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Hecogenin

$168

  • Brand : BIOFRON

  • Catalogue Number : BD-D0644

  • Specification : HPLC≥98%

  • CAS number : 467-55-0

  • Formula : C27H42O4

  • Molecular Weight : 430.62

  • PUBCHEM ID : 91453

  • Volume : 20mg

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Catalogue Number

BD-D0644

Analysis Method

Specification

HPLC≥98%

Storage

-20℃

Molecular Weight

430.62

Appearance

Powder

Botanical Source

This product is isolated and purified from the roots of Aconitum carmichaeli Debx

Structure Type

Category

SMILES

CC1CCC2(C(C3C(O2)CC4C3(C(=O)CC5C4CCC6C5(CCC(C6)O)C)C)C)OC1

Synonyms

5ALPHA-SPIROSTAN-3BETA-OL-12-ONE/5α-Spirostan-12-one, 3β-hydroxy-, (25R)-/(25R)-5-Spirostan-3-ol-12-one/(22R,25R)-3β-Hydroxy-5α-spirostan-12-one/Spirostan-12-one, 3-hydroxy-, (3β,5α,25R)-/12-Oxotigogenin/(3β,5α,25R)-3-Hydroxyspirostan-12-one/Hocogenin/Hecoginin/(25R)-3b-Hydroxy-5a-spirostan-12-one/Hecogenin/3-b-Hydroxy-5-a-spirostan-12-one/(3,5,25R)-3-Hydroxysiprostan-1/(3,5,25R)-3-Hydroxysiprostan-12-one/(3b,5a,25R)-3-Hydroxyspirostan-12-one

IUPAC Name

Density

1.2±0.1 g/cm3

Solubility

Methanol; Chloroform

Flash Point

177.8±23.6 °C

Boiling Point

548.9±50.0 °C at 760 mmHg

Melting Point

268°C

InChl

InChl Key

QOLRLLFJMZLYQJ-LOBDNJQFSA-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#:467-55-0) 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

31602852

Abstract

The contents of terrestrosin D and hecogenin from Tribuli Fructus were determined before and after stir-frying. The results showed that the content of terrestrosin D was decreased significantly,and the content of hecogenin was increased significantly after such processing. In order to verify the inference that terrestrosin D was converted to hecogenin by stir-frying,the quantitative variation rules of terrestrosin D and hecogenin were studied by simulated processing technology,and the simulated processing product of terrestrosin D was qualitatively characterized by ultra performance liquid chromatography/time of flight mass spectrometry( UPLC-TOF/MS) to clarify its transformation process during stir-frying. The results showed that the content of terrestrosin D was decreased significantly at first and then a platform stage appeared with the prolongation of processing time at a certain temperature. Raising the stir-frying temperature could further decrease the content of terrestrosin D and delay the time that the platform stage appeared. When the processing was simulated at higher temperatures( 220 ℃ and 240 ℃),the content of hecogenin was increased gradually with the increase of processing temperature and the prolongation of processing time. In the process of stir-frying,the deglycosylation reaction of terrestrosin D to hecogenin was not completed in one step. The deglycosylation reaction occurred first at the end of the sugar chain,and then other glycosyl units in the sugar chain were sequentially removed from the outside to the inside to finally form the hecogenin. This study provides a basis for further revealing the detoxification mechanism of stir-fried Tribuli Fructus.

KEYWORDS

Tribuli Fructus; deglycosylation reaction; hecogenin; simulated processing; terrestrosin D

Title

[Study on transformation rules of terrestrosin D in course of Tribuli Fructus stir-frying based on simulated processing technology].

Author

Yuan R1, Su T1, Zhang C1, Song X1, Yuan YH1, Li RT1, Liu YJ1.

Publish date

2019 Jul

PMID

31039648

Abstract

Objective: Hecogenin is a sapogenin found in Agave sisalana species that is used extensively for the treatment of anti-inflammatory, antifungal, hypotensive, anti-nociceptive activity and cancer. We have studied the anti-inflammatory effect of Hecogenin and its combination with Fluticasone on atopic dermatitis and airway hyper-responsiveness in Balb/c mice. Material and methods: Dermatitis was induced by repeated application of 2, 4-dinitrofluorobenzene in Balb/c mice. After a topical application of Hecogenin, Fluticasone and their combination on the skin lesions, the ear thickness, ear weight and erythema score were evaluated. Asthma was induced by sensitization and challenge of ovalbumin in Balb/c mice. Results: The topical application of Hecogenin and its combination with Fluticasone in mice effectively suppressed the ear swelling and weight. As well as the levels of pro-inflammatory cytokines were decreased by Hecogenin and its combination in-vivo. Whereas, intra-nasal administration of Hecogenin and its combination in ovalbumin induced airway hyper-responsiveness reveals a significant decrement in total cell count, differential cell count and cytokines levels. Similar observations were obtained for myeloperoxidase level in ear and lung tissue. The results were supported by histological studies of ear and lung tissue. Conclusion: These data indicate that Hecogenin has been proved as a potential therapy for allergic skin diseases and bronchial asthma treatments in combination with Fluticasone by reducing its dose from 50 to 25 μg/mice in combination to circumvent the long term side effects of Fluticasone. The beneficial effect of Hecogenin may be related to the diminution of TNF-α and IL-12 cytokines production in Balb/c mice

KEYWORDS

2,4-dintroflurobenzene; Hecogenin; fluticasone; histopathology; ovalbumin; pro-inflammatory cytokines

Title

Anti-inflammatory potential of hecogenin on atopic dermatitis and airway hyper-responsiveness by regulation of pro-inflammatory cytokines.

Author

Ingawale DK1,2, Mandlik SK3, Patel SS1.

Publish date

2019 Apr

PMID

29192804

Abstract

Hecogenin is a steroidal sapogenin isolated from the leaves of Agave genus species that plays an important role in the treatment of a variety of inflammatory diseases. The aim of the present study was to evaluate the anti-arthritic activity of hecogenin in Complete Freund’s adjuvant-induced arthritis in rats. The hecogenin (40 µl of 50 µg/kg, orally) and hecogenin + fluticasone (40 µl of 25 µg/kg, each, orally) was tested against Complete Freund’s adjuvant-induced arthritis in rats by evaluating various parameters such as paw volume, arthritic score, joint diameter, spleen weight, thymus weight, haematological and biochemical parameters and pro-inflammatory cytokines. Histopathological and radiological analyzes of ankle joints were also carried out. Treatment of rats with hecogenin and its combination elicited significant reduction in paw edema, arthritic score and joint diameter. Hecogenin and its combination also inhibited joint destruction in histopathological and radiological analyzes of ankle joint. Hecogenin and its combination significantly increased the levels of red blood cells and hemoglobin but decreased the white blood cell count. The anti-arthritic activity was also confirmed with the change in biochemical parameters and myeloperoxidase assay. In the present investigation, hecogenin and its combination prevent destruction of cartilage and protect synovial membrane with improving health status through haematonic properties and down regulation of various cytokines. Hence, hecogenin may be a potential therapeutic candidate for the treatment of rheumatoid arthritis.

KEYWORDS

Complete Freund’s adjuvant; Rheumatoid arthritis; fluticasone; hecogenin; myeloperoxidase; pro-inflammatory cytokines

Title

Hecogenin exhibits anti-arthritic activity in rats through suppression of pro-inflammatory cytokines in Complete Freund's adjuvant-induced arthritis.

Author

Ingawale DK1,2, Patel SS1.

Publish date

2018 Feb


Description :

Different contribution of apoptosis to the antiproliferative effects of diosgenin and other plant steroids, hecogenin and tigogenin, on human 1547 osteosarcoma cells.[Pubmed: 12632085]Int J Oncol. 2003 Apr;22(4):899-905. Regulation of growth arrest and apoptosis are, in part, controlled by the tumor suppressor p53 after its phosphorylation which causes a determinant role in its functional activation. Moreover, PPAR regulate many functions such as proliferation and apoptosis. METHODS AND RESULTS: We compared the biological activity of diosgenin with Hecogenin and tigogenin, plant steroids structurally close to diosgenin, on proliferation rate, cell cycle distribution and apoptosis in human 1547 osteosarcoma cells. We found that all three molecules have an antiproliferative effect but gel shift analysis demonstrated that none of the plant steroids transactivated PPAR in human 1547 osteosarcoma cells whereas these molecules induced NF-kappaB binding to DNA. Although these plant steroids have a very close structure, only diosgenin caused a cell cycle arrest associated with strong apoptosis. This biological action seems correlated with a large increase of p53 protein expression. CONCLUSIONS: This fact was showed by immunofluorescence analysis which confirmed that diosgenin strongly enhanced the activation of p53 in contrast to Hecogenin and tigogenin actions.