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Sterols are steroid alcohols such as cholesterol, here listed with oxysterols and bile acids. They share a four-ring steroid nucleus with a hydroxyl group at carbon 3 and help to order the lipids of cell membranes. Oxysterols are oxidized cholesterol derivatives formed by enzymes or by autoxidation. 7α-Hydroxycholesterol, the product of cholesterol 7α-hydroxylase, is the first intermediate of the classic bile acid pathway. Coprostanone is an intermediate in the bacterial reduction of cholesterol to coprostanol in the gut. 24-Methylenecholesterol is a precursor in plant sterol biosynthesis and occurs in pollen. Bile acids, the end products of hepatic cholesterol breakdown, include 3β-Ursodeoxycholic acid and 7-keto-Deoxycholic acid. 16-Dehydropregnenolone acetate is a pregnane steroid used as an intermediate in steroid synthesis.
7α-Hydroxycholesterol is a cholesterol oxide that functions as a biomarker for oxidative stress and lipid peroxidation. Exhibiting cytotoxic and pro-inflammatory properties, it also inhibits sterol synthesis and reduces the activity of HMG-CoA reductase. This compound is valuable in research related to metabolic diseases, including diabetes and atherosclerosis.
Synonyms: 5β-Cholestan-3-one
Coprostanone (5β-cholestan-3-one) is an oxysterol and an active metabolite of cholesterol. This compound has demonstrated the ability to induce apoptosis in primary dog gallbladder epithelial cells. Coprostanone is a valuable research tool for investigating colon cancers and adenomatous polyps, providing insights into the mechanisms of tumorigenesis and potential therapeutic strategies.
Synonyms: Ostreasterol
24-Methylenecholesterol is a sterol that primarily targets acyl-CoA cholesterol acyltransferase (ACAT). It exhibits significant anti-aging and neuroprotective properties, mimicking the effects of nerve growth factor (NGF). Key biological activities include extending yeast lifespan through oxidative stress mitigation and displaying neuroprotective effects in PC12 cells. This compound effectively reduces intracellular reactive oxygen species (ROS) and malondialdehyde (MDA) levels while activating antioxidative stress pathways and promoting synaptic growth, making it a valuable tool for research in aging and neurobiology.
Synonyms: 5α-Cholestane-3β,6α-diol
6α-Hydroxy-5α-cholestane, an oxysterol, is known to stimulate the production of superoxide anions in SK-N-BE cells, particularly at concentrations of 50 μM and 100 μM. This compound serves as a valuable tool in research focused on oxidative stress and cellular signaling pathways. Its biological activity can aid in understanding the roles of oxysterols in neurobiology and related fields.
9-CCN is a lipid compound that selectively targets macrophages, modulating lipid cholesterol metabolism. It demonstrates significant biological activity in the context of cardiovascular and cerebrovascular diseases, making it a valuable tool for researchers investigating lipid-related pathologies and the inflammatory response in these conditions. Its potential applications include elucidating the roles of macrophages in lipid homeostasis and the progression of cardiovascular diseases.
Synonyms: 3-Succinylated cholic acid
3-sucCA is a bacterial bile acid that targets the modulation of intestinal microbiota, specifically promoting the growth of Akkermansia muciniphila. This compound demonstrates anti-metabolic dysfunction-associated steatohepatitis (MASH) effects by enhancing intestinal barrier integrity and reducing chronic low-level inflammation. Research indicates that 3-sucCA accelerates the synthesis of cell wall peptidoglycan and shows in vivo efficacy in mouse models of metabolic-associated fatty liver disease (MAFLD). Its role in studying MASH further underscores its potential in metabolic research applications.
Synonyms: (22S)-Hydroxycholesterol
Cholest-5-ene-3ß,22(S)-diol, also known as (22S)-Hydroxycholesterol, functions as a biologically active oxysterol. It exhibits significant effects on lipid metabolism by inhibiting weight gain and reducing serum triacylglycerol (TAG) levels in rat models. This compound is valuable for research applications related to metabolic disorders and cholesterol regulation, displaying minimal cytotoxic, oxidative, or inflammatory effects on human prokaryotic leukemia cells.
Synonyms: 16-DPA
16-Dehydropregnenolone acetate is a sterol compound that primarily acts as a 17α-hydroxylase and 5α-reductase inhibitor. This reagent demonstrates significant hypolipidemic and anticancer properties, making it a valuable candidate in research concerning lipid metabolism and cancer therapeutics. Additionally, 16-Dehydropregnenolone acetate serves as a drug intermediate for the synthesis of Dexamethasone and other steroidal pharmacophores, facilitating further studies in steroid biochemistry.
7-keto-Deoxycholic acid, a bile acid metabolite, is derived from Clostridium absonum. It can also be converted from Lactobacillus and Bifidobacterium under specific conditions. This compound is utilized in research exploring lipid metabolism, gut microbiota interactions, and the role of bile acids in various biological processes. Its study contributes to understanding metabolic disorders and the therapeutic potential of bile acid derivatives.
Synonyms: Isoursodeoxycholic acid
3β-Ursodeoxycholic acid is a bile acid that exhibits significant oral absorption and tolerance. This compound can be isomerized by intestinal and hepatic enzymes, leading to the production of ursodeoxycholic acid (UDCA). It is primarily utilized in research investigating bile acid metabolism and its therapeutic potential in liver diseases and gallbladder disorders.
Synonyms: β-Phocaecholic acid
Phocaecholic acid, a bile acid derived from duck bile, primarily targets pathways involved in bile acid metabolism. This compound can be excreted into bile and undergoes partial decarboxylation to nor-chenodeoxycholic acid in rat models. Phocaecholic acid holds potential for research applications in investigating bile acid metabolism and associated diseases.
Synonyms: 3α,12α-Dihydroxynorcholanic acid
Nordeoxycholic acid is a 23-carbon bile acid that acts primarily as a norcholic acid metabolite. It is involved in various biochemical pathways and serves as a steroid metabolite in humans. This compound is essential for studies related to bile acid metabolism, gastrointestinal physiology, and cholesterol homeostasis. Its analysis can provide insights into the regulatory mechanisms of lipid absorption and metabolism in both health and disease states.
Glycocholic acid sodium is an orally active bile acid that exhibits anticancer activity. It targets both pump resistance-related and non-pump resistance-related pathways, making it a valuable tool for cancer research. This compound is useful for studies investigating the mechanisms of drug resistance and potential therapeutic strategies in oncology.
Synonyms: 3β-Hydroxy-5β-cholanic acid; 3-Epilithocholic acid; β-Lithocholic acid
Isolithocholic acid, an isomer of Lithocholic acid, primarily targets bile acid metabolism. This compound is produced through microbial metabolism of Lithocholic acid or Lithocholic acid 3α-sulfate. Isolithocholic acid demonstrates significant biological activity and can be used in research applications related to cholestasis, liver function, and lipid metabolism studies.
Chenodeoxycholic acid 3-sulfate disodium is a sulfated bile acid that primarily targets bile acid transport and metabolism. It plays a significant role in hepatic function and is used in research to investigate bile acid signaling pathways and liver health. Its levels can serve as a biomarker for assessing hepatic dysfunction, making it valuable for studies related to liver diseases and metabolic disorders.
Allocholic acid is a bile acid that is typically associated with fetal development and re-emerges during liver regeneration and carcinogenesis. It acts as a potent and specific stimulant of the adult olfactory system, indicating its significance in sensory physiology. Additionally, allocholic acid serves as an important marine metabolite and is found in both rat and human metabolism studies, making it valuable for research in metabolic pathways and olfactory function.
Synonyms: Lithocholylglycine sodium
Glycolithocholic acid sodium, a sodium salt of Glycolithocholic acid, acts as a glycine-conjugated secondary bile acid. It is primarily utilized in the diagnosis of conditions such as ulcerative colitis (UC), non-alcoholic steatohepatitis (NASH), and primary sclerosing cholangitis (PSC). Researchers may leverage its biological activity to explore bile acid metabolism and related gastrointestinal disorders.
Glycodehydrocholic acid is a bile acid glycine conjugate that plays a crucial role in lipid digestion and absorption. This compound is utilized in diagnostic applications for cancer and various diseases by aiding in the assessment of bile acid metabolism. Its biological activity and conjugate properties make it valuable for research on metabolic disorders and gastrointestinal health.
ω-Muricholic Acid is a bile acid that serves as a metabolite of chenodeoxycholic acid, particularly in jaundiced mouse models. It plays a significant role in the study of bile acid metabolism and is relevant for investigating conditions associated with surgical jaundice. Researchers can utilize ω-Muricholic Acid to explore its biological activities and potential therapeutic effects in related pathological contexts.
Synonyms: Cholesterol 3-acetate; Cholesterin acetate; Cholesterol 3β-acetate
Cholesteryl acetate is a cholesterol ester that serves as an important precursor for various biochemical studies. It possesses the capacity to undergo hydrolysis, releasing cholesterol, and is utilized in research exploring lipid metabolism and membrane dynamics. Additionally, cholesteryl acetate can be applied in studies of cellular signaling and the role of cholesterol in health and disease.
Synonyms: TωMCA sodium
Tauro-ω-muricholic acid sodium is a bile acid that serves as an analog of tauro-α-muricholic acid. This compound is being explored as a potential biomarker in plasma for the early detection of neonatal sepsis (EOS) and is used in studies related to cholestasis. Its biological activity underscores the significance of bile acid metabolism in various physiological and pathological conditions.
Apocholic acid is a bile acid that plays a critical role in lipid metabolism and digestion. As an endogenous metabolite, it is involved in the regulation of cholesterol levels and the enterohepatic circulation of bile acids. This compound is utilized in research focusing on metabolic disorders, liver function, and the biochemical pathways of steroid metabolism.
Chenodeoxycholic acid 3-sulfate is a bile acid involved in lipid digestion and absorption. This compound serves as an important biomarker closely linked to the degree of hepatic dysfunction. Its detection and quantification can aid in the assessment of liver health and disease progression in various research applications.
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Cholic acid sodium hydrate is a primary bile acid with a crucial role in the emulsification of dietary fats and the promotion of cholesterol excretion. This compound enhances lipid solubility and facilitates the absorption of lipophilic vitamins and nutrients in the intestine. Cholic acid sodium hydrate is particularly relevant in studies related to metabolic disorders, lipid metabolism, and gastrointestinal function.
Cygnocholic acid, a natural bile acid, plays a crucial role in lipid digestion and absorption. It exhibits biological activities related to cholesterol metabolism and may influence gut microbiota composition. This compound is valuable in research applications focusing on metabolic disorders, gastrointestinal health, and the regulation of bile acids in various biological contexts.
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