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 Resjournal_title
Natural product researchauthors
Machado VR,Sandjo LP,Pinheiro GL,Moraes MH,Steindel M,Pizzolatti MG,Biavatti MWdoi
10.1080/14786419.2017.1353982subject
Has Abstractpub_date
2018-02-01 00:00:00pages
275-281issue
3eissn
1478-6419issn
1478-6427journal_volume
32pub_type
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