A new Secondary metabolites of the crinoid (Comanthina schlegeli) associated fungus Alternaria brassicae 93

Fungus Alternaria brassicae 93 isolated from crinoid (Comanthina schlegeli), which was collected from the South China Sea. Six compounds were isolated from A. brassicae 93, including one new compound (1), along with five known compounds, ochratoxin A methyl ester (2), cis-4-hydroxym-ellein (3), (R)-7-hydroxymellein (4), trans-2-anhydromevalonic (5) and protocatechuic acid (6). Their structures were determined by spectroscopic methods and comparison with reported data. Cytotoxicity against two human cancer cell lines and antibacterial activity against twelve aquatic bacteria of compound 1 were also tested.     

Three new sesquiterpenes from Ainsliaea glabra

Three new sesquiterpenes: 4-acrylic-6-methyl-α-tetralone (1), ainsliaea acid A (2) and ainsliaea acid B (3), together with 8 known compounds (4-11) were isolated from the whole herb of Ainsliaea glabra and their structures were established by means of 1D and 2D NMR spectroscopy and HR-ESIMS. Compounds 1–6 were tested for the inhibition of nuclear factor kappa B (NF-κB) in the 293-NF-κB-luciferase reporter cell line induced by lipopolysaccharide (LPS), and compound 2 was further tested for the production of tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), IL-6 and IL-10 in RAW264.7 macrophages induced by LPS. The isolated compound 2 exhibited significant anti-inflammatory activity.     

Iridoid,phenylethanoid and flavonoid glycosides from Forsythia suspensa

Abstract

As part of our continuing efforts to explore bioactive compounds from natural resources, a new iridoid glycoside, adoxosidic acid-6′-oleuroperic ester (1), together with one known phenylethanoid glycoside (2) and two known flavonoid glycosides (3–4) were isolated from the fruit of Forsythia suspensa. The structure of the new compound (1) was elucidated through 1D and 2D NMR spectroscopic data and HR-ESIMS. Interestingly, compound 1 was a monoterpene ester of one iridoid glycoside. Compounds 2–4 were identified as calceolarioside A (2), kaempferol-3-O-rutinoside (3), kampferol-3-O-robinobioside (4) on the basis of NMR spectroscopic data analyses and comparison with the data reported in the literature. The antiviral activity aganisist influenza A (H5N1) virus of compound 1 was studied as well.     

A new di-C-prenylated coumarin from Sophora interrupta

A new di-C-prenylated coumarin, 7-methoxy-6,8-bis-(2,3-dihydroxy-3-methylbutyl)-coumarin (1), together with seven known compounds, isopimpinellin (2), an arylbenzofuran (3), three flavonoids (4–6), (+)-maackianin (7) and echinoisoflavanone (8), were isolated from the leaves of Sophora interrupta Bedd. The structure of the new compound 1 as well as known compounds was elucidated by extensive 1D and 2D NMR spectral studies.     

A novel compound from <Emphasis Type="Italic">Flos carthami</Emphasis> and its bioactivity

A novel compound, 4-{1′-hydroxy-1′-mercapto-1′-[1′′-2′′(N→O)-isoquinolyl]}yl-1-benzoic acid (1), together with six known compounds, 6-hydroxykaempferol-3-O-β-D-glucopyranoside (2), rutin (3), quercetin-3-O-β-D-glucopyranoside (4), kaempferol-3-O-β-D-glucopyranoside (5), cartormin (6), hydroxysafflor yellow A (7), were isolated by chromatography from the n-BuOH fraction of 50% ethanol extraction of Flos carthami. Their structures were elucidated on the basis of spectral analysis and comparison with published data. Among them, compound 1 was shown to possess a weak protective effect against cerebral ischemic damage in rats. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 339–341, May–June, 2009.     

A new furan derivative from an endophytic Aspergillus flavus of Cephalotaxus fortunei

A new furan derivative named 5-acetoxymethylfuran-3-carboxylic acid (2), together with a known furan compound, 5-hydroxymethylfuran-3-carboxylic acid (1), were isolated from the fermentation of Aspergillus flavus, endophytic fungi in Cephalotaxus fortunei. The structures of 1 and 2 were elucidated by NMR, IR, UV and MS data, as well as compared with literature data. The compounds 1 and 2 exhibited potent antibacterial activity against Staphylococcus aureus with MIC values of 31.3 and 15.6 μg/mL, respectively. The compound 2 showed moderate antioxidant activity.     

A new tigliane-type diterpene ester from <Emphasis Type="Italic">Wikstroemia scytophylla</Emphasis>

A new tigliane-type diterpene ester, wiksphyllamin B (1), and one known compound, 12-O-benzoylphorbol 13-octanoate (2), were isolated from the stems of Wikstroemia scytophylla Diels. Their structures were identified using spectroscopic methods. The incorrect assignment of ¹³C NMR data of compound 2 in the literature was revised according to the 2D NMR spectra.     

A new oxo-sterol derivative from the rhizomes of Costus speciosus

Chemical investigation of the rhizomes of Costus speciosus led to the isolation of a new compound, 22-ketocholesteryl palmitate (1) along with four known compounds, 24-methylenecycloartanol (2), cycloartanol (3), stigmasterol (4) and linoleic acid (5). The structure of new compound was characterised by extensive 1D-, 2D-NMR and mass spectrometry (GC-MS and HR-ESI-MS) techniques.     

A new aliphatic ester of hydroxysalicylic acid from fermented Carica papaya L. preparation with a potential hair growth stimulating activity

Abstract

An aliphatic ester of hydroxysalicylic acid (6), reported for the first time from a natural source in addition to five known compounds were isolated from the fermented Carica papaya L. preparation, a commercialized functional food. The known compounds were identified as 5-hydroxymethylfurfuraldehyde (1), trans-caffeic acid (2), butyl 4-hydroxybenzoate (butylparaben) (3), lycopene (4), benzyl isothiocyanate (5). Compounds 1 and 3 were reported for the first time from Papaya fruits through this study. The new compound showed a moderate antioxidant activity and a potent hair growth stimulating activity in vitro.     

Antimicrobial and antioxidant activities of a new benzamide from endophytic Streptomyces sp. YIM 67086

A new benzamide (1) and four known compounds (2–5) were isolated from endophytic Streptomyces YIM67086, and their structures were determined as 2-amino-3,4-dihydroxy-5-methoxybenzamide (1), 4-hydroxy-3-methoxybenzoic acid (2), phenylacetic acid (3), N-acetyltyramine (4) and p-hydroxytruxinic acid (5). Compound 5 was first found in the microorganism. The antimicrobial activities of compounds 1–5 and antioxidant activity of compound 1 were investigated.     

New compound from Euphorbia alatavica Boiss

One new compound alatavinol (1), together with five known compounds, kaempferol (2), quercetin (3), laricircsinol (4), secoisolariciresinol (5) and loliolide (6) were isolated from the whole plant of Euphorbia alatavica Boiss. Those compounds were isolated and purified by various column chromatographic methods and their structures were elucidated by spectroscopic (1D, 2D NMR, and HR-MS) chemical analyses. All compounds were isolated for the first time from E. alatavica Boiss, and biochemical pathway of the new compound has been hypothesized. Furthermore, these compounds were evaluated for antioxidant properties based on the DPPH radical scavenging activities. Results showed that IC₅₀ values of compounds 1, 3, 4, 5 and 6 were 25.69, 1.88, 2.87, 11.55 and 17.81 μg/mL, respectively, as compared to the control ascorbic acid (5.34 μg/mL).     

Two new compounds from cultures of the basidiomycete Antrodiella albocinnamomea

A new linear triterpene (1), and a new sesquiterpene (2), together with a known compound methyl indole-3-carboxylate (3) were isolated from the crude extract of Antrodiella albocinnamomea. The structures of the new compounds 1–2 were determined by comprehensive spectroscopic analysis. Compound 1 exhibited signi?cant inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) with IC₅₀ value of 1.0 μg/mL.     

Four cytotoxic annonaceous acetogenins from the seeds of Annona squamosa

Four new annonaceous acetogenins (ACGs), squamocin-I (1), II (2) and III (3) and squamoxinone-D (4), together with seven known ACGs (5–11), were isolated from the seeds of Annona squamosa. The structures of all isolates were elucidated and characterised by spectral and chemical methods. Compounds 1–4 were evaluated for their cytotoxicities against Hep G2, SMMC 7721, BEL 7402, BGC 803 and H460 human cancer cell lines. Compound 1 exhibited better potent activity than the positive compound and compound 3 shows selectively cytotoxical activity against H460 with IC₅₀ values of 0.0492 μg/ml.     

A new cadinane sesquiterpenoid glucoside with cytotoxicity from Abelmoschus sagittifolius

A new cadinane sesquiterpenoid glucoside, 2β,7,3-trihydroxycalamenene 3-O-β-d-glucoside (1) together with six known compounds, N-(p-trans-coumaroyl)-N-methyl tyramine (2), Cleomiscosin A (3), 9,12,13-trihydroxy-10,15-heptadecadienoic acid (4), Cytochalasin B (5), Marmesinin (6) and N-(p-trans-coumaroyl) tyramine (7) were obtained from the stem bark of Abelmoschus sagittifolius. The new structure of compound 1 was elucidated by analysing its ¹H and ¹³C-NMR, ¹H-¹H COSY, HSQC, HMBC, NOESY and HR-ESI-MS spectra. Compounds 1–7 showed moderate cytotoxicity against Hela and HepG-2 human cancer cell lines.     

Constituents of fruit pulp of <Emphasis Type="Italic">Maytenus salicifolia</Emphasis> and complete 1D/2D NMR data of 3<Emphasis Type="Italic">β</Emphasis>-hydroxy-D:B-friedo-olean-5-ene

A mixture of long-chain hydrocarbons constituted by nonacosane (29C, 7.5%), hentriacontane (31C, 48.3%), and tritriacontane (33C, 30.1%), the ester 1′-acetyloxymethylpentacosa-20′-enyl 10-hydroxydecanoate (2), β-amyrin (3), friedelin (4), and lupeol (5), and 3β-hydroxy-D:B-friedo-olean-5-ene (6) were identified as constituents of fruits of Maytenus salicifolia Reissek (Celastraceae). The structural formula and the stereochemistry of compound 6 were established by the data obtained through ¹H and ¹³C NMR spectroscopy, including DEPT-135 and 2D (HMQC, HMBC, and NOESY) experiments. By analysis of the spectral data, it was possible to correct seven chemical shift assignments of compound 6, which were erroneous attributed and published in the scientific literature.     

Complete basis set,hybrid-DFT study,and NBO interpretations of the conformational behavior of 1,2-dihaloethanes

The conformational behavior of 1,2-difluoroethane (1), 1,2-dichloroethane (2), 1,2-dibromoethane (3), and 1,2-diiodoethane (4) have been analyzed by means of complete basis set CBS-QB3, hybrid-density functional theory (B3LYP/Def2-TZVPP) based methods and natural bond orbital (NBO) interpretation. Both methods showed the expected greater stability of the gauche conformation of compound 1 compared to its anti conformation. Contrary to compound 1, the anti conformations of compounds 2–4 are more stable than their gauche conformation. The stability of the anti conformation compared to the gauche conformation increases from compound 1 to compound 4. The NBO analysis of donor–acceptor (σ → σ*) interactions showed that the generalized anomeric effect (GAE) is in favor of the gauche conformation of compound 1. Contrary to compound 1, GAE is in favor of the anti conformations of compounds 2–4. The GAE values calculated (i.e., GAE_anti − GAE_gauche) increase from compound 1 to compound 4. On the other hand, the calculated dipole moment values for the gauche conformations decrease from compound 1 to compound 4. In the conflict between the GAE and dipole moments, the former succeeded in accounting for the increase of the anti conformation stability from compound 1 to compound 4. There is a direct correlation between the calculated GAE, ∆[r _c–c(G) − r _c–c(A)] and ∆[r _c–x(A) − r _c–x(G)] parameters. The correlations between the GAE, bond orders, total steric exchange energies (TSEEs), ΔG _{Anti–Gauche}, ΔG ^‡(Gauche → Gauche′, C _2v), ΔG ^‡(Anti → Gauche, C ₂), dipole–dipole interactions, structural parameters, and conformational behaviors of compounds 1–4 have been investigated.     

A new antifungal and antiprotozoal bibenzyl derivative from Gavilea lutea

A new bibenzyl derivative (4), together with two glycosylated flavonoids (1 and 2), batatasin III (3) and the phenanthrene isohircinol (5) were isolated from the aerial parts of Gavilea lutea. Their structures were elucidated on the basis of spectroscopic studies including 1D and 2D NMR, UV, IR and HRESIMS. All isolated compounds were evaluated for their antifungal activity towards Candida albicans. The new compound 4 showed inhibitory activity with a MIQ of 50 μg. In addition, compound 4 exhibited a selective activity (IC₅₀ = 2.3 μg/mL) against Leishmania donovani.     

A new isochroman derivative from the marine fungus <Emphasis Type="Italic">Phomopsis</Emphasis> sp. (No. ZH-111)

A new isochroman, (3R,4S)-3,4-dihydro-4,5,8-trihydroxy-3-methylisocoumarin (1), and two known compounds were isolated from the marine fungus Phomopsis sp. (No. ZH-111). Their structures were determined by spectroscopic methods, mainly 1D and 2D NMR. Preliminary pharmacological test revealed that compound 1 and exumolide A (3) can accelerate the growth of subintestinal vessel plexus (SIV) branches markedly and compound 2 can inhibit the growth of subintestinal vessel plexus (SIV) branches.     

Molecular docking studies and in vitro cholinesterase enzyme inhibitory activities of chemical constituents of Garcinia hombroniana

Garcinia species are reported to possess antimicrobial, anti-inflammatory, anticancer, anti-HIV and anti-Alzheimer's activities. This study aimed to investigate the in vitro cholinesterase enzyme inhibitory activities of garcihombronane C (1), garcihombronane F (2), garcihombronane I (3), garcihombronane N (4), friedelin (5), clerosterol (6), spinasterol glucoside (7) and 3β-hydroxy lup-12,20(29)-diene (8) isolated from Garcinia hombroniana, and to perform molecular docking simulation to get insight into the binding interactions of the ligands and enzymes. The cholinesterase inhibitory activities were evaluated using acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. In this study, compound 4 displayed the highest concentration-dependent inhibition of both AChE and BChE. Docking studies exhibited that compound 4 binds through hydrogen bonds to amino acid residues of AChE and BChE. The calculated docking and binding energies also supported the in vitro inhibitory profiles of IC₅₀. In conclusion, garcihombronanes C, F, I and N (1–4) exhibited dual and moderate inhibitory activities against AChE and BChE.     

A novel dimeric flavonol glycoside from Cynanchum acutum subsp. sibiricum

A novel dimeric flavonol glycoside, Cynanflavoside A (1), together with six analogues, kaempferol-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (2), quercetin-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (3), kaempferol-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside (4), quercetin-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside (5), kaempferol-3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside (6), and quercetin-3-O-galactoside (7) were isolated from the n-butyl alcohol extract of Cynanchum acutum subsp. sibiricum. Their structures were determined spectroscopically and compared with previously reported spectral data. All compounds were evaluated for their anti-complementary activity in vitro, and only compound 5 exhibited anti-complement effects with CH₅₀ value of 0.33 mM.