Geometry optimization and GIAO (gauge including atomic orbitals) 13C NMR chemical shift calculations at Hartree–Fock level, using the 6-31G(d) basis set, are proposed as a tool to be applied in structural characterization of new organic compounds, thus providing useful support interpretation experimental data. Parameters related linear correlation plots computed versus shifts for fourteen low-polar natural products, containing 10–20 carbon atoms, were employed assess reliability structures....

Chemical investigation of the Et2O extract marine sponge Rhaphisia lacazei resulted in isolation 13 pure bisindole alkaloids (1−13). Compounds (1−6) belong to class topsentins and have already been described. 7−13 are new products, closely related hamacanthins. The major compounds 1−3 were tested vitro for antitumor activity; 2 3 showed antiproliferative activity against human broncopulmonary cancer cells (NSCLC-N6) with an IC50 12 6.3 μg/mL, respectively.

S. Forenza, L. Minale, R. Riccio and E. Fattorusso, J. Chem. Soc. D, 1971, 1129 DOI: 10.1039/C29710001129

The influence of the calculation method in mimicking experimental (13)C NMR chemical shifts 15 low-polarity natural products singularly containing 10-20 carbon atoms was investigated by employing different quantum chemistry approaches and basis sets, both preliminary geometry optimizations following single-point GIAO calculations shifts. geometries involved species were optimized at PM3, HF, B3LYP mPW1PW91 levels whereas parameters determined levels. Different combinations sets also tested....

Microsomal prostaglandin E2 synthase (mPGES)-1 catalyzes the transformation of PGH2 to PGE2 that is involved in several pathologies like fever, pain, and inflammatory disorders. To identify novel mPGES-1 inhibitors, we used silico screening rapidly direct synthesis, based on copper-catalyzed 3 + 2 Huisgen's reaction (click chemistry), potential inhibitors. We designed 26 new triazole-based compounds accordance with pocket binding requirements human mPGES-1. Docking results, agreement ligand...

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTFurther Brominated Bis- and Tris-Indole Alkaloids from the Deep-Water New Caledonian Marine Sponge Orina sp.Giuseppe Bifulco, Ines Bruno, Raffaele Riccio, Jacques Lavayre, Geneviève BourdyCite this: J. Nat. Prod. 1995, 58, 8, 1254–1260Publication Date (Print):August 1, 1995Publication History Published online1 July 2004Published inissue 1 August 1995https://pubs.acs.org/doi/10.1021/np50122a017https://doi.org/10.1021/np50122a017research-articleACS...

Ab initio calculations at the Hartree–Fock level with full-geometry optimization using 6-31G(d) basis set, and GIAO (gauge including atomic orbitals) 13C NMR chemical shifts, are presented here as a support in study of stereochemistry low-polar organic compounds having an open-chain structure. Four linear stereoisomers, fragments natural product previously characterized by experimental spectra, which possesses three stereogenic centers, 11 carbon atoms, 38 atoms total, were considered....

Abstract The present microreview highlights the recent goals reached by application of a combined approach NMR spectroscopy and quantum chemical methods in structural studies natural products. In particular, different case are reported, showing comparison calculated parameters at mechanical (QM) theory level with experimental data for configurational assignment organic compounds. Moreover, it is shown that QM–NMR can be used as fast convenient method to lead total synthesis complex products...

Among the phenolic compounds extracted from extra virgin olive oil, oleocanthal (1) has attracted considerable attention in modulation of many human diseases, such as inflammation and Alzheimer's disease (AD). Indeed, 1 is capable altering fibrillization tau protein, which one key factors at basis neurodegenerative covalently reacting with lysine ε-amino groups fragment K18 an unspecific fashion. In present study, investigation recognition process reaction profile between wild-type protein...

Oleocanthal (OLC) is a phenolic component of extra-virgin olive oil, recently supposed to be involved in the modulation some human diseases, such as inflammation and Alzheimer. In particular, OLC has been shown abrogate fibrillization tau protein, one main causes Alzheimer neurodegeneration. A recent interpretation this mechanism attempted on basis reactivity with fibrillogenic hexapeptide VQIVYK SDS-PAGE OLC/tau incubation mixtures, suggesting that covalent modification events modulate...

The 2-amine-9H-purine scaffold was identified as a weak bromodomain template and developed via iterative structure based design into potent nanomolar ligand for the of human BRD9 with small residual micromolar affinity toward BRD4. Binding lead compound 11 to results in an unprecedented rearrangement residues forming acetyllysine recognition site, affecting plasticity protein induced-fit pocket. does not exhibit any cytotoxic effect HEK293 cells displaces from chromatin bioluminescence...

Quantum mechanical/nuclear magnetic resonance (NMR) approaches are widely used for the configuration assignment of organic compounds generally comparing one cluster experimentally determined data (e.g.,

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPolycyclic Guanidine Alkaloids from the Marine Sponge Crambe crambe and Ca++ Channel Blocker Activity of Crambescidin 816R. G. S. Berlinck, J. C. Braekman, D. Daloze, I. Bruno, R. Riccio, Ferri, Spampinato, E. SperoniCite this: Nat. Prod. 1993, 56, 7, 1007–1015Publication Date (Print):July 1, 1993Publication History Published online1 July 2004Published inissue 1...

Dactylolide (1), a new cytotoxic 20-membered macrolide, was isolated from marine sponge of the genus Dactylospongia collected off coast Vanuatu islands. It co-occurred with other known bioactive macrolides: latrunculin A (2), laulimalide (3), isolaulimalide (4) and anthelminthic mycothiazole (5). The structure 1, which is minor metabolite, elucidated by spectroscopy (mainly 1D/2D NMR MS techniques). showed activity against L1210 SK-OV-3 tumor cell lines (63% 40% inhibition at 3.2 μg/mL).

With the aid of circular dichroism, n.m.r. shift reagents, and 13C spectroscopy absolute stereochemistry has been assigned to avarol {2-[(1R)-1,2,3,4,4a,7,8,8aα-octahydro-1β,2β,4aβ,5-tetramethyl-1-naphthylmethyl]-hydroquinone}, obtained from marine sponge Disidea avara. Avarol is first naturally occurring sesquiter-penoid 9,4-friedodrimane type be isolated.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTStructures of dictyodial and dictyolactone, unusual marine diterpenoidsJanet Finer, Jon Clardy, William Fenical, L. Minale, R. Riccio, Julian Battaile, Michael Kirkup, Richard E. MooreCite this: J. Org. Chem. 1979, 44, 12, 2044–2047Publication Date (Print):June 1, 1979Publication History Published online1 May 2002Published inissue 1 June 1979https://pubs.acs.org/doi/10.1021/jo01326a040https://doi.org/10.1021/jo01326a040research-articleACS...

Azumamide E, a cyclotetrapeptide isolated from the sponge Mycale izuensis, is most powerful carboxylic acid containing natural histone deacetylase (HDAC) inhibitor known to date. In this paper, we describe design and synthesis of two stereochemical variants product. These compounds have allowed us clarify influence side chain topology on HDAC-inhibitory activity. The present contribution also reveals identity recognition pattern between azumamides deacetylase-like protein (HDLP) model...

An inverse virtual screening in silico approach has been applied to natural bioactive molecules screen their efficacy against proteins involved cancer processes, with the aim of directing future experimental assays. Docking studies were performed on a panel 126 protein targets extracted from Protein Data Bank, analyze possible interactions small library 43 compounds. Analysis molecular docking results was through use tables containing energy data organized matrix. The application this may...

Swinhoeisterols A (1) and B (2), two novel sterols with an unprecedented 6/6/5/7 ring system, were isolated from the sponge Theonella swinhoei. The structures absolute configurations elucidated by spectroscopic analysis, X-ray single-crystal diffraction, modified Mosher's method, TDDFT/ECD calculations. cytotoxicity of these compounds toward A549 MG-63 cells encourages studies on their potential target using inverse virtual screening approach. predicted inhibitor h(p300) was corroborated in...