Ultrasound-assisted extraction optimization of polyphenols from Boletus bicolor and evaluation of its antioxidant activity.

Introduction: Boletus bicolor (B. bicolor) mushrooms are widely consumed as a valuable medicinal and dietary ingredient in China, but the active ingredients of this mushroom and their extraction methods were not extensively studied. Methods: In this paper, we propose an optimized ultrasound-assisted extraction (UAE) method to detect natural antioxidant substances in B. bicolor. The antioxidants were quantitatively and quantitatively determined using UPLC-MS, the polyphenols were evaluated based on response surface methodology (RSM), and density functional theory (DFT) calculations were performed. Results: The results showed that the optimal extraction was obtained under the following conditions: ethanol concentration 42%; solvent to solid ratio 34:1 mL/g; ultrasonic time 41 min; and temperature 40°C. The optimized experimental polyphenol value obtained under these conditions was (13.69 ± 0.13) mg/g, consistent with the predicted value of 13.72 mg/g. Eight phenolic compounds in the extract were identiffed by UPLC-MS: syringic acid, chlorogenic acid, gallic acid, rosmarinic acid, protocatechuic acid, catechin, caffeic acid, and quercetin. Chlorogenic acid exhibits the highest HOMO energy (-0.02744 eV) and the lowest energy difference (-0.23450 eV) among the studied compounds, suggesting that the compound might be the strongest antioxidant molecule. Eight phenolic compounds from the B. bicolor signiffcantly inhibited intracellular reactive oxygen species (ROS) generation, reduced oxidative stress damage in H2O2-induced HepG-2 cells. Discussion: Therefore, it was confirmed that the UAE technique is an efficient, rapid, and simple approach for extracting polyphenols with antioxidant activity from B. bicolor.

Heterodimers with a cucurbitane-type triterpenoid skeleton from the branches of Elaeocarpus dubius.

Four undescribed and two known cucurbitane-type triterpenoids, including two heterodimers, elaeocarpudubins A and B, were isolated from the branches of Elaeocarpus dubius (Elaeocarpaceae). The chemical structures of these undescribed isolates were determined by analyses of 1D and 2D NMR and MS data, electronic circular dichroism (ECD) calculations, and chemical transformation. Biogenetically, elaeocarpudubins A and B might be derived from cucurbitacin F through Michael addition with vitamin C and (-)-catechin, respectively. These six isolates were evaluated for their cytotoxic activities against human leukemia HL-60, human lung adenocarcinoma A549, human hepatoma SMMC-7721, human breast cancer MCF-7, human colon cancer SW480, and paclitaxel-resistant A549 (A549/Taxol) cell lines, for their antioxidant properties using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, and for their differentiation effects on nerve growth factor (NGF)-mediated neurite outgrowth in rat pheochromocytoma PC12 cells. Cucurbitacins F (IC50 of 4.98-38.11 µM) and D (IC50 of 0.03-4.40 µM) showed growth-inhibitory activities against these six cancer cell lines. Elaeocarpudubin B (IC50 of 61.04 µM) and elaeocarpudoside B (IC50 of 6.93 µM) showed antioxidant activities. Elaeocarpudubin B and elaeocarpudoside B also showed neurite outgrowth-promoting activities in PC12 cells at a concentration of 10 µM.

Streptothiazolidine B, a new cytotoxic alkaloid produced by Streptomyces violaceoruber.

A new cytotoxic alkaloid, named streptothiazolidine B (1), together with three known compounds (2-4), were isolated from Streptomyces violaceoruber. The structure of the undescribed compound was established using 1D and 2D NMR, and HRESIMS. Streptothiazolidine B was isolated and identified as an amide alkaloid with a unique thiazolidine side chain and its absolute configuration was determined by a combination of NOESY experiment and ECD analysis. Streptothiazolidine B exhibited significant cytotoxic activities against two human tumor cell lines, Li-7 and A2780, with IC50 values of 7.8, and 9.1 µM. Meanwhile, compound 4 showed obvious cytotoxic activities against four human tumor cell lines, THP-1, HT29, Li-7 and A2780, with IC50 values ranging from 3.1 to 10.2 µM.

Bioassay-guided isolation of cytotoxic constituents from the flowers of Aquilaria sinensis.

Bioassay-guided fractionation of the EtOH extract from the flowers of Aquilaria sinensis (Lour.) Spreng. (Thymelaeaceae) led to the isolation of a new cucurbitane-type triterpenoid, aquilarolide A (1), along with five known compounds (2-6). The structure of 1 was elucidated by extensive 1D and 2D nuclear magnetic resonance (NMR) experiments and mass spectrometry (MS) data and theoretical calculations of its electronic circular dichroism (ECD) spectra. Aquilarolide A, cucurbitacin E (3), cucurbitacin B (4), and 7-hydroxy-6-methoxy-2-[2-(4-methoxyphenyl)ethyl]-4H-1-benzopyran-4-one (6) showed significant cytotoxicity against human lung adenocarcinoma SPC-A-1, human lung squamous cell carcinoma NCI-H520, human lung adenocarcinoma A549, and paclitaxel-resistant A549 (A549/Taxol) cell lines. All four active compounds, with IC50 values ranging from 0.002 to 0.91 µM, had better inhibitory activities against A549/Taxol cells than paclitaxel (IC50 = 1.80 µM). Among them, cucurbitacin E (IC50 = 0.002 µM) is the most active. Further studies are needed to evaluate their in vivo antitumor activities and to clarify their mechanisms.

Synthesis and antitumor activity of benzophenone compound.

Seven benzophenone compounds were synthesized in one or two steps, then their antitumor activity was evaluated. The total yields ranged from 9% to 44%. Compounds 3c-5c exhibited obvious antitumor activity. Among them, compounds 3c and 4c exhibited excellent and broad-spectrum antitumor activity. Compound 3c exhibited much stronger inhibitory activities against fourteen cancer cells than cisplatin. In particular, compound 3c exhibited stronger cytotoxicity against hepatocarcinoma SMMC-7721 cells than Taxol, with a half maximal inhibitory concentration (IC50) of approximately 0.111 µM. These results demonstrated that compounds 3c, 4c and 5c were very promising antitumor leads for further structural modification.

Sesquiterpenoids and 2-(2-Phenylethyl)chromone Derivatives from the Resinous Heartwood of Aquilaria sinensis.

One novel spirolactone, aquilarisinolide (1), three new sesquiterpenoids, (2R,4S,5R,7R)-2-hydroxyeremophila-9,11-dien-8-one (2), (1R,4S,5S,7R,11R)-13-hydroxyepidaphnauran-9-en-8-one (3), and (4R,5S,7R,8S,10S,13R)-8,13-dihydroxyrotunda-1,11-dien-3-one (4), together with 13 known compounds (5-17) were isolated from the resinous heartwood of Aquilaria sinensis (Thymelaeaceae). The structures of the new compounds were elucidated based on the analysis of NMR and MS data and theoretical calculations their ECD spectra. The isolated compounds were evaluated for their protective activities against PC12 cell injury induced by corticosterone (CORT) and 1-methyl-4-phenylpyridine ion (MPP+), as well as inhibitory activities against BACE1. Compound 4, 5,6-dihydroxy-2-(2-phenylethyl)chromone (5), daphnauranol B (7), 6-methoxy-2-[2-(3-methyoxyphenyl)ethyl]chromone (10), isoagarotetrol (14), and 1-hydroxy-1,5-diphenylpentan-3-one (16) showed significant protective effects on CORT-induced injury in PC12 cells at a concentration of 20 µM (P < 0.001). Isoagarotetrol (14) showed a significant protective effect on MPP+-induced injury in PC12 cells at a concentration of 20 µM (P < 0.001), while compound 4 showed a moderate activity (P < 0.01). The BACE1-inhibitory activities of all tested compounds were very weak with less than 30% inhibition at a concentration of 20 µM.

Efficient synthesis, and antitumor and antioxidant activities of polyhydroxybenzophenone.

Five polyhydroxybenzophenones were synthesized, then their antitumor and antioxidant activities were evaluated. Compounds 1-3 and 5 exhibited obvious antitumor activity. Among them, compounds 1 and 2 exhibited stronger cytotoxicity against hepatocarcinoma SMMC-7721 cells than cisplatin, with half maximal inhibitory concentrations (IC50) of approximately 3.86 and 5.32 µM, respectively. Compounds 1, 2, and 3 exhibited stronger antioxidant activity than trolox, with IC50 values of 11.15, 10.15, and 8.91 µM, respectively, and the antioxidant mechanism and strength of all compounds were further verified using computational chemistry. These results demonstrated that compounds 1-3 and 5 were very promising leads for further structural modification.

A new sesquineolignan and four new neolignans isolated from the leaves of Piper betle, a traditional medicinal plant in Myanmar.

One new sesquineolignan, piperneolignan A (1), four new neolignans, piperneolignans B-E (2-5), and eight known compounds were isolated from the leaves of Piper betle (Piperaceae) collected from Myanmar. These new structures were determined by analysis of MS and NMR data, and the absolute configuration of piperneolignan A was elucidated by electronic circular dichroism (ECD) calculations. Piperneolignan A (1), piperneolignan B (2), hydroxychavicol (6), p-hydroxycinnamaldehyde (10), and diallylcatechol (13) possessed anti-inflammatory activity against nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophage RAW 264.7 cells with IC50 values of 9.87, 45.94, 4.80, 26.40, and 40.45 µM, respectively, compared with the positive control NG-monomethyl-l-arginine (l-NMMA, IC50 = 33.84 µM). The two hydroxy groups in the structure of hydroxychavicol are essential for activity, and dimerization or trimerization of hydroxychavicol decreases activity.

Neuroprotective compounds from the resinous heartwood of Aquilaria sinensis.

Six undescribed compounds, including three sesquiterpenoids [(4S,5S,7S,8S,11R)-7-hydroxyguai-1(10)-en-8,12-olide, aquilarisinone, and 2Z,7(13),9E-humulatrien-12-ol-5-one], one diphenylpentanone [1-(2-hydroxyphenyl)-5-phenylpentan-3-one], and two 2-(2-phenylethyl)chromones (6-epiagarotetrol and triepoxyhexahydrochromone A), along with 15 known compounds, were isolated from the resinous heartwood of Aquilaria sinensis (Thymelaeaceae). Their structures were determined by mass (MS) and nuclear magnetic resonance (NMR) spectroscopic data. The absolute configuration of (4S,5S,7S,8S,11R)-7-hydroxyguai-1(10)-en-8,12-olide was confirmed by X-ray diffraction analysis, and the configurations of (4S,7S,8S,10R,11R)-7,10-epoxyguai-1(5)-en-8,12-olide, aquilarisinone, 6-epiagarotetrol, and triepoxyhexahydrochromone A were confirmed by electronic circular dichroism (ECD) calculations. The neuroprotective activities of the compounds were evaluated using models of BACE1 inhibition and PC12 cells with corticosterone- and 1-methyl-4-phenylpyridine ion (MPP+)-induced damage. At concentrations of 1, 2, and 5 µM, triepoxyhexahydrochromone A, (+)-(7R,10R)-selina-4,11(13)-diene-12,15-dial, (-)-(5R,7R,10R)-12,15-dioxo-α-selinene, and (+)-(1R,4S,5R)-1ß-hydroxyeremophila-7(11),9-dien-8-one exerted significant protective effects (p < 0.01) on PC12 cell injury induced by corticosterone, while triepoxyhexahydrochromone A and (-)-(5R,7R,10R)-12,15-dioxo-α-selinene exerted significant protective effects (p < 0.01) on MPP+-induced PC12 cell injury at concentrations of 1, 2, and 5 µM. No compounds produced significant inhibitory effects on BACE1, with inhibition rates of less than 20% observed at a concentration of 20 µM.

Chemical Constituents from the Whole Plant of Cuscuta reflexa.

Two new 2H-pyran-2-one glucosides, cuscutarosides A (1) and B (2), and one new steroidal glucoside, 7ß-methoxy-ß-sitosterol 3-O-ß-glucopyranoside (3), together with 12 known compounds (4-15) were isolated from the whole plant of Cuscuta reflexa (Convolvulaceae) collected from Myanmar. The chemical structures of these new compounds were elucidated based on extensive spectroscopic analysis. The antiobesity activity of these isolates was evaluated using porcine pancreatic lipase (PPL), and the antiplatelet aggregation activity was screened using rabbit platelets induced by thrombin, platelet-activating factor (PAF), arachidonate (AA), or collagen. 7ß-Methoxy-ß-sitosterol 3-O-ß-glucopyranoside (3) showed weak PPL inhibitory activity. Cuscutaroside A (1), its acetylated derivative (1a), and scrophenoside B (8) showed weak inhibitory activity against rabbit platelet aggregation induced by collagen. Compound 1a also showed inhibitory activity against rabbit platelet aggregation induced by AA.

Chemical Constituents from Ethanoic Extracts of the Aerial Parts of Leea aequata L., a Traditional Folk Medicine of Myanmar.

We aimed at reporting the chemical constituents and antimicrobial activities of Leea aequata L., a traditional folk medicine used in Myanmar for the treatment of wounds and skin diseases. A new neolignan, (7S,8R)-9'-O-acetylcedrusin (1), a new lactam, (3S,4S)-4-chloro-3-hydroxypiperidin-2-one (2), along with 21 known compounds, including five lignans (3-7), four flavonoid glycosides (8-11), and others (12-23), were isolated from the ethanoic extract of the aerial parts of L. aequata. The structures of the new compounds were determined by NMR, MS, and ECD spectra. For all the antimicrobial tests of the 23 compounds, only 3,4,5-trihydroxybenzoic acid ethyl ester (17) showed weak inhibitory activities against Escherichia coli and Salmonella enterica subsp. enterica.

New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum.

Two new amides (E)-N-cinnamoyl-2-methoxypiperidine (1) and (R)-1-(2-oxopyrrolidin-3-yl)-5,6-dihydropyridin-2(1H)-one (2), four new amide glucosides, retrofractosides A-D (3-6), and two new phenylpropanoid glucosides, retrofractosides E (7) and F (8), together with 24 known compounds (9-32) were isolated from the fruits of Piper retrofractum. The chemical structures of these new compounds were elucidated based on extensive spectroscopic analysis. All of these isolates (1-32) were evaluated for inhibitory activity against mouse platelet aggregation induced by the peptide AYPGKF-NH2. (E)-N-(Tetrahydro-2H-pyran-2-yl)cinnamamide (9) showed a weak inhibitory effect, with an inhibition ratio of 52.0% at a concentration of 150 µM.

A new pregnane steroid from cultures of Aspergillus versicolor.

A new pregnane steroid, named aspergillon A (1), together with two known compounds, (22E,24R)-ergosta-5,7,22-trien-3ß-ol (2) and (22E, 24R)-ergosta-4,6,8(14),22-tetraen-3-one (3) were isolated from cultures of the tin mine tailings-associated fungus Aspergillus versicolor. The new structure and absolute configuration were determined with the help of extensive spectroscopic analyses and quantum chemical calculations of the electronic circular dichroism (ECD) spectra.

Cytotoxic garcimultiflorones K-Q, lavandulyl benzophenones from Garcinia multiflora branches.

Seven undescribed lavandulyl benzophenones garcimultiflorones K-Q, and fourteen known compounds were isolated from the CHCl3 soluble fraction of 95% EtOH extract of Garcinia multiflora branches. Their structures and absolute configurations were determined by spectroscopic techniques including NMR spectroscopy, MS analysis, and ECD calculations. Seven isolated compounds expect for garcimultiflorone L and garcimultiflorone O exhibited cytotoxic activities in vitro against five cancer cell lines (HL-60, A549, SMMC-7721, MCF-7, and SW480). It is worth mentioning that garcimultiflorone Q exhibited most significant cytotoxicities against five cancer cell lines with IC50 values ranging from 3.07-12.56 µM.

Synthesis and antitumor, antityrosinase, and antioxidant activities of xanthone.

Ten substituted 1,3-dihydroxyxanthones were synthesized in one step. The yields ranged from 40 to 76%. Compounds 8-10 were first reported. Next, the compounds' in vitro anti-proliferative activities against nine human cancer cell lines, antityrosinase, and antioxidant activities were evaluated. Compounds 1, 4, 6-7, and 9-10 exhibited enhanced cytotoxicity against certain cancer cells. Compounds 2, 8, 9, and 10 inhibited tyrosinase activity to a certain extent. In addition, compound 4 exhibited the best antioxidant activity, which was consistent with theoretical calculations. These results demonstrated that compounds 1-2, 4, and 6-10 were promising leads for further investigation.

[Density functional theory investigation on antioxidant activity of five flavonoids from Hebei Xiangju].

Five main flavonoids of Hebei Xiangju were studied using the Density Functional Theory (DFT) B3LYP method with 6-311 G (d) basis set．Their activities were analyzed based on molecular structure,bond dissociation energy (BDE),natural orbital charge distribution (NBO),bond order and the energy gap between HOMO and LUMO. The results showed that the existing of intra molecular hydrogen bond in B ring can improve the antioxidant activity of the flavonoids, at the same time, the hydroxyl groups on the glycosides do not have the activity of eliminating free radicals, but decrease the total molecular antioxidant activity. As a result, the antioxidant ability order of the five flavonoids compounds is luteolin< luteolin-7-O-glucoside< apigenin < acacetin < acacetin-7-O-glucose, which is agreement with the experimental conclusion reported in literature. The results showed that the DFT method can provide theoretical guidance for the selection of natural flavonoid antioxidants.

Phomopchalasins A and B, Two Cytochalasans with Polycyclic-Fused Skeletons from the Endophytic Fungus Phomopsis sp. shj2.

Phomopchalasins A (1) and B (2), two novel cytochalasans with unprecedented carbon skeletons, and phomopchalasin C (3), containing a rare hydroperoxyl motif, were obtained from the endophytic fungus Phomopsis sp. shj2, which was first isolated from the Isodon eriocalyx var. laxiflora. Their structures were elucidated by extensive spectroscopic analyses, electronic circular dichroism (ECD) calculation, and X-ray crystallographic analysis. Notably, 1 possessed an unprecedented 5/6/5/8-fused tetracyclic ring system, and 2 featured a novel 5/6/6/7/5-fused pentacyclic skeleton. The cytotoxic, anti-inflammatory, and antimigratory activities of 1-3 were evaluated in vitro.

Chemical constituents from fruiting bodies of Basidiomycete Perenniporia subacida.

Four new aromatic abietane diterpenoids and two new benzene derivatives, namely perenacidins A-F (1-6), have been isolated from the fruiting bodies of Basidiomycete Perenniporia subacida. The structures were elucidated by means of extensive spectroscopic methods and computational ECD method. The antifungal activities against Canidia albicans and the cytotoxic activities against four cancer cell lines (including K-562, A-549, SMMC-7721, MCF-7) were evaluated in vitro.

[Density functional theory investigation on antioxidation activity of four flavonoids from Rhododendri Daurici Folium].

Four main flavonoids of the Chinese medicine Rhododendri Daurici Folium were studied using the density functional theory (DFT) B3LYP method with 6-311 + + G (d, p) basis set．Their activities were analyzed based on molecular structure, bond dissociation energy (BDE) and the energy gap between HOMO and LUMO. As a result, the antioxidant ability order of the four flavonoids compounds is farrerol

Brasilane sesquiterpenoids and alkane derivatives from cultures of the basidiomycete Coltricia sideroides.

Three new brasilane-type sesquiterpenoids, brasilanes A-C (1-3), together with two new alkane derivatives, colisiderin A (4) and 7(E),9(E)-undecandiene-2,4,5-triol (5), were isolated from cultures of the basidiomycete Coltricia sideroides. Their structures were elucidated by NMR and MS data analyses. The absolute configuration of 4 was determined by TDDFT ECD calculations while brasilane-type sesquiterpenoids were isolated from cultures of mushroom for the first time. Compounds 2 and 4 showed weak cytotoxicities against HL-60 and SW480, respectively.