Please use this identifier to cite or link to this item:
http://hdl.handle.net/1843/59051
Type: | Tese |
Title: | Estudo fitoquímico e biológico de Maytenus quadrangulata (Celastraceae) |
Other Titles: | Phytochemical and biological study of Maytenus quadrangulata (Celastraceae) Estudio fitoquímico y biológico de Maytenus quadrangulata (Celastraceae) |
Authors: | Mariana Guerra de Aguilar |
First Advisor: | Lucienir Pains Duarte |
First Co-advisor: | Grasiely Faria de Sousa |
First Referee: | Luciana Alves Rodrigues dos Santos Lima |
Second Referee: | Roqueline Rodrigues Silva |
Third Referee: | Rossimiriam Pereira de Freitas |
metadata.dc.contributor.referee4: | Rosemeire Brondi Alves |
Abstract: | Este trabalho descreve o estudo fitoquímico e biológico das folhas, galhos e raízes de Maytenus quadrangulata (Celastraceae). O estudo fitoquímico das folhas e raízes resultou no isolamento e identificação estrutural de 41 compostos, dos quais 31 são triterpenos pentacíclicos. Entre os triterpenos, têm-se quinze de esqueleto friedelânico (friedelan-3-ona, friedelan-3β-ol, friedelan-3α-ol, friedelano-3,7-diona, 11β-hidroxifriedelan-3-ona, 3β-hidroxifriedelan-7-ona, 3α-hidroxifriedelan-7-ona, friedelano-2α,3α-diol, friedelano-3α,16β-diol, friedelano-3α,11β-diol, friedelano-3α,25-diol, 3α,29-diacetiloxifriedelano, 3α,11β-diacetiloxifriedelano, 3β,24-diacetiloxifriedelano, 3α,25-diacetiloxifriedelano e 24-acetiloxifriedelan-3β-ol), dez de esqueleto lupano (lup-20(29)-en-3-ol, 11α-hidroxilup-1:20(29)-dien-3-ona, 11α-hidroxilup-20(29)-en-3-ona, lup-20(29)-eno-3,11α-diol, lup-20(29)-eno-1,3-diol e lup-20(29)-eno-2α,3,11α-triol, ácido 2,3-seco-lup-20(29)-en-2,11α-olideo-3-óico), dois de esqueleto oleanano (3α-quadrangulanol e olean-9(11):12-dien-3-ol), um quinonametídeo (tingenona) e quatro dímeros (escutionina αA, 7,8-di-hidroescutionina αA, escutidina αA e 7,8-di-hidroisoxuxuarina Eα). Além dos triterpenos, também foram isolados dois esteroides (-sitosterol e 3-O--D-glicosil--sitosterol), dois flavonoides (4’-O-metilepigalocatequina e 4’-O-metilepigalocatequina 5-O--D-glicopiranosídeo), duas naftoquinonas (lapachol e desidro-α-lapachona), um aldeído fenólico (siringaldeído), um derivado da tropona (4,8-di-hidroxi-7-metil-1-oxaespiro[2.6]nona-6,8-dien-5-ona), um alcaloide macrocíclico sesquiterpênico (8-O-desacetileuonina) e um alcaloide macrocíclico derivado da espermidina (N(9)-acetil-N(9)-desoximaifolina). Dentre os compostos obtidos, oito são relatados pela primeira vez na literatura, incluindo 3α,29-diacetiloxifriedelano, 3α,11β-diacetiloxifriedelano, 3α,25-diacetiloxifriedelano, 24-acetiloxifriedelan-3β-ol, 3α-quadrangulanol, lup-20(29)-eno-2α,3,11α-triol, ácido 2,3-seco-lup-20(29)-en-2,11α-olideo-3-óico e 4,8-di-hidroxi-7-metil-1-oxaespiro[2.6]nona-6,8-dien-5-ona. Destaca-se também, o triterpeno friedelano-3α,25-diol isolado pela primeira vez de uma espécie vegetal. Os extratos metanólicos das folhas, galhos e raízes, bem como o extrato acetato etílico das raízes, foram analisados por UHPLC-HRMS. Foram identificados putativamente 53 compostos, incluindo flavonoides, triterpenos, alcaloides, glicosídeos, antocianina, sesquiterpeno e lipídeos. O estudo das atividades biológicas consistiu na atividade contra os vírus Mayaro e Zika, atividade antifúngica e antiproliferativa frente a linhagens de células cancerígenas. Os extratos das folhas e galhos de M. quadrangulata apresentaram atividade anti-Zika e anti-Mayaro. Em especial, o extrato acetato etílico das folhas apresentou efeito pronunciado contra os vírus Mayaro e Zika, e o extrato acetato etílico dos galhos apresentou efeito acentuado frente ao vírus Zika. Esses extratos demostraram baixa toxicidade para células Vero, com valores de concentração citotóxica (CC50) superiores a 953 µg/mL, potente inibição, concentração efetiva (CE50) menores que 12 µg/mL e alta seletividade, com índices superiores a 79. |
Abstract: | This work describes the phytochemical and biological study of leaves, branches, and roots of Maytenus quadrangulata (Celastraceae). The phytochemical study of the leaves and roots led to the isolation and structural identification of 41 compounds of which 31 are pentacyclic triterpenes. Among the triterpenes, fifteen belong to the friedelane skeleton (friedelan-3-one, friedelan-3β-ol, friedelan-3α-ol, friedelane-3,7-dione, 11β-hydroxyfriedelan-3-one, 3β-hydroxyfriedelan-7-one, 3α-hydroxyfriedelan-7-one, friedelane-2α,3α-diol, friedelane-3α,16β-diol, friedelane-3α,11β-diol, friedelane-3α,25-diol, 3α,29-diacetoxyfriedelane, 3α,11β-diacetoxyfriedelane, 3β,24-diacetoxyfriedelane, 3α,25-diacetoxyfriedelane, and 24-acetoxyfriedelan-3β-ol), ten belong to the lupane skeleton (lup-20(29)-en-3β-ol, 11α-hydroxylup-1:20(29)-dien-3-one, 11α-hydroxylup-20(29)-en-3-one, lup-20(29)-ene-3β,11α-diol, lup-20(29)-ene-1β,3β-diol, and lup-20(29)-ene-2α,3β,11α-triol, 2,3-seco-lup-20(29)-en-2,11α-olide-3-oic acid), two belong to the oleanane skeleton (3α-quadrangulanol and olean-9(11):12-dien-3β-ol), one is a quinonemethide (tingenone), and four are dimers (escutionin αA, 7,8-di-hydroescutionin αA, escutidin αA, and 7,8-di-hydroisoxuxuarin Eα). In addition to the triterpenes, two steroids (β-sitosterol and 3-O-β-D-glucosyl-β-sitosterol), two flavonoids (4'-O-methylepigallocatechin and 4'-O-methylcatechin 5-O-β-D-glucopyranoside), two naphthoquinones (lapachol and dehydro-α-lapachone), one phenolic aldehyde (syringaldehyde), one tropane derivative (4,8-dihydroxy-7-methyl-1-oxaspiro[2.6]nona-6,8-dien-5-one), one sesquiterpene macrocyclic alkaloid (8-O-desacetyleuonine), and one macrocyclic alkaloid derivative of spermidine (N(9)-acetyl-N(9)-desoxymaifoline) were isolated. Among the isolated compounds, eight are reported for the first time in the literature, including 3α,29-diacetoxyfriedelane, 3α,11β-diacetoxyfriedelane, 3α,25-diacetoxyfriedelane, 24-acetoxyfriedelan-3β-ol, 3α-quadrangulanol, lup-20(29)-ene-2α,3β,11α-triol, 2,3-seco-lup-20(29)-en-2,11α-olide-3-oic acid, and 4,8-dihydroxy-7-methyl-1-oxaspiro[2.6]nona-6,8-dien-5-one. It is worth noting that friedelane-3α,25-diol was isolated for the first time from a plant species. The methanolic extracts the leaves, branches, and roots, as well as the ethyl acetate extract of the roots, were analyzed by UHPLC-HRMS. A total of 53 compounds were identified putatively from this analysis, including flavonoids, triterpenes, alkaloids, glycosides, anthocyanins, sesquiterpenes and lipids. The study of the biological activities consisted of antiviral activity against Mayaro and Zika viruses, antifungal and antiproliferative activity against cancer cell lines. Extracts from the leaves and branches of M. quadrangulata showed anti-Zika and anti-Mayaro activities. In particular, the ethyl acetate extract of the leaves showed pronounced effects against Mayaro and Zika viruses, and the ethyl acetate extract of the branches exhibited significant effects against Zika virus. These extracts demonstrated low toxicity to Vero cells, with cytotoxic concentration (CC50) values higher than 953 µg/mL, potent inhibition with effective concentration (EC50) lower than 12 µg/mL, and high selectivity with indices higher than 79. |
Subject: | Química orgânica Celastraceae Maytenus Terpênios Esteroides Flavonoides Quinona Aldeídos Alcalóides Atividade antifúngica Agentes antineoplásicos Cromatografia líquida de alta eficiência Testes biológicos Matéria médica vegetal |
language: | por |
metadata.dc.publisher.country: | Brasil |
Publisher: | Universidade Federal de Minas Gerais |
Publisher Initials: | UFMG |
metadata.dc.publisher.department: | ICX - DEPARTAMENTO DE QUÍMICA |
metadata.dc.publisher.program: | Programa de Pós-Graduação em Química |
Rights: | Acesso Restrito |
URI: | http://hdl.handle.net/1843/59051 |
Issue Date: | 28-Aug-2023 |
metadata.dc.description.embargo: | 28-Aug-2025 |
Appears in Collections: | Teses de Doutorado |
Files in This Item:
File | Description | Size | Format | |
---|---|---|---|---|
ESTUDO FITOQUÍMICO E BIOLÓGICO DE Maytenus quadrangulata (CELASTRACEAE).pdf ???org.dspace.app.webui.jsptag.ItemTag.restrictionUntil??? 2025-08-28 | 17.52 MB | Adobe PDF | View/Open Request a copy |
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.