Enantioselctive Syntheses of Sulfur Analogues of Flavan-3-Ols

Sharma, Pradeep K.; He, Min; Jurayj, Jurjus; Gou, Da-Ming; Lombardy, Richard; Romanczy, Leo J.; Schroeter, Hagen

doi:10.3390/molecules15085595

Cited by 20 publications

(8 citation statements)

References 46 publications

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“…The infrared (IR) (Figure ), 1 H and 13 C nuclear magnetic resonance (NMR) spectra (Table , Figures –) allied to optical rotations ([α]

_{normalD}^{27}

–43.5 ( c 0.02, MeOH) and [α]

_{normalD}^{27}

–16.3 ( c 0.02, Me 2 CO)) were similar to those published in the literature, indicating a 2 S ,3 R absolute configuration, and are consistent with the structure of (–)‐catechin (Figure ).…”

Section: Resultssupporting

confidence: 87%

Antifungal and cytotoxicity activities of Banisteriopsis argyrophylla leaves

Oliveira

Silva

Martins

et al. 2018

Journal of Pharmacy and Pharmacology

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Objectives This work aimed to evaluate the antifungal and cytotoxic activity of the EtOH extract and fractions of Banisteriopsis argyrophylla leaves, and to perform the identification of these bioactive metabolites. Methods The EtOAc fraction (EAF) obtained from the ethanolic extract of B. argyrophylla leaves showed better antifungal potential against Candida spp. In this fraction, ten flavonoids have been identified by UHPLC‐ESI‐MSn. Then, EAF was submitted to column chromatography to give four new fractions (A1–A4). The cytotoxicity was determined against Vero cells. Key findings The EAF showed better antifungal potential against Candida spp. with minimum inhibitory concentrations (MICs) between 31.25 and 93.75 μg/ml. The (–)‐catechin (fraction A1) showed a MIC of 2.83 μg/ml against Candida glabrata. Fractions A2, A3 and A4 were rich in quercetins and kaempferols and showed good inhibitory concentrations (5.86–46.87 μg/ml) against C. albicans, C. glabrata and C. tropicalis. Conclusions The EtOH extract, fractions and the isolated (–)‐catechin showed lower toxicity to Vero cells than cisplatin, used as a positive control. Thus, the leaves of B. argyrophylla are a promising source of antifungal agents.

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“…The infrared (IR) (Figure ), 1 H and 13 C nuclear magnetic resonance (NMR) spectra (Table , Figures –) allied to optical rotations ([α]

_{normalD}^{27}

–43.5 ( c 0.02, MeOH) and [α]

_{normalD}^{27}

–16.3 ( c 0.02, Me 2 CO)) were similar to those published in the literature, indicating a 2 S ,3 R absolute configuration, and are consistent with the structure of (–)‐catechin (Figure ).…”

Section: Resultssupporting

confidence: 87%

Antifungal and cytotoxicity activities of Banisteriopsis argyrophylla leaves

Oliveira

Silva

Martins

et al. 2018

Journal of Pharmacy and Pharmacology

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“…The experimental rotation was an average of +69.25 ( n = 4) concluding that this compound is (+)-catechin. Previous published data on (+)-catechin reports an optical rotation of +56.60 [ 15 ].…”

Section: Resultsmentioning

confidence: 99%

The Antiacetylcholinesterase and Antileishmanial Activities ofCanarium patentinerviumMiq.

Rajagopal

Adhikari

Debnath

et al. 2014

BioMed Research International

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In continuation of our natural and medicinal research programme on tropical rainforest plants, a bioassay guided fractionation of ethanolic extract of leaves of Canarium patentinervium Miq. (Burseraceae Kunth.) led to the isolation of scopoletin (1), scoparone (2), (+)-catechin (3), vomifoliol (4), lioxin (5), and syringic acid (6). All the compounds exhibited antiacetylcholinesterase activity with syringic acid, a phenolic acid exhibiting good AChE inhibition (IC50 29.53 ± 0.19 μg/mL). All compounds displayed moderate antileishmanial activity with scopoletin having the highest antileishmanial activity (IC50 163.30 ± 0.32 μg/mL). Given the aforementioned evidence, it is tempting to speculate that Canarium patentinervium Miq. represents an exciting scaffold from which to develop leads for treatment of neurodegenerative and parasitic diseases.

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“…Epicatechin metabolites: 3′‐ O ‐methyl(−)‐epicatechin (3′MEC), 4′‐ O ‐methyl(−)‐epicatechin (4′MEC), (−)‐epicatechin‐7‐β‐ d ‐glucuronide (EC7G), 4′‐ O ‐methyl(−)‐epicatechin‐7‐β‐ d ‐glucuronide (4′MEC7G), and (−)epicatechin‐4′‐sulfate (EC4′S) were gifted by Mars Incorporated (McLean, VA, USA) (Supporting Information Fig. 1) . Solutions of catechin and epicatechin as well as of their conjugates were obtained by dissolving in ethanol 50% in double distilled water.…”

Section: Methodsmentioning

confidence: 99%