Cytotoxic diaporindene and tenellone derivatives from the fungus Phomopsis lithocarpus / 中国天然药物

Nine new compounds, including five natural rarely-occurring 2, 3-dihydro-1H-indene derivatives named diaporindenes E-I (1-5), and four new benzophenone analogues named tenellones J-M (6-9) were isolated from the deep-sea sediment-derived fungus Phomopsis lithocarpus FS508. All the structures for these new compounds were fully characterized on the basis of spectroscopic data, NMR spectra, and ECD calculation and single-crystal X-ray diffraction analysis. The potential anti-tumor activities of compounds 1-9 against four tumor cell lines SF-268, MCF-7, HepG-2, and A549 were evaluated using the SRB method. Compound 7 exhibited cytotoxic activity against the SF-268 cell line with an IC

Antipromastigote and cytotoxic activities of some chemical constituents of Hypericum lanceolatum Lam. (Guttifereae)

Phytochemical investigation of the ethanol extract of the stem bark of Hypericum lanceolatum Lam. (Guttifereae)afforded eight known compounds including 2,2ʹ,5,6ʹ-tetrahydroxybenzophenone (1), 5-hydroxy-3-methoxyxanthone(2), 3-hydroxy-5-methoxyxanthone (3), betulinic acid (4), hydroquinone (5) 6,7-dihydroxy-1,3-dimethoxyxanthone(6), calophyllumin A (7), and 1,3,5,6-tetrahydroxy-4-prenylxanthone (8). Compound 1 was submitted to acetylationreaction to give 5-acetoxy-2,2ʹ,6ʹ-trihydroxybenzophenone (9), a new hemisynthetic derivative. Compounds 5 and8 were isolated for the first time from this plant. The structures were established by extensive analysis of their massspectrometry and nuclear magnetic resonance (NMR) spectroscopic data and comparison with those from the literature.The isolated compounds (1, 2, 4, 5, and 8) and the derivative of benzophenone (9) were tested for their antipromastigoteand cytotoxic activities against visceral leishmaniasis parasite Leishmania donovani and macrophage RAW 264.7 cellline, respectively. Compound 9 was the most active with an IC50 value of 6.1 µg/ml, while compounds 1, 2, 4, and 8were moderately active with IC50 values ranging from 11.4 to 34.8 µg/ml against L. donovani and were not cytotoxicexcept compound 5 that was very toxic and not active. The findings of the present study suggested that compounds 1,2, 4, and 8 could be considered as a potential source of therapeutic medicine for the treatment of leishmaniasis.

Chemical constituents from pericarps of Aquilaria yunnanensis / 中草药

Objective: To investigate the chemical constituents from the pericarps of Aquilaria yunnanensis. Methods: The chemical constituents were separated and purified by silica gel, Sephadex LH-20 column chromatography, and semi-preparative HPLC. The structures of isolated compounds were identified by physicochemical properties and spectroscopic data. Results: Thirteen compounds were isolated from the ethyl acetate layer of 95% EtOH extract of the pericarps of A. yunnanensis, and identified as trans-linalool-3,6-oxide-7-O-β-D-(6'-O-acetyl)-glucoside (1), phenethyl-8-O-β-D-(6'-O-acetyl)-glucoside (2), mangiferin (3), iriflophenone-3,5-C-β-D-diglucoside (4), kaempferol-3-O-β-D-glucoside (5), luteolin-7-O-β-D-glucoside (6), isorhamnetin-3-O-β-D- glucoside (7), kaempferol-3-O-β-D-(6″-p-coumaroyl)-β-D-glucoside (8), geraniol-1-O-β-D-glucoside (9), 3-[2-formyl-5- (hydroxymethyl)-1H-pyrrol-1-yl] pentanedioic acid (10), cannabisin D (11), icariside D2 (12), and coniferin (13). Conclusion: Compound 1 is a new compound and compound 2 is a new natural product. Compounds 7, 9-13 were obtained from the Aquilaria genus for the first time. All compounds were firstly isolated from A. yunnanensis.

Multiple target fishing hook prepared by photochemically coupling molecules in medicines onto magnetic nanoparticles / 中草药

Objective: To achieve multiple target fishing hook by efficiently grafting polymers containing benzophenone (BP) groups and photochemically coupling molecules in medicines onto magnetic nanoparticles (MNPs). Methods: MNPs attached carbonyl groups (Fe3O4-COOH) were prepared through a hydrothermal process. Then they were modified with DMSA, forming MNPs with thiol groups (Fe3O4-SH). Fe3O4-SH nanoparticles were grafted with polymer containing BP groups by surface-initiated condensation polymerization. Effects of monomer feed ratios and contents on the amounts of BP groups were investigated. The molecules in medicines were covalently coupled onto MNPs via photochemical reactions of BP groups. The contents of coupled molecules were determined by FT-IR and UV-Vis spectra analyses. Results: MNPs with average size of 100 nm were produced, modified with DMSA, and decorated by grafting polymer containing photosensitive BP groups. When the content of monomer containing BP groups was increased in grafting polymerizations, more BP groups were incorporated onto MNPs. This was conductive to the subsequent photo- coupling. FT-IR and UV-Vis spectra analyses confirmed the coupling of molecules in medicines. The active H and steric hinderance of the molecules affected their coupling. Conclusion: The resultant magnetic target fishing hook is ready as a probe for targets identification of traditional Chinese medicine (TCM).

Chemical composition by HPLC-ESI-QTOF-MS/MS: Estrogenic and antioxidant effects of Mangifera indica L. cv. "Kent" leave extracts on ovariectomized rats / Composición química por HPLC-ESI-QTOF-MS/MS: efectos estrogénicos y antioxidantes de extractos de Mangifera indica L. cv. "Kent" en ratas ovariectomizadas

The chemical composition of Mangifera indica L. cv. "Kent" leaves was determined by HPLC-ESI-QTOF-MS/MS. Polyphenolic compounds characterized as benzophenone derivatives were the main components found in extracts (1, maclurin 3-C-(2-O-galloyl)-D- glucoside isomer; 2, maclurin 3-C---D-glucoside; 3, iriflophenone 3-C---D-glucoside; 5, maclurin 3-C-(2,3-di-O-galloyl)---D-glucoside; 6, iriflophenone 3-C-(2-O-galloyl)---D-glucoside; 7, methyl-iriflophenone 3-C-(2,6-di-O-galloyl)---D-glucoside) and xanthones (4, mangiferin and 8, 6-O-galloyl-mangiferin). The estrogenic and antioxidant effects of aqueous extracts from Mangifera indica L. cv. "Kent" leaves on ovariectomized rats were determined by uterotrophic assay and malondialdehyde (MDA) levels in erythrocytes, bone, liver, and stomach. We conclude that the polyphenolic compounds from extracts act as exogenous antioxidant agents against oxidative damage in ovariectomized rats.

La composición química de las hojas de Mangifera indica L. cv. "Kent" se determinó por HPLC-ESI-QTOF-MS/MS. Compuestos polifenólicos caracterizados como derivados de benzofenona fueron los componentes principales encontrados en los extractos (1, isómero de la maclurina 3-C-(2-O-galoyil)-D-glucósido; 2, maclurina 3-C-ß-D-glucósido; 3, iriflofenona 3-C-ß-D-glucósido; 5, maclurina 3-C-(2,3-di-O-galloíl)-ß-D-glucósido; 6, iriflofenona 3-C-(2-O-galloil)-ß-D-glucósido; 7, metil-iriflofenona 3-C-(2,6-di-O- galloyl)-ß-D-glucósido) y xantonas (4, mangiferina y 8, 6-O-galoyil-mangiferina). Los efectos estrogénicos y antioxidantes de los extractos acuosos de hojas de Mangifera indica L. cv. "Kent" en ratas ovariectomizadas se determinaron mediante ensayo uterotrófico y la medición de los niveles de malondialdehído (MDA) en eritrocitos, huesos, hígado y estómago. Concluimos que los compuestos polifenólicos de los extractos actúan como agentes antioxidantes exógenos contra el daño oxidativo en ratas ovariectomizadas.

Development and characterization of photoprotective formulations containing keratin particles

This work deals with development and evaluation of MFQ protective formulation, which contains two organic filters, namely: octyl-p-methoxycinnamate (OMC) and benzophenone-3 (BP-3); a photostabilizing agent called ethylhexylmethoxycrylene (EHMCR) and keratin particles. The MFQ formulation was evaluated in order to measure its pH, spin-spin lattice relaxation time (T2H), occlusivity factor, formulation efficacy, photostability and skin permeation, as well as keratin particle properties. Keratin particle size increased when incorporated to formulation, however, it did not affect pH. The MFQ formulation was found to be photostable and photoprotective, as evidenced by sunlight photostability test, sun protection factor (SPF), UVA/UVB ratio and critical wavelength. Interaction between keratin particles and active substances (OMC, BP-3 and EHMCR) was evidenced by T2H measurements. Evidences suggest that keratin reduces the permeation of both UV filters employed along this study, therefore, it can be stated that keratin has a promising potential for use in sunscreen formulations.

Research progress in environmental pollution and endocrine disruption of the UV filter benzophenone-3 / 上海交通大学学报（医学版）

Benzophenone-3 is the most widely used benzophenone type UV filter, which is lipophilic, light stable and bioaccumulative. Benzophenone-3 is widely present in environmental waters and can be detected in humans. Its potential toxicity (especially endocrine disruption) has attracted people's attention. There are a lot of related data on the exposure of benzophenone-3 in the environment and humans from foreign literatures, but there are few studies on related aspects in China. In the view of widespread presence of benzophenone-3 and its endocrine disruption, future researches should focus on its potential toxicity to the population including endocrine disruption and the mechanisms.

Two new compounds from Hypericum sampsonii / 中草药

To study the chemical constituents in the aerial parts of Hypericum sampsonii. Chromatographic methods were used for the isolation and purification. The structures were identified on the basis of spectroscopic analysis. Four compounds were isolated from the 60% ethanol extract in the aerial parts of H. sampsonii. They were identified as 3', 5'-dihydroxy-2, 4, 6-trimethoxylbenzophenone (1), 3'-hydroxy-2, 4, 6-trimethoxylbenzophenone-5'-O-α-L-rhamnopyranoside (2), 2-hydroxy-4, 6-dimethoxylbenzophenone (3), and 2, 4, 6, 3', 5'-pentamethoxylbenzophenone (4). Compounds 1 and 2 are two new benzophenone compounds named sampsine A and sampsine B; Compounds 3 and 4 are isolated from H. sampsonii for the first time.

The effect of 4,4'-bis(N,N-diethylamino) benzophenone on the degree of conversion in liquid photopolymer for dental 3D printing

PURPOSE: The purpose of this preliminary study was to investigate the effects of adding 4,4'-bis(N,N-diethylamino) benzophenone (DEABP) as a co-initiator to a binary photoinitiating system (camphorquinone-amine) to analyze on the degree of conversion (DC) of a light-cured resin for dental 3D printing. MATERIALS AND METHODS: Cylindrical specimens (N=60, n=30 per group, o5 mm x 1 mm) were fabricated using bisphenol A glycerolate dimethacrylate (BisGMA) both with and without DEABP. The freshly mixed resins were exposed to light in a custom-made closed chamber with nine light-emitting diode lamps (wavelength: 405 nm; power: 840 mW/cm2) for polymerization at each incidence of light-irradiation at 10, 30, 60, 180, and 300 seconds, while five specimens at a time were evaluated at each given irradiation point. Fourier-transform infrared (FTIR) spectroscopy was used to measure the DC values of the resins. Two-way analysis of variance and the Duncan post hoc test were used to analyze statistically significant differences between the groups and given times (alpha=.05). RESULTS: In the DEABP-containing resin, the DC values were significantly higher at all points in time (P<.001), and also the initial polymerization velocity was faster than in the DEABP-free resin. CONCLUSION: The addition of DEABP significantly enhanced the DC values and, thus, could potentially become an efficient photoinitiator when combined with a camphorquinone-amine system and may be utilized as a more advanced photopolymerization system for dental 3D printing.

Validação de metodologia analítica para a determinação de benzofenona-3 nanoencapsulada incorporada em creme gel e estudo da estabilidade físico química / Validation of a method to determine content of nanoencapsulated benzophenone-3 incorporated in a gel cream and study of its physical and chemical stability

The aim of this research was to develop and validatean ultraviolet spectrophotometric method for thequantitative analysis of the content of benzophenone-3(BZ3) nanoencapsulated and incorporated in gel creamand to carry out a study of its stability and determine itsshelf life. The validated method was selective and linearin the range 2?20 ?g/mL, with a correlation coefficientof (r) of 0.999996, precise (relative SD < 2.44%), exact(98.8% - 100.3%) and robust. It can, therefore be usedin the analysis of nanoencapsulated BZ3 gel cream.Gel creams containing nanoencapsulated and free BZ3showed no significant alterations in appearance, colour,smell, pH, viscosity or spreadability, within the 180 dayperiod during which they were exposed to a controlledtemperature of 40 ºC and relative humidity of 75%. Inboth formulations, the BZ3 content fell, but in the freeform it was degraded more quickly (30 days) than inthe nanoencapsulated form (150 days). This indicatesthat the nanocapsules protected the active ingredient.For the gel cream containing the BZ3 nanocapsules, theestimated shelf life was 125 days, and for the free BZ3,69 days.

Este trabalho teve como objetivos validar a metodologia analítica para a quantificação de benzofenona-3 (BZ3) por espectrofotometria na região do ultravioleta, realizar estudo de estabilidade e determinar o prazo de validade deste ativo nanoencapsulado e incorporado em um creme gel. O método validado apresentou-se seletivo, linear na faixa de 2 - 20 ?g/mL, com coeficiente de correlação (R2=0,999993), preciso (DPR < 2,44%), exato (98,8% - 100,3%) e robusto, podendo ser utilizado na quantificação de BZ3 nanoencapsulada em creme gel. Os cremes géis, contendo BZ3 nanoencapsulada e livre não tiveram alterações significativas com relação à aparência, cor, odor, pH, viscosidade e espalhabilidade, durante 180 dias, expostos a temperatura e umidade controlada de 40 ºC e 75% UR. Em ambas as formulações o teor de BZ3 diminuiu, porém, quando na forma livre, o ativo degradou mais rapidamente (30 dias) do que para a forma nanoencapsulada (150 dias), o que nos permite concluir que as nanocápsulas desempenharam um papel de proteção para o ativo. Para o creme gel contendo as nanocápsulas de BZ3 o prazo estimado de validade foi de 125 dias, e para o que continha a BZ3 livre de 69 dias.

Influence of particle size on appearance and in vitro efficacy of sunscreens

Nanotechnology applies to diverse sectors of science. In cosmetic area, investments have strengthened the idea that nanoproducts provide innumerable benefits to consumers. Extreme exposition to solar light can cause undesirable effects, thus, adding UV filters in cosmetic products are often used as prevention. Ethylhexyl methoxycinnamate and benzophenone-3 are UV filters widely used in sunscreen formulations, this UV filters absorb UVB and UVA radiation, respectively. In this study, sunscreen formulations were developed as nano and macroemulsion, but composed by the same raw material. Nanoemulsion was obtained by phase inversion temperature method (PIT). Physical and functional properties were evaluated by visual analysis, particle size distribution and by diffuse reflectance spectrophotometry. Achieved nanoemulsion showed bluish brightness aspect, less apparent consistency than macroemulsion, stability longer than 48 hours (22.0 ± 2.0 °C) and bimodal particle size distribution with average (mean) sizes around 10 nm (61%) and 4.5 µm (39%). Macroemulsion showed milky aspect, higher consistency than nanoemulsion, instability after 48 hours (22.0 ± 2.0 °C) and bimodal particle size distribution with average (mean) size around 202 nm (9%) and 10.4 µm (91%). Effectiveness profile of sunscreen formulations remained apparently similar, based on achieved results of in vitro SPF, UVA/UVB ratio and critical wavelength assays.

A nanotecnologia se aplica a diversos setores da ciência. Na área de cosméticos, os investimentos têm reforçado a idéia de que nanoprodutos oferecem inúmeros benefícios para os consumidores. A exposição excessiva à luz solar pode causar efeitos indesejáveis, logo, a adição de filtros UV em produtos cosméticos é frequentemente usada como prevenção. O p-metoxicinamato de octila e a benzofenona-3 são filtros UV amplamente utilizados em formulações de protecção solar, que absorvem radiações UVB e UVA, respectivamente. Neste estudo, desenvolveram-se formulações de protetores solares na forma de nano e macroemulsão, mas compostos pelas mesmas matérias-primas. A nanoemulsão foi obtida pelo método da temperatura de inversão de fases (PIT). As propriedades físicas e funcionais foram avaliadas por análise visual, distribuição de tamanho de partículas e por espectrofotometria de reflectância difusa. A nanoemulsão obtida apresentou brilho azulado, menor consistência aparente quando comparada `a macroemulsão, estabilidade superior a 48 horas (22,0 ± 2,0 ° C) e distribuição de tamanhos de partícula bimodal, com média (média) de tamanhos ao redor de 10 nm (61%) e 4,5 µm (39%) . A macroemulsão apresentou aspecto leitoso, maior consistência aaprente do que nanoemulsão, instabilidade após 48 horas (22,0 ± 2,0 ºC) e distribuição de tamanhos de partícula bimodal, com média (média) de tamanhos ao redor de 202 nm (9%) e 10,4 µm (91%). O perfil de eficácia das formulações fotoprotetoras permaneceu aparentemente similar, com base em resultados obtidos por ensaios de FPS in vitro, relação UVA/UVB e comprimento de onda crítico.

Flavonoids of Lonchocarpus montanus A.M.G. Azevedo and biological activity

The analysis of root extracts from Lonchocarpus montanus A.M.G. Azevedo resulted in the isolation of twenty three compounds chiefly flavonoids of which five (four flavonoids and one benzophenone) are described for the first time. The molecular structures of the new compounds (1-5) were determined through spectral analysis (UV, IR, MS and NMR) as being: 2'-hydroxy-8-(a,a-dimethylallyl)-2", 2"-dimethylpyrano-(5",6":3',4')-dibenzoylmethane (1), 2'-methoxy-8-(a, a-dimethylallyl)-2", 2"-dimethylpyrano-(5",6":3',4')-dibenzoylmethane (2), 4'-methoxy-2",2"-dimethylpyrano-(5",6":8,7)-flavone (3), 2"-(1-hydroxy-1-methylethyl)-furano-(4",5":8,7)-flavone (4) and [2'-methoxy-furano-(4",5":3',4')-phenyl]-phenylmethanone (5). Additionally, fifteen fatty acids were detected through GC-MS analysis of the corresponding methyl esters [(CH3)2CH(CH2)8COOH and CH3(CH2)nCOOH (n = 6, 12-24)]. Quantitative RP-HPLC showed that the most abundant flavonoids in the petroleum ether and dichloromethane extracts were pongamol (19 percent) and lanceolatine B (8.0 percent), respectively. In the bioautography assay, the extracts, pongamol (9), lanceolatine B (10), isolonchocarpin (14), derriobtusone A (17) and medicarpine (18) were active against Staphilococus aureus whereas 9 also against Bacillus subtilis and Cladosporium cladosporioides. Compound 1, 2",2"-dimethylpyrano-(5",6":8,7)-flavone (11) and furano-(1200,1300:7,8)- 4'-methoxy flavone (12) were active against Fusarium oxysporium whereas 11 also against Rhizopus orizae. The extracts, compounds 9, 10, 17 and (E)-7-O-methoxypongamol (23) displayed high toxicity in the brine shrimp lethality assay.

A análise dos extratos das raízes de L. montanus A.M.G. Azevedo resultou no isolamento de vinte e três compostos principalmente flavonóides dos quais cinco são descritos pela primeira vez. As estruturas moleculares dos novos compostos (1-5) foram propostas através da análise dos espectros de UV, IV, EM e RMN como sendo: 2'-hidroxi-8-(a, a-dimetilalil)-2", 2"-dimetilpirano-(5", 6":3',4')-dibenzoilmetano (1), 2'-metoxi-8-(a,a-dimetilalil)-2", 2"-dimetilpirano-(5", 6":3',4')-dibenzoilmetano (2), 4'-metoxi-2", 2"-dimetilpirano-(5", 6":8,7)-flavona (3), 2"-(1-hidroxi-1-metiletil)-furano-(4", 5":8,7)-flavona (4) e [2'-metoxi-furano(4", 5":3',4')-fenil]-fenilmetanona (5). Adicionalmente quinze ácidos graxos foram detectados através da análise de CG-EM dos ésteres metílicos correspondentes [(CH3)2CH(CH2)8COOH e CH3(CH2)nCOOH (n = 6, 12-24)]. A análise quantitativa por CLAE mostrou que os flavonóides mais abundantes nos extratos éter de petróleo e diclorometânico foram pongamol (19 por cento) e lanceolatina B (8.0 por cento), respectivamente. Nos ensaios de bioautografia, os extratos, pongamol (9), laceolatina B (10), isolonchocarpina (14), derriobtusona A (17) e medicarpina (18) foram ativos contra Staphilococcus aureus enquanto 9, também contra Bacillus subtilis e Cladosporium cladosporióides. O composto 1, 2", 2"-dimetilpirano-(5", 6":8,7)-flavona (11) e furano-(2", 3":7,8)-4'-metoxiflavona (12) foram ativos contra Fusarium oxysporium, enquanto 11, também contra Rhizopus oryzae. Os extratos assim como os compostos 9, 10, 17 e (E)-7-O-metoxipongamol (23) apresentaram alta toxicidade no ensaio de letalidade com Artemia salina.

A Case of Photoallergic Contact Dermatitis due to Benzophenone-3 / 대한피부과학회지

Benzophenones are aromatic ketone derivatives of dibenzoylmethane, exhibiting absorption characteristics not only in the UVC and UVB spectral ranges but also in part of the UVA range, up to 360nm. They are commonly used for extending the spectrum of photoprotection. Benzophenone-3, one of the most popular benzophenones, is the most common cause of sunscreen allergy as well as a substitute of PABA. We report a case of photoallergic contact dermatitis due to benzophenone-3 of sunscreen.

Chemical constituents of Peperomia dindygulensis / 中草药

Objective To study the chemical constituents of Peperomia dindygulensis. Methods Chromatography was used to isolate and purify the chemical constituents, their structures were identified by spectral analyses. Results Eight compounds were isolated and identified as bis-(2-methoxy-4, 5-methylenedioxy)-benzophenone (Ⅰ), peperomin B (Ⅱ), peperomin C (Ⅲ), 5-hydroxy-4′, 7, 8-trimethoxy flavone (Ⅳ), 5-hydroxy-3′, 4′, 7, 8-tetramethoxy flavone (Ⅴ), 5, 3′-dihydroxy-4′, 7, 8-trimethoxy flavone (Ⅵ), ?-sitosterol (Ⅶ), hexadecanoic acid (Ⅷ). Conclusion Compound Ⅰ is a new compound named as dindygulensin. All compounds, except Ⅴ, are isolated from P. dindygulensis for the first time.