Phytotoxic property of metabolites isolated from Garcinia gardneriana

Dayana A Rodrigues; Bianca L de Sousa; Júnio G da Silva; Gustavo A M Pereira; Guilherme M Bousada; Antonio A da Silva; Antonio J Demuner; Éderson D'M Costa; Eduardo J Pilau; Evandro Silva; Marcelo H Dos Santos

doi:10.1016/j.compbiolchem.2021.107460

Phytotoxic property of metabolites isolated from Garcinia gardneriana

Comput Biol Chem. 2021 Jun:92:107460. doi: 10.1016/j.compbiolchem.2021.107460. Epub 2021 Feb 16.

Affiliations

¹ Departamento De Química, Universidade Do Estado De Minas Gerais, Rua Vereador Geraldo Moisés Da Silva, s/n, Campus Universitário, 38302192 Ituiutaba, MG, Brazil.
² Departamento De Química, Universidade Federal De Viçosa, Avenida Peter Henry Rolfs, s/n, Campus Universitário, 36570-900 Viçosa, MG, Brazil.
³ Departamento De Química, Universidade Federal De Minas Gerais, Av. Antônio Carlos, 6627, Pampulha, 31270-901 Belo Horizonte, MG, Brazil.
⁴ Departamento De Fitotecnia, Universidade Federal De Viçosa, Avenida Peter Henry Rolfs, s/n, Campus Universitário, 36570-900 Viçosa, MG, Brazil.
⁵ Instituto De Ciências Exatas, Universidade Federal De Alfenas, Rua Gabriel Monteiro Da Silva, 700 - Centro, 37130-001 Alfenas, MG, Brazil.
⁶ Departamento De Química, Universidade Estadual De Maringá, Avenida Colombo, 5790, Campus Universitário, 87020-900 Maringá, PR, Brazil.
⁷ Departamento De Química, Universidade Federal De Viçosa, Avenida Peter Henry Rolfs, s/n, Campus Universitário, 36570-900 Viçosa, MG, Brazil. Electronic address: marceloh.santos@ufv.br.

PMID: 33621907
DOI: 10.1016/j.compbiolchem.2021.107460

Abstract

Garcinia gardneriana is a medicinal tree species used in Brazil in the treatment of hepatitis and gastritis. This use is attributed to phenolic compounds, mainly 7-epiclusianone, guttiferone-A and fukugetin, which present several proven biological activities. However, to the best of our knowledge, no study on the phytotoxic activity of G. gardneriana extracts has been conducted until now. This research proposed to isolate and quantify by high-performance liquid chromatography (HPLC) the major compounds from G. gardneriana seed extracts in ethyl acetate and to evaluate their phytotoxic activities. The natural products 7-epiclusianone, guttiferone-A and fukugetin were quantified at concentrations varying from 0.46 to 1.13 mg mL^-1 and were isolated with yields ranging from 7% to 23% (w/w). The phytotoxic assay indicated that the crude extract showed no action on the dry matter of Sorghum bicolor plants, but the isolated compounds fukugetin and 7-epiclusianone had moderate activity. On the other hand, guttiferone-A displayed a greater herbicide activity than glyphosate, a positive control, even in almost three times lower concentrations, causing severe intoxication in the plants. This work is the first report on this activity by the extract of G. gardneriana and its isolated compounds. Besides that, guttiferone-A showed up as a scaffold for the development of new agrochemicals. Complementing these findings, computational studies suggested that this benzophenone can interact effectively with transferase enzymes type, in special caffeic acid O-methyltransferase from S. bicolor (PDB code: 4PGH), indicating a possible mechanism of action in this plant.

Keywords: Docking; Garcinia gardneriana; Metabolites; Phytotoxic activity.

MeSH terms

Biological Products / isolation & purification
Biological Products / metabolism
Biological Products / pharmacology*
Brazil
Chromatography, High Pressure Liquid
Garcinia / chemistry*
Molecular Conformation
Plant Extracts / isolation & purification
Plant Extracts / metabolism
Plant Extracts / pharmacology*
Sorghum / drug effects*

Substances

Biological Products
Plant Extracts