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Product name: Campesterol
Synonym name: Mieyajunsu A; Campest-5-en-3-ol
Catalogue No.: BP0307
Cas No.: 474-62-4
Formula: C28H48O
Mol Weight: 400.691
Botanical Source:
Physical Description:
Type of Compound: Steroids
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams, up to kilograms
Inquire for bulk scale.
Descriptions:
Dietary campest-5-en-3-one (campestenone), an oxidized derivative of campesterol, can activate PPAR alpha, promote energy consumption and significantly reduce visceral fat weight and the concentration of triacylglycerol in serum and liver of rats.[1]
Campesterol oxidised derivatives and dihydrobrassicasterol have toxicity in U937 and HepG2 cells.[2]
Campesterol oxidation products have different antioxidant effects.[3]
At higher sterol concentrations, campesterol (Camp) and brassicasterol (Bras) are less miscible and less effective than cholesterol (Chol) at ordering the hydrocarbon chains of the sterol-enriched fluid DPPC bilayers, overall, these alkyl side chain modifications generally reduce the ability of Chol to produce its characteristic effects on DPPC bilayer physical properties. [4]
References:
[1] Ikeda I, Konno R, Shimizu T, et al.BBA-BiomembranesI?, 2006, 1760(5):800-7.
[2] O Callaghan Y, Kenny O, O’Connell N M, et al. Biochimie, 2013, 95(3):496-503.
[3] Kmiecik D, Korczak J, Rudzińska M, et al. Food Chem, 2011, 128(4):937-42.
[4] Benesch M G K, Mcelhaney R N. BBA-BiomembranesI, 2014, 1838(7):1941-9.
[5] Jia M Q, Tang H, Cui-Hua L I, et al. Food Sci Technol 2013, 12(4):651.
HPLC of Campesterol
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
20.2300
8.5000
8.5000
Low
No
No
No
No
No
No
Campesterol (CAS number: 474-62-4), as an important plant sterol, has attracted significant attention in recent years for its significant cholesterol-lowering and anticancer activities. Plant sterols are widely present in plant cell membranes and are an important branch of steroid compounds. Structurally, they are similar to cholesterol, but their side chains differ and give them unique biological functions. Cae olesterol, as a representative of 3β-hydroxy-Delta(5)-steroid and C28-steroid, is widely found in vegetable oils such as rapeseed, corn, and soybeans, and has multiple pharmacological effects including lipid metabolism regulation, anti-inflammatory, and antitumor effects.
This review aims to systematically summarize the chemical structure and physicochemical properties of caplacesterol, plant origin, and extraction methods, with a focus on its pharmacological activity and molecular mechanisms in diseases such as atherosclerosis, inflammatory bowel disease, breast cancer, and prostate cancer. It will delve into its druggability and pharmacokinetic characteristics, and finally look ahead to its clinical application potential and future research directions, providing theoretical basis and research references for natural product pharmacology and new drug development.
The chemical name of rapesesterol is 3β-hydroxy-delta(5)-steroid, with a molecular formula C28H48O and a molecular weight of about 400.67. Its structural core is a tetracyclic steroid backbone, featuring a 3β hydroxyl group and an unsaturated Δ5 double bond, with the side chain being a hydrogenated derivative of rapeseed alkane. Its structure is highly similar to cholesterol, but its side chain contains an additional methyl group, giving it unique biological activity.
In terms of physicochemical properties, the LogP value of caisesterol reaches as high as 8.5, indicating high hydrophobicity, poorly soluble in water, and easily soluble in organic solvents. The polar surface area (TPSA) is 20.23 Ų, and the number of hydrogen bond acceptors is 1, indicating low molecular polarity. Its molecular structure is stable, with no significant hepatotoxicity, cardiotoxicity, or hERG channel inhibition. The Ames test result was negative, indicating a low genotoxicity risk. The blood-brain barrier has low penetration, limiting its direct impact on the central nervous system.
Radish olesterol is mainly found in various vegetable oils, especially abundant in rapeseed oil, corn oil, soybean oil, and palm oil. As an important component of plant cell membranes, the content of caisesterol in plants is greatly influenced by variety, environment, and processing techniques.
In terms of extraction processes, traditional methods include solvent extraction, cold pressing, and supercritical CO₂ extraction. Solvent extraction usually uses organic solvents such as ethanol and hexane, and high-purity caisesterol is obtained through steps such as fractionation, concentration, and crystallization. Supercritical CO₂ extraction technology is gradually becoming the mainstream industrial extraction method due to its green and environmentally friendly nature, strong selectivity, and excellent thermal stability. In addition, membrane separation technology and chromatographic purification techniques are also applied to the purification of casusterol, ensuring its purity and biological activity.
As an important member of plant sterols, caseed sterol can competitively inhibit intestinal cholesterol absorption and lower plasma cholesterol levels. Its mechanism involves regulating cholesterol metabolism-related targets, such as cholesterol ester transfer protein (CETP), 3-hydroxy-3-methylglutaryl-CoA reductase (HMGCR), low-density lipoprotein receptor (LDLR), apolipoprotein B (APOB), proproprotein-converting enzyme lysozyme subtilis 9 (PCSK9), and cholate synthase (CYP7A1). By promoting cholesterol transport and metabolism, catechin alcohol effectively lowers serum low-density lipoprotein cholesterol (LDL-C) and slows the progression of atherosclerosis.
Inflammatory bowel disease (IBD) is a class of chronic inflammatory diseases, and genisterol exerts anti-inflammatory effects by regulating various inflammation-related signaling pathways. Its targets include AMP-activated protein kinase (AMPK), NOTCH1, thymosin-like protease (CES1, CES2), TLR4, interleukin-6 (IL-6), protein tyrosine phosphatase 1 (PTPN1), signal transduction and transcription activator factor 3 (STAT3), and estrogen receptor β (ESR2). Caisterol reduces pro-inflammatory cytokine expression by inhibiting TLR4-mediated inflammatory responses, alleviating intestinal mucosal damage, and improving IBD symptoms.
Cai olesterol exhibits significant antiproliferative and pro-apoptosis effects in various tumor models including breast and prostate cancer. Its targets include the cell apoptosis regulator protein BCL2, the STAT3 signaling pathway, estrogen receptor β (ESR2), drug efflux pumps ABCB1 and ABCG2, microtubule-associated protein Tau (MAPT), topoisomerase I (TOP1), deacetylase SIRT1, and nuclear factor κB subunit RELA. By regulating these molecules, castanol can inhibit tumor cell proliferation, induce cell cycle arrest, and promote apoptosis. Additionally, rapesterol affects prostate cancer-related targets such as androgen receptor (AR), PI3K/AKT signaling pathway (PIK3CA), epidermal growth factor receptor (EGFR), and galactogenin 3 (LGALS3), enhancing anti-tumor effects.
Caisterol has also been reported to have potential effects in regulating energy metabolism, antioxidant properties, and immune regulation. By activating the AMPK signaling pathway, it promotes lipid metabolism and energy balance, potentially offering adjunctive therapeutic value for diseases such as metabolic syndrome.
The multi-target mechanism of rapesterol is the basis of its pharmacological activity. Its main targets and mechanisms of action are as follows:
AMPK (PRKAA1): As a cellular energy sensor, AMPK activation promotes lipid metabolism and anti-inflammatory responses. Cai olesterol activates AMPK, regulates lipid metabolism, and inhibits inflammation, exerting lipid-lowering and anti-inflammatory effects.
Cholesterol metabolism-related targets: including HMGCR, LDLR, PCSK9, CETP, etc. Raspolesterol lowers plasma cholesterol levels and prevents atherosclerosis by regulating these targets.
Inflammatory signaling pathways: Inflammation-related molecules such as TLR4, IL-6, STAT3, and PTPN1 are regulated by rapesesterol, reducing inflammatory responses and improving inflammatory bowel disease.
Tumor-related targets: BCL2, STAT3, ESR2, ABCB1, ABCG2, MAPT, TOP1, SIRT1, RELA, etc. Caisterol inhibits tumor growth and drug resistance by regulating apoptosis, drug efflux, and signal transduction.
Hormone receptors and signaling pathways: such as AR, CYP19A1, MAPK1, EGFR, PIK3CA, etc. Caisterol affects signaling pathways in hormone-dependent tumors and regulates the tumor microenvironment.
Immunomodulatory targets: Immunomodulatory molecules such as IDO1 participate in the immunomodulatory effects of brassicinol, enhancing the body's anti-tumor and anti-inflammatory abilities.
In summary, rapesesterol demonstrates its complex and diverse pharmacological activities through multi-target and multi-pathway synergistic effects.
Druggability evaluation of caisesterol shows good safety and drug compatibility. A high LogP value (8.5) suggests strong lipophilus, easy penetration of cell membranes, but poor water solubility, which may affect oral bioavailability. Low polarity surface area and fewer hydrogen bond receptors facilitate penetration of biofilms, but may also limit intracytosis distribution.
In terms of safety, rapesesterol has no hepatotoxicity, cardiotoxicity, or hERG channel inhibitory effects. The negative Ames test indicates a low genotoxicity risk and is suitable for long-term use. The blood-brain barrier has low penetration, reducing the risk of central nervous system side effects.
Pharmacokinetic studies show that catechinol is slowly absorbed orally and has a long plasma half-life, mainly metabolized by the liver. The metabolites show certain bioactivity in mouse models. Its lipophilic nature makes it easy for it to accumulate in fat tissue, which may affect drug distribution and clearance. Further research is needed in the future on its metabolic pathways and drug interactions.
As a natural plant sterol, rape olesterol has broad clinical application prospects due to its remarkable cholesterol-lowering and anticancer activities. In the field of cardiovascular diseases, caulisterol provides an adjunctive treatment for patients with hyperlipidemia and coronary heart disease by lowering serum cholesterol and inhibiting atherosclerosis. In the treatment of inflammatory bowel disease, its anti-inflammatory effect is expected to improve patient symptoms and reduce drug side effects.
In terms of antitumor effects, genitol has potential adjunctive therapeutic value for breast and prostate cancers, especially showing unique advantages in overcoming tumor resistance and regulating the tumor microenvironment. In the future, it can be combined with existing chemotherapy drugs to enhance therapeutic outcomes.
However, the low water solubility and bioavailability of cab olesterol limit its clinical promotion. The development of novel delivery systems such as nanocarriers, liposomes, and solid dispersions will help improve their pharmacokinetic performance. In addition, in-depth analysis of its molecular mechanisms of action and clinical safety evaluation is key to achieving its clinical translation.
Future research should focus on:
As a plant sterol with multiple biological activities, catechols demonstrate significant potential for lowering cholesterol, anti-inflammation, and anti-tumor. Its multi-target, multi-mechanism pharmacological effects provide rich material for pharmacological research of natural products and open new avenues for new drug development. Despite current challenges such as poor water solubility and low bioavailability, with advances in extraction technology and drug carriers, caisesterol is expected to become an important natural drug resource for treating cardiovascular diseases, inflammatory diseases, and tumors. Future systematic pharmacological mechanism research and clinical validation will further promote its clinical application and industrialization process, supporting the innovative development of natural product drugs.
Shenshuai
Wenjing
Hedandan
