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rehmannic acid
lantadene A

Supplier Sponsors

CAS Number: 467-81-2Picture of molecule3D/inchi
FDA UNII: 9SK62WCU1W
Nikkaji Web:J12.652G
XlogP3-AA:7.80 (est)
Molecular Weight:552.79544000
Formula:C35 H52 O5
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 7.677e-005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
rehmannic acid 96%
BOC Sciences
For experimental / research use only.
Rehmannic acid >95%
Odor: characteristic
Use: Rehmannic acid is a natural triterpenoid found in the herbs of Lantana camara. Rehmannic acid has inhibit succinoxidase activity.
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for rehmannic acid usage levels up to:
 not for fragrance use.
 
Recommendation for rehmannic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6436598
National Institute of Allergy and Infectious Diseases:Data
(4R,4aS,6aR,6aS,6bR,8aR,12aR,14bS)heptamethyl-4-[(Z)-2-methylbut-2-enoyl]oxy-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid
Chemidplus:0000467812
 
References:
 (4R,4aS,6aR,6aS,6bR,8aR,12aR,14bS)heptamethyl-4-[(Z)-2-methylbut-2-enoyl]oxy-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):6436598
Pubchem (sid):135048505
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 lantana camara
Search Trop Picture
 
Synonyms:
22-beta-angeloyl oxyoleanolic acid
22-beta-angeloyloxyoleanolic acid
(4R,4aS,6aR,6aS,6bR,8aR,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-4-[(Z)-2-methylbut-2-enoyl]oxy-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid
 lantadene A
22-((2-methyl-1-oxo-2-butenyl)oxy)-3-oxo-olean-12-en-28-oic acid, (22beta)
22-((2-methyl-1-oxo-2-butenyl)oxy)-3-oxo-olean-12-en-28-oic acid, 22-beta(Z)-
 olean-12-en-28-oic acid, 22-((2-methyl-1-oxo-2-butenyl)oxy)-3-oxo-, (22beta(Z))-
 olean-12-en-28-oic acid, 22-beta-hydroxy-3-oxo-, 2-methylcrotonate, (Z)-
 olean-12-en-28-oic acid, 22beta-hydroxy-3-oxo-, 2-methylcrotonate, (Z)-
 

Articles:

PubMed:Evaluation of the hepatoprotective Effects of Lantadene A, a pentacyclic triterpenoid of Lantana plants against acetaminophen-induced liver damage.
PubMed:In vitro antioxidant activity potential of lantadene A, a pentacyclic triterpenoid of Lantana plants.
PubMed:Remarks on Sasidharan et al. "Evaluation of the hepatoprotective effects of lantadene A, a pentacyclic triterpenoid of Lantana plants against acetaminophen-induced liver damage". Molecules 2012, 17, 13937-13947.
PubMed:Retraction: Sasidharan et al. Evaluation of the hepatoprotective effects of lantadene A, a pentacyclic triterpenoid of Lantana plants against acetaminophen-induced liver damage. Molecules 2012, 17, 13937-13947.
PubMed:Design, synthesis and evaluation of lantadene A congener with hydroxyl functionality in ring A as an antitumour agent.
PubMed:Comparative effects of lantadene A and its reduced metabolite on mitochondrial bioenergetics.
PubMed:Synthesis of lantadene analogs with marked in vitro inhibition of lung adenocarcinoma and TNF-α induced nuclear factor-kappa B (NF-κB) activation.
PubMed:Spectrophotometric determination of lantadene A, 22 beta-angeloyloxy-3-oxoolean-12-en-28-oic acid.
PubMed:Hepatoprotective effect of Ginkgo biloba leaf extract on lantadenes-induced hepatotoxicity in guinea pigs.
PubMed:Biotransformation of lantadene A (22 beta-angeloyloxy-3-oxoolean-12-en-28-oic acid), the pentacyclic triterpenoid, by Alcaligenes faecalis.
PubMed:Synthesis, cytotoxicity, and antitumor activity of lantadene-A congeners.
PubMed:Detoxification of lantana hepatotoxin, lantadene A, using Alcaligenes faecalis.
PubMed:Disposition of lantadene A, the pentacyclic triterpenoid hepatotoxin, orally administered to guinea pigs.
PubMed:Biodegradation of lantadene A, the pentacyclic triterpenoid hepatotoxin by Pseudomonas pickettii.
PubMed:Molecular structure, polymorphism, and toxicity of lantadene A, the pentacyclic triterpenoid from the hepatotoxic plant Lantana camara.
PubMed:Synthesis, selective cancer cytotoxicity and mechanistic studies of novel analogs of lantadenes.
PubMed:Synthesis and in vitro anticancer studies of novel C-2 arylidene congeners of lantadenes.
PubMed:Effective melanoma inhibition by synthetic pentacyclic triterpenoid 2-(3-phenylprop-2-en-1-ylidene)-22β-hydroxy-3-oxoolean-12-en-28-oic acid: an in vitro and in vivo study.
PubMed:Lantadene A content and toxicity of the lantana plant (Lantana camara, Linn.) to guinea pigs.
PubMed:A relationship between hepatic metabolism of reduced lantadene A and its toxicity in rats and sheep.
PubMed:Lantadene A toxicity in sheep. A model for cholestasis.
PubMed:Lantadene A, the active principle of Lantana camara L.; isolation of lantadene B, and the oxygen functions of lantadene A and lantadene B.
PubMed:Inhibition of biliary secretion by icterogenin and related triterpenes. II. Effect of icterogenin, crude rehmannic acid, oleanolic acetate and "mixed lippia acids" on mitochondria isolated from biliary fistula rabbits receiving the triterpenes.
PubMed:Inhibition of biliary secretion by icterogenin and related triterpenes. I. Effect of icterogenin, rehmannic acid and oleanolic acetate on liver mitochondria in vitro.
PubMed:Observation of metabolites of reduced lantadene A in bile canalicular membranes of rats with triterpene-induced cholestasis.
PubMed:Studies on the mechanism of toxicity of reduced lantadene A in rats.
PubMed:Toxicity of reduced lantadene A (22 beta-angeloyloxyoleanolic acid) in the rat.
PubMed:Leishmanicidal Triterpenes from Lantana camara.
PubMed:Nematicidal Triterpenoids from Lantana camara.
PubMed:Isolation and partial purification of Lantana (Lantana camara L.) toxins.
PubMed:Novel lung adenocarcinoma and nuclear factor-kappa B (NF-κB) inhibitors: synthesis and evaluation of lantadene congeners.
PubMed:Novel dual inhibitors of nuclear factor-kappa B (NF-κB) and cyclooxygenase- 2 (COX-2): synthesis, in vitro anticancer activity and stability studies of lantadene-non steroidal anti-inflammatory drug (NSAID) conjugates.
PubMed:The oral toxicity for sheep of triterpene acids isolated from Lantana camara.
PubMed:Biotransformation of lantadenes, the pentacyclic triterpenoid hepatotoxins of lantana plant, in guinea pig.
PubMed:Toxicity of isolated Lantana (Lantana camara L) constituents to male and female guinea pigs.
PubMed:Biological action of lantadene C, a new hepatotoxicant from Lantana camara var. aculeata.
PubMed:Chemopreventive activity of lantadenes on two-stage carcinogenesis model in Swiss albino mice: AP-1 (c-jun), NFkappaB (p65) and P53 expression by ELISA and immunohistochemical localization.
PubMed:[Studies on the chemical constituents of the leaves of Lantana camara].
PubMed:Vaccination as a possible means of preventing lantana poisoning.
PubMed:Current ideas on the pathophysiology and treatment of lantana poisoning of ruminants.
PubMed:Levels of lantadenes, bioactive pentacyclic triterpenoids, in young and mature leaves of Lantana camara var. aculeata.
PubMed:Comparison of lantadenes content and toxicity of different taxa of the lantana plant.
PubMed:Triterpenes of toxic and non-toxic taxa of Lantana camara.
PubMed:[Antifeeding effects of crude lantadene from Lantana camara on Plutella xylostella and Spodoptera litura larvae].
PubMed:Antitubercular activity of triterpenoids from Lippia turbinata.
PubMed:Fragility of erythrocytes in animals affected by lantana poisoning.
PubMed:A review of the hepatotoxic plant Lantana camara.
PubMed:Antimycobacterial triterpenoids from Lantana hispida (Verbenaceae).
PubMed:Evaluation of antimotility effect of Lantana camara L. var. acuelata constituents on neostigmine induced gastrointestinal transit in mice.
PubMed:Effect of Lantana camara toxicity on lipid peroxidation in guinea pig tissues.
PubMed:A review of the toxicity of Lantana camara (Linn) in animals.
 
Notes:
toxic principle, triterpene acid from lantana camara.
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