Phytochemical Analysis, Antioxidant and Antifungal Activity of Essential oil and Extracts of <i>Alpinia malaccensis</i> (Burm.f.) Roscoe flowers

Sethi, Sonali; Prakash, Om; Kumar, Ravendra; Dubey, Shiv Kumar; Arya, Mamta; Pant, Anil Kumar

doi:10.1590/s2175-97902022e201209

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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/s2175-97902022e201209 copy

Phytochemical Analysis, Antioxidant and Antifungal Activity of Essential oil and Extracts of Alpinia malaccensis (Burm.f.) Roscoe flowers

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

The present study describes chemical composition, phytochemicals, antifungal activities, antioxidant assays and total phenolic content of essential oil and varied polarity solvent extract from flowers of Alpinia malaccensis (Burm.f.). Total 27 components were identified in essential oil by GC-MS with terpinen-4-ol (28.6%) and α- terpineol (12.8%) as the main constituent. The essential oil was found to have maximal levels of phenolic content (64.60 μg/mL) as compared to the other extracts. The antioxidant assay evaluated in extracts and essential oil by different methods revealed good-to-moderate antioxidant potential with different IC⁵⁰ values viz. (188.02 -250.25 μg/mL) in Fe³⁺ reducing power, (153.15-201.59 μg/mL) in Fe²⁺ metal-chelating ability, (130.39-181.12 μg/mL) in DPPH, (88.29-187.32 μg/mL) in OH radical, (79.04-156.79 μg/mL), in NO radical and (138.72-233.00 μg/mL) in superoxide anion scavenging activities, respectively. The methanolic extract display remarkable fungicidal activity against the tested pathogens followed by dichloromethane extract, essential oil, hexane extract and petroleum ether extract respectively, with MIC values ranging from 31.25 to 500 μg/mL. Based on results, it can be inferred that the flower of A. malaccensis if explored further for its medicinal properties, might be a good source to develop a safe and sustainable natural food preservative.

Keywords:
Alpinia malaccensis; Antifungal activity; Antioxidant activity; Flower; Total phenol

Phytoconstituent	AMFPE	AMFHE	AMFDE	AMFME
Alkaloids	+	+	+	+
Carbohydrates	-	-	+	+
Glycosides	+	+	+	+
Saponins	+	+	+	+
Phytosterols	-	+	+	+
Fats & Oils	+	+	+	+
Resins	-	-	-	-
Phenols	+	+	+	+
Tannins	+	+	+	+
Flavonoids	-	+	-	+
Diterpenes	-	-	+	-

SN	Compound Name	KI	%Conc.	Mol. formula	Method of identification Major fragments
1	Linalool	1095	0.5	C₁₀H1₈O	M⁺ 154, M/z:, 71,43,41
2	cis-β-terpineol	1140	0.8	C₁₀H₁₈O	M⁺ 154, M/z:, 43,71,41
3	Camphor	1146	0.6	C₁₀H₁6O	M⁺ 152, M/z:, 95,41,81
4	terpinen-4-ol (1)	1168	28.6	C ₁₀ H ₁₈ O	M⁺ 154, M/z:, 71,93,111
5	α-terpineol (2)	1188	12.8	C ₁₀ H ₁₈ O	M⁺ 154, M/z:, 59,43,93
6	linalyl formate	1200	0.3	C₁₁ H₁₈ O₂	M⁺ 182, M/z:, 93,41,43
7	cis- piperitol (3)	1203	1.0	C₁₀ H₁₈ O	M⁺ 154, M/z:, 84,83,41
8	β.-citronellol	1225	0.1	C₁₀H₂₀O	M⁺ 154, M/z:, 41,69,55
9	Methylheptenone	1303	0.2	C₈H1₄O	M⁺ 126, M/z:, 43,41,69
10	Z- methyl -cinnamate	1299	0.3	C₁₀ H₁₀ O₂	M⁺ 162, M/z:, 131,103,77
11	α.-copaene	1376	0.5	C15H24	M⁺ 154, M/z:, 204,119,41
12	E- methyl- cinnamate (4)	1378	12.4	C ₁₀ H ₁₀ O ₂	M⁺ 154, M/z:, 162,103,77
13	β.-caryophyllen (5)	1408	2.3	C₁₅H₂₄	M⁺ 204, M/z:, 41,69,93
14	trans- linaloloxide (6)	1409	1.9	C₁₀H₁₈O2	M⁺ 170, M/z:, 41,82,69
15	α-caryophyllene (7)	1419	1.9	C₁₅H₂₄	M⁺ 204, M/z:, 93,80,41
16	E -ethyl-cinnamate	1467	0.1	C₁₁ H₁₂ O₂	M⁺ 176, M/z:, 131,103,77
17	α.-muurolene	1500	0.1	C₁₅H₂₄	M⁺ 204, M/z:, 105,41,91
18	cis-calamenene	1529	0.5	C₁₅H₂₂	M⁺ 202, M/z:, 159,41,131
19	E -nerolidol (8)	1563	1.7	C₁₅H₂₆O	M⁺ 222, M/z:, 69,41,43
20	α-caryophyllene oxide (9)	1580	5.3	C ₁₅ H ₂₄ O	M⁺ 220, M/z:, 43,41,79
21	humuladienone (10)	1580	3.1	C₁₅H₂₄O	M⁺ 220, M/z:, 43,41,67
22	α-cadinol (11)	1654	1.6	C₁₅ H₂₆ O	M⁺ 222, M/z:, 43,41,85
23	farnesol	1698	0.5	C₁₅ H₂₆ O	M⁺ 222, M/z:, 69,41,81
24	octadecane (12)	1800	6.9	C ₁₈ H ₃₈	M⁺ 254, M/z:, 57,43,71
25	palmitinic acid (13)	1960	2.1	C₁₆H₃₂O₂	M⁺ 256, M/z:, 43,60,73
26	docosane (14)	2200	4.5	C₂₂H₄₆	M⁺ 310, M/z:, 57,43,71
27	tetracosane (15)	2400	1.0	C₂₄H₅₀	M⁺ 338, M/z:, 57,43,71
	Total		91.6

Sample / Standard	Antioxidant assay
Sample / Standard	DPPH Scavenging activity/IC₅₀(µg/ml)	.OH scavenging activity/IC₅₀ (µg/ml)	Nitric oxide radical scavenging activity/IC₅₀(µg/ml)	Superoxide anion scavenging activity/IC₅₀(µg/ml)	Reducing power ability/RP₅₀(µg/ml)	Metal chelating ability/IC₅₀(µg/ml)	Total phenols(µg/ml)
AMFPE	181.12±1.3 ^h	187.32±1.3^f	156.79±0.0^f	233.00±0.4^f	250.25±0.8ⁱ	201.59±2.9^f	15.03±0.2^a
AMFHE	169.47±2.1^g	164.45±0.6^e	130.38±1.1^e	214.83±1.1^e	221.00±0.9^h	184.79±2.6^e	33.09±0.1^b
AMFDE	154.09±1.1^f	142.81±1.2^d	114.61±0.7^d	206.98±2.3^d	202.24±0.4^g	177.17±2.0^d	46.66±0.2^c
AMFME	138.20±1.7^e	88.29±2.0^b	79.04±1.5^b	166.51±4.4^c	188.02±0.1^e	156.88±3.0^c	51.75±0.2^d
AMFEO	130.39±0.196^d	102.25±0.5^c	83.87±0.5^c	138.72±0.4^b	190.71±0.9^f	153.15±0.4^c	64.60±0.1^e
BHT	33.81±0.4^a	-	-	-	117.88±0.3^b	-	-
CATECHIN	42.99±2.7^b	-	-	-	143.91±0.6^c	-	-
GALLIC ACID	49.27±1.1^c	-	-	-	151.47±0.6^d	-	-
ASCORBIC ACID	32.46±0.2^a	44.36±4.5^a	62.03±0.3^a	32.28±1.1^a	115.63±0.2^a	-	-
EDTA	-	-	-	-	-	47.72±2.3^a	-
CITRIC ACID	-	-	-	-	-	61.76±0.3^b	-

Phenols	Correlation coefficient (R)
	Total phenols	IC₅₀(µg/ml)				RP₅₀(µg/ml)
	Total phenols	DPPH Scavenging	OH scavenging	Nitric oxide radical scavenging activity/	Super oxide anion scavenging activity	Metal chelating ability	Reducing power ability
Total phenols	01	-0.975^**	-0.901^*	-0.942^*	-0.924^*	-0.959*	-0.963^*

Extracts	Concentration (μg/ml)	Antifungal activities (% of inhibition) (MIC)
Extracts	Concentration (μg/ml)	C. falcatum	R.solani	S. sclerotium	S. rolfsii
AMFPE	250	0±0^a	2.5±1.4^a	0±0^a	0±0^a
	500	5±1.4^ab	3.33±2.2^a	34.16±3.0^b	6.66±2.2^a
	750	29.16±2.2^d(500)	32.5±1.4^c(250)	78.33±1.6^e(500)	42.5±1.4^c(500)
	1000	61.66±0.8^f	44.16±1.6^d	86.66±0.8^fg	79.16±0.8^e
AMFHE	250	0±0^a	3.33±2.2^a	0±0^a	5±1.4^a
	500	10±2.5^bc(500)	20.83±0.8^b(250)	42.5±1.4^cd(500)	41.66±3.0^c(250)
	750	49.16±0.8^e	45±2.5^d	83.33±2.2^ef	46.66±2.2^cd
	1000	100±0^g	100±0^g	93.33±0.8^gh	81.66±0.8^ef
AMFDE	250	5±2.5^ab	31.66±1.6^c	40.83±2.2^bc	43.33±2.2^c
	500	43.33±1.6^e(250)	45±1.4^d(250)	87.5±1.4^fg(125)	55±1.4^d(125)
	750	60.83±0.8^f	59.16±0.8^e	91.66±0.8^g	86.66±0.8^ef
	1000	100±0^g	100±0^g	100±0^h	100±0^g
AMFME	250	21.66±1.6^d	48.33±0.8^d	90.83±0.8^fg	55±1.4^d
	500	47.5±2.5^e(250)	69.16±1.6^f(125)	93.33±1.6^gh(31.25)	90.83±3.0^g(62.5)
	750	65.83±2.2^f	100±0^g	100±0^h	100±0^g
	1000	100±0^g	100±0^g	100±0^h	100±0^g
AMFEO	250	0±0^a	1.66±1.6^a	49.16±1.6^d	0±0^a
	500	13.33±1.6^c(500)	5±1.4^a(250)	90±2.8^fg(125)	5±1.4^a(500)
	750	46.66±0.8^e	41.66±0.8^d	91.66±0.8^g	23.33±3.3^b
	1000	100±0^g	100±0^g	100±0^h	46.66±2.2^cd

Universidade de São Paulo, Faculdade de Ciências Farmacêuticas Av. Prof. Lineu Prestes, n. 580, 05508-000 S. Paulo/SP Brasil, Tel.: (55 11) 3091-3824 - São Paulo - SP - Brazil
E-mail: bjps@usp.br

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[1] *Correspondence: O. Prakash. Department of Chemistry. College of Basic Sciences and Humanities. G.B. Pant University of Agriculture and Technology, Pantnagar. U.S. Nagar-263 145, Uttarakhand, India. Email: oporgchem@gmail.com.