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Cleomiscosin A

$431

  • Brand : BIOFRON

  • Catalogue Number : BD-P0436

  • Specification : 98.0%(HPLC)

  • CAS number : 76948-72-6

  • Formula : C20H18O8

  • Molecular Weight : 386.4

  • PUBCHEM ID : 442510

  • Volume : 5mg

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Catalogue Number

BD-P0436

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

386.4

Appearance

Powder

Botanical Source

Structure Type

Coumarins

Category

SMILES

COC1=C(C=CC(=C1)C2C(OC3=C4C(=CC(=C3O2)OC)C=CC(=O)O4)CO)O

Synonyms

(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one

IUPAC Name

(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one

Applications

Density

1.4±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

228.5±25.0 °C

Boiling Point

632.7±55.0 °C at 760 mmHg

Melting Point

245-247ºC

InChl

InChI=1S/C20H18O8/c1-24-13-7-10(3-5-12(13)22)17-15(9-21)26-20-18-11(4-6-16(23)27-18)8-14(25-2)19(20)28-17/h3-8,15,17,21-22H,9H2,1-2H3/t15-,17-/m0/s1

InChl Key

OCBGWPJNUZMLCA-RDJZCZTQSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:76948-72-6) 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

23022518

Abstract

A series of five (6a-8b) novel polyhalogenated derivatives and an interesting ester (9a) derivative have been synthesized from cleomiscosin A methyl ether. All the six derivatives were subjected to in silico QSAR modeling and docking studies and later the predicted results were confirmed through in vitro experiments. QSAR modeling results showed that compounds 6a and 9a possessed anti-inflammatory activity comparable or even higher than diclofenac sodium. Docking results revealed that compounds 9a and 6a showed very good anti-inflammatory activity due to low docking energies of viz., IL6 (-92.45 and -81.993 kcal mol(-1)), TNF-α (-94.992 and -69.235 kcal mol(-1)) and IL1β (-67.462 and -65.985 kcal mol(-1)). Further all the six novel derivatives were subjected for in vitro anti-inflammatory activity using primary macrophages cell culture bioassay system. At the initial doses of 1 μg/ml and 10 μg/ml, the pro-inflammatory cytokines (IL-1β, IL-6 and TNF-α) were quantified from cell culture supernatant using enzyme linked immunosorbent assay (ELISA). The in vitro effect of 6a-9a on cell viability in mouse peritoneal macrophage cells isolated from mice was evaluated using MTT assay. The in silico and in vitro data suggested that all the derivatives might be considered as potential anti-inflammatory drug-like molecules.

Title

QSAR, docking and in vitro studies for anti-inflammatory activity of cleomiscosin A methyl ether derivatives

Author

Shelly Sharma 1, Sunil Kumar Chattopadhyay, Dharmendra Kumar Yadav, Feroz Khan, Shilpa Mohanty, Anil Maurya, Dnyaneshwar Umrao Bawankule

Publish date

2012 Dec 18

PMID

21736704

Abstract

Natural coumarinolignoids isolated from the seeds of Cleome viscosa consist of a racemic mixture of cleomiscosins A, B and C. To screen out potential lead, anti-inflammatory activity of the isolated compounds was evaluated through molecular docking and QSAR studies by using reported in vivo activity of Swiss albino mice. Based on docking binding affinity, a possible mechanism of action has been hypothesized which constitute toll-like receptors (TLR-4), cluster of differentiation molecules (CDs), iNOS, COX-2 and STAT-6 proteins. It was very interesting to find that the 3D topology of the active site of COX-2 from the docking was in good agreement with QSAR model and in silico ADME/T parameters. A forward feed multiple linear regression model was developed with r(2) = 0.92 and rCV(2) = 0.87. This study showed that chemical descriptors, for example dipole vector-X, dipole vector-Y, steric energy, LUMO energy, size of smallest ring, size of largest ring and carboxyl group count, correlate reasonably well with experimental in vivo activity (logLD(50) ). QSAR study indicates that dipole vector-Y and carboxyl group count have negative correlation with activity. Cleomiscosins also showed compliance with 95% of in silico ADME/T properties of available drugs, e.g. serum protein binding, blood-brain barrier, CNS activity, HERG K+ channel activity, apparent Caco-2 permeability, apparent MDCK permeability, skin permeability and human oral absorption in GI. Besides, toxicity screening study suggests that cleomiscosin molecules possess no toxicity risk parameters. This study offer useful references for understanding and molecular design of inhibitors with improved anti-inflammatory activity.

© 2011 John Wiley & Sons A/S.

Title

In silico exploration of anti-inflammatory activity of natural coumarinolignoids

Author

Abha Meena 1, Dharmendra K Yadav, Ankit Srivastava, Feroz Khan, Debabrata Chanda, Sunil K Chattopadhyay

Publish date

2011 Oct;

PMID

20813432

Abstract

Six novel cleomiscosin A (a coumarino-lignoid), derivatives have been synthesized for the first time by using electrophilic substitution reaction to give nuclear nitrated and halogenated derivatives of cleomiscosin A in good yields. Structures of these compounds were established on the basis of IR, (1)H NMR, (13)C NMR and Mass spectral data. Some of the synthesized derivatives were tested for in-vitro target based anti-inflammatory study using primary macrophages cell culture bioassay system. The results showed that the compounds 1a, 3a and 4a (1 and 10 μg/mL) exhibited potent anti-inflammatory activity.

Copyright © 2010 Elsevier Masson SAS. All rights reserved.

Title

Synthesis and anti-inflammatory activity of derivatives of coumarino-lignoid, cleomiscosin A and its methyl ether

Author

Shelly Sharma 1, S K Chattopadhyay, Priyanka Trivedi, D U Bawankule

Publish date

2010 Nov