Chemical compositions, larvicidal and antimicrobial activities of <i>Zingiber castaneum</i> (Škorničk. &amp; Q.B. Nguyễn) and <i>Zingiber nitens</i> (M.F. Newman) essential oils

Huong, Le Thi; Huong, Trinh Thi; Bich, Nguyen Thi; Ogunwande, Isiaka Ajani

doi:10.1590/s2175-97902022e200204

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Brazilian Journal of Pharmaceutical Sciences

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Article • Braz. J. Pharm. Sci. 58 • 2022 • https://doi.org/10.1590/s2175-97902022e200204 copy

Chemical compositions, larvicidal and antimicrobial activities of Zingiber castaneum (Škorničk. & Q.B. Nguyễn) and Zingiber nitens (M.F. Newman) essential oils

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

In this paper, the chemical constituents, larvicidal and antimicrobial activities of hydrodistilled essential oils from Zingiber castaneum Škorničk. & Q.B. Nguyễn and Zingiber nitens M.F. Newman were reported. The main constituents of Z. castaneum leaf were bicyclogermacrene (24.8%), germacrene D (12.9%), cis-β-elemene (11.2%) and β-pinene (10.3%), while sabinene (22.9%) and camphene (21.2%) were the significant compounds in the rhizome. However, the dominant compounds in the leaf of Z. nitens includes β-pinene (45.8%) and α-pinene (10.7%). Terpinen-4-ol (77.9%) was the most abundant compound of the rhizome. Z. castaneum rhizome oil displayed larvicidal activity against Aedes aegypti and Culex quinquefasciatus with LC₅₀ values of 121.43 and 88.86 µg/mL, respectively, at 24 h. The leaf oil exhibited activity with LC₅₀ values of 39.30 µg/mL and 84.97 µg/mL, respectively. Also, the leaf and rhizome oils of Z. nitens displayed greater larvicidal action towards Ae. aegypti with LC₅₀ values of 17.58 µg/mL and 29.60 µg/mL, respectively. Only the rhizome oil displayed toxicity against Cx. quinquefasciatus with LC₅₀ value of 64.18 µg/mL. All the studied essential oils inhibited the growth of Pseudomonas aeruginosa ATCC25923 with minimum inhibitory concentration (MIC) value of 50.0 µg/mL. This paper provides information on the larvicidal and antimicrobial potentials of Z. castaneum and Z. nitens essential oils.

Keywords:
Aedes aegypti; Culex quinquefasciatus; Pseudomonas aeruginosa; β-Pinene; Terpinen-4-ol; Rhizomes

Peaks	Compoundsa	RI (Cal.)	RI (Lit.)	Z. castaneum		Z. nitens
				L	Rh	L	Rh
				Relative area %
1	Tricyclene	928	921	-	0.4	-	-
2	α-Thujene	930	926	-	0.5	-	-
3	α-Pinene	939	932	9.6	7.8	10.7	-
4	α-Fenchene	952	948	-	0.9	-	-
5	Camphene	955	952	0.5	21.2	0.1	-
6	Sabinene	979	972	1.7	22.9	1.6	1.1
7	β-Pinene	985	978	10.3	6.5	45.8	0.6
8	Myrcene	992	988	0.3	2.7	0.5	0.3
9	α-Phellandrene	1011	1009	-	0.3	-	-
10	δ-3-Carene	1016	1017	-	-	0.2	-
11	α-Terpinene	1022	1024	0.1	3.2	-	1.2
12	o-Cymene	1030	1030	0.2	1.0	-	1.4
13	Limonene	1034	1032	0.5	3.3	1.5	-
14	β-Phellandrene	1036	1034	-	0.4	0.2	0.2
15	1,8-Cineole	1038	1036	-	0.3	0.2	0.3
16	γ-Terpinene	1064	1062	0.2	5.5	0.2	4.6
17	cis-Sabinene hydrate	1074	1073	-	-	-	0.5
18	Terpinolene	1095	1094	0.1	0.5	-	0.8
19	trans-Sabinene hydrate	1106	1110	-	-	-	0.6
20	1-Octen-3-yl acetate	1110	1112	-	0.3	-	-
21	cis-p-Menth-2-el-1-ol	1130	1130	-	-	-	2.0
22	trans-p-Menth-2-el-1-ol	1148	1148	-	-	-	1.6
23	Borneol	1178	1177	-	-	-	-
24	Terpinen-4-ol	1187	1188	0.1	-	-	77.9
25	α-Terpineol	1200	1200	-	-	-	1.9
26	cis-Piperitol	1205	1207	-	-	-	0.6
27	trans-Piperitol	1217	1218	-	-	-	1.1
28	Fenchyl acetate	1228	1229	0.1	0.3	-	-
29	2-Decanal	1265	1264	-	0.2	-	-
30	Bornyl acetate	1294	1297	0.2	0.5	-	-
31	Bicycloelemene	1345	1343	0.5	-	-
32	δ-Elemene	1348	1350	6.5	5.4	0.4	-
33	α-Copaene	1390	1391	0.3	0.4	-	-
34	β-Bourbonene	1400	1401	-	-	0.2	-
35	cis-β-Elemene	1405	1407	11.2	9.8	2.8	-
36	cis-Thujopsene	1425	1422	-	-	0.1	-
37	β-Caryophyllene	1437	1437	0.4	1.7	1.2	-
38	γ-Elemene	1445	1445	0.4	0.8	-	-
39	allo-Aromadendrene	1457	1457	0.1	0.4	0.2	-
40	(Z)-β-Farnesene	1461	1465	-	-	0.5	-
41	α-Humulene	1472	1475	0.8	7.5	0.3	-
42	9-epi-(E)-Caryophyllene	1479	1480	2.2	2.0	1.2	-
43	β-Chamigrene	1490	1489	0.6	-	-
44	Valencene	1491	1491	0.4	-	0.5	-
45	ar-Curcumene	1493	1494	0.4	1.6	1.4	-
46	Germacrene D	1499	1500	12.9	9.2	4.7	-
47	Aristolochene	1502	1502	-	-	1.8	-
48	α-Zingiberene	1505	1506	1.1	4.6	6.4	-
49	γ-Amorphene	1510	1508	-	-	0.3	-
50	(E,E)-α-Farnesene	1513	1511	-	-	1.8	-
51	Bicyclogermacrene	1516	1517	24.8	15.8	7.0	-
52	β-Bisabolene	1518	1520	0.2	1.3	1.3	-
53	γ-Cadinene	1531	1530	0.3	0.3	0.2	-
54	β-Sesqui[hellandrene	1536	1535	0.2	1.1	2.6	-
55	δ-Cadinene	1538	1540	1.2	1.3	0.6	-
56	Elemol	1565	1563	-	0.2	-	-
57	(E)-Nerolidol	1571	1571	0.2	0.5	0.2	-
58	Germacrene B	1578	1580	1.3	1.6	-	-
59	Germacrene-D-4-ol	1595	1594	2.4	1.8	0.2	-
60	Spathulenol	1599	1600	1.2	2.0	0.7	-
61	Caryophyllene oxide	1605	1606	-	0.6	0.4	-
62	Viridiflorol	1606	1608	0.2	-	0.1	-
63	Guaiol	1615	1618	-	0.4	-	-
64	Zingiberenol	1624	1626	-	1.0	0.3	-
65	Ledol	1626	1628	0.3	-	-	-
66	Humulene epoxide II	1632	1632	-	0.6	-	-
67	α-Acorenol	1644	1644	-	0.3	0.1	-
68	Alismol	1648	1650	1.9	-	-	-
69	1-epi-Cubenol	1649	1652	-	3.2	-	-
70	Isospathulenol	1658	1660	-	-	0.1	-
71	epi-α-Cadinol	1660	1662	0.4	-	0.1	-
72	epi-α-Muurolol	1662	1664	0.4	1.1	0.2	-
73	α-Cadinol	1675	1676	0.8	1.6	0.5	-
74	α-Turmerone	1682	1680	0.4	2.9	0.5	-
75	Curlone	1716	1720	-	1.0	-	-
76	Phytol	2120	2119	-	-0.1		-
Total			96.8	94.1	98.9	96.7
Monoterpene hydrocarbons				23.5	10.1	59.0	10.2
Oxygenated monoterpenes				0.4	0.8	0.2	86.5
Sesquiterpene hydrocarbons				64.9	66.2	36.3	-
Oxygenated sesquiterpenes				8.0	16.5	3.3	-
Diterpenes				-	-	0.1	-
Non-terpenes				-	0.5	-	-

	Mortality (%)^{a, b}
	Concentration (µg/mL)
	12.5	25	50	100	150	200
Ae. Aegypti
Leaf
24 h	5.0 ±.816	15.0 ±.000	53.75 ± 3.304	100.0 ±.000	n.d	n.d
48 h	10.0 ±.816	22.5 ± 1.291	62.5 ± 2.517	100.0 ±.000	n.d	n.d
Rhizome
24 h	0	0	0	10.0 ±2.708	75.0 ±2.582	100.0±.000
48 h	0	0	13.7 ±1.708	15.0 ±2. 160	64.0 ±2.944	100.0 ±.000
Cx. quinquefasciatus
Leaf
24 h	0	0	13.75 ±.000	57.0 ±3.916	100.0 ±.000	n.d
48 h	0	10.0 ±.000	42.5 ± 2.646	84.3 ± 1.258	100.0 ±.000	n.d
Rhizome
24 h	0	0	3.70 ±.500	55.0 ±3.916	100.0 ±.000	n.d
48 h	0	10.0 ±1.000	42.5 ±2.6446	81.3 ±1.258	100.0 ±.000	n.d
	Minimum lethal concentration (µg/mL) ^c
	LC ₅₀	LC ₉₀	Regression equation	X ²	P
Ae. Aegypti
Leaf
24 h	39.30	89.94	$y = - 5.683 + 3.564 x$	8.472	0.000
48 h	31.78	80.37	$y = - 4.778 + 3.181 x$	9.943	0.000
Rhizome
24 h	121.43	145.28	$y = - 6.525 + 0.054 x$	9.512	0.000
48 h	110.31	125.33	$y = - 9.445 + 0.086 x$	2.497	0.000
Cx. quinquefasciatus
Leaf
24 h	84.97	141.45	$y = - 11.172 + 5.791 x$	7.458	0.000
48 h	47.40	92.29	$y = - 7.423 + 4.429 x$	6.914	0.000
Rhizome
24 h	88.86	117.68	$y = - 3.952 + 0.044 x$	8.502	0.000
48 h	48.08	72.13	$y = - 2.562 + 0.053 x$	6.871	0.000

	Mortality (%)^{a, b}
	Concentration (µg/mL)
	12.5	25	50	100
Ae. Aegypti
Leaf
24 h	12.5 ±.816	76.3 ±3.862	100.0 ±.000	100.0 ±.000
48 h	15.0 ±.957	82.5 ±3.317	100.0 ±.000	100.0 ±.000
Rhizome
24 h	0	17.5 ±1.291	83.7 ± 2.872	100.0 ±.000
48 h	5.0 ±.816	35.0 ±2.651	90.0 ± 2.309	100.0 ±.000
Cx. quinquefasciatus
Rhizome
24 h	0	6.3 ±.500	15.0 ±.000	92.5 ±1.291
48 h	0	6.3 ±.500	15.0 ±.000	92.5 ±1.291
	Minimum lethal concentration (µg/mL)c
	LC ₅₀	LC ₉₀	Regression equation	X ²	P
Ae. Aegypti
Leaf
24 h	17.58	23.25	$y = - 3.979 + 0.226 x$	9.343	0.000
48 h	15.12	18.70	$y = - 5.407 + 0.358 x$	2.095	0.036
Rhizome
24 h	29.60	37.60	$y = - 5.688 + 0.192 x$	2.012	0.044
48 h	26.32	36.92	$y = - 2.990 + 0.593 x$	5.938	0.000
Cx. quinquefasciatus
Rhizome
24 h	64.18	92.68	$y = - 2.887 + 0.045 x$	5.363	0.000
48 h	59.06	84.31	$y = - 2.998 + 0.051 x$	5.963	0.000

LC₅₀ 24 h^a
Plants	Origin	Ae. aegypti	Ae. albopictus	Cx. quinquefasciatus	References
Z. collinsii	Vietnam	-	25.51 μg/mL	50.11 μg/mL	*Huong et al., 2020b*Huong LT, Huong TT, Huong NTT, Hung NH, Dat PTT, Luong NX, et al. Mosquito larvicidal activities of the essential oil of Zingiber collinsii against Aedes albopictus and Culex quinquefasciatus. J Oleo Sci. 2020b;69(2):153-160.
Z. zerumbet	‘’	-	55.75 μg/mL	33.28 μg/mL	*Huong et al., 2019*Huong LT, Chinh HV, An NTG, Viet NT, Hung NH, Thuong NTH, et al. Antimicrobial activity, mosquito larvicidal activities and chemical compositions of the essential oils of Zingiber zerumbet in Vietnam. Eur J Med Pl. 2019;30(4):1-12.
‘’	Thailand	48.88 ppm	-	-	*Sutthanont et al., 2010*Sutthanont N, Wej C, Benjawan T, Anuluck J, Atchariya J, Udom C, et al. Chemical composition and larvicidal activity of edible plant-derived essential oils against the pyrethroid-susceptible and -resistant strains of Aedes aegypti (Diptera: Culicidae). J Vector Ecol. 2010;35(1):106-115.
‘’	Malaysia	102.6 μg/mL	-	-	*Jantan et al., 2003*Jantan I, Ping WO, Sheila DV, Ahmad NW. Larvicidal activity of the essential oils and methanol extracts of Malaysian plants on Aedes aegypti. Pharm Biol. 2003;41(4):234-236.
‘’	Malaysia	82.05 mg/L	106.5 mg/L	49.28 mg/L	Restu, Halijah and Awang, 2017Restu WM, Halijah INAH, Awang K. Efficacy of four species of Zingiberaceae extract against vectors of dengue, chikungunya and filariasis. Trop Biomed. 2017;34(2):375-387.
‘’	Thailand	-	-	50.78 ppm	Pushpanathan, Jebanesan and Govindarajan, 2008Pushpanathan T, Jebanesan A, Govindarajan M. The essential oil of Zingiber officinalis Linn (Zingiberaceae) as a mosquito larvicidal and repellent agent against the filarial vector Culex quinquefasciatus Say (Diptera: Culicidae). Parasitol Res . 2008;102(6):1289-1291.
Z. officinalis	Malaysia	197.2 µg/mL	-	-	*Jantan et al., 2003*Jantan I, Ping WO, Sheila DV, Ahmad NW. Larvicidal activity of the essential oils and methanol extracts of Malaysian plants on Aedes aegypti. Pharm Biol. 2003;41(4):234-236.
‘’	‘’	-	15.8%^a	21.8%^a	*Rabha et al., 2016*Rabha P, Gopalakrishna R, Baruah I, Singh L. Larvicidal activity of some essential oil hydrolates against dengue and filariasis vectors. E3 J Med Res. 2016;1(1):014-016.
‘’	India	40.5 mg/L	-	-	Kalaivani, Senthil-Nathan and Marugesan, 2012Kalaivani K, Senthil-Nathan S, Marugesan AG. Biological activity of selected Lamiaceae and Zingiberaceae plant essential oils against the dengue vector Aedes aegypti L. (Diptera: Culicidae). Parasitol Res . 2012;110(3):1261-1268.
‘’	Brazil	70.6 mg/mL	-	-	Dias, Morae, 2014Dias CN, Morae DFC. Essential oils and their compounds as Aedes aegypti L. (Diptera: Culicidae) larvicides: review. Parasitol Res . 2014;113(2):565-592.
Z. officinale
var. rubrum	Malaysia	120.60 mg/L	96.86 mg/L	130.50 mg/L	Restu, Halijah and Awang, 2017Restu WM, Halijah INAH, Awang K. Efficacy of four species of Zingiberaceae extract against vectors of dengue, chikungunya and filariasis. Trop Biomed. 2017;34(2):375-387.
Z. cernuum	India	44.88 μg/mL	55.84 μg/mL	48.44 μg/mL	*Rajeswary et al., 2018*Rajeswary M, Govindarajan M, Alharbi NS, Kadaikunnan S, Khaled JM, Benelli G. Zingiber cernuum (Zingiberaceae) essential oil as effective larvicide and oviposition deterrent on six mosquito vectors, with little non-target toxicity on four aquatic mosquito predators. Environ Sci Pollut Res. 2018:25(11):10307-10316.
Z. spectabile	Malaysia	155.93 mg/L	93.35 mg/L	107.78 mg/L	Restu, Halijah and Awang, 2017Restu WM, Halijah INAH, Awang K. Efficacy of four species of Zingiberaceae extract against vectors of dengue, chikungunya and filariasis. Trop Biomed. 2017;34(2):375-387.
Z. nimmonii	Thailand	44.46 μg/mL	-	48.26 μg/mL	*Govindarajan et al., 2016*Govindarajan M, Rajeswary M, Arivoli S, Tennyson S, Benelli G. Larvicidal and repellent potential of Zingiber nimmonii (J. Graham) Dalzell (Zingiberaceae) essential oil: an eco-friendly tool against malaria, dengue, and lymphatic filariasis mosquito vectors? Parasitol Res . 2016;115(5):1807-1816.
‘’	Malaysia	84.95 mg/L	99.04 mg/L	176.35 mg/L	Restu, Halijah and Awang, 2017Restu WM, Halijah INAH, Awang K. Efficacy of four species of Zingiberaceae extract against vectors of dengue, chikungunya and filariasis. Trop Biomed. 2017;34(2):375-387.
Z. castaneum Vietnam	-	49.85 μg/mL	-	*Huong et al., 2020a*Huong LT, Huong TT, Bich NT, Viet NT, Ogunwande IA. Larvicidal efficacy of essential oils from the rhizomes of Zingiber castaneum against Aedes albopictus. Am J Essent Oils Nat Prod. 2020a;8(2):23-26.
Z. montanum Vietnam	32.20 μg/mL	35.17 μg/mL	31.12 μg/mL	*Huong et al., 2020d*Huong LT, Huong TT, Huong NTT, Hung NH, Dat PTT, Luong NX, et al. Chemical composition and larvicidal activity of essential oils from Zingiber montanum against three mosquito vectors. Bol Latinoam Caribe Plant Med Aromat. 2020d;19(6):569-579.
Z. cornubracteatum	‘’	16.97 μg/mL	12.72 μg/mL	24.31 μg/mL	*Huong et al., 2020c*Huong LT, Chung NT, Huong TT, Sam LN, Hung NH, Ogunwande IA, et al. Essential oils of Zingiber species from Vietnam: chemical compositions and biological activities. Plants. 2020c;9(9):1269:34.
Z. neotruncatum	‘’	34.95 μg/mL	21.50 μg/mL	33.58 μg/mL	‘’
Z. nudicarpum ^b	‘’	19.30 μg/mL	22.33 μg/mL	12.44 μg/mL	‘’
Z. nudicarpum	‘’	23.44 μg/mL	28.05 μg/mL	11.50 μg/mL	‘’
Z. ottensii	‘’	38.16 μg/mL	19.79 μg/mL	27.19 μg/mL	‘’
Z. recurvatum	‘’	20.90 μg/mL	45.48 μg/mL	31.67 μg/mL	‘’

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[1] *Correspondence: L. T. Huong. School of Natural Science Education. Vinh University. 182 Le Duan, Vinh City, Nghệ An Province, Vietnam. E-mail: lehuong223@gmail.com. I. A. Ogunwande. Foresight Institute of Research and Translation. Ibadan, Nigeria. E-mail: isiakaogunwande@gmail.com.