Verproside | CAS#50932-20-2 | iridoid

MedKoo Cat#: 145662 | Name: Verproside

Description:

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

Verproside is an iridoid. Verproside shows anti-inflammatory effects on a broad range of airway stimulants in NCI-H292 cells.

Chemical Structure

Verproside

CAS#50932-20-2

Theoretical Analysis

MedKoo Cat#: 145662

Name: Verproside

CAS#: 50932-20-2

Chemical Formula: C22H26O13

Exact Mass: 498.1400

Molecular Weight: 498.44

Elemental Analysis: C, 53.01; H, 5.26; O, 41.73

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Verproside;

IUPAC/Chemical Name

(1aS,1bS,2S,5aR,6S,6aS)-1a-(hydroxymethyl)-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1a,1b,2,5a,6,6a-hexahydrooxireno[2',3':4,5]cyclopenta[1,2-c]pyran-6-yl 3,4-dihydroxybenzoate

InChi Key

DBUOUVZMYWYRRI-YWEKDMGLSA-N

InChi Code

1S/C22H26O13/c23-6-12-14(27)15(28)16(29)21(32-12)34-20-13-9(3-4-31-20)17(18-22(13,7-24)35-18)33-19(30)8-1-2-10(25)11(26)5-8/h1-5,9,12-18,20-21,23-29H,6-7H2/t9-,12-,13-,14-,15+,16-,17+,18+,20+,21+,22-/m1/s1

SMILES Code

[H][C@@]12C=CO[C@@H](O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@]1([H])[C@@]4(CO)O[C@H]4[C@H]2OC(=O)C5=CC=C(O)C(O)=C5

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 498.44 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.

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

1: Oh ES, Ryu HW, Kim MO, Lee JW, Song YN, Park JY, Kim DY, Ro H, Lee J, Kim TD, Hong ST, Lee SU, Oh SR. Verproside, the Most Active Ingredient in YPL-001 Isolated from Pseudolysimachion rotundum var. subintegrum, Decreases Inflammatory Response by Inhibiting PKCδ Activation in Human Lung Epithelial Cells. Int J Mol Sci. 2023 Apr 13;24(8):7229. doi: 10.3390/ijms24087229. PMID: 37108390; PMCID: PMC10138391. 2: Lee SU, Sung MH, Ryu HW, Lee J, Kim HS, In HJ, Ahn KS, Lee HJ, Lee HK, Shin DH, Lee Y, Hong ST, Oh SR. Verproside inhibits TNF-α-induced MUC5AC expression through suppression of the TNF-α/NF-κB pathway in human airway epithelial cells. Cytokine. 2016 Jan;77:168-75. doi: 10.1016/j.cyto.2015.08.262. Epub 2015 Aug 28. PMID: 26318254. 3: Kim MG, Hwang DK, Jeong HU, Ji HY, Oh SR, Lee Y, Yoo JS, Shin DH, Lee HS. In vitro and in vivo metabolism of verproside in rats. Molecules. 2012 Oct 12;17(10):11990-2002. doi: 10.3390/molecules171011990. PMID: 23085650; PMCID: PMC6268120. 4: Park EJ, Lee HS, Oh SR, Lee HK, Lee HS. Pharmacokinetics of verproside after intravenous and oral administration in rats. Arch Pharm Res. 2009 Apr;32(4):559-64. doi: 10.1007/s12272-009-1412-x. Epub 2009 Apr 29. PMID: 19407974. 5: Jung S, Woo SY, Park MH, Kim DY, Lee SU, Oh SR, Kim MO, Lee J, Ryu HW. Potent inhibition of human tyrosinase inhibitor by verproside from the whole plant of Pseudolysimachionrotundum var. subintegrum. J Enzyme Inhib Med Chem. 2023 Dec;38(1):2252198. doi: 10.1080/14756366.2023.2252198. PMID: 37649388; PMCID: PMC10472861. 6: Oh SR, Lee MY, Ahn K, Park BY, Kwon OK, Joung H, Lee J, Kim DY, Lee S, Kim JH, Lee HK. Suppressive effect of verproside isolated from Pseudolysimachion longifolium on airway inflammation in a mouse model of allergic asthma. Int Immunopharmacol. 2006 Jun;6(6):978-86. doi: 10.1016/j.intimp.2006.01.010. Epub 2006 Feb 10. PMID: 16644484. 7: Kim JH, Hwang DK, Moon JY, Lee Y, Yoo JS, Shin DH, Lee HS. Multiple UDP- Glucuronosyltransferase and Sulfotransferase Enzymes are Responsible for the Metabolism of Verproside in Human Liver Preparations. Molecules. 2017 Apr 22;22(4):670. doi: 10.3390/molecules22040670. PMID: 28441724; PMCID: PMC6154560. 8: Park EJ, Oh SR, Lee HK, Lee HS. Liquid chromatography-mass spectrometry for the simultaneous determination of the catalpol-related iridoid glucosides, verproside, isovanilloylcatalpol, catalposide and 6-O-veratroyl catalpol in rat plasma. Biomed Chromatogr. 2009 Sep;23(9):980-6. doi: 10.1002/bmc.1211. PMID: 19353737. 9: Saracoglu I, Harput US. In vitro cytotoxic activity and structure activity relationships of iridoid glucosides derived from Veronica species. Phytother Res. 2012 Jan;26(1):148-52. doi: 10.1002/ptr.3546. Epub 2011 Jun 16. PMID: 21678519. 10: Küpeli E, Harput US, Varel M, Yesilada E, Saracoglu I. Bioassay-guided isolation of iridoid glucosides with antinociceptive and anti-inflammatory activities from Veronica anagallis-aquatica L. J Ethnopharmacol. 2005 Nov 14;102(2):170-6. doi: 10.1016/j.jep.2005.05.042. Epub 2005 Jul 12. PMID: 16019176. 11: Lu Q, Sun Y, Shu Y, Tan S, Yin L, Guo Y, Tang L. HSCCC Separation of the Two Iridoid Glycosides and Three Phenolic Compounds from Veronica ciliata and Their in Vitro Antioxidant and Anti-Hepatocarcinoma Activities. Molecules. 2016 Sep 15;21(9):1234. doi: 10.3390/molecules21091234. PMID: 27649125; PMCID: PMC6273391. 12: Harput US, Saracoglu I, Inoue M, Ogihara Y. Phenylethanoid and iridoid glycosides from Veronica persica. Chem Pharm Bull (Tokyo). 2002 Jun;50(6):869-71. doi: 10.1248/cpb.50.869. PMID: 12045353. 13: Albach DC, Gotfredsen CH, Jensen SR. Iridoid glucosides of Paederota lutea and the relationships between Paederota and Veronica. Phytochemistry. 2004 Jul;65(14):2129-34. doi: 10.1016/j.phytochem.2004.05.022. PMID: 15279984. 14: Mantovska DI, Zhiponova MK, Georgiev MI, Grozdanova T, Gerginova D, Alipieva K, Simova S, Popova M, Kapchina-Toteva VM, Yordanova ZP. In Vitro Multiplication and NMR Fingerprinting of Rare Veronica caucasica M. Bieb. Molecules. 2021 Sep 28;26(19):5888. doi: 10.3390/molecules26195888. PMID: 34641432; PMCID: PMC8512125. 15: Lee JA, Ngo TH, Shin MR, Choi JW, Choi H, Nam JW, Roh SS. Efficacy of Veronica incana for Treating Osteoarthritis Induced by Monosodium Iodoacetate in Rats. J Med Food. 2023 Jun;26(6):379-389. doi: 10.1089/jmf.2023.K.0001. PMID: 37319312. 16: Su BN, Yang L, Gao K, Jia ZJ. Aquaticol, a bis-sesquiterpene and iridoid glucosides from Veronica anagallis-aquatica. Planta Med. 2000 Apr;66(3):281-3. doi: 10.1055/s-2000-8564. PMID: 10821060. 17: Kwak JH, Kim HJ, Lee KH, Kang SC, Zee OP. Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina. Arch Pharm Res. 2009 Feb;32(2):207-13. doi: 10.1007/s12272-009-1137-x. Epub 2009 Mar 13. PMID: 19280150. 18: Kostadinova EP, Alipieva KI, Kokubun T, Taskova RM, Handjieva NV. Phenylethanoids, iridoids and a spirostanol saponin from Veronica turrilliana. Phytochemistry. 2007 May;68(9):1321-6. doi: 10.1016/j.phytochem.2007.02.014. Epub 2007 Mar 30. PMID: 17399747. 19: Harput US, Varel M, Nagatsu A, Saracoglu I. Acylated iridoid glucosides from Veronica anagallis-aquatica. Phytochemistry. 2004 Jul;65(14):2135-9. doi: 10.1016/j.phytochem.2004.05.012. PMID: 15279985. 20: Lu Q, Tan S, Gu W, Li F, Hua W, Zhang S, Chen F, Tang L. Phytochemical composition, isolation and hepatoprotective activity of active fraction from Veronica ciliata against acetaminophen-induced acute liver injury via p62-Keap1-Nrf2 signaling pathway. J Ethnopharmacol. 2019 Oct 28;243:112089. doi: 10.1016/j.jep.2019.112089. Epub 2019 Jul 13. PMID: 31310828.