152243-70-4

Basic information

• Product Name: Uncargenin C
• Synonyms: Uncargenin C
• CAS NO: 152243-70-4
• Molecular Formula: C30H48O5
• Molecular Weight: 488.7
• Mol File: 152243-70-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Uncargenin C(CAS DataBase Reference)
• NIST Chemistry Reference: Uncargenin C(152243-70-4)
• EPA Substance Registry System: Uncargenin C(152243-70-4)

Safety Data

• Hazardous Substances Data: 152243-70-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Uncargenin C is used as a potential anti-cancer agent for its ability to inhibit the growth of various cancer cell lines, including leukemia. Its potent cytotoxic properties make it a promising candidate for the development of new cancer treatments.
Used in Neuroprotection:
Uncargenin C is used as a neuroprotective agent due to its demonstrated neuroprotective effects, which could be beneficial in the treatment of neurological disorders and conditions.
Used in Anti-Inflammatory Applications:
Uncargenin C is used as an anti-inflammatory agent, leveraging its anti-inflammatory properties to potentially treat inflammatory conditions and diseases.
Each of these uses highlights a different aspect of Uncargenin C's potential based on the biological activities it has been observed to possess. Further research and development are necessary to fully realize its therapeutic potential across these applications.

Upstream product

• 1332859-40-1 3β,6β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside 
• 18156-74-6 1-(Trimethylsilyl)imidazole 
• 508-02-1 Oleanolic acid 
• 13016-53-0 12α-bromo-3β,13β-dihydroxyolean-28-oic acid γ-lactone 
• 89503-61-7 12α-bromo-3-oxoolean-28β→13β olide 

Relevant articles and documents

Cytotoxic triterpene saponins from the stem bark of Kalopanax pictus

Three new compounds, 3β,6β,23-trihydroxyolean-12-en-28-oic acid 3-O-α-l-arabinopyranoside (1), kalopanaxsaponin L (2), and kalopanaxsaponin M (13), as well as eleven known compounds (3-12 and 14), were isolated from the stem bark of Kalopanax pictus. Their structures were determined on the basis of extentive spectroscopic analyses and acid hydrolysis. The cytotoxicity of the compounds was evaluated in three human carcinoma cell lines, including HL-60, HCT-116, and MCF-7. Compounds 1, 5-8, 10, and 11 exhibited significantly cytotoxic activity toward HL-60 cells, with IC 50 values ranging from 0.1 to 6.9 μM. Compounds 4-7 and 14 showed significant cytotoxicity against HCT-116 cells, with IC50 values ranging from 0.4 to 9.2 μM. Remarkably, the cytotoxic activities of compounds 5-7 against HCT-116 cells were greater than that of the anticancer chemotherapy drug, mitoxantrone (IC50 = 3.7 μM). Compounds 1, 3, 5, and 14 were cytotoxic toward MCF-7 cells with IC50 values in a range of 7.4-14.5 μM.

Anti-inflammatory triterpenoid saponins from the stem bark of Kalopanax pictus

Five new compounds, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3-2-en-28-oic acid 28-O-β-d-glucopyranoside (3), 3-O-[2,3-di-O-acetyl-α-l- arabinopyranosyl]hederagenin 28-O-α-L-rhamnopyranosyl-(→4)-β-d- glucopyranosyl-(→6)-β-d-glucopyranoside (4), and 3-O-[3,4-di-O-acetyl- α-l-arabinopyranosyl]hederagenin 28-O-α-L-rhamnopyranosyl-(→4)- β-d-glucopyranosyl-(→6)-β-d-glucopyranoside (5), as well as 10 known compounds (6-15), were isolated from the stem bark of Kalopanax pictus. Compounds 1-5 and 7-14 inhibited TNFα-induced NF-κB transcriptional activity in HepG2 cells in a dose-dependent manner, with IC50 values ranging from 0.6to 16.4 μM. Furthermore, the transcriptional inhibitory function of these compounds was confirmed on the basis of decreases in COX-2 and iNOS gene expression in HepG2 cells. The structure-activity relationship of the compounds with respect to anti-inflammatory activity is also discussed.

Application of Relay C?H Oxidation Logic to Polyhydroxylated Oleanane Triterpenoids

Although clinical applications of abundant feedstock triterpenoids such as oleanolic acid are limited because of poor solubility and bioavailability, synthetic access to higher hydroxylated oleanane terpenoids is challenging. We now report the use of relay C?H oxidation logic to mimic the processes carried out in nature by P450 monooxygenase enzymes. To this end, we used the C-23-OH as natural handle for a hydrogen-atom transfer to access C-6, enabling the first syntheses of highly oxidized natural products uncargenin C and protobassic acid as well as uncovering the anti-leukemic activity of a synthetic intermediate. Chemical modification of readily available, scarcely oxidized natural products not only enables access to higher and more valuable congeners but can also pave the way to pharmaceutically relevant derivatives with enhanced properties. Achieving site-selective oxidation of such natural products is an endeavor often controlled by the presence of directing elements. Because of this fact, the oxidation of C?H bonds remote from such elements is either unfeasible or requires more elaborate synthetic strategies. We report the use of relay C?H oxidation as a concept to achieve the oxidation of previously inaccessible ring B in the abundant feedstock oleanolic acid. This resulted not only in the first total synthesis of a number of polyhydroxylated natural triterpenoids but also revealed an anti-leukemic intermediate. The strategy presented here could become a very general approach in the synthesis of valuable triterpenoids. Although biological applications of abundant feedstock triterpenoids such as oleanolic acid are limited because of poor solubility, synthetic access to higher hydroxylated metabolites is challenging. We use relay C?H oxidation logic to mimic the processes carried out in Nature by P450 monooxygenase enzymes. To this end, we use the C-23-OH as natural handle for a hydrogen-atom-transfer access to C-6, enabling the first syntheses of highly oxidized natural products as well as uncovering the anti-leukemic activity of a synthetic intermediate.