In vitro antibacterial activity of prenylated guanidine alkaloids from Pterogyne nitens and synthetic analogues

Aline Coqueiro; Luis Octávio Regasini; Paul Stapleton; Vanderlan da Silva Bolzani; Simon Gibbons

doi:10.1021/np500281c

In vitro antibacterial activity of prenylated guanidine alkaloids from Pterogyne nitens and synthetic analogues

Aline Coqueiro, Luis Octávio Regasini, Paul Stapleton, Vanderlan da Silva Bolzani, Simon Gibbons

Research output: Contribution to journal › Article › peer-review

30 Citations (Scopus)

Abstract

The present investigation deals with the antibiotic activity of eight natural guanidine alkaloids and two synthetic analogues against a variety of clinically relevant methicillin-resistant Staphylococcus aureus strains. Galegine (1) and pterogynidine (2) were the most potent compounds, with a minimum inhibitory concentration of 4 mg/L, to all tested strains. The preliminary chemical features correlating to anti-MRSA activity showed that the size of the side chain and the substitution pattern in the guanidine core played a key role in the antibacterial activity of the imino group. Guanidine alkaloids 1 and 2 are promising molecular models for further synthetic derivatives and, thus, for medicinal chemistry studies.

Original language	English
Pages (from-to)	1972-1975
Number of pages	4
Journal	Journal of Natural Products
Volume	77
Issue number	8
Early online date	4 Aug 2014
DOIs	https://doi.org/10.1021/np500281c
Publication status	Published - 22 Aug 2014

Access to Document

10.1021/np500281c

Cite this

@article{015154cf8f8a4f8ea0636d5625ce61e4,

title = "In vitro antibacterial activity of prenylated guanidine alkaloids from Pterogyne nitens and synthetic analogues",

abstract = "The present investigation deals with the antibiotic activity of eight natural guanidine alkaloids and two synthetic analogues against a variety of clinically relevant methicillin-resistant Staphylococcus aureus strains. Galegine (1) and pterogynidine (2) were the most potent compounds, with a minimum inhibitory concentration of 4 mg/L, to all tested strains. The preliminary chemical features correlating to anti-MRSA activity showed that the size of the side chain and the substitution pattern in the guanidine core played a key role in the antibacterial activity of the imino group. Guanidine alkaloids 1 and 2 are promising molecular models for further synthetic derivatives and, thus, for medicinal chemistry studies. ",

author = "Aline Coqueiro and Regasini, {Luis Oct{\'a}vio} and Paul Stapleton and {da Silva Bolzani}, Vanderlan and Simon Gibbons",

year = "2014",

month = aug,

day = "22",

doi = "10.1021/np500281c",

language = "English",

volume = "77",

pages = "1972--1975",

journal = "Journal of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - In vitro antibacterial activity of prenylated guanidine alkaloids from Pterogyne nitens and synthetic analogues

AU - Coqueiro, Aline

AU - Regasini, Luis Octávio

AU - Stapleton, Paul

AU - da Silva Bolzani, Vanderlan

AU - Gibbons, Simon

PY - 2014/8/22

Y1 - 2014/8/22

N2 - The present investigation deals with the antibiotic activity of eight natural guanidine alkaloids and two synthetic analogues against a variety of clinically relevant methicillin-resistant Staphylococcus aureus strains. Galegine (1) and pterogynidine (2) were the most potent compounds, with a minimum inhibitory concentration of 4 mg/L, to all tested strains. The preliminary chemical features correlating to anti-MRSA activity showed that the size of the side chain and the substitution pattern in the guanidine core played a key role in the antibacterial activity of the imino group. Guanidine alkaloids 1 and 2 are promising molecular models for further synthetic derivatives and, thus, for medicinal chemistry studies.

AB - The present investigation deals with the antibiotic activity of eight natural guanidine alkaloids and two synthetic analogues against a variety of clinically relevant methicillin-resistant Staphylococcus aureus strains. Galegine (1) and pterogynidine (2) were the most potent compounds, with a minimum inhibitory concentration of 4 mg/L, to all tested strains. The preliminary chemical features correlating to anti-MRSA activity showed that the size of the side chain and the substitution pattern in the guanidine core played a key role in the antibacterial activity of the imino group. Guanidine alkaloids 1 and 2 are promising molecular models for further synthetic derivatives and, thus, for medicinal chemistry studies.

U2 - 10.1021/np500281c

DO - 10.1021/np500281c

M3 - Article

VL - 77

SP - 1972

EP - 1975

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 8

ER -