2',4'-Dihydroxydihydrochalcone

Galenia africana plant extract exhibits cytotoxicity in breast cancer cells by inducing multiple programmed cell death pathways.[Pubmed:33132708]

Saudi Pharm J. 2020 Oct;28(10):1155-1165.

Globally, breast cancer is the most common malignancy in women and the second most common cause of cancer-related death among women. There is therefore a need to identify more efficacious therapies for this neoplasm. Galenia africana (Kraalbos) is a perennial shrub found in Southern Africa and is used by the indigenous people to treat various ailments. There has therefore been much interest to establish the scientific basis for the medicinal properties of Kraalbos. This study aimed to investigate and characterise the anti-cancer activity of an ethanolic extract of Kraalbos leaves, KB2, against oestrogen receptor positive (MCF-7) and triple negative (MDA-MB-231) breast cancer cells. LC-MS/MS analyses identified the phytochemicals 7'-hydroxyflavanone, 5',7'-dihydroxyflavanone, 2',4'-dihydroxydihydrochalcone and 2',4'-dihydroxychalcone in KB2. KB2 exhibited an IC50 of 114 microg/ml and 130.5 microg/ml in MCF-7 and MDA-MB-231 cells respectively, selectively inhibited their long-term survival and reduced their migration which correlated with a decrease in EMT markers. It induced oxidative stress (ROS), DNA damage (increased levels of gamma-H2AX), and triggered cell cycle arrests in MCF-7 and MDA-MB-231 cells. Importantly, KB2 activated intrinsic (cleaved caspase 9) and extrinsic (cleaved caspase 8) apoptosis, necroptosis (p-RIP3 and the downstream target of the necrosome, pMLKL) and autophagy (LC3II). Co-treatment of the breast cancer cells with KB2 and the autophagy inhibitor bafilomycin A1 resulted in a significant increase in cell viability which suggests that KB2 induced autophagy is a cell death mechanism.

Synthesis and Anti-Saprolegnia Activity of New 2',4'-Dihydroxydihydrochalcone Derivatives.[Pubmed:32532060]

Antibiotics (Basel). 2020 Jun 10;9(6). pii: antibiotics9060317.

In the present study, seven 2',4'-dihydroxydihydrochalcone derivatives (compounds 3-9) were synthesized and their capacity as anti-Saprolegnia agents were evaluated against Saprolegnia parasitica, S. australis, S. diclina. Derivative 9 showed the best activity against the different strains, with minimum inhibitory concentration (MIC) and minimum oomyceticidal concentration (MOC) values between 100-175 mug/mL and 100-200 mug/mL, respectively, compared with bronopol and fluconazole as positive controls. In addition, compound 9 caused damage and disintegration cell membrane of all Saprolegnia strains over the action of commercial controls.

Cytotoxic activity of dihydrochalcones isolated from Corema album leaves against HT-29 colon cancer cells.[Pubmed:24273860]

Nat Prod Commun. 2013 Sep;8(9):1255-6.

During our search for cytotoxic compounds from Andalusian vascular plants, the ethyl acetate extract from the leaves of Corema album (L.) D. Don (Ericaceae) was selected for its cytotoxic activity against the HT-29 human colon adenocarcinoma cell line. Two dihydrochalcones, 2',4'-dihydroxydihydrochalcone (1) and 2'-methoxy-4'-hydroxydihydrochalcone (2), have been isolated from the leaves of C. album. Their structural identification was based on 1H NMR and 13C NMR data, including 2D NMR, and mass spectrometry. These compounds were subjected to the sulfhorhodamine B (SRB) cytotoxic assay against human colon adenocarcinoma cells (HT-29). Compounds 1 and 2 showed higher cytotoxicity than the positive control 5-fluorouracil (5-FU); the IC50 values (microM +/- SEM) were 1.8 +/- 0.4 for compound 1, 8.5 +/- 2.1 microM for compound 2, and 8.7 +/- 4.0 for 5-FU. The cytotoxic activity of 1 and 2 was reduced in the presence of the antioxidants N-acetylcysteine (NAC) and Mn(III) Tetrakis(1-methyl-4-pyridyl) porphyrin pentachloride (MnTMPyP), therefore suggesting that reactive oxygen species generation participates in the cytotoxic activity of these dihydrochalcones.

Determination of seven flavonoids in Ixeridium gracile (DC.) Shih by high-performance liquid chromatography.[Pubmed:19610366]

J AOAC Int. 2009 May-Jun;92(3):773-8.

A high-performance liquid chromatographic technique coupled with photodiode array detection was proposed for the simultaneous determination of 7 flavonoids, i.e., quercetin, kaempferol, 7-hydroxyflavanone, 7-methoxyflavanone, 2',4'-dihydroxychalcone, 2',4'-dihydroxydihydrochalcone, and 7,2'-dihydroxy-3', 4'-dimethoxyisoflavane, in extracts of the plant Ixeridium gracile. Optimum separation was obtained by using a reversed-phase C18 method. Because of the different UV characteristics of these components, 5 detection wavelengths were used for the quantitative analysis. All of the flavonoids showed good linearity (r > 0.9999). The limit of detection and limit of quantitation values for the analytes ranged from 0.06 to 0.46 microg/mL and from 0.18 to 1.48 microg/mL, respectively. The method was validated by evaluating repeatability, precision, stability, and accuracy. Five different extraction and purification procedures were investigated for preparation of the sample solution. The optimized method was applied to the determination of flavonoids in I. gracile and was found to be efficient.