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Loganin

$78

  • Brand : BIOFRON

  • Catalogue Number : BF-L1003

  • Specification : 98%

  • CAS number : 18524-94-2

  • Formula : C17H26O10

  • Molecular Weight : 390.38

  • PUBCHEM ID : 87691

  • Volume : 20mg

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Catalogue Number

BF-L1003

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

390.38

Appearance

White crystalline powder

Botanical Source

Lamiophlomis rotata,Dipsacus asper,Gentiana scabra,Cornus officinalis,Eucommia ulmoides

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1C(CC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O

Synonyms

7-HYDROXY-6-DESOXYVERBENALIN/(1S,4aS,6S,7R,7aS)-1-(β-D-Glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate de methyle/Loganoside/Cuchiloside/Cyclopenta[c]pyran-4-carboxylic acid, 1-(β-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-, methyl ester, (1S,4aS,6S,7R,7aS)-/Methyl (1S,4aS,6S,7R,7aS)-1-(β-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate/LOGANINE/Loganin/(1S,4aS,6S,7R,7aS)-6-Hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate de methyle/loganic acid methyl ester/Methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate/1-(b-D-Glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic Acid Methyl Ester/Methyl-(1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylat/Loganin, loganoside/Meliatin

IUPAC Name

methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

Density

1.5±0.1 g/cm3

Solubility

Methanol; Water

Flash Point

217.9±25.0 °C

Boiling Point

608.8±55.0 °C at 760 mmHg

Melting Point

222°C

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:18524-94-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30288860

Abstract

Neuroinflammation is closely related with the pathogenesis and progress of neurodegenerative diseases including Alzheimer’s disease (AD). Loganin, an iridoid glycoside obtained from traditional Chinese medicine Cornus officinalis, has properties of inhibiting inflammation and improving memory. The present study was aimed to investigate effects of loganin on Aβ-induced inflammation and to explore the underlying mechanisms. BV-2 microglia cells were stimulated with 10 µM Aβ1-42 for 24 h to induce inflammatory damage. According to results of CCK-8 assay, the doses of loganin in present work were 10 and 30 µM. We found that treatment with loganin could inhibit Aβ1-42 -induced microglia activation. Furthermore, loganin treatment prevented the over-production of Tumor necrosis factor-α (TNF-α), Interleukin-6 (IL-6), Macrophage Chemotactic Protein 1(MCP-1), Nitric oxide (NO), Prostaglandin E2 (PGE2) and the up-regulation of inducible nitric oxide synthase (iNOS) and Cyclooxygenase 2 (COX-2) in Aβ1-42 -stimulated BV-2 cells. Results from Western blots demonstrated that loganin inhibited Aβ1-42 -induced elevation in Toll-like receptor 4 (TLR4), Myeloid Differentiation Factor 88 (MyD88) and TNF receptor-associated factor 6 (TRAF6). Loganin treatment also attenuated the increased phosphorylation level of IRAK4 caused by Aβ1-42 . Additionally, loganin alleviated nuclear translocation of NF-κB p65 subunit in Aβ1-42 -stimulated BV-2 cells, and this phenomenon could be reversed by TLR4 agonist LPS. Further, the anti-inflammatory effects of loganin were attenuated when TLR4 signaling pathway was re-activated by LPS. Taken together, our data indicated that loganin could attenuate inflammatory response induced by Aβ in BV-2 microglia cells, partially through deactivating the TLR4/TRAF6/NF-κB axis.

KEYWORDS

Alzheimer's disease; Loganin; NF-κB; TLR4; TRAF6; inflammation.

Title

Loganin Prevents BV-2 Microglia Cells From Aβ 1-42 -Induced Inflammation via Regulating TLR4/TRAF6/NF-κB Axis

Author

Yong Cui 1, Yanjie Wang 2, Danyu Zhao 2, Xiaofan Feng 2, Lin Zhang 2, Chun Liu 2

Publish date

2020 Jan 30;

PMID

29975123

Abstract

Behavioral disturbances are observed in most patients suffering from diabetes. According to some evidence, pro-inflammatory cytokines have a key role both in diabetes and behavioral disorders, such as anxiety and depression. In this study, the effect of chronic administration of loganin, as a bioflavonoid, was investigated on pro-inflammatory cytokines and depression- and anxiety-like behaviors in streptozotocin-induced diabetes in male Wistar rats. Blood levels of interleukin-6 (IL-6) and tumor necrosis factor-alpha (TNF-α) were assessed by enzyme-linked immunosorbent assay method. Depression- and anxiety-like behaviors were evaluated by forced swimming test (FST), elevated plus maze (EPM), and open field test (OFT), respectively. Body weight was also measured before the interventions and after the experiments in all groups. Our findings show that loganin-treated animals had significantly lower serum concentrations of IL-6 and TNF-α compared with the diabetic group. In the EPM test, loganin treatment significantly increased the percentage of the open arm time and open arm entries. Moreover, loganin treatment significantly decreased the grooming time and restored distance traveled and center crossing in the OFT. However, it decreased immobility time in the FST. Loganin treatment also significantly restored body weight gain and attenuated blood glucose changes in the diabetic rats. These results indicate that loganin possibly alleviates depression- and anxiety-like behaviors associated with diabetes through lowering the blood glucose and pro-inflammatory cytokine levels. More research is required to show the exact mechanism of antidepressant and anxiolytic effects of loganin in diabetes.

KEYWORDS

IL-6; TNF-α; anxiety; depression; diabetes; loganin.

Title

Impact of Loganin on Pro-Inflammatory Cytokines and Depression- And Anxiety-Like Behaviors in Male Diabetic Rats

Author

M Rajabi 1, G Mohaddes 1, F Farajdokht 1, S Nayebi Rad 2, M Mesgari 3, S Babri 1

Publish date

2018 Jun 1

PMID

29855187

Abstract

Behavioral disturbances are observed in most patients suffering from diabetes. According to some evidence, pro-inflammatory cytokines have a key role both in diabetes and behavioral disorders, such as anxiety and depression. In this study, the effect of chronic administration of loganin, as a bioflavonoid, was investigated on pro-inflammatory cytokines and depression- and anxiety-like behaviors in streptozotocin-induced diabetes in male Wistar rats. Blood levels of interleukin-6 (IL-6) and tumor necrosis factor-alpha (TNF-α) were assessed by enzyme-linked immunosorbent assay method. Depression- and anxiety-like behaviors were evaluated by forced swimming test (FST), elevated plus maze (EPM), and open field test (OFT), respectively. Body weight was also measured before the interventions and after the experiments in all groups. Our findings show that loganin-treated animals had significantly lower serum concentrations of IL-6 and TNF-α compared with the diabetic group. In the EPM test, loganin treatment significantly increased the percentage of the open arm time and open arm entries. Moreover, loganin treatment significantly decreased the grooming time and restored distance traveled and center crossing in the OFT. However, it decreased immobility time in the FST. Loganin treatment also significantly restored body weight gain and attenuated blood glucose changes in the diabetic rats. These results indicate that loganin possibly alleviates depression- and anxiety-like behaviors associated with diabetes through lowering the blood glucose and pro-inflammatory cytokine levels. More research is required to show the exact mechanism of antidepressant and anxiolytic effects of loganin in diabetes.

KEYWORDS

IL-6; TNF-α; anxiety; depression; diabetes; loganin.

Title

Impact of Loganin on Pro-Inflammatory Cytokines and Depression- And Anxiety-Like Behaviors in Male Diabetic Rats

Author

M Rajabi 1, G Mohaddes 1, F Farajdokht 1, S Nayebi Rad 2, M Mesgari 3, S Babri 1

Publish date

2018 Sep 1


Description :

Loganin, a major iridoid glycoside obtained from Corni fructus, has been shown to have anti-inflammatory and anti-shock effects. Loganin exhibits an anti-inflammatory effect in cases of AP and its pulmonary complications through inhibition of NF-κB activation.