reynosin and santamarine

In the work described here, a number of sesquiterpenes and benzoxazinoids from natural sources, along with their easily accessible derivatives, were evaluated against the main protease, RNA replicase and spike glycoprotein of SARS-CoV-2 by molecular docking. These natural products and their derivatives have previously shown remarkable antiviral activities. The most relevant compounds were the 4-fluoro derivatives of santamarine, reynosin and 2-amino-3

Topics: Antiviral Agents; Benzoates; Benzoxazines; Biological Products; Coronavirus 3C Proteases; COVID-19; Humans; Hydrogen; Ligands; Molecular Docking Simulation; Molecular Dynamics Simulation; Protease Inhibitors; RNA-Dependent RNA Polymerase; SARS-CoV-2; Sesquiterpenes; Spike Glycoprotein, Coronavirus

Tuberculosis is primarily caused by Mycobacterium tuberculosis (Mtb). Previous studies have shown that the dichloromethanic extract of Ambrosia confertiflora DC (Asteraceae) inhibited Mtb.. To isolate the compounds responsible for the mycobactericidal activity against clinical Mtb strains.. The dichloromethanic extract of aerial parts of A. confertiflora was separated using chromatography columns. Mycobactericidal activity of the isolated compounds was evaluated using the Alamar Blue bioassay (128-16 μg/mL, 7 days). Cytotoxicity was tested against normal cell line L929 using the MTT ([3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium]) assay (100-3.125 μg/mL, 48 h). Compound structures were elucidated by. Two sesquiterpene lactones (SQLs) with mycobactericidal activity were identified: santamarine and reynosin. Reynosin was the most active compound, with a minimal bactericidal concentration (MBC) of 128 μg/mL against the H37Rv, 366-2009 and 104-2010 Mtb strains and a minimal inhibitory concentration (MIC) of 64, 64, 128, 128 and 128 μg/mL against the H37Rv, 104-2010, 63-2009, 366-2009 and 430-2010 Mtb strains, respectively. Santamarine had MBCs of 128 μg/mL against the H3Rv and 104-2010 Mtb strains and MICs of 128 μg/mL against the H37Rv, 366-2009 and 104-2010 Mtb strains. We also isolated 1,10-epoxyparthenolide but only showed mycobacteriostatic activity (MIC 128 μg/mL) against the Mtb strain. Compounds were tested against the L929 cell line and the calculated selectivity index was <1.. This is the first report of the mycobactericidal activity of these compounds against clinical Mtb strains. It is also the first report of the isolation of 1,10-epoxyparthenolide from A. confertiflora. The anti-mycobacterial activity of A. confertiflora was attributed to the SQLs identified.

Topics: Ambrosia; Humans; Microbial Sensitivity Tests; Mycobacterium tuberculosis; Sesquiterpenes

To screen the potential hepatotoxic components in Chinese herb medicine Aucklandiae Radix.. The potential hepatotoxic components were screened using HepG2 cells labeled with fluorescein diacetate from 25 fractions of Aucklandiae Radix, in which the hepatotoxic compounds were further identified with GC-MS.. Ten potential hepatotoxic fractions were screened. The identification results by GC-MS indicated that the main compounds in C09 were dehydrocostuslactone, santamarine (or magnolialide) and reynosin, and in C11 were α-costol and elemol.. Dehydrocostuslactone, santamarine (or magnolialide), reynosin, α-costol and elemol are potential hepatotoxic compounds in Aucklandiae Radix.

Topics: Drugs, Chinese Herbal; Gas Chromatography-Mass Spectrometry; Lactones; Sesquiterpenes

To study the chemical constituents of Dolomiaea souliei.. Various chromatographic techniques were adopted to separate the constituents, and the spectrum analysis was made to identify their structures.. Seventeen compounds were isolated and identified as: dehydrocostus lactone (1), costunolide (2), mokko lactone (3), santamarine(4), reynosin (5), 4alpha-hydroxy-4beta-methyldihydrocostol (6), sulfocostunolide A (7), beta-costic acid (8), beta-cyclocostunolide (9), vladinol A (10), ursolic acid (11), betulinic acid (12), betulin (13), dibutyl terephthalate (14), dibutyl phthalate (15), uridine (16), and emodin (17).. Compounds 6-9 and 12-17 were obtained from this genus for the first time, and compound 11 was obtained from this plant for the first time.

Topics: 4-Butyrolactone; Asteraceae; Betulinic Acid; Emodin; Lactones; Pentacyclic Triterpenes; Sesquiterpenes; Triterpenes; Ursolic Acid

Total methanol extract of Saussurea lappa radix (Compositae) showed potent inhibitory effect on the production of tumor necrosis factor-alpha (TNF-alpha), a proinflammatory cytokine, in murine macrophage-like cell (RAW264.7 cells) in our previous screening studies on 120 Korean medicinal plants. The activity-guided purification of the plant resulted in the isolation of three components. The chemical structures of the components isolated were established by spectroscopic analyses as sesquiterpene lactones [cynaropicrin (1), reynosin (2), and santamarine (3)]. These three compounds inhibited TNF-alpha production in a dose-dependent manner. The molar concentrations of cynaropicrin, reynosin, and santamarine producing 50% inhibition (IC50) of TNF-alpha production were 2.86 micrograms/ml (8.24 microM), 21.7 micrograms/ml (87.4 microM), and 26.2 micrograms/ml (105 microM), respectively. However, treatment with sulphydryl (SH) compounds such as L-cysteine, dithiothreitol, and 2-mercaptoethanol abrogated the inhibitory effect of cynaropicrin on TNF-alpha production. Therefore, we conclude that the principal inhibitory component of Saussurea lappa is cynaropicrin and its inhibitory effect is mediated through conjugation with SH-groups of target proteins.

Topics: Animals; Cell Line; Lactones; Mice; Molecular Structure; Plants, Medicinal; Sesquiterpenes; Tumor Necrosis Factor-alpha

The germacranolide sesquiterpene lactones costunolide, parthenolide, and costunolide diepoxide were isolated from the leaves of Magnolia grandiflora L. Costunolide diepoxide might be, at least in part, an artifact derived from air oxidation of parthenolide. The root bark yielded only costunolide together with the two eudesmanolides, santamarine and reynosin. In an attempt to synthesize costunolide diepoxide, the action of m-chloroperbenzoic acid on parthenolide and on costunolide was studied. The products were costunolide diepoxide from parthenolide and the two cyclized derivatives, santamarine and reynosin, from costunolide. The elusive 1,10-epoxide was obtained by epoxidizing costunolide using a biphasic system containing sodium bicarbonate. Under these conditions, epoxidation of costunolide took place without cyclization.

Topics: Cyclization; Epoxy Compounds; Lactones; Oxidation-Reduction; Plant Extracts; Sesquiterpenes