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Hederacoside C

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-H1002

  • Specification : 98%

  • CAS number : 14216-03-6

  • Formula : C59H96O26

  • Molecular Weight : 1221.38

  • PUBCHEM ID : 11491905

  • Volume : 100mg

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Catalogue Number

BF-H1002

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

1221.38

Appearance

White crystalline powder

Botanical Source

herbs of Hedera nepalensis

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC(=O)C45CCC(CC4C6=CCC7C8(CCC(C(C8CCC7(C6(CC5)C)C)(C)CO)OC9C(C(C(CO9)O)O)OC1C(C(C(C(O1)C)O)O)O)C)(C)C)O)O)O)CO)O)O)O

Synonyms

Hederacol/Akebia saponin pk/6-Deoxy-α-L-mannopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-1-O-[(3β)-3-{[2-O-(6-deoxy-α-L-mannopyranosyl)-α-L-arabinopyranosyl]oxy}-23-hydroxy-28-oxoolean-12-en-28-yl]-β-D-glucop yranose/Hederoside H1/Hederacauide D/Glycoside L-H2/kizutasaponin K12/Tauroside H2/hederasaponin C/Hederacoside C/β-D-Glucopyranose, O-6-deoxy-α-L-mannopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-1-O-[(3β)-3-[[2-O-(6-deoxy-α-L-mannopyranosyl)-α-L-arabinopyranosyl]oxy]-23-hydroxy-28-oxoolean- 12-en-28-yl]-/Astrantiasaponin H

IUPAC Name

[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (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-carboxylate

Density

1.5±0.1 g/cm3

Solubility

Methanol

Flash Point

Boiling Point

Melting Point

222ºC (dec.)(lit.)

InChl

InChI=1S/C59H96O26/c1-24-34(63)38(67)42(71)49(78-24)83-46-29(20-60)80-48(45(74)41(46)70)77-22-30-37(66)40(69)44(73)51(81-30)85-53(75)59-17-15-54(3,4)19-27(59)26-9-10-32-55(5)13-12-33(56(6,23-61)31(55)11-14-58(32,8)57(26,7)16-18-59)82-52-47(36(65)28(62)21-76-52)84-50-43(72)39(68)35(64)25(2)79-50/h9,24-25,27-52,60-74H,10-23H2,1-8H3/t24-,25-,27-,28-,29+,30+,31+,32+,33-,34-,35-,36-,37+,38+,39+,40-,41+,42+,43+,44+,45+,46+,47+,48+,49-,50-,51-,52-,55-,56-,57+,58+,59-/m0/s1

InChl Key

RYHDIBJJJRNDSX-MCGLQMIESA-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#:14216-03-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30833026

Abstract

Although some herbal remedies have been used for decades, little is known about the active compounds and the mechanism of action. Many natural products, such as glycosides, can be considered as prodrugs, which become active after biotransformation. To optimize the workflow of in vitro biotransformation followed by automated data analysis, hederacoside C was used as a model compound for saponins. Hederacoside C was subjected to gastrointestinal enzymes and fecal microflora. Samples were analyzed with UHPLC-PDA-HRMS before, during and after in vitro biotransformation, which allowed the monitoring of the relative abundances of the compound and its metabolites. The data-analysis workflow was optimized to render as much information as possible from the longitudinal LCMS data. XCMS was used to convert the raw data into features via peak-picking, followed by grouping, and EDGE was used for the extraction of significant differential profiles. To evaluate if the workflow was suitable for dynamic multiclass metabolomics data, an interactive Shiny web app was developed in R to rate the quality of the resulting features. These ratings were used to train a random forest model for predicting experts response. A performance analysis revealed that the random forest model was capable of correctly predicting the reviewers response in most cases (AUC 0.926 with 10 fold cross validation). The automated data analysis workflow was used for unbiased screening for metabolites and revealed the biotransformation of hederacoside C. As expected, a decrease in relative abundance of hederacoside C was observed over time. Additionally, the relative abundance of metabolites increased, illustrating the biotransformation of hederacoside C, especially in the colon phase, where microbial fermentation takes place. Stepwise progressive elimination of sugar moieties was the major metabolic pathway.

KEYWORDS

Biotransformation; Data-analysis; Hederacoside C; Metabolomics.

Title

Revelation of the Metabolic Pathway of Hederacoside C Using an Innovative Data Analysis Strategy for Dynamic Multiclass Biotransformation Experiments

Author

Laura Peeters 1 , Charlie Beirnaert 2 , Anastasia Van der Auwera 3 , Sebastiaan Bijttebier 3 , Tess De Bruyne 3 , Kris Laukens 2 , Luc Pieters 3 , Nina Hermans 3 , Kenn Foubert 3

Publish date

2019 Jun 21

PMID

27411171

Abstract

Hederacoside C is a principal bioactive pharmaceutical ingredient of Hedera helix leaf extracts. H. helix extracts have long been used in folk medicine for the treatment of respiratory disorders. Currently, hederacoside C is investigated as a promising candidate for the treatment of respiratory diseases. In this study, an accurate, sensitive, rapid, and reliable bioanalytical method was developed for the determination of hederacoside C in rat plasma using ultra high-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). For sample preparation, plasma proteins were precipitated with 0.1% acetic acid in acetonitrile. Waters UPLC BEH C18 (2.1mm I.D.×100mm, 1.7μm) column was used for chromatographic separation. A gradient elution of mobile phases consisting of 0.02% acetic acid in distilled water (solvent A) and 0.02% acetic acid in acetonitrile (solvent B) was used at a flow rate of 0.3mL/min. The multiple reaction monitoring (MRM) mode was used for mass spectrometric detection; the MRM transitions were m/z 1219.7→m/z 469.2 for hederacoside C and m/z 1108.3→m/z 221.2 for ginsenoside Rb1 (internal standard) in the negative ionization mode. A calibration curve was constructed in the range of 10-1000ng/mL. The intra- and inter-day precision and accuracy were within 5%. The developed UPLC-MS/MS method was successfully applied in a pharmacokinetic study of hederacoside C in rats. Hederacoside C was quickly but inadequately absorbed from the gastrointestinal tract of rats resulting in extremely low bioavailability and relatively slow clearance.

KEYWORDS

Hedera helix; Hederacoside C; Pharmacokinetics; Plasma; UPLC-MS/MS.

Title

An Ultra-High-Performance Liquid Chromatography-Tandem Mass Spectrometric Method for the Determination of Hederacoside C, a Drug Candidate for Respiratory Disorder, in Rat Plasma

Author

Shaheed Ur Rehman 1 , Min Sun Choi 1 , In Sook Kim 1 , Seung Hyun Kim 2 , Hye Hyun Yoo 3

Publish date

2016 Sep 10

PMID

31845052

Abstract

Hederacoside-C (HDC) is a biological active ingredient, extracted from the leaves of Hedera helix. It has been reported to have anti-inflammatory properties. However, the effects of HDC on Staphylococcus aureus (S. aureus)-induced mastitis have not been reported yet. Here, we evaluated the anti-inflammatory effects of HDC on S. aureus-induced mastitis both in vivo on mammary gland tissues and in vitro on RAW 264.7 cells. The ascertained histopathological changes and MPO activity revealed that HDC defended mammary glands from tissue destruction and inflammatory cell infiltration induced by S. aureus. The results of ELISA, western blot, and qRT-PCR indicated that HDC significantly inhibited the expressions IL-6, IL-1β, and TNF-α and enhanced the IL-10 by downregulating and upregulating their relevant genes, respectively. Furthermore, HDC markedly suppressed the TLR2 and TLR4 expressions by attenuating the MAPKs (p38, ERK, JNK) and NF-κB (p65 and IκBα) pathways followed by decreasing the phosphorylation of p38, ERK, JNK, p65, and IκBα. The above parameters enhanced the mammary gland defense and reduced inflammation. These findings suggested that HDC may have the potential to be an effective anti-inflammatory drug for the S. aureus-induced mice mastitis and in RAW 264.7 cells.

KEYWORDS

HDC; Mastitis; NF-κB and MAPKs; S. aureus; TLR2 and TLR4.

Title

Hederacoside-C Inhibition of Staphylococcus aureus-Induced Mastitis via TLR2 & TLR4 and Their Downstream Signaling NF-κB and MAPKs Pathways In Vivo and In Vitro

Author

Muhammad Akhtar 1 , Aftab Shaukat 1 , Arshad Zahoor 1 , Yu Chen 1 , Ying Wang 1 , Mei Yang 1 , Talha Umar 1 , Mengyao Guo 2 , Ganzhen Deng 3

Publish date

2019 Dec 17


Description :

Hederacoside C is a principal bioactive pharmaceutical ingredient of Hedera helix leaf that can treat respiratory disorders, because of its expectorant, bronchodilator, antibacterial, and bronchospasmolytic effects.