Synthesis of lupeol derivatives and their antileishmanial and antitrypanosomal activities.

Abstract:

:The natural product lupeol 1 was isolated from aerial parts of Vernonia scorpioides with satisfactory yield, which made it viable to be used as starting material in semisynthetic approach. Ten lupeol derivatives 2-11 were prepared by classical procedures. Including, five new esters derivatives 7-11, which were obtained by structural modifications in the isopropylidene fragment. All semisynthetic compounds and lupeol 1-11 were confirmed by 1H NMR, 13C NMR and HRMS. Their antiprotozoal activity was evaluated in vitro against L. amazonensis and T. cruzi. Derivative 6 showed the best antitrypanosomal activity (IC50 = 12.48 μg/mL) and the lowest cytotoxic derivative (CC50 = 161.50 μg/mL). The mechanism of action of the most active derivatives (4, 6 and 11) is not dependent from the enzyme trypanothione reductase.

journal_name

Nat Prod Res

journal_title

Natural product research

authors

Machado VR,Sandjo LP,Pinheiro GL,Moraes MH,Steindel M,Pizzolatti MG,Biavatti MW

doi

10.1080/14786419.2017.1353982

subject

Has Abstract

pub_date

2018-02-01 00:00:00

pages

275-281

issue

3

eissn

1478-6419

issn

1478-6427

journal_volume

32

pub_type

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