bluuebunny/crossref_metadata_2025 huggingface dataset:
Molecular Recognition of Carbohydrates: Evaluation of the Binding Properties of Pyrazole-based receptors and their Comparison with Imidazole- and Indole-based Systems
Authors: Sonnenberg Claudia , Hartmann André , Mazik Monika
Published: March 2019

The aim of the study was to evaluate the potential of pyrazole-based receptors in the complexation of carbohydrates. Representatives of a new series of acyclic pyrazole-based receptors were prepared and their binding properties toward selected mono- and disaccharides evaluated. The results of the binding studies were compared with those obtained for acyclic imidazole- and indole-based receptors. The first binding studies revealed di- vs monosaccharide binding preferences of the new receptors and showed that pyrazole units are useful building blocks for the construction of receptors with interesting binding preferences.
Rapid Acyl Migration between Pyrogallyl 1,2- and 1,3-Dipivaloates
Authors: Shan Yaming , Liu Jimmy (Jingyue) , Rath Nigam P. , Gokel George W.
Published: March 2019

Pyrogallol and its derivatives are biologically active compounds, and pyrogallol also forms the basis of an increasingly important tetrameric supramolecular scaffold. Pyrogallol[4]arenes are tetrameric macrocycles that form from 1,2,3-trihydroxybenzene and aldehydes under acidic conditions. Pyrogallol was treated with two equivalents of pivaloyl chloride to form pyrogallyl dipivaloate. A mixture of regioisomers was invariably obtained and a rapid equilibrium was observed between the 1,2- and 1,3-diesters in polar solvents. A pure sample of solid pyrogallyl 1,2-dipivaloate was isolated and its crystal structure was obtained. The pure compound was shown to rearrange to mixtures similar to those isolated initially.
Intracellular Localization of PNA in Human Cells upon its Introduction by Electroporation
Authors: Noguchi Eri , Shigi Narumi , Komiyama Makoto
Published: March 2019

Peptide nucleic acid (PNA) is one of the most useful DNA analogs in a wide variety of gene analysis in human cells. In order to exhibit its maximal functions, PNA must be localized to a desired place (e.g., nucleus, cytoplasm and other organelles). Here, we introduced PNAs into HeLa cells by electroporation and examined their localization at various time points. The PNA which binds to the mitochondrial COII gene was initially accumulated in the nucleus, and thereafter mostly transferred to cytoplasm. This time-dependent intracellular localization of PNA is ascribed to the breakdown of the nuclear envelope in the cell division. On the other hand, another PNA that binds to telomere repeat sequence mostly remained in the nucleus, even after the cell division occurred. The retention of this PNA in the nucleus was further enhanced when it was conjugated with Cy3.
Fliposomes: pH-controlled Release from Liposomes Containing New trans-2-Morpholinocyclohexanol-based Amphiphiles that Perform a Conformational Flip and Trigger an Instant Cargo Release upon Acidification
Authors: Zheng Yu , Liu Xin , Samoshina Nataliya M. , Chertkov Vyacheslav A. , Franz Andreas H. , Guo Xin , Samoshin Vyacheslav V.
Published: March 2019

A new type of pH-sensitive liposome (fliposomes) was designed based on the amphiphiles that are able to perform a pH-triggered conformational flip (flipids). This flip disrupts the liposome membrane and causes rapid release of the liposome cargo, specifically in the areas of increased acidity. The flipids (1-3) are equipped with a trans-2-morpholinocyclohexanol conformational switch. pH-Sensitive fliposomes containing one of these flipids, POPC and PEG-ceramide (molar ratio 50/45/5) were constructed and characterized. These compositions were stable at 4oC and pH 7.4 for several months. Fliposomes loaded with ANTS/DPX demonstrated an unusually quick content release (in a few seconds) at pH below 5.5, which was more efficient in the case of flipid 1 with the shorter linear C12-tails. The pH-titration curve for the fliposome leakage paralleled the curve for the acid-induced conformational flip of 1-3 studied by 1H NMR. A plausible mechanism of the pH-sensitivity starts with an acid-triggered conformational flip of 1, 2 or 3, which changes the molecular size and shape, shortens the lipid tails, and perturbs the liposome membrane resulting in the content leakage.
Competition of Ester, Amide, Ether, Carbonate, Alcohol and Epoxide Ligands in the Dirhodium Experiment (Chiral Discrimination by NMR Spectroscopy) [1]
Authors: Mattiza Jens T. , Meyer Vera , Özüduru Gülsüm , Heine Tanja , Fohrer Joerg , Duddeck Helmut
Published: March 2019

Thirty-eight derivatives of 3-hydroxy-2-methylpropanoic acid, each with two different oxygen functionalities, were synthesized and subjected to the standard dirhodium experiment (1H NMR in the presence of an equimolar amount of the chiral dirhodium tetracarboxylate complex Rh*). Their structures represent ester, amide, carbonate, ether, alcohol and/or epoxy groups. Significant selectivity in the binding of those oxygen groups to the complex were determined. From these results, a priority list in binding to a rhodium atom of Rh* was established:

epoxides > primary alcohols > ethers ≥ esters ≥ amides > carbonates > tertiary alcohols

This sequence allows the prediction of the preferred binding site of oxygen-containing groups in polyfunctional compounds, which frequently occur among natural products, and, particularly, in asymmetric synthesis of such compounds. Differentiation of the enantiomers by the dirhodium experiment is easily accomplished due to numerous signal dispersions in nearly all cases.
Synthesis of Acetylene Bridged Germanium Phthalocyanines
Authors: Plenzig Felicitas , Lyubimtsev Alexey , Hanack Michael
Published: March 2019

The octaalkyl- or octaalkoxysubstituted phthalocyaninatogermanium dichlorides 10b,d,e and 10a-c were reacted with bisbromomagnesiumacetylene 16 and bisbromomagnesium- p-diethynylbenzene 18, respectively with formation of the corresponding acetylene bridged oligomers 17a-c and 19a-c, respectively.
Host-Guest Chemistry of Alkaloids
Authors: Yatsimirsky Anatoly K.
Published: March 2019

Binding of alkaloids by different hosts (native and modified cyclodextrins, cucurbiturils, calixarenes, and metal complexes of porphyrin and Salphen-type ligands), as well as receptor properties of alkaloid based hosts are reviewed. With alkaloids as guests, the largest binding constants and most significant spectral changes, in particular strong fluorescence enhancements induced by complexation with isoquinoline alkaloids, are observed with cucurbituril hosts. Cyclodextrins are successfully employed for improvement of solubility and for chiral separation of alkaloids of different types. Receptor properties of native and modified cinchona and bisbenzylisoquinoline alkaloids have attracted considerable attention for development of chiral selectors for analysis and separation.
The Effect of Diallyl Polysulfanes on Cellular Signaling Cascades
Authors: Montenarh Mathias , Saidu Nathaniel E. B.
Published: March 2019

Diallyl polysulfanes, such as diallyl trisulfide and diallyl tetrasulfide, are regarded as a group of potential chemopreventive compounds as they have been proven to be effective inhibitors of cancer cells. These agents have been implicated in signal transductions, including the generation of Reactive Oxygen Species (ROS), Endoplasmic Reticulum (ER) stress, mitogen-activated protein kinase (MAPK) signaling, regulation of cell cycle progression, and induction of apoptosis. Nonetheless, certain aspects of the diallyl polysulfane triggered inhibitory effects on cancer cells are still not clear. Understanding the targeted signaling pathways may help to develop new strategies to treat cancer and other diseases. This review is therefore aimed at addressing the targeting of specific intracellular signal transduction cascades by these diallyl polysulfanes in order to shed some light on possible mechanisms of action of these compounds.
Determination of the Absolute Stereochemistry of Limonene and α-Santalol by Raman Optical Activity Spectroscopy
Authors: Sakamoto Akira , Ohya Nao , Hasegawa Toshio , Izumi Hiroaki , Tokita Nakako , Hamada Yoshiaki
Published: March 2019

Determining the absolute stereochemistry of organic compounds in solution remains a challenge. We investigated the use of Raman optical activity (ROA) spectroscopy to address this problem. The absolute configurations of (+)-( R)- and (-)-( S)-limonene were determined by ROA spectroscopy, which can be applied to smaller amounts of sample as compared with vibrational circular dichroism (VCD) spectroscopy. This ROA method was also applied to (+)-( E)-α-santalol and shown to be successful in the determination of the absolute configuration of this compound. ROA spectroscopy shows promise as a useful tool for determining the absolute stereochemistry of many natural compounds.
Chemical Constituents from Farfugium Japonicum Var. formosanum
Authors: Hsieh Sung-Fei , Hsieh Tain-Jye , El-Shazly Mohamed , Du Ying-Chi , Wu Chin-Chung , Hwang Tsong-Long , Wu Yang-Chang , Chang Fang-Rong
Published: March 2019

Two new eremophilenolides, 6β8β10β-trihydroxyeremophil-7(11)-en-12,8-olide (1) and 3βacetoxy-8α-hydroxy-6β-methoxyeremophila-7(11),9-dien-12,8-olide (2) along with twenty-nine other compounds were obtained from the methanolic extracts of the aerial parts and rhizomes of Farfugium japonicum (L.) Kitam. v ar. formosanum (Hayata) Kitam. (Compositae = Asteraceae). The structures of the isolated compounds were characterized and identified by spectral techniques. Compounds 5, 6, 10, 12-24, 29, and 30, were reported for the first time from this genus. Cytotoxicity and anti-inflammatory activity of the isolated compounds were evaluated. Compounds 3 and 16 possessed moderate cytotoxicity against human breast cancer cell line (MCF 7). Compounds 3, 16, 25 and 26 exhibited moderate cytotoxicity against hepatoma cells (Hep G2 and Hep 3B). With respect to the anti-inflammatory activity, compounds 15 and 16 (each 10 μg/mL) inhibited superoxide anion generation by human neutrophils in response to fMLP/CB by 92.0% and 87.3%, respectively.
Four New Guaianolides and Acetylenic Alcohol from Saussurea Katochaete Collected in China
Authors: Saito Yoshinori , Iwamoto Yuko , Okamoto Yasuko , Gong Xun , Kuroda Chiaki , Tori Motoo
Published: March 2019

Four new guaianolides and an acetylenic alcohol were isolated from Saussurea katochaete (Asteraceae) collected in China. The structures were determined based on the spectroscopic data including the absolute configuration by application of advanced Mosher's method.
Four New Bisabolane-type Sesquiterpenes from Ligularia Lankongensis
Authors: Hirota Hiroshi , Horiguchi Yurie , Kawaii Satoru , Kuroda Chiaki , Hanai Ryo , Gong Xun
Published: March 2019

The chemical constituents of the roots of two Ligularia lankongensis samples collected in Yunnan and Sichuan Provinces, China, were investigated, together with the DNA sequence of the atpB-rbcL and ITS regions. Four new highly oxygenated bisabolane-type sesquiterpenes (1 – 4) were obtained. Intraspecific diversity in the DNA sequence was found to be limited.
A New Diterpene from the Leaves of Andrographis Paniculata Nees
Authors: Radhika Parvataneni , Prasad Yejella Rajendra , Sowjanya Kattupalli
Published: March 2019

Phytochemical investigation of the methanolic extract of the leaves of Andrographis paniculata Nees yielded a minor, new diterpene, 21-nor-3,19–isopropylidine-14-deoxy-ent-labda-8(17),13-dien-16,15-olide (1), together with five known labdane type diterpenes, andrographolide 3, 14-deoxyandrographolide 4, 14–deoxy–12–hydroxyandrographolide 5, 14–deoxy–11,12–dihydroandrographolide 6, neoandrographolide 7, and two acids, cinnamic acid 8, and ferulic acid 9. The chemical structures were established by spectroscopic analyses, including 1D- and 2D-NMR spectroscopic experiments, and on the basis of HR-ESI MS analyses. The methanolic extract of the leaves exhibited moderate antibacterial and antifungal activities at a dose of 200 μg/mL in comparison with the reference standards.
Oropheayunnol, an Unusual 22,23-Epoxy Apotirucallane Triterpenoid from Orophea Yunnanensis
Authors: Lan Wen-Jian , Wang Jun , Guo Yan-Qiong , Yin Sheng
Published: March 2019

A new apotirucallane-type triterpenoid with an unusual 22,23-epoxy group in the side chain, 22,23-epoxy-apotirucalla-14-ene-3α,7α,24α,25-tetraol (1), was isolated from the leaves and twigs of Orophea yunnanensis. The structure of 1 was established on the basis of HRESIMS, 1D, and 2D NMR spectroscopic methods. This is the first phytochemical study of Orophea yunnanensis, and the biogenetic origin of 1 was postulated. Compound 1 exhibited weak cytotoxicity in vitro against the growth of CNE1 nasopharyngeal carcinoma cell line with an IC50 value of 9.7 μg/mL.
New Metabolites from the Marine-Derived Fungus Aspergillus Fumigatus
Authors: Afiyatullov Shamil Sh. , Zhuravleva Olesya I. , Antonov Alexandr S. , Kalinovsky Anatoly I. , Pivkin Michail V. , Menchinskaya Ekaterina S. , Aminin Dmitry L.
Published: March 2019

A new alkaloid, fumiquinazoline K (1), and a new nordammarane triterpenoid (2), together with three known diketopiperazines (3-5) and tryptoquivaline F (6) have been isolated from a marine strain of Aspergillus fumigatus KMM 4631 associated with the soft coral Sinularia sp. Their structures were determined by HR-MS and 1D and 2D NMR. Compounds 3-5 exhibit weak cytotoxicity against cytoplasm non-specific esterase in Ehrlich carcinoma cells. Compound 3 also induces early apoptosis of the same cells in a non-toxic range of concentrations.
Formation of Tetrahydrocurcumin by Reduction of Curcumin with Cultured Plant Cells of Marchantia Polymorpha
Authors: Shimoda Kei , Kubota Naoji , Hirano Hirotaka , Matsumoto Masahiro , Hamada Hatsuyuki , Hamada Hiroki
Published: March 2019

Cultured plant cells of Marchantia polymorpha, Nicotiana tabacum, Phytolacca americana, Catharanthus roseus, and Gossypium hirsutum were examined for their ability to reduce curcumin. Only M. polymorpha cells converted curcumin into tetrahydrocurcumin in 90% yield in one day. Time-course experiment revealed a two-step formation of tetrahydrocurcumin via dihydrocurcumin.
Regioselective Formation of Silybin-23-β-D-Glucoside by Glucosylation of Silybin with Cultured Plant Cells of Eucalyptus Perriniana
Authors: Shimoda Kei , Imai Hiroya , Mandai Tadakatsu , Hamada Hiroki
Published: March 2019

Time course experiment revealed that cultured plant cells of Eucalyptus perriniana regioselectively glucosylated silybin to silybin-23-β-D-glucoside in up to 70% yield.
Diversification of Exudate Flavonoid Profiles in Further Primula spp
Authors: Bhutia Tshering Doma , Valant-Vetschera Karin M.
Published: March 2019

In continuation of previous work, exudate flavonoid profiles of 22 new accessions of the genus Primula L. aligned to different subgenera were studied for the first time. Profiling was done by comparative TLC and UV-HPLC against authentic marker compounds. Most of the studied species accumulated the typical Primula flavonoids, comprising derivatives of unsubstituted flavone, of 5,8- or 5,6-hydroxyflavones including partly highly oxygenated flavones, together with 2,2′-diOH-chalcone in their exudate. The profile of P. edelbergii belonging to subgen. Sphondylia differed largely from the majority of Primula species studied so far, showing accumulation tendencies similar to those observed earlier for the closely related genus Dionysia. The phylogenetic significance of this diversification is shortly addressed.
Water-soluble Constituents of the Heartwood of Streblus asper
Authors: Li Jun , Tang Mao-Tong , Wu Qiang , Chen Hong , Niu Xiao-Tao , Guan Xin-Lan , Li Jian , Deng Sheng-Ping , Su Xiao-Jian , Yang Rui-Yun
Published: March 2019

A new lignan, (7′ R,8′ R)- threo-strebluslignanol-2- O-β-D-glucopyranoside, along with 8 known compounds (2–9) were isolated from the water-soluble part of the MeOH extract of the heartwood of Streblus asper. Their structures were elucidated through various spectroscopic methods, including 1D NMR (1H NMR, 13C NMR), 2D NMR (HMQC, HMBC, and NOESY), and HRMS. The stereochemistry at the chiral centers was determined using the CD spectrum, as well as analyses of coupling constants and optical rotation data. In the preliminary bioassay, the isolated compounds did not show anti-HBV activities in vitro using the HBV transfected HepG2.2.15 cell line.
Antioxidant, Hemolytic and Cytotoxic Activities of Senecio Species used in Traditional Medicine of Northwestern Argentina
Authors: Lizarraga Emilio , Castro Felipe , Fernández Francisco , de Lampasona Marina P. , Catalán César A. N.
Published: March 2019

Senecio nutans Sch. Bip., S. viridis var. viridis Phill. and S. spegazzinii Cabrera are native species used in traditional medicine of northwestern Argentina. The total phenolics, flavonoids and caffeoylquinic acids contents, as well as radical scavenging, antioxidant, hemolytic and cytotoxic activities of aqueous extracts (infusion and decoction) of all three species were determined. S. nutans was the most active. The extracts did not show antibacterial activity. Alkaloids were not detected in any of the aqueous extracts of the three studied species.
Evaluation of Analgesic Activities of Tremetone Derivatives Isolated from the Chilean Altiplano Medicine Parastrephia lepidophylla
Authors: Benites Julio , Gutierrez Eunices , López José , Rojas Mauricio , Rojo Leonel , do Céu Costa Maria , Vinardell Maria Pilar , Calderon Pedro Buc
Published: March 2019

Parastrephia lepidophylla, family Asteraceae, has ancient use in traditional medicine in the region of Tarapacá, Chile. Bioguided fractionation of extracts of this plant was undertaken in the search for compounds with analgesic and antioxidant activity. Two benzofuran derivatives were isolated as the major components of this plant, identified as tremetone 1 and methoxytremetone 6. Remarkably, neither of these showed antioxidant activity, but tremetone 1 exhibited a morphine-like analgesic property. Reduction of this analgesic effect by naloxone suggests a direct effect on opiate receptors as a possible signaling pathway. However, both the low diffusion across lipid membranes (PAMPA assay) and the lipophilicity (Log P) shown by tremetone 1 make elusive the mechanism explaining its induced analgesia.
Base-mediated Transformations of 3,5-Dibromoverongiaquinol from the Sponge Aplysina sp. to Cavernicolins-1, -2 and a Subereatensin Analogue
Authors: Santalova Elena A.
Published: March 2019

Treatment of 3,5-dibromoverongiaquinol (1) with NaHCO3-MeOH at room temperature gave cavernicolin-1 (2), cavernicolin-2 (3), the 4,7-dimethoxy analogue of subereatensin (4) and dimethyl ketal (5). These transformations may clarify the origin of the cavernicolins and subereatensin isolated from the extracts of some verongid sponges.
Evaluation of Volatile Constituents of Cochlospermum angolense
Authors: Leonardi Michele , Giovanelli Silvia , Cioni Pier Luigi , Flamini Guido , Pistelli Luisa
Published: March 2019

The chemical composition of the essential oils obtained from the leaves and roots of Cochlospermum angolense (Welw) growing wild in Angola was analyzed for the first time by capillary gas chromatography (GC) and gas chromatography/mass spectrometry (GC-MS). The investigation led to the identification of 67 and 130 compounds from the leaves and roots, respectively. Both oils were strongly characterized by the presence of sesquiterpenoids (68.8% in the leaves and 53.2% in the roots), while monoterpenoids were present in minor percentages (9.8% in the leaves and 26.2% in the root). The main constituents of the leaves were germacrene D (9.4%), α-cadinol (7.4%) and 10- epi-cubenol (6.2%), while the most abundant compounds in the root essential oil were the sesquiterpenes β-caryophyllene (19.7%) and isoborneol (6.6%). The analysis by HS-SPME of the roots, leaves, fruits and seeds were also reported for the first time. Different volatile profiles were detected.
Composition of the Essential Oil of Wild Growing Artemisia vulgaris from Erie, Pennsylvania
Authors: Williams Jack D. , Saleh Ayman M. , Acharya Dom N.
Published: March 2019

Essential Oil from wild growing Artemisia vulgaris L. originating in Erie, Pennsylvania was obtained by hydrodistillation of the aerial parts of the plant. Gas chromatographic-mass spectral analysis was used to identify the major volatiles present. Up to 22 components were detected in the essential oils. Germacrene D (25%), Caryophyllene (20%), α-Zingiberene (15%) and Borneol (11%) represent the major components of leaf oil, while the buds were rich in 1,8-Cineole (32%), Camphor (16%), Borneol (9%), and Caryophyllene (5%). trans-2-Hexenal was also detected in the aerial parts of the plant. α-Zingiberene and trans-2-Hexenal have not been previously reported for Artemisia vulgaris L. The major analytes are compared to those from Artemisia vulgaris L, originating outside of the United States.
Chemical Composition of the Essential Oils from the Flower, Leaf and Stem of Lonicera japonica
Authors: Vukovic Nenad , Kacaniova Miroslava , Hleba Lukas , Sukdolak Slobodan
Published: March 2019

The essential oils from different aerial parts of Lonicera japonica have been extracted by hydro-distillation and analyzed by gas chromatography and gas chromatography coupled with mass spectrometry. Quantitative and qualitative differences were found between the analyzed plant parts. A total of eighty-nine compounds were identified. The main constituents were ( Z, Z)-farnesole (16.2%) and linalool (11.0%) for the flowers fraction, hexadecanoic acid (16.0%) and linalool (8.7%) for the leaves fraction, and hexadecanoic acid (31.4%) for the stems. Monoterpene hydrocarbons were absent from all the oils, and oxygenated sesquiterpenes were not identified in the essential oil of the stem.
In vitro Bioactivity of Essential Oils and Methanol Extracts of Salvia reuterana from Iran
Authors: Ghomi Javad Safaei , Masoomi Reihaneh , Kashi Fereshteh Jookar , Batooli Hossein
Published: March 2019

The chemical composition of the essential oils, antioxidant activity (DPPH and β-carotene/linoleic acid assays) and total phenolic content (Foline-Ciocalteu) of the flowers and leaves of Salvia reuterana were determined. Essential oils extracted from the flowers and leaves by hydrodistillation were analyzed by GC and GC/MS. Forty-four constituents, representing 99.7-99.9% of the oils, were identified. The major components were germacrene D, benzoic acid hexyl ester, bicyclogermacrene, β-gurjunene and ishwarene, constituting 33.7-31.9% of the oils. The highest radical-scavenging activity (DPPH test) was shown by the methanol extract of the flowers (IC50=77.6 μg/mL). In the β-carotene/linoleic acid assay, the methanol extract of the leaves showed the highest inhibition (40.3%) which was only slightly lower than that shown by BHT (82.9%). The total phenolic contents of the methanol extracts of the flowers and leaves as gallic acid equivalents were 81.4 and 88.3 μg/mg, respectively. The plant also showed good antimicrobial activity against three strains of tested microorganisms.
Composition, Antimicrobial and Free-radical Scavenging Activities of the Essential Oil of Plectranthus marrubatus
Authors: Asres Kaleab , Tadesse Solomon , Mazumder Avijit , Bucar Franz
Published: March 2019

Essential oil from the aerial part of Plectranthus marrubatus J. K. Morton (Lamiaceae), obtained by hydrodistillation was analyzed by gas chromatography/mass spectrometry (GC/MS) and evaluated for antimicrobial and free radical scavenging activities. Twenty-four compounds representing 99% of the total oil were identified. The major constituents were thymol, p-cymene and γ-terpinene. The oil was tested against 21 bacterial and 4 fungal strains using the disc diffusion method and found to be active against a broad spectrum of pathogens including Gram-positive and Gram-negative bacteria as well as some fungal strains. The minimum inhibitory concentrations (MICs) of the oil against the bacterial strains tested ranged from 10 to 800 μg/mL, and from 400 to 800 μg/mL against the fungal strains employed. The in vitro antioxidant activity was assessed using 2,2-diphenyl-1-picrylhydrazil (DPPH) and showed a low EC50 value of 0.15 μl/mL. The study provides evidence for the broad-spectrum antimicrobial and antioxidant effect of Plectranthus marrubatus essential oil, and a possible explanation for its traditional use in the treatment of cold, fever, stomach disorder, diarrhea and as a skin cleaner.
Unusual Nitrogenous Derivatives from Alstonia
Authors: Tan Shin-Jowl , Subramaniam G. , Thomas Noel F. , Kam Toh-Seok
Published: March 2019

Five new nitrogenous compounds were isolated from the Malayan Alstonia angustifolia and their structures determined based on interpretation of spectroscopic data.
Photoactivated [3+2] Addition of 6,7-seco-angustilobine B to Fullerene [C60]
Authors: Macabeo Allan Patrick G. , Gehle Dietmar , Krohn Karsten , Franzblau Scott G. , Aguinaldo Alicia M.
Published: March 2019

A synthesis of a new alkaloid-fullerene conjugate (1) is reported. The reaction was carried out by photoinduced [3+2] cycloaddition of the Alstonia indole alkaloid, 6,7- seco-angustilobine B (2), to fullerene[C60] (3) under aerobic conditions. The major monoaddition photoadduct (1) was characterized unambiguously by UV, IR, MALDI-TOFMS and NMR experiments. A mechanism highlighted by sequential photoinduced electron transfer and radical recombination pathways is also proposed. No significant enhancement in inhibition against M. tuberculosis H37Rv was observed for 1 compared with its parent compounds 2 and 3.
Flavone C-Glycosides from Anthurium andraeanum
Authors: Clark Benjamin R. , Suzuki Jon Y. , Bliss Barbara J. , Borris Robert P.
Published: March 2019

We describe here the isolation of three flavone 6- C-glycosides from the leaves of Anthurium andraeanum, The two new flavones were identified through detailed spectroscopic analysis as 4″′-(3,4-dimethoxycinnamoyl)-embinin (2) and 4″′-ferruloyl-embinin (3).
LC-PDA-ESI/MS Identification of the Phenolic Components of Three Compositae Spices: Chamomile, Tarragon, and Mexican Arnica
Authors: Lin Long-Ze , Harnly James M.
Published: March 2019

Chamomile ( Matricaria chamomilla L.), tarragon ( Artemisia dracunculus L.) and Mexican arnica ( Heterotheca inuoides) are common compositae spices and herbs found in the US market. They contain flavonoids and hydroxycinnamates that are potentially beneficial to human health. A standardized LC-PDA-ESI/MS profiling method was used to identify 51 flavonoids and 17 hydroxycinnamates. Many of the identifications were confirmed with authentic standards or through references in the literature or the laboratory's database. More than half of the phenol compounds for each spice had not been previously reported. The phenolic profile can be used for plant authentication and to correlate with biological activities.
Secondary Metabolite Production by the Basidiomycete, Lentinus strigellus, under Different Culture Conditions
Authors: Barros-Filho Bartholomeu A. , de Oliveira Maria C. F. , Mafezoli Jair , Barbosa Francisco G. , Rodrigues-Filho Edson
Published: March 2019

The basidiomycete Lentinus strigellus was cultivated in three different culture media and the secondary metabolites produced under different culture conditions were isolated and identified. When cultivated in a liquid medium with peptone, L. strigellus afforded the benzopyrans, 2,2-dimethyl-6-methoxychroman-4-one, 4-hydroxy-2,2-dimethyl-6-methoxychromane and (3 R,4 S)-3,4-dihydroxy-2,2-dimethyl-6-methoxychromane. The indole alkaloid echinuline and the anthraquinone fiscione, both unprecedented for the genus Lentinus, were isolated from the mycelium of the fungus. When cultured in Czapek medium enriched with potato broth, the fungus afforded the same benzopyrans except (3 S,4 S)-3,4-dihydroxy-2,2-dimethyl-6-methoxychromane. Panepoxydone and isopanepoxydone were also isolated when the microorganism was grown in Czapek medium.
Structural Characterization and Biological Effects of Constituents of the Seeds of Alpinia katsumadai (Alpina Katsumadai Seed)
Authors: Nam Joo-Won , Seo Eun-Kyoung
Published: March 2019

Alpinia katsumadai Hayata (Zingiberaceae) has been used as an anti-emetic medicine and to treat gastric disorders in Oriental Medicine. Previous phytochemical investigations of this plant have resulted in the isolation of various diarylheptanoids, kavalactones, flavonoids, stilbenes, monoterpenes, and sesquiterpenes. Some of these compounds have antioxidant, anti-emetic, antiviral, and cytoprotective effects. This review paper discusses the structural characterization of the chemical constituents of A. katsumadai, as well as the biological activity of pure constituents of this plant material.
Inventory, Constituents and Conservation of Biologically Important Sumatran Plants
Authors: Arbain Dayar
Published: March 2019

An inventory of Sumatran medicinal plants, and reports on their chemistry and conservation carried out in the last three decades are reviewed.
Distinguishing between R- and S-Antcin C and Their Cytotoxicity
Authors: Lin Ting-Yu , Chien Shih-Chang , Kuo Yueh-Hsiung , Wang Sheng-Yang
Published: March 2019

Antcin C is a bioactive compound isolated from Antrodia cinnamomea, a rare and expensive medicinal fungus endemic to Taiwan. Up to date, the absolute structure of antcin C has not been solved. In this study, the phenylglycine methyl ester (PGME) derivatives of antcin C were prepared. From NMR analysis the absolute configuration of ( S)-antcin C (1) and ( R)-antcin C (2) were determined. By MTT assay, ( S)-antcin C presented cytotoxicity against Hep G2 and MCF-7 cells, with IC50 values of 14.5 and 12.8 μg/mL, respectively. However, ( R)-antcin C did not show significant cytotoxicity. Our results showed that the configuration at C25 for antcin C is very important for its cytotoxicity. From a quality control point of view, it is necessary to identify and quantify the R- and S- enantiomers in the A. cinnamomea products.
Triterpene Glycosides from the Sea Cucumber Eupentacta fraudatrix. Structure and Cytotoxic Action of Cucumariosides A2, A7, A9, A10, A11, A13 and A14, Seven New Minor Non-Sulfated Tetraosides and an Aglycone with an Uncommon 18-Hydroxy Group
Authors: Silchenko Alexandra S. , Kalinovsky Anatoly I. , Avilov Sergey A. , Andryjaschenko Pelageya V. , Dmitrenok Pavel S. , Martyyas Ekaterina A. , Kalinin Vladimir I.
Published: March 2019

Seven new minor triterpene glycosides, cucumariosides A2 (1), A7 (2), A9 (3), A10 (4), A11 (5), A13 (6) and A14 (7) have been isolated from the Far Eastern sea cucumber Eupentacta fraudatrix. Structures of the glycosides were elucidated by 2D NMR spectroscopy and MS. Glycosides 1–7 belong to the group of cucumariosides A, having linear tetrasaccharide carbohydrate moieties without any sulfate group and possessing 3- O-methyl-D-xylose as a terminal monosaccharide unit. Glycosides 1, 2, 5-7 differ from each other in side chain structures in aglycone moieties, while cucumarioside A10 (4) has a 23,24,25,26,27-pentanorlanostane aglycone with 18(16)-lactone. Cucumarioside A9 (3), having an uncommon 18-hydroxy group, is the second representative of the unique metabolically active glycosides that are regarded as intermediates of glycoside biosynthesis in sea cucumbers. Cytotoxic activities of glycosides 1–7 and cucumarioside A8 (8) against mouse spleen lymphocytes and the cells of the ascite form of mouse Ehrlich carcinoma, along with hemolytic activity against mouse erythrocytes and antifungal activity were studied. Cucumariosides A2 (1), A8 (8) and A13 (6) demonstrated high hemolytic activities. Glycosides 1, 4 and 6 showed moderate cytotoxic activity. Only cucumarioside A8 (8), having an 18-oxymethylene group and a 24(25)-double bond, was very active in all the tests.
Two New Asterosaponins from the Far Eastern Starfish Lethasterias fusca
Authors: Ivanchina Natalia V. , Kalinovsky Anatoly I. , Kicha Alla A. , Malyarenko Timofey V. , Dmitrenok Pavel S. , Ermakova Svetlana P. , Stonik Valentin A.
Published: March 2019

Two new asterosaponins, lethasteriosides A (1) and B (2), were isolated along with previously known thornasteroside A (3), anasteroside A (4), and luidiaquinoside (5) from the ethanolic extract of the Far Eastern starfish Lethasterias fusca. The structures of the new compounds were elucidated by extensive NMR and ESIMS techniques, and chemical transformations. Compounds 1 and 3–5 did not show any apparent cytotoxicity against cancer cell lines T-47D, RPMI-7951, and HCT-116, but glycoside 1, at concentration of 20 μM, demonstrated considerable inhibition of the T-47D (97%), RPMI-7951 (90%) and HCT-116 (90%) cell colony formations in a soft agar clonogenic assay.
Improved Method for Isolation of Lycopsamine from Roots of Comfrey (Symphytum officinale)
Authors: Janeš Damjan , Kalamar Boštjan , Kreft Samo
Published: March 2019

An improved method for the isolation and purification of pyrrolizidine alkaloids from comfrey ( Symphytum officinale L.) roots was developed, introducing very fast, selective and ion residue-free reduction of N-oxides followed by ion-exchange chromatography giving a non-aqueous solution of alkaloids, from which solvents can be easily removed. With this procedure the use of large volumes of organic solvents, very slow reduction of N-oxides and input of additional impurities was avoided. Lycopsamine, which proved to be the major alkaloid, was additionally purified by preparative layer chromatography (PLC) and high performance liquid chromatography (HPLC). The identity of the alkaloid was confirmed by 1H NMR spectroscopy and mass spectrometry.
Anticomplement and Antimicrobial Activities of Flavonoids from Entada phaseoloides
Authors: Li Ke , Xing Shihua , Wang Mengyue , Peng Ying , Dong Yuqiong , Li Xiaobo
Published: March 2019

Seventeen flavonoids isolated from the extracts of the stem of Entada phaseoloides were investigated for their anticomplement (both classic and alternative pathways) and antimicrobial activities against Gram-positive bacteria (MRSA, MSSA, Standard Enterococcus and Bacillus subtilis), Gram-negative bacteria ( Escherichia coli, Pseudomonas aeuroginosa) and the yeast-like pathogenic fungus Candida albicans. The anticomplement studies revealed a dose-dependent activity among isolated quercetin, luteolin, apigenin, galangin, 5,2′,5′-trihydroxy-3,7,4′-trimethoxyflavone-2′-O-β-D-glucoside (+)-3,3′,5′,5,7-pentahydroflavanone, (+)-dihydrokaempferol, (-)-epicatechin, (+)-catechin, naringenin, and 5,7,3′,5′-tetrahydroxyflavanone, and the antimicrobial results indicated that quercetin, 5,7,4′-trihydroxy-3′-methoxyflavonol and galangin produced the inhibitory activities against MRSA, MSSA, and Standard Enterococcus, while luteolin and rhamnocitrin displayed inhibition against only MRSA and MSSA. To the best of our knowledge, this is the first report that describes the anticomplement and antimicrobial activities of the stem of E. phaseoloides.
Quality Control and Analytical Test Method for Taxus baccata Tincture Preparation
Authors: Vignolini Pamela , Gehrmann Beatrice , Melzig Matthias Friedrich , Borsacchi Leonardo , Scardigli Arianna , Romani Annalisa
Published: March 2019

The homeopathic tincture of Taxus baccata L. is monographed in the current German Homeopathic Pharmacopoeia (HAB 2009). However, the described identification test is a common comparative TLC procedure that might be updated. The purpose of the current work was the quali-quantitative analysis by HPLC/DAD/MS of Taxus tincture. In this study we characterized polyphenolic compounds, in particular four hydroxycinnamic derivatives (0.85 mg/mL) and four flavonoids (quercetin and kaempferol 3- O-rutinoside and xylosyl glucosides); the total polyphenol content was 1.265 mg/mL of tincture. Starting from the official German Homeopathic Pharmacopoeia method of preparation, the aim of this work was to optimize a rapid and reproducible method for the analysis of herbal drugs and tincture, directly prepared in store or the herbalist's shop, to ensure safety and efficacy of the preparation. The procedure has to ensure validation, robustness of the results, and provide a quick response about the composition of compounds in the herbal drug preparation.
Chalcones in Bioactive Argentine Propolis Collected in Arid Environments
Authors: Solórzano Eliana , Vera Nancy , Cuello Soledad , Ordoñez Roxana , Zampini Catiana , Maldonado Luis , Bedascarrasbure Enrique , Isla María I.
Published: March 2019

The aim of this study was to assess the chemical and biological profile of propolis samples collected in arid environments of north-western Argentina. The samples were from two phytogeographical regions (Prepuna and Monte de Catamarca Province). Propolis ethanolic extracts (PEE) and chloroform (CHL), hexane (HEX) and aqueous (AQ) sub-extracts of samples from three regions (CAT-I; CAT-II and CAT-III) were obtained. All PEE exhibited antioxidant activity in the DPPH radical scavenging assay (SC50 values between 28 and 43 μg DW/mL). The CHL extract was the most active (SC50 values between 10 and 37 μg DW/mL). The antioxidant activity in the β-carotene bleaching assays was more effective for PEE and CHL (IC50 values between 2 and 9 μg DW/mL, respectively). A similar pattern was observed for antibacterial activity. The highest inhibitory effect on the growth of human Gram-positive bacteria was observed for CHL-III and CHL-I (Monte region) with minimal inhibitory concentration values (MIC100) of 50 to 100 μg DW/mL. Nine compounds were identified by HPLC-PAD. Two of them (2′,4′-dihydroxychalcone and 2′,4′- dihydroxy 3′-methoxychalcone) were found only in propolis samples from the Monte phytogeographical region. We consider that the Argentine arid region is appropriate to place hives in order to obtain propolis of excellent quality because the dominant life forms in that environment are shrubby species that produce resinous exudates with a high content of chalcones, flavones and flavonols.
Biotransformation of Salvianolic acid B by Fusarium oxysporum f. sp. Cucumerinum and Its Two Degradation Routes
Authors: Kan Shidong , Lin Huimin , Li Ji'an , Shao Lei , Chen Daijie
Published: March 2019

Resting cells of Fusarium oxysporum f. sp. Cucumerinum ( F. oxsporum) were used for the biotransformation of salvianolic acid B (Sal B). Three transformed products, isolithospermic acid, prolithospermic acid and danshensu, were identified on the basis of chemical and spectroscopic data. The stability of the two ester bonds of Sal B was studied and two degradation routes were found. In the biotransformation system, Sal B was transformed into isolithospermic acid first which was then converted into prolithospermic acid. In alkaline solutions, Sal B was transformed into lithospermic acid first which was then converted into prolithospermic acid. This is the first reports of the NMR spectra of isolithospermic acid and this result may indicate the metabolic pathways of Sal B in vivo.
c-AMP Dependent Protein Kinase a Inhibitory Activity of Six Algal Extracts from South Eastern Australia and Their Fatty Acid Composition
Authors: Zivanovic Ana , Skropeta Danielle
Published: March 2019

c-AMP Dependent protein kinase (protein kinase A, PKA) is an important enzyme involved in the regulation of an increasing number of physiological processes including immune function, cardiovascular disease, memory disorders and cancer. The objective of this study was to evaluate the PKA inhibitory activity of a range of algal extracts, along with their fatty acid composition. Six algal species were investigated including two Chlorophyta ( Codium dimorphum and Ulva lactuca), two Phaeophyta ( Phyllospora comosa and Sargassum sp.) and two Rhodophyta ( Prionitis linearis and Corallina vancouveriensis), with the order of PKA inhibitory activity of their extracts identified as follows: brown seaweeds > red seaweeds > green seaweeds with the brown alga Sargassum sp. exhibiting the highest PKA inhibitory activity (84% at 100 μg/mL). GC/MS analysis identified a total of 18 fatty acids in the six algal extracts accounting for 72-87% of each extract, with hexadecanoic acid and 9,12-octadecadienoic acid as the dominant components. The most active extract ( Sargassum sp.) also contained the highest percentage of the saturated C14:0 fatty acid (12.8% of the total extract), which is a known to inhibit PKA. These results provide the first description of the PKA inhibitory activity of marine algae along with the first description of the fatty acid composition of these six algal species from South Eastern Australian waters. Importantly, this study reveals that abundant and readily available marine algae are a new and relatively unexplored source of PKA inhibitory compounds.
Essential Oil Composition of Prasium majus from Croatia
Authors: Jerković Igor , Šuste Marko , Maleš Željan , Pilepić Kroata Hazler
Published: March 2019

The essential oils from the aerial parts of Prasium majus L., collected during two years in Croatia, were analysed by GC and GC/MS. Fifty-two compounds were identified, representing 90.3–91.8% of the total oils. The major constituents in both samples were fatty acids (particularly hexadecanoic acid and ( Z)-octadec-9-enoic acid), lower aliphatic alcohols, aldehydes and acids (major ones oct-1-en-3-ol and ( E,E)-hepta-2,4-dienal) and phenylpropane derivatives (e.g. eugenol). β-Caryophyllene was the most abundant terpene and ( E)-β-ionone was the major norisoprenoid.
In vitro Antimicrobial Properties and Chemical Composition of Santolina chamaecyparissus Essential Oil from Algeria
Authors: Djeddi Samah , Djebile Khadidja , Hadjbourega Ghania , Achour Zoubida , Argyropoulou Catherine , Skaltsa Helen
Published: March 2019

The chemical composition of the essential oil obtained from the aerial parts of Santolina chamaecyparissus L., growing in Algeria, was investigated by GC-MS analyses. A total of 36 compounds were identified, accounting for 91.7% of the essential oil obtained. Camphor (31.1%) and cubenol (17.0%) were the predominant compounds. The potential of the antimicrobial activity was also investigated and the tested sample proved to be very active against Klebsiella pneumonia and Candida albicans (34.1 ± 0.02 mm and 35.0 ± 0.01 mm, respectively). Transverse sections of the leaf and stem of the plant suggest that the essential oil is localized in endogenous and exogenous sites.
Chemical Composition and in vitro Antimicrobial Activity of the Essential Oil of the Flowers of Tridax procumbens
Authors: Joshi Rajesh K. , Badakar Vijaylaxmi
Published: March 2019

The essential oil of the flowers of Tridax procumbens L. was obtained by hydro-distillation and analyzed by gas chromatography equipped with a flame ionization detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC/MS). Twenty-six compounds were identified, which comprised 90.6% of the total constituents. The most abundant compound was ( Z)-falcarinol (25.9%), followed by α-selinene (15.3%), limonene (8.3%) and zerumbone (4.3%). Antimicrobial activity was tested against six Gram-positive and eight Gram-negative bacteria, and three fungi. The oil was active against the tested Gram-positive bacteria at a concentration range of 0.14 ± 0.03 - 0.57±0.05 mg/mL, while 0.67 ± 0.12 - 4.58 ± 0.41 mg/mL was effective against the studied Gram-negative bacteria. Remarkable antifungal activity was found against the tested fungi at a concentration range of 0.06 ± 0.008 - 0.10 ± 0.01 mg/mL.
Terpenoids from Cichorium intybus
Authors: Zhou Chang-Xin , Zou Li , Zhao Zong-Zheng , Zhu Hong , He Qiao-Jun , Yang Bo , Gan Li-She
Published: March 2019

A new sesquiterpenoid, 1α,5α-epoxy-4α-hydroxyl-4β,10β-dimethyl-7αH,10αH-guaia-11(13)-en-12-oic acid (1), and four known compounds, lactucin (2), 1β-hydroxy-7αH,8,11βH-eudesm-3-en-8,12-olide (3), 13,14- seco-stigma 9(11),14(15)-dien-3α-ol (4), and bacosterol-3- O-β-D-glucopyranoside (5) were isolated from Cichorium intybus L. Their structures were determined on the basis of detailed analysis of their 1D- and 2D-NMR spectroscopic and mass spectrometric data. Compounds 2 and 4 showed strong activities against the A2780 cell line with IC50 values of 1.81 and 0.07 μM, respectively.
(6R,9S)-6″-(4″-Hydroxybenzoyl)-Roseoside, a New Megastigmane Derivative from Ouratea polyantha and its Effect on Hepatic Glucose-6-phosphatase
Authors: Bermúdez Jairo , Rodríguez María , Hasegawa Masahisa , González-Mujica Freddy , Duque Sandra , Ito Yoichiro
Published: March 2019

A new megastigmane derivative, (6 R,9 S)–6′-(4″-hydroxybenzoyl)-roseoside (1) and two known compounds, the biflavoneagathisflavone (2) and 4-hydroxy-benzoic acid (3) were isolated and purified from leaves and stems of Ouratea polyantha Engl. Agathisflavone was isolated in a single high-speed counter-current chromatography run, while the megastigmane was purified in two steps, by using a combination of high-speed countercurrent chromatography and analytical column chromatography. All structures were elucidated on the basis of spectral evidence and comparison with literature data. Compound 1 was characterized by [α]D20, UV-Vis, IR, MS, 1H NMR, 13C NMR, HMQC, HMBC, COSY and NOESY. Compounds 1 and 2 showed an inhibitory effect of 63.6 and 13.7% on the G-6-Pase intact microsomes, respectively.
Anti-proliferative Activity and Apoptotic Potential of Britannin, a Sesquiterpene Lactone from Inula aucheriana
Authors: Moghadam Maryam Hamzeloo , Hajimehdipoor Homa , Saeidnia Soodabeh , Atoofi Azadeh , Shahrestani Roxana , Read Roger W. , Mosaddegh Mahmoud
Published: March 2019

Inula aucheriana n-hexane, CHCl3 and MeOH extracts were evaluated for their anti-proliferative activity against HepG-2, MCF-7, MDBK and A-549 cells. The CHCl3 extract exhibited cytotoxic activity to the above cell lines with IC50 values of 13.5, 23.4, 10.5, and 26.9 μg/mL, respectively. The sesquiterpene lactone britannin was isolated from the above extract. This was further evaluated in the MTT assay to demonstrate strong cytotoxicity to the mentioned cell lines (IC50: 2.2, 5.9, 5.4, and 3.5 μg/mL, respectively), and the apoptotic inducing properties of britannin were evaluated on human breast adenocarcinoma (MCF-7) cells through the terminal deoxynucleotidyl transferase dUTP nick end labeling (TUNEL) assay.
Bio-assay Guided Isolation of α-Glucosidase Inhibitory Constituents from Eclipta alba
Authors: Kumar Deepak , Gaonkar Raghuvir H. , Ghosh Rina , Pal Bikas C.
Published: March 2019

Eclipta alba (L.) Hassk is used traditionally in diabetes mellitus in India and the plant extract is reported to possess anti-diabetic activity. A bioactivity-guided isolation approach based on α-glucosidase inhibition was used to identify the constituents contributing towards the inhibition of the enzyme and probably contributing towards its anti-diabetic activity. Four echinocystic acid glycosides were thus isolated, of which eclalbasaponin VI, isolated from the n-butanol fraction, was found to be the most potent (IC50 54.2 ± 1.3 μM). The compound is an uncompetitive type of inhibitor with Ki 26.1 μM. A quantitative estimation of the constituents was established using RP-HPLC.
Furostanol Saponin and Diphenylpentendiol from the Roots of Asparagus racemosus
Authors: Sharma Upendra , Kumar Neeraj , Singh Bikram
Published: March 2019

A new furostanol steroidal saponin, shatavaroside C (1), and a new diphenylpentendiol, shatavarol (2), together with five known compounds, shatavarin IV (3), racemoside A (4), β-sitosterol (5) stigmasterol (6) and ursolic acid (7), have been isolated from the roots of Asparagus racemosus. This is the first report on the isolation of racemoside A (4) from roots of the plant. Structures of isolated compounds were determined on the basis of detailed analysis of their 1D, 2D NMR and mass spectral data.