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Alisol B

$628

  • Brand : BIOFRON

  • Catalogue Number : BD-P0730

  • Specification : 99.0%(HPLC&TLC)

  • CAS number : 18649-93-9

  • Formula : C30H48O4

  • Molecular Weight : 472.7

  • PUBCHEM ID : 15558620

  • Volume : 25mg

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Catalogue Number

BD-P0730

Analysis Method

HPLC,NMR,MS

Specification

99.0%(HPLC&TLC)

Storage

2-8°C

Molecular Weight

472.7

Appearance

White crystalline powder/Cryst.

Botanical Source

Alisma plantag-oaquatica L. var. orientale Samuels.

Structure Type

Triterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(CC(C1C(O1)(C)C)O)C2=C3CC(C4C5(CCC(=O)C(C5CCC4(C3(CC2)C)C)(C)C)C)O

Synonyms

Gon-13(17)-en-3-one, 17-[(1R,3S)-3-[(2S)-3,3-dimethyloxiranyl]-3-hydroxy-1-methylpropyl]-11-hydroxy-8,10,14-trimethyl-, (5α,8α,9β,11β,14β)-/(5α,8α,9β,11β,14β,23S,24S)-11,23-Dihydroxy-8,14-dimethyl-24,25-epoxy-18-norcholest-13(17)-en-3-one

IUPAC Name

(5R,8S,9S,10S,11S,14R)-17-[(2R,4S)-4-[(2R)-3,3-dimethyloxiran-2-yl]-4-hydroxybutan-2-yl]-11-hydroxy-4,4,8,10,14-pentamethyl-1,2,5,6,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-3-one

Applications

Alisol B is a potentially novel therapeutic compound for bone disorders by targeting the differentiation of osteoclasts as well as their functions.IC50 Value:Target:In vitro: The in vitro cultured human renal tubular epithelial HK-2 cells were intervened with 5 ng/mL transforming growth factor-beta (TGF-beta), 0.1 micromol C3a, and 0.1 micromol C3a + 10 micromol alisol B, respectively. Exogenous C3a could induce renal tubular EMT. Alisol B was capable of suppressing C3a induced EMT [1]. Alisol-B strongly inhibited RANKL-induced osteoclast formation when added during the early stage of cultures, suggesting that alisol-B acts on osteoclast precursors to inhibit RANKL/RANK signaling. Among the RANK signaling pathways, alisol-B inhibited the phosphorylation of JNK, which are upregulated in response to RANKL in bone marrow macrophages, alisol-B also inhibited RANKL-induced expression of NFATc1 and c-Fos, which are key transcription factors for osteoclastogenesis. In addition, alisol-B suppressed the pit-forming activity and disrupted the actin ring formation of mature osteoclasts [2]. Alisol B induced calcium mobilization from internal stores, leading to autophagy through the activation of the CaMKK-AMPK-mammalian target of rapamycin pathway. Moreover, the disruption of calcium homeostasis induces endoplasmic reticulum stress and unfolded protein responses in alisol B-treated cells, leading to apoptotic cell death. Finally, by computational virtual docking analysis and biochemical assays, it was showed that the molecular target of alisol B is the sarcoplasmic/endoplasmic reticulum Ca(2+) ATPase [3].In vivo:

Density

1.1±0.1 g/cm3

Solubility

Methanol; Acetontrile; DMSO

Flash Point

181.2±23.6 °C

Boiling Point

567.1±50.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C30H48O4/c1-17(15-21(32)25-27(4,5)34-25)18-9-13-29(7)19(18)16-20(31)24-28(6)12-11-23(33)26(2,3)22(28)10-14-30(24,29)8/h17,20-22,24-25,31-32H,9-16H2,1-8H3/t17-,20+,21+,22+,24+,25-,28+,29+,30+/m1/s1

InChl Key

GBJKHDVRXAVITG-DXYWBWDESA-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#:18649-93-9) 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

29986183

Abstract

Studies on the lipid-regulating effects of alisol compounds are reported that include alisol B, alisol A 24-acetate (24A), alisol A and an alisol B – 24A – alisol A mixture (content ratio = 1:1:1). The effects on the activity of lipoprotein lipase (LPL), a key lipid-modulating enzyme, were studied to investigate the molecular mechanism of lipid-regulating activity of alisols. The effects of alisols on regulating blood lipids and the activities of LPL were determined using a reagent kit method. The structure of LPL was obtained by homology modeling and the interactive mechanism of alisol monomers and the mixture with LPL was investigated by molecular simulation. The alisol monomer and mixture were shown to regulate blood lipids, suggesting that alisols may decrease the level of triglyceride (TG) by improving the activity of LPL. The order of intensity was: mixture > alisol A > alisol B > 24A, indicating that alisols of alismatis rhizoma feature a synergistic effect on LPL. The N- and C-terminus of LPL both represented the catalytic active domains of this lipid-regulating effect. Cys306, Gln129 and Ser166 were the key amino acid residues resulting in the lipid-regulating effect of the alisol monomer while Ser166 and Arg18 were found to be responsible for the lipid-regulating effect of the mixture. The C-terminus of LPL was indirectly involved in the enzymatic process. A folded side chain of alisols or the parent ring was found to bind somewhat weaker to LPL than an open side chain or parent ring. The hydroxyl groups on the C14-, C22-, C28-, C30- and C31-terminus in the side chain, the ring ether structure in C23-position, and the acetyl group in C29-position represented the key sites for the lipid-regulating action of alisols. Meanwhile, the C30-site hydroxyl group played an important role in the synergistic effect of the alisol mixture.

Copyright © 2018 Elsevier Inc. All rights reserved.

KEYWORDS

Activity; Alisol monomer; LPL; Mixture; Molecular simulation

Title

Studies on the lipid-regulating mechanism of alisol-based compounds on lipoprotein lipase.

Author

Xu F1, Lu C2, Wu Q3, Gu W4, Chen J5, Fang F6, Zhao B7, Du W8, You M9.

Publish date

2018 Oct

PMID

29800662

Abstract

Methyl thiazolyl tetrazolium (MTT) assay, UV-vis absorption spectroscopy, fluorescence spectroscopy and molecular simulation were used to investigate the antitumor activity of alisol A, alisol B and an 1:1 mixture of both compounds, the mechanism of its interaction with anti-cancer target p53DNA and explored the antitumor mechanism of alisols. MTT assay showed that the order of antitumor activity was:alisol B > alisol A > alisol A-alisol B(1:1). Spectroscopic experiments and molecular simulation suggested that alisol A, alisol B and their mixture interact with p53DNA in by partial insertion and the strength of binding affinity was consistent with the MTT assay. The Ksv of alisol A was 9.35 × 104 L·mol-1, Kq was 9.35 × 1012 L·mol-1·s-1 and the Ksv and Kq of alisol B were 11.61 × 104 L·mol-1 and 11.61 × 1012 L·mol-1·s-1. The molecular simulation revealed that competitive antagonism was observed in the interaction between the alisol mixture and p53DNA. The critical groups and significant binding sites for the interaction between alisol monomers and p53DNA include C19-OH and C22-OH of the alisols; N2 and H21 of the guanine deoxynucleotide (DG8), N2-H21 of the DG7, O4′ of the DG9 in the f-chain of p53DNA; and C2-O2 of the cytosine deoxynucleotide (DC16) in the e-chain of p53DNA. Also, the C-22 and C23- of the alisols and the DA18-DT5 base pairs of p53DNA were key factors in the interaction of the mixture with p53DNA.

Copyright © 2018 Elsevier B.V. All rights reserved.

KEYWORDS

Alisols; Antitumor activity; Molecular mechanism

Title

Study on antitumor molecular mechanism of Alisols based on p53DNA.

Author

Xu F1, Lu C2, Wu Q3, Chen J4, Gu W2, Du W2, You M2.

Publish date

2018 Sep

PMID

29705003

Abstract

BACKGROUND:
Quality control of traditional Chinese medicines is currently a great concern, due to the correlation between the quality control indicators and clinic effect is often questionable. According to the “multi-components and multi-targets” property of TCMs, a new special quality and bioactivity evaluation system is urgently needed.

PURPOSE:
Present study adopted an integrated approach to provide new insights relating to uncover quality marker underlying the effects of Alisma orientale (AO) on lipid metabolism.

METHODS:
In this paper, guided by the concept of the quality marker (Q-marker), an integrated strategies “effect-compound-target-fingerprint” was established to discovery and screen the potential quality marker of AO based on network pharmacology and chemical analysis. Firstly, a bioactivity evaluation was performed to screen the main active fractions. Then the chemical compositions were rapidly identified by chemical analysis. Next, networks were constructed to illuminate the interactions between these component and their targets for lipid metabolism, and the potential Q-marker of AO was initially screened. Finally, the activity of the Q-markers was validated in vitro.

RESULTS:
50% ethanol extract fraction was found to have the strongest lipid-lowering activity. Then, the network pharmacology was used to clarify the unique relationship between the Q-markers and their integral pharmacological action.

CONCLUSION:
Combined with the results obtained, five active ingredients in the 50% ethanol extract fraction were given special considerations to be representative Q-markers: Alisol A, Alisol B, Alisol A 23-acetate, Alisol B 23-acetate and Alisol A 24-acetate, respectively. The chromatographic fingerprints based Q-marker was establishment. The integrated Q-marker screen may offer an alternative quality assessment of herbal medicines.

Copyright © 2018. Published by Elsevier GmbH.

KEYWORDS

Alisma orientale; Network pharmacology; Q-marker; Quality control

Title

An integrated approach to uncover quality marker underlying the effects of Alisma orientale on lipid metabolism, using chemical analysis and network pharmacology.

Author

Liao M1, Shang H2, Li Y3, Li T4, Wang M3, Zheng Y3, Hou W3, Liu C5.

Publish date

2018 Jun 15