Fumigant toxicity and biochemical properties of (α + β) thujone and 1, 8-cineole derived from <i>Seriphidium brevifolium</i> volatile oil against the red imported fire ant <i>Solenopsis invicta</i> (Hymenoptera: Formicidae)

Xie, Feng; Rizvi, Syed Arif Husain; Zeng, Xinnian

doi:10.1016/j.bjp.2019.04.013

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Original articles • Rev. bras. farmacogn. 29 (6) • Nov-Dec 2019 • https://doi.org/10.1016/j.bjp.2019.04.013 copy

Fumigant toxicity and biochemical properties of (α + β) thujone and 1, 8-cineole derived from Seriphidium brevifolium volatile oil against the red imported fire ant Solenopsis invicta (Hymenoptera: Formicidae)

Authorship SCIMAGO INSTITUTIONS RANKINGS

ABSTRACT

The excessive use of chemical insecticides has led to negative effects on human health and the environment. Volatile oils are one of the possible potential alternatives to chemical insecticides. Traditionally Seriphidium brevifolium (Wall. ex DC.) Ling & Y.R.Ling, Asteraceae, powder from its leaves is used to treat gastric problems and expel intestinal worms by local peoples, but yet there is no literature available regarding its insecticidal activity. In this study fumigant toxicity and enzyme inhibition activities of the S. brevifolium volatile oil collected from the highlands of Skardu Baltistan, Pakistan, was evaluated against the red imported fire ant Solenopsis invicta. The phytochemical studies indicated that monoterpenes were the most abundant constituents, accounting for 88% of the total oil. The major dominant constituents were 2-bornanone (28.2%), 1,8-cineole (19.9%), α-thujone (7.5%), β-thujone (6.7%) which accounts for 62.3% of total constituents identified, with volatile oil yield of 4.11% (w/w). The fumigation assay indicated that the volatile oil was acutely toxic to fire ants, with an LC₅₀ of 16.47 µl/l. Among the constituents tested, only (α + β) thujone and 1,8-cineole were toxic, with LC₅₀ of 17.68 and 30.66 µl/ after 12 h of exposure. The volatile oil, (α + β) thujone and 1, 8-cineole showed strong fumigant activity against the red imported fire ant workers in a time- and dose-dependent manner. The volatile oil caused 100% mortality of the red imported fire ant workers, even at the lowest concentration of 20 µl/l after 24 h of exposure. In addition, the volatile oil and 1,8-cineole inhibited acetylcholinesterase activity, while (α + β) thujone inhibited carboxylesterase activity in the fire ant workers. It has been concluded that the volatile oil and some of the compounds from S. brevifolium might be developed as eco-friendly approaches for the control of red imported fire ants.

Keywords:
Botanical pesticides; Short-leaved wormwood; Fire ants; Fumigant toxicity; Volatile oil; Biochemical activities

PK	Library/ID^a a Compounds are listed in order of their elution from a HP-5MS column.	KI[Exp]^b b KI(Exp) retention indices (Kovats) relative to C7-C40 n-alkanes on a HP-5MS column.	KI[Lit]^c c KI(Lit) retention indices of reference compounds from literature (Bertella et al., 2018; Bossou et al., 2013; Cheng et al., 2008; Goodner, 2008; Herrera et al., 2014; Joshi, 2013; Nezhadali et al., 2008; Rajeswara Rao et al., 2014; Sonboli et al., 2013; Vieira et al., 2017).	Area %	ID^d d ID = Identification methods; MS = comparison of the mass spectrum with those of the computer mass libraries, and in Adams or NIST 08.
1	α-Thujene	928	919	1.5	MS,RI
2	α-Pinene	934	926	1.9	MS,RI
3	Camphene	949	955	1.8	MS,RI
4	Sabinene	975	978	0.7	MS
5	β-Myrcene	995	999	1.2	MS,RI
6	δ-3-Carene	1016	1023	0.8	MS
7	p-Cymene	1026	1027	2.9	MS,RI
8	Limonene	1030	1030	1.9	MS,RI
9	β-Phellandrene	1032	1034	1.7	MS,RI
10	1,8-Cineole	1036	1037	19.9	MS,RI
11	(Z)-β-ocimene	1040	1043	0.8	MS,RI
12	γ-Terpinene	1054	1052	0.9	MS,RI
13	Linalool	1094	1094	0.8	MS,RI
14	α-Thujone	1109	1109	7.5	MS,RI
15	β -Thujone	1119	1122	6.7	MS,RI
16	Trans-p-Menth-2-en-1-ol	1144	1144	2.0	MS,RI
17	2-Bornanone	1160	1164	28.2	MS,RI
18	Terpinen-4-ol	1174	1170	0.9	MS,RI
19	Myrtenol	1200	1203	1.0	MS,RI
20	Carvone	1239	1229	2.9	MS,RI
21	Thymol	1292	1286	1.6	MS,RI
22	n-Tridecane	1300	1307	3.0	MS,RI
23	β-Elemene	1395	1389	2.0	MS,RI
24	Isocaryophyllene	1407	1409	3.0	MS
25	β-Caryophyllene	1431	1421	2.0	MS,RI
26	α-Humulene	1450	1455	2.5	MS,RI
	Monoterpenes			88.0
	Sesquiterpenes			9.0
	Others			3.0
	Total			99.9

^a
Compounds are listed in order of their elution from a HP-5MS column.
^b
KI(Exp) retention indices (Kovats) relative to C₇-C₄₀ n-alkanes on a HP-5MS column.
^c
KI(Lit) retention indices of reference compounds from literature (Bertella et al., 2018Bertella, A., Benlahcen, K., Abouamama, S., Pinto, D.C., Maamar, K., Kihal, M., Silva, A.M., 2018. Artemisia herba-alba Asso. Essential oil antibacterial activity and acute toxicity. Ind. Crop. Prod. 116, 137-143.; Bossou et al., 2013Bossou, A.D., Mangelinckx, S., Yedomonhan, H., Boko, P.M., Akogbeto, M.C., De Kimpe, N., Avlessi, F., Sohounhloue, D.C., 2013. Chemical composition and insecticidal activity of plant essential oils from Benin against Anopheles gambiae (Giles). Parasit. Vectors 6, http://dx.doi.org/10.1186/1756-3305-6-337
http://dx.doi.org/10.1186/1756-3305-6-33... ; Cheng et al., 2008Cheng, S.-S., Liu, J.-Y., Lin, C.-Y., Hsui, Y.-R., Lu, M.-C., Wu, W.-J., Chang, S.-T., 2008. Terminating red imported fire ants using Cinnamomum osmophloeum leaf essential oil. Bioresour. Technol. Rep. 99, 889-893.; Goodner, 2008Goodner, K., 2008. Practical retention index models of OV-101, DB-1, DB-5, and DB-Wax for flavor and fragrance compounds. LWT-Food Sci. Technol. 41, 951-958.; Herrera et al., 2014Herrera, J.M., Zunino, M.P., Massuh, Y., Pizzollito, R., Dambolena, J.S., Gañan, N.A., Zygadlo, J.A., 2014. Fumigant toxicity of five essential oils rich in ketones against Sitophilus zeamais (Motschulsky). Agriscientia 31, 35-41.; Joshi, 2013Joshi, R.K., 2013. Volatile composition and antimicrobial activity of the essential oil of Artemisia absinthium growing in Western Ghats region of North West Karnataka, India. Pharm. Biol. 51, 888-892.; Nezhadali et al., 2008Nezhadali, A., Akbarpour, M., Shirvan, B.Z., 2008. Chemical composition of the essential oil from the aerial parts of Artemisia herba. J. Chem. 5, 557-561.; Rajeswara Rao et al., 2014Rajeswara Rao, B., Syamasundar, K., Patel, R., 2014. Effect of method of distillation on the yield and chemical composition of Artemisia annua essential oil. J. Essent. Oil Res. 26, 486-491.; Sonboli et al., 2013Sonboli, A., Bahadori, M.B., Dehghan, H., Aarabi, L., Savehdroudi, P., Nekuei, M., Pournaghi, N., Mirzania, F., 2013. Chemotaxonomic importance of the essential oil composition in two subspecies of Teucrium stocksianum Boiss. From Iran. Chem. Biodivers. 10, 687-694.; Vieira et al., 2017Vieira, T.M., Dias, H.J., Medeiros, T.C., Grundmann, C.O., Groppo, M., Heleno, V.C., Martins, C.H., Cunha, W.R., Crotti, A.E., Silva, E.O., 2017. Chemical composition and antimicrobial activity of the essential oil of Artemisia absinthium Asteraceae leaves. J. Essent. Oil Bear. Pl. 20, 123-131.).
^d
ID = Identification methods; MS = comparison of the mass spectrum with those of the computer mass libraries, and in Adams or NIST 08.

Treatments	Concentration (µl/l)	Mortality (%) ± SD^a a Values are mean ± SD of five replicates.	N^b b Total number of fire ant workers treated.	LC50 (µl/l) (95% LCL-UCL)^c c LC50: lethal concentrations (µ-/l).	LC90 (µl/l) (95% LCL-UCL)^d d LC90: lethal concentrations (µl/l).	Slope ± SE	X², (d.f) ^e e χ2 chi square, d.f. degrees of freedom.	p-Value
SBEO	0	1.9 ± 4.77	942	16.472 (12.23 - 26.57)	74.52(39.84-245.22)	1.95 ± 0.19	3.8(3)	0.21n.s^f f n.s. = not significant (p > 0.05).
	4	16.4 ± 1.34
	12	31.30 ± 1.23
	20	52.23 ± 1.04
	28	65.44 ± 0.97
	40	85.43 ± 0.56
(α + β) Thujone	0	2.56 ± 3.23	949	17.68 (10.71-29.59)	89.03(44.92-268.19)	1.82 ± 0.17	4.4(3)	0.32 n.s
	4	16.49 ± 2.23
	12	30.33 ± 1.98
	20	51.23 ± 1.31
	28	60.44 ± 1.11
	40	82.43 ± 0.56
1,8-Cineole	0	3.46 ± 3.71	935	30.66 (26.281-33.037)	103.03(82.33-143.22)	2.44 ± 0.23	4.5(3)	0.67 n.s
	12	15.46 ± 3.36
	20	30.22 ± 2.34
	28	49.23 ± 2.11
	40	63.44 ± 1.56
	80	83.24 ± 0.87
Dichlorvos (ng/l)^h h Dichlorvos was used as positive control (ng/l).	0	1.46 ± 3.43	867	96.776 (77.38-121.13)	1018.55(667.29-1244.12)	1.25 ± 0.11	4.44(3)	0.21 n.s
	10	14.33 ± 2.36
	50	29.33 ± 2.43
	100	51.53 ± 1.43
	200	62.88 ± 1.03
	500	85.26 ± 0.51
(R)- (+)- Limonene		NA^g g No activity was observed against fire ant workers during fumigation assay.
Limonene		NA
Thymol		NA
2-Bornanone		NA

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[1] * Corresponding author. E-mail:zengxn@scau.edu.cn (X. Zeng).