Catalposide
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MedKoo CAT#: 412435

CAS#: 6736-85-2

Description: Catalposide is a compound isolated from irinoid-producing plant Catalpa ovata. Catalposide has been shown to possess anti-microbial, anti-tumoral, and anti-inflammatory properties. was found to inhibit the productions of tumor necrosis factor-alpha (TNF- alpha), interleukin-1beta, and interleukin-6 (IL-6), and the activation of nuclear factor kB (NF-kB) in RAW 264.7 macrophages activated with lipopolysaccharide (LPS).


Chemical Structure

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Catalposide
CAS# 6736-85-2

Theoretical Analysis

MedKoo Cat#: 412435
Name: Catalposide
CAS#: 6736-85-2
Chemical Formula: C22H26O12
Exact Mass: 482.1424
Molecular Weight: 482.44
Elemental Analysis: C, 54.77; H, 5.43; O, 39.80

Price and Availability

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1.0mg USD 413.0 2 Weeks
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Synonym: Catalposide; EINECS 229-789-1

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 4-hydroxybenzoate

InChi Key: UXSACQOOWZMGSE-RWORTQBESA-N

InChi Code: InChI=1S/C22H26O12/c23-7-12-14(26)15(27)16(28)21(31-12)33-20-13-11(5-6-30-20)17(18-22(13,8-24)34-18)32-19(29)9-1-3-10(25)4-2-9/h1-6,11-18,20-21,23-28H,7-8H2/t11-,12-,13-,14-,15+,16-,17+,18+,20+,21+,22-/m1/s1

SMILES Code: OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)O[C@@H]2OC=C[C@H]3[C@@H]([C@@H]4O[C@@]4([C@@H]23)CO)OC(c5ccc(O)cc5)=O

Appearance: 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: >3 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

Product Data:

Biological target: Catalposide, an iridoid glycoside that could be isolated from Catalpa ovate G. Don (Bignoniaceae), inhibits TNF-α, IL-1β, and IL-6 productions and NF-κB (p65) activation in lipopolysaccharide-activated RAW 264.7 macrophages
In vitro activity: Catalposide, the major iridoid glycoside isolated from the stem bark of Catalpa ovata G. Don (Bignoniaceae) has been shown to possess anti-microbial, anti-tumoral, and anti-inflammatory properties. Heme oxygenase-1 (HO-1) is a stress response protein and is known to play a protective role against the oxidative injury. In this study, whether catalposide could protect Neuro 2A cells, a kind of neuronal cell lines, from oxidative damage through the induction of HO-1 protein expression and HO activity was examined. The treatment of the cells with catalposide resulted in dose- and time-dependent up-regulations of both HO-1 protein expression and HO activity. Catalposide protected the cells from hydrogen peroxide-induced cell death. The protective effect of catalposide on hydrogen peroxide-induced cell death was abrogated by zinc protoporphyrin IX (ZnPP IX), a HO inhibitor. Additional experiments revealed the involvement of CO in the cytoprotective effect of catalposide-induced HO-1. These results indicate that catalposide is a potent inducer of HO-1 and HO-1 induction is responsible for the catalposide-mediated cytoprotection against oxidative damage. Reference: Toxicol Lett. 2003 Nov 1;145(1):46-54. https://linkinghub.elsevier.com/retrieve/pii/S0378427403002686
In vivo activity: To establish the in vivo relevance, whether catalposide (CATP) could affect intestinal inflammation in vivo was evaluated using the mouse model of trinitrobenzene sulfonic acid (TNBS)-induced inflammatory colitis. Intrarectal administration of CATP dramatically reduced the weight loss, colonic damage, and mucosal ulceration that characterize TNBS colitis. Moreover, CATP suppressed the expression of TNF-alpha, interleukin-1beta, and intercellular adhesion molecule-1 along with the inhibition of NF-kappa B p65 translocation into nucleus in TNBS colitis. Collectively, current results demonstrate that CATP may be an effective agent for the treatment of diseases characterized by mucosal inflammation. Reference: Inflamm Bowel Dis. 2004 Sep;10(5):564-72. https://academic.oup.com/ibdjournal/article/10/5/564/4718213

Preparing Stock Solutions

The following data is based on the product molecular weight 482.44 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
In vitro protocol: 1. Moon MK, Choi BM, Oh GS, Pae HO, Kim JD, Oh H, Oh CS, Kim DH, Rho YD, Shin MK, Lee HS, Chung HT. Catalposide protects Neuro 2A cells from hydrogen peroxide-induced cytotoxicity via the expression of heme oxygenase-1. Toxicol Lett. 2003 Nov 1;145(1):46-54. doi: 10.1016/s0378-4274(03)00268-6. PMID: 12962973. 2. Kim SW, Choi SC, Choi EY, Kim KS, Oh JM, Lee HJ, Oh HM, Kim S, Oh BS, Kimm KC, Lee MH, Seo GS, Kim TH, Oh HC, Woo WH, Kim YS, Pae HO, Park DS, Chung HT, Jun CD. Catalposide, a compound isolated from catalpa ovata, attenuates induction of intestinal epithelial proinflammatory gene expression and reduces the severity of trinitrobenzene sulfonic Acid-induced colitis in mice. Inflamm Bowel Dis. 2004 Sep;10(5):564-72. doi: 10.1097/00054725-200409000-00010. PMID: 15472516.
In vivo protocol: 1. Kim SW, Choi SC, Choi EY, Kim KS, Oh JM, Lee HJ, Oh HM, Kim S, Oh BS, Kimm KC, Lee MH, Seo GS, Kim TH, Oh HC, Woo WH, Kim YS, Pae HO, Park DS, Chung HT, Jun CD. Catalposide, a compound isolated from catalpa ovata, attenuates induction of intestinal epithelial proinflammatory gene expression and reduces the severity of trinitrobenzene sulfonic Acid-induced colitis in mice. Inflamm Bowel Dis. 2004 Sep;10(5):564-72. doi: 10.1097/00054725-200409000-00010. PMID: 15472516.

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1: Hwang DK, Kim JH, Shin Y, Choi WG, Kim S, Cho YY, Lee JY, Kang HC, Lee HS. Identification of Catalposide Metabolites in Human Liver and Intestinal Preparations and Characterization of the Relevant Sulfotransferase, UDP- glucuronosyltransferase, and Carboxylesterase Enzymes. Pharmaceutics. 2019 Jul 22;11(7):355. doi: 10.3390/pharmaceutics11070355. PMID: 31336576; PMCID: PMC6681058.

2: Ryu HW, Lee SU, Lee S, Song HH, Son TH, Kim YU, Yuk HJ, Ro H, Lee CK, Hong ST, Oh SR. 3-Methoxy-catalposide inhibits inflammatory effects in lipopolysaccharide-stimulated RAW264.7 macrophages. Cytokine. 2017 Mar;91:57-64. doi: 10.1016/j.cyto.2016.12.006. Epub 2016 Dec 21. PMID: 28011397.

3: Moon MK, Choi BM, Oh GS, Pae HO, Kim JD, Oh H, Oh CS, Kim DH, Rho YD, Shin MK, Lee HS, Chung HT. Catalposide protects Neuro 2A cells from hydrogen peroxide-induced cytotoxicity via the expression of heme oxygenase-1. Toxicol Lett. 2003 Nov 1;145(1):46-54. doi: 10.1016/s0378-4274(03)00268-6. PMID: 12962973.

4: Lee JH, Jun HJ, Hoang MH, Jia Y, Han XH, Lee DH, Lee HJ, Hwang BY, Lee SJ. Catalposide is a natural agonistic ligand of peroxisome proliferator-activated receptor-α. Biochem Biophys Res Commun. 2012 Jun 15;422(4):568-72. doi: 10.1016/j.bbrc.2012.05.025. Epub 2012 May 11. PMID: 22583896.

5: Jeong HU, Kwon M, Lee Y, Yoo JS, Shin DH, Song IS, Lee HS. Organic anion transporter 3- and organic anion transporting polypeptides 1B1- and 1B3-mediated transport of catalposide. Drug Des Devel Ther. 2015 Jan 22;9:643-53. doi: 10.2147/DDDT.S75400. PMID: 25653502; PMCID: PMC4310350.

6: Diopan V, Babula P, Shestivska V, Adam V, Zemlicka M, Dvorska M, Hubalek J, Trnkova L, Havel L, Kizek R. Electrochemical and spectrometric study of antioxidant activity of pomiferin, isopomiferin, osajin and catalposide. J Pharm Biomed Anal. 2008 Sep 10;48(1):127-33. doi: 10.1016/j.jpba.2008.05.025. Epub 2008 May 28. PMID: 18597965.

7: Oh H, Pae HO, Oh GS, Lee SY, Chai KY, Song CE, Kwon TO, Chung HT, Lee HS. Inhibition of inducible nitric oxide synthesis by catalposide from Catalpa ovata. Planta Med. 2002 Aug;68(8):685-9. doi: 10.1055/s-2002-33810. PMID: 12221588.

8: Kim SW, Choi SC, Choi EY, Kim KS, Oh JM, Lee HJ, Oh HM, Kim S, Oh BS, Kimm KC, Lee MH, Seo GS, Kim TH, Oh HC, Woo WH, Kim YS, Pae HO, Park DS, Chung HT, Jun CD. Catalposide, a compound isolated from catalpa ovata, attenuates induction of intestinal epithelial proinflammatory gene expression and reduces the severity of trinitrobenzene sulfonic Acid-induced colitis in mice. Inflamm Bowel Dis. 2004 Sep;10(5):564-72. doi: 10.1097/00054725-200409000-00010. PMID: 15472516.

9: 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.

10: An SJ, Pae HO, Oh GS, Choi BM, Jeong S, Jang SI, Oh H, Kwon TO, Song CE, Chung HT. Inhibition of TNF-alpha, IL-1beta, and IL-6 productions and NF-kappa B activation in lipopolysaccharide-activated RAW 264.7 macrophages by catalposide, an iridoid glycoside isolated from Catalpa ovata G. Don (Bignoniaceae). Int Immunopharmacol. 2002 Jul;2(8):1173-81. doi: 10.1016/s1567-5769(02)00085-1. PMID: 12349954.