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Molbank
Volume 2019
Issue 3
10.3390/M1078
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Open AccessCommunication

A-Ring-Modified Triterpenoids and Their Spermidine–Aldimines with Strong Antibacterial Activity

by 1,*, 2,*, 1, 2, 1, 1 and 1
1
Ufa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa 450054, 71 pr. Oktyabrya, Russia
2
Aix Marseille Université, INSERM, SSA, MCT, 13385 Marseille, France
*
Authors to whom correspondence should be addressed.
Molbank 2019, 2019(3), M1078; https://doi.org/10.3390/M1078
Received: 2 August 2019 / Revised: 3 September 2019 / Accepted: 5 September 2019 / Published: 6 September 2019
(This article belongs to the Section Natural Products)
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Abstract

Synthesis of A-ring-modified lupane, oleanane and ursane type triterpenoid conjugates with spermidine through an aldimine linkage or diethylentriamine via an amide bond is described. These derivatives were evaluated for their in vitro antimicrobial properties against human pathogens. Except for derivatives 1 and 7, all compounds have moderate to weak minimum inhibitory concentrations (MICs) against Gram-positive Staphylococcus aureus bacteria, with MICs varying from 3.125 to 200 µM. Compound 11 is efficient against Escherichia coli and Pseudomonas aeruginosa, with MICs of 25 and 50 µM, respectively, while all other derivatives do not possess important antimicrobial activities against these Gram-negative bacteria.
Keywords: triterpenoids; lupane; oleanane; ursane; spermidine; spermine; squalamine; antimicrobial activity; Gram-positive bacteria; Gram-negative bacteria triterpenoids; lupane; oleanane; ursane; spermidine; spermine; squalamine; antimicrobial activity; Gram-positive bacteria; Gram-negative bacteria
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited
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MDPI and ACS Style

Kazakova, O.B.; Brunel, J.M.; Khusnutdinova, E.F.; Negrel, S.; Giniyatullina, G.V.; Lopatina, T.V.; Petrova, A.V. A-Ring-Modified Triterpenoids and Their Spermidine–Aldimines with Strong Antibacterial Activity. Molbank 2019, 2019, M1078.

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