The chemical composition and antibacterial activity of a methanolic extract of <i>Satureja khuzistanica</i>

Davoodi, Mansooreh; Nejad-Ebrahimi, Samad; Rustaiyan, Abdolhossein; Esmaeili, Davoud

doi:10.1590/s2175-97902022e19233

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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/s2175-97902022e19233 copy

The chemical composition and antibacterial activity of a methanolic extract of Satureja khuzistanica

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

In the present study, the metabolite profiling of methanolic extract from aerial parts of Satureja khuzistanica Jamzad, as an endemic medicinal plant from Iran, was evaluated using HPLC-PDA-ESI. Then, the main compound from the extract was isolated and purified by using extensive chromatographic techniques. In addition, the structure of the isolated compounds was elucidated using 1D, 2D NMR, and MS spectrometry, upon which 22 compounds were identified. The antibacterial activity of diosmetin 7-rutinoside (6) and linarin (13) in combination with carvacrol as a major compound of the essential oil was tested against Pseudomonas aeruginosa and Staphylococcus aureus through disc diffusion and minimum inhibitory concentration methods. The results indicated that the linarin, when mixed with carvacrol as the main compounds in the essential oil of the plant, has a satisfactory activity against both Pseudomonas aeruginosa and Staphylococcus aureus with MIC values of 0.16 and 0.18 µg/mL, respectively. Further, the fractional inhibitory concentration (FIC) index indicated that this compound had synergism with carvacrol.

Keywords:
Lamiaceae; Caffeic acid; Flavonoid; HPLC-PDA-MS profiling; Pseudomonas aeruginosa; Staphylococcus aureus

No	t_R(min)	Compound	UV-vis λ_max (nm)	m/z positive	m/z negative	Identification Method	References
1	1.9	erigeroside	233, 261	[M+Na]⁺ 297, [M+K]⁺ 313 [2M+Na]⁺ 571	-	MS-UV, NMR	(Tafazzoli, Ghiasi, Moridi, 2008Tafazzoli M, Ghiasi M, Moridi M. Dynamic stereochemistry of erigeroside by measurement of 1H-1H and 13C-1H coupling constants. Spectrochim Acta Part A. 2008;70(2):350-7.)
2	7.9	apigenin-7-Ogentiobioside	269, 328	[M+H]⁺ 595	[M-H]- 593	MS-UV	(Montoro, et al. 2005Montoro P, Braca A, Pizza C, De Tommasi N. Structure- antioxidant activity relationships of flavonoids isolated from different plant species. Food Chem. 2005;92(2):349-55.)
3	9.2	zataroside A	267	-	[M-H]- 327	MS-UV, NMR	(Ali, et al. 1999Ali MS, Saleem M, Akhtar F, Jahangir M, Parvez M, Ahmad VU. Three p-cymene derivatives from Zataria multiflora. Phytochemistry. 1999;52(4):685-8.)
4	9.4	ombuside	261	[M+H]⁺ 639	-	MS-UV	(Deulofeu, Noire, Hug, 1952Deulofeu V, Noire B, Hug E. The flavonic glycosides of Ombu. II. The presence of rutin and identification of ombuside as 4’, 7-dimethylquercetin. Gazz Chem Ital. 1952;82:726-9.)
5	9.7	zataroside B	265	-	[M-H]- 327	MS-UV, NMR	(Ali, et al. 1999Ali MS, Saleem M, Akhtar F, Jahangir M, Parvez M, Ahmad VU. Three p-cymene derivatives from Zataria multiflora. Phytochemistry. 1999;52(4):685-8.)
6	10	diosmetin 7-rutinoside	262, 330	[M+H]⁺ 623	[M-H]- 621	MS-UV, NMR	(Schneider, Blaut, 2000Schneider H, Blaut M. Anaerobic degradation of flavonoids by Eubacterium ramulus. Arch Microbiol. 2000;173(1):71-5.)
7	10.7	rhoifolin	261, 310	[M+H]⁺ 579	[M-H]- 577	MS-UV	(Hattori, Matsuda, 1952Hattori S, Matsuda H. Rhoifolin, a new flavone glycoside, isolated from the leaves of Rhus succedanea. Arch Biochem Biophys. 1952;37(1):85-9.)
8	10.8	quercetin-7-glucuronide	265, 351	-	[M-H]- 451	MS-UV	(O’Leary, et al. 2003O’Leary KA, Day AJ, Needs PW, Mellon FA, O’Brien NM, Williamson G. Metabolism of quercetin-7-and quercetin-3-glucuronides by an in vitro hepatic model: the role of human β-glucuronidase, sulfotransferase, catechol-O-methyltransferase and multi-resistant protein 2 (MRP2) in flavonoid metabolism. Biochem Pharmacol. 2003;65(3):479-91.)
9	11.2	rutin	262, 330	[M+H]⁺ 611	[M-H]- 609	MS-UV	(Zhishen, Mengcheng, Jianming, 1999Zhishen J, Mengcheng T, Jianming W. The determination of flavonoid contents in mulberry and their scavenging effects on superoxide radicals. Food Chem. 1999;64(4):555-9.)
10	12.0	apigenin-7-O- β-Dglucuronide	266, 323	[M+H]⁺ 447	[M-H]- 445, 2[M-H]- 891	MS-UV	(De Bruyne, et al. 1999De Bruyne T, Pieters L, Dommisse R, Kolodziej H, Wray V, Berghe DV, et al. NMR characterization and biological evaluation of proanthocyanidins: A systematic approach. Plant Polyphenols 2: Springer.1999;193-209.)
11	12.4	rosmarinic acid	246, 284, 325	-	[M-H]- 359, 2[M-H]- 719	MS-UV, NMR	(Petersen, Simmonds, 2003Petersen M, Simmonds MSJ. Rosmarinic acid. Phytochemistry . 2003;62(2):121-5.)
12	13.1	methyl rosmarinate	269	-	[M-H]- 373	MS-UV, NMR	(Woo, Piao, 2004Woo E-R, Piao MS. Antioxidative constituents fromlycopus lucidus. Arch Pharmacol Res. 2004;27(2):173-6.)
13	13.1	linarin	319	[M+H]⁺ 593	[M-H]- 591	MS-UV, NMR	(Ina, Iida, 1981)
14	13.2	isomelitric acid A	253, 286, 324		[M-H]- 537	MS-UV, NMR	(Agata, et al. 1993Agata I, Kusakabe H, Hatano T, Nishibe S, Okuda T. Melitric acids A and B, new trimeric caffeic acid derivatives from melissa officinalis. Chem Pharm Bull. 1993;41(9):1608-11.)
15	13.5	poncirin	267, 321	[M+H]⁺ 595	[M-H]- 593	MS-UV	(Lee, et al. 2009Lee JH, Lee SH, Kim YS, Jeong CS. Protective effects of neohesperidin and poncirin isolated from the fruits of Poncirus trifoliata on potential gastric disease. Phytother Res. 2009;23(12):1748-53.)
16	13.7	(7’R, 8’ R, 8’’R, 8’’’R)-episalvianolic acid B	256, 285, 316	-	[M-H]- 717	MS-UV, NMR	-
17	13.7	methyl militrinate	254, 284, 313	-	[M-H]- 551	MS-UV, NMR	(Dapkevicius, et al. 1999Dapkevicius A, Venskutonis R, van Beek TA, Linssen JPH. Antioxidant activity of extracts obtained by different isolation procedures from some aromatic herbs grown in Lithuania. J Sci Food Agric. 1999;77(1):140-6.)
18	13.9	lycopic acid C	255, 287, 317	[M+H]⁺ 521	-	MS-UV, NMR	(Murata, et al. 2010Murata T, Watahiki M, Tanaka Y, Miyase T, Yoshizaki F. Hyaluronidase Inhibitors from Takuran, Lycopus lucidus. Chem Pharm Bull . 2010;58(3):394-7.)
19	14.4	saturejenol	275.331		[M-H]- 451	MS-UV, NMR	(Davoodi, Rustaiyan, Ebrahimi, 2018Davoodi M, Rustaiyan A, Ebrahimi SN. Monoterpene Flavonoid from Aerial Parts of Satureja khuzistanica. Rec Nat Prod. 2018;12(2):175-8.)
20	15.0	diosmin	279, 339		[M-H]- 607	MS-UV, NMR	(Nieto, Gutierrez, 1986Nieto JL, Gutierrez AM. 1H NMR Spectra at 360 MHz of Diosmin and Hesperidin in DMSO Solution. Spectrosc Lett. 1986;19(5):427-34.)
21	16.6	keshonin	269, 328	[M+H]⁺ 611	[M-H]- 609	MS-UV, NMR	(Yamada, et al. 2010Yamada K, Murata T, Kobayashi K, Miyase T, Yoshizaki F. A lipase inhibitor monoterpene and monoterpene glycosides from Monarda punctata. Phytochemistry . 2010;71(16):1884-91.)
22	21.0	saturejin	245, 266, 342	[M+H]⁺ 435	[M-H]- 433	MS-UV	(Malmir, et al. 2015Malmir M, Gohari AR, Saeidnia S, Silva O. A new bioactive monoterpene-flavonoid from Satureja khuzistanica. Fitoterapia. 2015;105:107-12.)

position	δ_H(J in Hz)	δ _C ^a	Hey HMBC signals (H → C)
1		124.4
3		146.4
4		147.7
5	6.82 (d, 8.4)	117.8
6	7.25 (d, 8.5)	120.9
7	7.61 (d, 15.9)	142.6	1, 9
8	6.29 (d, 15.9)	115.8	1, 9
9		169.6
2'	6.67 (d, 1.8)	117.0
5'	6.71 (d, 8.2)	116.0
6'	6.51 (dd, 8.1, 1.9)	117.3
7'	5.72 (d, 4.8)	86.4	6', 4, 9', 2'
8'	4.34 (d, 4.9)	55.7	9', 1, 3,
9'		171.6
1''		127.6
2''	6.59 (d, 8.0)	115.8
5''	6.60 (d, 8.0)	115.8
6''	6.42 (dd, 8, 1.8)	120.5
7’’a	2.96 (dd, 14.3, 7.5)	36.5
7’’b	2.99 (dd, 14.6, 4.7)	36.5
8''	5.04 (dd, 7.7, 4.9)	74.9	9'', 1'',9
9''		173.9
2'''	6.63 (d, 1.8)	116.9
5'''	6.71 (d, 8.2)	112.9
6'''	6.51 (dd, 8.1, 1.9)	120.3
7’’’a	6.91 (dd, 13. 1,8.7)	36.5	2'''
7’’’b	2.88 (m)	36.5
8'''	4.96 (dd, 8.7, 4.2)	74.1	9'''
9'''		165.1

Compounds	Pseudomonas aeruginosa		Staphylococcus aureus
Compounds	inhibition zone (mm)^a	MIC (μg/ mL)	inhibition zone (mm)^a	MIC (μg/ mL)
carvacrol ^b	20	0.34	19	0.37
carvacrol+compound 6 ^c	25	0.19	21	0.21
carvacrol+compound 13 ^d	28	0.16	23	0.18
compound 6 ^e	18	0.39	16	0.39
compound 13 ^f	19	0.38	18	0.38
polymyxin E		0.04		0.37
ciprofloxacin		0.50		No
imipeneme		4.00		1.00
gentamycin		2.00		5.00

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: S. Nejad-Ebrahimi. Department of Phytochemistry. Medicinal Plants and Drugs Research Institute. Shahid Beheshti University, G. C. Evin, Tehran, Iran. Telefax: +98-21-22431783. E-mail address: s_ ebrahimi@sbu.ac.ir. ORCID: 0000-0003-2167-8032