Electrospun methacrylated natural/synthetic composite membranes for gingival tissue engineering.

New functional materials for engineering gingival tissue are still in the early stages of development. Materials for such applications must maintain volume and have advantageous mechanical and biological characteristics for tissue regeneration, to be an alternative to autografts, which are the current benchmark of care. In this work, methacrylated gelatin (GelMa) was photocrosslinked with synthetic immunomodulatory methacrylated divinyl urethanes and defined monomers to generate composite scaffolds. Using a factorial design, with the synthetic monomers of a degradable polar/hydrophobic/ionic polyurethane (D-PHI) and GelMa, composite materials were electrospun with polycarbonate urethane (PCNU) and light-cured in-flight. The materials had significantly different relative hydrophilicities, with unique biodegradation profiles associated with specific formulations, thereby providing good guidance to achieving desired mechanical characteristics and scaffold resorption for gingival tissue regeneration. In accelerated esterase/collagenase degradation models, the new materials exhibited an initial rapid weight loss followed by a more gradual rate of degradation. The degradation profile allowed for the early infiltration of human adipose-derived stromal/stem cells, while still enabling the graft's structural integrity to be maintained. In conclusion, the materials provide a promising candidate platform for the regeneration of oral soft tissues, addressing the requirement of viable tissue infiltration while maintaining volume and mechanical integrity. STATEMENT OF SIGNIFICANCE: There is a need for the development of more functional and efficacious materials for the treatment of gingival recession. To address significant limitations in current material formulations, we sought to investigate the development of methacrylated gelatin (GelMa) and oligo-urethane/methacrylate monomer composite materials. A factorial design was used to electrospin four new formulations containing four to five monomers. Synthetic immunomodulatory monomers were crosslinked with GelMa and electrospun with a polycarbonate urethane resulting in unique mechanical properties, and resorption rates which align with the original design criteria for gingival tissue engineering. The materials may have applications in tissue engineering and can be readily manufactured. The findings of this work may help better direct the efforts of tissue engineering and material manufacturing.

Retracing the "Art of Arts and Science of Sciences" from Gregory the Great to Philo of Alexandria.

This study considers the phrase "art of arts and science of sciences," and its variants, in antiquity. Often scholars who note the phrase in a particular ancient author's writing may make reference to another ancient author, but without considering the breadth or depth of its occurrences in antiquity. Beginning with the late sixth-century Gregory the Great's Book of Pastoral Rule, this article retraces the idea through history until reaching Philo of Alexandria. Philo's two uses of the phrase have been neglected in secondary scholarship, and yet his contributions foreshadow the semantic range that will subsequently be seen.

Antifungal 3-butylisocoumarins from Asteraceae-Anthemideae.

Seven new naturally occurring 3-butylisocoumarins were isolated and identified from lipophilic extracts of aerial as well as underground organs: corfin (17) and 3'-hydroxycorfin (18) from the roots of Chamaemelum mixtum and (-)-(R)-2'-methoxydihydroartemidin (5), (+)-(S,R)-epoxyartemidin (6a), dracumerin (12), (+)-(R)-(E)-3'-hydroxyartemidin (13), and capillarin isovalerate (20) from various organs of Artemisia dracunculus (tarragon). Furthermore, six known derivatives, artemidiol (7), (E/Z)-artemidin (11), capillarin (19), artemidinol (21), 8-hydroxyartemidin (22), and 8-hydroxycapillarin (23), were obtained. The antifungal activities of all naturally occurring derivatives were determined in a germ-tube inhibition test against a susceptible strain of rice blast fungus Pyricularia grisea. The 3-butyl side-chain is a prerequisite for high activity. Eleven structurally related synthetic derivatives were additionally tested to explore the influence of structural characteristics on activity. Benlate, blasticidin S, kresoxim-methyl, griseofulvin, and the carrot phytoalexin 6-methoxymellein all served as positive controls.

Antifungal stilbenoids from Stemona collinsae.

Fifteen new stilbenoids including 11 phenylbenzofurans, the stemofurans A-K (1-11), and four dihydrostilbenes, the stilbostemins A (15), C (17), E (19), and F (20), were isolated and identified from a methanolic extract of Stemona collinsae roots together with five known derivatives, the stilbenes pinosylvin (13) and 4'-methylpinosylvin (14), the dihydrostilbenes, stilbostemins B (16) and D (18), and the dihydrophenanthrene racemosol (12) as well as (+)-sesamin, coniferyl alcohol, and stigmasterol. Bioautographic tests with Cladosporium herbarum displayed antifungal activity for stilbenoids of all four structural types. Ten derivatives were tested against five microfungi using the microdilution technique linked with digital image analysis of germ tubes.

Stress induced carbazole phytoalexins in Glycosmis species.

Induced formation of a series of carbazole alkaloids was observed in leaves of Glycosmis parviflora and G. pentaphylla after wounding, UV-irradiation, and particularly after inoculation with the fungus Botrytis cinerea. Chemical variation between different provenances and even individuals of G. parviflora led to an accumulation of different derivatives from which three proved to be undescribed natural products. Their structures were identified by spectroscopic methods and named carbalexins A, B, and C. Bioautographic tests on TLC plates with Cladosporium herbarum exhibited strong antifungal activity for the new carbalexins as well as for the already known 2-hydroxy-3-methylcarbazole, but only weak effects for the pyranocarbazole glycoborinine. Detailed experiments with marked infection areas confirmed the restricted accumulation of carbazole derivatives which could not be detected in non-infected areas of the same leaf. Apart from carbazoles, in some individuals of G. parviflora an additional accumulation of the pyranoquinolones flindersine and methylflindersine was induced, which supports the already previously discussed biogenetic connections between carbazoles and prenylated quinolones.

Insecticidal flavaglines and other compounds from Fijian Aglaia species.

Bioassays with lipophilic crude extracts of four Fijian Aglaia species against Spodoptera littoralis displayed strong insecticidal activity for A. basiphylla and A. gracilis, whereas A. archboldiana and A. vitiensis did not have any significant effects. The insect toxicity of A. basiphylla was caused by the well known benzofuran flavaglines rocaglamide, desmethylrocaglamide and aglafoline. In contrast, A. gracilis contained four related pyrimidinone derivatives in the root and stem bark, including two new congeners named marikarin and 3'-hydroxymarikarin. Moreover, two new putrescine bisamides, secoodorine and secopiriferine, a new benzopyran flavagline. desacetylaglain A. and a new norsesquiterpene were isolated from the leaves together with three known bisamides and 3-hydroxy-5,7,4'-trimethoxyflavone. The structures of the new compounds were elucidated by spectroscopic methods. Comparative feeding assays within the active pyrimidinone flavaglines showed that the free hydroxy group in aromatic ring A of marikarin diminishes insecticidal activity.

Infraspecific variation of sulfur-containing bisamides from Aglaia leptantha.

Six new amides, leptaglin (1), hemileptaglin (2), aglanthin (3), agleptin (4), isoagleptin (5), and leptanthin (6), together with known lignans yangambin, eudesmin, grandisin (7), epigrandisin (8), and dehydrodiconiferyl alcohol, were isolated and identified from the lipophilic leaf and stem bark extracts of Aglaia leptantha. The dominating sulfur-containing bisamides contained either putrescine or the corresponding pyrrolidine ring as the diamine part, linked to phenylacetic and/or methylthiopropenoic acid moieties showing a remarkable infraspecific variation in eight individuals from two different habitats. Structures were determined by MS and NMR, including lanthanide-induced shifts.

Prenylated sulfonyl amides from Glycosmis species.

Nine new sulfur containing amides were isolated from the lipophilic leaf extracts of different varieties of Glycosmis chlorosperma and G. ex aff. pseudoracemosa mainly collected in Thailand. Their structures were elucidated by spectroscopic methods. All amides were shown to be characterized by a methylsulfonylpropenoic acid moiety linked to a p-geranyloxy- or p-prenyloxy-phenethylamide rest. The compounds differ by different states of oxidation (i) at the 2-position of the ethylamine unit, (ii) at the aromatic m-position of phenethylamine, or (iii) at the terminal methyl group of the geranyloxy side chain.

Bisamides, lignans, triterpenes, and insecticidal Cyclopenta[b]benzofurans from Aglaia species.

Twelve new derivatives of bisamides [piriferinol (5), edulimide (7)], lignans [lariciresinol acetat (10)], triterpenes [4-bis-norcycloartane-type triterpenes (11a, 12a+b, 13a+b)], cyclopenta[b]benzofurans [pannellin (15), pannellin 1-O-acetate (16), 3'-methoxypannellin (17)], and an aromatic butyrolactone [aglalactone (18)] were isolated and identified from lipophilic leaf, stem, and root extracts of Aglaia spp. elaeagnoidea, edulis, grandis, silvestris, and tomentosa. Two cyclopenta[b]benzofurans (flavaglines), pannellin (15) and pannellin 1-O-acetate (16), displayed very strong insecticidal activity against Spodoptera littoralis and Lymantria dispar, comparable with the activity of azadirachtin.

Prenylated phenylpropenes from Coleonema pulchellum with antimicrobial activity.

The lipophilic root extract of Coleonema pulchellum was analysed and tested for antifungal and antibacterial activity. Eight previously undescribed prenyloxy and geranyloxy phenylpropenes, were isolated as major compounds together with the known evofolin-C as well as the lignans (+/-)-sesamin and (+/-)-prenylpiperitol, the diterpene (-)-pimara-9(11),15-dien-19-oic acid and the 2,4-decadienoic acid isobutylamide. All structures were established by spectroscopic evidence. From the new phenylpropenes, named evofolin-C-acetate, colenemol, colenemal, prenycol acetate, dehydroprenycol acetate, precolpuchol, colpuchol and colpuchol acetate, the dihydroxylated precolpuchol displayed the strongest antifungal and antibacterial activity against Cladosporium herbarum and Staphylococcus aureus, respectively.

Bioactive amides from Glycosmis species.

Besides the known imide ritigalin (9), six new phenethyl/styrylamine-derived amides isolated from lipophilic leaf extracts of Glycosmis cf. mauritiana, Glycosmis cf. cyanocarpa, and Glycosmis crassifolia displayed pronounced antifungal and/or insecticidal activity against Cladosporium herbarum and Spodoptera littoralis, respectively, the methylthiocarbonic acid derivatives niranin (1), dehydroniranin A (2), and dehydroniranin B (3) as well as the isovaleric and senecioic acid derivatives thalebanin B (4), dehydrothalebanin B (5), and dehydrothalebanin A (6).

[Absolute configuration and enantiomeric purity of celiprolol]. / Absolute Konfiguration und enantiomere Reinheit von Celiprolol.

The absolute configuration of (+)-celiprolol ([alpha]D = +6.3 degrees in CHCl3) was established by a 9-step synthesis via the (+) (R)-acetonide of (R)-glyceraldehyde. This result was confirmed by the Cupra-A CD-spectra of the isopropyl and hydroxy analogs. The enantiomeric purity was determined by NMR analysis of the diastereomeric amide esters obtained by reaction of celiprolol with 2 mol of alpha-methoxy-alpha-trifluoromethyl-phenylacetic acid chloride (Mosher's reagent).