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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/ liver homogenates, bile, gall bladder, blood, urine, contents of gastrointestinal tract (GIT) and feces were analysed for the principal hepatotoxin in lantana leaves viz. lantadene A (LA), its congeners and biotransformation products, using high performance liquid chromatographic technique. Lantadenes could not be detected in liver, bile, gall bladder, blood and urine samples. LA and lantadene B (LB), their derivatives reduced lantadene A (RLA), reduced lantadene B (RLB) and two unidentified metabolites could be detected in the contents of lower GIT and faeces. In vitro incubation of lantana leaf powder with guinea pig caecal contents under anaerobic conditions elicited biotransformation of LA and LB to RLA and RLB, respectively. On the other hand, incubation of lantana leaf powder with cattle rumen liquor under anaerobic conditions did not elicit biotransformation of lantadenes. |
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| Toxicity/Toxicokinetics |
Interactions
Lantadenes are pentacyclic triterpenoids isolated from leaves of Lantana camara L. and have antitumor activity. ... The present study was specially designed to initiate the involvement of the molecular targets in chemopreventive activity of these compounds. Skin lesions were induced by twice-weekly topical application of 7,12-dimethylbenz(a)anthracene (DMBA) (100 nmol/100 uL of acetone) for 2 weeks followed by TPA (1.7 nmol/100 uL of acetone) on depilated back of mice for 20 weeks. Lantadene A (LA) and methyl ester of LA (LAM) were administered orally at a dose of 50 mg/kg body weight twice weekly, 1 week before DMBA application and continued for 20 weeks thereafter. A significant decrease in the incidence of number of lesions in mice was obtained in LA/LAM treated groups as compared to DMBA/TPA alone. Significant increase in the protein levels of c-jun, p65, and p53 by ELISA were observed in DMBA/TPA treated mice tumors whereas less expression was observed in LA and LAM treated tumors. Further immunohistochemical localization of transcription factors was studied which also showed less localization of c-jun, p65, and p53 in LA and LAM treated tumors as compared to localization in DMBA/TPA treated tumors. It can be inferred that LA and LAM chemopreventive activity may be linked to the deregulation of above 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 in Lippia turbinata, Combretum sundaicum, and other organisms with data available.
Mechanism of Action THE MAJOR STIMULANTS TO BILE SECRETION IN SHEEP-BILE ACID, TAUROCHOLIC ACID & SECRETIN WERE USED TO ANALYZE THE EFFECTS OF LANTANA ON BILE FORMATION. THE TOXIC PRINCIPLE OF LANTANA CAMARA, LANTADENE A, INHIBITED THE ACTIVE SECRETION OF SHEEP BILE ACIDS INTO CANALICULI THROUGH AN UNKNOWN MECHANISM. THE BILE FLOW RESPONSES TO INFUSIONS OF TAUROCHOLIC ACID WERE DECREASED IN SHEEP AFTER INGESTION OF LANTANA, BUT THE RESPONSE TO SECRETIN WAS ENHANCED. THIS OBSERVATION SUGGESTS THAT LANTADENE A DOES NOT EXERT A TOXIC ACTION ON THE DUCTULES; AN INCREASE IN THE FUNCTION OF DUCTULE CELLS MAY OCCUR. SHEEP POISONED WITH 600 G FRESH LANTANA CAMARA SHOWED INHIBITED GALL BLADDER CONTRACTION AFTER IV ADMIN OF THE GALL BLADDER STIMULANTS CHOLECYSTOKININ, PENTAGASTRIN, PILOCARPINE NITRATE, & HCL 4 DAYS AFTER THE POISONING. GALL BLADDER RESPONSES OCCURRING AFTER THE STIMULANT ADMIN WERE SO FEW THAT THE EFFECT OF LANTANA ON THE RESPONSE DURATION COULD NOT BE MEASURED. LANTADENE A INHIBITED THE CHOLECYSTOKININ-INDUCED CONTRACTIONS IN GALL BLADDER STRIPS. GALL BLADDER PARALYSIS, WHICH MAY OCCUR DURING LANTANA POISONING, MAYBE DUE TO THE ACCUMULATION OF BILE ACIDS. |
| Molecular Formula |
C35H52O5
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|---|---|
| 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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