bluuebunny/crossref_metadata_2025 huggingface dataset:
Cytotoxic Activity of Some Lupeol Derivatives
Authors: Bednarczyk-Cwynar Barbara , Wiȩcaszek Tomasz , Ruszkowski Piotr
Published: March 2019

The synthesis of 3- O-acyl derivatives of lupeol is presented, as well as lupenone and the oxime of lupenone. The obtained derivatives were subjected to the MTT test in order to evaluate their cytotoxic activity toward HeLa, KB, MCF-7 and A-549 cell lines in comparison with lupeol (1). The IC50 values for lupeol (1) and all of the tested derivatives (2–6) were from about 7–10 μM for lupenone (5) to about 81 μM for o-phthaloyl-lupeol (4). Acylation of the C-3 hydroxy function of compound 1 decreased the cytotoxic activity of compounds 2–4. The most active anticancer agent was lupenone (5), with IC50 values 7.1–9.1 μM in comparison with 37.7–51.9 μM for lupeol (1).
Regulusosides A, B, and C, Three New Polyhydroxysteroid Glycosides from the Starfish Pentaceraster regulus
Authors: Kicha Alla A. , Ivanchina Natalia V. , Malyarenko Timofey V. , Kalinovsky Anatoly I. , Dmitrenok Pavel S. , Pislyagin Evgeny A. , Yurchenko Ekaterina A.
Published: March 2019

Three new polyhydroxysteroid glycosides, regulusosides A-C (1-3) along with the previously known five steroid compounds (4-8) were isolated from the tropical starfish Pentaceraster regulus. The structures of compounds 1-3 were established by extensive NMR and ESI-MS techniques. New glycosides have the same aglycon, (24 S)-5α-cholestane-3β,5,6β,8,15α,24-hexol, and various disaccharide moieties: β-D-xylopyranosyl-(1→2)-3- O-methyl-α-L-arabinofuranosyl (1), β-D-xylopyranosyl-(1→2)-α-L-arabinofuranosyl (2), and 2- O-methyl-β-D-xylopyranosyl-(1→2)-3- O-methyl-α-L-arabinofuranosyl (3), attached at C-24 of the side chain. Compounds 1, 2 and 6 exhibit potential immunomodulatory properties, inducing intracellular ROS (reactive oxygen species) formation in the RAW 264.7 murine macrophage cells.
Unusual Steroid Constituents from the Tropical Starfish Leiaster sp
Authors: Malyarenko Timofey V. , Kicha Alla A. , Ivanchina Natalia V. , Kalinovsky Anatoly I. , Dmitrenok Pavel S. , Stonik Valentin A.
Published: March 2019

Two polar steroid compounds, taurochenodeoxycholic acid sodium salt (1) and a rare cyclic steroid glycoside luzonicoside A (2), were isolated from the tropical starfish Leiaster sp. and identified by extensive NMR and ESIMS techniques. The isolation of primary bile acid 1 is the first report from a representative of the class Asteroidea and on the whole in invertebrates. Its presence confirms the hypothesis about the digestive role of some polar steroids in starfish and possibly demonstrates the parallel evolution of fat emulsifying agents in vertebrates and some starfish. Compound 2 was also obtained from starfish belonging to this genus for the first time. This finding indicates that cyclic steroid glycosides are more widely distributed in starfish than the two species of the genus Echinaster from which they were isolated earlier.
Multifunctional Monoamine Oxidases and Cholinesterases Inhibitory Effects, as well as UPLC-DAD-MS Chemical Profile of Alkaloid Fractions Obtained from Species of the Palicoureeae Tribe
Authors: Klein-Júnior Luiz Carlos , Passos Carolina dos Santos , Salton Juliana , Bitencourt de Fernanda Gobbi , Funez Luís , de Andrade Jean Paulo , Villalobos Jonathan Parra , de Loreto Bordignon Sérgio Augusto , Gasper André Luís , Heyden Yvan Vander , Henriques Amélia Teresinha
Published: March 2019

In the present study, the effects were evaluated of alkaloid fractions (AFs) from Psychotria species and correlated genera, Palicourea and Rudgea, on monoamine oxidases (MAOs) and cholinesterases (ChEs). By HPLC-DAD and UPLC-DAD-MS analyses, indole alkaloids (IA) were detected in all AFs. For the Psychotria and Palicourea species, these IA corresponded to tetrahydro-β-carboline alkaloids (THβCA). On the other hand, pyrrolidinoindoline core compounds were observed for Rudgea species. Regarding their pharmacological activities, none of the AFs was able to inhibit AChE. However, the BChE activity was impaired by the Psychotria and Palicourea AFs. In addition, MAO-A was inhibited by both AFs, but only Psychotria nemorosa AF was able to inhibit significantly MAO-B. Rudgea AFs demonstrated a poor inhibitory profile on MAO-A. Taken together, our results highlighted the Psychotria and Palicourea genera as important sources of scaffolds for the development of MAO-A and BChE inhibitors aiming at the treatment of neurodegenerative and neuropsychiatric diseases.
Flavonoids from the Bark of Artocarpus integer var. silvestris and their Anti-inflammatory Properties
Authors: Shah Masuri Kama Kamaruddin , Sirat Hasnah Mohd , Jamil Shajarahtunnur , Jalil Juriyati
Published: March 2019

A new pyranoflavone, methoxycyclocommunol (1) together with four known flavonoids, artonin F (2), heteroflavanone A (3), cudraflavone C (4) and cyclocommunol (5) were isolated from the bark of Artocarpus integer var. silvestris Corner. Their structures were elucidated through extensive spectroscopic techniques (UV, IR, MS, 1D-NMR and 2D-NMR) and by comparison with literature data. All the pure compounds were tested for their anti-inflammatory activities by using screening kit and radioimmunoassay methods. In a 15-lipoxygenase (15-LOX) inhibitory assay, compounds 1, 2, 4 and 5 gave weak percentages of inhibition, 16.5, 18.3, 17.6, 10.2%, respectively at the concentration of 100 μM. Compounds 1, 3 and 4, however, showed strong dose-dependent inhibition towards prostaglandin E2 (PGE2) production in lipopolysaccharide-induced human whole blood using a radioimmunoassay method with IC50 values of 4.3, 0.8, and 0.07 μM, respectively suggesting that they strongly exhibited cyclooxygenase-2 (COX-2) activity.
A New Flavonoid from Camellia sinensis Fermented Tea
Authors: Usui Ayaka , Nakamura Azusa , Era Manami , Matsuo Yosuke , Tanaka Takashi , Ishimaru Kanji
Published: March 2019

A new flavonoid, quercetin 3- O-α-L-rhamnopyranosyl-(1→6)-(2- E- p-coumaroyl)-β-D-glucopyranoside-4′- O-α-L-rhamnopyranoside, was isolated from the fermented tea of Camellia sinensis L. (Pu-erh tea) from China. The chemical structure was elucidated based on analyses of the spectroscopic data.
Effect of Auxins on Anthocyanin Accumulation in Hairy Root Cultures of Tartary Buckwheat Cultivar Hokkai T10
Authors: Park Chang Ha , AyeThwe Aye , Kim Sun Ju , Park Jong Seok , Arasu MariadhasValan , Al-Dhabi Naif Abdullah , Park Nam Il , Park Sang Un
Published: March 2019

This study investigated the influence of auxins on the growth of hairy roots and accumulation of anthocyanins, including cyanidin 3- O-glucoside (C3gl) and cyanidin 3- O-rutinoside (C3r), in the hairy root culture of tartary buckwheat cultivar Hokkai T10. C3gl and C3r contents were evaluated using highperformance liquid chromatograph (HPLC). Four auxins, 2,4-dichlorophenoxyacetic acid (2,4-D), indoleacetic acid (IAA), indolebutyric acid (IBA) and naphthaleneacetic acid (NAA), were added to the medium of the hairy root cultures at diverse concentrations. IAA, IBA and 2,4-D promoted the growth of hairy roots since the dry weight of the roots was slightly higher than or comparable with that of the control. However, NAA at all concentrations suppressed the growth of hairy roots. Generally, auxin treatments resulted in higher accumulation of C3gl and C3r than that of the control except for 2.85 μM IAA and 2.69 μM NAA. The amount of C3gl and C3r after treatment with 4.92 μM IBA was the highest among all treatments and was 3.24 times more than that of the control. Our results suggested that auxins at appropriate concentrations might facilitate hairy root growth of tartary buckwheat and enhance the production of C3gl and C3r.
Inhibitory Effects of Echinochrome A, Isolated from Shell of the Sea Urchin Anthocidaris crassispina, on Antigen-Stimulated Degranulation in Rat Basophilic Leukemia RBL-2H3 Cells through Suppression of Lyn Activation
Authors: Itoh Tomohiro , Fujiwara Azusa , Ninomiya Masayuki , Maeda Toshimichi , Ando Masashi , Tsukamasa Yasuyuki , Koketsu Mamoru
Published: March 2019

Echinochrome A (Echi-A) was isolated from the sea urchin Anthocidaris crassispina and its structure determined using 1D and 2D-NMR. In the present study, we examined the inhibitory effect of Echi-A on antigen-stimulated degranulation in rat basophilic leukemia RBL-2H3 cells, which were suppressed in a dose dependent manner. The antigens bind to the high affinity immunoglobulin E receptor, which is expressed on the surface of mast cells and basophils and activate intracellular signal transduction, resulting in the release of biologically active mediators such as histamine. In order to disclose the inhibitory mechanisms of degranulation by Echi-A, we examined the elevation in intracellular Ca2+ concentration ([Ca2+]i), production levels of intracellular reactive oxygen species (ROS) and early intracellular signaling events. Both elevation of [Ca2+]i and intracellular ROS production were markedly suppressed in cells treated with Echi-A. Echi-A also suppressed the activation of Lyn, Syk, and PLCγ1/2 in antigen-stimulated cells. These results indicated that inhibition of antigen-stimulated degranulation in RBL-2H3 cells by Echi-A is mainly due to the inactivation of Lyn/Syk/PLCγ signaling pathways. Our findings suggest that Echi-A could be a beneficial agent for alleviating the symptoms of type I allergy.
Preparative Synthesis of Spinochrome D, a Pigment of Different Sea Urchin Species
Authors: Shestak Olga P. , Balaneva Nadezhda N. , Novikov Vyacheslav L.
Published: March 2019

A simple and effective synthesis of spinochrome D (1) (2,3,5,6,8-pentahydroxy-1,4-naphthoquinone), a pigment of different sea urchin species, has been developed starting from 2,3-dichloro-5,8-dihydroxy-1,4-naphthoquinone (13), easily available by cycloacylation of 1,4-dimethoxybenzene (11) with dichloromaleic anhydride (12). Bromination of 13 with either bromine or dioxane dibromide to 6-bromo-2,3-dichloro-5,8-dihydroxy-1,4-naphthoquinone (21), followed by nucleophilic substitution of the halogen atoms by methoxy groups in 21 and hydrolysis of trimethyl ether 10 produce the target compound in overall yield from 62 to 65%.
Structural Elucidation and Free Radical Scavenging Activity of a new o-Orsellinic Acid Derivative Isolated from the Lichen Cladonia rappii
Authors: Lage Tiago C.A. , Horta Lívia P. , Montanari Ricardo M. , Silva Jefferson G. , de Fátima Ângelo , Fernandes Sergio A. , Modolo Luzia V.
Published: March 2019

Rappiidic acid, a new o-orsellinic acid derivative, was isolated from the lichen Cladonia rappii. Its capability to scavenge reactive oxygen species (ROS) and reactive nitrogen species (RNS) was investigated and compared with resveratrol and (+)-usnic acid. Usnic acid at 100 μM was the most efficient ROS scavenger, exhibiting activity 3-fold higher than that of resveratrol. At the same concentration, rappidic acid scavenged 23.1% of ROS formed, demonstrating that this compound is twice as active as resveratrol. Both compounds were shown to be poor RNS scavengers.
Phenanthrenes in Chinese Yam Peel Exhibit Anti-inflammatory Activity, as Shown by Strong in Vitro Cyclooxygenase Enzyme Inhibition
Authors: Li Qian , Zhang Chuan-Rui , Dissanayake Amila A. , Gao Qun-yu , Nair Muraleedharan G.
Published: March 2019

Chinese yam ( Dioscorea opposita), peeled or whole, is a popular food item that is considered to be healthy. Often, the yam is peeled before cooking. However, it is also consumed with peel. Therefore, in this study, the peel of this yam was extracted sequentially with n-hexane, ethyl acetate and methanol, and studied for its health-benefits, using in vitro bioassays. Bioactivity-guided purifications of extracts of the peel afforded phenanthrenes (1-4), as characterized by spectroscopic methods. Phenanthrene 1 is a novel analogue. The extracts and isolates were tested for anti-inflammatory activity using cyclooxygenase enzyme (COX-1 and -2) inhibitory assays. All phenanthrenes isolated from the yam peel showed higher inhibition of COX enzymes than the over-the-counter nonsteroidal anti-inflammatory drugs (NSAIDs) aspirin, ibuprofen and naproxen.
In vitro Antigonorrhea Activity of the Aerial Part of Asparagus suaveolens n-Hexane Fraction and Palmitone as a Bioactive Compound
Authors: Olivier Mutendela Tabize , Muganza Freddy Munyololo , Shai Leshweni Jeremia , Gololo Stanley Sechene
Published: March 2019

Asparagus suaveolens is a medicinal plant used in Lesotho and South Africa to treat epilepsy and gonorrhea. The current investigation identifies the compound responsible for the antiepileptic and antimicrobial properties as palmitone which showed antigonorrhea activities against WHO 2008 Neisseria gonorrhea F and O strains more than the standard used, gentamicin. These results support the traditional use of A. suaveolens for treatment of gonorrhea and epilepsy since palmitone is known as an anticonvulsant agent. This is the first study indicating the presence of palmitone in the Asparagus genus and demonstrates the in vitro antigonorrhea activity of palmitone.
Compositional Variability and Toxic Activity of Mugwort (Artemisia vulgaris) Essential Oils
Authors: Judzentiene Asta , Garjonyte Rasa
Published: March 2019

The compositional variability of the essential oils of aerial parts of mugwort ( Artemisia vulgaris L.), collected from fifteen wild populations in Lithuania is detailed. The most predominant components were davanones (13.8-45.5%, six oils), germacrene D (9.1-30.5%, four oils), 1,8-cineole (16.4%, one oil), camphor (18.9%, one oil), trans-thujone (8.9 and 10.9%, two oils) and cis-chrysanthenyl acetate (10.4%, one oil). To the best of our knowledge, the davanone chemotype for A. vulgaris oils is described for the first time. The toxicity of the mugwort essential oils was determined using brine shrimp ( Artemia sp.) assay. LC50 values (10.3-23.1 μg/mL) obtained for the oils after 24 h of exposure revealed that the oils containing appreciable amounts of germacrene D, 1,8-cineole, camphor and davanone were notably toxic.
Analgesic Activity of Novel GABA Esters after Transdermal Delivery
Authors: Nesterkina Mariia , Kravchenko Iryna
Published: March 2019

Analgesic activity of novel GABA esters with l-menthol (1), thymol (2), carvacrol (3) and guaiacol (4) was investigated by pharmacological models of thermal and chemical stimuli in mice after topical application in an ointment (2% w/w). The initial terpenes – l-menthol (5), thymol (6), carvacrol (7) and guaiacol (8) have also been studied under the same experimental conditions. All studied compounds were found to produce an antinociceptive effect in both thermal- and chemical-induced models of acute pain after their topical application. In the hot plate test, compound 1 demonstrated maximum analgesic activity and attenuated acute pain more than the reference drug BZC. GABA esters with l-menthol (1) and carvacrol (3), as well as l-menthol (5) itself exhibited analgesic activity which is the same or better in comparison with benzocaine in chemical-stimulated models of pain caused by either formalin or capsaicin.
Synthesis and Antimicrobial Activity of Calycanthaceous Alkaloid Analogues
Authors: Zheng Shaojun , Li Longbo , Wang Yu , Zhu Rui , Bai Hogjin , Zhang Jiwen
Published: March 2019

A series of 24 novel derivatives of the calycanthaceous alkaloids with a tetrahydropyrroloindol-based core structure was synthesized from tryptophan in good yields. Their structures were characterized by IR, 1H NMR, and 13C NMR spectroscopy and ESI-MS. The synthesized compounds were evaluated against a wide variety of plant pathogenic fungi. Compound a9 exhibited a high degree of activity against Curvularia lunata, with 91.0% activity at a concentration of 100 μg mL−1 and with an EC50 of 44.6 μg mL−1. a7, a8, a13, and a17 exhibited high degrees of activity against Sclerotinia sclerotiorum, with a8 being the most effective with an EC50 of 38.4 μg mL−1. Compound a9 illustrated activity against Botrytis cinerea, with an EC50 of 79.5 μg mL−1. Considering the compounds evaluated, the alkyl substituents of the chain may contribute to the significant variations in fungicidal potency. The structure antifungal activity relationships are also discussed. These results will pave the way for further design, structural modification, and development of calycanthaceous alkaloids as antimicrobial agents.
Evaluation of Antioxidant Interactions of Combined Model Systems of Phenolics in the Presence of Sugars
Authors: Kopjar Mirela , Lončarić Ante , Mikulinjak Mateja , Šrajbek Žaklina , Šrajbek Mihaela , Pichler Anita
Published: March 2019

The aim of this study was to determine the antioxidant activity of model systems of phenolics (individual and combinations) without and with the addition of sugars (sucrose or trehalose). Also, the synergistic or antagonistic effects of the phenolics in all model systems were evaluated. The results for the antioxidant activity were obtained by three assays, ABTS+•, DPPH• and FRAP. ABTS+• and DPPH• assay showed that quercetin and gallic acid had the same antioxidant activity, higher than catechin. When the FRAP assay was applied, the order of increasing of antioxidant activity was quercetin < gallic acid < catechin. The highest synergistic effect was achieved in the model system of catechin, quercetin and gallic acid. Addition of sugars, sucrose and trehalose, influenced both antioxidant activity and synergistic effect of phenolics in the model systems. The highest synergistic effect in the model systems with sucrose addition was observed with catechin, quercetin and gallic acid, while in samples with trehalose, the highest synergistic effect was in combination with catechin and gallic acid. Interactions of phenolics and phenolics/sugars caused changes in antioxidant activity as well as synergistic effects.
Altitude Variation in the Composition of Essential Oils, Fatty Acid Methyl Esters, and Antimicrobial Activities of Two Subspecies of Primula vulgaris Grown in Turkey
Authors: Yaylι Nurettin , Tosun Gonca , Yaylι Büşra , Gündoğanc Zeynep , Coşkunçelebic Kamil , Karaoğlu Şengül Alpay
Published: March 2019

In this study, the changes caused by variation of altitude to the essential oils (EOs), fatty acid methyl esters (FAMEs), and antimicrobial activities of Primula vulgaris Huds. subsp. vulgaris ( Pvv) and P. vulgaris Huds. subsp. sibthorpii (Hoffmanns) W.W. Sm. & Forrest ( Pvs)) grown in Turkey were investigated. Major fluctuations in the composition of Pvv and Pvs oils included methyl-4-methoxy salicylate (4.5–35.3%; Pvv and 3.2–37.2%; Pvs), ( Z,Z,Z)-7,10,13-hexadecatrienal (5.1–21.8%; Pvv and 4.4–15.2%; Pvs) and flavone (5.5–14.9%; Pvv and 1.6–18.0%; Pvs). Fatty acid profile (C6:0–C26:0) changes were noted in Pvv and Pvs. Methyl hexadecanoate (2.4–9.3%) and methyl octadecanoate (1.0–4.7%) were present in all the FAME samples of the plants. The antimicrobial activity of the EOs of Pvv and Pvs were tested against nine bacterial species, which showed activity against Mycobacterium smegmatis with minimum inhibitory concentrations (MIC) varying from 8.5 to 59.2 μg/mL in all samples, respectively, depending on the altitude at which the oils were obtained.
Chemical Composition of Fruit Essential Oil of Endemic Malabaila pastinacifolia
Authors: Tabanca Nurhayat
Published: March 2019

The water distilled essential oil (EO) from the fruits of Malabaila pastinacfolia Boiss & Balansa (Apiaceae), an endemic species from Turkey, was analyzed using GC-FID and GC-MS systems. The analysis revealed 38 compounds accounting for 97.6% of the EO. Hexyl butyrate (47.2 %), hexyl hexanoate (22.7%) and α-terpinyl acetate (11.1 %) were found as the main constitutes. This is the first report on the EO composition of M. pastinacfolia.
Chemical Composition and Biting Deterrent Activity of Essential Oil of Tagetes patula (Marigold) against Aedes aegypti
Authors: Ali Abbas , Tabanca Nurhayat , Amin Elham , Demirci Betul , Khan Ikhlas A.
Published: March 2019

The hydrodistilled leaf essential oil (EO) of Tagetes patula L. was analyzed by GC-FID and GC-MS. The main components of the oil were characterized as caryophyllene oxide (18.4%), β-caryophyllene (18.0%) and spathulenol (9.1%). The EO was screened for its biting deterrent activity against Aedes aegypti L. using the in vitro K&D module system. T. patula EO exhibited good biting deterrent activity. The results suggest that these sesquiterpenes may contribute to biting deterrent activity, but the role of minor components cannot be excluded. T. patula EO also showed 100, 90 and 10% mortality at dosages of 125, 62.5 and 31.25 ppm, respectively, in 1-day-old larvae of Ae. aegypti.
Larvicidal Activity of Essential Oil Constituents against Malaria Vector, Anopheles gambiae (Diptera: Culicidae)
Authors: Lima Tamires Cardoso , Kweka Eliningaya J. , Marciale Chrian M. , de Sousa Damião Pergentino
Published: March 2019

Malaria is one of the most important public health problems worldwide. This illness is controlled, mainly, by combating the vector mosquitoes using chemical insecticides, but this use has caused environmental impact and the emergence of tolerance in adult mosquitoes. Herein, we report the larvicidal activity of nine chemical constituents found in essential oils against third-instar larvae of Anopheles gambiae. All the tested compounds showed larval toxicity. Among the nine effective components, citronellol exhibited a pronounced larvicidal effect against the larvae of An. gambiae, with LC50 values of 96.1 and 55.6 ppm after 12 and 24 hours of treatment, respectively; however, hydroxycitronellal was the most potent compound after 48 and 72 h of exposure (LC50=3.7 and 2.3 ppm, respectively), followed by citronellol (LC50=16.7 and 6.3 ppm, respectively). Moreover, larval mortality was concentration- and time-dependent.
Analysis and Olfactory Description of Four Essential Oils from Vietnam
Authors: Schmidt Erich , Huong Le T. , Dai Do N. , Thang Tran D. , Wanner Juergen , Jirovetz Leopold
Published: March 2019

The present study evaluates the chemical composition and olfactory description of the essential oils of Asarum glabrum Merr., Calocedrus macrolepis Kurz, Cunninghamia lanceolata (Lamb.) Hook. and Glyptostrobus pensilis (Stainton ex D. Don) K. Koch. The essential oils were obtained by hydrodistillation in a Clevenger-type apparatus and analyzed by GC-FID and GC-MS. Concerning their chemical composition, 66, 42, 57 and 21 volatile compounds were identified from dried leaves in the case of Asarum glabrum Merr. and wood for the other three, representing 98.7%, 67.2%, 92.0% and 87.5 % of the total composition, respectively. The main compounds of Asarum glabrum oil were safrole (38.1%), apiole (10.8%) and myristicin (8.0%); of Calocedrus macrolepis verbenone (9.3%), piperitone (8.6 %), α-terpineol (6.0%) and ( Z)-β-terpineol (5.3%); of Cunninghamia lanceolata oil cedrol (26.3%), α-terpineol (24.1%) and camphor (7.0%); and of Glyptostrobus pensilis oil dihydro-eudesmol isomer (assumed) (18.3%), cedrol (16.4%), occidentalol (13.2%) and elemol (9.0%).
Effects of a Pleasant Natural Odor on Mood: No Influence of Age
Authors: Glass Sandra T. , Heuberger Eva
Published: March 2019

Certain fragrances significantly influence affective and cognitive states in humans as shown not only in the laboratory but also in natural outdoor settings. The aim of the present study was to investigate the influence of age on the relationship between a complex, natural odor and affective states, i.e., calmness, alertness and positive mood, in the field. The effect of a selected ambient odor on emotional well-being as well as on evaluations of odor intensity and pleasantness was assessed in healthy human subjects and compared with a control condition involving the same outdoor environment without the tested natural odor. The influence of age was studied in three different age groups, i.e., school children, young adults and elderly subjects. Despite overall emotional differences as a function of age, the tested ambient odor compared with the control condition improved subjective ratings of calmness, alertness and positive mood in all groups. Differences were found between age groups in regard to odor pleasantness, but not intensity. We concluded that the beneficial effect of the natural odor on affective states is not constrained by age. Furthermore, we replicated our previous finding that pleasant natural fragrances in outdoor environments improve mood state in humans.
A Pilot Study on the Physiological Effects of Three Essential Oils in Humans
Authors: Höferl Martina , Hütter Christina , Buchbauer Gerhard
Published: March 2019

In the present study, the physiological effects on 32 humans exposed to experimental stress provoked by inhalation of the essential oils of East Indian sandalwood ( Santalum album L.), Western Australian sandalwood ( Santalum spicatum R.Br.) and lavender ( Lavandula angustifolia MILL.) were investigated. During individual testing sessions, several saliva samples were collected, blood pressure was regularly measured and parameters of the autonomic nervous system (heart rate, skin conductance response) were continuously monitored. Salivary cortisol, as an endocrine stress indicator, was determined by time-resolved fluoroimmunoassay. Statistical analyses evidenced that the tested sandalwood essential oils significantly reduced systolic blood pressure, especially during the recreation phase. This finding corresponds with a distinct reduction of salivary cortisol levels during recreation in the Western Australian sandalwood oil compared with the control. In conclusion, the results demonstrate that essential oils can alleviate the physiological reactions to psychological stress and facilitate recovery after exposition to stress.
Natural Sesquiterpene Lactones as Potential Trypanocidal Therapeutic Agents: A Review
Authors: Muschietti Liliana V. , Ulloa Jerónimo L.
Published: March 2019

Chagas’ disease and Human African Trypanosomiasis are parasitic diseases that remain major health problems, mainly among the poorest and the most marginalized communities from Latin America and Africa. The scarcity of effective chemotherapy, due to the low investment in the research and development (R&D) of new drugs, together with a high incidence of side effects, and the emergence of drug resistance phenomena emphasize the urgent need for new prophylactic and therapeutic agents. Over the ages, humans have employed natural products to treat a wide spectrum of diseases. Recently, the pharmaceutical industry has focused on plant research and a large body of evidence has been collected to demonstrate the immense potential of medicinal plants as a source of bioactive compounds and lead molecules. In the field of parasitic diseases, drug development from plants has been successful for the sesquiterpene lactone (STL) artemisinin, which is employed as an antimalarial agent. STLs are a large group of naturally occurring terpenoids derived from plants that mostly belong to the Asteraceae family which exhibit a variety of skeletal arrangements and are the largest and most diverse category of natural products with an α-methylene-λ-lactone motif. STLs display a broad spectrum of biological activities such as antitumor, cytotoxic, antibacterial, anthelmintic, uterus contracting, antimalarial, neurotoxic, antiprotozoal and allergic (contact dermatitis) activities. In this context, the purpose of the present review is to provide an overview of the trypanocidal activity reported for STLs against Trypanosoma cruzi and T. brucei rhodesiense over the period 1993–2015.
Natural Triterpenoids for the Treatment of Diabetes Mellitus: A Review
Authors: Lyu Han , Chen Jian , Li Wei-lin
Published: March 2019

Triterpenoids, an important group of secondary metabolites, are widely distributed in nature. Many triterpenoids have been found with potential therapeutic effect against diabetes mellitus. However, the use of triterpenoids for the treatment of diabetes has not been systematically discussed previously. This review summarized the anti-diabetic activity of natural triterpenoids reported since the late 1980s with the emphasis on the molecular mechanisms.
The Biological Activity of Alkaloids from the Amaryllidaceae: From Cholinesterases Inhibition to Anticancer Activity
Authors: Habartová Klára , Cahlíková Lucie , Řezáčová Martina , Havelek Radim
Published: March 2019

Modern research has shown that Amaryllidaceae alkaloids represent a rich reservoir of potential small chemical molecules exhibiting several medicinal properties through various mechanisms. Among the many Amaryllidaceae compounds, galanthamine has been given a great amount of attention due to the fact that it possesses potent acetylcholinesterase inhibitory activity. In spite of the amount of evidence indicating the potential usefulness of Amaryllidaceae alkaloids in therapy, research groups have focused their attention on the other alkaloids present in this plant family. New investigations have shed light on many aspects of the structure of Amaryllidaceae alkaloids and on their semisynthetic modification, function, and mechanisms underlying in vitro and in vivo activity. In addition, Amaryllidaceae alkaloids have frequently been identified as having promising cytotoxic properties against cancer cell lines. While follow-up studies have repeatedly shown that Amaryllidaceae alkaloids and their derivatives demonstrate antiproliferative, cytotoxic and apoptosis-inducing activity, the mechanisms remain unclear. This review addresses the most important Amaryllidaceae alkaloids with anticancer potential, particularly those that have been studied for the purpose of gaining a better understanding of the basis of the activity at the cellular and molecular level.
An Interesting Tour of New Research Results on Umami and Umami Compounds
Authors: Greisinger Sabine , Jovanovski Stefan , Buchbauer Gerhard
Published: March 2019

Knowledge about the fifth basic taste, the umami taste, has been investigated by many scientists in the last years and continues to gain importance. Therefore, a lot of scientific studies were conducted to explore several effects influencing the mechanism of umami, which is elicited and enhanced by defined concentrations of MSG (monosodium glutamate) and umami compounds. This paper covers the most relevant scientific literature regarding umami, its use as a flavor enhancer, and the latest umami compounds, which have been released in the last ten years. The main goal of this overview was to summarize the most important results which were related to umami as one of the five basic tastes, the umami taste receptor, the essential role of umami in a great number of physiological mechanisms, and the MSG symptom complex. Furthermore, the function of umami in the interaction of taste, aftertaste and olfactory pathways has been discussed.
Synthesis of Ester-linked Docetaxel-glycoside Conjugate and Its Application to Drug Delivery System using Immunoliposome Targeted with Trastuzumab
Authors: Hamada Hiroki , Okada Shouta , Shimoda Kei , Hamada Hatsuyuki , Masuoka Noriyoshi
Published: March 2019

Chemo-enzymatic synthesis of the ester-linked monosaccharide conjugate of docetaxel, 7-glycolyldocetaxel 2″- O-β-D-galactopyranoside, was achieved by using lactase as a biocatalyst. The water-solubility and, EE and LE values for the liposome of 7-glycolyldocetaxel 2″- O-β-D-galactopyranoside were much higher than those of docetaxel. The immunoliposome containing 7-glycolyldocetaxel 2″- O-β-D-galactopyranoside showed effective suppression of tumor growth.
Aggregation Behavior of 6-Isocassine and N-Methyl-6-Isocassine: Insights into the Biological Mode of Action of Lipid Alkaloids
Authors: Reina Luis , Bottini Gualberto , Bennadji Zohra , Vinciguerra Vittorio , Ferreira Fernando , Menendez Pilar , Moyna Guillermo
Published: March 2019

The aggregation behavior of 6-isocassine and N-methyl-6-isocassine, two piperidin-3-ol alkaloids isolated respectively from the barks of Prosopis nigra and P. affinis, was investigated using a combination of NOE experiments and diffusion measurements in solvents of varying polarity and hydrogen bonding capacity. While the NOE enhancements for N-methyl-6-isocassine are positive, regardless of the solvent, those for 6-isocassine shift from negative to positive when going from chloroform- d to methanol- d 4 solution. In addition, despite the self-diffusion coefficients of both compounds being virtually identical in methanol- d 4, N-methyl-6-isocassine diffuses nearly twice as fast as the non-methylated alkaloid in chloroform- d. The changes in rotational and translational dynamics observed between solvents for 6-isocassine suggest that the molecule forms dimeric head-to-head aggregates in non-polar aprotic environments, a behavior that could help explain the biological mode of action that has been proposed for this type of alkaloids.
The LC/ESI-MSMS Profiles and Biological Potentials of Vitex agnus castus Extracts
Authors: Ağalar Hale Gamze , Çiftçi Gülşen Akalιn , Yιldιrιm Şafak Ulusoylar , Gögera Fatih , Kιrιmera Neşe
Published: March 2019

The chemical profile, cytotoxic and apoptotic effect, and antioxidant activity were determined of ethanolic extracts of Vitex agnus-castus L. (chaste tree). Ripened fruits and fruitless aerial parts were extracted with ethanol, and the chemical characterization of the extracts was determined by LC/ESI-MS-MS. Twelve compounds were tentatively identified in the extracts. The dose-dependent cytotoxic effects of the extracts were tested on C6, A549 and MCF-7 cells by using MTT assay; inhibition of DNA synthesis, and apoptotic and caspase-3 activation effects of the extracts were determined. The potential antioxidant activities of the extracts were evaluated by in vitro methods such as DPPH and ABTS scavenging activity, reducing power and β-carotene bleaching assays. The fruit extract showed noticeable cytotoxic activity against MCF-7 cells with an IC50 value of 88 μg/mL. Both extracts showed similar DPPH scavenging activity comparably with that of the standard.
Chemical Constituents of the Leaves of Tussilago farfara and their Aldose Reductase Inhibitory Activity
Authors: Kuroda Minpei , Ohshima Takumi , Kan Chihiro , Mimaki Yoshihiro
Published: March 2019

The inhibitory activity of 37 medicinal plant extracts against aldose reductase (AR) activity was evaluated. The most potent AR inhibitory activity was found in the MeOH extract of the leaves of Tussilago farfara (Compositae). Enzyme assay-guided fractionation of the extract led to the isolation of a new flavonoid glycoside, kaempferol 3- O-[3,4- O-(isopropylidene)-α-L-arabinopyranoside] (1), along with 15 known compounds (2–16), of which 3, 5, 13, 15, and 16 were isolated from T. farfara for the first time. The structures of 1–16 were elucidated based on MS and NMR data. Dicaffeoylquinic acid derivatives (7–12) showed potent AR inhibitory activity with IC50 values ranging from 0.58 to 5.38 μM, whereas flavonoid glycosides 1, 3, 5, and 6 showed weak inhibitory activity with IC50 values of 13.9, 15.1, 13.3, and 14.1 μM, respectively.
Quantitative Determination by HPLC-DAD of Icariin, Epimedin A, Epimedin B, and Epimedin C in Epimedium (Berberidaceae) Species Growing in Turkey
Authors: Polat Derya Cicek , Coskun Maksut
Published: March 2019

The genus Epimedium is rich in terms of flavonoids, of which icariin, epimedin A, epimedin B and epimedin C are known especially to be biologically active. Therefore, it is important to quantify these compounds. In this study, a HPLC method coupled with DAD detection was developed and validated for the determination of icariin, epimedin A, epimedin B and epimedin C in Epimedium species growing in Turkey. The chromatographic separation was performed using a gradient system with a mobile phase of 0.1% formic acid (A) and acetonitrile (B) applied at a flow rate of 1 mL/min using a diode array detector. The highest values were, respectively, icariin 0.65%, epimedin A 0.13%, epimedin B 0.11%, epimedin C 0.06%. The highest values were obtained from the materials collected in Uzungol (Trabzon-Turkey).
Toxicity of Compounds Isolated from White Snakeroot (Ageratina altissima) to Adult and Larval Yellow Fever Mosquitoes (Aedes aegypti)
Authors: Estep Alden S. , Becnel James J. , Lee Stephen T.
Published: March 2019

Botanicals have been the source for several classes of pesticides for mosquitoes. However, increasing resistance to these products and reduced numbers of choices necessitate the search for new active ingredients. Ageratina altissima (L.) King & H. Rob. or white snakeroot, is found throughout the eastern United States and contains known toxic compounds. We examine chromenes (benzopyrans) and benzofurans isolated from this plant for larvicidal and adulticidal activity against the dengue vector Aedes aegypti L. Initial activity identified several compounds that were effective against either larvae or adults. Interestingly, only two compounds were effective against both larva and adults. Dose curves were constructed from further testing of these active compounds to allow comparative ranking of efficacy. We identified dehydrotremetone as the most effective larvicide (0.03 ± 0.001 ng/μL) and 6-acetyl-7-methoxy-2,2-dimethylchromene as the most effective adulticide (1.17 ± 0.31 μg/org) although other compounds were also active. This study provides additional useful data for evaluation of chromenes and benzofurans as possible mosquiticidal agents.
Compounds from Terminalli brownii Extracts with Toxicity against the Fish Pathogenic Bacterium Flavobacterium columnare
Authors: Schrader Kevin K. , Cantrell Charles L. , Midiwo Jacob O. , Muhammad Ilias
Published: March 2019

The pond-raised channel catfish (Ictalurus punctatus) industry in the United States of America can incur losses of over a $100 million annually due to bacterial diseases including columnaris disease caused by Flavobacterium columnare. One management approach available to catfish producers is the use of medicated-feed containing antibiotics. However, the negative attributes of antibiotic use in agriculture include public concerns and the potential development of antibiotic-resistant bacteria. Therefore, the discovery of environmentally-safe natural compounds for use as therapeutic agents would greatly benefit the catfish industry. In this study, a rapid bioassay was used to evaluate crude plant extracts as the first step in the discovery of natural therapeutants. Plant extracts from Terminalia brownii were found to be inhibitory towards F. columnare. The minimum inhibitory concentration (MIC) of the 5% water-methanol extract of T. brownii (stem bark) was 10 μg/mL and the 24 h 50% inhibition concentration (IC50) was 40 μg/mL. Subsequent bioassay-guided fractionation of the T. brownii ethanol extract using reverse phase C-4 chromatography revealed the highest level of activity in the aqueous methanol (50:50) fraction. HPLC analysis and subsequent purification of this fraction provided two compounds identified as ellagic acid (1) and 4- O-(3″,4″-di- O-galloyl-α-L-rhamnopyranosyl)ellagic acid (2). Compound 2 was the most active isolated compound, with a minimum inhibitory concentration (MIC) of 10±0 μg/mL and 24 h IC50 of 31±1 μg/mL. Although 1 was more active according to a MIC of 6±5 μg/mL, its 24 h IC50 was >100 μg/mL, and, therefore, it was less active overall of the two most active isolated compounds.
Substrate Specificity of Aglaia loheri Active Isolate towards P-glycoprotein in Multidrug-Resistant Cancer Cells
Authors: Dapat Else , Jacinto Sonia , Efferth Thomas
Published: March 2019

Multidrug resistance (MDR) is a major contributory factor in the failure of chemotherapy. Concrete interpretation of P-glycoprotein (P-gp) substrate specificity, whether a substance is a substrate or an inhibitor, represents an important feature of a compound's pharmaceutical profiling in drug design and development. In this work, the P-gp substrate specificity of Maldi 531.2[M+H]+, a phenol ester from Aglaia loheri Blanco leaves was investigated. This study focuses on the effect of Maldi 531.2[M+H]+ on P-gp ATPase activity, which was examined by measuring the amount of inorganic phosphates (Pi) released as a result of ATP hydrolysis. To test the effects of Maldi 531.2[M+H]+ on MDR activity, an attempt to combine Maldi 531.2[M+H]+ with a potent P-gp substrate such as verapamil was performed. As a result of this combination treatment, two distinct patterns of interaction with P-gp activity were determined by a calcein-acetoxymethyl ester (AM) assay. Depending on the concentratgion, both stimulation and inhibition of MDR activity were observed at certain drug concentrations suggesting biphasic reactions, which can be understood as cooperative stimulation and competitive inhibition, respectively. Verapamil is a strong substrate to P-gp. Substrate specificity of Maldi 531.2[M+H]+ may be less than the substrate specificity of verapamil, but it acts additively together with low concentrations of verapamil in stimulating ATPase activity. On the one hand, verapamil and Maldi 531.2[M+H]+ exerted cooperative stimulation on P-gp. On the other hand, Maldi 531.2[M+H]+ acts as competitive inhibitor at higher concentrations.
Quantitative Determination of Betaine, Choline, Acetylcholine, and 20-Hydroxyecdysone Simultaneously from Atriplex Species by UHPLC-UV-MS
Authors: Wang Yan-Hong , Kumarihamy Mallika , Wang Mei , Smesler Andrew , Khan Ikhlas A. , León Francisco , Cutler Stephen J. , Muhammad Ilias
Published: March 2019

A simple, rapid, and sensitive UHPLC-UV-MS method was developed for the quantitative determination of betaine (1), choline (2), acetylcholine (3), and 20-hydroxyecdysone (4) from various species of Atriplex. The baseline separation of the four analytes was achieved on a reversed phase C18 column within nine minutes. The mobile phase was composed of 50 mM ammonium formate in 2% methanol-water containing 5 mM sodium dodecyl sulfate (pH = 8.2) and methanol with 0.01% ammonium hydroxide. The analytical method was validated for recovery, precision, limits of detection (LOD), and limits of quantification (LOQ). The developed method was applied for the characterization and quantitation of analytes from plant parts of different Atriplex species, including A. canescens, A. fruticulosa, A. fasciculata, A. semibaccata, and A. lentiformis. Compounds 1–4 were found in a range of 0.53–1.61%, detection under limit of quantification (DUL)-0.74, DUL-0.0038, and 0-0.10% ( w/w, mg in 100 mg plant material), respectively, in test samples. In leaf and fruit of A. canescens, a high content of 1, 2, and 4 were identified. The content of 1, 2, and 4 in A. canescens explains the potential implications of this native US plant for human health and nutrition. The result of this study provides a new method to analyze these phytoconstituents simultaneously in a mixture.
Lantana montevidensis Essential Oil: Chemical Composition and Mosquito Repellent Activity against Aedes aegypti
Authors: Blythe Eugene K. , Tabanca Nurhayat , Demirci Betul , Tsikolia Maia , Bloomquist Jeffrey R. , Bernier Ulrich R.
Published: March 2019

The essential oil (EO) of Lantana montevidensis (Spreng.) Briq. (L. sellowiana Link & Otto) was investigated for its chemical composition and mosquito repellent activity. The essential oil obtained by hydrodistillation of aerial plant parts was analyzed by GC-FID and GC-MS. The major constituents were β-elemene (22.0%), β-caryophyllene (20.1%), and germacrene D (9.4%). Sesquiterpene hydrocarbons were present in considerable quantities (78.9%) in the L. montevidensis EO, followed by oxygenated sesquiterpenes (8.9%), monoterpene hydrocarbons (7.7%), oxygenated monoterpenes (1.9%), diterpenes (1.2%) and other compounds (0.2%). The oil of L. montevidensis was repellent with a minimum effective dosage (MED) of 0.021 ± 0.013 mg/cm2 as compared with that of the positive control N,N-diethyl-3-methylbenzamide (DEET) with a MED of 0.006 ± 0.001 mg/cm2) against Aedes aegypti L. The major compound β-elemene was tested individually for its repellency and had a MED value of 0.23 ± 0.14 mg/cm2 (DEET was 0.008 ± 0.001 mg/cm2). This is the first report on the repellent activity of L. montevidensis EO and β-elemene using human-based in vivo assays against Ae. aegypti.
Phytotoxic and Antibacterial Activity of Essential Oil of New Peppermint Cultivar
Authors: Grul'ová Daniela , De Martino Laura , Mancini Emilia , Tkáčiková L'udmila , Šalamon Ivan , Fejer Jozef , De Feo Vincenzo
Published: March 2019

A new menthol cultivar of Mentha x piperita L. bred in East Slovakia was evaluated for the biological activity of its essential oils (EOs). The content and composition of the EO components changed during plant development and the different effects of samples collected each month (April - September) within the growing season were noted. EOs are considered to be an important source of potential allelochemicals. Changes in EO composition influenced phytotoxic activity. Stimulation and inhibition of seed germination and root elongation occurred with different EO concentrations. The four tested bacterial strains presented different resistance to the samples collected in different growing periods.
The use of the Comins-Meyers Amide in Synthetic Chemistry: An Overview
Authors: Monticelli Serena , Parisi Giovanna , Rui Marta , de la Vega-Hernández Karen , Murgia Irene , Senatore Raffaele , Holzer Wolfgang , Urban Ernst , Langer Thierry , Langer Thierry , Pace Vittorio
Published: March 2019

Formylation reactions are fundamental operations in synthetic chemistry allowing the incorporation into a given structure formyl groups amenable to further derivatization. Conceptually, the introduction of such groups through the reaction between an electrophilic donor and a nucleophilic acceptor ( i.e. organometallic reagent) constitutes a reliable technique with widespread applications. In this Highlight, we summarize the effectiveness of the so called Comins-Meyers amide - [2-( N-methyl- N-formylamino]pyridine – in such a chemistry with vistas to the synthesis of natural products and biologically active substrates.
Antinociceptive Properties of St. John's Wort (Hypericum perforatum) and Other Hypericum Species
Authors: Stojanović Nikola M. , Radulović Niko S. , Randjelović Pavle J. , Laketić Darko
Published: March 2019

This review aims at a coherent summary of the results obtained from various studies that concern analgesic-like activity of the extracts of H. preforatum L. and thirteen other Hypericum L. species (Hypericaceae). Botanical origin, plant organs and extraction modes of the plant material, experimental models, routes of administration and doses used for animal treatment are summarized. Mechanisms of action and substances (and even the synergy thereof) proposed so far to be responsible for the observed activity have also been discussed. Even though St. John's wort ( H. perforatum) is the most renowned plant species of this genus, it is neither the only nor the most potent one in inducing pain relief.