(1S)-Calcitriol (1α,25-Dihydroxy-3-epi-vitamin-D3) is a natural metabolite of 1α,25-dihydroxyvitamin D3 (1α,25(OH)2D3). (1S)-Calcitriol exhibits potent vitamin D receptor (VDR)-mediated actions such as inhibition of keratinocyte growth or suppression of parathyroid hormone secretion[1].
3‐epi‐Calcitroic acid is an end product of (1S)-Calcitriol (1α,25-Dihydroxy-3-epi-vitamin-D3; 3‐epi‐1a,25(OH)2D3) metabolism by rat CYP24A1[1].
[1]. Steve Y Rhieu, et al. Metabolic stability of 3-epi-1α,25-dihydroxyvitamin D3 over 1 α 25-dihydroxyvitamin D3: metabolism and molecular docking studies using rat CYP24A1. J Cell Biochem. 2013 Oct;114(10):2293-305.
Bile acids are essential for solubilization and transport of dietary lipids, are the major products of cholesterol catabolism, and are physiological ligands for farnesoid X receptor (FXR), a nuclear receptor that regulates genes involved in lipid metabolism.1They are also inherently cytotoxic, as physiological imbalance contributes to increased oxidative stress.2,3Bile acid-controlled signaling pathways are promising novel targets to treat such metabolic diseases as obesity, type II diabetes, hyperlipidemia, and atherosclerosis.Guggulsterone, derived from resin of the guggul tree, is a competitive antagonist of FXR bothin vitroandin vivo.4Thecisstereoisomer of guggulsterone, (E)-guggulsterone, decreases chenodeoxycholic acid (CDCA)-induced FXR activation with an IC50value of 15 μM.5,6By inhibiting CDCA-induced transactivation of FXR, guggulsterone lowers low-density lipoprotein cholesterol and triglyceride levels in rodents fed a high cholesterol diet.4
1.Makishima, M., Okamoto, A.Y., Repa, J.J., et al.Identification of a nuclear receptor for bile acidsScience2841362-1365(1999) 2.Barbier, O., Torra, I.P., Sirvent, A., et al.FXR induces the UGT2B4 enzyme in hepatocytes: A potential mechanism of negative feedback control of FXR activityGastroenterology1241926-1940(2003) 3.Tan, K.P., Yang, M., and Ito, S.Activation of nuclear factor (erythroid-2 like) factor 2 by toxic bile acids provokes adaptive defense responses to enhance cell survival at the emergence of oxidative stressMol. Pharmacol.72(5)1380-1390(2007) 4.Urizar, N.L., Liverman, A.B., Dodds, D.T., et al.A natural product that lowers cholesterol as an anatagonist ligand for FXRScience296(5573)1703-1706(2002) 5.Cui, J., Huang, L., Zhao, A., et al.Guggulsterone is a farnesoid X receptor antagonist in coactivator association assays but acts to enhance transcription of bile salt export pumpThe Journal of Biological Chemisty278(12)10214-10220(2003) 6.Wu, J., Xia, C., Meier, J., et al.The hypolipidemic natural product guggulsterone acts as an antagonist of the bile acid receptorMolecular Endocrinology16(7)1590-1597(2002)
Prostaglandin D1 (PGD1) is the theoretical D-series metabolite of dihomo-γ-linolenic acid (DGLA), but to date it has not been isolated as a natural product. It is an inhibitor of ADP-induced platelet aggregation in humans with an IC50 value of 320 ng/ml, about 1/10 as potent as PGD2. 13,14-dihydro-15-keto Prostaglandin D1 (13,14-dihydro-15-keto PGD1) is the theoretical metabolite of PGD1 via the 15-hydroxy PG dehydrogenase metabolic pathway. No biological studies for this compound have been reported.
Steryl glucosides are neutral glycolipids commonly found in plant cell membranes and vegetable oils that contain a glucose moiety conjugated to a sterol lipid. They function as glucose donors in the biosynthesis of glucocerebrosides in plant microsomes and are metabolic precursors to acylated/esterified steryl glucosides. Steryl glucosides are the major component of filter- and engine-damaging precipitates formed during biodiesel production from transesterification of vegetable oils. This product contains a mixture of steryl glucosides.
12(S)-HETE is a product of arachidonic acid metabolism through the 12-lipoxygenase pathway. It is primarily found in platelets, leukocytes, and to a lesser extent in smooth muscle cells. It enhances tumor cell adhesion to endothelial cells, fibronectin, and the subendothelial matrix. tetranor-12(S)-HETE is the major β-oxidation product resulting from peroxisomal metabolism of 12(S)-HETE in numerous tissues, and Lewis lung carcinoma cells. No biological function has yet been determined for tetranor-12(S)-HETE. Some data indicate it may play a role in controlling the inflammatory response in injured corneas. In some diseases (e.g., Zellweger's Syndrome) peroxisomal abnormalities result in the inability of cells to metabolize 12(S)-HETE, which may be responsible for symptoms of the disease. The tetranor derivative of 12(S)-HETE is available as a research tool for the elucidation of the metabolic fate of its parent compound.
Galactosylcerebrosides are glycosphingolipids that contain a galactose attached to a ceramide acylated with a hydroxy or non-hydroxy fatty acid. They are metabolic precursors to sulfatides , found primarily in nerve tissues, and are the main glycosphingolipids in the central nervous system. Galactosylcerebrosides are involved in a multitude of cellular processes including cell agglutination, cellular signaling in glycosynapses, cellular development, and activation of T cells. They accumulate in globoid cells in the brain of patients with Krabbe disease, a disorder characterized by a deficiency in galactosylcerebrosidase activity. This product is a mixture of isolated bovine hydroxy galactosylcerebrosides.
Galactosylcerebrosides are glycosphingolipids that contain a galactose attached to a ceramide acylated with a hydroxy or non-hydroxy fatty acid. They are metabolic precursors to sulfatides , found primarily in nerve tissues, and are the main glycosphingolipids in the central nervous system. Galactosylcerebrosides are involved in a multitude of cellular processes including cell agglutination, cellular signaling in glycosynapses, cellular development, and activation of T cells. They accumulate in globoid cells in the brain of patients with Krabbe disease, a disorder characterized by a deficiency in galactosylcerebrosidase activity. This product is a mixture of isolated bovine non-hydroxy galactosylcerebrosides.
20-hydroxy Prostaglandin E2 (20-hydroxy PGE2) is a product of cytochrome P450 metabolism of PGE2 . ω-Oxidation at C-20 followed by β-oxidation and the loss of up to four carbons from the lower side chain is a prominent metabolic pathway for PGE2. 20-hydroxy PGE2 is the putative first intermediate in this chain of chemical transformations.