Search results for "010404 medicinal & biomolecular chemistry"
showing 10 items of 373 documents
Cytotoxic eudesmane sesquiterpenes from Crepis sancta
2019
Abstract Chemical exploration of Crepis sancta (L.) Bornm. (Asteraceae) aerial parts afforded two new eudesmane sesquiterpenes (1 and 2) together with three known congeners (3-5) and two known methylated flavonoids (6 and 7). Structure elucidation of the new compounds was unambiguously performed based on HRESIMS, 1D and 2D NMR spectroscopic analyses. All isolated compounds were subjected to an in vitro cytotoxicity assay against mouse lymphoma (L5178Y) cells, revealing moderate activities with IC50 ranging from 7.9 to 21.0 μM.
Chemical constituents from Phlomis bovei Noë and their chemotaxonomic significance
2020
Abstract A phytochemical investigation of the leaves and roots of Phlomis bovei Noe (Lamiaceae) led to the isolation of sixteen compounds, including iridoids (1, 2, 3), megastigmanes (4, 5), phenylpropanoids (6, 7, 8, 9, 10), lignans (11, 12, 13, 14), a nortriterpene (15), and a phenyl glucoside (16). Compounds (1, 2, 4, 5, 6, 10) were obtained from the leaves and compounds (1, 2, 3, 7, 8, 9, 11, 12, 13, 14, 15, 16) were isolated from the roots. Compounds 1 and 2 were found both in the leaves and in roots. The compounds were identified by analysis of 1D- (1H, 13C), 2D-NMR (1H–1H COSY, TOCSY, ROESY, HSQC, HMBC) spectroscopic data, mass spectrometry (ESI- and HR-ESI-MS), and by comparison wit…
Chemical constituents from Anthocleista liebrechtsiana De Wild & T. Durand (Loganiaceae)
2018
Abstract A new steroid derivative, (24S)-3β-hydroxy-7β-methoxyergost-5-ene (1), was isolated along with eleven known compounds: 7α-hydroxysterol (2), β-sitosterol (3), oleanolic acid (4), betulinic acid (5), lupeol (6), swertiaperennin (7), decussatin (8), tetracosanoic acid (9) β-sitosterol-3-O-β- d -glucopyranoside (10), (2R,3S)-2,3-dihydro-2-(3,4-dimethoxyphenyl)-3-hydroxymethyl-5-(2-formylvinyl)-7-hydroxybenzofuran (11) and acacetin 6-C-β- d -glucopyranoside (12) from the tree bark and leaves of Anthocleista liebrechtsiana De Wild & T. Durand. Their structures were elucidated on the basis of spectroscopic (1D and 2D NMR) and mass spectrometric data. Compounds 2 and 7–10 have already bee…
Hydroquinone derivatives from the marine-derived fungus Gliomastix sp.
2017
Eight new hydroquinone derivatives, gliomastins A–D (1–4), 9-O-methylgliomastin C (5), acremonin A 1-O-β-D-glucopyranoside (6), gliomastin E 1-O-β-D-glucopyranoside (7), and 6′-O-acetyl-isohomoarbutin (8), together with seven known analogues were isolated from the marine-derived fungus Gliomastix sp. Their structures were elucidated by extensive spectroscopic analysis including 1D and 2D NMR measurements aided by DFT NMR calculations as well as MS data. TDDFT-ECD and OR calculations were performed to determine the absolute configurations of 1 and the aglycones of 6 and 7. Compound 1 features a novel skeleton, biogenetically derived from a Diels–Alder reaction between derivatives of 11 and 1…
Phytochemical Profile and Antioxidant Activity of the Aerial Part Extracts from Matthiola incana subsp. rupestris and subsp . pulchella ( Brassicacea…
2021
As part of a project aimed at investigating the Matthiola taxa endemic to Sicily (Italy), this study focused on Matthiola incana, an edible species used in the traditional medicine of various countries. Herein, the characterization of phenolic and volatile compounds, the antioxidant capacity in vitro (1,1-diphenyl-2-picrylhydrazil (DPPH), reducing power and Fe2+ chelating activity assays) and the toxicity test (Artemia salina lethality bioassay) of the hydroalcoholic extracts from the aerial parts of M. incana subsp. rupestris from Mt. Pellegrino (Palermo) and Mt. Erice (Trapani), and of M. incana subsp. pulchella are reported. The results are compared with those previously shown for M. inc…
New antimicrobial metabolites from the medicinal herb Artemisia herba-Alba
2019
Artemisia herba-alba is widely used in traditional medicines for the treatment of several diseases. From the aerial parts organic extract of A. herba-alba, two new compounds, 1,3,8-trihydroxyeudesm-4-en-7α,11βH-12,6α-olide (1) and 5-β-D-glucopyranosyloxy-7-methoxy-6H-benzopyran-2-one (2), respectively, together with five known metabolites: 3α,8β-dihydroxygermacr-4(15),9(10)-dien-7β,11αH,12,6α-olide (3), 1β,8α-dihydroxy-11α,13-dihydrobalchanin (4), 11-epiartapshin (5), tomenin (6) and benzoic acid, p-(β-D-glucopyranosyloxy)-methyl ester (7), were isolated and identified. The chemical structures were proven depending upon spectroscopic analysis, including 1 D/2D NMR as and ESI-MS…
Neo-clerodane diterpenoids from Conyza pyrrhopappa Sch.Bip. ex A.Rich
2019
Two hitherto unknown neo-clerodane-type diterpenoids along with twelve known compounds have been isolated from Conyza pyrrhopappa Sch.Bip. ex A.Rich, a medicinal plant traditionally used across tropical Africa to relieve fever. The structures of isolates have been elucidated by a combination of spectroscopic techniques. The crude extract and the isolated compounds were evaluated in the Hela-S3 cell line and in a panel of microorganisms (bacteria and fungi) at concentrations up to 50 µg/mL. The new compounds were inactive while the pentamethylated flavonoids showed low to significant activity against the cancer cell line used. However, none of the samples showed any activity against the test…
Cytotoxic alkaloids from the root of Zanthoxylum paracanthum (mildbr) Kokwaro
2021
Chemical investigation of the root of Zanthoxylum paracanthum afforded 1 new alkamide derivative, (2E,4E)-6-oxo-N-isobutyldeca-2,4-dienamide (1) together with 10 known congeners including one pheno...
Four new triterpene saponins from Bupleurum rigidum L.
2018
Abstract Four previously undescribed triterpene saponins (1-4) were isolated from the EtOH/H2O extract of the aerial parts of Bupleurum rigidum, together with a known structural analogue. Their structures were elucidated by analysis of 1D-(1H, 13C) and 2D-NMR (1H-1H COSY, TOCSY, ROESY, HSQC, HMBC) spectroscopic data and mass spectrometry (ESI- and HR-ESI-MS) and by comparison with those of related metabolites. An unusual structure was characterized as 3-O-β-D-glucopyranosyl-(1 → 2)-[ β-D-glucopyranosyl-(1 → 3)]- β-D-fucopyranosyl-21-O-β-D-glucoyranosyl-3β,16β,21β,23-tetrahydroxy-13,28-epoxyolean-11-ene (1). The three other compounds shared the same sugar sequence as 1 and differed by the st…
How To Design Selective Ligands for Highly Conserved Binding Sites: A Case Study Using N-Myristoyltransferases as a Model System
2019
A model system of two related enzymes with conserved binding sites, namely N-myristoyltransferase from two different organisms, was studied to decipher the driving forces that lead to selective inhibition in such cases. Using a combination of computational and experimental tools, two different selectivity-determining features were identified. For some ligands, a change in side-chain flexibility appears to be responsible for selective inhibition. Remarkably, this was observed for residues orienting their side chains away from the ligands. For other ligands, selectivity is caused by interfering with a water molecule that binds more strongly to the off-target than to the target. On the basis o…