Antiplasmodial activity of some phenolic compounds from Cameroonians Allanblackia

Abstract

Background: Plasmodium falciparum, one of the causative agents of malaria, has high adaptability through mutation and is resistant to many types of anti-malarial drugs. This study presents an in vitro assessment of the antiplasmodial activity of some phenolic compounds isolated from plants of the genus Allanblackia. Methods: Tests were performed on well plates filled with a fixed parasitized erythrocytes volume. Compounds to be tested were then added in wells. After incubation, tritiated hypoxanthine is added and the plates were returned to the incubator. After thawing, the nucleic acids are collected. Inhibitory Concentration 50 (IC50) was determined by linear interpolation. Results: From Allanblackia floribunda, have been isolated and characterized 1,7-dihydroxyxanthone 1, macluraxanthone 4, morelloflavone 9, Volkensiflavone 10 and morelloflavone 7-O-glucoside 11; from Allanblackia monticola, α-mangosine 2, rubraxanthone 3, allaxanthone C 5, norcowanine 6 , tovophiline A 7, allaxanthone B 8 and from Allanblackia gabonensis, 1,7-dihydroxyxanthone 1. Six of them were evaluated for their antimalarial properties. The most active compound, macluraxanthone, presented a very interesting activity, with an IC50 of 0.36 and 0.27 µg/mL with the F32 and FcM29 strains respectively. Conclusion: This work confirms that species of Allanblackia genus are medicinally important plants containing many biologically active compounds that can be used effectively as antiplasmodial.

Two xanthones and two rotameric (3⟶8) biflavonoids from the Cameroonian medicinal plant Allanblackia floribunda Oliv. (Guttiferae)

“…The 1 H NMR spectral data displayed a smaller J value of 7.6 Hz between protons H-2 and H-3 suggesting their monoaxial (cis) configuration and thus the absolute configuration in compound 4 could be (2R,3R) or (2S,3S). 22 Furthermore, Gaffield 21 reported that, in the CD spectrum The known compounds were identified as volkensiflavone (5) [24][25][26] , morelloflavone (6), 2,4,15,27 volkensiflavone-7-O--glucopyranoside (7), 17 morelloflavone-7-O--glucopyranoside (8), 2,17 (-)-catechin (9), 28 1,5-dihydroxyxanthone (10), 5,9 1,7-dihydroxyxanthone (11), 2,3,29 allanxanthone A (12), 5 6-deoxyisojacareubin (13), 3 hydrocotoin (14), 4 betulinic acid (15) 30 an inseparable mixture of -sitosterol and stigmasterol 31 and, an inseparable mixture of -sitosteryland stigmasteryl-3-O--glucopyranosides. 5 The absolute configurations of compounds 5-8 were determined as (2R,3S), (2R,3S), (2S,3R) and (2S,3R) respectively.…”

In vitro antiplasmodial activity of Withania frutescens —Solanaceae

“…Phenolic compounds including flavonoid are one of the most important classes of antiplasmodial compounds [20]. The ethyl acetate fraction possess high phenolic and flavonoid content (254.8 ± 2.9 mg CAE/g dry fraction and 122 ± 0.77 mg CE/g dry fraction, respectively) which may be responsible for its antiplasmodial activity.…”

Flavonoids as efficient scaffolds: Recent trends for malaria, leishmaniasis, Chagas disease, and dengue

“…Based on these considerations, compounds 10 (IC 50 : 0.65 μM; SI: 77; KB3‐1 cells), 11 (IC 50 : 0.16 μM; SI: >900; KB3‐1 cells), and 12 (IC 50 : 0.21 μM ; >700; KB3‐1 cells; Konziase, ) can be considered as hit compounds against P. falciparum FCR‐3, the cycloguanil‐resistant strain. Antimalarial hit compounds against the chloroquine resistant strains included compounds 8 (IC 50 : 0.95 μg/ml; Azebaze et al, ); 34 (IC 50 : 2.94 μM; Ganesh et al, ); 62 (IC 50 : 1.7 μM); 63 (IC 50 : 2.1 μM; De Monbrison et al, ); and 77 (IC 50 : 0.08 μg/ml; SI: 375 MRC‐5 cells; Konziase, ). In cutaneous leishmaniasis, the hit compounds included compounds 30 (IC 50 : 4.3 μM; SI: 18.3, macrophage cells; Fonseca‐Silva et al, ); 34 (IC 50 : 0.7 μM; SI: 10, macrophage cells; Montrieux et al, ); 92 (IC 50 : 0.2 μM; SI: 22, J774.A1 cells; Rizk et al, ); 95 (IC 50 : 8.1 μM; SI: 24.6, macrophage cells); and 96 (IC 50 : 3.2 μM; SI: 39.6, macrophage cells; Lage et al, ).…”

“…From the database searches, 830 (“malaria and flavonoids”: 540; “Chagas disease and flavonoids”: 60; “leishmaniasis and flavonoids”: 124; “dengue and flavonoids”: 106) potentially relevant records were identified, from which 737 were excluded after screening the titles or abstracts. The full reports of 93 articles were acquired: 83 studies related to natural flavonoids (Adinehbeigi, Razi Jalali, Shahriari, & Bahrami, ; Allard et al, ; Anusuya & Gromiha, ; Anusuya & Gromiha, ; Assis et al, ; Azebaze et al, ; Beer et al, ; Cabanillas et al, ; Castro, Barrios, Chinchilla, & Guerrero, ; Cheema et al, ; Cornelio et al, ; Coulerie et al, ; Cunha‐Rodrigues et al, ; Da Rocha et al, ; Da Silva, Maquiaveli, & Magalhães, ; De Monbrison et al, ; De Sousa et al, ; De Sousa et al, ; Dos Reis, Manjolin, Maquiaveli, Santos‐Filho, & da Silva, ; Ezenyi et al, ; Fonseca‐Silva, Inacio, Canto‐Cavalheiro, & Almeida‐Amaral, ; Fonseca‐Silva, Inacio, Canto‐Cavalheiro, Menna‐Barreto, & Almeida‐Amaral, ; Frabasile et al, ; Freitas et al, ; Ganesh et al, ; Gontijo et al, ; Grael, Albuquerque, & Lopes, ; Grecco et al, ; Güida et al, ; Heh et al, ; Houël et al, ; Ichino et al, ; Ijaz, Ahmad, Ahmad, ul Haq, & Wang, ; Inacio, Gervazoni, Canto‐Cavalheiro, & Almeida‐Amaral, ; Ismail & Jusoh, ; Jasmeen et al, ; Jin et al, ; Kapingu et al, ; Kiat et al, ; Kimmel et al, ; Konziase, ; Kraft et al, ; Kraft et al, ; Lage et al, ; Lage et al, ; Lehane & Saliba, ; Leite et al, ; Lu et al, ; Manjolin, dos Reis, Maquiaveli, Santos‐Filho, & da Silva, ; Marín et al, ; Marín et al, ; Mittra et al, ; Moghaddam et al, ; Montenegro, Gonzalez, Ortega‐Barria, & Luis Cubi...…”

“…In another study, three flavonoids, namely, morelloflavone ( 7 ), volkensiflavone ( 8 ), and morelloflavone 7‐ O ‐glucoside ( 9 ) (isolates of Allanblackia floribunda ) showed inhibitory effects against P. falciparum F32 (IC 50 : 3.36, 1.18, and 8.38 μg/ml, respectively) and P. falciparum FcM29 (IC 50 : 4.80, 0.95, and 23.82 μg/ml, respectively) after 72 hr of incubation. Although 7 , 8 , and 9 afforded appreciable IC 50 values, their cytotoxicity to mammalian cells is yet to be determined (Azebaze et al, ). Konziase () has found that three biflavanones (I‐4′,II‐4′,I‐5,II‐5,I‐7,II‐7‐hexahydroxy‐I‐3,II‐8‐biflavanone [ 10 ]; II‐3,I‐4′,II‐4′,I‐5,II‐5,I‐7,II‐7‐heptahydroxy‐I‐3,II‐8‐biflavanone [ 11 ]; and II‐3, 3′,I‐4′,II‐4′,I‐5,II‐5,I‐7,II‐7‐octahydroxy‐I‐3,II‐8‐biflavanone [ 12 ]; Table S1) isolated from Garcinia kola seeds were active against P .…”