LIPID MAPS

Structure Database (LMSD)

Common Name

Catalpol

Systematic Name

Catalpinoside Catapol De(p-hydroxybenzoyl)catalposide Catalposide, des-p-hydroxybenzoyl- EINECS 219-324-0 UNII-JCX5L7JIC2 JCX5L7JIC2 CHEMBL513223 CHEBI:69797 DTXSID60178850 (1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-Hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl β-D-glucopyranoside

Synonyms

7,8-epoxy Aucubin
Catalpinoside

LM ID

LMPR0102070007

Formula

C₁₅H₂₂O₁₀

Exact Mass

Calculate m/z

362.1213

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View MassBank spectra

Classification

Biological Context

Catalpol is an iridoid glycoside that has been isolated from R. glutinosa and has diverse biological activities, including anti-apoptotic, pro-angiogenic, and radioprotective properties.¹ It protects against mitochondrial pathway-dependent apoptosis in PC12 rat adrenal pheochromocytoma cells and H9c2 rat embryonic ventricular myocardial cells when used at a concentration of 10 µM.^2,3 Catalpol pretreatment reduces apoptosis and improves viability in AHH-1 human lymphocyte cells exposed to ionizing radiation and reduces intestinal damage induced by radiation in mice when used at concentrations and doses ranging from of 25 to 100 µg/ml and 25 to 100 mg/kg, respectively.⁴ In a rat model of stroke, catalpol (5 mg/kg, i.p.) increases the expression of erythropoietin and VEGF and improves angiogenesis in the brain.⁵

This information has been provided by Cayman Chemical

References

1. Chen, C., Chen, Z., Xu, F., et al. Radio-protective effect of catalpol in cultured cells and mice. J. Radiat. Res. 54(1), 76-82 (2013).

2. Chen, W., Li, X., Jia, L.-Q., et al. Neuroprotective activities of catalpol against CaMKII-dependent apoptosis induced by LPS in PC12 cells. Br. J. Pharmacol. 169(5), 1140-1152 (2013).

3. Hu, L.-a., Sun, Y.-k., Zhang, H.-s., et al. Catalpol inhibits apoptosis in hydrogen peroxide-induced cardiac myocytes through a mitochondrial-dependent caspase pathway. Biosci. Rep. 36(3), e00348 (2016).

4. Wang, Y., Liao, D., Qin, M., et al. Simultaneous determination of catalpol, aucubin, and geniposidic acid in different developmental stages of Rehmannia glutinosa leaves by high performance liquid chromatography. J. Anal. Methods Chem. 2016:4956589, (2016).

5. Zhu, H.-F., Wan, D., Luo, Y., et al. Catalpol increases brain angiogenesis and up-regulates VEGF and EPO in the rat after permanent middle cerebral artery occlusion. Int. J. Biol. Sci. 6(5), 443-453 (2010).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Catalpa speciosa (#155717)

Magnoliopsida (#3398)

Structural considerations on the iridoids as anti-inflammatory agents.,
Planta Med, 1994

Pubmed ID: 8073089

String Representations

InChiKey (Click to copy)

LHDWRKICQLTVDL-PZYDOOQISA-N

InChi (Click to copy)

InChI=1S/C15H22O10/c16-3-6-9(19)10(20)11(21)14(23-6)24-13-7-5(1-2-22-13)8(18)12-15(7,4-17)25-12/h1-2,5-14,16-21H,3-4H2/t5-,6-,7-,8+,9-,10+,11-,12+,13+,14+,15-/m1/s1

SMILES (Click to copy)

O([C@@H]1OC=C[C@@]2([H])[C@H](O)[C@]3([H])O[C@]3(CO)[C@]21[H])[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O