Chromatographic profile of xanthones and flavonoids in the anti-dengue extracts of <i>Fridericia samydoides</i> (Cham.) L.G. Lohmann (Bignoniaceae)

Fonseca, Juliane Morais da; Reis, Adriana Cotta Cardoso; Pereira, Guilherme Rocha; Moura, Hélia Maria Marques de; Souza Filho, José Dias; Silva, Breno de Mello; Brandão, Geraldo Célio

doi:10.1590/s2175-97902022e18802

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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/s2175-97902022e18802 copy

Chromatographic profile of xanthones and flavonoids in the anti-dengue extracts of Fridericia samydoides (Cham.) L.G. Lohmann (Bignoniaceae)

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Abstract

The flavonoids and xanthones present in the ethanol extracts of leaves and stems of Fridericia samydoides showed that anti-dengue activities in vitro were investigated qualitatively by liquid chromatography-ultraviolet-mass spectrometry in series. Nineteen flavones and fifteen xanthones were detected and characterized on the basis of their fragmentation pattern in the positive and negative ion mode tandem mass spectrometry spectra and ultraviolet bands. Acacetin, chrysin, vitexin, isovitexin, orientin, isoorientin, mangiferin, 2’-O-trans-caffeoylmangiferin, 2’-O-trans-coumaroylmangiferin and 2’-O-trans-cinnamoylmangiferin were identified by comparison with authentic samples. The other compounds detected were tentatively assigned by analysis of the spectral data and by comparison with literature reports. In addition, it performed the fractionation of the leaves extract leading to the isolation of mangiferin, isovitexin and isoorientin. All extracts and isolated compounds inhibited the Dengue virus replication cycle with EC₅₀ less than 25.0 µg/mL for extracts and 272.5, 85.6 and 79.3 µg/mL for mangiferin, isovitexin and isoorientin, respectively.

Keywords:
Fridericia samydoides; Antiviral activity; Flavonoids; C-glycosyxanthone; Dengue type 2

	Compounds	RT (min)	UV (nm)	[M+H]⁺ (m/z )	[M-H]^- (m/z )	*Fragments (m/z* )**
	C-glycosylflavones
1	Vitexin	2.58	268, 332	433.27	431.32	311.29, 341.48
2	Isovitexin	2.80	269, 327	433.34	431.45	311.10, 341.10
3	Orietin	2.45	258, 323	449.41	447.31	327.16, 357.69
4	Isoorientin	2.49	259, 324	449.48	447.25	327.29, 356.79
5	Violanthin	2.40	272, 315	579.36	577.34	457.20, 487.33
6	Isoviolanthin	2.42	271, 316	579.40	577.21	457.06, 486.69
7	Orientin-2"-O-glycoside	2.57	268, 327	611.50	609.46	447.32, 357.43, 327.40
	O-glycosylflavones
8	Scutellarein 7-O-glucuronide	2.84	280, 326	463.46	461.23	*463.20, 287.04
9	6-Methoxyluteolin 7-O-glycoside	2.72	270, 324	479.47	477.49	315.22, 301.07, 161.11
10	Chrysin-7-O-glucoronide	3.73	270, 324(sh)	431.44	429.22	253.25, 175.13
11	Acacetin 7-O-glucuronide	3.62	262, 323	461.30	459.21	459.21, 283.08, 268.16
12	Hispidulin 7-O-glglucuglucuronide	2.72	273, 323	477.31	475.45	*301.22, 285.83
13	Apigenin 7-O-glucuronide	3.18	264, 323	447.45	444.86	269.07
14	Apigenin 4'-O-glucuronide	4.55	280, 320	447.32	445.24	268.94
15	6(8)-hydroxyluteolin 7-O-glycoside	2.58	268, 331	465.28	463.13	*302.92
	Aglycones
16	Chrysin	5.34	267, 319(sh)	255.24	253,21	211.05, 183.34, 153.06,103.17
17	6-hydroxy-chrysin	4.38	285	271.24	269.21	253.04, 225.45, 165.08, 121.88, 106.83
18	Acacetin	5.52	270, 317	285.29.	283.13	267.96, 238.97, 222.77
19	6(8)-methoxyluteolin	4.50	272, 327	301.45	299.40	286.11, 167.09

	Compounds	RT (min)	UV (nm)	[M+H]⁺ (m/z )	[M-H]^- (m/z )	*Fragments (m/z* )**
20	Mangiferin	2.17	239, 257, 318, 364	423.34	421.38	*301.21, 330.86
21	Isomagiferin	2.01	238, 257, 318, 362	423.41	421.35	*300.96, 330.98
22	Mangiferin benzoyl derivative	2.92	258, 280, 319	543.30	541.46	*421.74, 402.95, 282.87
23	Mangiferin benzoyl derivative	3.02	259, 280, 320	543.43	541.14	*419.59, 403.14, 282.93
24	2''-O-trans-cinnamoylmangiferin	3.82	259, 280, 316	553.36	551.35	404.87, 285.24, 131.04
25	Mangiferin cinnamic derivative	3.85	260, 280, 320	553.49	551.85	404.68, 284.85, 130.99
26	Mangiferin cinnamic derivative	4.00	259, 280, 320	553.56	551.60	404.87, 284.98, 131.17
27	2''-O-trans-coumaroylmangiferin	3.76	260, 280, 319	569.33	567.34	303.13, 273.17, 147.80
28	Mangiferin coumaroyl derivative	3.62	260, 280, 319	569.36	567.27	303.06, 273.16, 147.18
29	Mangiferin coumaroyl derivative	3.71	262, 320	569.47	567.40	302.87, 273.04, 147.12
30	2'-O-trans-coumaroylmangiferin	3.83	259, 280, 316	569.52	567.39	302.93, 285.26, 147.06
31	2''-O-trans-caffeoylmangiferin	3.51	259, 280, 320	585.22	583.89	405.26, 303.11, 284.92, 163.08
32	Mangiferin caffeoyl derivative	3.26	258, 280, 319	585.79	583.20	405.20, 303.12, 285,93 163.27
33	Mangiferin caffeoyl derivative	3.45	259, 280, 318	585.16	583.13	404.82, 302.92, 284.99, 162.90
34	2'-O-trans-caffeoylmangiferin	3.02	257, 280, 318	585.51	583.58	405.13, 303.17, 285.36, 163.02

Extracts/Compounds	LLC-MK2 CC₅₀ (g/mL	^a DENV-2 EC ₅₀ (g/mL	SI	MRC-5 CC₅₀ (g/mL
EEASL	93.6 ± 4.2	< 25.0	> 3.7	> 200
EEASS	> 500	< 25.0	> 3.8	>200
Mangiferin	> 500	272.5 ± 6.7	> 1.8	>200
Isovitexin	> 500	85.6 ± 4.8	5.8	>200
Isoorietin	> 500	79.3 ± 3.2	6.3	>200
Interferon (	-	^bc2.5 x 10³	-	^-

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: G. C. Brandão. Department of Pharmacy. Pharmacy School. Federal University of Ouro Preto. Campus Morro do Cruzeiro, ZIP 35.400-000, Ouro Preto, MG, Brazil. Phone: +55-31-3559-1088; Fax: +55-31-3559-1069. E-mail: celiobrandao@ufop.edu.br or celiobrandao@yahoo.com.