6060-06-6

Usage

Uses

Used in Pharmaceutical Industry:
Platanic acid is used as an anti-HIV agent for its ability to inhibit the replication of the human immunodeficiency virus (HIV), thus helping in the treatment and management of HIV/AIDS.
Used in Drug Development:
Platanic acid is used as a potential candidate for drug development due to its unique chemical structure and biological activity. Its properties can be further explored and optimized for the development of new therapeutic agents targeting various diseases and conditions.

InChI:InChI=1/C29H46O4/c1-17(30)18-9-14-29(24(32)33)16-15-27(5)19(23(18)29)7-8-21-26(4)12-11-22(31)25(2,3)20(26)10-13-28(21,27)6/h18-23,31H,7-16H2,1-6H3,(H,32,33)/t18-,19+,20-,21+,22-,23+,26-,27+,28+,29-/m0/s1

Upstream product

• 473-98-3 betulin 
• 7790-28-5 sodium periodate 
• 472-15-1 Betulinic acid 

Downstream Products

• 4356-32-5 methyl (3β)-3-hydroxy-20-oxo-30-norlupan-28-oate 

Relevant academic research and scientific papers

Platanic Acid-Aryl Enones as Potential Anticancer Compounds: Synthesis and Biological Profiling against Breast, Prostate and Lung Cancer Cell Lines

A series of rationally designed platanic acid-based compounds derived from naturally occurring betulinic acid were synthesized through a sequence of Lemieux-Johnson oxidation and Aldol condensation reaction. All the compounds were screened for cytotoxicity against a panel of human cancer and normal cell lines using MTT assay. From the biological data, it was observed that some of these semi-synthetic congeners exhibited potent biological profiles compared to platanic acid. One of the compounds with the p-tolyl substitution was found to be most active in this study, and its cytotoxicity against two of the cell lines, MDA-MB 231 and A-549 were in tune with the standard compound, 5-fluorouracil.

Synthesis and α-Glucosidase Inhibitory Activity of Ursolic Acid, Lupeol, and Betulinic Acid Derivatives

Seven synthetic derivatives of ursolic acid, lupeol, and betulinic acid (1a–1b, 2a–2b, and 3a–3c) were synthesized to study their α-glucosidase inhibitory activity. Three of them (2b, 3b, and 3c) are new compounds. Among the synthetic derivatives, betulinic acid analogues 3b and 3c exhibited the best activity against α-glucosidase and is superior to the positive agent, with IC50 values of 35.0 ± 3.37 and 34.0 ± 1.24 μM, respectively.

Synthetic Analogues of Betulinic Acid as Potent Inhibitors of PS1/BACE1 Interaction to Reduce Aβ Generation

The lupane-type triterpenoids are endowed with a wide range of biological activities such as antiviral, anti-inflammatory and anticancer activity. We describe here its potential application in Alzheimer's disease (AD) treatment as an inhibitor of PS1/BACE1 interaction. 3-α-Akebonoic acid, which emanated from a high throughput screening (HTS), was discovered to interfere with PS1/BACE1 interaction and reduce amyloid β-protein (Aβ) production. In view of the limited source, we instead used naturally rich betulinic acid (compound 2) as starting material for lead optimization and a focused library of its derivatives was constructed to gain a better understanding of the structure activity relationship (SAR) of triterpenoid-type inhibitor of PS1/BACE1 interaction. Compound 22 was finally chosen as the most potent PS1/BACE1 interaction inhibitor, which reduced Aβ generation effectively.

Preparation of betulinic acid derivatives by chemical and biotransformation methods and determination of cytotoxicity against selected cancer cell lines

Several novel 2,4-dinitrophenylhydrazone betulinic acid derivatives have been prepared by chemical and biotransformation methods using fungi and carrot cells. Some compounds showed significant cytotoxicity and selectivity against some tumor cell lines. The most active, 3-[(2,4-dinitrophenyl)hydrazono]lup- (20R)-29-oxolupan-28-oic acid, showed IC50 values between 1.76 and 2.51 μM against five human cancer cell lines. The most selective, 3-hydroxy-20-[(2,4-dinitrophenyl)hydrazono]-29-norlupan-28-oic acid, was five to seven times more selective for cancer cells when compared to fibroblasts. Cell cycle analysis and apoptosis induction were studied for the most active derivatives.

Structure - Activity relationship study of betulinic acid, a novel and selective TGR5 agonist, and its synthetic derivatives: Potential impact in diabetes

We describe here the biological screening of a collection of natural occurring triterpenoids against the G protein-coupled receptor TGR5, known to be activated by bile acids and which mediates some important cell functions. This work revealed that betulinic (1), oleanolic (2), and ursolic acid (3) exhibited TGR5 agonist activity in a selective manner compared to bile acids, which also activated FXR, the nuclear bile acid receptor. The most potent natural triterpenoid betulinic acid was chosen as a reference compound for an SAR study. Hemisyntheses were performed on the betulinic acid scaffold, and we focused on structural modifications of the C-3 alcohol, the C-17 carboxylic acid, and the C-20 alkene. In particular, structural variations around the C-3 position gave rise to major improvements of potency exemplified with derivatives 18 dia 2 (RG-239) and 19 dia 2. The best derivative was tested in vitro and in vivo, and its biological profile is discussed.

Synthesis and evaluation of biological activity of the auaternary ammonium salts of lupane-, oleanane-, and ursane-type acids

The anticancer properties of the derivatives of natural pentacyclic triterpenoids have received much attention recently. Here we present the preparation and the evaluation of the anticancer activity of a novel group of derivatives: quaternary ammonium esters. The esters were synthesized by quaternization of the respective 2-bromoethyl esters of betulinic, dihydrobetulinic, platanic, oleanolic, ursolic, and 3-acetoxy-21-oxolup-18-en- 28-oic acids with common low-molecular-weight tertiary amines, namely trimethylamine, triethylamine, pyridine, and triethanolamine. However, the desired quaternary salts were obtained only from trimethylamine, triethylamine, and pyridine. In case of the reaction with triethanol?amine the elimination of one of the 2-hydroxyethyl groups occurred and only tertiary amines were formed. Most of the prepared compounds showed significant in vitro cytotoxic activity on the CEM T-lymfoblastic leukaemia cell line. Three of the six selected compounds {2-(triethylammonio)ethyl 3-hydroxylup-20(29)-en-28-oate bromide, 2-(triethylammonio)ethyl 3b-hydroxylupan-28-oate bromide and 2-[bis(2-hydroxyethyl)amino]ethyl 3-hydroxylupan-28-oate] exhibited strong cytotoxic activity on a panel of ten cell lines, including drug resistant. Georg Thieme Verlag Stuttgart · New York.

Synthesis of glycosides of lupane-type triterpene acids

A preparative synthesis of glucosides of the lupane-type triterpene acids betulinic, dihydrobetulinic, betulonic, dihydrobetulonic, and 3,20-dioxo-30-norlupan-28-oic was proposed. Glycosylation of 3-hydroxyacids by α-acetobromoglucose (ABG) with Ag2O was performed in pyridine (Py) to form glycosides at C-28, repeated glycosylation of which by these same reagents but in CH2Cl2 generated a glycoside bond at C-3 to form bisglucosides. 28-Glucosides of ketoacids were formed in high yields in both Py and CH2Cl2.

Development of C-20 modified betulinic acid derivatives as antitumor agents

Chemical modifications were performed on C-20 position of betulinic acid for a structure-activity relationship study. The evaluation of the compounds using human colon carcinoma HCT-116, human prostate adenocarcinoma PC3, and human melanoma cell lines M14-MEL, SK-MEL-2, and UACC-257 did not show any selective cytotoxicity towards melanoma cells. The results from both MTT reduction assay and SRB staining assay were comparable that no remarkable differences in cytotoxicity profile of the compounds were noticed. The C-20 position was found to be sensitive to the size and the electron density of the substituents in retaining the cytotoxicity of betulinic acid and was found to be undesirable position to derivatize.

Three lupane derivatives from Leptospermum scoparium

The ether extract of the aerial parts of Leptospermum scoparium cultivars yielded a lactone with a 20,29,30-trinorlupane skeleton (1). Furthermore, 2α-hydroxyursolic acid (2), platanic acid (3) and 3β,30-dihydroxy-lup-20(29)-en-28-oic acid (4) were isolated.