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Constituent Composition and Cytotoxicity of Essential Oil from Chartolepis intermedia

Chartolepis intermedia Boiss. (Asteraceae), which is also called Centaurea chartolepis Greuter, is a perennial herbaceous plant that is broadly distributed in European Russia, Central Asia, Kazakhstan, and western Siberia [1].

C. intermedia is well studied. Grosshemin and cynaropicrin, which are of interest because of their biological activity [2-7], were identified in its aerial part [2].

Previously, the anatomical structure of this plant was investigated by us [8]. Herein, results from studies of the composition of C. intermedia essential oil and its cytotoxicity are reported.

The aerial part of C. intermedia (leaves, flowers, stems) was collected during flowering in the middle of August 2017 in a field near Korgalzhyn highway about 10 km from Astana. The collected raw material was dried and ground. Specimens are preserved in the herbarium of the Biological-Geographic Faculty, E. A. Buketov Karaganda State University, under code 1985.07.10.02.02.

Essential oil was obtained from ground dried plant matter (without rough stems) by steam distillation in a Clevenger apparatus for 2 h [9] using a hexane trap. GC-MS analysis of C. intermedia essential oil used conditions analogous to those reported before [10].

Table 1 shows that the main constituents of C. intermedia essential oil were β-caryophyllene oxide (5.0%), isospathulenol (4.6%), spathulenol (4.3%), n-hexadecanoic acid (3.9%), germacrene D (3.3%), 1,5-epoxysalvial-4(14)-ene (3.2%), heptacosane (2.7%), and phytol (2.6%).

Constituent Composition of Essential Oil from C. intermedia

Component	RII	%	Component	RII	%
1-Hexen-3-one	781	0.3	trans-2-(2-Pentenyl)furan	993	0.2
Hexanal	798	1.6	Octanal	998	0.2
cis-1,4-Dimethylcyclohexane	823	0.1	(E,E)-2,4-Heptadienal	1004	1.1
2,5,5-Trimethyl-1-hexen-3-yne	835	0.1	3-Cyclohexene-1-carboxaldehyde	1006	0.3
(E)-2-Hexenal	843	0.6	p-Cymene	1016	0.3
2-n-Butylfuran	878	0.1	Limonene	1021	0.3
(Z)-4-Heptenal	897	0.1	1,8-Cineol	1023	0.5
Heptanal	900	0.3	β-cis-Ocimene	1031	0.1
α-Pinene	926	0.4	Benzaldehyde	1034	0.2
Benzaldehyde	951	0.1	(E)-2-Octenal	1052	0.3
Sabinene	964	0.6	(E,E)-3,5-Octadien-2-one	1064	0.3
1-Octen-3-one	970	0.2	1-Octanol	1068	0.1
2-Pentylfuran	978	0.3	3,5-Octadien-2-one	1088	0.1
3-Pentylfuran	983	1.0	3-Thujanone	1100	0.3
(E,E)-2,4-Heptadienal	989	0.3	Nonanal	1103	0.5
1-Methyl-3-cyclohexene-1-carboxaldehyde	1106	0.2	2,2,4-Trimethyl-1,3-menandiol	1580	2.2
α-Thujone	1111	0.2	diisobutyrate
(E,Z)-2,6-Nonadienal	1145	0.2	2-Methylene-6,8,8-trimethyltricyclo-	1589	0.4
(E)-2-Nonenal	1152	0.2	[5.2.2.0(1,6)]undecan-3-ol
trans-Borneol	1159	0.1	Isoaromadendrene epoxide	1592	1.6
Safranal	1185	0.1	2,2,4-Trimethyl-1,3-pentanediol	1600	0.3
Decanal	1198	0.2	diisobutyrate
3-Propylidene-2-heptanone	1201	0.3	β-Copaen-4α-ol	1603	1.9
β-Cyclocitral	1205	0.4	13-nor-Eremophila-1(10)-en-11-one	1605	0.2
(Z)-2-Decenal	1255	0.1	Isospathulenol	1618	4.6
(E)-4-Decen-6-yne	1272	0.2	Unident.	1621	0.3
(E,E)-2,4-Decadienal	1289	0.2	(E)-α-Santalal	1625	0.2
Unident.	1312	1.0	τ -Cadinol	1631	0.2
δ-Elemene	1327	0.1	Aromadendrene oxide-(2)	1637	1.0
Cyclosativene	1357	0.4	Zizanol	1642	0.8
α-Ylangene	1359	0.1	Ledene oxide-(11)	1644	0.6
α-Copaene	1365	0.2	Unident.	1647	0.9
2-Butyl-2-octenal	1367	0.1	(Z,Z)-1,8,11-Heptadecatriene	1650	0.2
β-Damascenone	1370	0.8	Aromadendrene oxide-(1)	1662	1.1
β-Bourbonene	1372	0.1	(Z,Z,Z)-1,8,11,14-Heptadecatetraene	1666	0.3
cis-, trans-Nepetalactone	1375	0.2	1,7-Hexadecadiene	1672	1.1
Unident.	1378	0.6	Eudesma-4(15),7-dien-1β-ol	1675	0.5
1,2,3,4-Tetrahydro-2,5,8-trimethyl-1-naphthalenol	1381	0.4	ent-Germacra-4(15),5,10(14)-trien-1β-ol	1681	2.5
4-(2,2-Dimethyl-6-methylenecyclohexyl)-2-butanone	1384	0.1	Unident.	1699	0.4
(E)-5-Tetradecene	1391	0.2	Aromadendran-4,10-diol	1706	0.3
Tetradecane	1400	0.1	6-Isopropenyl-4,8a-dimethyl-1,2,3,5,	1711	0.2
Unident.	1402	1.4	6,7,8,8a-octahydronaphthalen-2-ol
Caryophyllene	1405	1.0	Pentadecanal	1719	0.4
α-Ionone	1412	0.1	Ylangenal	1728	0.1
γ -Elemene	1419	0.1	(S,Z)-2-Methyl-6-(p-tolyl)hept-2-en-1-ol	1741	0.1
6-Methyl-6-(5-methylfuran-2-yl)heptan-2-one	1431	0.1	Ylangenol	1747	0.2
Humulene	1438	0.3	Unident.	1753	0.4
Dihydropseudoionone	1439	1.1	10-Peroxymuurolan-3,9(11)-diene	1760	0.5
(E)-β-Farnesene	1445	0.3	Tetradecanoic acid	1772	0.4
β-Guaiene	1456	0.1	Saussurea lactone	1819	0.1
Germacrene D	1462	3.3	6,10,14-Trimethyl-2-pentadecanone	1847	0.6
Epoxy-β-ionone	1465	0.1	Phthalic acid hept-3-yl isobutyl ester	1856	0.1
β-Eudesmene	1468	1.6	Z-10-Pentadecen-1-ol	1885	0.2
Bicyclogermacrene	1475	0.6	Farnesyl acetone	1909	0.5
α-Muurolene	1480	0.2	Methyl-4,7,10,13-hexadecatetraenoate	1912	0.1
1-Pentadecene	1484	0.4	n-Hexadecanoic acid	1971	3.9
α-Himachalene	1491	0.7	Heneicosane	2102	0.3
Unident.	1497	1.2	Phytol	2106	2.6
Eremophila-1(10),8,11-triene	1503	0.1	(Z,Z)-9,12-Octadecadienoic acid	2132	0.3
Unident.	1509	0.4	Docosane	2199	0.1
Cadala-1(10),3,8-triene	1519	0.3	Tricosane	2341	0.9
Ledene	1528	0.5	Tetracosane	2400	0.2
cis-Hexahydro-8a-methyl-1,8(2H,5H)naphthalenedione	1537	1.3	Pentacosane	2509	1.0
Pentanoic acid octyl ester	1541	0.4	Diisooctyl phthalate	2532	0.2
1,5-Epoxysalvial-4(14)-ene	1546	1.0	Hexacosane	2597	0.1
Unident.	1552	0.5	Heptacosane	2694	2.7
Spathulenol	1559	4.3	Octacosane	2798	0.2
β-Caryophyllene oxide	1563	5.0	Nonacosane	2890	1.7
Unident.	1569	0.4	Hentriacontane	3087	0.1
1,5-Epoxysalvial-4(14)-ene	1574	3.2	Total		86.7

The cytotoxicity of C. intermedia essential oil was determined using the usual method of survival of Artemia salina shrimp [11]. The experiments found that C. intermedia essential oil at all tested concentrations (10, 5, and 1 mg/mL) exhibited acute lethal toxicity (96%), i.e., all larvae died.

Translated from Khimiya Prirodnykh Soedinenii, No. 6, November-December, 2018, pp. 1000-1001.

References References 1 Flora of Kazakhstan [in Russian], Vol. 9, Nauka, Alma-Ata, 1966, 450 pp. 2 A. Q. Ashton, Sesquiterpenes, in:, Terpenes - Advances in Research and Application, Chap. 5, Scholarly Editions, Atlanta, 2013, pp. 265-335. 3 M. Bruno, S. Bancheva, S. Rosselli, and A. Maggio, Phytochemistry, 95, 19 (2013). 4 J. Y. Cho, A. R. Kim, H. G. Joo, B. H. Kim, M. H. Rhee, E. S. Yoo, D. R. Katz, B. M. Chain, and J. H. Jung, Biochem. Biophys. Res. Commun., 313, 954 (2004). 5 J. Y. Cho, K. U. Baik, J. H. Jung, and M. H. Park, Eur. J. Pharmacol., 398, 399 (2000). 6 M. F. Elsebai, A. Mocan, and A. G. Atanasov, Front. Pharmacol., 7, 472 (2016). 7 T. Grothe, E. Roemer, and P. Wabnitz, WO2011085979 A1M, Jul. 21, 2011. 8 M. Yu. Ishmuratova, E. M. Suleimen, and G. G. Sisengalieva, in:, Proceedings of the 1st International Scientific-Practical Conference "Natural Sciences and Medicine: Theory and Practice" [in Russian], SibAK, Novosibirk, No. 1 (1), 2018, pp. 6-13. 9 State Pharmacopoeia of the USSR, No. 2, General Methods of Analysis. Medicinal Plant Raw Material of the USSR Ministry of Health [in Russian], 11th Ed., Moscow, 1990, 400 pp. M. A. Zhunusova, E. M. Suleimen, Zh. B. Iskakova, M. Yu. Ishmuratova, and R. M. Abdullabekova, Chem. Nat. Compd., 53, 775 (2017). E. M. Suleimenov, Chem. Nat. Compd., 45, 710 (2009).

By E. M. Suleimen; G. G. Sisengalieva; R. I. Dzhalmakhanbetova; Zh. B. Iskakova and M. Yu. Ishmuratova

Titel:	Constituent Composition and Cytotoxicity of Essential Oil from Chartolepis intermedia
Autor/in / Beteiligte Person:	M. Yu. Ishmuratova ; Iskakova, Zh. B. ; Suleimen, E. M. ; Dzhalmakhanbetova, R. I. ; Sisengalieva, G. G.
Link:	Volltext (PDF) View record at OpenAIRE (Volltext) https://doi.org/10.1007/s10600-018-2587-5
Zeitschrift:	Chemistry of Natural Compounds, Jg. 54 (2018-11-01), S. 1177-1179
Veröffentlichung:	Springer Science and Business Media LLC, 2018
Medientyp:	unknown
ISSN:	1573-8388 (print) ; 0009-3130 (print)
DOI:	10.1007/s10600-018-2587-5
Schlagwort:	010405 organic chemistry Chemistry Plant Science General Chemistry 01 natural sciences General Biochemistry, Genetics and Molecular Biology 0104 chemical sciences law.invention 010404 medicinal & biomolecular chemistry law Composition (visual arts) Food science Intermedia Cytotoxicity Essential oil
Sonstiges:	Nachgewiesen in: OpenAIRE Rights: CLOSED

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