Catalogue Number
BF-A4015
Analysis Method
HPLC,NMR,MS
Specification
98%(HPLC)
Storage
-20℃
Molecular Weight
312.32
Appearance
White crystalline powder
Botanical Source
Vitex trifolia
Structure Type
Terpenoids
Category
Standards;Natural Pytochemical;API
SMILES
C1=COC(C2C1C(C=C2COC(=O)C3=CC=C(C=C3)O)O)OC4C(C(C(C(O4)CO)O)O)O
Synonyms
Benzoic acid, 4-hydroxy-, [(1S,4aR,5S,7aS)-1-(β-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-5-hydroxycyclopenta[c]pyran-7-yl]methyl ester/[(1S,4aR,5S,7aS)-1-(β-D-Glucopyranosyloxy)-5-hydroxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate/[(1S,4aR,5S,7aS)-1-(β-D-Glucopyranosyloxy)-5-hydroxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyr-7-yl]methyl-4-hydroxybenzoat/[(1S,4aR,5S,7aS)-5-Hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-1,4a,5,7a-tetrahydrocyclopenta[c]pyr-7-yl]methyl-4-hydroxybenzoat/[(1S,4aR,5S,7aS)-5-Hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate/unii-jb24q0ot9g/4-Hydroxybenzoate de [(1S,4aR,5S,7aS)-5-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyle/Agnuside
IUPAC Name
[(1S,4aR,5S,7aS)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate
Density
1.6±0.1 g/cm3
Solubility
Methanol; DMF
Flash Point
273.5±26.4 °C
Boiling Point
785.5±60.0 °C at 760 mmHg
Melting Point
134-136ºC
InChl
InChI=1S/C22H26O11/c23-8-15-17(26)18(27)19(28)22(32-15)33-21-16-11(7-14(25)13(16)5-6-30-21)9-31-20(29)10-1-3-12(24)4-2-10/h1-7,13-19,21-28H,8-9H2/t13-,14+,15+,16+,17+,18-,19+,21-,22-/m0/s1
InChl Key
GLACGTLACKLUJX-QNAXTHAFSA-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#:11027-63-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate
MSDS
30340142
Due to its important role in regulating angiogenesis, vascular homeostasis and remodeling, and arteriogenesis in blood vascular and lymphatic endothelial cells, VEGFR2 stimulation has demonstrated promise in preclinical studies as an endovascular treatment for ischemic myocardial and peripheral disease. However, the short half-life of protein- and cytokine-based strategies and transduction inefficiency of vector-based modalities have hindered its clinical therapeutic applications. In the present study, we used a streamlined bioinformatics strategy combining ligand-based pharmacophore development and validation, virtual screening, and molecular docking to identify agnuside, a non-toxic, natural small molecule extract of Vitex agnus-castus possessing strong binding affinity, druggable physiochemical properties, and conformationally stable hydrogen bond and hydrophobic interactions with catalytically important residues within VEGFR2’s active and allosteric sites. In-vitro proliferation, tube formation, and scratch wound migration assays provide evidence that agnuside promotes endothelial cell angiogenesis. Agnuside increases HUVEC proliferation with an EC50 of 1.376 μg/mL, stimulates tubulogenesis dose-dependently, and increases scratch wound migration rate. An additional angiogenesis assay suggests that agnuside may actively compete with a VEGFR2 inhibitor for VEGFR2 binding site occupancy to increase total length and branching length of HUVEC tubular networks. Chemometric analysis of molecular interaction fields (MIFs) by partial least squares (PLS)-derived quantitative structure activity relationship (QSAR) analysis and MIF contours provides the framework for the formulation of agnuside analogues possessing greater potency. Our research supports that agnuside may be a lead molecule for therapeutic angiogenesis.
Agnuside; Agonist; Drug discovery; Molecular modeling; QSAR; Therapeutic angiogenesis.
Identification and Characterization of Agnuside, a Natural Proangiogenic Small Molecule
Piyush Pillarisetti 1 , Kenneth A Myers 2
2018 Dec 5
29403861
A high performance liquid chromatography coupled with photodiode array detection method was developed for the identification and quantification of p-hydroxy benzoic acid and agnuside in the extracts of Vitex negundo and Vitex trifolia. The separation was achieved using acetonitrile and O-phosphoric acid-water (0.5%, v/v) as the mobile phase in an isocratic elution mode. Mean retention times of standard p-hydroxy benzoic acid and agnuside were 6.14 and 11.90 min respectively. The developed method was validated as per the ICH guidelines for limit of detection, limit of quantification, linearity, accuracy and precision. Good linearity (r2≥0.999) was observed for both the compounds in wide concentration range. Relative standard deviation values for intra-day and inter-day precision studies were less than 2%. The analytical recoveries of p-hydroxy benzoic acid and agnuside by the developed HPLC method were 93.07% and 106.11% respectively. Two compounds were identified and quantified in leaves and bar extracts of V. negundo and V. trifolia using the developed HPLC method.
Agnuside; HPLC-PDA; Vitex negundo; Vitex trifolia; p-Hydroxy benzoic acid.
Validated HPLC Method for Identification and Quantification of p-hydroxy Benzoic Acid and Agnuside in Vitex negundo and Vitex trifolia
Sonal Shah 1 , Tushar Dhanani 1 , Satyanshu Kumar 1
2013 Dec
27018507
Agnuside (AGN), an iridoid glycoside, is the chemotaxonomic marker of the genus Vitex which has gained enormous attention by virtue of its potential health benefits. Regardless of claiming many therapeutic applications reports demonstrating its pharmacokinetics or quantification in biomatrices are lacking. This is the first report which presents a sensitive liquid chromatography coupled to a tandem mass spectrometry (LC-MS/MS) method for the quantification of AGN in mice plasma and various tissues (including liver, intestine, spleen, kidney, heart, lungs and brain). AGN was extracted from the biological samples using protein precipitation followed by liquid-liquid extraction and the separation was achieved on C18 reversed phase column with a mobile phase consisted of 0.1% formic acid in acetonitrile-0.1% formic acid in triple distilled water (92:8, v/v) at a flow rate of 0.7mL/min. The MS/MS detection was performed by electrospray ionization (ESI) using multiple reaction monitoring (MRM) in negative scan mode. The bioanalytical method was found linear over the concentration range of 1-4000ng/mL for plasma and tissue homogenates (r(2)≥0.990). The lower limit of quantitation (LLOQ) for all matrices was 1ng/mL. Intra-day and inter-day variance and accuracy ranged from 90 to 110% and 1-10%, respectively. Matrix effect and recoveries were well within the satisfactory limits. The validated method was applied successfully to measure AGN concentrations in plasma and tissues following intravenous (i.v.) and peroral (p.o.) administration to mice. Maximal AGN concentrations in plasma and tissues were reached within 30-45min. The mean absolute bioavailability (%F) of AGN was∼0.7%. After oral administration, AGN was most abundant in intestine, followed by kidney, liver, spleen, brain, lungs and heart. The identified target tissues of AGN may help in understanding its pharmacological action in vivo.
Agnuside; Bioavailability; Chaste tree berry; LC-MS/MS; Pharmacokinetics; Tissue distribution.
Plasma Pharmacokinetics, Bioavailability and Tissue Distribution of Agnuside Following Peroral and Intravenous Administration in Mice Using Liquid Chromatography Tandem Mass Spectrometry
Rachumallu Ramakrishna 1 , Manisha Bhateria 1 , Rajbir Singh 1 , Santosh Kumar Puttrevu 1 , Rabi Sankar Bhatta 2
2016 Jun 5
Description :
Agnuside is a compound isolated from Vitex negundo, down-regulates pro-inflammatory mediators PGE2 and LTB4, and reduces the expression of cytokines, with anti-arthritic activity[1].
