Agnuside - CAS 11027-63-7
Catalog number:
11027-63-7
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C22H26O11
Molecular Weight:
466.44
COA:
Inquire
Targets:
Others
Description:
Agnuside is an iridoid glycoside found in the herbs of Vitex agnus-castus, a plant native to the Mediterranean region. It is the ester of aucubin and p-hydroxybenzoic acid. It showed inhibition of vascular permeability and leukocyte migration in vivo. It has been used in various applications including in the treatment of premenstrual syndrome and regulation of menopause symptoms. It exhibits estrogen-like activities as it interacts with estrogen receptors (ER-alpha) and estrogen receptor-regulated pregesterone receptors. It has anti-arthritic activity and may be used as a therapeutic agent in the treatment of arthritis by the modulation of the host immune response.
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Purity:
>98%
Appearance:
Yellow Oil
Synonyms:
[(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;Chasteberry oil;[(1R,2S,6S,7S)-7-Hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxabicyclo[4.3.0]nona-4,8-dien-9-yl]methyl 4-hydroxybenzoate;Vitex Oil
Solubility:
10 mM in DMSO
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
Agnuside has been used in various applications including in the treatment of premenstrual syndrome and regulation of menopause symptoms. It has anti-arthritic activity and may be used as a therapeutic agent in the treatment of arthritis.
Quality Standard:
CP standard
Shelf Life:
2 month in rt, long time
Quantity:
Grams to Kilograms
Boiling Point:
785.5±60.0 °C | Condition: Press: 760 Torr
Melting Point:
146 °C
Density:
1.59±0.1 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
InChIKey:
GLACGTLACKLUJX-QNAXTHAFSA-N
InChI:
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
Canonical SMILES:
C1=COC(C2C1C(C=C2COC(=O)C3=CC=C(C=C3)O)O)OC4C(C(C(C(O4)CO)O)O)O
1.Identification and quantification of phenolic compounds in Vitex negundo L. var. cannabifolia (Siebold et Zucc.) Hand.-Mazz. using liquid chromatography combined with quadrupole time-of-flight and triple quadrupole mass spectrometers.
Huang M1, Zhang Y2, Xu S3, Xu W3, Chu K3, Xu W4, Zhao H5, Lu J6. J Pharm Biomed Anal. 2015 Apr 10;108:11-20. doi: 10.1016/j.jpba.2015.01.049. Epub 2015 Feb 7.
A high performance liquid chromatography combined with quadrupole time-of-flight mass spectrometry method was developed for the identification of phenolic compounds in Vitex negundo L. var. cannabifolia (Siebold et Zucc.) Hand.-Mazz. A total of 31 compounds (10 phenolic acids, 19 flavonoids, and 2 iridoids) were fully or partially identified. Caffeic acid, neochlorogenic acid, cryptochlorogenin acid, isochlorogenic acid B, isochlorogenic acid A, isochlorogenic acid C, schaftoside, isoschaftoside, flavosativaside, vitexin 2"-rhamnoside, and kaempferol 3-(6"-malonylglucoside) were detected for the first time in this plant. In subsequent quantitative analysis, an ultra-performance liquid chromatography combined with triple quadrupole mass spectrometry method was developed for the quantitative analysis of 17 phenolic compounds. All the analytes were detected within 8 min. The limits of detection and quantification were less than 7.251 and 26.
2.Development and validation of a rapid ultra-high performance liquid chromatography diode array detector method for Vitex agnus-castus.
Högner C1, Sturm S, Seger C, Stuppner H. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 May 15;927:181-90. doi: 10.1016/j.jchromb.2013.02.037. Epub 2013 Mar 4.
A rapid ultra-high performance liquid chromatography diode array detector (UHPLC-DAD) method was developed and validated for the simultaneous determination of all classes of non-volatile phytochemicals (iridoids, flavonoids and diterpenes) in Vitex agnus-castus (Lamiaceae) fruits, a traditional medicinal plant used against premenstrual symptoms (PMS) and other disorders. Seven marker compounds, 3,4-dihydroxybenzoic acid, p-hydroxybenzoic acid, agnuside, 5-hydroxykaempferol-3,6,7,4'-tetramethylether, 1,2-dibenzoic acid glucose, methoxy-vitexilactone, and vitetrifolin D were isolated from the methanol extract of V. agnus-castus to be used as reference substances. Chromatographic separation was performed on a Zorbax Eclipse XDB-C18 (50mm×2.1mm) UHPLC column with 1.8μm particle size, within 20min. A solvent gradient from 0.5% acetic acid to acetonitrile at a flow rate of 0.6mL/min was used as mobile phase. Analyte detection and quantification was realized at 210nm and 260nm.
3.Quality evaluation of medicinal products and health foods containing chaste berry (Vitex agnus-castus) in Japanese, European and American markets.
Fukahori M1, Kobayashi S, Naraki Y, Sasaki T, Oka H, Seki M, Masada-Atsumi S, Hakamatsuka T, Goda Y. Chem Pharm Bull (Tokyo). 2014;62(4):379-85.
The aim of present study was to evaluate the qualities of chaste berry (fruit of Vitex agnus-castus L.) preparations using HPLC fingerprint analysis. Seven medicinal products 1 from Japan and 6 from Europe, and 17 health foods, 6 from Japan and 11 from the United States were analyzed. HPLC profile and 26 authentic peaks were compared medicinal products and health foods. Whereas medicinal products had similar HPLC profiles, health foods had various profiles and each peak was also greatly different. The measured amounts of two markers in 5 traditional medicinal products, agnuside and casticin specified in the European Pharmacopoeia (EP), the U.S. Pharmacopoeia (USP) or the WHO monographs of chaste berry, were much lower than those in 2 medicinal products defined as "well-established use" by the European Medicines Agency. The amounts of two markers for 17 health foods differed in a great deal from 14-5054% and 3-1272%, respectively. Furthermore the amount ratios of two markers, agnuside/casticin, in about half of the health foods were remarkably larger than the standard crude drug and the ratios were closer to one of the related Chinese herbs, Vitex negundo L.
4.Plasma pharmacokinetics, bioavailability and tissue distribution of agnuside following peroral and intravenous administration in mice using liquid chromatography tandem mass spectrometry.
Ramakrishna R1, Bhateria M1, Singh R1, Puttrevu SK1, Bhatta RS2. J Pharm Biomed Anal. 2016 Mar 2;125:154-164. doi: 10.1016/j.jpba.2016.02.047. [Epub ahead of print]
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.
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CAS 11027-63-7 Agnuside

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