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α-Hederin

$225

  • Brand : BIOFRON

  • Catalogue Number : BF-H1004

  • Specification : 98%

  • CAS number : 27013-91-8

  • Formula : C41H66O12

  • Molecular Weight : 750.96

  • PUBCHEM ID : 73296

  • Volume : 20mg

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Catalogue Number

BF-H1004

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

750.96

Appearance

White crystalline powder

Botanical Source

HederanepalensisK.Kochvar.sinensis(Tobl.)Rehd/Hedera helix; Chinese ivy; Hedera nepalensis K,Koch var.sinensis (Tobl.) Rehd

Structure Type

Triterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)CO)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)O)C)C)C)O)O)O)O)O

Synonyms

α-Hederin/(3β)-3-{[2-O-(6-Deoxy-α-L-mannopyranosyl)-α-L-arabinopyranosyl]oxy}-23-hydroxyolean-12-en-28-oic acid/Alpha-hederin/glycosidel-e1/Olean-12-en-28-oic acid, 3-[[2-O-(6-deoxy-α-L-mannopyranosyl)-α-L-arabinopyranosyl]oxy]-23-hydroxy-, (3β)/sapindosidea/HELIXIN/nepalin2/dipsacobioside/Hederoside B/koronaroside A/hederosidec/akebosidestc/taurosidee/A-HEDERIN/SAPINDOSIDE A/HEDERIN/Hederin, α-/alpha-Hederin

IUPAC Name

(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Density

1.3±0.1 g/cm3

Solubility

DMSO : ≥ 100 mg/mL (133.16 mM)
H2O : < 0.1 mg/mL (insoluble)
*"≥" means soluble, but saturation unknown.

Flash Point

250.7±27.8 °C

Boiling Point

849.6±65.0 °C at 760 mmHg

Melting Point

215ºC (dec.)

InChl

InChl Key

KEOITPILCOILGM-LLJOFIFVSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:27013-91-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31443189

Abstract

Alpha-hederin (α-HN), a pentacyclic triterpene saponin, has recently been identified as one of the active compounds of Nigella sativa, as a potential anticancer agent. However, no extensive studies on α-HN have been done as yet, as it was in the case of thymoquinone-the main ingredient of the N. sativa essential oil. To our knowledge, there are also no data available on how α-HN acts on the human cancer ovarian cell line SKOV-3. In this study we attempt to present the cytotoxic influence of α-HN on the SKOV-3 cell line by means of two methods: Real-Time xCELLigence and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The obtained IC50 values are 2.62 ± 0.04 μg/mL and 2.48 ± 0.32 μg/mL, respectively. An induction of apoptosis in SKOV-3 cells was confirmed by staining cellular nuclei with Hoechst 33342 dye and by flow cytometry analysis by binding annexin V to the cell membranes. We found that α-HN induces apoptosis in a dose-dependent manner. In the first stages of apoptosis, the mitochondrial membrane potential was found to decrease. Also, inactivation of anti-apoptotic protein Bcl-2 was observed, as well as the caspase-9 and then caspase-3/7 activation. In addition, the treatment of SKOV-3 cells with α-HN induced the cell cycle arrest of cancer cells in G0/G1 phase. The results of our investigations indicate that α-HN induces apoptosis in the SKOV-3 cell line and that the intrinsic mitochondrial pathway is involved in the programmed cancer cell death.

KEYWORDS

MMP; MTT assay; RTCA; annexin; caspases; cell cycle; flow cytometry; triterpene saponin

Title

Alpha-Hederin, the Active Saponin of Nigella sativa, as an Anticancer Agent Inducing Apoptosis in the SKOV-3 Cell Line.

Author

Adamska A1, Stefanowicz-Hajduk J2, Ochocka JR3.

Publish date

2019 Aug 15

PMID

31039532

Abstract

BACKGROUND:
Quality control of herbal medicines based on characteristic components is an important trend. Although the plant metabolomics provide a powerful tool for species classification, the discovered marker is usually limited in practical application. For rapid discovery of efficient marker combination, we proposed a strategy integrating targeted metabolite profiling and sequential optimization method.

METHODS:
This strategy included: (1) directional enrichment and chemical profiling of targeted metabolites by matrix solid phase dispersion (MSPD) combined with liquid chromatography-tandem mass spectrometry (LC-MS/MS). (2) Partial least squares discrimination analysis (PLS-DA)-based sequential screening of efficient marker combination was constructed for various species predictions. Five Lonicera species and their characteristic metabolites, sponins, were taken as a case study.

RESULTS:
A total of 19 saponins were identified, and 12 major and available saponins were enriched based on MSPD and quantified by LC-MS/MS in 5 Lonicera species flower buds. Followed by 3 runs of PLS-DA-based screening, a combination consisting of macranthoidin B, dipsacoside B and α-hederin was discovered as the effective chemical marker for 5 analogous Lonicera flower classification.

CONCLUSION:
Our study provides an effective and applicable approach to select the practical marker combination for the assessment of analogical herb medicines.

Copyright ? 2019. Published by Elsevier GmbH.

KEYWORDS

Chemical markers; Lonicera flower; Partial least squares discrimination analysis; Saponin; Sequential optimization method; Targeted metabolomics

Title

Integration of targeted metabolite profiling and sequential optimization method for discovery of chemical marker combination to identify the closely-related plant species.

Author

Gao W1, Liu K2, Wang R3, Liu XG4, Li XS5, Li P6, Yang H7.

Publish date

2019 Aug;

PMID

30896843

Abstract

α?hederin, a monodesmosidic triterpenoid saponin, had previously demonstrated strong anticancer effects. In the current study, the pharmacological mechanism of autophagic cell death induced by α?hederin was investigated in human colorectal cancer cells. First, through cell counting kit?8 and colony formation assays, it was demonstrated that α?hederin could inhibit the proliferation of HCT116 and HCT8 cell. Results of flow cytometry using fluorescein isothiocyanate Annexin V/propidium iodide and Hoechst 33258 staining indicated that α?hederin could induce apoptosis. Western blotting demonstrated that α?hederin could activate mitochondrial apoptosis signal pathway. Then, using light chain 3 lentiviral and electron microscope assay, it was demonstrated that α?hederin could induce autophagy in colorectal cancer cells. In addition, immunohistochemistry results from in vivo experiments also demonstrated that α?hederin could induce autophagy. AMP?activated protein kinase (AMPK)/mechanistic target of rapamycin (mTOR) signaling was demonstrated to be activated by α?hederin, which could be blocked by reactive oxygen species (ROS) inhibitor NAC. Furthermore, NAC could inhibit apoptosis and autophagy induced by α?hederin. Finally, 3?MA (autophagy inhibitor) reduced the inhibition of α?hederin on cell activity, but it had no significant effect on apoptosis. In conclusion, α?hederin triggered apoptosis through ROS?activated mitochondrial signaling pathway and autophagic cell death through ROS dependent AMPK/mTOR signaling pathway activation in colorectal cancer cells.

Title

α-hederin induces autophagic cell death in colorectal cancer cells through reactive oxygen species dependent AMPK/mTOR signaling pathway activation.

Author

Sun J1, Feng Y2, Wang Y2, Ji Q2, Cai G2, Shi L1, Wang Y1, Huang Y1, Zhang J1, Li Q2.


Description :

alpha-hederin is a water-soluble pentacyclic triterpenoid saponin, possessing several biological properties such as antispasmodic, moliscicidic, anthelmithic and inhibiting cell proliferation,In vitro: a-hederin is cytotoxic and inhibits proliferation in bothcel lines at rather low concentrations. , a-hederin reduces themitotic activity in treated cels.[1]In vivo: alpha-hederin had preventive effect on sensitized rats like thymoquinone. It may intervene in miRNA-126 expression, which consequently could interfere with IL-13 secretion pathway leading to a reduction in inflammatory responses. [2]