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Tenacissoside H

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-T4004

  • Specification : 98%(HPLC)

  • CAS number : 191729-45-0

  • Formula : C42H66O14

  • Molecular Weight : 794.96

  • PUBCHEM ID : 75412560

  • Volume : 20mg

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Catalogue Number

BF-T4004

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

794.96

Appearance

White powder

Botanical Source

Marsdenia tenacissima

Structure Type

Others

Category

Standards;Natural Pytochemical;API

SMILES

CCC(C)C(=O)OC1C2C3(CCC(CC3CCC24C5(O4)CCC(C5(C1OC(=O)C)C)C(=O)C)OC6CC(C(C(O6)C)OC7C(C(C(C(O7)C)O)OC)O)OC)C

Synonyms

(3β,5α,11α,12β,14β,17α)-12-Acetoxy-3-{[2,6-dideoxy-4-O-(6-deoxy-3-O-methyl-β-D-allopyranosyl)-3-O-methyl-β-D-arabino-hexopyranosyl]oxy}-20-oxo-8,14-epoxypregnan-11-yl 2-meth ylbutanoate/Butanoic acid, 2-methyl-, (3β,5α,11α,12β,14β,17α)-12-(acetyloxy)-3-[[2,6-dideoxy-4-O-(6-deoxy-3-O-methyl-β-D-allopyranosyl)-3-O-methyl-β-D-arabino-hexopyranosyl]oxy]-8,14-ep oxy-20-oxopregnan-11-yl ester/Tenacissoside H

IUPAC Name

[(1S,3R,6R,7S,8S,9S,10S,11S,14S,16S)-6-acetyl-8-acetyloxy-14-[(2R,4R,5R,6R)-5-[(2S,3R,4R,5R,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-7,11-dimethyl-2-oxapentacyclo[8.8.0.01,3.03,7.011,16]octadecan-9-yl] 2-methylbutanoate

Density

1.3±0.1 g/cm3

Solubility

Methanol; Acetontrile; DMSO

Flash Point

235.5±27.8 °C

Boiling Point

815.4±65.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C42H66O14/c1-11-20(2)37(47)54-34-35-39(7)15-13-26(53-29-19-28(48-9)32(23(5)50-29)55-38-31(46)33(49-10)30(45)22(4)51-38)18-25(39)12-16-41(35)42(56-41)17-14-27(21(3)43)40(42,8)36(34)52-24(6)44/h20,22-23,25-36,38,45-46H,11-19H2,1-10H3/t20?,22-,23-,25+,26+,27+,28-,29+,30-,31-,32-,33-,34+,35-,36-,38+,39+,40+,41+,42-/m1/s1

InChl Key

HRSFCYYMBMDMOU-ZIAOJATMSA-N

WGK Germany

RID/ADR

HS Code Reference

2937900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:191729-45-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30213642

Abstract

Marsdenia tenacissima exhibits biological activity with heat-clearing and detoxifying properties, relieving coughs and asthma and exerting anticancer and anti-HIV effects. Tenacissioside H (TH) is a Chinese medicine monomer extracted from the dried stem of Marsdenia tenacissima. We investigated the in vivo anti-inflammatory activity of TH using three different zebrafish inflammation models: local inflammation induced by tail cutting, acute inflammation induced by CuSO4, and systemic inflammation induced by lipopolysaccharide (LPS). Real time-polymerase chain reaction (RT-PCR) was used to elucidate the mechanism of TH action against LPS-induced inflammatory responses. Our results showed TH significantly reduced the number of macrophages in the injured zebrafish tail, inhibited CuSO4-induced migration of macrophages toward the neural mound, and decreased the distribution of macrophages in tail fin compared to LPS-treated group. Furthermore, TH inhibits LPS-induced inflammation responses in zebrafish by modulating the nuclear factor κB (nf-κb) and p38 pathways to regulate inflammatory cytokines, such as tumor necrosis factor-α (tnf-α), cyclooxygenase (cox-2), interleukin-1b (il-1b), interleukin-8 (il-8), interleukin-10 (il-10), nitric oxide synthase (nos2b) and prostaglandin E synthase (ptges). In conclusion, TH possesses anti-inflammation activity via the regulation of the nf-κb and p38 pathways. This finding provides a reference for the clinical application of Xiaoaiping (the trade name of Marsdenia tenacissima extract).

KEYWORDS

Anti-Inflammatory; Lipopolysaccharide; Tenacissoside H; Zebrafish; nf-κb pathway; p38 pathway.

Title

Tenacissoside H Exerts an Anti-Inflammatory Effect by Regulating the Nf-κb and p38 Pathways in Zebrafish

Author

Juan-Juan Li 1 , Yun Zhang 2 , Li-Wen Han 3 , Qing-Ping Tian 4 , Qiu-Xia He 3 , Xi-Min Wang 3 , Chen Sun 3 , Jian Han 3 , Ke-Chun Liu 5

Publish date

2018 Dec

PMID

26495015

Abstract

Objective. The purpose of the study was to elucidate the molecular mechanism of tenacissoside H (TDH) inhibiting esophageal carcinoma infiltration and proliferation. Methods. In vitro, EC9706 cells were treated with TDH. Cells proliferation and cell cycle were assayed. PI3K and NF-κB mRNAs expression were determined by real time PCR. In vivo, model of nude mice with tumor was established. Mice were treated with TDH. Inhibition ratio of tumor volume was calculated. PCNA expression was examined. Protein expression in PI3K/Akt-NF-κB signaling pathway was determined. Results. In vitro, TDH significantly inhibited cells proliferation in a time-and-dose-dependent manner. TDH arrested the cell cycle in S phase and significantly inhibited PI3K and NF-κB mRNA expression, compared with blank controlled group (P < 0.05). In vivo, TDH strongly inhibits tumor growth and volume. PCNA expression was significantly decreased after treatment of TDH. TDH downregulated proteins expression in PI3K/Akt-NF-κB transduction cascade (P < 0.05). Conclusion. TDH inhibited esophageal carcinoma infiltration and proliferation both in vitro and in vivo. The anticancer activity has relation to arresting the cell cycle at the S phase, inhibited the PCNA expression of transplanted tumors in nude mice, and regulated the protein expression in the PI3K/Akt-NF-κB transduction cascade.

KEYWORDS

Anti-Inflammatory; Lipopolysaccharide; Tenacissoside H; Zebrafish; nf-κb pathway; p38 pathway.

Title

Antitumor Activity of Tenacissoside H on Esophageal Cancer Through Arresting Cell Cycle and Regulating PI3K/Akt-NF-κB Transduction Cascade

Author

Yong-Sen Jia 1 , Xue-Qin Hu 2 , Hegyi Gabriella 3 , Li-Juan Qin 4 , Nora Meggyeshazi 5

Publish date

2015

PMID

27106066

Abstract

Marsdenia tenacissima, which is widely used as an anticancer herb in traditional Chinese medicine, has been shown to possess anticancer activity. However, its metabolic profile is poorly investigated. Tenacigenin B is the major steroidal skeleton of C-21 steroids in M. tenacissima. Tenacissoside H and Tenacissoside I are detected at relatively high levels in M. tenacissima. Therefore, we studied their metabolic characteristics in human liver microsomes by ultra-high-performance liquid chromatography coupled with high-resolution mass spectrometry. Fourteen metabolites were tentatively identified by accurate mass measurement and MS/MS fragmentation behavior. It was found that hydroxylation reactions were the major metabolic pathway of Tenacissoside H and Tenacissoside I in human liver microsomes, whereas the metabolic pathway of Tenacigenin B involved dehydrogenation reactions. This is the first time that the metabolic profile of C-21 steroids from M. tenacissima has been explored in human liver microsomes, which is of great significance for subsequent pharmacokinetic and interaction research. Biotransformation in vivo or in vitro may influence the structure of a compound and change its activity. Identification of their fragmentation behaviors and metabolites provides valuable and new information for further understanding the anti-tumor activity of M. tenacissima. Copyright © 2016 John Wiley & Sons, Ltd.

KEYWORDS

Tenacigenin B; Tenacissoside H; Tenacissoside I; human liver microsomes; mass spectrometer; metabolism.

Title

Metabolic Profiling of Tenacigenin B, Tenacissoside H and Tenacissoside I Using UHPLC-ESI-Orbitrap MS/MS

Author

Can Zhao 1 2 , Ling-Yu Han 3 , Wei Ren 3 4 , Hai-Yu Zhao 3 , Shu-Yan Han 5 6 , Wen-Xian Zheng 1 2 , Li-Na Pang 1 2 , Xiao-Hong Li 1 2 , Ping-Ping Li 7 8

Publish date

2016 Nov


Description :

Tenacissoside H is a Chinese medicine monomer extracted, isolated from Caulis Marsdeniae Tenacissimae.IC50 value:Target:In vitro: TDH significantly inhibited cells proliferation in a time-and-dose-dependent manner. TDH arrested the cell cycle in S phase and significantly inhibited PI3K and NF-κB mRNA expression, compared with blank controlled group (P < 0.05). [1]In vivo: TDH strongly inhibits tumor growth and volume. PCNA expression was significantly decreased after treatment of TDH. TDH downregulated proteins expression in PI3K/Akt-NF-κB transduction cascade (P < 0.05). [1]