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MedKoo Cat#: 600103 | Name: Agnuside
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Agnuside is a chemical compound found in Vitex agnus-castus. Agnuside is the ester of aucubin and p-hydroxybenzoic acid.

Chemical Structure

Agnuside
CAS#11027-63-7

Theoretical Analysis

MedKoo Cat#: 600103

Name: Agnuside

CAS#: 11027-63-7

Chemical Formula: C22H26O11

Exact Mass: 466.1475

Molecular Weight: 466.44

Elemental Analysis: C, 56.65; H, 5.62; O, 37.73

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 650.00 2 Weeks
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Related CAS #
No Data
Synonym
Agnuside.
IUPAC/Chemical 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
InChi Key
GLACGTLACKLUJX-QNAXTHAFSA-N
InChi Code
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
SMILES Code
O=C(OCC1=C[C@@H](O)[C@@]2([H])[C@]1([H])[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)OC=C2)C4=CC=C(O)C=C4
Appearance
XXXX solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
An iridoid glycoside with diverse biological activities.
In vitro activity:
HUVEC proliferation in the presence of all tested agnuside concentrations (1–2500 ng/mL) at all time points (24–96 hrs.) was markedly higher than in DMSO control. Up to a 56% increase in HUVEC proliferation was measured for 2500 ng/mL agnuside treatment at 96 hrs., compared to a 20–30% increase for 24–72 hrs., shown in Fig. 8a. No differences in cell morphology were observed for any treatments. Agnuside promoted formation of meshes in a dose-dependent manner. Total length and total branching length of 0.1 ng/mL agnuside-treated HUVEC tubular networks were greater than DMSO control. Even in the presence of 1 nM ZM 323881 HCl, 0.1 ng/mL agnuside resulted in greater total length and total branching length compared to DMSO control. The data may suggest that agnuside exerts a proangiogenic effect on HUVECs by competing with ZM 323881 HCl for VEGFR2 binding site occupancy. As shown in Fig. 8g, HUVEC wound closure 24 hrs. after initial scratch wound application was accentuated in the presence of 100 ng/mL agnuside relative to control. Reference: Eur J Med Chem. 2018 Dec 5; 160: 193–206. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6287603/
In vivo activity:
To evaluate the effect of AGN (Agnuside) on synovial fibrosis in KOA, anatomical characteristics and pathological sections of synovial tissue were observed. The KOA group showed markedly increased collagen deposition, while this change was relatively lessened in the KOA+AGN group observed under anatomy (Figure 3(a)). The same results can be observed by Sirius Red staining (Figure 3(b)). Subsequently, this study performed a semiquantitative analysis by immunohistochemical staining of type I collagen (Figures 3(c) and 3(d)). In the KOA group, the percentage of collagen I-positive areas was significantly higher in comparison with the normal group (P < 0.05). But in the KOA+AGN group, collagen I deposition was significantly alleviated compared with the KOA group (P < 0.05). More specifically, this study measured both mRNA and protein expressions of fibrotic markers TGF-β, TIMP1, and VEGF in synovial tissues (Figures 3(e)–3(g)). This study found that there was a significant decrease level of profibrotic substances in the KOA+AGN group. Reference: Mediators Inflamm. 2021; 2021: 5534614. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7987448/
Solvent mg/mL mM comments
Solubility
DMSO 10.0 21.44
DMF 10.0 21.44
Ethanol 0.5 45.96
PBS (pH 7.2) 0.2 0.43
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 466.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Pillarisetti P, Myers KA. Identification and characterization of agnuside, a natural proangiogenic small molecule. Eur J Med Chem. 2018 Dec 5;160:193-206. doi: 10.1016/j.ejmech.2018.10.009. Epub 2018 Oct 5. PMID: 30340142; PMCID: PMC6287603. 2. Zhang L, Li X, Zhang H, Huang Z, Zhang N, Zhang L, Xing R, Wang P. Agnuside Alleviates Synovitis and Fibrosis in Knee Osteoarthritis through the Inhibition of HIF-1α and NLRP3 Inflammasome. Mediators Inflamm. 2021 Mar 16;2021:5534614. doi: 10.1155/2021/5534614. PMID: 33814979; PMCID: PMC7987448. 3. Pandey A, Bani S, Satti NK, Gupta BD, Suri KA. Anti-arthritic activity of agnuside mediated through the down-regulation of inflammatory mediators and cytokines. Inflamm Res. 2012 Apr;61(4):293-304. doi: 10.1007/s00011-011-0410-x. Epub 2012 Jan 8. PMID: 22228102.
In vitro protocol:
1. Pillarisetti P, Myers KA. Identification and characterization of agnuside, a natural proangiogenic small molecule. Eur J Med Chem. 2018 Dec 5;160:193-206. doi: 10.1016/j.ejmech.2018.10.009. Epub 2018 Oct 5. PMID: 30340142; PMCID: PMC6287603.
In vivo protocol:
1. Zhang L, Li X, Zhang H, Huang Z, Zhang N, Zhang L, Xing R, Wang P. Agnuside Alleviates Synovitis and Fibrosis in Knee Osteoarthritis through the Inhibition of HIF-1α and NLRP3 Inflammasome. Mediators Inflamm. 2021 Mar 16;2021:5534614. doi: 10.1155/2021/5534614. PMID: 33814979; PMCID: PMC7987448. 2. Pandey A, Bani S, Satti NK, Gupta BD, Suri KA. Anti-arthritic activity of agnuside mediated through the down-regulation of inflammatory mediators and cytokines. Inflamm Res. 2012 Apr;61(4):293-304. doi: 10.1007/s00011-011-0410-x. Epub 2012 Jan 8. PMID: 22228102.
1: Zhang L, Li X, Zhang H, Huang Z, Zhang N, Zhang L, Xing R, Wang P. Agnuside Alleviates Synovitis and Fibrosis in Knee Osteoarthritis through the Inhibition of HIF-1α and NLRP3 Inflammasome. Mediators Inflamm. 2021 Mar 16;2021:5534614. doi: 10.1155/2021/5534614. PMID: 33814979; PMCID: PMC7987448. 2: Tirpude NV, Sharma A, Bhardwaj N. Agnuside mitigates OVA-LPS induced perturbed lung homeostasis via modulating inflammatory, autophagy, apoptosis- fibrosis response and myeloid lineages in mice model of allergic asthma. Int Immunopharmacol. 2022 May;106:108579. doi: 10.1016/j.intimp.2022.108579. Epub 2022 Feb 7. PMID: 35144202. 3: Pillarisetti P, Myers KA. Identification and characterization of agnuside, a natural proangiogenic small molecule. Eur J Med Chem. 2018 Dec 5;160:193-206. doi: 10.1016/j.ejmech.2018.10.009. Epub 2018 Oct 5. PMID: 30340142; PMCID: PMC6287603. 4: Singh PP, Bhunia D, Verma YK, Sidiq T, Khajuria A, Guptha A, Pallavi MP, Vamshi SS, Qazi GN, Kumar HM. Synthesis of novel lipidated iridoid glycosides as vaccine adjuvants: 6-O-palmitoyl Agnuside elicit strong Th1 and Th2 response to ovalbumin in mice. Int Immunopharmacol. 2013 Nov;17(3):593-600. doi: 10.1016/j.intimp.2013.07.018. Epub 2013 Aug 14. PMID: 23954198. 5: Pandey A, Bani S, Satti NK, Gupta BD, Suri KA. Anti-arthritic activity of agnuside mediated through the down-regulation of inflammatory mediators and cytokines. Inflamm Res. 2012 Apr;61(4):293-304. doi: 10.1007/s00011-011-0410-x. Epub 2012 Jan 8. PMID: 22228102. 6: Shah S, Dhanani T, Kumar S. Validated HPLC method for identification and quantification of p-hydroxy benzoic acid and agnuside in Vitex negundo and Vitex trifolia. J Pharm Anal. 2013 Dec;3(6):500-508. doi: 10.1016/j.jpha.2013.09.008. Epub 2013 Oct 5. PMID: 29403861; PMCID: PMC5761016. 7: Ramakrishna R, Bhateria M, Singh R, Puttrevu SK, Bhatta RS. Plasma pharmacokinetics, bioavailability and tissue distribution of agnuside following peroral and intravenous administration in mice using liquid chromatography tandem mass spectrometry. J Pharm Biomed Anal. 2016 Jun 5;125:154-64. doi: 10.1016/j.jpba.2016.02.047. Epub 2016 Mar 2. PMID: 27018507. 8: Le DD, Han S, Yu J, Ahn J, Kim CK, Lee M. Iridoid derivatives from Vitex rotundifolia L. f. with their anti-inflammatory activity. Phytochemistry. 2023 Jun;210:113649. doi: 10.1016/j.phytochem.2023.113649. Epub 2023 Mar 22. PMID: 36963708. 9: Yang XY, Gao PY, Chen XX, Wang LX, Jiang T, Wu T, Chen YY, Yue CY, Wu HW, Tang LY, Wang ZJ. [Comparison of HPLC fingerprints and determination of main components of Viticis Fructus from different species]. Zhongguo Zhong Yao Za Zhi. 2023 May;48(9):2471-2479. Chinese. doi: 10.19540/j.cnki.cjcmm.20230104.201. PMID: 37282876. 10: Suksamrarn A, Kumpun S, Kirtikara K, Yingyongnarongkul B, Suksamrarn S. Iridoids with anti-inflammatory activity from Vitex peduncularis. Planta Med. 2002 Jan;68(1):72-3. doi: 10.1055/s-2002-20048. PMID: 11842334. 11: Högner C, Sturm S, Seger C, Stuppner H. Development and validation of a rapid ultra-high performance liquid chromatography diode array detector method for Vitex agnus-castus. 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. PMID: 23522912. 12: Chen X, Wang X, Ma L, Fang S, Li J, Boadi EO, He J, Gao XM, Wang Y, Chang YX. The network pharmacology integrated with pharmacokinetics to clarify the pharmacological mechanism of absorbed components from Viticis fructus extract. J Ethnopharmacol. 2021 Oct 5;278:114336. doi: 10.1016/j.jep.2021.114336. Epub 2021 Jun 15. PMID: 34139282. 13: Sogame M, Naraki Y, Sasaki T, Seki M, Yokota K, Masada S, Hakamatsuka T. Quality Assessment of Medicinal Product and Dietary Supplements Containing Vitex agnus-castus by HPLC Fingerprint and Quantitative Analyses. Chem Pharm Bull (Tokyo). 2019;67(6):527-533. doi: 10.1248/cpb.c18-00725. PMID: 31155557. 14: Hu Y, Hou TT, Zhang QY, Xin HL, Zheng HC, Rahman K, Qin LP. Evaluation of the estrogenic activity of the constituents in the fruits of Vitex rotundifolia L. for the potential treatment of premenstrual syndrome. J Pharm Pharmacol. 2007 Sep;59(9):1307-12. doi: 10.1211/jpp.59.9.0016. PMID: 17883902. 15: Fukahori M, Kobayashi S, Naraki Y, Sasaki T, Oka H, Seki M, Masada-Atsumi S, Hakamatsuka T, Goda Y. Quality evaluation of medicinal products and health foods containing chaste berry (Vitex agnus-castus) in Japanese, European and American markets. Chem Pharm Bull (Tokyo). 2014;62(4):379-85. doi: 10.1248/cpb.c13-00588. PMID: 24695348. 16: Julius A, Renuka RR, Hopper W, Babu Raghu P, Rajendran S, Srinivasan S, Dharmalingam K, Alanazi AM, Arokiyaraj S, Prasath S. Inhibition of Aldose Reductase by Novel Phytocompounds: A Heuristic Approach to Treating Diabetic Retinopathy. Evid Based Complement Alternat Med. 2022 Mar 21;2022:9624118. doi: 10.1155/2022/9624118. PMID: 35356240; PMCID: PMC8959960. 17: Venditti A, Frezza C, Foddai S, Serafini M, Nicoletti M, Bianco A. Chemical Traits of Hemiparasitism in Odontites luteus. Chem Biodivers. 2017 Apr;14(4). doi: 10.1002/cbdv.201600416. Epub 2017 Mar 23. PMID: 27997755. 18: Csupor D, Boros K, Hohmann J. Low potency homeopathic remedies and allopathic herbal medicines: is there an overlap? PLoS One. 2013 Sep 3;8(9):e74181. doi: 10.1371/journal.pone.0074181. PMID: 24019954; PMCID: PMC3760822. 19: Najar IA, Sachin BS, Sharma SC, Satti NK, Suri KA, Johri RK. Modulation of P-glycoprotein ATPase activity by some phytoconstituents. Phytother Res. 2010 Mar;24(3):454-8. doi: 10.1002/ptr.2951. PMID: 19653312. 20: Kuruüzüm-Uz A, Ströch K, Demirezer LO, Zeeck A. Glucosides from Vitex agnus- castus. Phytochemistry. 2003 Aug;63(8):959-64. doi: 10.1016/s0031-9422(03)00285-1. PMID: 12895546.

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