Characterization and Biological Activity of Native and Sulfated Noni (<i>Morinda citrifolia</i> Linn.) Pectin

Santos, Denilton G.; Cunha, Arcelina P.; Ribeiro, Ana C. B.; Brito, Débora H. A.; Alenca, Luciana M. R.; Farias, Davi F.; Carvalho, Ana F. F. U.; Sousa, João A. C.; Leal, Luzia K. A. M.; Lopes, Nayara; Linhares, Rosa E. C.; Nozawa, Carlos; Uchoa, Antonia F. J.; Ribeiro, Maria E. N. P.; Ricardo, Nágila M. P. S.

doi:10.21577/0103-5053.20230156

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Article • J. Braz. Chem. Soc. 35 (4) • 2024 • https://doi.org/10.21577/0103-5053.20230156 linkcopy

Characterization and Biological Activity of Native and Sulfated Noni (Morinda citrifolia Linn.) Pectin

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

The aim of this work was to extract and characterize pectin from lyophilized noni pulp (Morinda citrifolia Linn.) at three different pHs using different extractor agents and to evaluate anti-viral activity. The extraction of high yield (acid extraction) was subjected to sulfation procedure. Fourier transform infrared spectroscopy and proton nuclear magneticresonance analysis were used to calculate the degree of methylation of pectin from acid extraction and its sulfated derivative. The data obtained for the degree of methylation of noni pectin and sulfated pectin were 30.3 and 30.7, respectively. Pectin was subjected to acute oral toxicity testing in mice. The results showed that pectin had a pro-inflammatory effect, and sulfated pectin had an anti-inflammatory effect. Both pectins were also evaluated for herpes simplex virus activity in vitro, and although they successfully inhibited virus replication, the sulfated pectins were cytotoxic.

Keywords:
noni pectin; cytotoxicity; HSV

Authorship

person Denilton G. Santos

conceptualization · validation · read and agreed to the published version of the manuscript

schoolDepartamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, Campus do Pici, 60455-760 Fortaleza-CE, BrazilUniversidade Federal do CearáBrazilFortaleza, CE, BrazilDepartamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, Campus do Pici, 60455-760 Fortaleza-CE, Brazil

person Arcelina P. Cunha

conceptualization · read and agreed to the published version of the manuscript

person Ana C. B. Ribeiro

conceptualization · read and agreed to the published version of the manuscript

person Débora H. A. Brito

writing-original draft preparation · writing - review and editing · read and agreed to the published version of the manuscript

person Luciana M. R. Alenca

formal analysis · read and agreed to the published version of the manuscript

schoolLaboratório de Biofísica e Biosistema, Departamento de Física, Universidade Federal do Maranhão, 65080-805 São Luís-MA, BrazilUniversidade Federal do MaranhãoBrazilSão Luís, MA, BrazilLaboratório de Biofísica e Biosistema, Departamento de Física, Universidade Federal do Maranhão, 65080-805 São Luís-MA, Brazil

person Davi F. Farias

methodology · read and agreed to the published version of the manuscript

schoolDepartamento de Biologia, Centro de Ciências, Universidade Federal do Ceará, Campus do Pici, 60440-900 Fortaleza-CE, BrazilUniversidade Federal do CearáBrazilFortaleza, CE, BrazilDepartamento de Biologia, Centro de Ciências, Universidade Federal do Ceará, Campus do Pici, 60440-900 Fortaleza-CE, Brazil

person Ana F. F. U. Carvalho

methodology · read and agreed to the published version of the manuscript

person João A. C. Sousa

methodology · read and agreed to the published version of the manuscript

schoolDepartamento de Farmácia, Faculdade de Farmácia, Odontologia e Enfermagem, Universidade Federal do Ceará, 60430-170 Fortaleza-CE, BrazilUniversidade Federal do CearáBrazilFortaleza, CE, BrazilDepartamento de Farmácia, Faculdade de Farmácia, Odontologia e Enfermagem, Universidade Federal do Ceará, 60430-170 Fortaleza-CE, Brazil

person Luzia K. A. M. Leal

investigation · read and agreed to the published version of the manuscript

person Nayara Lopes

investigation · read and agreed to the published version of the manuscript

schoolDepartamento de Microbiologia, Centro de Ciências Biológicas, Universidade Estadual de Londrina, 86051-990 Londrina-PR, BrazilUniversidade Estadual de LondrinaBrazilLondrina, PR, BrazilDepartamento de Microbiologia, Centro de Ciências Biológicas, Universidade Estadual de Londrina, 86051-990 Londrina-PR, Brazil

person Rosa E. C. Linhares

investigation · read and agreed to the published version of the manuscript

person Carlos Nozawa

investigation · read and agreed to the published version of the manuscript

person Antonia F. J. Uchoa

visualization · read and agreed to the published version of the manuscript

person Maria E. N. P. Ribeiro

resources · visualization · read and agreed to the published version of the manuscript

0000-0001-6896-7179

person Nágila M. P. S. Ricardo *

conceptualization · resources · writing-original draft preparation · writing - review and editing · supervision · project administration · funding acquisition · read and agreed to the published version of the manuscript

0000-0003-1849-5403

person* e-mail:
naricard@ufc.br

Editor handled this article: Paulo Cezar Vieira

SCIMAGO INSTITUTIONS RANKINGS

Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, Campus do Pici, 60455-760 Fortaleza-CE, BrazilUniversidade Federal do CearáBrazilFortaleza, CE, BrazilDepartamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, Campus do Pici, 60455-760 Fortaleza-CE, Brazil

Laboratório de Biofísica e Biosistema, Departamento de Física, Universidade Federal do Maranhão, 65080-805 São Luís-MA, BrazilUniversidade Federal do MaranhãoBrazilSão Luís, MA, BrazilLaboratório de Biofísica e Biosistema, Departamento de Física, Universidade Federal do Maranhão, 65080-805 São Luís-MA, Brazil

Departamento de Biologia, Centro de Ciências, Universidade Federal do Ceará, Campus do Pici, 60440-900 Fortaleza-CE, BrazilUniversidade Federal do CearáBrazilFortaleza, CE, BrazilDepartamento de Biologia, Centro de Ciências, Universidade Federal do Ceará, Campus do Pici, 60440-900 Fortaleza-CE, Brazil

Departamento de Farmácia, Faculdade de Farmácia, Odontologia e Enfermagem, Universidade Federal do Ceará, 60430-170 Fortaleza-CE, BrazilUniversidade Federal do CearáBrazilFortaleza, CE, BrazilDepartamento de Farmácia, Faculdade de Farmácia, Odontologia e Enfermagem, Universidade Federal do Ceará, 60430-170 Fortaleza-CE, Brazil

Departamento de Microbiologia, Centro de Ciências Biológicas, Universidade Estadual de Londrina, 86051-990 Londrina-PR, BrazilUniversidade Estadual de LondrinaBrazilLondrina, PR, BrazilDepartamento de Microbiologia, Centro de Ciências Biológicas, Universidade Estadual de Londrina, 86051-990 Londrina-PR, Brazil

Figures | Tables | Formulas

Figures (4)
Tables (2)
Formulas (4)

Thumbnail

Figure 1 Chemical structure of the monomer unit of pectin (a) and expansion of a region of the 1H NMR spectrum (300 MHz, D₂O) of PDN-a sample showing the peak integrals used for DM estimation (b).

Thumbnail

Figure 2 Topographic AFM maps (2 µm scan size) of the PDN-a (a) and PDN-s (b) samples and their respective three-dimensional maps (c, d). The scale bars represent the heights (maximum values) of the structures observed in the images.

Thumbnail

Figure 3 Topographic images of the PDN-a (a) and PDN-s (b) samples. The scan has 1 × 1 µm. Adhesion maps (c and d) corresponding to the scan regions shown in (a) and (b). (e) Cross section of the blue dotted line in (a). (f) Cross section of the blue dotted line in image (b). (g) Image corresponding to the region of the green dotted square observed in image (b). (h) Adhesion map corresponding to the detail shown in (c) de-limited by the green dotted square. The blue arrows show globular structures that make up the chains that form the network observed in the PDN-a sample.

Thumbnail

Figure 4 Effects of pectin and sulfated pectin on the release of the myeloperoxidase enzyme in human neutrophils stimulated by PMA (0.1 µM). Hanks: non-treated cells, vehicle: water (control group), INDO (indomethacin, 100 µM). *vs. Hanks (untreated cells) ^#vs. vehicle (positive control). Results represent means ± equine protozoal myeloencephalitis. (p < 0.05; ANOVA and Tukey’s post hoc test).

Thumbnail

Table 1 The percentage of yield from different pH values during extraction

Thumbnail

Table 2 Elemental analysis for pectin (PDN-a) and sulfated pectin (PDN-s)

(1)

(2)

(3)

(4)

imageFigure 1 Chemical structure of the monomer unit of pectin (a) and expansion of a region of the 1H NMR spectrum (300 MHz, D₂O) of PDN-a sample showing the peak integrals used for DM estimation (b). open_in_new

imageFigure 2 Topographic AFM maps (2 µm scan size) of the PDN-a (a) and PDN-s (b) samples and their respective three-dimensional maps (c, d). The scale bars represent the heights (maximum values) of the structures observed in the images. open_in_new

imageFigure 3 Topographic images of the PDN-a (a) and PDN-s (b) samples. The scan has 1 × 1 µm. Adhesion maps (c and d) corresponding to the scan regions shown in (a) and (b). (e) Cross section of the blue dotted line in (a). (f) Cross section of the blue dotted line in image (b). (g) Image corresponding to the region of the green dotted square observed in image (b). (h) Adhesion map corresponding to the detail shown in (c) de-limited by the green dotted square. The blue arrows show globular structures that make up the chains that form the network observed in the PDN-a sample. open_in_new

imageFigure 4 Effects of pectin and sulfated pectin on the release of the myeloperoxidase enzyme in human neutrophils stimulated by PMA (0.1 µM). Hanks: non-treated cells, vehicle: water (control group), INDO (indomethacin, 100 µM). *vs. Hanks (untreated cells) ^#vs. vehicle (positive control). Results represent means ± equine protozoal myeloencephalitis. (p < 0.05; ANOVA and Tukey’s post hoc test). open_in_new

table_chartTable 1 The percentage of yield from different pH values during extraction

Pectin	Mass / g	Yield / %
PDN-a	3.8789	19.39
PDN-n	2.9681	14.84
PDN-b	2.4582	12.29

table_chartTable 2 Elemental analysis for pectin (PDN-a) and sulfated pectin (PDN-s)

Sample	Carbon / %	Sulfur / %	Nitrogen / %	Hydrogen / %
PDN-a	30.11	Trace	6.35	5.50
PDN-s	9.46	9.72	0.66	2.40

(1)

DM = \frac{I_{{COOCH}_{3}} + I_{H - 2}}{I_{H - 3}}

(2)

DS = [162 \times (% S / 32)] / {100 - [(80 / 32) \times) % S)]}

(3)

A = [\frac{(A_{1} - A_{2})}{2}] \times 1746.03

(4)

DS = \frac{1.62 \times S %}{32 - (1.02 \times S %)}

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