New Coumarinyl Ethers in <i>Daphne oleoides </i><scp>Schreb</scp>. Collected from Sardinia Island

Venditti, Alessandro; Sanna, Cinzia; Lorenzetti, Lorenzo M.; Ballero, Mauro; Bianco, Armandodoriano

doi:10.1002/cbdv.201700072

Cited by 19 publications

(9 citation statements)

References 46 publications

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“…The 1 H NMR chemical shifts of compound 3 are different from those obtained by Curini et al However, they are consistent with those obtained by Venditti et al and Gao et al The largest discrepancies were 0.04 and 0.06 ppm, respectively. Apparently, there are differences in the proton assignments regarding those reported by Curini et al, even so, the deviation is significant in the chemical shift of proton H5 (0.17 ppm).…”

Section: Methodssupporting

confidence: 80%

Solubility of Collinin and Isocollinin in Pressurized Carbon Dioxide: Synthesis, Solubility Parameters, and Equilibrium Measurements

et al. 2019

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Collinin is a derivative of coumarin that has shown remarkable potential against cancer, tuberculosis, periodontitis, and other prevalent diseases, and is usually extracted from plants of the Rutaceae family at a very low yield. In this work, collinin and a position-isomer herein called isocollinin were synthesized at different scales (from 1 to 50 g of precursor) by a route consisting of two parallel and two sequential chemical reactions. The isomers were characterized by 1H NMR, 13C NMR, nuclear Overhauser enhancement spectroscopy NMR, melting temperature, and melting enthalpy. For each isomer, the Hansen solubility parameters and the radius of its solubility sphere were experimentally determined by solubility tests in 15 common solvents and two solvent blends. The solubility of each isomer in pressurized CO2 was determined at 30 and 50 °C from 72.2 to 112.9 bar, by an in situ high-pressure spectrometry technique, which was validated with the anthracene–CO2 system. The solubility of both isomers in CO2 increased with pressure in the range of temperatures and pressures considered, but that of collinin exhibited an asymptotic behavior around 80.8 and 104.8 bar, at 30 and 50 °C, respectively.

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Section: Methodssupporting

confidence: 80%

Solubility of Collinin and Isocollinin in Pressurized Carbon Dioxide: Synthesis, Solubility Parameters, and Equilibrium Measurements

et al. 2019

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“…In fact, its occurrence has been reported only in D. acutiloba Rehder [ 37 ] and D. oleoides Schreb. [ 38 ]. Syringin ( 8 ) has been identified in D. oleoides Schreb.…”

Section: Resultsmentioning

confidence: 99%

“…Syringin ( 8 ) has been identified in D. oleoides Schreb. [ 15 , 38 ] but also in many other Daphne species like D. arisanensis Hayata [ 39 ], D. kiusiana var. atrocaulis (Rehder) F.Maek.…”

Section: Resultsmentioning

confidence: 99%

Phytochemical Analysis and Biological Activities of the Ethanolic Extract of Daphne sericea Vahl Flowering Aerial Parts Collected in Central Italy

et al. 2021

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In this paper, the first phytochemical analysis of the ethanolic extract of Daphne sericea Vahl flowering aerial parts collected in Italy and its biological activities were reported. Eleven compounds were identified i.e., α-linolenic acid (1), tri-linoleoyl-sn-glycerol (2), pheophorbide a ethyl ester (3), pilloin (4), sinensetin (5), yuanhuanin (6), rutamontine (7), syringin (8), p-coumaric acid (9), p-anisic acid (10) and caffeic acid (11). To the best of our knowledge, compounds (1-4, 7-8 and 10) were isolated from D. sericea for the first time during this work, whereas sinensetin (5) represents a newly identified component of the entire Thymelaeaceae family. The extract was found to possess radical scavenging against both DPPH• and 2,2′-azino-bis(3-thylbenzothiazoline-6-sulfonic acid (ABTS•+) radicals, with at least a 40-fold higher potency against the latter. Moreover, chelating abilities against both ferrous and ferric ions have been highlighted, thus suggesting a possible indirect antioxidant power of the extract. Although the precise bioactive compounds remain to be discovered, the polyphenolic constituents, including phenolic acids, tannins and flavonoids, seem to contribute to the antioxidant power of the phytocomplex. In addition, the extract produced cytotoxic effects in MDA-MB-231 and U87-MG cancer cell lines, especially at the concentration of 625 μg/mL and after 48–72 h. Further studies are required to clarify the contribution of the identified compounds in the bioactivities of the extract and to support possible future applications.

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“…The compounds obtained by repeated trapping of peak 20 showed a molecular ion with m/z 457.3672 [M + H] + suggesting the molecular formula C 30 H 48 O 3 (ΔM = 0.9 ppm). The 1 HNMR spectrum of 20 , showed signals characteristic of an ursan-12-oic acid, and comparison with NMR data from literature allowed identification of 20 as ursolic acid [ 36 ]. NMR data of 13 – 20 are given in Supplementary Material (Table S1) .…”

Section: Resultsmentioning

confidence: 99%

High-Resolution PTP1B Inhibition Profiling Combined with HPLC-HRMS-SPE-NMR for Identification of PTP1B Inhibitors from Miconia albicans

et al. 2018

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Protein tyrosine phosphatase 1B (PTP1B) is an intracellular enzyme responsible for deactivation of the insulin receptor, and consequently acts as a negative regulator of insulin signal transduction. In recent years, PTP1B has become an important target for controlling insulin resistance and type 2 diabetes. In the present study, the ethyl acetate extract of leaves of Miconia albicans (IC50 = 4.92 µg/mL) was assessed by high-resolution PTP1B inhibition profiling combined with HPLC-HRMS-SPE-NMR for identification of antidiabetic compounds. This disclosed eleven PTP1B inhibitors, including five polyphenolics: 1-O-(E)-caffeoyl-4,6-di-O-galloyl-β-d-glucopyranose (2), myricetin 3-O-α-l-rhamnopyranoside (3), quercetin 3-O-(2″-galloyl)-α-l-rhamnopyranoside (5), mearnsetin 3-O-α-l-rhamnopyranoside (6), and kaempferol 3-O-α-l-arabinopyranoside (8) as well as eight triterpenoids: maslinic acid (13), 3-epi-sumaresinolic acid (14), sumaresinolic acid (15), 3-O-cis-p-coumaroyl maslinic acid (16), 3-O-trans-p-coumaroyl maslinic acid (17), 3-O-trans-p-coumaroyl 2α-hydroxydulcioic acid (18), oleanolic acid (19), and ursolic acid (20). These results support the use of M. albicans as a traditional medicine with antidiabetic properties and its potential as a source of PTP1B inhibitors.

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New Coumarinyl Ethers in Daphne oleoides Schreb. Collected from Sardinia Island

Cited by 19 publications

References 46 publications

Solubility of Collinin and Isocollinin in Pressurized Carbon Dioxide: Synthesis, Solubility Parameters, and Equilibrium Measurements

Solubility of Collinin and Isocollinin in Pressurized Carbon Dioxide: Synthesis, Solubility Parameters, and Equilibrium Measurements

Phytochemical Analysis and Biological Activities of the Ethanolic Extract of Daphne sericea Vahl Flowering Aerial Parts Collected in Central Italy

High-Resolution PTP1B Inhibition Profiling Combined with HPLC-HRMS-SPE-NMR for Identification of PTP1B Inhibitors from Miconia albicans

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