bluuebunny/crossref_metadata_2025 huggingface dataset:
With Guide of Spike-in Experiment for Optimizing Workflow of LC-MS data Processing in Metabolomics
Authors: Yan Bing-Peng , Cao Chun-Mei , Hou Jin-Jun , Bi Qi-Rui , Yang Min , Qi Peng , Shi Xiao-Jian , Wang Jian-Wei , Wu Wan-Ying , Guo De-An
Published: March 2019

A systematical study was performed to investigate the processing workflow of LC-MS-based metabolomics data by optimizing parameter settings in XCMS software and comparing different preprocessing methods. Here we use a spike-in experiment combining with design of experiment (DoE) approaches for optimizing XCMS software parameters. A trusted index, which was based on accuracy evaluation of the spike-in data, was employed to assess the optimizing process. After optimizing the XCMS setting, the trusted index was improved from 3.67 to 30 and positive rate of spike-in standards also increased from 20% to 100%. Moreover, different data preprocessing methods, such as normalization, different scaling methods were also investigated on spike-in data since they were found to affect the outcome of the data analysis and ions features identification. Accordingly, UN-normalization and Pareto scaling were chosen as appropriate preprocessing methods to deal with LC-MS data through the evaluation of match index (mainly applied multivariate statistics methods). Finally, the optimized workflow was applied to experimental samples that acquired from metabolomics experiment and analyzed randomly with spike-in sample, which indicated a better applicability in formal metabolomics experiment. It is concluded that the proposed data processing workflow could be used as feasible approach for improving the quality of LC-MS-based metabolomics data and ensured the veracity of metabolites identification in data processing procedures to a certain extent.
Essential Oil Composition of Two Sphagnum Species Grown in Portugal and their In Vitro Culture Establishment
Authors: Sim-Sim Manuela , Abreu Margarida , Garcia César , Sérgio Cecília , Figueiredo A. Cristina
Published: March 2019

Two peat moss species, frequent both in the mainland Portugal and in the Azores archipelago, were evaluated for essential oil composition and establishment under in vitro culture. Sphagnum auriculatum and Sphagnum subnitens essential oils were isolated by hydrodistillation and analysed by Gas Chromatography (GC) and Gas Chromatography-Mass Spectrometry (GC-MS). The essential oil of S. auriculatum was dominated by an as yet unidentified sesquiterpene, whereas zierene was the main component of S. subnitens essential oil. The in vitro cultures were successfully established for future studies of their chemical profile. The components present in essential oils obtained from S. auriculatum and S. subnitens together with morphological traits could be used to support the taxonomy of this plant group.
A Mobile Laboratory System for the Rapid Field Analysis of Aromatic Plants
Authors: Slacanin Ivan , Rey Charles , Rey Sabine
Published: March 2019

A novel mobile laboratory device integrating miniaturized extraction and GC / FID systems has been developed and applied for the field analysis of wild thyme at the flowering stage. This convenient device provides analytical results within 10 minutes (i.e. 1 min for extraction plus 9 min for full GC/FID analysis) using only a 100-mg aliquot of fresh plants. This mobile laboratory is suitable for field analysis allowing the rapid selection in situ of the most promising plants chemotypes to use for subsequent agro-botanical works.
The Isolation, Structure Elucidation, and Bio- and Total Synthesis of Bis-bibenzyls, from Liverworts and Their Biological Activity
Authors: Asakawa Yoshinori
Published: March 2019

Little attention has been paid to the bryophytes for use in the human diet in spite of the presence of 23,000 species in the world. Some liverworts produce lipophilic terpenoids and phenolic bis-bibenzyls, possessing antimicrobial, antifungal, antiviral, cytotoxic, anti-oxidant, muscle relaxing, and antiobesity activities. In this review, the isolation, structures elucidation, bio- and total syntheses of bis-bibenzyls from several liverworts are discussed.
Synthesis of Deuterium-Labeled Steroid 3,6-Diols
Authors: Ivanchina Natalia V. , Gorbach Vladimir I. , Kalinovsky Anatoly I. , Kicha Alla A. , Malyarenko Timofey V. , Dmitrenok Pavel S. , Stonik Valentin A.
Published: March 2019

A facile synthesis of a set of deuterium-labeled steroid 3,6-diols with different steroid A/B ring fusion, unsaturations, and configurations of hydroxyl groups at C-3 and C-6 is described. Reduction and deuteration, based on deuterium-exchange of the obtained the cholest-4-ene-3,6-dione from cholesterol using sodium borodeuteride and deuterium water, were used. The obtained steroid diols are intended to be used as precursors in the studies on biosynthesis of some marine polar steroids.
Berberine Inhibited the Proliferation of Cancer Cells by Suppressing the Activity of Tumor Pyruvate Kinase M2
Authors: Li Zhichao , Li Hanqing , Lu Yangxu , Yang Peng , Li Zhuoyu
Published: March 2019

Berberine, an isoquinoline alkaloid extracted from coptis, exerts anti-proliferation and anticancer properties. Pyruvate kinase M2 (PKM2) is a key enzyme of aerobic glycolysis and considered as the potential anticancer target. However, the inhibition effects and interaction action between Berberine and PKM2 is not well known. In this study, berberine showed antitumor activity of HCT-116 and HeLa cells with the suppression of cell proliferation. Moreover, berberine inhibited the enzyme activity of PKM2 in cancer cells, but had no impact on PKM2 expression. Further research showed that the interaction between berberine and PKM2 was dynamic fluorescence quenching and the main intermolecular force was hydrogen bonding. These findings revealed that berberine may serve as a therapeutic drug for cancer chemotherapy.
Rothtalazepane, A New Azepane from the Wood of Rothmannia talbotii (Rubiaceae)
Authors: Koagne Romeol Romain , Bitchagno Gabin Thierry M. , Fobofou Serge Alain T. , Konga Ingrid Simo , de Dieu Tamokou Jean , Wessjohann Ludger A. , Tane Pierre
Published: March 2019

Rothmannia talbotii, a hitherto chemically unexplored medicinal plant, is used in the Western Region of Cameroon to relieve fever. In our ongoing search for bioactive compounds from Cameroonian medicinal plants, a previously undescribed compound rothtalazepane (1), along with six known compounds, aitchisonide B (2), D-mannitol (3), β-D-glucopyranosyl-(6→1’)-β-D-glucopyranoside (4), monopalmitin (5), stigmasterol (6), and sitosterol 3- O-β-D-glucopyranoside (7) were isolated and characterized from the crude ethanol extract of the wood of R. talbotii. Rothtalazepane (1) exhibits no significant activity against several microbial strains, thus its function likely lies not in antimicrobial defense and it is not the active principle against urinary infections described for Rothmannia.
Influence of Aaptamine Alkaloids on the Growth of Seedling Roots of Agricultural Plants
Authors: Utkina Natalia K. , Chaikina Elena L. , Anisimov Mikhail M.
Published: March 2019

The effect of spongean alkaloids aaptamine (1), isoaaptamine (2), 9-demethylaaptamine (3), aaptanone (4), N-demethylaaptanone (5), and semisynthetic 4- N-methylaaptanone (6) was studied on the growth of seedlings roots of soy { Glycine max (L.) Merr.}, maize ( Zea mays L.), wheat ( Triticum aestivum L.), buckwheat ( Fagopyrum esculentum Moench), and barley ( Hordeum vulgare L.). It was shown that a stimulatory effect depends on the chemical structure of the compounds and species of crop plants. The structural motif of aaptamines 1–3 is essential for a stimulating activity on the growth of seedling roots of soy, maize, and wheat. The oxygenated 1,6-naphthyridine core of aaptanones 5 and 6 is important for their growth stimulating activity on barley roots.
TLC Bioautography-guided Isolation and Antimicrobial, Antifungal Effects of 12 Alkaloids from Hylomecon japonica Roots§
Authors: Xue Xuanji , Zhang Hui , Zhang Xinxin , Liu Xia , Xi Ke , Han Yanxia , Guo Zengjun
Published: March 2019

Hylomecon japonica (Thunb.) Prantl. is a Chinese medicinal plant whose active components and their antimicrobial mechanism was studied by TLC bioautography-guided isolation and identification of 12 alkaloids and their antimicrobial activities evaluated using the standard broth microdilution method. The benzophenanthridine isoquinoline alkaloids showed the strongest inhibitory activity against Gram-positive bacteria. Analysis of conductivity changes and observation of TEM images revealed that the antimicrobial mechanism involved cell integrity damage and cell division arrest.
A New Flavonol Glycoside from Millettia pachycarpa
Authors: Kang Yunyao , Tu Yanbei , Meng Xuefei , Li Qin , Zhu Chao , Li Yanfang
Published: March 2019

Eight compounds (1-8), including a new flavonol glycoside (1), were isolated from Millettia pachycarpa. Their structures were elucidated based on combination of spectroscopic methods and comparing with data in literatures. Three of them (2, 6 and 8) were obtained from this genus for the first time. Meanwhile, this is also the first time compound 5 has been found from nature. Biological evaluation of all isolates against two cholinesterases (ChEs) is also described.
Environmental Factors do not Affect the Phenolic Profile of Hypericum perforatum Growing Wild in Bosnia and Herzegovina
Authors: Zeljković Sanja Ćavar , Karalija Erna , Parić Adisa , Muratović Edina , Tarkowski Petr
Published: March 2019

Using appropriate isolation and fractionation procedure, and UHPLC-MS/MS as powerful analytical tool, comprehensive phenolic acid profile of leaves and flowers of Hypericum perforatum L., growing wild in Bosnia and Herzegovina, has been analyzed for the first time. The phenolic acids were isolated from plant tissue, liberated from esters and glycosidic bonds, and then analyzed as free acids. Results show that free forms of caffeic and chlorogenic acid were the most abundant. Generally, the content of acids is higher in flowers than in leaves, but environmental factors do not significantly influence chemical composition of this medicinal plant.
Quantitative Analysis and Pharmacological Effects of Artemisia ludoviciana Aqueous Extract and Compounds
Authors: Rivero-Cruz Isabel , Anaya-Eugenio Gerardo , Pérez-Vásquez Araceli , Martínez Ana Laura , Mata Rachel
Published: March 2019

Artemisia ludoviciana Nutt. (Asteraceae) is widely used in Mexican folk medicine for treating inflammation, diabetes and painful complaints. The in vivo antinociceptive, antiinflammatory and antihyperalgesic activities of an aqueous extract (AE) of the plant were investigated using well-known animal models. AE reduced the licking time in the formalin test in healthy and NA-STZ mice; the activity was better during the inflammatory phase; accordingly, it displayed significant antiinflammatory when tested at the same doses using the carrageenan-induced oedema model. AE also produced a significant dose-dependent antinociceptive effect in the hot plate test at 100 and 316 mg/kg (p.o.). Phytochemical analysis of the non-polar fraction of AE resulted in the isolation of two major lactones [achillin (1) and dehydroleucodin (2)], which showed antiinflammatory effect, being 2 the most active at 17.7 mg/kg. A suitable analytical method was successfully developed and validated to quantify 1 and 2. Altogether, these results tend to support the medicinal uses of the plant.
Two New Abietane-type Diterpenes from the Bark of Cryptomeria japonica
Authors: Chang Chi-I , Chen Chien-Chih , Chao Che-Yi , Ko Horng-Huey , Chang Hsun-Shuo , Wang Sheng-Yang , Chen Jih-Jung , Chen Cheng-Chi , Kuo Yueh-Hsiung
Published: March 2019

Phytochemical investigation of the methanol extract of the bark of Cryptomeria japonica has led to the isolation of two new abietane-type diterpenoids, 7a-(2’-butoxyethoxy)deoxocryptojaponol (1) and 7p-(2’-butoxyethoxy)deoxocryptojaponol (2). Their structures were established by means of 1D and 2D NMR spectra and HR-EI-MS, as well as on comparison with the reported data.
A Novel Cytotoxic Physalin from Physalis angulata
Authors: Fan Jia-Jia , Liu Xia , Zheng Xi-Long , Zhao Hai Yu , Xia Huan , Sun Yi
Published: March 2019

Bioassay-guided fractionation from the whole plant of Physalis angulata led to the isolation of a novel physalin, 25-hydroxylisophysalin B (1), together with three megastigmane glucosides (2-4) and eight known physalins (5-12). The structure of compound 1 was elucidated by analysis of spectroscopic data. All of the compounds exhibited cytotoxic activities against MCF-7 human mammary cells and HepG2 human hepatoma cells.
Asymmetric Synthesis of Tetrahydroisoquinoline Alkaloids Using Ellman's Chiral Auxiliary
Authors: Reddy Y. Vikram , Biradar Dhanraj O. , Reddy B. Jagan Mohan , Rathod Aravinda , Himabindu M. , Reddya B. V. Subba
Published: March 2019

Chiral t-butylsulfinamide has been successfully employed for the stereoselective synthesis of 1-benzyl tetrahydroisoquinoline alkaloids. This is the first report on the synthesis of chiral 1-benzyltetrahydroisoquinoline natural products using tert-butylsulfinamide through a haloamide cyclization.
Pseudoalteromone C: A Novel Ubichromenol Derivative from Bacterium Pseudoalteromonas sp. CGH2XX Isolated from the Cultured-type Octocoral Lobophytum crassum
Authors: Chen Yu-Hsin , Chen Wu-Fu , Yang Juan-Cheng , Lu Mei-Chin , Kuo Jimmy , Su Jui-Hsin , Weng Ching-Feng , Wu Yang-Chang , Sung Ping-Jyun
Published: March 2019

A novel ubichromenol derivative, pseudoalteromone C (1), possessing a 9C nor-monoterpenoid moiety was produced from CGH2XX, a Pseudoaltermonas sp. strain that was originally cloned from bacteria communities associated with the cultured-type octocoral Lobophytum crassum. The structure of 1 was elucidated by using spectroscopic methods and comparing the spectroscopic data with those of known related metabolites.
Iridoid glycosides from the Genus Gentiana (Gentianaceae) and their Chemotaxonomic Sense
Authors: Yuan Hao-Yang , Kwaku Osafo Raymond , Pan Hui , Han Jia-Xin , Yang Chong-Ren , Xu Min
Published: March 2019

The genus Gentiana is one of the largest genera in the Gentianaceae family. Many Gentiana species have been scientifically investigated for their chemical constituents and chemotaxonomic sense. To date, more than 500 chemical compounds were isolated from Gentiana plant. Several researchers have reviewed the secondary metabolites and their bioactivities of Gentiana plants. However, a survey on iridoid glycosides and their chemotaxonomic sense of the genus Gentiana are unavailable. Iridoid glycosides are the major chemicals isolated from Gentiana spp., which serve as potential chemotaxonomic markers to differentiate Gentiana species. Herein, the review systematically summarizes the scaffolds of the iridoids reported according to the biosynthetic pathway of natural iridoid glycosides. Furthermore, the taxonomy of Gentiana and chemotaxonomic sense of iridoid glycosides in the genus Gentiana were surveyed.
Hypolaetin-7-O-β-D-xyloside from Juniperus communis Fruits Inhibits Melanogenesis on Zebrafish Pigmentation
Authors: Jeong Eun Ju , Jegal Jonghwan , Chung Ki Wung , Noh Sang Gyun , Chung Hae Young , Nam Youn Hee , Kang Tong Ho , Kim Su-Nam , Yang Min Hye
Published: March 2019

Hypolaetin-7- O-β-D-xyloside (1) is a naturally occurring flavonoid from Juniperus communis fruits. This study aimed to investigate anti-melanogenic effect of hypolaetin-7- O-β-D-xyloside on zebrafish pigmentation. The phenotype-based image analysis suggested that 1 suppressed the zebrafish pigmentation in a concentration-dependent manner (1-400 μM) as a reversible competitive inhibitor against the enzyme tyrosinase. According to the molecular docking simulation, the compound 1 interacted with residues His-263 of tyrosinase via hydrogen bonding. The present study provided direct experimental evidence for skin-lightening effect of 1 in an in vivo zebrafish model. Therapeutic attempts with the 1 might be useful in the management of skin pigmentation-related diseases.
Quantitative Analysis of Various B-ring Unsubstituted and Substituted Flavonoids in Ten Australian Species of Eucalyptus
Authors: Saraf Isha , Marsh Karen J. , Vir Sanjay , Foley William J. , Singh Inder Pal
Published: March 2019

Flavonoids (in particular unsubstituted B ring flavanones) in Eucalyptus foliage play an important role in mediating animal plant interactions, and there is a need for methods to analyse the diverse profiles found in leaves. A simple, high-performance liquid chromatographic (HPLC) method with in-line connected photodiode-array (PDA) detection was developed and validated to identify and quantify nine B-ring unsubstituted and three B-ring substituted flavonoids in ten Australian species of Eucalyptus. Of these, eight compounds were detected and quantified in the crude methanolic extracts of leaves of various Eucalyptus species ( E. sieberi, E. rossii, E. fastigata, E. macrorhyncha, E. fraxinoides, E. agglomerata, E. consideniana, E. pauciflora, E. dives and E. obliqua) based on comparison with the retention times and λmax values of pure compounds. This rapid and sensitive HPLC/PDA method was coupled with electrospray ionization mass spectrometry (HPLC-ESI-MS) for qualitative analysis to corroborate the identification of compounds by HPLC/PDA analysis.
Inhibitory Mechanism of Taxifolin against α-Glucosidase Based on Spectrofluorimetry and Molecular Docking
Authors: Liu Jiang , Wang Xiansheng , Geng Sheng , Liu Benguo , Liang Guizhao
Published: March 2019

The α-glucosidase inhibitory activity and behavior of taxifolin was first investigated by spectrofluorimetry and molecular docking. It was found that taxifolin inhibits α-glucosidase in a competitive manner with the IC50 value of 0.16 mg/mL. The intrinsic fluorescence quenching of α-glucosidase in the presence of taxifolin was observed by the static quenching mechanism. According to the thermodynamic study, the complex of taxifolin and α-glucosidase was maintained by van der Waals and hydrogen bonding. The binding mode provided by molecular docking simulation indicated the existence of hydrogen bonding between taxifolin and the amino acid residues of α-glucosidase (Glu429, Asp 568 and Glu771), which coincided with the result of fluorescence analysis.
Proliferation Effects on Hair Growth of Compounds Isolated from the Bark of Dalbergia oliveri
Authors: Park Seon Ju , Nhiem Nguyen Xuan , Tai Bui Huu , Le Tuan Anh Hoang , Oh Seok Hyun , Sung Jong-Hyuk , Kim Nanyoung , Yoo Guijae , Park Jun Hyung , Kwak Hee Jae , Loan Pham Thanh , Kim Seung Hyun , Van Kiem Phan
Published: March 2019

One new isoflavane, 7,4′-dihydroxy-isoflavanquinone (1), together with ten known compounds (2–11) were isolated from the bark of Dalbergia oliveri Prain. The structures of compounds were determined on the basis of extensive spectroscopic methods, including 1D and 2D NMR and CD spectroscopic data. Using a cell proliferation assay, the isolated compounds were evaluated for their proliferation effects on hair growth. (3 R)-5’-Methoxyvestitol (2) and (6a R,11a R)-3,8-dihydroxy-9-methoxypterocarpan (10) significantly increased the proliferation of immortalized dermal papilla cells (iDPC).
Daidzein Production and HeLa Cytotoxicity of Bituminaria bituminosa Hairy Root Cultures
Authors: D'Angiolillo Francesca , Noccioli Cecilia , Ruffoni Barbara , Scarpato Roberto , Pistelli Luisa , Pistelli Laura
Published: March 2019

Bituminaria bituminosa (L.) C.H. Stirt is a perennial species widely distributed in the Mediterranean basin and the Canary Islands. This species is used in folk medicine and currently has considerable pharmaceutical interest for its content in phenylpropanoids, furanocoumarins and pterocarpans. In vitro cultures (shoots and hairy roots) have been performed to obtain plant material useful for the production of these metabolites. Hairy root cultures were successfully established after inoculation of hypocotyls with the LBA 9402 A. rhizogenes strain. The HRPB3 line was selected for further analysis and elicited with chitosan and salicylic acid. All the HRPB3 cultures showed higher polyphenol content and greater DPPH-antioxidant activity than shoots cultured in vitro. The presence of isoflavone daidzein was detected in the hairy root extracts. The cytotoxic effect of HR extracts has been further tested on HeLa cells: the salicylic acid elicited HR exhibited good antiproliferative effects.
Biotransformation of 4-Chromanol, 4-Flavanol, Xanthydrol, and their Analogs by Tissue Cultured Cells
Authors: Nagaki Masahiko , Kikuchi You , Maekawa Shingo , Kidachi Takumi , Honda Kazushige , Chounan Yukiyasu
Published: March 2019

We conducted the biotransformation of 4-chromanol, 4-flavanol and xanthydrol using Italian parsley ( Petroselinum neapolitanum) callus or soybean ( Glycine max) callus as biocatalysts. The biotransformation of 4-chromanol using P. neapolitanum yielded 4-chromanone at 5% on day 3, 12% on day 5, 23% on day 8, 21% on day 11, 25% on day 14, 22% on day 17, and a final yield of 22% on day 20. Although the reaction appeared to level off between days 8 and 20, we verified that the oxidation reaction continued to progress, albeit very gradually, until day 20. Furthermore, biotransformation of 4-flavanol using G. max callus yielded flavanone at 24.8% after 70 days. Moreover, biotransformation of xanthydrol using G. max yielded xanthone at 19.8% on day 1, 72.8% on day 2, 93.1% on day 4, and 96.3% on day 6. Addition of NADP accelerated the reaction, suggesting that an oxidoreductase may be involved. In contrast, there were no observable reverse reactions for 4-chromanone, 4-flavanone, or xanthone using the respective biocatalysts. Therefore, callus cells can be used as biocatalysts for the oxidation of alcohols to ketones. Organic synthetic reactions mimic environmentally-friendly reactions using biocatalysts found in nature.
Highly Cytotoxic Xanthones from Cratoxylum cochinchinense Collected in Myanmar
Authors: Thu Zaw Min , Aung Hnin Thanda , Sein Myint Myint , Maggiolini Marcello , Lappano Rosamaria , Vidari Giovanni
Published: March 2019

Eight xanthones and one anthraquinone, together with four common triterpenoids, have been isolated from the barks of Cratoxylum cochinchinense, collected in Myanmar. The structures of the metabolites were elucidated by spectroscopic data analysis and their antiproliferative activities were measured against six human tumor cell lines, by using the MTT assay. Pruniflorone N (1) showed a significant cytotoxicity against all cancer cells with IC50 values in the range 3-9 μM, on average higher than the anticancer drug cisplatin. Instead, compounds 2 and 3 exhibited high antiproliferative activity against some specific cell lines.
Self-Nanoemulsifying System in the Accumulation of Resveratrol and N- Acetylcysteine in the Epidermis and Dermis
Authors: Laneri Sonia , Sacchi Antonia , Fratter Andrea , Bertin Walter , Bino Alessia , Vertuani Silvia , Manfredini Stefano
Published: March 2019

Trans-resveratrol (RES) and N-acetylcysteine (NAC) have protective effects on biological processes; therefore, they are frequently included in food supplements. Their possible applications for the prevention of free radical-induced damage to the skin are of particular physiological relevance; however, their usefulness is limited by their metabolic fate and the unpredictability of their delivery to the skin following oral administration. In this work, we evaluated the concomitant and direct application of RES and NAC on the skin using a self-nanoemulsifying system we previously developed for the oral delivery of poorly absorbed food supplements. We evaluated the capability of this system to increase RES and NAC accumulation in porcine skin using permeation studies in Franz diffusion cells. The ascorbyl palmitate (ASP) self-nanoemulsifying system considerably increased RES and NAC accumulation in the epidermis and dermis, which peaked 6 h after application. This study reveals a new formulation strategy to improve the bioavailability of ingredients, which was previously used in the health supplements field, but has rarely been employed in dermatology because of its poor distribution in the skin.
Bioactive Secondary Metabolites from the Aerial Parts of Buddleja macrostachya
Authors: Hien Truong Thi Thu , Quang Tran Hong , Nhiem Nguyen Xuan , Tai Bui Huu , Yen Pham Hai , Yen Duong Thi Hai , Ngan Nguyen Thi Thanh , Kim Youn-Chul , Oh Hyuncheol , Van Minh Chau , Van Kiem Phan
Published: March 2019

A new iridoid glycoside, buddlemacroside A (1) and 15 known compounds, including 6-α-L-(4″- O-trans-p-coumaroyl)rhamnopyranosylcatalpol (2), 6-α-L-(2″-caffeoyl)rhamnopyranosylcatalpol (3), salidroside (4), echipuroside A (5), darendoside A (6), decaffeoylacteoside (7), acteoside (8), martynoside (9), 8-hydroxylinalool 3- O-β-D-glucopyranoside (10), 9- O-α-L-rhamnopyranosyl-4-hydroxy-cinnamic acid (11), apigenin (12), acacetin-7- O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (13), mimengoside C (14), buddlejasaponin Ia (15), and buddejasaponin I (16) were isolated from a methanol extract of the aerial parts of Buddleja macrostachya Benth. Their chemical structures were elucidated by extensive spectroscopic analyses, including MS and NMR spectra as well as by comparison with the data reported in the literature. 2,2-Diphenyl-1-picrylhydrazyl (DPPH) radical scavenging test showed that compounds 3 and 7-9 possess significant scavenging capacity, with SC50 values ranging from 6.9-19.6 μM. Compound 8 was shown to have potent inhibitory effect against the release of malondialdehyde (MDA) - the major product of the cellular lipid peroxidation, with IC50 value of 2.3 μM. Compounds 12 and 16 significantly inhibited nitrite production in LPS-stimulated BV2 microglia, with IC50 values of 14.2 and 11.4 μM, respectively. Furthermore, compound 16 showed cytotoxicity toward three human cancer cell lines, including SK-LU-1, MCF7, HepG2, with IC50 values in the range of 6.5-8.0 μM.
A New Picrotoxane Sesquiterpene Glucoside from Dendrobium nobile
Authors: Thanh Nguyen Thi Viet , Ly Giang Thi Phu'o'ng , Tram Le Huyen , Tai Bui Huu , Huy Vu Quoc , Vu Kiem Phan
Published: March 2019

A new picrotoxane sesquiterpene glucoside, dendrobinoside A (1), and three known secondary metabolites dendronobilin G (2), dendromoniliside D (3), massonside A (4) were isolated from the stems of Dendrobium nobile Lindl.. Their chemical structures were elucidated on the basis of HR-ESI-MS, NMR spectroscopic data and comparison with reported values. Chemical structure of new compound was further investigated via its aglycone by enzymatic hydrolysis.
Sessilifol A and B, Urease Inhibitory Pimarane-type Diterpenes from Hymenocrater sessilifolius
Authors: Khan Sadia , Ali Muhammad Shaiq , Ahmed Zeeshan , Lateef Mehreen , Yousuf Sammer , Ahmad Viqar Uddin , Fatima Itrat , Tareen Rasool Bakhsh
Published: March 2019

New pimarane type diterpenes named sessilifol A (1) and B (2) have been isolated from the EtOH soluble fraction of Hymenocrater sessilifolius Benth., along with eight known constituents cirsimaritin (3), gardenin C (4), β-sitosterol (5), saringosterol (6), β-sitosterol glucoside (7), ursolic acid (8), sucrose (9) and vanillic acid (10). Their structures were elucidated on the basis of 1H- and 13C-NMR spectra and by 2D-NMR experiments. The structure of 1 was further confirmed by single crystal X-ray diffraction technique. The compound 2 showed potent inhibitory potential against the enzyme urease while 1, 3, 4 and 10 were moderately active.
Structural Analogues of Lanosterol from Marine Organisms of the Class Asteroidea as Potential Inhibitors of Human and Candida albicans Lanosterol 14α-demethylases
Authors: Kaluzhskiy Leonid A. , Shkel Tatsiana V. , Ivanchina Natalia V. , Kicha Alla A. , Grabovec Irina P. , Gilep Andrei A. , Strushkevich Natallia V. , Chernovetsky Mikhail A. , Medvedev Alexei E. , Usanov Sergey A. , Ivanov Alexis S.
Published: March 2019

Lanosterol 14α-demethylases (hemoproteins of the cytochrome P450(51) family) are involved in biosynthesis of different membrane sterols, including animal cholesterol, fungal ergosterol and C24-modified plant and protozoa sterols. In this study we have investigated 10 structural analogs of lanosterol isolated from echinoderms belonging to the class Asteroidea as potential ligands (competitive inhibitors) of human and Candida albicans cytochromes P450(51). The study was performed using the surface plasmon resonance method, spectrophotometric titration and enzyme assay. Among the compounds tested we found several selective ligands for human and Candida albicans cytochromes. Between selective ligands of the human lanosterol 14α-demethylase we found two novel inhibitors of this enzyme: henricioside H1 and levisculoside G from Henricia derjugini. With due consideration of obtained data, we conclude that marine organisms from the class Asteroidea can be a valuable source of new lead compounds for creation of selective inhibitors of cytochromes P450(51) family with less side effects due to their selective action on these enzymes in different types of organisms.
Phytochemical Profile and Antibacterial Activity of Retama raetam and R. sphaerocarpa cladodes from Algeria
Authors: Hammouche-Mokrane Nawal , León-González Antonio J. , Navarro Inmaculada , Boulila Farida , Benallaoua Said , Martín-Cordero Carmen
Published: March 2019

Retama raetam( RR) and R. sphaerocarpa( RS) are shrubs growing in Algeria desert areas, where are commonly used as healing remedies because of their antiseptic, antipyretic and anti-diarrheal properties. Phytochemical studies have shown that these species are very rich in flavonoids (isoflavones) and alkaloids (quinolizidine and bipiperidyl). The aim of this study was to compare the chemical composition of both Retama species by GC/MS and LC/MS and to determinate their antimicrobial activity of two Retama species growing naturally in Algeria. Ten alkaloids and seven flavonoids were identified in cladodes of RR and RS. The quantitative analysis showed that the most abundant flavonoid of both the aqueous extract from RR and RS was the isoflavone genistein (610.0±2.8 and 408.0±14.1 mg/100 g respectively), whereas sparteine was the predominant alkaloid in RR and retamine in RS. The antibacterial activity of Retama extracts against standard strains was performed by minimum inhibitory concentration (MIC), and by the disc diffusion method (expressed by inhibition zone, IZ). Both Retama species showed the best activity against Staphylococcus aureus and methicillin-resistant S. aureus(MRSA), being RS aqueous extract more active than RR aqueous extract, with MIC 125 μg/mL and bactericidal activity against both strains.
An Efficient Synthesis of Angelmarin and its Analogs
Authors: Liu Su-You , Xu Na , Liu Li-Jun , Wang Ying-Xiong , Ma Da-You
Published: March 2019

Angelmarin, a naturally occurring coumarin, exhibited highly anti-austerity potency towards human pancreatic carcinoma cell line PANC-1. In this paper, an efficient and eco-friendly synthesis of angelmarin and its analogs from columbianetin has been developed via a ZnO mediated esterification and a Wittig reaction.
Antifungal Activity of the Extract and the Active Substances of Endophytic Nigrospora sp. from the Traditional Chinese Medicinal Plant Stephania kwangsiensis
Authors: Luo Haiyu , Zhou Qiuyan , Deng Yecheng , Deng Zhiyong , Qing Zhen , Sun Wenbin
Published: March 2019

To exploit a new source from medical plants for finding bioactive products, endophytic fungi DBR-5 identified as Nigrospora sp., was isolated from the root tubers of the traditional Chinese medicinal plant Stephania kwangsiensis Lo. The antifungal activities of the extract from its fermentation liquids were determined. The ethyl acetate extract of DBR-5 exhibited high and broad antifungal activities against plant pathogenic fungi, and showed high toxicity to Exserohilum turcicum, Bipolaris maydis, Ceratocystis paradoxa, Alternaria oleracea and Cochliobolus miyabeanus with EC50 values respectively at 0.01 mg/mL, 0.02 mg/mL, 0.03 mg/mL, 0.03 mg/mL and 0.04 mg/mL. By a bioassay guided fractionation, three antifungal secondary metabolites were isolated from liquid culture of DBR-5, and identified as griseofulvin, deoxybostrycin and austrocortirubin on the basis of spectroscopic analysis. In vitro antifungal assay showed that griseofulvin displayed significant inhibition against the hypha growth of tested plant pathogenic fungi with EC50 values ranging from 0.0013 mg/mL to 0.0202 mg/mL, and showed the highest toxicity to E. turcicum and C. paradoxa with EC50 values both at 0.0013 mg/mL. Compared with the broad spectrum fungicide carbendazim, except that the toxicity of griseofulvin to Diaporthe citri and Pestalotiopsis theae was lower, the toxicity to the other eight pathogenic fungi was much higher. The inhibitory rates of griseofulvin against spore germination of A. olerace, C. paradoxa and P. theae were 100%, 100% and 94.39% respectively, at a concentration of 0.01 mg/mL. The other two compounds deoxybostrycin and austrocortirubin exhibited only weak antifungal activities. The results indicate the potential of Nigrospora sp. DBR-5 as a source of griseofulvin and also support that griseofulvin is a natural compound with high potential bioactivity against plant pathogenic fungi.
Phytochemical Study and Antioxidant Activity of Calligonum azel and C. comosum
Authors: Belaabed Soumia , Beghidja Noureddine , Ayoub Khalfaoui , D'Ambola Massimiliano , De Leo Marinella , Cotugno Roberta , Marzocco Stefania , De Tommasi Nunziatina
Published: March 2019

One new phenolic compound (1) together with nine known derivatives were isolated from the aerial part apolar extracts of Calligonum azel Maire and Calligonum comosum L'Hér (Polygonaceae). Their structures were established on the basis of 1D and 2D NMR spectroscopy, as well as ESI-MS analysis. The anti-inflammatory and antioxidant potential of pure compounds was evaluated in J774A.1 murine macrophages and Jurkat cells. Among tested molecules, 4-ethoxy-1,2-benzendiol, tamgermanetin, and α,β-diamino-4-hydroxybenzene butanoic acid exerted the more interesting activity.
Beneficial Effects of Curcumin on the Wound-healing Process after Tooth Extraction
Authors: Mitic Aleksandar , Todorovic Kosta , Stojiljkovic Nenad , Stojanovic Nikola , Ilic Sonja , Todorovic Ana , Stojnev Slavica
Published: March 2019

This study evaluated the effects of curcumin, a naturally occurring compound with numerous health-beneficial properties, on the wound-healing process of extraction sockets (soft tissue that surrounded the extracted tooth) in rats. The effects of topically applied curcumin were monitored by tracking changes in myeloperoxidase activity and nitric oxide concentrations in soft tissue homogenates 3 and 7 days following surgery. Additionally, pathohistological examination of tissue sections was used to reveal the effects of curcumin on the course of wound healing on a microscopic level. Compared to the untreated control, topically administered curcumin statistically significantly decreased soft-tissue myeloperoxidase activity and nitric oxide concentrations after both 3 and 7 days of application. Microscopic analysis showed a reduced inflammatory infiltrate (subjectively and morphometrically estimated as the number of polymorphonuclear cells/100 μm2) and an increased collagen deposition in rats treated with curcumin. The obtained results point to the great potential of curcumin in the acceleration of tooth extraction wound-healing processes partially through the reduction of the inflammatory response and increase in collagen deposition. Thus, these results significantly contribute to the previously suggested application of curcumin in the skin wound treatment by potentially broadening its usage in the treatment of mucosal wounds.
Effect of Harvest and Drying on Composition of Volatile Profile of Elderflowers (Sambucus nigra) from Wild
Authors: Bajer Tomáš , Bajerová Petra , Ventura Karel
Published: March 2019

Volatile compounds emitted by elderflowers ( Sambucus nigra L.) at various stages (blooming on the bush, and at different stages after harvesting) were analyzed to investigate changes in the composition of volatile profiles induced by two drying procedures. Solid-phase microextraction and simultaneous distillation-solvent extraction were used for concentration of volatiles. Analyses of extracts were performed using gas chromatography coupled with a mass spectrometer or a flame ionization detector. On-site field sampling of volatiles followed-up by chromatographic analysis provided interesting information, including insect pheromones from 55 % to 79 % of the total peak area in the GC/MS chromatograms. Composition of aroma compounds of harvested elderflowers was strongly influenced by the type of drying procedure, where the content of some volatiles decreased and some substances even occur due to ongoing physicochemical processes. Changes in volatile profile caused by harvesting were also observed.
Chemical Composition of the Essential oil of Syzygium kanarense: An Endemic and Rediscovered Species from the Western Ghats, India
Authors: Joshi Rajesh K. , Shenoy H. Sooryaprakash , Marati Ramakrishna
Published: March 2019

The hydro-distilled essential oil obtained from the aerial parts of Syzygium kanarense(Talbot) Raizada (Myrtaceae) was investigated for the first time by gas chromatography equipped with flame ionization detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC/MS). Fifty-two constituents were identified, which represented 91.9% of the total oil. The major compounds were seychellene (7.3%), α-muurolol (5.4%), cis-cadinene ether (5.3%), β-vetivenene (5.1%), 10 epi-γ-eudesmol (4.8%), guaiol (4.5%), longiborneol (4.1%), δ-elemene (4.1%) and α-muurolene (4.1%). The oil was found to be rich in sesquiterpene hydrocarbon (49.5%) type constituents.
Herbal Therapy in Pregnancy-What to Expect when you Expect?
Authors: Belica Artur L. , Ćetković Nenad B. , Milić Nataša B. , Milošević Nataša P.
Published: March 2019

The use of herbal therapy in pregnancy is common for pregnancy related nausea, vomiting, gestational diabetes, anxiety, insomnia, and preparation for labor, as well as for treating infections. Many conventional drugs may interfere with fetal development and herbal products are considered to be safe. However, herbal therapy requires competent healthcare professional advice before prescribing. Knowledge about the possible adverse effects of active compounds of the herbs on pregnancy outcome is limited. Interference of herbal ingredients with conventional medication or the ailment should also not be excluded. For many herbal products, the pharmacological effect is not clinically proven, and the safe usage in pregnancy is not guaranteed. Here, based on published clinical trials, an overview is given of the efficacy and safety for fetal development and pregnancy outcome of the most frequently used herbs: ginger, cranberry, echinacea, mint, chamomile, valerian, flaxseed, tea and raspberry leaf.
Cytotoxic and Antifungal Terpenoids from Bornean Soft Coral, Sinularia flexibilis
Authors: Kamada Takashi , Phan Chin-Soon , Hamada Toshiyuki , Hatai Kishio , Vairappan Charles Santhanaraju
Published: March 2019

One new cembrane, ent -sinuflexibilin D (1), along with seven known compounds (2-8) were isolated from a population of Bornean soft coral Sinularia flexibilis. Their structures were elucidated on the basis of spectroscopic analyses. Cytotoxicity and antifungal activities of these compounds were evaluated in vitro. In addition, muurolene 7 was first isolates from a marine source.
Compounds from the Roots of Codonopsis pilosula and Their SIRT1 Regulatory Activity
Authors: Zheng Tao , Cheng Li-Zhi , Yan Yong-Ming , Xu Fu-Rong , Tang Xiao-Long , Li Xiao-Zhen , Qin Fu-Ying , Liu Bao-Hua , Cheng Yong-Xian
Published: March 2019

Two new compounds, pilosuloside A (1) and pilosulain A (2), one new natural occurring compound (3), and twelve known compounds (4-15), were isolated from the roots of Codonopsis pilosula. Their structures were elucidated by a combination of spectroscopic methods. Regulation of SIRT1 activity by all the compounds was evaluated. The results showed that 4 could activate SIRT1 in a concentration-dependent manner.
Protective Effects of Pelargonidin on Lipopolysaccharide-induced Hepatic Failure
Authors: Lee Wonhwa , Lee Yuri , Kim Jaehong , Bae Jong-Sup
Published: March 2019

Pelargonidin (PEL) is a well-known red pigment found in plants and has important biological activities that are potentially beneficial for human health. The aim of this study was to investigate the effect of PEL on lipopolysaccharide (LPS)-induced liver failure in mice, and to elucidate its underlying molecular mechanisms. Liver failure was induced by LPS (15 mg/kg, i.p) in mice, and 12 h later, they were treated intravenously with PEL. Administration of LPS significantly increased mortality, serum levels of alanine transaminase (ALT), aspartate transaminase (AST), and inflammatory cytokines, and expression of toll-like receptor 4 (TLR4) protein; PEL treatment effectively countered these effects of LPS. Further, LPS treatment markedly increased the expression of myeloid differentiation primary response gene 88 (MyD88), phosphorylation of p38, extracellular signal-regulated kinase (ERK), and c-Jun N-terminal kinase (JNK), and expressions of nuclear proteins, such as nuclear factor (NF)-κB and phosphorylated c-Jun. Additionally, LPS increased the serum levels of tumor necrosis factor (TNF)-α and interleukin (IL)-6. All these effects of LPS were attenuated by PEL. In addition, the LPS-mediated increase in the level of serum interferon (IFN)-β expression of the TLR-associated activator of IFN (TRIF) protein, and phosphorylation of IFN regulator factor 3 (IRF3) were reduced by PEL. Our results suggest that PEL attenuates LPS-induced liver damage by inhibition of the TLR-mediated inflammatory pathway and could be used to treat liver diseases.
Malvidin and its Glycosides from Vaccinium ashei Improve Endothelial Function by Anti-inflammatory and Angiotensin I-Converting Enzyme Inhibitory Effects
Authors: Huang Wu-Yang , Wang Xing-Na , Wang Jing , Sui Zhong-Quan
Published: March 2019

Protective effects of malvidin and the glycosides from Vaccinium ashei on endothelial cells were investigated. The results showed that malvidin, malvidin-3-glucoside, malvidin-3-galactoside, and their mixture could defend endothelial cells from damage caused by TNF-α, and inhibit monocyte chemotactic protein-1, intercellular adhesion molecule-1, vascular cell adhesion molecule-1, and angiotensin I-converting enzyme expression. In addition, they could inhibit degradation of IκBα and obstruct the nuclear translocation of p65, suggesting the anti-inflammatory mechanism of NF-κB pathway. The results indicated blueberry anthocyanins could be potential inflammation and ACE inhibitors, and blueberry could be functional foods advantageous to maintain a healthy cardiovascular population.
Isolation of Resistomycin from a Terrestrial Actinomycete with TRAIL Resistance-overcoming Activity
Authors: Liu Xuefeidan , Arai Midori A. , Ishibashi Kazufumi Toume and Masami
Published: March 2019

Tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL) potently induces apoptosis in most cancer cells, but not in normal cells, and, thus, has attracted intense interest as a promising antitumor agent. Activity-guided fractionation of the culture broth of the actinomycete CKK1172 strain led to the isolation of the antibiotic resistomycin (1) using human gastric adenocarcinoma AGS cells. Compound 1 exhibited TRAIL resistance-overcoming activity at 2 μM with 38% more inhibition than a treatment with 1 alone (without TRAIL) in TRAIL-resistant AGS cells.
A New Alkenylphenol from the Propolis of Stingless Bee Trigona minor
Authors: Nguyen Hai Xuan , Van Do Truong Nhat , Nguyen Mai Thanh Thi , Dang Phu Hoang , Tho Le Huu , Awale Suresh , Nguyen Nhan Trung
Published: March 2019

A new alkenylphenol, 2-hydroxyl-6-(14' Z -nonadecenyl)benzoic acid (1), was isolated from the ethanolic extract of Vietnamese stingless bee propolis Trigona minor (Meliponini, Apidae), together with two known compounds (2 and 3). Their chemical structures were determined by extensive NMR spectroscopic analysis. All compounds were tested for preferential cytotoxicity against the PANC-1 human pancreatic cell line under nutrition-deprived conditions (NDM). Compound 1 exhibited the strongest preferential cytotoxicity, with a PC50 value of 2.4 μM.
Synthesis of Halogenated-4-Nitrophenyl 2-deoxy-2-halogeno-pyranosides via N -Halogenosuccinimide Activated Glucal
Authors: Inoue Chieri , Okamoto Yumi , Vavricka Christopher J. , Kiyota Hiromasa , Izumi Minoru
Published: March 2019

Reaction of 3,4,6-tri- O -acetyl-D-glucal with silver 4-nitrophenolate in the presence of N -iodosuccinimide and N -bromosuccinimide produced (2,6-dihalo-4-nitro)phenyl 2-halo-2-deoxy-α-D-glycopyranosides. Although bromination and iodination of the 4-nitrophenyl group could not be avoided, the resulting (2,6-dihalo-4-nitro)phenylated compounds can be used as substrates or covalent glycosidase inhibitors after deprotection. The stereoselectivity and regioselectivity of the halogenation reactions are described.
Motor and Behavioral Effects of Moringa oleifera Leaf Extract
Authors: Al-Abri Mohammed , Ashique Mohammed , Ramkumar Aishwarya , Nemmar Abderrahim , Ali Badreldin H.
Published: March 2019

Moringa oleifera is a medicinal plant widely used in many parts of the world for hypertension, pain and epilepsy. The aim of this study was to determine the effect of M. oleifera aqueous leaf extract on motor and behavioral activities of healthy mice. Male mice were randomly divided into a control group (given 0.9% NaCl orally) and three groups treated with the extract at doses of 100, 200, and 400 mg/kg/day for 14 consecutive days. Motor and behavioral activity were evaluated by quantifying motor activity, exploration (hole-board), neuro-muscular coordination (rota rod treadmill), pain (hot plate, cold-water tail flick, and acetic acid-induced abdominal constriction), and depression (forced swimming test, FST). Administration of M. oleifera extract had a significant and dose-dependent antinociceptive action in both thermal and chemical tests ( p < 0.05). The extract (400 mg/kg) caused a reduction in exploration activity and neuro-muscular coordination, and decreased the mobility time in the FST, suggesting an antidepressant-like action. Motor activity was not significantly affected by any of the doses used. The results suggest that the plant aqueous extract may have a dose-dependent central nervous system (CNS) depressant action.
Antiviral Activity of the Sesquiterpene Lactones from Centipeda minima against Influenza a Virus in vitro
Authors: Zhang Xiaoli , He Jun , Huang Weihuan , Huang Huibin , Zhang Zeming , Wang Jiajian , Yang Li , Wang Guocai , Wang Yifei , Li Yaolan
Published: March 2019

During the course of searching for antiviral agents from Chinese medicinal herbs, we found that the supercritical fluid extract (SFE) of Centipeda minima possessed good in vitro antiviral activity against influenza virus A/Puerto Rico/8/34 H1N1 (PR8). Bioassay-guided isolation and identification led to the isolation from this extract of seven pseudoguaianolides (1-7). These, as well as nine other sesquiterpene lactones (8-16) previously isolated from this herb were all tested for their anti-PR8 activity using both the cytopathogenic effect (CPE) reduction and cell counting kit 8 (CCK8) assays. As a result, eight pseudoguaianolides (1-8) possessing an α,β-unsaturated cyclopentenone moiety showed antiviral activity against PR8 to different extents. Of the active compounds, brevilin A (4) exhibited the strongest anti-PR8 activity, with an IC50 value much lower than that of the positive control ribavirin. Mechanistic study revealed that brevilin A affected the intracellular replication of PR8 via downregulating the expression of viral M2 protein. All these results suggest the potential application of the pseudoguaianolides containing an α,β-unsaturated cyclopentenone moiety (e.g. brevilin A) in the treatment of influenza virus infection.