Leishmanicidal Activity of (+)-Phyllanthidine and the Phytochemical Profile of Margaritaria nobilis (Phyllanthaceae)

Abstract

Abstract:The effects of the Securinega alkaloid (+)-phyllanthidine on Leishmania (L.) amazonensis and the first chemical investigation of Margaritaria nobilis L.f. (Phyllanthaceae) are described. Treating the parasites with this alkaloid caused a dose-dependent reduction in promastigote growth of 67.68% (IC 50 82.37 µg/mL or 353 µM) and in amastigote growth of 83.96% (IC 50 49.11 µg/mL or 210 µM), together with ultrastructural alterations in the promastigotes. No cytotoxic effect was detected in mammalian cells (CC 50 1727.48 µg/mL or CC 50 5268 µM). Classical chromatographic techniques and spectral methods led to the isolation and identification of betulinic acid, kaempferol, corilagin, gallic acid and its methyl ester, besides (+)-phyllanthidine from M. nobilis leaves and stems. Margaritaria nobilis is another source of the small group of Securinega alkaloids, together with other Phyllanthaceae (Euphorbiaceae s.l.) species. The low toxicity to macrophages and the effects against promastigotes and amastigotes are suggestive that (+)-phyllanthidine could be a promising antileishmanial agent for treating cutaneous leishmaniasis.

In Vitro Antileishmanial Activity of Sterols from Trametes versicolor (Bres. Rivarden)

“…Secondary metabolites from organisms such as higher plants or fungi are a valuable source for the discovery of new bioactive lead structures [6]. Many natural products with the most complex and diverse structures have been isolated from a great variety of organisms and have shown the potential of antileishmanial activity; however, since leishmaniasis is a neglected disease, none of them has undergone clinical evaluation [1,7,8,9,10].…”

Components from the Leaves and Twigs of Mangrove Lumnitzera racemosa with Anti-Angiogenic and Anti-Inflammatory Effects

“…The EtOAc layer was further partitioned with n -hexane and 75% methanol (MeOH) in H 2 O to give a 75% MeOH (aq) layer. One new compound, racelactone A ( 1 ), and seven known compounds: Botulin ( 2 ) [ 14 , 15 ], 3,4,3′-tri- O -methyl ellagic acid ( 3 ) [ 16 ], methyl gallate ( 4 ) [ 17 ], myricitrin ( 5 ) [ 18 ], stigmasterol ( 6 ) [ 19 ], kaempferol ( 7 ) [ 20 ], and isoguaiacin ( 8 ) [ 21 ] were identified from the 75% MeOH (aq) layer. The structures of compounds ( 1 – 8 ) are shown in Figure 1 .…”

Total Synthesis of (±)‐Phyllantidine: Development and Mechanistic Evaluation of a Ring Expansion for Installation of Embedded Nitrogen‐Oxygen Bonds

“…Its enantiomer, (+)‐phyllantidine ( 1 ), was isolated in 1992 from the leaves of Breynia coronata . Phyllantidine possesses a unique oxazabicyclo[3.3.1]nonane structure and exhibits leishmanicidal activity and anti‐inflammatory properties . Interestingly, Flueggeacosine B ( 11 ), a heterodimer of phyllantidine ( 1 ) and a novel securinega alkaloid fragment containing a azabicyclo[3.2.1]octane system, was isolated recently in 2018 from the roots of Flueggea suffruticosa and displays potent neuronal differentiation activity …”