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Eupalinolide A

$225

  • Brand : BIOFRON

  • Catalogue Number : BF-E4001

  • Specification : 98%(HPLC)

  • CAS number : 877822-40-7

  • Formula : C24H30O9

  • Molecular Weight : 462.49

  • PUBCHEM ID : 77985550

  • Volume : 25mg

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Catalogue Number

BF-E4001

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

462.49

Appearance

White powder

Botanical Source

Eupatorium lindleyanum

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1=CC2C(C(CC(=CCC1OC(=O)C)COC(=O)C)OC(=O)C(=CCO)C)C(=C)C(=O)O2

Synonyms

2-Butenoic acid, 4-hydroxy-2-methyl-, (3aR,4R,6E,9S,10Z,11aR)-9-(acetyloxy)-6-[(acetyloxy)methyl]-2,3,3a,4,5,8,9,11a-octahydro-10-methyl-3-methylene-2-oxocyclodeca[b]furan-4-yl ester, (2E)-/Eupalinolide B/Eupalinolide A/(3aR,4R,6E,9S,10Z,11aR)-9-Acetoxy-6-(acetoxymethyl)-10-methyl-3-methylene-2-oxo-2,3,3a,4,5,8,9,11a-octahydrocyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-methyl-2-butenoate/Eupalinolide G/EupalinolideB/Eupalinolide-B

IUPAC Name

[9-acetyloxy-6-(acetyloxymethyl)-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 4-hydroxy-2-methylbut-2-enoate

Applications

Potential Anti-inflammatory Sesquiterpene Lactones from Eupatorium lindleyanum PUMID/DOI:DOI: 10.1055/s-0043-117742 Planta Med. 2018 Jan;84(2):123-128. Eupatorium lindleyanum has traditionally been used as folk medicine in Asian countries for its therapeutic effects on tracheitis and tonsillitis. Investigation of the anti-inflammatory active constituents from E. lindleyanum led to the isolation of two novel sesquiterpene lactones, named eupalinolide L (1) and eupalinolide M (2), and seven known sesquiterpene lactones (3 - 9). The structures and configurations of the new compounds were determined on the basis of spectroscopic analysis, especially 2D NMR techniques. In vivo experiments showed that the sesquiterpenes fraction significantly reduced mouse ear edema induced by xylene (18.6%, p < 0.05). In in vitro assays, compounds 1 - 9 showed excellent anti-inflammatory activities, as they lowered TNF- α and IL-6 levels in lipopolysaccharide-stimulated murine macrophage RAW 264.7 cells (p < 0.001). The above results suggest that the sesquiterpene lactones from E. lindleyanum can be developed as novel potential natural anti-inflammatory agents. ? Georg Thieme Verlag KG Stuttgart New York. Purification and characterization of HSP-inducers from Eupatorium lindleyanum PUMID/DOI:DOI: 10.1016/j.bcp.2011.12.040 Biochem Pharmacol. 2012 Apr 1;83(7):909-22. The expression of heat shock proteins (HSPs), particularly HSP70, provides resistance to stressors. We recently reported that ultraviolet (UV)-induced melanin production and skin damage were suppressed in transgenic mice expressing HSP70 and that an extract of Eupatorium lindleyanum induces the expression of HSP70 in cells. Here we report the purification of eupalinolide A and B (EA and EB) from E. lindleyanum, and describe their actions as HSP-inducers. EA and EB both induced the expression of HSP70 in cells at concentrations that did not significantly affect cell viability. Treatment of cells with EA or EB activated heat shock factor 1 (HSF1), while the artificial suppression of HSF1 expression diminished the EA- or EB-mediated induction of HSP70 expression. Furthermore, EB inhibited the interaction between HSF1 and HSP90, which is known to inhibit the activity of HSF1. These findings suggest that EA and EB induce the expression of HSP70 via the activation of HSF1 by inhibiting the interaction between HSF1 and HSP90. EA and EB both induced the expression of HSP70 synergistically with other stressors. Furthermore, pre-treatment of cells with EA or EB suppressed melanin production and stressor-induced apoptosis. These effects were suppressed by the artificial suppression of HSP70 expression. In vivo, the percutaneous administration of EB induced the expression of HSP70 and suppressed UVB radiation-induced damage, inflammatory responses and melanin production in the skin. These results suggest that EA and EB could be beneficial for use in cosmetics and medicines as a consequence of their inhibitory action on UV-induced skin damage and melanin production. ? 2012 Elsevier Inc. All rights reserved.

Density

1.24±0.1 g/cm3 (20 ºC 760 Torr)

Solubility

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

Flash Point

205.4±25.0 °C

Boiling Point

618.6±55.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C24H30O9/c1-13(8-9-25)23(28)32-21-11-18(12-30-16(4)26)6-7-19(31-17(5)27)14(2)10-20-22(21)15(3)24(29)33-20/h6,8,10,19-22,25H,3,7,9,11-12H2,1-2,4-5H3/b13-8+,14-10+,18-6+/t19-,20+,21-,22-/m0/s1

InChl Key

HPWMABTYJYZFLK-GOMZETCQSA-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#:877822-40-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

26011510

Abstract

A simple, selective, and sensitive LC/MS/MS method was developed and validated for simultaneous determination of eupalinolide A, eupalinolide B, and hyperoside in rat plasma. Plasma samples were processed by protein precipitation with acetonitrile. The three analytes, together with internal standard (IS, lysionotin), were separated on a Venusil MP-C18 column (50mm×2.1mm, 3μm) using a mobile phase of methanol and 10mM ammonium acetate (45:55, v/v) with isocratic elution. Mass spectrometric detection was performed by multiple-reaction monitoring mode via electrospray ionization source. Linear calibration curves were obtained for the following concentration range: 1.28-640ng/mL for EA; 1.98-990ng/mL for EB; and 2.00-1000ng/mL for HYP. The intra- and inter-day precision was less than 10.25%, and the accuracy was between 89.16% and 110.63%. The extraction recovery of the analytes and IS from rat plasma was above 88.75%. The validated method has been successfully applied to pharmacokinetic studies of the three analytes following intragastric administration of Eupatorium lindleyanum extract at a single dose of 100, 250, and 625mg/kg to Sprague-Dawley rats, respectively. The pharmacokinetic results may help to better understand the pharmacological actions of the herb E. lindleyanum.

Copyright © 2015 Elsevier B.V. All rights reserved.

KEYWORDS

Eupalinolide; Eupatorium lindleyanum; Hyperoside; LC/MS/MS; Pharmacokinetic study

Title

Pharmacokinetics of eupalinolide A, eupalinolide B and hyperoside from Eupatorium lindleyanum in rats by LC/MS/MS.

Author

Zhang J1, Zhao F2, Yu X2, Lu X2, Zheng G2.

Publish date

2015 Jul 15