ChemInform Abstract: New Dimeric Flavans from Gambir, an Extract of Uncaria gambir

Taniguchi, Shoko; Kuroda, Kayo; Yoshikado, Naomi; Doi, Kou‐Ichi; Tanabe, Masahiro; Shibata, Takashi; Yoshida, Takashi; Hatano, Tsutomu

doi:10.1002/chin.200823201

Cited by 2 publications

(1 citation statement)

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“…From the HMBC spectrum, correlations were observed between H-4 ( 3.18) with C-8 ( 102.4), C-7 ( 156.0) and C-3 ( 133.1) confirming the C-4 C-8 bond. Moreover, comparison of the high chemical shift values of C-4a and C-8 at C 99.9 and 102.4 with literature data (Malan et al 1996; Messanga et al 1998; Mello de et al 1999;Taniguchi et al 2007;Ragab et al 2013;Wang et al 2015) and referring to mass spectrometry (HR-ESI-MS and LC-MS) of 6 ( Figure S15; S16) indicated the presence of a C-O-C linkage, which are characterized by the existence of a doubly interflavanoid linkage. This doubly linked structure was also supported through HMBC spectrum.…”

Section: Resultsmentioning

confidence: 54%

A new procyanidin B from Campylospermum zenkeri (Ochnaceae) and antiplasmodial activity of two derivatives of (±)-serotobenine

Nyemeck

Bikobo

Zintchem

et al. 2017

Natural Product Research

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Phytochemical investigation of the stem bark of Campylospermum zenkeri led to the isolation of five known compounds: (Z,Z)-9,12-octadecadienoic acid (1), serotobenine (2), agathisflavone (3), lophirone A (4) and lophirone F (5), together with a new derivative of procyanidin B, a catechin dimer named zenkerinol (6). Serotobenine (2) is structurally related to decursivine which shows moderate activity against D6 and W2 strains of Plasmodium falciparum. For a better understanding of structure-activity relationships, three new semisynthetic derivatives of serotobenine (2) have been prepared. These are: serotobenine monopropionate (2a), serotobenine monopivalate (2b) and serotobenine cyclohexyl ether (2c) respectively. Two of them (2a) and (2b), were evaluated for their antiplasmodial activity against P. falciparum 3D7 strain in a parasite lactate-dehydrogenase (pLDH) assay. Compound 2b was more active than compound 2a based on their IC 50 values (36.6 and 123 μM, respectively).

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Section: Resultsmentioning

confidence: 54%

A new procyanidin B from Campylospermum zenkeri (Ochnaceae) and antiplasmodial activity of two derivatives of (±)-serotobenine

Nyemeck

Bikobo

Zintchem

et al. 2017

Natural Product Research

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The Potency of Catechin from Gambir (Uncaria gambir Roxb.) as a Natural Inhibitor of MurA (1UAE) Enzyme: In vitro and In silico studies

Riyana

Huspa

Satari

et al. 2020

LDDD

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Background: Currently, the infectious disease caused by pathogenic and resistant bacteria is more challenging for antibacterial drug discovery. The discovery of new antibacterial agents developed in many mechanisms includes disruption of the bacterial cell wall formations. The MurA is a key enzyme contributing to the first step of bacterial peptidoglycan biosynthesis and is therefore proposed as an effective bactericidal target. Objective: The purpose of this research is to identify antibacterial compounds from U. gambir Roxb and to predict the potential inhibitory activities against murA enzyme by in silico study. Materials and Methods: Investigation and discovery of new inhibitors of MurA enzyme were conducted on the medicinal plant of Gambir (Uncaria gambir Roxb) and those reported contained antibacterial. The antibacterial compounds were isolated by combinations of chromatography methods guided by antibacterial activity against bacteria of E. faecalis, S. mutans, and S. sanguinis. The structures of active compounds were characterized by spectroscopic methods, and the antibacterial activity was evaluated by the microdilution method (in vitro) combined with molecular docking of the MurA enzyme (in silico). Results: The antibacterial flavonoid of catechin was isolated from U. gambir Roxb with MIC values of 6250 and 12500 ppm, respectively against S. sanguinis and E. faecalis. The in silico study showed that catechin has binding affinity -8.5 Kcal/mol to MurA those higher than fosfomycin as a positive control. Conclusions: The catechin is predicted to have potential as a new natural inhibitor of the MurA enzyme to inhibit bacterial cell wall biosynthesis.

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ChemInform Abstract: New Dimeric Flavans from Gambir, an Extract of Uncaria gambir

Cited by 2 publications

References 1 publication

A new procyanidin B from Campylospermum zenkeri (Ochnaceae) and antiplasmodial activity of two derivatives of (±)-serotobenine

A new procyanidin B from Campylospermum zenkeri (Ochnaceae) and antiplasmodial activity of two derivatives of (±)-serotobenine

The Potency of Catechin from Gambir (Uncaria gambir Roxb.) as a Natural Inhibitor of MurA (1UAE) Enzyme: In vitro and In silico studies

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