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Open AccessArticle

Constituents of the Stem Bark of Symphonia globulifera Linn. f. with Antileishmanial and Antibacterial Activities

by Ruland Tchuinkeu Nguengang, Billy Toussie Tchegnitegni, Eric Carly Nono Nono, Georges Bellier Tabekoueng, Yannick Stéphane Fotsing Fongang, Jean Jules Kezetas Bankeu, Jean Rodolphe Chouna, Céline Nguefeu Nkenfou, Fabrice Boyom Fekam, Norbert Sewald and Bruno Ndjakou Lenta

Molecules 2023, 28(6), 2473; https://doi.org/10.3390/molecules28062473 - 8 Mar 2023

Cited by 5 | Viewed by 2827

Abstract

The chemical investigation of the n-hexane fraction from the methanol extract of the stem bark of Symphonia globulifera Linn f., which displayed good in vitro activity against Leishmania donovani NR-48822 promastigotes (IC₅₀ 43.11 µg/mL), led to the isolation of three previously unreported polyprenylated benzophenones, guttiferone U (1), V (2)/W (3), and a new tocotrienol derivative named globuliferanol (4), along with 11 known compounds (5–15). Their structures were elucidated based on their NMR and MS data. Some isolated compounds were assessed for both their antileishmanial and cytotoxic activities against L. donovani and Vero cells, respectively. Guttiferone K (5) exhibited the best potency (IC₅₀ 3.30 μg/mL), but with low selectivity to Vero cells. The n-hexane fraction and some compounds were also assessed in vitro for their antibacterial activity against seven bacterial strains. All the samples exhibited moderate to potent antibacterial activity (MICs ≤ 15.6 µg/mL) against at least one of the tested strains. Full article

(This article belongs to the Special Issue Biological Activity of Phenolics and Polyphenols in Nature Products)

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17 pages, 6885 KB

Open AccessArticle

Targeting MHC Regulation Using Polycyclic Polyprenylated Acylphloroglucinols Isolated from Garcinia bancana

by Chloé Coste, Nathalie Gérard, Chau Phi Dinh, Antoine Bruguière, Caroline Rouger, Sow Tein Leong, Khalijah Awang, Pascal Richomme, Séverine Derbré and Béatrice Charreau

Biomolecules 2020, 10(9), 1266; https://doi.org/10.3390/biom10091266 - 2 Sep 2020

Cited by 11 | Viewed by 3916

Abstract

Modulation of major histocompatibility complex (MHC) expression using drugs has been proposed to control immunity. Phytochemical investigations on Garcinia species have allowed the isolation of bioactive compounds such as polycyclic polyprenylated acylphloroglucinols (PPAPs). PPAPs such as guttiferone J (1), display anti-inflammatory and immunoregulatory activities while garcinol (4) is a histone acetyltransferases (HAT) p300 inhibitor. This study reports on the isolation, identification and biological characterization of two other PPAPs, i.e., xanthochymol (2) and guttiferone F (3) from Garcinia bancana, sharing structural analogy with guttiferone J (1) and garcinol (4). We show that PPAPs 1–4 efficiently downregulated the expression of several MHC molecules (HLA-class I, -class II, MICA/B and HLA-E) at the surface of human primary endothelial cells upon inflammation. Mechanistically, PPAPs 1–4 reduce MHC proteins by decreasing the expression and phosphorylation of the transcription factor STAT1 involved in MHC upregulation mediated by IFN-γ. Loss of STAT1 activity results from inhibition of HAT CBP/p300 activity reflected by a hypoacetylation state. The binding interactions to p300 were confirmed through molecular docking. Loss of STAT1 impairs the expression of CIITA and GATA2 but also TAP1 and Tapasin required for peptide loading and transport of MHC. Overall, we identified new PPAPs issued from Garcinia bancana with potential immunoregulatory properties. Full article

(This article belongs to the Section Natural and Bio-derived Molecules)

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7 pages, 885 KB

Open AccessCommunication

Dalbergia ecastaphyllum (L.) Taub. and Symphonia globulifera L.f.: The Botanical Sources of Isoflavonoids and Benzophenones in Brazilian Red Propolis

by Gari Vidal Ccana-Ccapatinta, Jennyfer Andrea Aldana Mejía, Matheus Hikaru Tanimoto, Milton Groppo, Jean Carlos Andrade Sarmento de Carvalho and Jairo Kenupp Bastos

Molecules 2020, 25(9), 2060; https://doi.org/10.3390/molecules25092060 - 28 Apr 2020

Cited by 70 | Viewed by 5751

Abstract

The Brazilian red propolis (BRP) constitutes an important commercial asset for northeast Brazilian beekeepers. The role of Dalbergia ecastaphyllum (L.) Taub. (Fabaceae) as the main botanical source of this propolis has been previously confirmed. However, in addition to isoflavonoids and other phenolics, which are present in the resin of D. ecastaphyllum, samples of BRP are reported to contain substantial amounts of polyprenylated benzophenones, whose botanical source was unknown. Therefore, field surveys, phytochemical and chromatographic analyses were undertaken to confirm the botanical sources of the red propolis produced in apiaries located in Canavieiras, Bahia, Brazil. The results confirmed D. ecastaphyllum as the botanical source of liquiritigenin (1), isoliquiritigenin (2), formononetin (3), vestitol (4), neovestitol (5), medicarpin (6), and 7-O-neovestitol (7), while Symphonia globulifera L.f. (Clusiaceae) is herein reported for the first time as the botanical source of polyprenylated benzophenones, mainly guttiferone E (8) and oblongifolin B (9), as well as the triterpenoids β-amyrin (10) and glutinol (11). The chemotaxonomic and economic significance of the occurrence of polyprenylated benzophenones in red propolis is discussed. Full article

(This article belongs to the Special Issue Special Issue in Honor of Professor James D. McChesney on the Occasion of his 80th Birthday)

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10 pages, 68 KB

Open AccessArticle

Leishmanicidal and Cholinesterase Inhibiting Activities of Phenolic Compounds from Allanblackia monticola and Symphonia globulifera

by Bruno Ndjakou Lenta, Catherine Vonthron-Sénécheau, Bernard Weniger, Krishna Prasad Devkota, Joseph Ngoupayo, Marcel Kaiser, Qamar Naz, Muhammad Iqbal Choudhary, Etienne Tsamo and Norbert Sewald

Molecules 2007, 12(8), 1548-1557; https://doi.org/10.3390/12081548 - 20 Jul 2007

Cited by 96 | Viewed by 15058

Abstract

In a preliminary antiprotozoal screening of several Clusiaceae species, the methanolic extracts of Allanblackia monticola and Symphonia globulifera showed high in vitro leishmanicidal activity. Further bioguided phytochemical investigation led to the isolation of four benzophenones: guttiferone A (1), garcinol (2), cambogin (3) and guttiferone F (4), along with three xanthones: allanxanthone A (5), xanthone V₁ (6) and globulixanthone C (7) as active constituents. Compounds 1 and 6 were isolated from S. globulifera leaves, while compounds 2-5 were obtained from A. monticola fruits. Guttiferone A (1) and F (4) showed particulary strong leishmanicidal activity in vitro, with IC₅₀ values (0.2 μM and 0.16 μM, respectively) comparable to that of the reference compound, miltefosine (0.46 μM). Although the leishmanicidal activity is promising, the cytotoxicity profile of these compounds prevent at this state further in vivo biological evaluation. In addition, all the isolated compounds were tested in vitro for their anticholinesterase properties. The four benzophenones showed potent anticholinesterase properties towards acetylcholinesterase (AChE) and butylcholinesterase (AChE). For AChE, the IC₅₀ value (0.66 μM) of garcinol (2) was almost equal to that of the reference compound galanthamine (0.50 μM). Furthermore, guttiferone A (1) and guttiferone F (4) (IC₅₀ = 2.77 and 3.50 μM, respectively) were more active than galanthamine (IC₅₀ = 8.5) against BChE. Full article

(This article belongs to the Special Issue Phenolics and Polyphenolics)

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