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10-Gingerol

$231

  • Brand : BIOFRON

  • Catalogue Number : BD-D1358

  • Specification : 98%(HPLC)

  • CAS number : 23513-15-7

  • Formula : C21H34O4

  • Molecular Weight : 350.49

  • PUBCHEM ID : 168115

  • Volume : 20MG

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Catalogue Number

BD-D1358

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

350.49

Appearance

Yellow paste

Botanical Source

Zingiber officinale Roscoe/ginger (Zingiber officinale)

Structure Type

Phenols

Category

Standards;Natural Pytochemical;API

SMILES

CCCCCCCCCC(CC(=O)CCC1=CC(=C(C=C1)O)OC)O

Synonyms

(S)- 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-tetradecanone/(5S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-tetradecanone/(5s)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)tetradecan-3-one/<10>-Gingerol/10-Gingerol/3-Tetradecanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (5S)-

IUPAC Name

(5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)tetradecan-3-one

Applications

10-Gingerol is a major pungent constituent in the ginger oleoresin from fresh rhizome, with anti-inflammatory, antioxidant and anti-proliferative activities. 10-Gingerol inhibits the proliferation of MDA-MB-231 tumor cell line with an IC50 of 12.1 μM[1][2].

Density

1.0±0.1 g/cm3

Solubility

Methanol

Flash Point

166.4±19.4 °C

Boiling Point

499.7±35.0 °C at 760 mmHg

Melting Point

45 - 46 °C

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2914400000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:23513-15-7) 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

28315687

Abstract

The ginger rhizome is rich in bioactive compounds, including [6]-gingerol, [8]-gingerol, and [10]-gingerol; however, to date, most research on the anti-cancer activities of gingerols have focused on [6]-gingerol. In this study, we compared [10]-gingerol with [8]-gingerol and [6]-gingerol in terms of their ability to inhibit the growth of human and mouse mammary carcinoma cells. A colorimetric assay based on the enzymatic reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide revealed that [10]-gingerol was more potent than [6]-gingerol and at least as potent as [8]-gingerol for the inhibition of triple-negative human (MDA-MB-231, MDA-MB-468) and mouse (4T1, E0771) mammary carcinoma cell growth. Further investigation of [10]-gingerol showed that it suppressed the growth of estrogen receptor-bearing (MCF-7, T47D) and HER2-overexpressing (SKBR3) breast cancer cells. The inhibitory effect of [10]-gingerol on the growth of MDA-MB-231 cells was associated with a reduction in the number of rounds of cell division and evidence of S phase-cell cycle arrest, as well as induction of apoptosis due to mitochondrial outer membrane permeabilization and the release of proapoptotic mitochondrial cytochrome c and SMAC/DIABLO into the cytoplasm. Surprisingly, killing of MDA-MB-231 cells by [10]-gingerol was not affected by a pan-caspase inhibitor (zVAD-fmk) or an anti-oxidant (N-acetylcysteine), suggesting that the cytotoxic effect of [10]-gingerol did not require caspase activation or the accumulation of reactive oxygen species. These findings suggest that further investigation of [10]-gingerol is warranted for its possible use in the treatment of breast cancer.

KEYWORDS

Apoptosis; Breast cancer; Cell cycle; Gingerol.

Title

[10]-Gingerol, a Major Phenolic Constituent of Ginger Root, Induces Cell Cycle Arrest and Apoptosis in Triple-Negative Breast Cancer Cells

Author

Megan M Bernard 1 , Jason R McConnery 1 , David W Hoskin 2

Publish date

2017 Apr

PMID

30370858

Abstract

Background: Triple Negative Breast Cancer (TNBC) represents the approximately 15% of breast cancers that lack expression of Estrogen (ER) and Progesterone Receptors (PR) and do not exhibit amplification of the human epidermal growth factor receptor 2 (HER2) gene, imposing difficulties to treatment. Interactions between tumor cells and their microenvironment facilitate tumor cell invasion in the surrounding tissues, intravasation through newly formed vessels, and dissemination to form metastasis. To treat metastasis from breast and many other cancer types, chemotherapy is one of the most extensively used methods. However, its efficacy and safety remain a primary concern, as well as its toxicity and other side effects. Thus, there is increasing interest in natural antitumor agents. In a previous work, we have demonstrated that [10]-gingerol is able to revert malignant phenotype in breast cancer cells in 3D culture and, moreover, to inhibit the dissemination of TNBC to multiple organs including lung, bone and brain, in spontaneous and experimental in vivo metastasis assays in mouse model.
Objectives: This work aims to investigate the in vitro effects of [10]-gingerol, using human MDA-MB-231TNBC cells, in comparison to non-tumor MCF-10A breast cells, in order to understand the antitumor and antimetastatic effects found in vivo and in a 3D environment.
Methods: We investigated different steps of the metastatic process in vitro, such as cell migration, invasion, adhesion and MMP activity. In addition, we analyzed the anti-apoptotic and genotoxic effects of [10]-gingerol using PEAnnexin, DNA fragmentation, TUNEL and comet assays, respectively.
Results: [10]-gingerol was able to inhibit cell adhesion, migration, invasion and to induce apoptosis more effectively in TNBC cells, when compared to non-tumor cells, demonstrating that these mechanisms can be involved in the antitumor and antimetastatic effects of [10]-gingerol, found both in 3D culture and in vivo.
Conclusion: Taken together, results found here are complementary to previous studies of our group and others and demonstrate that additional mechanisms, besides apoptotic cell death, is used by [10]-gingerol to accomplish its antitumor and antimetastatic effects. Our results indicate a potential for this natural compound as an antitumor molecule or as an adjuvant for chemotherapeutics already used in the clinic.

KEYWORDS

Apoptosis; Breast cancer; Cell cycle; Gingerol.

Title

[10]-Gingerol Affects Multiple Metastatic Processes and Induces Apoptosis in MDAMB- 231 Breast Tumor Cells

Author

Angelina M Fuzer 1 , Ana C B M Martin 1 , Amanda B Becceneri 1 , James A da Silva 2 , Paulo C Vieira 3 , Marcia R Cominetti 1

Publish date

2019

PMID

31857975

Abstract

Purpose: Gingerol homologs found in the rhizomes of ginger plants have the potential to benefit human health, including the prevention and treatment of cancer. This study evaluated the effect of 10-gingerol on ovarian cancer cell (HEY, OVCAR3, and SKOV-3) growth. Methods: Cell growth was measured by MTT assays, flow cytometry was used to assess cell proliferation, cytotoxicity and cell cycle progression, and western blotting was used to measure cyclin protein expression. Results: Ovarian cancer cells that were treated with 10-gingerol experienced a time- and dose-dependent decrease in cell number, which was due to a reduction in cell proliferation rather than a cytotoxic effect. Reduced proliferation of 10-gingerol-treated ovarian cancer cells was associated with an increased percentage of cells in G2 phase of the cell cycle and a corresponding reduction in the percentage of cells in G1. Ovarian cancer cells also showed decreased cyclin A, B1, and D3 expression following exposure to 10-gingerol. Conclusion: These findings revealed that 10-gingerol caused a G2 arrest-associated suppression of ovarian cancer cell growth, which may be exploited in the management of ovarian cancer.

KEYWORDS

10-Gingerol; Cell cycle; Ginger; Ovarian cancer; Proliferation.

Title

10-Gingerol Inhibits Ovarian Cancer Cell Growth by Inducing G2 Arrest

Author

Andrea Rasmussen 1 , Kaylee Murphy 2 , David W Hoskin 1 2 3

Publish date

2019 Oct