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Bengenin

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-B2009

  • Specification : 98%

  • CAS number : 477-90-7

  • Formula : C14H16O9

  • Molecular Weight : 328.27

  • PUBCHEM ID : 66065

  • Volume : 20mg

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Catalogue Number

BF-B2009

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

328.27

Appearance

White crystalline powder

Botanical Source

Neopicrorhiza scrophulariiflora,Cimicifuga foetida,Caesalpinia millettii,Bergenia purpurascens,Chloranthus multistachys

Structure Type

Others

Category

Standards;Natural Pytochemical;API

SMILES

COC1=C(C=C2C(=C1O)C3C(C(C(C(O3)CO)O)O)OC2=O)O

Synonyms

Vakerin/Ai Cha Su/Bergenitol/Bergenit/Peltophorin/CORYLOPSIN/(+)-Bergenin/3,4,8,10-Tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one/4-Methoxy-2-[tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)pyran-2-yl]-a-resorcylic Acid d-Lactone/Pyrano[3,2-c][2]benzopyran-6(2H)-one, 3,4,4a,10b-tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-/3,4,4a,10b-Tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxypyrano[3,2-c][2]benzopyran-6(2H)-one/BERGENIN/Bergenin:Pyrano[3,2-c][2]benzopyran-6(2H)-one,3,4,4a,10b-tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-, [2R-(2,3,4,4a, 10b)]-,/CUSCUTIN/Ardisic Acid B

IUPAC Name

(2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one

Density

1.6±0.1 g/cm3

Solubility

Methanol

Flash Point

250.7±25.0 °C

Boiling Point

658.9±55.0 °C at 760 mmHg

Melting Point

237-240 °C(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2940000000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:477-90-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31070542

Abstract

CONTEXT:
Bergenin, isolated from the herb of Bergenia purpurascens (Hook. f. et Thoms.) Engl., has anti-inflammatory, antitussive, and wound healing activities. However, whether bergenin affects the activity of human liver cytochrome P450 (CYP) enzymes remains unclear.

MATERIALS AND METHODS:
In this study, the inhibitory effects of bergenin (100 μM) on the eight human liver CYP isoforms (i.e., 1A2, 3A4, 2A6, 2E1, 2D6, 2C9, 2C19 and 2C8) were investigated, enzyme kinetics and time-dependent inhibition studies were also performed in vitro using human liver microsomes (HLMs).

RESULTS:
The results showed that bergenin inhibited the activity of CYP3A4, 2E1 and 2C9, with IC50 values of 14.39, 22.83 and 15.11 μM, respectively, but other CYP isoforms were not affected. Enzyme kinetic studies showed that bergenin was not only a non-competitive inhibitor of CYP3A4, but also a competitive inhibitor of CYP2E1 and 2C9, with Ki values of 7.71, 11.39 and 8.89 μM, respectively. In addition, bergenin is a time-dependent inhibitor for CYP3A4 with Kinact/KI value of 0.025/3.50 μM-1 min-1.

DISCUSSION AND CONCLUSIONS:
The in vitro studies of bergenin with CYP isoforms indicate that bergenin has the potential to cause pharmacokinetic drug interactions with other co-administered drugs metabolized by CYP3A4, 2E1 and 2C9. Further clinical studies are needed to evaluate the significance of this interaction.

KEYWORDS

CYP2C9; CYP2E1; CYP3A4; herb-drug interaction

Title

In vitro inhibitory effects of bergenin on human liver cytochrome P450 enzymes.

Author

Dong G1, Zhou Y1, Song X1.

Publish date

2018 Dec;

PMID

30975902

Abstract

The widespread availability and use of modern synthetic therapeutic agents have led to a massive decline in ethnomedical therapies. However, these synthetic agents often possess toxicity leading to various adverse effects. For instance, anti-tubercular treatment (ATT) is toxic, lengthy, and severely impairs host immunity, resulting in posttreatment vulnerability to reinfection and reactivation of tuberculosis (TB). Incomplete ATT enhances the risk for the generation of multidrug- or extensively drug-resistant (MDR or XDR, respectively) variants of Mycobacterium tuberculosis (M. tb), the TB-causing microbe. Therefore, a new therapeutic approach that minimizes these risks is urgently needed to combat this deadly disease and prevent future TB epidemics. Previously, we have shown that the phytochemical bergenin induces T helper 1 (Th1)- and Th17 cell-based protective immune responses and potently inhibits mycobacterial growth in a murine model of M. tb infection, suggesting bergenin as a potential adjunct agent to TB therapy. Here, we combined ATT therapy with bergenin and found that this combination reduces immune impairment and the length of treatment in mice. We observed that co-treatment with the anti-TB drug isoniazid and bergenin produces additive effects and significantly reduces bacterial loads compared with isoniazid treatment alone. The bergenin co-treatment also reduced isoniazid-induced immune impairment; promoted long-lasting, antigen-specific central memory T cell responses; and acted as a self-propelled vaccine. Of note, bergenin treatment significantly reduced the bacterial burden of a multidrug-resistant TB strain. These observations suggest that bergenin is a potent immunomodulatory agent that could be further explored as a potential adjunct to TB therapy.

© 2019 Kumar et al.

KEYWORDS

Mycobacterium tuberculosis; T cells; T helper cells; adjunct therapy; bergenin; cytokine; drug resistance; immunity; immunotherapy; infectious disease; isoniazid; memory cells; multidrug resistance; natural product

Title

The phytochemical bergenin as an adjunct immunotherapy for tuberculosis in mice.

Author

Kumar S1, Sharma C1, Kaushik SR1, Kulshreshtha A2, Chaturvedi S1, Nanda RK1, Bhaskar A3, Chattopadhyay D4, Das G5, Dwivedi VP6.

Publish date

2019 May 24

PMID

30845642

Abstract

Endopleura uchi (Huber) Cuatrec (Humiriaceae), known as uxi or uxi-amarelo in Brazil, is an endemic tree of the Amazon forest. In traditional medicine, its stem bark is used to treat a variety of health disorders, including cancer, diabetes, arthritis, uterine inflammation, and gynecological infections. According to HPLC analysis, the main constituent of the bark extract is the polyphenol bergenin. In the current study, we demonstrate by in vitro and in vivo experiments the antioxidant potential of a water extract from the stem bark of E. uchi. When tested in the model organism Caenorhabditis elegans, the extract enhanced stress resistance via the DAF-16/FOXO pathway. Additionally, the extract promoted an increase in the lifespan of the worms independent from caloric restriction. It also attenuated the age-related muscle function decline and formation of polyQ40 plaques, as a model for Huntington’s disease. Thus, these data support anti-aging and anti-oxidant properties of E. uchi, which has not yet been described. More studies are needed to assess the real benefits of E. uchi bark for human health and its toxicological profile.

KEYWORDS

Caenorhabditis elegans; Endopleura uchi; Huntington; antioxidants; bergenin; lifespan; stress resistance; uxi

Title

Bark Extract of the Amazonian Tree Endopleura uchi (Humiriaceae) Extends Lifespan and Enhances Stress Resistance in Caenorhabditis elegans.

Author

Peixoto H1, Roxo M2, Silva E3, Valente K4, Braun M5, Wang X6, Wink M7.

Publish date

2019 Mar 6;


Description :

Bergenin, a polyphenol, is a potent antinarcotic agent with antioxidant action. IC50 value: < 2.5 μM (antiplasmodial) [3]Target:In vitro: The naloxone-precipitated withdrawal symptom (jumping frequency) was significantly ameliorated (50% of control group) by administration of bergenin (20 mg/kg) in morphine-treated mice. Furthermore, morphine-induced down-regulation of glutathione (GSH) contents was reversed by bergenin administration in the frontal cortex and liver [2].In vivo: Bergenin attenuated inflammatory cell infiltration and decreased the concentration of NO, TNF-α, IL-1β, and IL-6, which were increased in LPS-induced mouse mastitis [1].