Pharmacological Evaluation of Novel Organoiron Dendrimers as Antimicrobial and Anti‐Inflammatory Agents

The synthesis of a novel and attractive class of nonsteroidal anti‐inflammatory and antimicrobial organoiron dendrimers attached to the well‐known drug ibuprofen is achieved. The structures of these dendrimers are established by spectroscopic and analytical techniques. The antimicrobial activity of these dendrimers is investigated and tested against five human pathogenic Gram‐positive and Gram‐negative bacteria, and minimum inhibitory concentrations are reported. Some of these synthesized dendrimers exhibit higher inhibitory activity against methicillin‐resistant Staphylococcus aureus, vancomycin‐resistant Enterococcus faecium, and Staphylococcus warneri compare to the reference drugs. As well, the in vitro and in vivo anti‐inflammatory activities of these dendrimers are evaluated. The results of in vivo anti‐inflammatory activity and histopathology of inflamed paws show that all dendrimers display considerable anti‐inflammatory activity; however, second‐generation dendrimer ( G2‐D6 ) shows the best anti‐inflammatory activity, which is more potent than the commercial drug ibuprofen at the same tested dose. Results of the toxicity study reveal that G2‐D6  is the safest drug on biological tissues.     

New ent‐Pimarane Diterpenes from the Roots of Aralia dumetorum

Four new ent‐pimarane diterpenes were isolated from the EtOH extract of Aralia dumetorum, together with three known compounds involving ent‐pimar‐8(14),15‐dien‐19‐oic acid ( 5 ), ent‐pimar‐8(14),15‐dien‐19‐ol ( 6 ), and ent‐kaur‐16‐en‐19‐oic acid ( 7 ). By detailed analyses of the MS, IR, and NMR data, the structures of four new diterpenes were characterized as (5β,9β,10α,13α)‐pimara‐6,8(14),15‐trien‐18‐oic acid ( 1 ), (5β,7β,9β,10α,13α)‐7‐methoxypimara‐8(14),15‐dien‐18‐oic acid ( 2 ), (5β,9β,10α,13α,14β)‐14‐methoxypimara‐7,15‐dien‐18‐oic acid ( 3 ), and (5β,10α,13α,14α)‐14‐hydroxypimara‐7,9(11),15‐trien‐18‐oic acid ( 4 ). The cytotoxic activities of compounds 1  –  7 were assayed in vitro through MTT method.     

Three New Chalcones from the Aerial Parts of Angelica keiskei

Three new chalcones, 3′‐carboxymethyl‐4,2′‐dihydroxy‐4′‐methoxychalcone ( 1 ), (±)‐4,2′,4′‐trihydroxy‐3′‐[(3‐hydroxy‐2,2‐dimethyl‐6‐methylenecyclohexyl)methyl]chalcone ( 2 ), and 2′′‐hydroxyangelichalcone ( 3 ), were isolated from the aerial parts of Angelica keiskei (Umbelliferae) together with five known compounds, artocarmitin A ( 4 ), (+)‐cis‐(3′R,4′R)‐methylkhellactone ( 5 ), (?)‐trans‐(3′R,4′S)‐methylkhellactone ( 6 ), 3,4‐dihydroxanthotoxin ( 7 ), and (Z)‐p‐coumaryl alcohol ( 8 ). The known compounds 4  –  8 were identified from A. keiskei for the first time. The structures of 1  –  3 were elucidated by interpreting spectroscopic data including 1D‐ and 2D‐NMR.     

Megastigmane Glycosides from Docynia indica and Their Anti‐inflammatory Activities

Using various chromatographic methods, three new megastigmane glycosides, docynicasides A – C ( 1  –  3 ) and ten known, (6S,9R)‐vomifoliol 9‐O‐β‐d ‐xylopyranosyl‐(1′′→6′)‐O‐β‐d ‐glucopyranoside ( 4 ), hyperin ( 5 ), quercitrin ( 6 ), quercetin 3‐α‐l ‐arabinofuranoside ( 7 ), naringenin 7‐O‐β‐d ‐glucopyranoside ( 8 ), phloridzin ( 9 ), phloretin 2′‐O‐β‐d ‐xylopyranosyl‐(1→6)‐β‐d ‐glucopyranoside ( 10 ), pinosylvin 3‐O‐β‐d ‐glucopyranoside ( 11 ), tormentic acid ( 12 ), and chlorogenic acid methyl ester ( 13 ) were isolated from the fruits of Docynia indica. Their chemical structures were elucidated by physical and chemical methods. All the isolated compounds were evaluated for the inhibitory activity on NO production in LPS‐stimulated BV2 cells. As the results, compounds 3  –  5 showed significant inhibitory activity on LPS‐stimulated NO production in BV2 cells with the IC₅₀ values ranging from 21.0 to 29.3 μm .     

Baeckeins J and K,Two Novel C‐Methylated Biflavonoids from the Roots of Baeckea frutescens and Their Cytoprotective Activities

Baeckea frutescens is an aromatic shrub used as ornamentals and as food flavor spices in the southern part of P. R. China. Two novel C‐methylated biflavonoids named baeckeins J ( 1 ) and K ( 2 ) were isolated from the roots of B. frutescens, which possessed the unique carbon skeleton conjugated of a flavonol and one isoflavanonol molecule via the linkages of C(2)–C(8*) and C(3)–O–C(7*). The structures of compounds 1 and 2 were elucidated by analysis of 1D‐ and 2D‐NMR, and HR‐ESI‐MS spectral data, and the absolute configuration for chiral C‐atoms C(2) and C(3) were assigned by CD spectrometry combined with quantum chemical calculations. In the bioassay, baeckeins J and K exhibited strong cytoprotective effects on H₂O₂‐induced oxidative cell death in PC12 cells.     

Xanthone O‐Glycosides from the Roots of Pteris Multifida

Two new xanthone glycosides and six known compounds were isolated from the roots of Pteris multifida. Based on spectroscopic and chemical methods, the structures of the new compounds were elucidated as 1‐hydroxy‐4,7‐dimethoxy‐8‐(3‐methyl‐2‐butenyl)‐6‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐[β‐D‐glucopyranosyl‐(1→3)]‐β‐D‐glucopyranosylxanthone ( 1 ), and 1,3‐dihydroxy‐7‐methoxy‐8‐(3‐methyl‐2‐butenyl)‐6‐O‐α‐L‐rhamnopyranosyl‐(1 →2)‐[β‐D‐glucopyranosyl‐(1→3)]‐β‐D‐glucopyranosylxanthone ( 2 ), respectively.     

Flavonoids Isolated from Heat‐Processed Epimedium koreanum and Their Anti‐HIV‐1 Activities

Systematic phytochemical investigation on heat‐processed Epimedium koreanum led to the isolation of 13 flavonoids, including five new prenyl‐flavonol glycosides, koreanosides A–E ( 1 – 5 , resp.). Their structures were elucidated on the basis of detailed analysis of the 1D‐ and 2D‐NMR spectroscopic data and chemical reactions. Apigenin ( 11 ) exhibited moderate anti‐HIV‐1 activity with an EC₅₀ value of 12.8±3.27 μg/ml.     

Development and validation of an ultra‐performance convergence chromatography method for the quality control of Angelica gigas Nakai

Ultra‐performance convergence chromatography, which integrates the advantages of supercritical fluid chromatography and ultra high performance liquid chromatography technologies, is an environmentally friendly analytical method that uses dramatically reduced amounts of organic solvents. An ultra‐performance convergence chromatography method was developed and validated for the quantification of decursinol angelate and decursin in Angelica gigas using a CSH Fluoro‐Phenyl column (2.1 mm × 150 mm, 1.7 μm) with a run time of 4 min. The method had an improved resolution and a shorter analysis time in comparison to the conventional high‐performance liquid chromatography method. This method was validated in terms of linearity, precision, and accuracy. The limits of detection were 0.005 and 0.004 μg/mL for decursinol angelate and decursin, respectively, while the limits of quantitation were 0.014 and 0.012 μg/mL, respectively. The two components showed good regression (correlation coefficient (r²) > 0.999), excellent precision (RSD < 2.28%), and acceptable recoveries (99.75–102.62%). The proposed method can be used to efficiently separate, characterize, and quantify decursinol angelate and decursin in Angelica gigas and its related medicinal materials or preparations, with the advantages of a shorter analysis time, greater sensitivity, and better environmental compatibility.     

(+)‐(14β)‐14‐Ethylmatridin‐15‐one,a New Quinolizidine Alkaloid from the Poisonous Plant Oxytropis ochrocephala Bunge

A new matrine alkaloid derivative (+)‐(14β)‐14‐ethylmatridin‐15‐one ( 1 ) was isolated from the poisonous plant Oxytropis ochrocephala Bunge . The structure was established by spectroscopic methods, including extensive 1D‐ and 2D‐NMR experiments.     

Myrothecoside,a Novel Glycosylated Polyketide from the Terrestrial Fungus Myrothecium sp. GS‐17

Based on the chemical analysis and targeted bioactivity screening, a new polyketide glycoside, myrothecoside, was isolated from a terrestrial halotolerant fungus, Myrothecium sp. GS‐17. The structure of myrothecoside was elucidated on the basis of extensive spectroscopic analysis including 1D‐ and 2D‐NMR (¹H,¹H‐COSY, HSQC, HMBC, and NOESY) experiments, combined with mass spectroscopic data and physicochemical properties. This compound exhibited weak cytotoxicity against human leukemia (HL‐60) cancer cell with an IG₅₀ value of 63.61 μm , and also antifungal activities against plant pathogenic fungi Rhizoctonia solani and Fusarium oxysporum using standard agar diffusion tests at 20 μg/disk.     

A Novel High Efficient Catalyst AgBr/CaMoO4 for the Reduction of p‐Nitrophenol

A new composite catalyst AgBr/CaMoO₄ was successfully fabricated by loading AgBr nanoparticles on CaMoO₄ support via a convenient precipitation/deposition method, without any controlling agent and template. The microstructure, chemical composition, and morphologies of the AgBr/CaMoO₄ were characterized by X‐ray diffraction, Fourier transform infrared, X‐ray photoelectron spectroscopy, and scanning electron microscopy. A series of comparative experiments showed that the composite AgBr/CaMoO₄ exhibits higher catalytic activity than pure AgBr or CaMoO₄ for the reduction of p‐nitrophenol (4‐NP). Moreover, the AgBr content greatly impacted the catalytic activity of composite AgBr/CaMoO₄ . The conversion rate of 4‐NP with AgBr/CaMoO₄ ‐5% as catalyst could reach 100% within only 4 min, which might be attributed to more number of available active sites from the highly dispersed AgBr nanoparticles on the surface of CaMoO₄ microspheres. In addition, the composite catalyst AgBr/CaMoO₄ displayed a good structural and cycling stability. The present study might provide a new strategy to design composite materials with excellent catalytic performance.     

Synthesis of Some Novel 1,4‐Phenylene‐bis‐thiazolyl Derivatives and Their Anti‐hypertensive α‐blocking Activity Screening

A series of novel 1,4‐phenylene‐bis‐thiazolyl derivatives were synthesized and evaluated for their anti‐hypertensive activities as α‐blocking agents and some of them showed promising activities.     

Molecular Weight and Proposed Structure of the Angelica sinensis Polysaccharide‐iron Complex

The molecular weight and the proposed structure of the Angelica sinensis polysaccharide‐iron complex (APIC) were studied. Fourier transform infrared spectroscopy, X‐ray powder diffraction, differential scanning calorimetry, transmission electron microscopy, electron paramagnetic resonance, thermogravimetric analysis, atomic force microscopy, and gel filtration chromatography were used to characterize APIC, which is a macromolecule complex composed of Angelica sinensis polysaccharide (ASP) and iron. The structure of APIC was proposed to be a polynuclear ferrihydrite core chelated firmly by an encircling framework of ASP chains, forming a core molecule, which is surrounded by a removable outer protective sheath of colloidal ASP. And the molecular formula of APIC was proposed to be {[(Fe₂O₃·2.2H₂O)₁₀₄₃(ASP)₃₂](ASP)₁₂}, with MW=270000 Da.     

New Compounds from the Roots and Stems of Trigonostemon lii and Their Cytotoxic Activities

A new carboline alkaloid, Trifiline D ( 1 ) and a new degraded diterpenoid, Trigoxyphin X ( 4 ) were isolated from the roots and stems of Trigonostemon lii. Their structures were elucidated by extensive spectroscopic analyses including 1D‐ and 2D‐NMR techniques. Compound 1 exhibited weak inhibitory activity against MCF‐7, A‐549, MGC‐803, and COLO‐205 with IC₅₀ values ranging from 27.4 to 35.4 μm .     

Two New Cyclic Tetrapeptides of Streptomyces rutgersensis T009 Isolated from Elaphodus davidianus Excrement

Two new cyclic tetrapeptides, cyclo(l ‐Val‐l ‐Leu‐l ‐Val‐l ‐Ile) ( 1 ) and cyclo(l ‐Leu‐l ‐Leu‐l ‐Ala‐l ‐Ala) ( 2 ), and 15 known compounds, cyclo(Gly‐l ‐Leu‐Gly‐l ‐Leu) ( 3 ), cyclo(l ‐Ser‐l ‐Phe) ( 4 ), cyclo(l ‐Leu‐l ‐Ile) ( 5 ), cyclo(l ‐Tyr‐l ‐Phe) ( 6 ), cyclo(Gly‐l ‐Trp) ( 7 ), cyclo(l ‐Leu‐l ‐Tyr) ( 8 ), cyclo(Gly‐l ‐Phe) ( 9 ), cyclo(l ‐Phe‐trans‐4‐hydroxy‐l ‐Pro) ( 10 ), cyclo(l ‐Leu‐l ‐Leu) ( 11 ), cyclo(l ‐Val‐l ‐Phe) ( 12 ), cyclo(l ‐Val‐l ‐Leu) ( 13 ), cyclo(l ‐Ile‐l ‐Ile) ( 14 ), cyclo(l ‐Tyr‐l ‐Tyr) ( 15 ), turnagainolide A ( 16 ), and bacimethrin ( 17 ) were isolated from the fermentation broth of Streptomyces rutgersensis T009 obtained from Elaphodus davidianus excrement. Their structures were identified on the basis of spectroscopic analysis. Meanwhile, the absolute configurations of the amino acid residues of compounds 1 and 2 were determined by advanced Marfey method. Compound 3 was obtained from a natural source for the first time. The X‐ray single crystal diffraction data of bacimethrin ( 17 ) were also reported for the first time. Compounds 1  –  17 exhibited no antimicrobial activities with the MICs > 100 μg/ml.     

Sesquiterpenoids from the Fruits of Alpinia oxyphylla and Their Anti‐Acetylcholinesterase Activity

Fourteen sesquiterpenoids were isolated from the fruits of Alpinia oxyphylla Miq . Their structures were elucidated based on NMR analyses (¹H, ¹³C, DEPT, ¹H,¹H‐COSY, HMQC, HMBC, and NOESY) and identified as 12‐nornootkaton‐6‐en‐11‐one ( 3 ), (+)‐(3S,4aS,5R)‐2,3,4,4a,5,6‐hexahydro‐3‐isopropenyl‐4a,5‐dimethyl‐1,7‐naphthoquinone ( 5 ), nootkatene ( 6 ), 9β‐hydroxynootkatone ( 7 ), 2β‐hydroxy‐δ‐cadinol ( 8 ), 4‐isopropyl‐6‐methyl‐1‐tetralone ( 11 ), oxyphyllone E ( 12 ), oxyphyllone D ( 13 ), oxyphyllanene B ( 15 ), oxyphyllone A ( 16 ), oxyphyllol E ( 17 ), (9E)‐humulene‐2,3;6,7‐diepoxide ( 18 ), mustakone ( 20 ), and pubescone ( 21 ). Among them, 3 was a new norsesquiterpenoid, 8 was a new natural product, and 5, 6, 11, 20, 21 were isolated from A. oxyphylla for the first time. Twenty sesquiterpenoids, 1 – 5 and 7 – 21 , were investigated for their in vitro acetylcholinesterase (AChE) inhibitory activities, including previously isolated seven sesquiterpenoids from A. oxyphylla, (11S)‐12‐chloronootkaton‐11‐ol ( 1 ), (11R)‐12‐chloronootkaton‐11‐ol ( 2 ), nootkatone ( 4 ), oxyphyllenodiol A ( 9 ), oxyphyllenodiol B ( 10 ), 7‐epiteucrenone B ( 14 ), and alpinenone ( 19 ). TLC‐Bioautographic assay indicated that 1 – 4, 7, 14, 16, 18, 19 , and 21 displayed anti‐AChE activities at 10 nmol. Microplate assay confirmed that 19, 18, 16 , and 21 displayed moderate‐to‐weak anti‐AChE activities at the concentration of 100 μM , and 19 was the most potent inhibitor with an IC₅₀ value of 81.6±3.5 μM . The presence of anti‐AChE sesquiterpenoids in A. oxyphylla may partially support the traditional use of this fruit for the treatment of dementia.     

(+)‐N‐Formylnorglaucine Rotamers from Unonopsis stipitata Diels

(+)‐N‐formylnorglaucine ( 1 ), an aporphine alkaloid containing a formyl group linked to the heterocyclic nitrogen, was isolated from the leaves of Unonopsis stipitata, an Amazon medicinal plant. The chemical structure was characterized based on 1D‐ and 2D‐NMR spectroscopy and HR‐ESI‐MS. NMR spectra revealed that 1 is composed of two rotamers ( 1a and 1b ) in a ratio of approximately 2:1. In addition, the fragmentation behavior of 1 displayed an unusual fragmentation pattern compared to regular aporphine alkaloids. Thus, this compound is reported for the first time as a natural product in this study.     

Synthesis and Biological Activity of a Series of Novel N‐Substituted β‐Lactams Derived from Natural Gallic Acid

A series of novel β‐lactams derived from natural gallic acid were conveniently synthesized via classical Staudinger ketene‐imine cycloaddition reaction. Their structures were confirmed by satisfactory analytical and spectroscopic methods. The preliminary bioassay showed that some of the target compounds exhibited obvious insecticidal activity against Heliothis armigera at the dosage of 0.2 mg/mL.     

Microwave‐assisted Synthesis of Novel 3,4‐Bis‐chalcone‐N‐arylpyrazoles and Their Anti‐inflammatory Activity

A series of 3,4‐bis‐chalcone‐N‐arylpyrazoles 3a‐h was prepared conveniently from diacetyl pyrazoles 2a,b . All reactions were carried out under conventional thermal heating and/or microwave irradiation. The structure of the latter functionally pyrazoles was confirmed under the bases of their IR, mass, ¹H NMR and ¹³C NMR. The X‐ray diffraction of compound 3e not only confirmed the chemical structure of 3a‐h , but also showed the E configuration of their chalcone moieties. Treatment of compound 3e with phenyl hydrazine in presence of acetic acid afforded the tri‐pyrazle 4 . The anti‐inflammatory activity of the newly synthesized compounds was investigated. Some of these compounds showed a moderate activity when compared with indomethacin as a reference drug. The combination between chalcone and pyrazole moieties revealed a variable effect in anti‐inflammatory activity.     

Retraction: A New Sesquiterpene from Caragana intermediia and Its Anti‐Pyricularia oryzae P‐2b Activity

The following article from Chinese Journal of Chemistry , 'A New Sesquiterpene from Caragana intermediia and Its Anti–Pyricularia oryzae P–2b Activity' by Zhi–Hua Sun, Chang–Qi Hu, and Jin–Yi Wang, published online on May 15, 2008 in Wiley Online Library, and in print Volume 26 Issue 5, 2008, pages 831–834, has been retracted by agreement between the authors, the journal Editor in Chief, Prof. Guozhen Ji, and Wiley–VCH Verlag GmbH & Co. KGaA. The retraction has been agreed due to overlap between this article and the following article published in Chinese Chemical Letters , 'A new sesquiterpene from Caragana intermediia' by the same authors, Volume 18 Issue 11, 2007, pages 1379–1382.