopenten-1-one, 2-hydroxy-C5H6O21.162.231.480.84
6Urea, 1-methylcyclopropyl-C5H10 H2O2.86---
7(-)-MyrtenolC10H16O19.82-1.64-
82,6-Octadien-1-ol, 3,7-dimethyl-, (Z)-C10H18O0.440.39-1.31
9GeraniolC10H18O1.903.321.54-
10(-)-cis-MyrtanolC10H18O3.670.71--
11Propanoic acid, 2-methyl-, 3-hydroxy-2,4,4-trimethylpentyl esterC12H24O30.94---
12Phenylethyl AlcoholC8H10O0.430.990.420.41
131-Cyclohexene-1-methanol, 4-(1-methylethenyl)-C10H16O0.570.56-0.48
142,5-Dimethyl-4-hydroxy-3(2H)-furanoneC6H8O30.430.651.072.89
151,4-Cyclohexadiene-1-methanol, 4-(1-methylethyl)-C10H16O1.11-2.03-
16Cyclopropyl carbinolC4H8O1.111.96-0.76
171,3-Cyclohexadiene-1-methanol, 4-(1-methylethyl)-C10H16O1.640.78--
18p-Cymen-7-olC10H14O0.760.73--
191,3-Dioxol-2-one,4,5-dimethyl-C5H6O32.445.665.132.75
202-Hydroxy-gamma-butyrolactoneC4H6O33.606.504.522.21
212-Methoxy-4-vinylphenolC9H10O21.41-1.130.58
224H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl-C6H8O41.913.664.955.26
23Phenol, 2,6-dimethoxy-C8H10O30.800.510.451.19
242-Propen-1-ol, 3-phenyl-C9H10O1.566.710.512.90
25GlycerinC3H8O31.811.961.86-
26Benzofuran, 2,3-dihydro-C8H8O1.424.6012.4314.77
27(2,2,6-Trimethyl-bicyclo[4,1,0]hept-1-yl)-methanolC11H20O0.88---
285-Oxotetrahydrofuran-2-carboxylic acid, ethyl esterC7H10O40.48---
299,12-Octadecadienoic acid, ethyl esterC20H36O21.63-1.952.94
301,2-Ethanediol, 1-(2-furanyl)-C6H8O30.801.90--
312(3H)-Furanone, dihydro-4-hydroxy- 0.671.061.14-
32Ethyl 9,12,15-octadecatrienoateC20H34O20.922.073.10-
331,4-Benzenedimethanol, α,α’-dimethyl-C10H16O20.84---
34Ethyl β-d-ribosideC7H14O51.391.880.982.12
351,4-Dimethoxy-2,3-dimethylbenzeneC10H14O20.30---
36OctacosaneC28H585.944.45--
37Ethyl (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoateC12H14O40.71---
384-((1E)-3-Hydroxy-1-propenyl)-2-methoxyphenolC10H12O30.380.840.38-
39p-Hydroxycinnamic acid, ethyl esterC11H12O30.741.20--
40Ethyl α-d-glucopyranosideC8H16O628.7920.3612.9522.04
41ButyrolactoneC4H6O2-0.891.390.39
42n-Amyl etherC10H22O-2.53--
43Bicyclo[3,1,1]hept-2-ene-2-methanol, 6,6-dimethyl-C10H16O-5.60-5.95
44Benzyl alcoholC7H8O-0.97--
45DihydroxyacetoneC3H6O3-1.621.89-
46(S)-(+)-2′,3′-DideoxyribonolactoneC5H8O3-0.890.63-
475-HydroxymethylfurfuralC6H6O3-0.820.660.63
48PhytolC20H40O-1.565.568.98
49o-Methoxy-α,α-dimethylbenzyl alcoholC9H12O2-0.46--
502-Furanmethanol, 5-ethenyltetrahydro-α,α,5-trimethyl-, cis-C10H18O2-1.11--
511,6-Anhydro-2,3-dideoxy-β-D-threo-hexopyranoseC6H10O3-0.88--
52β-d-Lyxofuranoside, methyl -1.121.90-
539-Octadecenamide, (Z)-C18H35NO-1.30--
54Propanoic acidC3H6O2--0.47-
55Butanoic acid, 2-methyl-C5H10O2--0.841.63
56Butanoic acid, 3-methylbutyl esterC9H18O2--2.60-
572-Cyclopenten-1-one, 2-hydroxy-3-methyl-C6H8O2--0.32-
581,2,3-Propanetriol, 1-acetateC5H10O4--0.32-
592-Furancarboxylic acidC5H4O3--0.38-
60PhenolC6H6O--0.140.46
611-Deoxy-d-arabitolC5H12O4--11.83-
62β-D-Ribopyranoside, methylC6H12O5--2.47-
631,3-Cyclopentanediol, cis-C5H10O2--2.71-
64Butanoic acid, 2-oxo-C4H6O3--1.71-
651-OctanolC8H18O3---0.69
66Phenol, 2,4-bis(1,1-dimethylethyl)-C14H22O---1.35
677-Oxabicyclo[4,1,0]heptane, 1-methyl-4-(2-methyloxiranyl)-C02H16O2---1.08
689,12,15-Octadecatrienoic acid, ethyl ester, (Z,Z,Z)-C20H34O2---9.41
693,4-Dihydroxy-5-methyl-dihydrofuran-2-oneC5H8O4---0.98
70Ethyl 2,3-epoxybutyrateC6H10O3---1.71
714-(p-Acetoxyphenyl)-2-butanoneC12H14O3---1.08
72Aliphatic monoterpenes 28.58%1.34%3.06%8.20%
73Oxygenated monoterpenoids 54.41%31.28%21.49%53.18%
74Diterpenoids 1.42%6.16%17.99%23.75%
75Others 15.59%61.22%57.46%14.87%
76The common compounds 100%100%100%100%
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Kobylina, T.; Novikov, A.; Sadyrova, G.; Kyrbassova, E.; Nazarbekova, S.; Imanova, E.; Parmanbekova, M.; Tynybekov, B. The Volatile Compounds Composition of Different Parts of Wild Kazakhstan Sedum ewersii Ledeb. Separations 2024, 11, 208. https://doi.org/10.3390/separations11070208

AMA Style

Kobylina T, Novikov A, Sadyrova G, Kyrbassova E, Nazarbekova S, Imanova E, Parmanbekova M, Tynybekov B. The Volatile Compounds Composition of Different Parts of Wild Kazakhstan Sedum ewersii Ledeb. Separations. 2024; 11(7):208. https://doi.org/10.3390/separations11070208

Chicago/Turabian Style

Kobylina, Tatyana, Andriy Novikov, Gulbanu Sadyrova, Elzira Kyrbassova, Saltanat Nazarbekova, Elmira Imanova, Meruyert Parmanbekova, and Bekzat Tynybekov. 2024. "The Volatile Compounds Composition of Different Parts of Wild Kazakhstan Sedum ewersii Ledeb." Separations 11, no. 7: 208. https://doi.org/10.3390/separations11070208

APA Style

Kobylina, T., Novikov, A., Sadyrova, G., Kyrbassova, E., Nazarbekova, S., Imanova, E., Parmanbekova, M., & Tynybekov, B. (2024). The Volatile Compounds Composition of Different Parts of Wild Kazakhstan Sedum ewersii Ledeb. Separations, 11(7), 208. https://doi.org/10.3390/separations11070208

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