Psathrosterols C-E, highly conjugated ergosterol derivatives from Psathyrella rogueiana with anti-inflammatory and immunosuppressive activity.

Three new ergosterols featuring with a highly conjugated ring system, psathrosterols C-E (1-3), have been isolated from the fungus Psathyrella rogueiana. The structures with the absolute configurations were elucidated by means of spectroscopic methods and single crystal X-ray diffraction. Compounds 1-3 exhibit inhibitory activity against NO production with IC50 values ranging from 8.4 to 21.8 µM. Compound 1 inhibits the LPS-induced proliferation of B lymphocyte cells with an IC50 value of 12.3 µM.

Structurally diverse diterpenoids and phenanthrene derivatives from the roots of Baliospermumsolanifolium.

Ten undescribed diterpenoids (1-10) and three undescribed phenanthrene derivatives (11-13), together with seven known compounds, were isolated from the roots of Baliospermum solanifolium. Their structures were determined by a combination of spectroscopic data analysis, electronic circular dichroism calculations and single-crystal X-ray diffraction studies. Compounds 1-7 (baliosperoids A-G) represent the examples of 20-nor-ent-podocarpane class first discovered in nature. In particular, compound 7 possesses a unique 2,3-seco ring system incorporating γ-butanolide moiety. All isolates were assessed for their cytotoxic activities against HT-29, HCT-116, HCT-15, MCF-7, and A549 cell lines as well as their inhibitory effects on lipopolysaccharide-induced NO production in RAW264.7 cells. Compound 1, a 20-nor-ent-podocarpane-type diterpenoid possessing a Δ1,2 double bond, not only exhibited considerable proliferation inhibition against five human cancer cell lines, with IC50 values ranging from 4.13 to 23.45 µM, but also displayed the most potent inhibitory activity on NO production with IC50 value at the nanomolar level (0.63 ± 0.21 µM).

Sesquiterpenoids and steroids from Eupatorium fortunei and their inhibitory effects on NO production.

Two heterodimers including a clovane-phenylpropanoid hybrid (1) and a clovane-menthane hybrid (2), five linear sesquiterpenoids incorporating a tetrahydrofuran ring (3-6 & 8), and four steroids (7 & 9-11), were separated from the ethanolic extract of a well-known aromatic and medicinal herb Eupatorium fortunei. Their structures were characterised by detailed analyses of spectroscopic data and comparison with known analogues, with seven (1-7) of them being described for the first time. The hybrids 1 and 2 represent the first examples of clovane type sesquiterpenoids hybridising with other class of natural products, and compounds 3-6 and 8 are first linear sesquiterpenyl constituents reported from the title species. All the isolates were evaluated for their inhibitory effect on the NO production induced by LPS in murine RAW264.7 macrophage cells, and 1, 7, 10 and 11 exhibited moderate activity with IC50 values in the range of 24.4-43.5 µM.

Ganonorsterone A, a norsteroid from the medicinal fungus Ganoderma lingzhi.

Phytochemical investigation on the fruiting bodies of the medicinal fungus Ganoderma lingzhi led to the isolation of a new norsteroid, namely ganonorsterone A (1), together with one known steroid, cyathisterol (2). The structure and absolute configuration of compound 1 were assigned by extensive analysis of MS, NMR data, and quantum-chemical calculations including electronic circular dichroism (ECD) and calculated 13C NMR-DP4+ analysis. Bioassay results showed that compound 1 displayed moderate inhibition on NO production in RAW 264.7 macrophages.

Identification and nitric oxide production inhibitory activity of phenolic derivatives from the trunks of Gnetum latifolium.

Phytochemical investigation of the trunks from Gnetum latifolium led to the isolation of a novel phenolic glucoside, 2E-2,4-di-(3,4-dihydroxyphenyl)but-2-en-1-yl-O-ß-D-glucopyranoside (1), along with five known stilbene derivatives (2-6). Their structures were determined mainly using high-resolution electrospray ionisation mass spectrometry and nuclear magnetic resonance spectroscopic analyses, followed by comparisons of observed spectral data with reported values. The novel compound 1 in G. latifolium was found to be useful as a chemotaxonomic marker. Biological evaluation revealed that compound 6 had remarkable inhibitory effects on nitric oxide production, with a half-maximal inhibitory concentration (IC50) value of 4.85 ± 0.20 µM, which was much higher than that of the positive control dexamethasone (IC50 = 14.20 ± 0.54 µM).

Two highly conjugated ergosterols from the fungus Psathyrella rogueiana and their anti-inflammatory activity.

Two previously undescribed ergosterols containing a highly conjugated ring system, psathrosterols A and B (1 and 2), have been isolated from the fungus Psathyrella rogueiana. Their structures with absolute configurations were established by extensive spectroscopic methods, as well as single crystal X-ray diffraction. Compounds 1 and 2 showed inhibitory activity against NO production with IC50 values of 22.3 and 16.4 µM, respectively.

Nitrogenous compounds from Aesculus wilsonii seeds.

Eight nitrogenous compounds including five undescribed ones, aeswilnitrousol A (1), aeswilnitrousosides BD (2-4), and 6-(2-hydroxy-3-methylbutylamino)-8-oxoadenine (5) were isolated from the seeds of Aesculus wilsonii. Their structures and absolute configurations were established based on spectroscopic determination, calculated electronic circular dichroism (ECD) analysis, as well as chemical reaction methods. Among the three known compounds, 7 and 8 were obtained from the Aesculus genus for the first time, and 6 was gained from this plant initially. The 13C NMR data of 7 and 8 were reported for the first time. Moreover, the inhibitory effect of all the isolates against LPS-induced nitric oxide production in RAW264.7 macrophages was evaluated. As a result, compounds 2 and 8 exhibited anti-inflammatory activity in a concentration-dependent manner at 10, 25, and 50 µM.

Aromatic compounds from the seeds of Dolichos lablab L. with anti-inflammatory activity.

Twenty-four aromatic compounds including five novel ones, dolilabphenosides A (1), B1 (2), B2 (3), C1 (4), and C2 (5) were obtained from the seeds of Dolichos lablab L. Their structures were established based on spectroscopic analyses and chemical reactions. Among the known compounds, 9, 10, 14, 17, 19, and 22-24 were gained from the family Leguminosae for the first time, and 6, 8, 11-13, 15, 16, 18, 20, as well as 21 were firstly identified from Dolichos genus. Moreover, the inhibitory effect evaluation of all the isolates against LPS-induced nitric oxide (NO) production in RAW264.7 macrophages suggested that compounds 1-3, 6, 7, 11-15, 17, 20, 21, 23, 24 exhibited anti-inflammatory activity in a concentration-dependent manner. Moreover, the novel compounds, dolilabphenosides A (1), B1 (2), B2 (3) were found to inhibit the secretion of inflammatory cytokine IL-1ß.

Boerechalasins A-G, cytochalasans from the fungus Boeremia exigua with anti-inflammatory and cytotoxic activities.

Seven previously undescribed cytochalasans, namely, boerechalasins A-G, together with one analogue, were characterized from the solid culture of the fungus Boeremia exigua. Their structures and absolute configurations were elucidated on the basis of extensive spectroscopic analysis as well as electronic circular dichroism calculations. Remarkably, boerechalasin F possessed an unusual sulfoxide moiety that might be derived from methionine, while boerechalasin G had an unusual 5-methylcyclohexane-1,2,3-triol substituent at N-2 position. Boerechalasins A and E exhibited inhibitory activities against nitric oxide production in LPS-induced RAW264.7 macrophages with IC50 values of 21.9 and 5.7 µM, respectively. Boerechalasin F displayed cytotoxicity against human MCF‒7 cells with an IC50 value of 22.8 µM.

Lanostane triterpenoids with anti-proliferative and anti-inflammatory activities from medicinal mushroom Ganoderma lingzhi.

Eight previously undescribed lanostane triterpenoids and nine known ones were identified from the fruiting bodies of Ganoderma lingzhi S.H. Wu, Y. Cao & Y.C. Dai. Their structures were determined based on spectroscopic data and quantum chemical calculations. Structurally, ganoderane GL-1, featuring a hydrogenated tetramethyls-phenanthraquinone, represents the first example in lanostane nor-triterpenoid group. Biologically, ganoderanes GL-2 and GL-3, distinguished by the presence of a rare "1,11-epoxy" moiety, exhibited significant inhibition against nitric oxide production induced by lipopolysaccharide in RAW264.7 macrophage cells, while ganoderanes GL-4 and GL-8 exhibited bifunctional activities of anti-proliferation and anti-inflammation.

New Phenolic Dimers from Plant Paeonia suffruticosa and Their Cytotoxicity and NO Production Inhibition.

The Paeonia suffruticosa, known as 'Feng Dan', has been used for thousands of years in traditional Chinese medicine. In our chemical investigation on the root bark of the plant, five new phenolic dimers, namely, paeobenzofuranones A-E (1-5), were characterized. Their structures were determined using spectroscopic analysis including 1D and 2D NMR, HRESIMS, UV, and IR, as well as ECD calculations. Compounds 2, 4, and 5 showed cytotoxicity against three human cancer cell lines, with IC50 values ranging from 6.7 to 25.1 µM. Compounds 1 and 2 showed certain inhibitory activity on NO production. To the best of our knowledge, the benzofuranone dimers and their cytotoxicity of P. suffruticosa are reported for the first time in this paper.

Cytochalasans from the Endophytic Fungus Aspergillus sp. LE2: Their Structures, Antibacterial and NO Production Inhibitory Activities.

Six new cytochalasans-namely, aspergicytochalasins A-F (1-6)-together with five known analogs were isolated and characterized from the endophytic fungus Aspergillus sp. from the medicinal plant Lonicera japonica. The structures of the new compounds were established by NMR and MS methods as well as single crystal X-ray diffractions. Compounds 3 and 4 showed weak antibacterial activities to Staphylococcus aureus, with MIC values of 128 and 64 µg/mL, respectively. Compounds 1, 3, 5 and 6 showed inhibitory activities on NO production, with IC50 values less than 40 µM.

Phytochemical Characterization and In Vitro Anti-Inflammatory Evaluation in RAW 264.7 Cells of Jatropha cordata Bark Extracts.

The inflammatory process, although beneficial, can produce tissue damage and systemic damage when uncontrolled. Effective therapeutic alternatives with little or no side effects are of great therapeutic interest. This study aimed to determine the phytochemical composition of bark extracts from J. cordata, an endemic plant from México, and evaluate their in vitro anti-inflammatory activity. Hexane, ethyl acetate, and methanol extracts were characterized by qualitative phytochemical tests, and their bioactive groups were identified by 1H NMR and gas chromatography coupled to mass spectrometry (GC-MS). The extract's anti-inflammatory activity was evaluated as nitric oxide (NO) production and their cytotoxicity by an MTS cell proliferation assay in lipopolysaccharide (LPS)-activated RAW 264.7 cells at concentrations of 1-100 µg/mL. The hexane extract contained fatty acids, fatty esters, phytosterols, alkanes, vitamin E, and terpenoids; the ethyl acetate extract showed fatty acids, fatty esters, aromatic aldehyde, phytosterols, vitamin E, and terpenoids, while the methanolic extract showed fatty esters, fatty acid, aromatics aldehydes, and alcohol. The ethyl acetate extract showed the highest inhibition of NO production, followed by the methanolic extract and the hexane extract, without affecting the viability of RAW 264.7 macrophage cells. The results suggest that J. cordata extracts are a potential source of bioactive compounds with anti-inflammatory potential.

Lanostane triterpenoids from the fungus Physisporinus vitreus and their inhibitory activity against nitric oxide production.

Eight undescribed lanostane triterpenoids, physivitrins A-H, along with four known analogues, were isolated from cultures of the fungus Physisporinus vitreus. Their structures were elucidated on the basis of extensive spectroscopic methods, in which the absolute configuration of physivitrin A was elucidated using electronic circular dichroism calculation and nuclear magnetic resonance (NMR) calculation with DP4+ analysis. Physivitrins B and C showed inhibitory activities against nitric oxide (NO) production in LPS-activated RAW264.7 macrophages with IC50 values of 7.5 and 23.5 µM, respectively. Meanwhile, proinflammatory cytokines (TNF-α, iNOS and IL-1ß) mRNA expression was also inhibited by physivitrin B significantly.

Tricholosterols A-D, four new ergosterol derivatives from the mushroom Tricholoma terreum.

Four ergosterol derivatives, named tricholosterols A-D (1-4), have been isolated from the fruiting bodies of Tricholoma terreum. Their chemical structures have been determined using a combination of spectroscopic analysis as well as computational methods. Compound 1 possesses a rare D-ring opening ergosterol skeleton, while compounds 2-4 are rare degraded ergosterols. Compounds 1 and 4 exhibited moderate inhibitory activity against NO production with IC50 values of 27.6 and 31.8 µM, respectively. This is the first report of steroids from T. terreum.

Unusual ring B-seco isosteroidal alkaloid, yibeiglycoalkaloids A-E from Fritillaria pallidiflora schrenk.

Five previously undescribed steroidal glycoalkaloids(SGAs)and a rare ring B-seco isosteroidal alkaloid, were isolated from Fritillaria pallidiflora Schrenk, along with six known alkaloids. The structures of these alkaloids were established by comprehensive analyses of the 1D, 2D-NMR and HR-ESI-MS data. Configurations of sugar moieties were resolved by chemical derivations. The isolated compounds showed nitric oxide (NO) inhibitory activities in lipopolysaccharide (LPS) induced RAW264.7 cells, and yibeinone exhibited the strongest inhibitory effects among them. This study revealed that the alkaloids from F. pallidiflora might have significant anti-inflammatory potentials.

New Benzil and Isoflavone Derivatives with Cytotoxic and NO Production Inhibitory Activities from Placolobium vietnamense.

The phytochemical investigation of Placolobium vietnamense stems led to the isolation of a new isoflavone derivative (1) and three new benzil derivatives (2-4), together with four known pyranoisoflavones (5-8). The structures of all isolated compounds were determined on the basis of extensive spectroscopic analyses, including NMR and HRMS spectral data, as well as comparison of their spectroscopic data with those reported in the literature. The cytotoxicity of all isolated compounds was assessed against the human liver hepatocellular carcinoma (Hep G2) cell line, and compound 1 displayed the most significant cytotoxicity with an IC50 value of 8.0 µM. Furthermore, all isolated compounds were also tested for their inhibitory activity against NO production in RAW 264.7 macrophages. Of these, compound 1 exhibited the strongest inhibitory efficacy against the LPS-induced NO production with the IC50 value of 13.7 µM.

Four New Highly Oxygenated Eremophilane Sesquiterpenes from an Endophytic Fungus Boeremia exigua Isolated from Fritillaria hupehensis.

Four new eremophilane-type sesquiterpenes, boeremialanes A-D (1-4) were obtained from solid substrate cultures of Boeremia exigua (Didymellaceae), an endophytic fungus isolated from Fritillaria hupehensis (Liliaceae). Boeremialanes A-C (1-3) are highly oxygenated eremophilanes with a benzoate unit attached at the C-13 position and are rarely found in nature. Their structures and absolute configurations were determined by extensive spectroscopic methods, electronic circular dichroism (ECD), and nuclear magnetic resonance (NMR) calculations with DP4+ analysis. Boeremialane D (4) potently inhibited nitric oxide production in lipopolysaccharide-treated RAW264.7 macrophages with an IC50 of 8.62 µM and was more potent than the positive control, pyrrolidinedithiocarbamate (IC50 = 23.1 µM).

Structure elucidation of linear triquinane sesquiterpenoids, hirsutuminoids A-Q, from the fungus Stereum hirsutum and their activities.

Eighteen linear triquinane sesquiterpenoids (LTSs), including seventeen previously undescribed ones (hirsutuminoids A-Q), were isolated from the fermentation of the fungus Stereum hirsutum (Willd.) Pers. The structures and absolute configurations of the isolates were characterized by extensive spectroscopic analysis (1D, 2D NMR, and HRMS data), together with comparing the experimental and calculated data of both electronic circular dichroism and NMR data, as well as X-ray crystallography. Based on the literature survey and efforts on constructing the absolute configurations of these LTSs in this study, one empirical rule about the orientations of substitutions at C-2/C-3/C-7/C-9 was summarized. Anti-inflammatory and cytotoxic bioassays showed that only hirsutuminoid B inhibited the nitric oxide (NO) production in RAW 264.7 macrophages with an IC50 value, 18.9 µM.

Polyhydroxylated eudesmane sesquiterpenoids and sesquiterpenoid glucoside from the flower buds of Tussilago farfara.

Chemical fractionation of the n-BuOH partition, which was generated from the EtOH extract of the flower buds of Tussilago farfara, afforded a series of polar constituents including four new sesquiterpenoids (1-4), one new sesquiterpenoid glucoside (5) and one known analogue (6) of the eudesmane type, as well as five known quinic acid derivatives (7-11). Structures of the new compounds were unambiguously characterized by detailed spectroscopic analyses, with their absolute configurations being established by X-ray crystallography, electronic circular dichroism (ECD) calculation and induced ECD experiments. The inhibitory effect of all the isolates against LPS-induced NO production in murine RAW264.7 macrophages was evaluated, with isochlorogenic acid A (7) showing significant inhibitory activity.