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| 500mg | ||
| 1g | ||
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Lophenol is a steroidal compound with potent inhibitory activity against human cancer cell lines such as liver cancer, nasopharyngeal and colon cancer cells.
Lophenol (also known as 4α-methyl-5α-cholest-7-en-3β-ol) is a naturally occurring tetracyclic triterpenoid and phytosterol belonging to the cholestane class of steroids . It has the molecular formula C₂₈H₄₈O and a molecular weight of 400.7 g/mol . Lophenol is a key intermediate in the biosynthesis of sterols in both plants and mammals, specifically in the Kandutsch-Russell pathway for cholesterol synthesis . It has been isolated from various natural sources including the resin of Commiphora kua, Aloe vera, and tobacco leaves . Lophenol exhibits potent inhibitory activity against human cancer cell lines such as liver cancer, nasopharyngeal cancer, and colon cancer cells, and possesses hepatoprotective effects against drug-induced liver damage as demonstrated in murine models .| Targets |
Lophenol targets multiple biological pathways. It acts as a sterol intermediate in the Kandutsch-Russell cholesterol biosynthesis pathway . The compound has been shown to modulate cancer cell differentiation through cholesterol metabolism pathways, specifically via the enzyme FAXDC2; suppression of FAXDC2 leads to lophenol accumulation, which maintains cancer cells in an undifferentiated stem cell-like state . In hepatoprotection, lophenol exhibits antioxidant activity against acetaminophen-induced oxidative stress .
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| ln Vitro |
Lophenol exhibits anticancer activity. It has been shown to have potent inhibitory activity against human cancer cell lines, including liver cancer, nasopharyngeal cancer, and colon cancer cells . The compound also affects cell differentiation pathways: when the enzyme FAXDC2 is suppressed, lophenol levels increase, which prevents cell differentiation and maintains cancer cells in a stem cell-like state . These undifferentiated cancer stem cells can proliferate rapidly, resist anti-cancer therapies, and promote faster tumor progression . Lophenol has also been reported to stimulate human dermal fibroblasts, promoting collagen and hyaluronic acid production .
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| ln Vivo |
Lophenol has been evaluated for hepatoprotective effects in a murine model of acetaminophen (APAP)-induced hepatotoxicity . Mice treated with Lophenol at doses of 25 μg/kg body weight and 50 μg/kg body weight (oral administration, daily for 7 days) exhibited significant recovery of liver function tests, including reduced levels of ALT (alanine transaminase), AST (aspartate transaminase), ALP (alkaline phosphatase), LDH (lactate dehydrogenase), and direct bilirubin compared to the APAP-only control group . Lophenol treatment also restored the concentration of antioxidant enzymes (catalase (CAT), superoxide dismutase (SOD), and reduced glutathione (GSH)), which were significantly depleted by APAP administration . Histological analysis confirmed significant improvement of liver tissue architecture in lophenol-treated animals . The hepatoprotective effect was comparable to the reference drug silymarin (100 mg/kg) .
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| Enzyme Assay |
Liver function parameters were measured as biochemical markers of hepatoprotection. Lophenol treatment significantly decreased the levels of lactate dehydrogenase (LDH), alkaline phosphatase (ALP), alanine transaminase (ALT), aspartate transaminase (AST), and direct bilirubin in serum . The compound also restored the activity of antioxidant enzymes: catalase (CAT), superoxide dismutase (SOD), and reduced glutathione (GSH) in liver tissue homogenates . These enzymes were measured using standard biochemical assay kits. The assays were performed on samples collected 20 hours after APAP administration (400 mg/kg i.p.) .
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| Cell Assay |
Specific step-by-step protocols for in vitro cell-based assays using Lophenol are not described in the available literature. However, the compound has been reported to have potent inhibitory activity against human cancer cell lines such as liver cancer, nasopharyngeal, and colon cancer cells . Additionally, research indicates that lophenol, when accumulated due to FAXDC2 suppression, prevents cell differentiation and maintains cancer cells in a stem cell-like state, suggesting potential effects on cancer stem cell populations . Lophenol has also been shown to stimulate human dermal fibroblasts, increasing the production of collagen and hyaluronic acid in coculture experiments with Aloe sterols .
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| Animal Protocol |
The following in vivo protocol is described from the hepatoprotection study: Female and male mice (n=5 per group) were divided into seven groups: Vehicle control (0.1% DMSO for 7 days), APAP control (single dose on day 7), Silymarin (100 mg/kg for 7 days), Lop 25 (25 μg/kg body weight lophenol daily for 7 days), Lop 50 (50 μg/kg body weight lophenol daily for 7 days), Lat 25, and Lat 50 groups . On day 7, all animals except the vehicle group were fasted for 18 hours and received APAP (400 mg/kg body weight, intraperitoneal injection). After 20 hours of APAP administration, animals were anesthetized with light chloroform and sacrificed by cervical decapitation. Blood serum and liver tissue samples were collected for biochemical and histopathological analysis . Liver function tests (ALT, AST, ALP, LDH, direct bilirubin) and antioxidant enzyme assays (CAT, SOD, GSH) were performed on collected samples. Liver tissues were also examined histologically for signs of damage and recovery .
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| ADME/Pharmacokinetics |
One study notes that the compound should be further evaluated for pharmacokinetics/pharmacodynamics profile, indicating that such data are not yet available . Basic physicochemical properties include: molecular weight 400.7 g/mol, logP of 7.6-8.7 (highly lipophilic), hydrogen bond donor count 1, hydrogen bond acceptor count 1, rotatable bond count 5, and melting point 149-151°C . Lophenol is soluble in DMSO .
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| Toxicity/Toxicokinetics |
Acute toxicity studies for Lophenol have not been reported in the available literature; the compound is recommended for further evaluation in acute toxicity studies . However, phytosterols in general are reported to be well-tolerated phytochemicals with no reported serious adverse effects . Lophenol has been isolated from edible sources such as Aloe vera and is present in tobacco leaves, suggesting some level of natural occurrence in consumable products . The compound is explicitly labeled “for research use only, not for human or veterinary use” by commercial suppliers .
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| References |
[1]. https://pubchem.ncbi.nlm.nih.gov/compound/160482
【2】。 [Steroidal alkaloids 98. Chemical constitution of the seeds of Holarrhena floribunda (G. Don) Dur. and Schiz: cycloartenol, nor-31 lanosterol, dehydro-24 lophenol, desmosterol and steroidal alkaloids: conessine, isoconessimine, conamine and conarrhimine]. Ann Pharm Fr. 1970 Nov;28(11):649-60. |
| Additional Infomation |
4α-Methyl-5α-cholest-7-en-3β-ol is a 3β-hydroxysteroid compound derived from the hydrogenation of 5α-cholest-7-en. It has been reported to be found in potatoes (Solanum tuberosum), oats (Avena sativa), and several other organisms with relevant data.
Lophenol (4α-methyl-5α-cholest-7-en-3β-ol) is a tetracyclic triterpenoid and a key intermediate in the Kandutsch-Russell pathway, one of the two major pathways for cholesterol biosynthesis in mammals . This pathway is characterized by the early reduction of the C24-C25 double bond of lanosterol . Lophenol has been isolated from various natural sources including Commiphora kua resin, Aloe vera gel powder, and tobacco leaves (FC, 8) . In cancer research, lophenol has been identified as a compound that, when accumulated due to suppression of the enzyme FAXDC2, prevents cell differentiation and maintains cancer cells in a stem cell-like state. These undifferentiated cancer stem cells can proliferate rapidly, resist anti-cancer therapies, and promote faster tumor progression, suggesting that targeting FAXDC2 to modulate cholesterol synthesis pathways may represent a novel avenue for cancer therapy . In dermatology, Aloe sterols including lophenol have been shown to stimulate human dermal fibroblasts, increasing collagen and hyaluronic acid production; a clinical study using Aloe vera gel powder containing Aloe sterols demonstrated a significant reduction in facial wrinkles in women aged 40 and over . The compound has also been shown to possess hepatoprotective effects in an APAP-induced hepatotoxicity mouse model, with comparable efficacy to silymarin, suggesting its potential for further development as a hepatoprotective agent . The IUPAC name is (3S,4S,5S,9R,10S,13R,14R,17R)-4,10,13-trimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol . The compound has a CAS registry number of 481-25-4 and a UNII of X4BL075LYS . For research applications, the compound should be stored dry, protected from light, at 0-4°C for short-term or -20°C for long-term storage . |
| Molecular Formula |
C28H48O
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| Molecular Weight |
400.68012
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| Exact Mass |
400.371
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| Elemental Analysis |
C, 83.93; H, 12.08; O, 3.99
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| CAS # |
481-25-4
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| PubChem CID |
160482
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| Appearance |
Typically exists as solid at room temperature
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| Vapour Pressure |
1.51E-11mmHg at 25°C
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| LogP |
7.634
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
29
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| Complexity |
620
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| Defined Atom Stereocenter Count |
9
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| SMILES |
CC1C(CCC2(C1CC=C3C2CCC4(C3CCC4C(C)CCCC(C)C)C)C)O
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| InChi Key |
LMYZQUNLYGJIHI-SPONXPENSA-N
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| InChi Code |
InChI=1S/C28H48O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h10,18-20,22-26,29H,7-9,11-17H2,1-6H3/t19-,20+,22-,23+,24+,25+,26+,27-,28+/m1/s1
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| Chemical Name |
(3S,4S,5S,9R,10S,13R,14R,17R)-4,10,13-trimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
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| Synonyms |
Lophenol; 481-25-4; 4alpha-Methyl-5alpha-cholest-7-en-3beta-ol; X4BL075LYS; CHEBI:18378; Methostenol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4958 mL | 12.4788 mL | 24.9576 mL | |
| 5 mM | 0.4992 mL | 2.4958 mL | 4.9915 mL | |
| 10 mM | 0.2496 mL | 1.2479 mL | 2.4958 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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