Natural Product Sciences 27(1) : 36-44 (2021) https://doi.org/10.20307/nps.2021.27.1.36

Volatiles Composition from Aerial Parts of the Insect-Pollinated and the Promising Medicinal hypericifolia L. Growing Wild in Northern Kazakhstan

Vitaliy Kirillov1,*, Tamara Stikhareva1, Gayane Atazhanova2,3, Sezai Ercisli4, Aigerim Makubayeva2, Yana Krekova1, Alimzhan Rakhimzhanov1, and Sergazy Adekenov2 1Department of Breeding, A.N. Bukeikhan Kazakh Research Institute of Forestry and Agroforestry, Shchuchinsk 021704, Kazakhstan 2Laboratory of Chemistry of Terpenoids, International Research-and-Production Holding Company “Phytochemistry”, Karaganda 100009, Kazakhstan 3“Phytoperfume” Limited Liability Partnership, Karaganda 100009, Kazakhstan 4Department of Horticulture, Agricultural Faculty, Ataturk University, Erzurum 25240, Turkey

Abstract  The essential oils from the aerial parts (leaves and flowers) of Spiraea hypericifolia L. (), collected in Northern Kazakhstan, were obtained by distillation in two dispersion media (distilled water and 15% NaCl solution). The chemical composition of the essential oils was evaluated by GC-MS for the first time. The yield of the essential oil was 0.04% (in fresh growth conditions) and 0.02% (in dry growth conditions) respectively regardless of which dispersion media (H2O or 15% NaCl solution) was used at the isolation of essential oil. The main compounds were aliphatic hydrocarbons (alkanes) (40.6-53.2%), aldehydes (8.4-17.4%), diterpenoids (9.1-16.7%) and ketones (6.2-8.7%). Content of monoterpenoids was depended on dispersion media (2.2-3.6% where H2O was dispersion media and 8.4-8.5% where 15% NaCl solution was dispersion media). n- Heneicosane (17.4-34.1%) and n-tricosane (14.3-19.5%) were the main constituents of the essential oil of S. hypericifolia. There were many insects from different classes in S. hypericifolia at flowering. Important components such as α-methylene-γ-butyrolactone (0.8-2.8%), benzyl cyanide (0.7-1.1%), β-damascenone (1.2- 2.9%), (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene (1.8-2.7%), β-ionone (0.5-1.8%) and others were detected in small amounts. Keywords  Spiraea hypericifolia L., Essential oil composition, Dispersion media, Aliphatic hydrocarbons, Aldehydes

Introduction the assumption about later their origin. Xerophytic of the section Chamaedryon (S. hypericifolia, S. trilobata, Spiraea L. genus belongs to the family Rosaceae Juss. S. crenata) is considered the most evolutionary advanced. and distributed in temperate regions of the Northern Fossils of these species are known from the Quaternary hemisphere. The areal of the genus extends from the period only. S. hypericifolia has the most extensive Carpathians to the shores of the Pacific Ocean, from Eurasian areal.1 There are 10 species of the genus Spiraea Chukotka to Mongolia, China, Japan. Species of the L. grow in Kazakhstan, one of them is Spiraea hypericifolia genus Spiraea are found in the Caucasus, Kopet-Dag, L.2 S. hypericifolia included in the Red Books of Tomsk Pamir-Alai and Tien Shan. Chamaedryon section of Region and Republic of Tatarstan (Russian Federation). Metaspiraea Nakai subgenus of Spiraea L. genus has a S. hypericifolia is a shrub up to 150 cm height, with later origin. The areal of the section covers south of brown virgate branches bearing sessile umbrellas of Europe, Western, Eastern and Central Asia. There are no flowers. Leaves are 10-25 mm length and 1.5-8 mm width, species of the section in North America, which confirms inversely ovate, oblong-elliptic or lanceolate. Inflorescences are 4-10 flowered. Flowers are 5-8(9) mm in diameter, *Author for correspondence white. It is in blossom in April-May; it fruits from June.2 Vitaliy Kirillov, Department of Breeding, A.N. Bukeikhan Kazakh Research Institute of Forestry and Agroforestry, Shchuchinsk The habitat of the species is the European part of the 021704, Kazakhstan. Russian Federation, the Caucasus, Western and Eastern Tel: +7-71636-4-15-63, +7-701-581-57-55; E-mail: [email protected] Siberia, Eastern Europe, Turkey, Central and Minor Asia,

36 Vol. 27, No. 1, 2021 37

Mongolia, China. It grows on ravine and rocky slopes in the steppe and forest-steppe zones, in thickets of shrubs and on the banks of mountain rivers. It forms dwarf (10- 20 cm height) bushes with very small leaves with a lack of moisture in the desert-steppe areas. S. hypericifolia is sun-loving, salt resisting, gas-resistant plant.2,3 Roots, bark of branches, and leaves are used in gastrointestinal diseases, rheumatism, helminthiasis, gyne- cological diseases in Tibetan medicine. Wood is used to treat dermatoses in Kazakhstan. It has phytoncidal properties. S. hypericifolia leaves exhibit antibacterial activity against gram-positive and gram-negative bacteria. Infusion of flowers is used in algomenorrhea.4-6 Russian scientists found that extract of the aerial parts of S. hypericifolia has high antioxidant and antiviral activity. Fig. 1. General view of S. hypericifolia (12 June 2019). The antiviral activity of extract exceeds the activity of the antiviral medication Tamiflu (Oseltamivir Phosphate). (23.6%), and ethyl linolenate (14.6%). The essential oil This fact makes S. hypericifolia promising for medical use.7 showed good to moderate DPPH free radical scavenging Branches are suitable for the manufacture of whip- activity, while had no apparent antimicrobial activity.19 handles, walking-sticks, turning products. S. hypericifolia Thus, the present study was conducted to investigate can be used as feed for cattle, camels, horses, deer, roe for the first time the composition of essential oil from the deer, grouse, for example, it is feed for goats in Mongolia. aerial parts (leaves and flowers) of S. hypericifolia S. hypericifolia recommended for greening in the forest- growing wild in Northern Kazakhstan from two different steppe, well cut. It is soil strengthener. It is used for locations and in two different dispersion media (distilled fastening of sands. It is a good honey plant.4 S. hypericifolia water and 15% NaCl solution). burns well and quickly, giving a strong heat. The Kazakh people are used its smoke for fumigation of sabu (a Experimental leather or wooden container for making kumys (fermented milk product made from mare's milk)), and smoldering Plant material – Aerial parts (leaves and flowers) of S. stalks are used to smoke lamb and horsemeat.8 hypericifolia growing wild were collected at the flowering S. hypericifolia contains proanthocyanidins, catechins, stage in Northern Kazakhstan (see Fig. 1, Table 1) in 12 flavonoids, carotenoids, organic acids, coumarins, saponins, June 2019. were identified and authenticated by Dr tannins, essential oil, and vitamin C (in the leaves).4-6,9-16 Tamara Stikhareva with the use of “Flora of Kazakhstan” Literature review shows no reports on essential oil as the key for the plants.2 Voucher specimens were kept at composition of S. hypericifolia. The essential oil obtained the Department of Breeding of A.N. Bukeikhan Kazakh microwave-assisted hydrodistillation at 990 W power Research Institute of Forestry and Agroforestry with levels for a period of 2 h from air-dried leaves of Spiraea number 12.06.2019/12. alpine Pall., growing in Southwest China (yield of the oil Essential oil isolation – The essential oils were obtained 0.87%), was contained linolenic acid ethyl ester (18.3%), by distillation of 100 g fresh plant samples (aerial parts) in palmitic acid (9.8%), cinnamic acid (5.9%), trans-phytol two dispersion media: distilled water and 15% NaCl (5.4%), ethyl palmitate (5.2%), and linalool (2.8%).17 solution20 for 3 hours in the Clevenger-type apparatus There are a data about chemical composition of the using the hydrodistillation method. volatile components from leaves of Spiraea trilobata L. Gas Chromatography-Mass Spectrometry (GC-MS) – using HS-SPME&GC-MS. The volatiles of S. trilobata The qualitative and quantitative compositions of the growing in Northern China was contained trans-2-hexen- specimens of essential oils were analyzed by GC-MS on 1-ol (35.1%) and trans-2-hexenyl esters (50.9%).18 The an Agilent Technologies 7890А GC System gas chroma- essential oil, extracted from the dried twigs and leaves of tograph with an Agilent Technologies 5975С mass selective Spiraea mongolica Maxim. by hydrodistillation and detector. An HP-5MS capillary column (5% Phenyl identified by GC-MS, was contained fatty acids and their Methyl Silox, 30 m × 250 mm × 0.25 mm) at the flow derivatives, ethyl palmitate (38.6%), ethyl linolelaidate rate of gas-carrier of helium 1 mL/min was used. The 38 Natural Product Sciences

Table 1. Description of the collected S. hypericifolia Yield of the oil, %* Latitude and Dispersion Sample Locality of collection Description of collection Dispersion longitude media – 15% media – H O 2 NaCl solution Glade, fresh growth conditions. Feather grass and forbs community with the Northern Kazakhstan, dominance in grass stand of Filipendula hexapetala Akmola region, State Gilib., Stipa capillata L., Cerastium falcatum (Ser.) 52°56'N: I 0.04 0.04 National Natural Park Bunge and others. S. hypericifolia is dominated of 70°18'E “Burabay” shrubs. The total projective cover – 80-85%. The projective cover of S. hypericifolia – 70-80%. The height of S. hypericifolia – 75-140 cm. Glade, dry growth conditions. Northern Kazakhstan, Forbs and fescue community with the dominance in Akmola region, Branch grass stand of Festuca sulcata Hack., Filipendula of Northern region of hexapetala Gilib., and Fragaria viridis Weston and 52°56'N: II the Republican State 0.02 0.02 others. S. hypericifolia is dominated of shrubs. The 70°16'E Communal Enterprise total projective cover – 60-70%. The projective cover “Republican Forest of S. hypericifolia – 30-40%. The height of S. Breeding Center” hypericifolia – 40-130 cm. * Content of essential oil is given in % in regard to the mass of fresh raw material. temperature of the vaporizer was 240 oC. For 5 minutes volatile compounds usually follow Henry’s law. Under the temperature of the column has been 40 oC, with the these very dilute conditions, all solute molecules are programming of the temperature up to 240 oC at the rate surrounded by solvent molecules, making solute-solute of the change of the temperature 5 oC/minute, and then interactions unimportant; however, the molecules of this column has been set into isometric mode of operation solute and solvent may be physically different. When salts for 53.4 minutes. The samples (0.1 µL) were injected with are added to solutions of dissolved volatile com- pounds, flow division 5:1. Conditions of the recording of mass the activity coefficient and the headspace concentration spectra were 70 eV, the range of mass was m/z 10-350. are greater than predicted by Henry’s law due to mutual The percent contents of the constituents were calculated interactions of the solutes and solvents.22 The amount of automatically using peak areas in the total ion chroma- increase in volatility in the presence of salts is dependent togram without using correction factors. on the volatile compound. For example, increasing the Identification of the components – Constituents were concentration of NaCl increased ethyl acetate and diacetyl identified using mass spectra, retention times, and the in the headspace concentration; in apple juice, the Wiley GC/MS library. The results were also confirmed by addition of NaCl did not change esters, while aldehydes the comparison of the compounds with their relative and alcohols increased in the headspace concentration; retention indices in the literature21 and NIST Chemistry 15% NaCl solution significantly increased both perceived WebBook, SRD 69. To obtain the retention indices there aroma and headspace concentrations of menthone. NaCl was used a standard solution of n-alkanes (C8-C24). increases the perceived intensity or headspace concentra- tions as compared to water.22,23 Increasing concentration Results and Discussion of 15% NaCl resulted in greater numbers of identified flavor components from Capsella bursa-pastoris by The yield of the essential oil in the Samples I and II steam distillation.20 We can note the salting effect on was 0.04% and 0.02% respectively regardless of which distribution of some compounds in the essential oil of S. dispersion media (H2O or 15% NaCl solution) was used hypericifolia. Hydrodistillation of raw material in 15% at the isolation of essential oil. Essential oil of S. NaCl solution increased the concentration of monoter- hypericifolia is light green color movable liquid with a penoids, furanoids (their content was not detected during specific scent. The oil yield has not changed, but the hydrodistillation in water), sesquiterpene lactones (Sample content of the individual volatile compounds has changed. II), phenols, fatty acids (Sample II), diterpenoids (in It is known that salts increase the headspace con- Sample II slightly), but reduced the concentration of centration of volatile compounds. In dilute water solutions, homoterpenes, aldehydes, ketones (in Sample I did not Vol. 27, No. 1, 2021 39 change), aliphatic hydrocarbons (alkanes) in essential oil The main compounds of the essential oil from leaves as compared to water. and flowers of S. hypericifolia were aliphatic hydrocarbons Forty three components were detected and thirty nine (alkanes) (40.6-53.2%), aldehydes (8.4-17.4%), diterpenoids components were identified in the essential oil of S. (9.1-16.7%) and ketones (6.2-8.7%). Content of monoter- hypericifolia and presented in Table 2 and Fig. 2-3. penoids depended on dispersion media, thus 2.2-3.6%

Table 2. Percentage composition of the essential oil from leaves and flowers of S. hypericifolia Content of components in samples (%) III Constituent RT (min) RIa RI b lit Dispersion Dispersion Dispersion Dispersion media – 15% media – 15% media – H O media – H O 2 NaCl solution 2 NaCl solution Dihydro-3-methylene-2(3H)-furanone (α- 12.793 892 - 1.1 0.8 - 2.8 Methylene-γ-butyrolactone) Octanal (n-Caprylaldehyde) 13.579 1005 982 0.6 - - - trans-Linalool oxide 15.902 1042 1047 - 1.7 - 2.4 α-Terpinolene 16.416 1052 1078 - 1.7 - 1.6 L-Linalool 16.800 1082 1097 1.1 1.2 0.9 1.7 Nonanal (n-Nonaldehyde) 16.942 1104 1105 3.8 2.2 1.3 1.9 Benzyl nitrile (Benzyl cyanide) 18.024 1138 1143 0.7 1.1 - - α-Terpineol ((S)-α,α,4-Trimethyl-3- 19.605 1143 1172 1.7 4.5 1.3 5.2 cyclohexene-1-methanol) n-Decanal (Capraldehyde) 20.037 1197 1183 1.6 1.1 0.7 0.8 4-Vinylphenol 20.405 1222 1224 - - - 2.2 (E)-2-Decenal 21.644 1230 1236 0.9 1.2 0.8 1.2 n-Undecanal 22.904 1303 1305 1.2 0.7 0.7 - 2-Methoxy-4-vinylphenol 23.109 1315 1315 - 1.7 1.1 3.8 Cinnamic acid methyl ester (2-Propenoic 24.957 1336 1344 0.8 - - - acid, 3-phenyl-, methyl ester) β-Damascenone ((E)-1-(2,6,6-Trimethyl- 25.018 1360 1361 1.2 2.9 - 2.0 1,3-cyclohexadien-1-yl)-2-buten-1-one) Unidentified component 25.106 1382 - - 0.9 0.5 1.1 n-Dodecanal (Lauraldehyde) 25.585 1394 1386 3.6 2.4 2.6 1.8 Unidentified component 26.245 1416 - - 0.7 - - cis-Geranylacetone 26.770 1420 1426 0.8 1.0 - - 4,11-Dimethyltetradecane 27.011 1452 1462 1.9 1.4 1.3 1.1 β-Ionone 27.845 1457 1463 1.3 1.8 0.5 0.9 n-Tridecanal 28.582 1492 1490 3.6 2.0 2.7 1.7 Dodecanoic acid 30.870 1560 1556 - - 2.7 5.0 (E,E)-4,8,12-Trimethyl-1,3,7,11- 31.391 1577 1580 2.7 2.4 2.4 1.8 tridecatetraene n-Pentadecanal 33.003 1702 1707 0.6 - 0.6 - n-Heptadecanal 36.978 1718 1716 1.5 1.1 1.6 1.0 Cinnamic acid pentyl ester (2-Propenoic 37.639 1753 1755 0.7 1.8 - - acid, 3-phenyl-, pentyl ester) Benzyl benzoate 38.126 1762 1762 - - 0.6 - Neophytadiene 39.526 1774 1790 3.8 5.8 4.1 3.4 Hexahydrofarnesyl acetone 39.628 1835 1845 6.2 4.0 6.6 3.3 (Z)-1,3-Phytadiene 39.923 1856 1862 1.7 2.4 1.9 1.4 Isophytol 40.196 1922 1939 3.0 4.0 3.1 2.5 40 Natural Product Sciences

Table 2. continued Content of components in samples (%) III Constituent RT (min) RIa RI b lit Dispersion Dispersion Dispersion Dispersion media – 15% media – 15% media – H O media – H O 2 NaCl solution 2 NaCl solution Unidentified component 40.740 1942 - 1.1 1.0 1.4 - n-Hexadecanoic acid (Palmitinic acid) 41.330 1963 1964 - - 0.6 - (E,E,E)-3,7,11,15-Tetramethylhexadeca- 41.398 1971 1969 0.6 - 1.3 1.1 1,3,6,10,14-pentaene (E,E)-Geranyl linalool ((E,E)-3,7,11,15- 42.158 2026 2034 - - 2.6 1.3 tetramethyl-1,6,10,14-Hexadecatetraen-3-ol) Unidentified component 42.617 2094 - 1.4 1.9 0.7 0.8 n-Heneicosane 42.921 2100 2100 34.1 23.3 23.3 17.4 Phytol 43.071 2114 2104 - 1.3 3.5 7.0 n-Docosane 43.938 2200 2200 1.2 1.5 1.3 1.3 n-Tricosane 45.123 2300 2300 14.3 15.6 19.5 14.5 n-Tetracosane 46.504 2400 2400 - - 1.0 1.0 n-Pentacosane 48.260 2500 2500 1.3 2.8 6.8 5.3 Total 100.0 100.0 100.0 100.0 Sesquiterpene lactones 1.1 0.8 - 2.8 Furanoids - 1.7 - 2.4 Monoterpenoids 3.6 8.4 2.2 8.5 Homoterpenes 2.7 2.4 2.4 1.8 Aldehydes 17.4 10.7 11.0 8.4 Ketones 8.7 8.7 7.1 6.2 Phenols - 1.7 1.1 6.0 Benzyl cyanides 0.7 1.1 - - Esters 1.5 1.8 0.6 - Fatty acids - - 3.3 5 Diterpenoids 9.1 13.5 16.5 16.7 Aliphatic hydrocarbons (alkanes) 52.8 44.6 53.2 40.6 Identified compounds 97.6 95.4 97.4 98.4 Note: a Retention Indices on HP-5ms column; b Retention Indices in literature21 and NIST Chemistry WebBook, SRD 69

monoterpenoids were in essential oil where H2O was The origin of saturated, long-chained and odd- dispersion media and 8.4-8.5% monoterpenoids where numbered n-alkanes as n-heneicosane and n-tricosane in 15% NaCl solution was dispersion media. the essential oil of S. hypericifolia can be explained by the Aliphatic hydrocarbons (alkanes) n-heneicosane and n- fact that they produced by the epidermis and located in tricosane (Fig. 4) were the main constituents of the the cuticular waxes of leaves.24,25 n-Heneicosane and n- essential oil of S. hypericifolia. Content of n-heneicosane tricosane produced by plants as antimicrobial metabolites 26,27 in Sample I was 34.1% where dispersion media was H2O for pathogen protection and prevent green tissues from and 23.3% where dispersion media was 15% NaCl UV-related stress and desiccation.28 n-Heneicosane and n- solution, and in Sample II - 23.3% and 17.4% respectively. tricosane in flowers play a major role as a pollinator Content of n-tricosane in Sample I was 14.3% where attractants.29 It should be noted that there were many dispersion media was H2O and 15.6% where dispersion insects from different classes in S. hypericifolia when media was 15% NaCl solution, and in Sample II – 19.5% collecting leaves and flowers. and 14.5% respectively. Alkanes, n-alkanyl and n-alkenyl aldehydes play an Vol. 27, No. 1, 2021 41

Fig. 2. GS-MS chromatogram of the essential oil volatile components from leaves and flowers of S. hypericifolia from sample I, distilled in water (A) and in 15% NaCl solution (B). important role as defense substances against insects or communicate between or within plants.30,31 Aldehydes n- other animals. Aldehydes are volatile organic compounds octanal, n-nonanal, n-decanal, (E)-2-decenal, n-undecanal, and are released from flowers or vegetative parts of plant n-dodecanal, n-tridecanal, n-pentadecanal, n-heptadecanal to repel herbivores, attract pollinators and predators, and are found in the essential oil from leaves and flowers of S. 42 Natural Product Sciences

Fig. 3. GS-MS chromatogram of the essential oil volatile components from leaves and flowers of S. hypericifolia from sample II, distilled in water (A) and in 15% NaCl solution (B). hypericifolia in the amounts of 8.4-17.4%. acid pentyl ester (0.7-1.8%), cis-geranylacetone (0.8- Composition of essential oils of Samples I and II were 1.0%) were presented in Sample I only, and 4-vinylphenol mostly identical, however, octanal (0.6%), benzyl cyanide (2.2%), dodecanoic acid (2.7-5.0%), benzyl benzoate (0.7-1.1%), cinnamic acid methyl ester (0.8%), cinnamic (0.6%), palmitinic acid (0.6%), (E,E)-geranyl linalool Vol. 27, No. 1, 2021 43

Fig. 4. The structures of important components.

(1.3-2.6%), n-tetracosane (1.0%) were presented in Sample is produced by many plants in response to herbivory37 and II only. Probably these differences connected with growth is mainly emitted from injured tissues. The exact bio- conditions since Sample I was grown in fresh growth synthetic route to (E,E)-4,8,12-trimethyl-1,3,7,11-tride- conditions (conditions in which the amount of soil catetraene still remain unclear. But it is believed that it is moisture is sufficient for a favorable development of the derived from geranyl-linalool by oxidative degradation plants) and Sample II was grown in dry growth conditions possibly catalyzed by cytochrome P450 enzymes.31 (E,E)- (conditions in which the amount of soil moisture is 4,8,12-Trimethyl-1,3,7,11-tridecatetraene was found in the insufficient for optimal plant development). essential oil from leaves and flowers of S. hypericifolia in We should also pay attention to some components the amounts of 1.8-2.7% and its precursor geranyl- which present in the essential oil in small amounts. For linalool in the amounts of 1.3-2.6%. example, dihydro-3-methylene-2(3H)-furanone (α-methylene- β-Damascenone, β-ionone and hexahydrofarnesyl acetone γ-butyrolactone), or tulipalin A (Fig. 4), is a volatile are volatile apocarotenoids (carotenoid derived volatiles) insecticidal component and released only when the plant which are mainly produced from carotenoids oxidation by was damaged. Tulipalin A was isolated also in Spiraea carotenoid cleavage dioxygenase. Volatile apocarotenoids thunbergii Siebold ex Blume. It is a growth inhibitor resulting from the asymmetric cleavage of carotenoids against bacteria, provides resistance to fungal disease and represent a class of volatile organic compounds that plays the role of a protective substance against insect contribute to flavors and aromas.38 For example, β- attack.32 α-Methylene-γ-butyrolactone was detected in the damascenone and β-ionone (Fig. 4) are important scent essential oil of S. hypericifolia in the amounts of 0.8-2.8%. compounds in roses.39 β-Damascenone has been identified Benzyl nitrile (benzyl cyanide), or 2-phenylacetonitrile as a key odor in peach, lychee, grape and others.40 β- (Fig. 4), is a highly volatile component, serves as a signal Damascenone, β-ionone and hexahydrofarnesyl acetone of a conspecific communication in locust aggregations, of were detected in the essential oil of S. hypericifolia in the growth inhibitory in microbe-microbe interactions, of a amounts of 1.2-2.9%, 0.5-1.8% and 3.3-6.6% respectively. repellent in plant-insect interactions.33 Oral secretions, Neophytadiene (3.4-5.8%), (Z)-1,3-phytadiene (1.4- produced by herbivorous insects and containing substances, 2.4%), isophytol (2.5-4.0%) and phytol (1.3-7.0%) are elicit plant responses and plant elicitor peptides prevalence products of chlorophyll degradation occurring during through plants.34,35 In response, the plant produces diverse hydrodistillation, is components of essential oil of S. chemical active substances one of them benzyl cyanide.36 hypericifolia. Benzyl cyanide was detected in the essential oil of S. In prospect, due to the content of different classes of hypericifolia in the amounts of 0.7-1.1% in Sample I only. biologically active substances, such as aliphatic hydro- (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene (Fig. 4) carbons (n-heneicosane, n-tricosane), sesquiterpene lactones, 44 Natural Product Sciences furanoids, monoterpenoids, aldehydes, benzyl cyanides, (15) Karpova, E. A.; Lapteva, N. P. Turczaninowia 2014, 17, 42-56. ketones, phenols the essential oil can be used as anti- (16) Karpova, E. A.; Imetkhenova, O. V. Turczaninowia 2015, 18, 108- 115. microbial agent, attractant, repellent. The advantage is the (17) Teng, Y.; Yang, Q.; Yu, Z.; Zhou, G.; Sun, Q.; Jin, H.; Hou, T. availability of plant raw material, environmental and World J. Microbiol. Biotechnol. 2010, 26, 9-14. biological safety. (18) Jin, Z.; Zhang, J. J. Shanxi Agricultural Sciences 2017, 45, 729- 731. (19) Zhang, W. H.; Qian, H.; Song, Y. J.; Shen, T. Modern Food Science Acknowledgments and Technology. 2017, 33, 89-95. (20) Choi, H. S.; Lee, M. S. Korean J. Food Sci. Technol. 1996, 28, This research is funded by the Ministry of Ecology, 827-833. Geology and Natural Resources of the Republic of (21) Adams, R. P. Identification of Essential Oil Components by Gas Chromatography: Quadrupole Mass Spectroscopy; Allured Publishing Kazakhstan (No. BR10263776). Corporation; USA, 2001, p 456. (22) Ebeler, S. E.; Pangborn, R. M.; Jennings, W. G. J. Agric. Food References Chem. 1988, 36, 791-796. (23) Poll, L.; Flink, J. M. Food Chem. 1984, 13, 193-207. (24) Carriere, F.; Chagvardieff, P.; Gil, G.; Pean, M.; Sigoillot, J. C.; (1) Rusanov, F. N.; Slavkina, T. I. In Dendrology of Uzbekistan: Tapie, P. Plant Sci. 1990, 71, 93-98. Rosaceae Vol. 4; Raikova, I. A. Ed; Species of the genus Spiraea (25) Alves-Pereira, I. M. S.; Fernandes-Ferreira, M. Phytochemistry introduced in the Botanical Garden of Academy of Sciences of Uzbek 1998, 48, 795-799. SSR; USSR, 1972, pp 196-304. (26) Soliman, S. S. M.; Abouleish, M.; Abou-Hashem, M. M. M.; (2) Pavlov, N. V. Flora of Kazakhstan. Vol. 4; Academy of Sciences of Hamoda, A. M.; El-Keblawy, A. A. Plants 2019, 8, 132. the Kazakh SSR Publishing house: USSR, 1961, p 548. (27) Tao, C.; Wu, J.; Liu, Y.; Liu, M.; Yang, R.; Lv, Z. Eur. Food Res. (3) Vstovskaya, T. N.; Koropachinskiy, I. Yu. Woody plants of the Technol. 2018, 244, 881-891. Central Siberian Botanical Garden; Siberian Branch of Russian Academy (28) Pilon, J.; Lambers, H.; Baas, W.; Tosserams, M.; Rozema, J.; of Sciences Publishing House: Russia, 2005, p 235. Atkin, O. K. Phytochemistry. 1999, 50, 571-580. (4) Sokolov, P. D. Plant resources of the USSR: Flowering plants, their (29) Ayasse, M. L. In Biology of Floral Scent: Floral scent and chemical composition, the use; The families Hidrangeaceae - Haloragaceae; pollinator attraction in sexually deceptive orchids; Dudareva, N., Science; USSR, 1987, p 328. Pichersky, E. Ed; CRC Press; Taylor and Francis Group; UK, 2006, pp (5) Kudaibergen, A. A.; Dyusebaeva, M. A.; Ydyrys, A.; Feng, Y.; 219-241. Jenis, J. Int. J. Biol. Chem. 2019, 12, 128-134. (30) Kessler, A.; Baldwin, I. T. Science 2001, 291, 2141-2144. (6) Kudaibergen, А. А.; Nurlybekova, A. K.; Dyusebaeva, М. А.; Feng, (31) Dudareva, N.; Negre, F.; Nagegowda, D. A.; Orlova, I. Crit. Rev. Y.; Jenis, J. News of the National Academy of Sciences of the Republic of Plant Sci. 2006, 25, 417-440. Kazakhstan-series Chemistry and Technology 2020, 4, 73-79. (32) Kim, C. S.; Hara, T.; Datta, P. K.; Itoh, E.; Horiike, M. Biosci. (7) Kostikova, V. A.; Filippova, E. I.; Vysochina, G. I.; Mazurkova, N. Biotechnol. Biochem. 1998, 62, 1546-1549. A. In Conservation of Plant Diversity in Botanical Gardens: traditions, (33) Wei, J.; Shao, W.; Cao, M.; Ge, J.; Yang, P.; Chen, L.; Wang, X.; current situation and future: Proceedings of the International Conference Kang, L. Sci. Adv. 2019, 5, eaav5495. commemorating the 70-th anniversary of Central Siberian Botanical (34) Bonaventure, G.; Van Doorn, A.; Baldwin, I. T. Trends Plant Sci. Garden (Novosibirsk, 1-8 August, 2016); CSBG SB RAS; Russia, 2016, 2011, 16, 294-299. pp 156-157. (35) Huffaker, A.; Pearce, G.; Veyrat, N.; Erb, M.; Turlings, T. C. J.; (8) Fomin, V. N.; Usmanova, E. R.; Zhumashev, R. M.; Pokussayev, A. Sartor, R.; Shen, Z.; Briggs, S. P.; Vaughan, M. M.; Alborn, H. T.; Teal, P. V.; Motuza, G.; Omarov, Kh. B.; Kim, Yu. Yu.; Ishmuratova, M. Yu. E. A.; Schmelz, E. A. Proc. Natl. Acad. Sci. U. S. A. 2013, 110, 5707- Bulletin of the Karaganda University Chemistry Series 2018, 91, 64-73. 5712. (9) Goryaev, M. I. Essential oils of the USSR Flora; Academy of (36) Maffei, M. E.; Arimura, G.; Mithöfer, A. Nat. Prod. Rep. 2012, 29, Sciences of the Kazakh SSR Publishing house: USSR, 1952, p 380. 1288-1303. (10) Chumbalov, T. K.; Pashinina L. T.; Storozhenko, N. D. Chem. Nat. (37) Attaran, E.; Rostás, M.; Zeier, J. Mol. Plant Microbe Interact. Compd. 1974, 10, 534. 2008, 21, 1482-1497. (11) Chumbalov, T. K.; Pashinina, L. T.; Storozhenko, N. D. Chem. Nat. (38) Mousavi, S. P.; Motamed, S. M. Nat. Prod. Sci. 2020, 26, 132-135. Compd. 1975, 11, 440. (39) Baldermann, S.; Yang, Z.; Sakai, M.; Fleischmann, P.; Watanabe, (12) Chumbalov, T. K.; Pashinina, L. T.; Storozhenko, N. D. Chem. Nat. N. Floriculture Ornamental Biotech. 2009, 3, 89-97. Compd. 1976, 12, 94-95. (40) Pineau, B. D.; Barbe, J. C.; Van Leeuwen, C.; Dubourdieu, D. J. (13) Chumbalov, T. K.; Pashinina, L. T.; Storozhenko, N. D. Chem. Nat. Agric. Food Chem. 2007, 55, 4103-4108. Compd. 1976, 12, 232-233. (14) Budantsev, A. L. Plant resources of Russia: Wild growing Received December 25, 2020 flowering plants, their component composition and biological activity. Revised February 20, 2021 Vol. 2. Family Actinidiaceae - Malvaceae, Euphorbiaceae - Haloragaceae; Accepted February 23, 2021 KMK Association of Scientific Publications: Saint-Petersburg, Moscow, Russia, 2009; p 512.