Chemical study of <i>Adenocalymma axillarum</i> crude leaf extract and isolated compounds

Andrade, João Paulo Campos; Alves, Osvaine Junior Alvarenga; Costa, Marian Caroline; Gimenez, Valéria Maria Melleiro; Squarisi, Iara Silva; Nicolella, Heloiza Diniz; Pagotti, Mariana Cintra; Tavares, Denise Crispim; Cunha, Wilson Roberto; Silva, Márcio Luís Andrade e; Januario, Ana Helena; Magalhães, Lizandra Guidi; Pauletti, Patrícia Mendonça

doi:10.1590/s2175-97902022e20278

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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/s2175-97902022e20278 copy

Chemical study of Adenocalymma axillarum crude leaf extract and isolated compounds

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Abstract

Adenocalymma axillarum (K.Schum.) L.G. Lohmann is a liana belonging to the family Bignoniaceae. In traditional medicine, the genus Adenocalymma is used to treat fever, skin ailments, and body, joint, and facial muscle pains, and it is also applied as cosmetic. Biological assays conducted with the A. axillarum crude leaf ethanol extract have indicated leishmanicidal activity and absence of cytotoxicity. This study aimed to analyze the A. axillarum leaf ethanol crude extract by high-performance liquid chromatography-high-resolution mass spectrometry- diode array detector (HPLC-HRMS-DAD) and to evaluate the leishmanicidal and cytotoxic activities of this crude extract, its fractions, and isolated compounds. HPLC-HRMS-DAD analysis of this extract revealed that it consisted mainly of flavonoids, with nine major compounds. Extract purification yielded 4-hydroxy-N-methylproline, 6-β-hydroxyipolamiide, quercetin-3-O-robinobioside, hyperin, isorhamnetin-3-O-robinobioside, and 3’-O-methylhyperin, which were identified by Nuclear Magnetic Resonance. The isolated compounds were inactive against Leishmania amazonensis promastigotes and human lung fibroblast cells.

Keywords:
Cytotoxicity; Flavonol; HPLC-HRMS-DAD; Iridoid; Leishmanicidal

	Leishmania amazonensis promastigote		Cell line GM07492A
	% flagellar motility inhibition ± S.D.		CC50
samples	[50 µg/mL]	[50 µM]	[µg/mL]	[µM]
CE	48.77 ± 10.99	-	> 2500	-
F-H	n.a.	-	1550 ± 90	-
F-AC	n.a.	-	466.6 ± 23.3	-
F-HM	n.a.	-	> 2500	-
2	-	n.a.	> 2500	> 17241
3	-	n.a.	> 2500	> 5924
7	-	n.a.	> 1000	> 1639
8	-	n.a.	> 2000	> 4303
9	-	n.a.	> 500	> 801
10	-	n.a.	> 1000	> 2092
Amphotericin B	-	100±0.00a

peak	m/z	tR (min)	ion	Molecular formula	Identification	Error	Ref. (ppm)
1	191.0557	3.7	[M-H]^-	C₇H₁₁O₁₆	Quinic acid	0.52	de Oliveira et al., 2017
2	146.0808	3.9	[M+H]⁺	C₆H₂NO₁₃	4-hydroxy-N-methylproline	-2.74	Grassi et al., 2005
3	421.1325	4.5	[M-H]^-	C₁₇H₂₅O₁₂	6β-hydroxylpolamiide	-4.98	Grassi et al., 2005
4	353.0840	6.2	[M-H]^-	C₁₆H₁₇O₉	O-caffeoyl quinic acid	-9.35	de Oliveira et al., 2017
5	307.1761	8.8	[M+H]⁺	C₁₄H₂₇O₇	n.i.	1.30	A
5	305.1577	8.8	[M-H]^-	C₁₄H₂₅O₇		-7.54
6	623.1952	9.7	[M-H]^-	C₂₉H₃₅O₁₅	verbascoside	-3.85	B
7	609.1435	10.6	[M-H]^-	C₂₇H₂₉O₁₆	Quercetin-3-O-robinobioside	-3.44	C
7	611.1588	10.6	[M+H]⁺	C₂₇H₃₁O₁₆		-3.93
8	465.1018	11.2	[M+H]⁺	C₂₁H₂₁O₁₂	Hyperin	1.07	Grassi et al., 2005, c
8	463.0851	11.2	[M-H]^-	C₂₁H₁₉O₁₂		-5.61
9	623.1606	12.2	[M-H]^-	C₂₈H₃₁O₁₆	Isorhamnetin-3-O-robinobioside	-0.96	C
9	625.1752	12.2	[M+H]⁺	C₂₈H₃₃O₁₆		-2.72
10	479.1177	13.0	[M+H]⁺	C₂₂H₂₃O₁₂	3’-O-methylhyperin	-2.71	Grassi et al., 2005, c
10	477.1011	13.0	[M-H]^-	C₂₂H₂₁O₁₂		-4.61

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: P. M. Pauletti. Centro de Pesquisa em Ciências Exatas e Tecnológicas. Universidade de Franca. Av. Dr. Armando Salles de Oliveira, 201. CEP 14404-600, Franca, São Paulo, Brazil. Phone: +55-16-3711-8871. E-mail: patricia.pauletti@unifran.edu.br. ORCID: https://orcid.org/0000-0003-1831-0050.