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8-O-Acetylharpagide

$202

  • Brand : BIOFRON

  • Catalogue Number : BD-D1317

  • Specification : 98%(HPLC)

  • CAS number : 6926-14-3

  • Formula : C17H26O11

  • Molecular Weight : 406.38

  • PUBCHEM ID : 9978650

  • Volume : 20MG

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Catalogue Number

BD-D1317

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8℃

Molecular Weight

406.38

Appearance

White crystalline powder

Botanical Source

Ajuga decumbens Thunb./Melittis melissophyllum and Ajuga reptans

Structure Type

Iridoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(=O)OC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)C

Synonyms

β-D-Glucopyranoside, (1S,4aS,5R,7S,7aS)-7-(acetyloxy)-1,4a,5,6,7,7a-hexahydro-4a,5-dihydroxy-7-methylcyclopenta[c]pyran-1-yl/6-Thio-8-propylthiotheophylline/(1S,4aS,5R,7S,7aS)-1-(β-D-Glucopyranosyloxy)-4a,5-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl acetate/8-O-acetyl-harpagide/Harpagide 7-acetyl/Uric acid,1,3-dimethyl-8-propylthio-6-thio/8-n-Propylthio-6-thiotheophyllin

IUPAC Name

[(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] acetate

Applications

8-O-Acetylharpagide is an iridoid isolated from Ajuga reptans with antitumoral, antiviral, antibacterial, and anti-inflammatory activities. 8-O-Acetylharpagide also has a biological activity on isolated smooth muscle preparations from guinea pig[1][2].

Density

1.6±0.1 g/cm3

Solubility

Methanol; Water

Flash Point

215.9±25.0 °C

Boiling Point

607.2±55.0 °C at 760 mmHg

Melting Point

227-229℃

InChl

InChI=1S/C17H26O11/c1-7(19)28-16(2)5-9(20)17(24)3-4-25-15(13(16)17)27-14-12(23)11(22)10(21)8(6-18)26-14/h3-4,8-15,18,20-24H,5-6H2,1-2H3/t8-,9-,10-,11+,12-,13-,14+,15+,16+,17-/m1/s1

InChl Key

CAFTUQNGDROXEZ-CDZVNVNZSA-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#:6926-14-3) 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

28028854

Abstract

INTRODUCTION:
Iridoid glycosides possess highly functionalised monoterpenoid aglycon with several contiguous stereocentres. For the most common, they are often present in quantities reaching several percentage of the fresh plant weight, and thus they may be regarded as starting material for the synthesis of a number of new chiral and bioactive molecules.

OBJECTIVE:
To quantify and to isolate 8-O-acetylharpagide (AH) from several extracts of Oxera coronata R.P.J. de Kok, a Lamiaceae species endemic to New Caledonia, using HPLC-ELSD (evaporative light scattering detector) and centrifugal partition chromatography (CPC).

METHODOLOGY:
Oxera coronata produces high amounts of AH in leaves, twigs and fruits. Water and methanol extracts of these plant parts were prepared. The content of AH in each extract was quantified by HPLC-ELSD, using acetonitrile-water (+0.1% formic acid) gradient elution. The HPLC method was validated for precision, linearity, limit of detection (LOD), limit of quantification (LOQ) and accuracy. A ternary solvent system ethyl acetate/n-propanol/water (3:2:5, v/v/v) was selected and applied to recover the target compound using Spot CPC from the leaves aqueous extract.

RESULTS:
HPLC-ELSD analysis followed by CPC purification led to the efficient isolation of AH from O. coronata leaves aqueous extract.

CONCLUSION:
HPLC-ELSD has proven to be a well-adapted detection and quantification method for iridoid glycosides, while CPC confirmed to be an efficient technique for the isolation of polar compounds. Copyright © 2016 John Wiley & Sons, Ltd.

Copyright © 2016 John Wiley & Sons, Ltd.

KEYWORDS

HPLC-ELSD; Lamiaceae; Oxera coronata; centrifugal partition chromatography; iridoid glycoside

Title

HPLC-ELSD Quantification and Centrifugal Partition Chromatography Isolation of 8-O-Acetylharpagide from Oxera coronata (Lamiaceae).

Author

Remeur C1, Le Borgne E1, Gauthier L2, Grougnet R2, Deguin B2, Poullain C1, Litaudon M1.

Publish date

2017 May

PMID

28012983

Abstract

Ajuga bracteosa Wall ex. Benth. (Lamiaceae) commonly known as Bungle Weed has been in use since ancient times and is mentioned Ayurvedic literature. The upper ground parts of the plant are used for treatment of various diseases. The weed is credited with astringent, febrifugal, stimulant, aperient, tonic, diuretic and depurative properties and is used for the treatment of gout and rheumatism, palsy and amenorrhoea. Two compounds 1) 14, 15-dihydroajugapitin and 2) 8-o-acetylharpagide were isolated from the aerial parts of the plant and tested for antibacterial activity against various pathogenic bacteria by agar well diffusion method. Compound 1 and 2 showed maximum antibacterial activity against Escherichia coli with zone of inhibitions of 25. 0 ± 1.4 mm and 22.6 ± 0.9 mm respectively. The MIC value of compound 1 and 2 ranged between 500 and 1000 μg/ml. It could be concluded that both compounds isolated from the aerial parts of Ajuga bracteosa possess antibacterial activity against pathogens.

Copyright © 2016 Elsevier Ltd. All rights reserved.

KEYWORDS

14, 15-Dihydroajugapitin; Ajuga bracteosa; Antibacterial; Human pathogens

Title

Antibacterial activity of 14, 15-dihydroajugapitin and 8-o-acetylharpagide isolated from Ajuga bracteosa Wall ex. Benth against human pathogenic bacteria.

Author

Ganaie HA1, Ali MN2, Ganai BA3, Meraj M4, Ahmad M5.

Publish date

2017 Feb

PMID

24066603

Abstract

8-O-acetylharpagide and harpagide are two kinds of effective component of Ajuga decumbens extract. A sensitive LC-MS/MS method has been established for pharmacokinetics of 8-O-acetylharpagide and harpagide in beagle dog after oral administration of from A. decumbens extract. Female beagle dogs received orally 12.9, 25.7 mg x kg(-1) p. o. Concentrations of 8-O-acetylharpagide and harpagide in plasma were determined by LC-MS/MS method at different time points and all pharmacokinetic parameters were estimated by non-compartment analysis. The mobile phase consisted of 0.1% formic acid in water (A) and acetonitrile (B), which was run at a flow rate of 0.3 mL x min(-1). Chromatographic separation was achieved on an Agilent ZORBAX XDB-C18 column (2.1 mm x 50 mm, 3.5 microm) using a gradient elution of 5% B at 0-2 min, 95% B at 2. 1-5 min and 5% B at 5. 1-10 min. All analytes, including the IS, were monitored under positive ionization conditions and quantified in MRM mode with transitions of m/z 429.2-369.2 for 8-O-acetylharpagide, m/z 387.2-207.2 for harpagide, and m/z 149.2-103.1 for IS. High purity nitrogen was employed as both the nebulizing and drying gas. Other parameters of the mass spectrometer were optimized as follows: drying gas flow 10.0 L x min(-1); drying gas temperature 300 degrees C; capillary voltage 4 000 V. Results showed that 8-O-acetylharpagide and harpagide showed a dose-dependence profile. T(max) of 8-O-acetylharpagide is 1.7 h, and T(max) of harpagide is 1.57 h, which was higher than T(max) of 8-O-acetylharpagide and harpagide after oral administration of from A. decumbens extract in rats. The different pharmacokinetic parameters may be due to the species differences of rat and beagle dog.

Title

[Pharmacokinetics of 8-O-acetylharpagide and harpagide after oral administration of Ajuga decumbens extract in beagle dog].

Author

Wen BY1, Li JR.

Publish date

2013 Jun