Anti-HIV Activity of Alkaloids fromDasymaschalon echinatum

Abstract

Bioassay-guided fractionation of the aerial parts of Dasymaschalon echinatum led to the isolation of five known aristolactams; aristolactam AII (1), aristolactam BII (2), piperolactam A (3), piperolactam C (4), and goniopedaline (5), together with two aphorphine alkaloids; duguevalline (6) and noraristolodione (7) and two amide derivatives; asperphenamate (8), and N-benzoyl-L-phenylalaninol (9). Alkaloids 2 and 7 were isolated for the first time from the Dasymaschalon genus. The anti-HIV 1 reverse transcriptase (RT) activity of all isolated compounds was determined. Except for aristolactam BII (2), this is the first report of the anti-HIV 1-RT activity of compounds 1 and 3-9. Compounds 1, 3, 5, 6 and 8 showed weak anti-HIV 1-RT inhibitory activity with IC 50 ranging from 112.74 to 225.55 M.

Przeciwwirusowe związki izolowane z roślin

“…W grupie tej znajdują się związki, których mechanizm działania polega na blokowaniu replikacji wirusa w wyniku wiązania i/lub hamowania działania odwrotnej transktyptazy, m.in. korydyna znajdująca się w ekstrakcie liści krotona (Croton echinocarpus), aristolaktamy pochodzące z Dasymaschalon echinatum, emetyna z ipekakuany prawdziwej (Psychotria ipecacuanha), czy papaweryna z maku lekarskiego (Papaver somniferum) [11][12][13][14].…”

Mass Spectrometry Guided Discovery and Design of Novel Asperphenamate Analogs From Penicillium astrolabium Reveals an Extraordinary NRPS Flexibility

“…Asperphenamate, first discovered from Aspergillus flavipes in 1977 ( Clark et al, 1977 ), was since found to be produced by a wide range of Aspergillus ( Samson et al, 2011 ; Zheng et al, 2013 ; Ratnaweera et al, 2016 ; Hou et al, 2017 ) and Penicillium ( Frisvad et al, 2004 , 2013 ) species. Additionally, the compound has also been isolated in trace amounts from a number of unrelated plant species ( Wu et al, 2004 ; Dang et al, 2014 ; Zhou et al, 2017 ; Bunteang et al, 2018 ; Caridade et al, 2018 ), suggesting endophytic fungi being the actual producers, rather than the plants. Although asperphenamate is mainly known for its antitumour activity and immense synthetic chemists interest in asperphenamate backbone modification ( Li et al, 2012 ; Yuan et al, 2012 , 2018 , 2019 , 2020 ; Liu et al, 2016 ), recent studies have also shown asperphenamate to be a potential neuroinflamatory inhibitor ( Zhou et al, 2017 ), and to possess anti-HIV ( Bunteang et al, 2018 ) and antidiabetic ( Del Valle et al, 2016 ) properties.…”

“…Additionally, the compound has also been isolated in trace amounts from a number of unrelated plant species ( Wu et al, 2004 ; Dang et al, 2014 ; Zhou et al, 2017 ; Bunteang et al, 2018 ; Caridade et al, 2018 ), suggesting endophytic fungi being the actual producers, rather than the plants. Although asperphenamate is mainly known for its antitumour activity and immense synthetic chemists interest in asperphenamate backbone modification ( Li et al, 2012 ; Yuan et al, 2012 , 2018 , 2019 , 2020 ; Liu et al, 2016 ), recent studies have also shown asperphenamate to be a potential neuroinflamatory inhibitor ( Zhou et al, 2017 ), and to possess anti-HIV ( Bunteang et al, 2018 ) and antidiabetic ( Del Valle et al, 2016 ) properties. In recent years, a handful of new natural analogs have been isolated, namely Asperphenamates B ( 4 ) and C ( 5 ) ( Liu et al, 2018 ), and 4-OMe-asperphenamate ( Zheng et al, 2013 ; Ratnaweera et al, 2016 ) ( 6 ) from filamentous fungi.…”