Auranamide

Anti-Inflammatory Effects of Auranamide and Patriscabratine-Mechanisms and In Silico Studies.[Pubmed:35956947]

Molecules. 2022 Aug 5;27(15):4992.

Auranamide and patriscabratine are amides from Melastoma malabathricum (L.) Smith. Their anti-inflammatory activity and nuclear factor erythroid 2-related factor 2 (NRF2) activation ability were evaluated using Escherichia coli lipopolysaccharide (LPSEc)-stimulated murine macrophages (RAW264.7) and murine hepatoma (Hepa-1c1c7) cells, respectively. The cytotoxicity of the compounds was assessed using a 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide (MTT) assay. The anti-inflammatory activity was determined by measuring the nitric oxide (NO) production and pro-inflammatory cytokines (Interleukin (IL)-1beta, Interferon (IFN)-gamma, tumour necrosis factor (TNF)-alpha, and IL-6) and mediators (NF-kappaB and COX-2). NRF2 activation was determined by measuring the nicotinamide adenine dinucleotide phosphate hydrogen (NADPH) quinone oxidoreductase 1 (NQO1), nuclear NRF2 and hemeoxygenase (HO)-1. In vitro metabolic stability was assessed using the mouse, rat, and human liver microsomes. The compounds were non-toxic to the cells at 10 muM. Both compounds showed dose-dependent effects in downregulating NO production and pro-inflammatory cytokines and mediators. The compounds also showed upregulation of NQO1 activity and nuclear NRF2 and HO-1 levels. The compounds were metabolically stable in mouse, rat and human liver microsomes. The possible molecular targets of NRF2 activation by these two compounds were predicted using molecular docking studies and it was found that the compounds might inhibit the Kelch domain of KEAP1 and GSK-3beta activity. The physicochemical and drug-like properties of the test compounds were predicted using Schrodinger small molecule drug discovery suite (v.2022-2).

LC-DAD-MS-based metabolite profiling of three species of Justicia (Acanthaceae).[Pubmed:23126522]

Nat Prod Res. 2013 Aug;27(15):1335-42.

Olean-12-en-3beta-24 diol (A), Auranamide (B), aurantiamide acetate (C), 2alpha,3beta-dihydroxy-olean-12-en-28-oic acid (D) and quindoline (E) were isolated from the dichloromethane (CH2Cl2) extract of the stems of Justicia secunda (Acanthaceae). Liquid chromatography with ultraviolet and mass spectrometric detection was used to acquire more knowledge of the chemical composition of this extract and to monitor variations in profiles of both the isolated and the other non-identified compounds in Justicia refractifolia and Justicia graciliflora. The compound classes, phenolic and olefinic amides, feruloyltyramine amides, 2,5-diaryl-3,4-dimethyltetrahydrofuranoid lignans, peptide alkaloids, phenylalanine derivatives, conjugated ynones, indolquinoline alkaloids, triterpenes and pigments, were tentatively identified based on the LC-DAD-APCI-MS analysis. The most frequently encountered compound among the species was Auranamide while the distribution of quindoline was limited to J. secunda. Moreover, the acetylcholinesterase inhibitory activity of the isolated compounds was determined.

Chemical constituents of the leaf of Alpinia mutica Roxb.[Pubmed:22946537]

Nat Prod Res. 2013;27(16):1468-70.

Hydrodistillation of the fresh leaves of Alpinia mutica afforded 0.005% colourless essential oil. GC and GC-MS analysis revealed the presence of 33 components accounting for 92.9% of the total oil, dominated by 20 sesquiterpenes (76.7%) and 10 monoterpenes (8.3%). The major constituent was found to be beta-sesquiphellandrene which was 29.2% of the total oil. Soxhlet extraction, followed by repeated column chromatography of the dried leaves yielded two phenolic compounds, identified as 5,6-dehydrokawain and aniba dimer A, together with one amide assigned as Auranamide. The structures of these compounds were determined by using spectroscopic analysis. Antibacterial screening of the essential oil, the crude and isolated compounds showed weak to moderate inhibitory activity.

Amides, triterpene and flavonoids from the leaves of Melastoma malabathricum L.[Pubmed:20582481]

J Nat Med. 2010 Oct;64(4):492-5.

Successive extraction of the dried leaves of Melastoma malabathricum, followed by purification using repeated chromatographic techniques, yielded six compounds, including two amides, Auranamide and patriscabratine, a triterpene, alpha-amyrin, and three flavonoids, quercitrin, quercetin and kaempferol-3-O-(2'',6''-di-O-p-trans-coumaroyl)-beta-glucoside. Their structures were elucidated by spectroscopic means and also by direct comparison of their spectroscopic data with respective published data. These three phenolic constituents were found to be active as free radical scavengers, with quercetin being the strongest radical scavenger, having an IC(50) value of 0.69 microM in the UV method. Quercitrin and kaempferol-3-O-(2'',6''-di-O-p-trans-coumaroyl)-beta-glucoside showed moderate radical scavenging, with IC(50) values of 74.1 and 108.8 microM, respectively.

Cytotoxic and anti-HIV principles from the rhizomes of Begonia nantoensis.[Pubmed:14993759]

Chem Pharm Bull (Tokyo). 2004 Mar;52(3):345-9.

Three new compounds: begonanline (1). nantoamide (2). and methyl (S)-glycerate (3). as well as forty-four known compounds have been isolated and characterized from the rhizomes of Begonia nantoensis. The structures of these compounds were determined by spectral analyses and/or X-ray crystallography. Among them, cucurbitacin B (4). dihydrocucurbitacin B (5). cucurbitacin E (6). dihydrocucurbitacin E (7). cucurbitacin I (8). and (-)-Auranamide (9). showed cytotoxicity against four human cancer cell lines. 3beta,22alpha-Dihydroxyolean-12-en-29-oic acid (10), indole-3-carboxylic acid (11), 5,7-dihydroxychromone (12), and (-)-catechin (13) demonstrated significant activity against HIV replication in H9 lymphocyte cells.