Constituents of <i>Cydonia vulgaris</i>: Isolation and Structure Elucidation of Four New Flavonol Glycosides and Nine New α-Ionol-Derived Glycosides

In a previous paper, we described the isolation of four new sesterterpenes from Cydonia vulgaris Pers. Here we report the isolation of four new flavonol glycosides (1−4) and nine new α-ionol-derived glycosides (5−13) together with the known 3-oxo-α-ionol 9-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (14), vomifoliol 9-O-β-d-glucopyranoside (roseoside) (15), and vomifoliol 9-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (16) from the MeOH extract of the aerial parts of C. vulgaris Pers. (Rosaceae). All structures were elucidated by spectroscopic methods, including the concerted application of one-dimensional NMR and two-dimensional NMR techniques (COSY-90 and HETCOR). Keywords: Cydonia vulgaris; Rosaceae; flavonol glycosides; α-ionol glycosides; 1H and 13C NMR (one- and two-dimensional

Data_Sheet_1_Corylus avellana: A Source of Diarylheptanoids With α-Glucosidase Inhibitory Activity Evaluated by in vitro and in silico Studies.docx

Corylus avellana hard shells, green leafy involucres, leaves, and male flowers have shown to be a source of diarylheptanoids, a class of natural products with promising biological activities. Cyclic diarylheptanoids, named giffonins, were isolated from the Italian cultivar “Tonda di Giffoni.” Even if many efforts have been made to establish the chemistry of these compounds, little is known about their biological properties. Herein, the inhibitory effects of diarylheptanoids isolated from C. avellana byproducts against α-glucosidase enzyme were evaluated. Molecular docking experiments disclosed the establishment of several key interactions between all the screened diarylheptanoids and the protein counterpart, whose model was built through homology modeling procedure, thus rationalizing the detected inhibitory activities. Specifically, the most active compounds giffonin J (10), K (11), and P (16) were able to make both H-bonds and π–π stacking contacts with different residues belonging to the binding site responsible for the catalytic activity of the investigated enzyme. To highlight the occurrence of the bioactive diarylheptanoids in the extracts of C. avellana byproducts obtained by eco-friendly extractions, their LC-MS profiles were analyzed. LC-MS analysis showed how giffonin J (10), K (11), and P (16) occurred in the ethanol extract of the leaves, while in the extracts of shells and green leafy involucres only giffonin P (16) was evident. Moreover, the quantitative analysis of giffonin J (10), K (11), and P (16) in C. avellana byproducts was carried out by an analytical approach based on LC–ESI/QTrap/MS, using the Multiple Reaction Monitoring (MRM) experiment. These results prompt to evaluate C. avellana byproducts, especially the leaves, as a prospective source of bioactive diarylheptanoids for the development of functional ingredients for the treatment of diabetes.</p

Giffonins A–I, Antioxidant Cyclized Diarylheptanoids from the Leaves of the Hazelnut Tree (<i>Corylus avellana</i>), Source of the Italian PGI Product “Nocciola di Giffoni”

Eight new diaryl ether heptanoids, giffonins A–H (<b>1</b>–<b>8</b>), and one diaryl heptanoid, giffonin I (<b>9</b>), were isolated from the methanol extract of the leaves of <i>Corylus avellana</i>. Its hazelnut is the PGI product of the Campania region (Italy) known as “Nocciola di Giffoni”. The MeOH extract of <i>C. avellana</i> leaves and giffonins A–I (<b>1</b>–<b>9</b>) were evaluated for their inhibitory effects on human plasma lipid peroxidation induced by H₂O₂ and H₂O₂/Fe²⁺, by measuring the concentration of TBARS (thiobarbituric acid reactive substances). Compounds <b>4</b> and <b>8</b> at 10 μM reduced both H₂O₂- and H₂O₂/Fe²⁺-induced lipid peroxidation by more than 60% and 50%, respectively, indicating higher activity than curcumin used as reference compound

New Triterpene Glycosides from the Stems of <i>Anomospermum </i><i>g</i><i>randifolium</i>

Two new dammarane saponins identified as jujubogenin 3-O-α-l-arabinofuranosyl(1→2)-[β-d-glucopyranosyl(1→6) β-d-glucopyranosyl(1→3)]-α-l-arabinopyranoside (2) and jujubogenin 3-O-α-l-arabinofuranosyl(1→2)-{6-O-[3-hydroxy-3-methylglutaryl]-β-d-glucopyranosyl(1→3)}-α-l-arabinopyranoside (3) and a new lupane saponin, 3β-hydroxylup-20(29)-en-27,28-dioic acid 28-O-β-d-glucopyranosyl(1→2)-[β-d-xylopyranosyl(1→3)]-β-d-xylopyranosyl(1→2)-β-d-glucopyranoside ester (5), along with the known jujubogenin 3-O-α-l-arabinofuranosyl(1→2)-[β-d-glucopyranosyl(1→3)]-α-l-arabinopyranoside (1) and 3β-hydroxylup-20(29)-ene-27,28-dioic acid (4), were isolated from the methanol extract of the stems of Anomospermum grandifolium. The structures of the new compounds were established by spectral analysis. Antimicrobial activity screening of compounds 1−3 revealed antifungal properties against C. albicans ATCC 3153 for compounds 2 and 3. The antibacterial and antifungal activities of the petroleum ether, chloroform, and methanol extracts of A. grandifolium stems were also evaluated

Three new triterpene saponins from roots of <i>Eryngium planum</i>

<div><p>Saponin composition of the roots of <i>Eryngium planum</i> L. was investigated. Triterpene saponins found in <i>E. planum</i> and also present in <i>Eryngium maritimum</i> were different from those described previously in <i>Eryngium campestre</i> L. Three primary saponins were isolated and their tentative identifications, based on the electrospray MS/MS fragmentation patterns, were subsequently confirmed by 1D and 2D NMR analyses. Their structures were established as 3-<i>O</i>-β-d-glucopyranosyl-(1 → 2)-β-d-glucuronopyranosyl-21-<i>O</i>-acetyl-22-<i>O</i>-angeloyl-R1-barrigenol (<b>1</b>) and 3-<i>O</i>-β-d-glucopyranosyl-(1 → 2)-β-d-glucuronopyranosyl-22-<i>O</i>-angeloyl-A1-barrigenol (<b>2</b>) and 3-<i>O</i>-β-d-glucopyranosyl-(1 → 2)-β-d-glucuronopyranosyl-22-<i>O</i>-angeloyl-R1-barrigenol (<b>3</b>). Concentrations of the newly identified compounds in aerial parts and roots of both species were estimated using the liquid chromatography–mass spectrometry method.</p></div

Anti-inflammatory Activity of Tanshinone-Related Diterpenes from <i>Perovskia artemisioides</i> Roots

Perovskia artemisioides is a perennial and aromatic plant widely distributed in the Baluchestan region of Iran. Phytochemical analysis of a n-hexane extract of P. artemisioides roots, guided by an analytical approach based on LC-ESI/LTQOrbitrap/MS/MS, yielded six previously undescribed diterpenoid compounds (2, 9–11, 16, and 20), and 19 known diterpenoids, for which the structures were elucidated by 1D and 2D NMR experiments. Some of the isolated compounds showed significant anti-inflammatory activity using J774A.1 macrophage cells stimulated with Escherichia coli lipopolysaccharide. In particular, compounds 6, 8, 17, 18, 20, and 22 significantly inhibited the release of nitric oxide and the expression of related pro-inflammatory enzymes, such as inducible nitric oxide synthase and cycloxygenase-2. Moreover, two compounds that showed the highest activity in reducing nitric oxide release (6 and 18) were tested to evaluate their effects on nitrotyrosine formation and reactive oxygen species release. Both compounds inhibited ROS release and, in particular, compound 6 also inhibited nitrotyrosine formation at all tested concentrations, thus indicating a significant antioxidant potential

Naphthopyranone Glycosides from <i>Paepalanthus </i><i>m</i><i>icrophyllus</i>

Three new naphthopyranone glycosides, paepalantine-9-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (1), paepalantine-9-O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranoside (2), and paepalantine-9-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (3), along with the known paepalantine-9-O-β-d-glucopyranoside (4) were isolated from aerial parts of Paepalanthus microphyllus. These compounds were characterized by spectrometric methods, including electrospray mass spectrometry and 1D and 2D NMR experiments. As a part of our program for screening natural compounds for anti-HIV activity, compounds 1−4 were tested in C8166 cells infected with HIV-1MN

Planifolin, a New Naphthopyranone Dimer and Flavonoids from <i>Paepalanthus </i><i>p</i><i>lanifolius</i>

A new naphthopyranone dimer (1) named planifolin was isolated from a methylene chloride extract of the capitula of Paepalanthus planifolius. The structure of 1 has been determined by chemical and spectroscopic means. In addition, a known dihydronaphthopyranone glycoside and seven known flavonoids were isolated from an ethanolic extract of the leaves of P. planifolius

Chemical constituents of <i>Silene montbretiana</i>

<p>A new steroidal glycoside, 3-<i>O</i>-β-d-glucopyranosyl-3β,25-dihydroxy-5β-cholest-7-en-6-one 25-<i>O</i>-β-d-glucopyranoside (<b>1</b>), together with six known steroidal derivatives (<b>2</b>-<b>7</b>), one cerebroside (<b>8</b>) and one flavonoid (<b>9</b>) were isolated from <i>Silene montbretiana</i> Boiss (Caryophyllaceae), a perennial herb growing mainly in the Middle and East Anatolia, Azerbaijan, Iran, and Turkey. Their structures were established by the extensive use of 1D and 2D NMR experiments along with ESI-MS analyses. The cytotoxicity against the cancer A549 (human alveolar basal carcinoma) and Hela (human epitheloid cervix carcinoma) cell lines has been evaluated. None of the tested compounds, in a range of concentrations between 12.5 and 100 μM, caused a significant reduction of the cell number.</p

Determination of volatile organic compounds in the dried leaves of <i>Salvia</i> species by solid-phase microextraction coupled to gas chromatography mass spectrometry

<p><i>Salvia</i> spp. are used throughout the world both for food and pharmaceutical purposes. In this study, a method involving headspace solid-phase microextraction combined with gas chromatography–mass spectrometry was developed, to establish the volatiles profile of dried leaves of four Iranian <i>Salvia</i> spp.: <i>Salvia officinalis</i> L., <i>Salvia leriifolia</i> Benth, <i>Salvia macrosiphon</i> Boiss. and two ecotypes of <i>Salvia reuterana</i> Boiss. A total of 95 volatiles were identified from the dried leaves of the five selected samples. Specifically, α-thujone was the main component of <i>S. officinalis</i> L. and <i>S</i>. <i>macrosiphon</i> Boiss. (34.40 and 17.84%, respectively) dried leaves, <i>S</i>. <i>leriifolia</i> Benth was dominated by β-pinene (27.03%), whereas α-terpinene was the major constituent of the two ecotypes of <i>S</i>. <i>reuterana</i> Boiss. (21.67 and 13.84%, respectively). These results suggested that the proposed method can be considered as a reliable technique for isolating volatiles from aromatic plants, and for plant differentiation based on the volatile metabolomic profile.</p