Production of Highly Active Antiparasitic Compounds from the Controlled Halogenation of the Arrabidaea brachypoda Crude Plant Extract

被引：11

作者：

Neuenschwander, Alexandra ^{[1
,2
]}

Rocha, Vinicius P. C. ^{[3
]}

Bastos, Tanira M. ^{[3
]}

Marcourt, Laurence ^{[1
,2
]}

Morin, Hugo ^{[1
,2
]}

da Rocha, Claudia Q. ^{[4
]}

Grimaldi, Gabriela B. ^{[3
]}

de Sousa, Karoline A. F. ^{[3
]}

Borges, Jadson N. ^{[3
]}

Rivara-Minten, Elisabeth ^{[1
,2
]}

Wolfender, Jean-Luc ^{[1
,2
]}

Soares, Milena B. P. ^{[3
]}

Queiroz, Emerson F. ^{[1
,2
]}

机构：

[1] Univ Geneva, Sch Pharmaceut Sci, CMU, CH-1211 Geneva 4, Switzerland

[2] Univ Geneva, Inst Pharmaceut Sci Western Switzerland ISPSW, CMU, CH-1211 Geneva 4, Switzerland

[3] Fiocruz MS, Lab Engn Tecidual & Imunofarmacol, Inst Goncalo Moniz, BR-40296710 Salvador, BA, Brazil

[4] Ctr Ciencia Exatas & Tecnol, Dept Quim, Lab Prod Nat, BR-65080805 Maranhao, MA, Brazil

来源：

JOURNAL OF NATURAL PRODUCTS | 2020年 / 83卷 / 09期

基金：

瑞士国家科学基金会;

关键词：

FAST LIQUID-CHROMATOGRAPHY; CHAGAS-DISEASE; BIOTECHNOLOGICAL HALOGENATION; PHARMACEUTICAL ANALYSIS; NATURAL-PRODUCTS; DRUG DISCOVERY; SMALL-PARTICLE; THERAPEUTICS; PERSPECTIVES;

D O I：

10.1021/acs.jnatprod.0c00433

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Direct halogenation of phenolic compounds present in the CH2Cl2 extract of the roots of Arrabidaea brachypoda was investigated to enhance chemodiversity. The approach is based on eco-friendly reactions using NaBr, NaI, and NaCl in aqueous media to generate multiple " unnatural" halogenated natural products from crude extracts. The halogenation reactions, monitored by UHPLC-PDA-ELSD-MS, were optimized to generate mono-, di-, or trihalogenated derivatives. To isolate these compounds, the reactions were scaled up and the halogenated analogues were isolated by semipreparative HPLC-UV and fully characterized by NMR and HR-MS data. All of the original 16 halogenated derivatives were evaluated for their antiparasitic activities against the parasites Leishmania amazonensis and Trypanosoma cruzi. Compounds presenting selective antiparasitic activities against one or both parasites with IC50 values comparable to the reference were identified.

引用

页码：2631 / 2640

页数：10

共 25 条

[1] Leishmaniasis Worldwide and Global Estimates of Its Incidence
Alvar, Jorge
Velez, Ivan D.
Bern, Caryn
Herrero, Merce
Desjeux, Philippe
Cano, Jorge
Jannin, Jean
den Boer, Margriet
[J]. PLOS ONE, 2012, 7 (05):
[2] Angheben A, 2015, TROP MED INT HEALTH, V20, P246
[3] [Anonymous], 2018, Neglected Tropical Diseases
[4] [Anonymous], 2012, HUMAN AFRICAN TRYPAN
[5] Ecofriendly synthesis of halogenated flavonoids and evaluation of their antifungal activity
Bernini, Roberta
Pasqualetti, Marcella
Provenzano, Gianfranco
Tempesta, Sabrina
[J]. NEW JOURNAL OF CHEMISTRY, 2015, 39 (04) : 2980 - 2987
[6] Drug candidate and target for leishmaniasis
Catta-Preta, Carolina M. C.
Mottram, Jeremy C.
[J]. NATURE, 2018, 560 (7717) : 171 - 172
[7] MECHANISMS OF TOXIC ACTION AND STRUCTURE-ACTIVITY-RELATIONSHIPS FOR ORGANOCHLORINE AND SYNTHETIC PYRETHROID INSECTICIDES
COATS, JR
[J]. ENVIRONMENTAL HEALTH PERSPECTIVES, 1990, 87 : 255 - 262
[8] A critical review on Chagas disease chemotherapy
Coura, JR
de Castro, SL
[J]. MEMORIAS DO INSTITUTO OSWALDO CRUZ, 2002, 97 (01): : 3 - 24
[9] Gastroprotective effects of hydroethanolic root extract of Arrabidaea brachypoda: Evidences of cytoprotection and isolation of unusual glycosylated polyphenols
da Rocha, Claudia Quintino
de-Faria, Felipe Meira
Marcourt, Laurence
Ebrahimi, Samad Nejad
Kitano, Bruna Tiemi
Ghilardi, Amanda Franceschini
Ferreira, Anderson Luiz
de Almeida, Ana Cristina Alves
Dunder, Ricardo Jose
Monteiro Souza-Brito, Alba Regina
Hamburger, Matthias
Vilegas, Wagner
Queiroz, Emerson Ferreira
Wolfender, Jean-Luc
[J]. PHYTOCHEMISTRY, 2017, 135 : 93 - 105
[10] Dimeric Flavonoids from Arrabidaea brachypoda and Assessment of Their Anti-Trypanosoma cruzi Activity
da Rocha, Claudia Quintino
Queiroz, Emerson Ferreira
Meira, Cassio Santana
Magalhaes Moreira, Diogo Rodrigo
Pereira Soares, Milena Botelho
Marcourt, Laurence
Vilegas, Wagner
Wolfender, Jean-Luc
[J]. JOURNAL OF NATURAL PRODUCTS, 2014, 77 (06): : 1345 - 1350

← 1 2 3 →