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| 1mg |
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Lantadene A is a major pentacyclic triterpenoid isolated from Lantana camara leaves and has been obtained in two polymorphic forms I and II.
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
/Guinea Pig/ High-performance liquid chromatography (HPLC) was used to analyze the main hepatotoxin in Rehmannic camara leaves—Rehmannicene A (LA) and its homologues and biotransformation products. Rehmannicene was not detected in liver, bile, gallbladder, blood, or urine samples. LA, Rehmannicene B (LB), and their derivatives, reduced Rehmannicene A (RLA), reduced Rehmannicene B (RLB), as well as two unidentified metabolites, were detected in lower digestive tract contents and feces. Under anaerobic conditions, in vitro incubation of Rehmannic camara leaf powder with guinea pig cecal contents induced the biotransformation of LA and LB into RLA and RLB, respectively. Conversely, under anaerobic conditions, culturing Rehmannic camara leaf powder with bovine rumen fluid did not induce the biotransformation of Rehmannicene. |
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| Toxicity/Toxicokinetics |
Interactions
Rehmannic compounds are pentacyclic triterpenoids isolated from the leaves of Rehmannic camara L., possessing antitumor activity. …This study aimed to investigate the role of molecular targets in the chemopreventive activity of these compounds. First, 7,12-dimethylbenzanthracene (DMBA) (100 nmol/100 μL acetone) was applied topically to the backs of mice twice weekly after hair removal for 2 weeks to induce skin lesions. Subsequently, TPA (1.7 nmol/100 μL acetone) was applied to the backs of mice for 20 weeks. One week before DMBA application, Rehmannic A (LA) and its methyl ester (LAM) were orally administered twice weekly at a dose of 50 mg/kg body weight, followed by 20 weeks. Compared with the DMBA/TPA group alone, the LA/LAM combined treatment group showed a significant reduction in the number of lesions. ELISA analysis showed significantly elevated levels of c-jun, p65, and p53 proteins in tumors of mice in the DMBA/TPA group, while the expression levels of these proteins were lower in tumors of the LA and LAM combined treatment group. Further immunohistochemical localization studies also indicated that, compared to the DMBA/TPA group, fewer c-jun, p65, and p53 proteins were localized in tumors of the LA and LAM combined treatment group. This suggests that the chemopreventive activity of LA and LAM may be related to the dysregulation of these molecular targets… |
| References |
Grace-Lynn C, Chen Y, Latha LY, Kanwar JR, Jothy SL, Vijayarathna S, Sasidharan S. Evaluation of the hepatoprotective Effects of Lantadene A, a pentacyclic triterpenoid of Lantana plants against acetaminophen-induced liver damage. Molecules. 2012 Nov 23;17(12):13937-47. doi: 10.3390/molecules171213937. Retraction in: Sasidharan S. Molecules. 2013;18(4):3839-40. PubMed PMID: 23178309.
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| Additional Infomation |
Rehmannic acid has been reported to be present in Lippia turbinata, Combretum sundaicum, and other organisms with relevant data.
Mechanism of Action The main stimulants of sheep bile secretion—bile acids, taurocholic acid, and secretin—were used to analyze the effects of Rehmannic on bile formation. Rehmannic camara's toxic component, lantanene A, inhibits the active secretion of sheep bile acids into the bile ducts through an unknown mechanism. After ingestion of Rehmannic, sheep showed a decreased response to taurocholic acid infusion and an enhanced response to secretin. This observation suggests that lantanene A has no toxic effect on the bile ducts; bile duct cell function may be enhanced. Sheep poisoned by ingesting 600 grams of fresh Rehmannic showed inhibited gallbladder contraction after intravenous injection of the gallbladder stimulants cholecystokinin, pentagastrin, pilocarpine nitrate, and pilocarpine hydrochloride four days after poisoning. Gallbladder response was minimal after administration of the stimulant, thus the effect of Rehmannic on the duration of the response could not be measured. Rehmannicene A inhibited cholecystokinin-induced contractions in gallbladder bands. Gallbladder paralysis that may occur during Rehmannic poisoning is likely due to bile acid accumulation. |
| Molecular Formula |
C35H52O5
|
|---|---|
| Molecular Weight |
552.79
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| Exact Mass |
552.381
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| CAS # |
467-81-2
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| Related CAS # |
467-81-2;
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| PubChem CID |
6436598
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
626.3±55.0 °C at 760 mmHg
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| Melting Point |
297 °C
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| Flash Point |
187.9±25.0 °C
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| Vapour Pressure |
0.0±3.9 mmHg at 25°C
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| Index of Refraction |
1.552
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| LogP |
9.56
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
40
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| Complexity |
1190
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| Defined Atom Stereocenter Count |
8
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| SMILES |
C/C=C(/C)\C(=O)O[C@@H]1CC(C[C@@H]2[C@]1(CC[C@@]3(C2=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CCC(=O)C5(C)C)C)C)C)C(=O)O)(C)C
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| InChi Key |
KCLIRHUTOPOHKJ-DSYIDUNCSA-N
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| InChi Code |
InChI=1S/C35H52O5/c1-10-21(2)28(37)40-27-20-30(3,4)19-23-22-11-12-25-32(7)15-14-26(36)31(5,6)24(32)13-16-34(25,9)33(22,8)17-18-35(23,27)29(38)39/h10-11,23-25,27H,12-20H2,1-9H3,(H,38,39)/b21-10+/t23-,24-,25+,27+,32-,33+,34+,35-/m0/s1
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| Chemical Name |
(4R,4aS,6aS,6bR,8aR,12aR,12bR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-4-(((E)-2-methylbut-2-enoyl)oxy)-10-oxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid
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| Synonyms |
Lantadene A Rehmannic acid HSDB 3503
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 | 1.8090 mL | 9.0450 mL | 18.0901 mL | |
| 5 mM | 0.3618 mL | 1.8090 mL | 3.6180 mL | |
| 10 mM | 0.1809 mL | 0.9045 mL | 1.8090 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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