Artemisia sublessingiana Krasch. ex Poljakov (Asteraceae) is a perennial herbaceous plant that grow in eastern, central, southern, and southeastern Kazakhstan [1].
Raw material for the studies was collected in the budding phase during an expedition in the third decade of August 2019 in the vicinity of Zhezqazghan (Karaganda Region). A specimen (2019.08.28.04.01) is preserved in the herbarium of the Biology-Geography Faculty of E. A. Buketov Karaganda University.
Previously, flavonoids (isorhamnetin-3-O-rutinoside and 5,7,4′-trihydroxy-6,3′-dimethoxyflavone) and a sesquiterpene lactone (arsubin) [1, 2]; the flavonoids eupatilin, 3′,4′-dimethoxyluteolin, 5,7,3′-trihydroxy-6,4′,5′-trimethoxyflavone, hispidulin, apigenin, and velutin and the sesquiterpene lactone 8α,14-dihydroxy-11,13-dihydromelampolide [3] were isolated from this plant. Compounds isolated by us were tested in silico against COVID-19 main protease enzyme (Mpro). Flavonoid compounds turned out to be highly promising with respect to the discovery of drugs for the COVID-19 pandemic [3].
The contents of the valuable constituent santonin in various Artemisia species were reported [4]. It was found that A. sublessingiana contained ~0.16 g of santonin per 100 g of air-dried raw material. The elemental composition of ash from A. sublessingiana and the fatty-acid and amino-acid compositions were previously studied [5].
According to the literature, the essential oil composition of A. sublessingiana has not been previously studied. In continuation of the determination of essential oil compositions of Artemisia species [6–8], it was studied by us using gas-chromatography–mass-spectrometry (GC-MS).
Essential oil of A. sublessingiana was obtained from various plant parts (aerial part, seeds, stems) by steam distillation in a Clevenger apparatus using hexane as a trap [9].
GC-MS analysis of A. sublessingiana essential oils was performed under conditions analogous to those in the literature [10] using a Restek Rxi®-1ms capillary column (0.25 mm × 30 m × 0.25 μm). Constituents were identified using the NIST 2014 database. Table 1 presents the constituent composition of the A. sublessingiana essential oils. The main constituents (> 3.0%) of the essential oils from the aerial part were 3-thujanone (18.9%), chrysanthenone (3.6%), camphor (17.9%), cis-chrysanthenyl acetate (31.3%), and nerol acetate (3.1%); from seeds, 1,8-cineol (12.0%), β-thujone (31.8%), 3-thujanone (18.4%), and camphor (14.8%); from stems, 1,8-cineol (11.8%), β-thujone (15.5%), 3-thujanone (34.3%), and camphor (17.2%).
Table 1.
Constituent Composition of Essential Oil from A. sublessingiana
| Constituent | RII | Essential oil content, % | ||
|---|---|---|---|---|
| stems | aerial part | seeds | ||
| 7-Methyl-3,4-octadiene | 843 | 0.2 | 0.1 | |
| Ethyl 3-methylbutanoate | 848 | 0.1 | 0.2 | 0.1 |
| Tricyclene | 915 | 0.2 | 0.1 | 0.1 |
| α-Pinene | 925 | 0.2 | 1.2 | 0.3 |
| Camphene | 939 | 2.2 | 1.8 | 2.3 |
| Sabinene | 963 | 0.7 | 0.2 | 0.8 |
| β-Pinene | 966 | 0.2 | 0.1 | 0.2 |
| Mesitylene | 983 | 0.2 | ||
| Pseudocumene | 983 | 0.1 | ||
| Unk. 1 | 985 | 0.1 | ||
| α-Terpinene | 1008 | 0.2 | 0.2 | |
| 1,2,4-Trimethylbenzene | 1010 | 0.2 | ||
| α-Cymene | 1016 | 0.7 | 0.4 | 0.8 |
| α-Limonene | 1020 | 0.1 | ||
| β-Phellandrene | 1021 | 0.1 | ||
| 1,8-Cineol | 1027 | 11.8 | 1.1 | 12.0 |
| γ-Terpinene | 1051 | 0.4 | 0.1 | 0.3 |
| cis-Sabinene hydrate | 1068 | 0.1 | ||
| Unk. 2 | 1085 | 0.1 | ||
| Filifolone | 1097 | 0.6 | 0.1 | |
| β-Thujone | 1106 | 15.5 | 1.5 | 31.8 |
| 3-Thujanone | 1115 | 34.3 | 18.9 | 18.4 |
| Chrysanthenone | 1118 | 0.6 | 3.6 | 0.6 |
| α-Campholenal | 1121 | 0.1 | ||
| cis-2-Menthenol | 1121 | 0.5 | ||
| trans-Pinocarveol | 1135 | 0.9 | 0.3 | |
| cis-Sabinol | 1136 | 0.1 | ||
| Camphor | 1141 | 17.2 | 17.9 | 14.8 |
| Unk. 3 | 1144 | 0.5 | ||
| Pinocarvone | 1153 | 0.5 | 0.9 | 0.3 |
| cis-Chrysanthenol | 1157 | 0.5 | 0.3 | 0.3 |
| Isothujol | 1159 | 0.1 | ||
| 1,3,4-Trimethyl-3-cyclohexenyl-1-carboxaldehyde | 1160 | 0.1 | ||
| Borneol | 1163 | 1.5 | 0.3 | 0.9 |
| Terpinen-4-ol | 1171 | 1.2 | 0.4 | 0.9 |
| p-Cymen-8-ol | 1180 | 0.2 | 0.2 | 0.1 |
| α-Terpineol | 1187 | 0.4 | ||
| Myrtenal | 1190 | 0.2 | 0.2 | 0.1 |
| Myrtenol | 1193 | 0.6 | 0.2 | |
| 3-Methylbut-3-enyl (E)-2-methylbut-2-enoate | 1195 | 0.1 | ||
| trans-Piperitol | 1201 | 0.2 | ||
| Verbenone | 1203 | 0.1 | ||
| Unk. 4 | 1207 | 0.3 | ||
| p-Cymenol | 1231 | 0.1 | ||
| Ciminal | 1235 | 0.2 | 0.1 | |
| Carvone | 1241 | 0.3 | 0.3 | 0.2 |
| Piperitone oxide | 1249 | 0.1 | ||
| Piperitone | 1253 | 0.6 | 0.2 | |
| cis-Chrysanthenol acetate | 1254 | 31.3 | ||
| α-Citral | 1265 | 0.2 | ||
| Bornyl acetate | 1280 | 0.1 | 0.5 | |
| Unk. 5 | 1281 | 0.1 | ||
| trans-Sabinyl acetate | 1289 | 0.8 | 0.5 | 0.5 |
| Methyl cis-cinnamate | 1297 | 0.2 | ||
| Thymol | 1299 | 0.1 | ||
| Carvacrol | 1302 | 0.2 | ||
| Unk. 6 | 1309 | 0.1 | 0.7 | 0.1 |
| Myrtenyl acetate | 1318 | 0.2 | ||
| Hexyl tiglate | 1329 | 0.2 | ||
| trans-Dihydrocarvyl acetate | 1332 | 0.1 | ||
| α-Terpinyl acetate | 1341 | 0.1 | ||
| cis-Chrysanthenyl propionate | 1346 | 0.1 | ||
| Nerol acetate | 1379 | 3.1 | ||
| 2-(Acetylmethyl)-3-carene | 1389 | 0.5 | ||
| cis-Jasmone | 1392 | 0.3 | 0.2 | |
| 2-Ethylidene-6-methyl-3,5-heptadienal | 1394 | 0.1 | 0.8 | 0.2 |
| Isocaryophyllene | 1403 | 0.1 | ||
| Aristolene | 1454 | 0.1 | 0.2 | 0.1 |
| cis-Muurol-3,5-diene | 1459 | 0.1 | ||
| Germacrene D | 1460 | 0.3 | ||
| 2-Isopropenyl-4a,8-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene | 1462 | 0.3 | ||
| γ-Gurjunene | 1473 | 0.1 | ||
| Artedouglasia oxide C | 1499 | 0.2 | 0.1 | |
| Laciniata furanone G | 1502 | 0.2 | 0.2 | |
| Artedouglasia oxide A | 1513 | 0.3 | 0.1 | |
| Laciniata furanone F | 1519 | 0.3 | 0.1 | |
| Laciniata furanone E | 1528 | 0.2 | 0.2 | |
| Laciniata furanone H | 1539 | 0.2 | 0.1 | |
| Spathulenol | 1562 | 0.2 | 0.2 | 0.2 |
| Artedouglasia oxide D | 1565 | 0.2 | ||
| 2-Phenylethyl tiglate | 1572 | 0.5 | ||
| Isobutyl pentanoate | 1581 | 0.2 | ||
| τ-Cadinol | 1646 | 0.1 | ||
| (1R,7S,E)-7-Isopropyl-4,10-dimethylenecyclodec-5-enol | 1676 | 0.1 | ||
| Squalene | 2803 | 0.4 | ||
| Total | 95.3 | 92.3 | 91.0 | |
Literature data were used to identify obscure constituents of the essential oil such as artedouglasia oxides A, C, and D and laciniata furanones E, F, and H [11, 12].
The cytotoxic activity of the essential oils from A. sublessingiana was studied using Artemia salina larvae and the literature method [13]. DMSO was used as the solvent. The antibiotic actinomycin D or staurosporine was used as a control. The experiments found that essential oil obtained from the aerial part at all concentrations exhibited cytotoxicity with lethality of larvae reaching 96%. Essential oil from seeds was cytotoxic at all concentrations with lethality of 75–96%. Essential oil from stems at concentrations of 10 and 5 mg/mL was cytotoxic with lethality of larvae reaching 96% while cytotoxicity was not found at a concentration of 1 mg/mL.
Antiradical activity was determined by the literature method [14, 15]. The tested essential oils showed low antioxidant activity as compared to the standard (butylhydroxyanisole) (Table 2).
Table 2.
Antiradical Activity of Essential Oils at Various Concentrations, %
| Sample | Concentration, mg/mL | ||||
|---|---|---|---|---|---|
| 0.1 | 0.25 | 0.5 | 0.75 | 1.0 | |
| Butylhydroxyanisole (BHA) | 80.82 ± 4.30 | 81.23 ± 2.22 | 82.30 ± 3.17 | 83.08 ± 2.33 | 83.88 ± 2.01 |
| A. sublessingiana (seeds) | 20.32 ± 2.03 | 20.18 ± 3.37 | 20.19 ± 2.32 | 22.45 ± 4.64 | 32.68 ± 3.08 |
| A. sublessingiana (stems) | 11.96 ± 3.27 | 11.99 ± 3.54 | 13.22 ± 3.68 | 14.31 ± 3.72 | 18.55 ± 3.19 |
| A. sublessingiana (aerial part) | 10.38 ± 4.17 | 10.08 ± 3.18 | 11.31 ± 3.69 | 11.98 ± 2.17 | 16.03 ± 2.04 |
Acknowledgment
The studies were financially supported by the Science Committee, Ministry of Education and Science, Republic of Kazakhstan (Grant No. AR13067774), Search for Biologically Active Compounds and Their Use in Agriculture; No. AR14869784, Isolation, Composition, and Biotesting of Essential Oil from Rare Plant Species of the Far East and Southern Kazakhstan; and Grant No. AR08051842, Composition and Biological Activity of Essential Oils from Plants of Central and Southeastern Asia. We thank Zh. B. Iskakova (Kazakh University of Technology and Business) for support and assistance with the biological activity studies and Prof. M. Yu. Ishmuratova (E. A. Buketov Karaganda University) for assistance with collection and identification of the plant raw material.
Footnotes
Translated from Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2022, pp. 646–648.
Contributor Information
E. M. Suleimen, Email: syerlan75@yandex.kz
Zh. A. Ibataev, Email: ZharkynAstana@gmail.com
R. N. Suleimen, Email: kasim_rai@mail.ru
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