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Gigantol

$576

  • Brand : BIOFRON

  • Catalogue Number : BD-D1230

  • Specification : 98%(HPLC)

  • CAS number : 67884-30-4

  • Formula : C16H18O4

  • Molecular Weight : 274.31

  • PUBCHEM ID : 3085362

  • Volume : 20MG

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Catalogue Number

BD-D1230

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

274.31

Appearance

Off-white crystal

Botanical Source

Cymbidium aloifolium, Dendrobium moscatum and Dendrobium chrysanthum

Structure Type

Category

Standards;Natural Pytochemical;API

SMILES

COC1=C(C=C(C=C1)CCC2=CC(=CC(=C2)OC)O)O

Synonyms

Gigantol

IUPAC Name

5-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxyphenol

Applications

Gigantol is a bibenzyl compound derived from several medicinal orchids. Giganto shows promising therapeutic potential against cancer cells. Gigantol is a novel inhibitor of the Wnt/β-catenin pathway.

Density

1.204±0.06 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

Boiling Point

Melting Point

InChl

InChI=1S/C16H18O4/c1-19-14-8-12(7-13(17)10-14)4-3-11-5-6-16(20-2)15(18)9-11/h5-10,17-18H,3-4H2,1-2H3

InChl Key

SDXKZPQOVUDXIY-UHFFFAOYSA-N

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#:67884-30-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

30844727

Abstract

We previously reported that gigantol extracted from Caulis Dendrobii has significant therapeutic benefits for the treatment of galactosemic cataracts through its ability to inhibit aldose reductase (AR) activity. In this study, we identified the binding sites and structurally characterized the interaction between gigantol and AR, to understand the mechanism (s) of the effects of gigantol on cataracts. Gigantol was found to be protective against diabetic cataracts (DC) in rats induced by streptozotocin. Molecular docking predicted the binding sites between AR and gigantol to be residues Trp111, His110, Tyr48 and Trp20. Mutation of each of these residues led to a significant reduction in AR activity. Cold-spray ionization mass spectrometry measurements showed that the binding of gigantol to AR is oncentration-dependent and that the maximum stoichiometric ratio of non-covalent bonding is 1:24.4. pH and temperature did not influence the interaction. Taken together, we provide further mechanistic evidence of the beneficial effects of gigantol on DC.

Title

Characterization of structural requirement for binding of gigantol and aldose reductase.

Author

Yang Y1, Yang Q1, Yu J1, Wan W1, Wei X2.

Publish date

2019 Mar 1

PMID

30587838

Abstract

Gigantol is a bibenzyl compound derived from several medicinal orchids. This biologically active compound has shown promising therapeutic potential against diabetic cataracts, but whether this compound exerts beneficial effects on the other diabetic microvascular complications remains unclear. This study was carried out to examine effects of gigantol on high glucose-induced renal cell injury in cultured mouse kidney mesangial cells (MES-13). MES-13 cells were pretreated with gigantol (1, 5, 10 or 20 μmol/L) for 1 h followed by further exposure to high (33.3 mmol/L) glucose for 48 h. Gigantol concentration dependently enhanced cell viability followed by high glucose treatment in MES-13 cells. High glucose induced reactive oxygen species (ROS) generation, malondialdehyde production and glutathione deficiency were recoved in MES-13 cells pretreated with gigantol. High glucose triggered cell apoptosis via the the loss of mitochondrial membrane potential, depletion of adenosine triphosphate, upregulation of caspases 9 and 3, enhancement of cytochrome c release, and subsequent interruption of the Bax/Bcl-2 balance. These detrimental effects were ameliorated by gigantol. High glucose also induced activation of JNK, p38 mitogen-activated protein kinase (MAPK) and nuclear factor-κB (NF-κB) in MES-13 cells, which were blocked by gigantol. The results suggest that treatment MES-13 cells with gigantol halts high glucose-induced renal dysfunction through the suppression of the ROS/MAPK/NF-κB signaling pathways. Our data are of value to the understanding the mechanism for gigantol, and would benefit the study of drug development or food supplement for diabetes and nephropathy.

KEYWORDS

MES-13 cells; NF-κB; diabetic nephropathy; gigantol; high glucose; mitogen-activated protein kinase

Title

Gigantol has Protective Effects against High Glucose-Evoked Nephrotoxicity in Mouse Glomerulus Mesangial Cells by Suppressing ROS/MAPK/NF-κB Signaling Pathways.

Author

Chen MF1,2, Liou SS3, Hong TY4, Kao ST5,6, Liu IM7.

Publish date

2018 Dec 26;

PMID

29614010

Abstract

In order to optimize the extraction of gigantol from Dendrobium officinale, the influence of methanol concentration, ultrasonic temperature, and liquid ratio on extraction efficiency was analysed by the response surface analysis method. The results show that the extraction rate reached a maximum when the methanol concentration was 92.98%, the solid-liquid ratio was 27.2 mL/g, and the extraction temperature was 41.41 °C. The content of gigantol of Dendrobium officinale in leaves was significantly higher than that in stems, reaching 4.7942 μg/g. The content of gigantol in Dendrobium huoshanensis Fengdou was significantly higher than that of other species of Fengdou. This experiment has practical significance for improving the utilization rate of Dendrobium officinale, and provides a reference for the study of the pharmacological and biological activity of gigantol.

KEYWORDS

Dendrobium officinale; gigantol; response surface methodology; ultrasonic-assisted extraction

Title

Extraction and Analysis of Gigantol from Dendrobium officinale with Response Surface Methodology.

Author

Zheng S1, Zhu Y2, Jiao C3, Shi M4, Wei L5, Zhou Y6, Jin Q7, Cai Y8.

Publish date

2018 Apr 3