13224-63-0

Usage

General Description

22 beta-angeloyloxyoleanolic acid is a triterpenoid compound found in natural sources such as the plants of the genus Tabebuia. It possesses potential medicinal properties and has been studied for its anti-inflammatory, anti-microbial, and anti-cancer activities. The compound has shown inhibitory effects on tumor cell growth and has demonstrated anti-inflammatory effects by reducing the production of pro-inflammatory mediators. Additionally, 22 beta-angeloyloxyoleanolic acid has shown promising antimicrobial activity against various pathogens, making it a potential candidate for the development of new therapeutic agents. Overall, 22 beta-angeloyloxyoleanolic acid holds potential for pharmaceutical and medicinal application due to its diverse therapeutic properties.

InChI:InChI=1/C35H54O5/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/h10-11,23-27,36H,12-20H2,1-9H3,(H,38,39)/b21-10+/t23-,24?,25-,26+,27-,32+,33-,34-,35+/m1/s1

Upstream product

• 467-81-2 lantadene A 

Relevant academic research and scientific papers

Reduced Lantadenes A and B: Semi-synthetic synthesis, selective cytotoxicity, apoptosis induction and inhibition of NO, TNF-α production in HL-60 cells

The aim of this study was to investigate the effect of pentacyclic triterpenoids-reduced Lantadenes A (3) and B (4) on the cytotoxicity, stimulation of apoptosis and regulation of transcription factors in HL-60 cells. The 3 and 4 are the minor compounds of weed Lantana camara L. (Verbenaceae) and were prepared semi-synthetically in single step by reducing Lantadenes A (1) and B (2) under microwave irradiation with yield of 98-99 %. The 3 and 4 demonstrated selective cytotoxicity against HL-60, MCF-7, HSC-2, and HCT-116 cancer cell lines (IC50 1.2-6.4 μM) and were found non-toxic toward normal cells (VERO) with IC50 >50). The compounds 3 and 4 (15 μM)-induced apoptosis by activation of caspase-3 and bax, along with significant decrease in expression of NF-kB (p-65) and bcl-2 in HL-60 cells. The compounds 3 and 4 at 15 μM significantly suppressed the production of nitrite, TNF-α, and iNOS gene expression in HL-60 cells. The results suggested that reduced Lantadenes A and B have the potential to be developed as anticancer agents.

Synthesis and in vitro anticancer studies of novel C-2 arylidene congeners of lantadenes

The antitumor pentacyclic triterpenoids, Lantadene A (1) and B (2) were isolated from the leaves of weed Lantana camara L. (Verbenaceae) and were structurally transformed to bioactive intermediates 3-6. The Claisen-Schmidt reaction of 22β-hydroxy-3-oxoolean-12-en-28-oic acid (5) with requisite aldehydes afforded 2-arylidene-22β-hydroxy-3-oxoolean-12-en-28-oic acids (7-16). The compounds were evaluated for their in-vitro anticancer activity by National Cancer Institute (NCI), USA and some of these compounds showed marked cytotoxicity in micromolar range. The mean graph midpoint (MG-MID) value of compound 3 (MG-MID -5.69) was higher than standard drug cisplatin (MG-MID -5.66) while comparable in case of compound 12 (MG-MID -5.52). The NCI's COMPARE molecular mechanistic analysis showed that these compounds were in significant correlations with activity patterns of mechanistic set of compounds (PCC ≥ 0.60).