Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2020, pp. 801–803.
The genus Ferula L. is distributed in Central Asia, the Mediterranean, and North Africa and numbers about 185 species [[
A literature review showed that extracts and essential oils from plants of the genus Ferula possessed antitumor, antioxidant, anthelminthic, antimicrobial, antiviral, and other activities [[
The species F. kelleri Koso-Pol. (=F. foliosa) was selected for the study. According to the literature, kellerin and foliferin were previously isolated from the subterranean part of this plant [[
The subterranean part of F. kelleri was collected during flowering in 2018 in Karasay District 5 km to the northeast of Ushkonyr, Zailii Alatau ridge, Ushkonyr gorge, Almaty Region (714 m above sea level, N 43°7′34.02″, E 76°30′41.33″). The species was determined by Dr. P. V. Veselova. A specimen is preserved in the herbarium of IRPH Phytochemistry (Karaganda, Kazakhstan).
Essential oils of F. kelleri were isolated by microwave extraction on an NEOS Essential Oils System (at atmospheric pressure 1.033 kgs/cm
Essential oils of F. kelleri obtained by the two methods were thin light-yellow liquids with a characteristic aroma. The total yields of essential oils were 1.3 (hydrodistillation) and 1.7% (microwave extraction) (calculated for air-dried raw material).
The oils were analyzed by GC-MS on a gas chromatograph with a GC-MSD Clarus-SQ 8 mass-selective detector under conditions analogous to those published [[
Essential oil of F. kelleri obtained by hydrodistillation contained 93 constituents of which 90 (95.7%) were identified. The major constituents (%) were α-bisabolol (29.2), α-pinene (16.0), β-phellandrene (7.8), β-pinene (4.4), p-cymene (4.2), 3-carene (3.7), and eremophilene (3.5). Essential oil from F. kelleri contained mainly monoterpenes (46.3%), sesquiterpenes (48.4), and small amounts of aromatic (0.5) and other (0.2) compounds (Table 1).
Constituent Composition of Essential Oil from Roots of Ferula kelleri Koso-Pol., %
Constituent RI HD MWE Constituent RI HD MWE Hexanal 797 0.1 1399 0.1 0.3 885 0.2 Aristolene 1402 0.2 0.2 919 0.3 Thymohydroquinone methyl ether 1408 0.2 0.3 928 16.0 2.3 1412 0.6 Camphene 938 0.2 Calarene 1413 0.4 Dehydrosabinene 942 0.2 Elemene 1416 0.1 3,7,7-Trimethyl-1,3,5-cycloheptatriene 959 0.1 1426 0.2 0.3 1430 0.5 967 4.4 1.2 Sesquisabinene 1440 0.1 0.2 6-Methyl-5-hepten-2-one 979 0.1 0.1 ( 1444 0.7 981 0.8 0.2 1450 0.1 Pseudolimonene 999 1.0 0.8 Dehydrosesquicineol 1454 0.6 0.9 3-Carene 1001 3.7 1456 0.3 1010 0.1 0.1 3,5,5,9-Tetramethyl-2,4a,5,6,9,9a-hexahydro-1H-benzo[a]cyclopentene 1457 0.5 1016 4.2 3.4 Limonene 1019 0.9 4,11,11-Trimethyl-8-methylenebicyclo [7.2.0]undec-4-ene 1461 0.3 1023 7.8 1030 0.7 Eremophilene 1463 3.5 1039 0.1 Alloaromadendrene 1466 0.1 0.3 1091 0.1 1473 0.1 6-Methyl-3,5-heptadien-2-one 1102 0.1 0.2 1477 0.6 1119 0.3 0.3 1478 0.1 Lemon ketone 1124 0.2 0.3 Cuparene 1483 0.2 0.2 Pinocarveol 1131 0.3 0.4 1486 0.1 1134 0.2 1.3 1489 0.5 0.3 1139 0.8 δ-Cadinene 1496 0.2 Unident. 1 1142 0.1 Myristicin 1499 0.1 0.2 2-Methyl-3-(1-methylethyl) 1149 0.1 1508 0.1 1514 0.9 0.8 Isocamphopinone 1150 0.1 1517 0.1 Unident. 2 1154 0.1 1525 1.4 1163 0.2 Germacrene B 1534 0.2 Naphthalene 1166 0.3 0.5 Elemicin 1538 0.5 0.7 1173 0.2 0.2 1544 0.1 0.1 Cryptone 1176 0.4 0.7 1550 0.2 0.2 1178 0.2 0.2 Spathulenol 1557 0.1 0.1 Myrtenal 1182 0.2 0.2 1562 0.1 0.3 Myrtenol 1185 0.2 0.2 Globulol 1567 0.1 Carveol 1194 0.2 1573 0.1 Verbenone 1197 0.3 0.6 1596 0.1 0.2 1209 0.1 0.2 1600 0.1 Isothymol methyl ether 1214 0.4 0.8 1604 0.2 0.2 Thymol methyl ether 1220 0.8 1.5 Methyl carvacrol 1229 0.7 1.1 δ-Cadinol 1613 0.1 Phellandral 1265 0.2 Unident. 3 1620 0.7 Cuminyl alcohol 1285 0.1 Cubenol 1621 0.3 1286 0.1 Unident. 4 1638 2.7 Thymol 1290 0.2 Himachalol 1639 1.5 0.3 Car-3-en-5-one 1303 0.5 1645 2.0 4.3 1335 0.1 0.2 Unident. 5 1659 0.3 0.4 Ylangene 1356 0.2 0.3 Cubenol 1665 0.2 1362 0.1 39.1 Pogostol 1666 0.2 1693 29.2 0.5 Unident. 8 1784 0.2 Unident. 6 1708 Unident. 9 1799 0.2 1710 0.3 Unident. 10 1851 0.3 Aromadendrene oxide-(1) 1727 0.1 Corymbolone 1864 0.8 Aristolone 1745 0.1 0.2 Unident. 11 1891 0.4 1752 0.1 0.2 Unident. 12 1907 0.5 Isovalencenol 1762 0.2 0.2 Farnesyl acetone 1913 0.5 1771 0.5 Total 95.7 78.2 Unident. 7 1779 0.6
HD, hydrodistillation; MWE, microwave extraction.
Essential oil obtained by microwave extraction contained 71 constituents of which 61 (78.2%) were identified. The major constituents were (%)α-bisabolol (39.1), α-bisabolol oxide B (4.3), p-cymene (3.4), and α-pinene (2.3). Sesquiterpenes dominated the identified constituents at 51.1% mass fraction. They also included monoterpenes (18.3%), esters (1.0), and aromatic compounds (0.9) (Table 1).
Thus, essential oils of F. kelleri were isolated for the first time by two methods (hydrodistillation in a Clevenger apparatus and microwave extraction). Their constituent compositions were studied. Essential oil from F. kelleri could be used as a source for isolating a quantitative yield of α-bisabolol, which has anti-inflammatory, antimicrobial, and antimalarial activity and low toxicity [[
Biological screening of essential oils from F. kelleri found that the essential oils isolated by the different methods possessed moderate to pronounced antimicrobial activity against test strains of Gram-positive bacteria S. aureus and B. subtilis, Gram-negative strain E. coli, and yeast-like fungus C. albicans and exhibited moderate anti-inflammatory activity in an acute exudative model.
Screening for toxicity used survival of Artemia salina marine shrimp larvae [[
The work was performed under Grant Project AR05130575 financed by the Science Committee, Ministry of Education and Science of the Republic of Kazakhstan. We thank Dr. R. B. Seidakhmetova, Head of the Pharmacology Laboratory, IRPH Phytochemistry, and Dr. Zh. B. Iskakova, Institute of Applied Chemistry, L. N. Gumilev ENU, for performing the biological screening of the essential oils.
By Zh. R. Shaimerdenova; A. I. Makubayeva; Ye. M. Suleimen and S. M. Adekenov
Reported by Author; Author; Author; Author