bluuebunny/crossref_metadata_2025 huggingface dataset:
Chemical Composition and Bioactivity of the Essential Oils of Heracleum pyrenaicum subsp. pollinianum and Heracleum orphanidis
Authors: Ušjak Ljuboš , Petrović Silvana , Drobac Milica , Soković Marina , Stanojković Tatjana , ćirić Ana , Niketić Marjan
Published: March 2019

The objective of this research was to analyze the chemical composition, antimicrobial and cytotoxic activity of Heracleum pyrenaicum subsp. pollinianum (Bertol.) F. Pedrotti & Pignatti (HPP) and H. orphanidis Boiss. (HO) essential oils. The composition of the oils was analyzed by GC and GC-MS. β-Pinene (35.1%) was the most abundant compound in HPP root oil, while ( Z)-falcarinol (80.0%) dominated in HO root oil. ( E)-Nerolidol (28.5%) was the main constituent in HPP leaf oil. HPP fruit oil, as well as HO leaf and fruit oils mainly contained aliphatic esters, mostly octyl acetate (50.5–84.5%). Antimicrobial screening was performed by microdilution method against eight bacterial and eight fungal strains. The strongest antibacterial activity was shown by both root oils (MICs 0.02–0.60 mg/mL and MBCs 0.04–2.50 mg/mL for HPP, and MICs 0.02–1.25 mg/mL and MBCs 0.04–2.50 mg/mL for HO), while the best antifungal potential was exhibited by HPP fruit oil (MICs 0.30–0.60 mg/mL and MFCs 0.60–1.25 mg/mL) and HO leaf oil (MICs 0.15–0.63 mg/mL and MFCs 0.30–1.25 mg/mL). The tested root and fruit oils exhibited strong cytotoxic effect, which was determined by MTT test against HeLa (IC50 7.53–21.07 μg/mL) and LS174 (IC50 24.16–58.86 μg/mL) cell lines.
Composition and Biological Activity of Volatile Oil from Salvia judaica and S. multicaulis from Jordan
Authors: Afifi Fatma U. , Kasabri Violet , Al-Jaber Hala I. , Abu-Irmaileh Barakat E. , Al-Qudah Mahmoud A. , Abaza Ismail F.
Published: March 2019

The aim of this work was to determine the composition of the hydro-distilled essential oil of Salvia judaica Boiss. and S. multicaulis Vahl. (Lamiaceae) from Jordan by GC and GC-MS and to report the actual composition of their fresh leaves and flowers using SPME (Solid Phase Micro-Extraction). Their dual alpha-amylase/alpha glucosidase and pancreatic lipase inhibitory activities as well as their anti-proliferative potential were screened. The aroma profile of the leaves, flowers, and flowers at pre-flowering stages of S. judaica, obtained through SPME was composed of sesquiterpene hydrocarbons (87.7 %, 71.8 %, and 86.2 %, respectively) while the hydro-distilled oil of the dry leaves was rich in oxygenated sesquiterpenes (50.8%). Fresh leaves of S. multicaulis were rich in oxygenated monoterpenes (58.1%), while monoterpene hydrocarbons dominated the blooming flowers (57.2%) and the flowers at the pre-flowering stage (64.7%). The hydro-distilled oil of the dry leaves was rich in oxygenated monoterpenes (77.6%). With doxorubicin as a positive control, no anti-proliferative activity was observed against colorectal cancer cell lines HT29, HCT116, and SW620 using SRB assay for either Salvia spp. In vitro enzymatic starch digestion was evaluated with Acarbose (IC50: 0.2± 0.0 μg /mL) as the reference drug. The respective IC50 (mg/mL) values of S. judaica and S. multicaulis aqueous extracts were 4.9 ± 0.4 and 10.3 ± 0.9. Modulation of pancreatic lipase activity (PL) was determined by colorimetry and compared with Orlistat (IC50: 0.11 ± 0.0 μg/mL). PL-IC50 values (μg/mL) obtained for S. judaica and S. multicaulis were 108.5±6.4 and 31.8 ± 0.8, respectively.
Spasmolytic and Ca++ Channel Blocking Potential of Nepetolide: Isolated from Nepeta Suavis
Authors: Khan Farman Ullah , Khan Arif-Ullah , Hussain Javid , Khan Ihsan Ullah , Muhammad Nawshad , Khan Aslam , Mehmood Sultan , Asiri Abdullah Mohamed , Khan Sher Bahadar , Gilani Anwarul Hassan
Published: March 2019

Nepeta suavis is used in traditional medicine for treatment of abdominal spasm (colic). The tricyclic clerodane type diterpene, nepetolide, isolated for the first time from Nepeta suavis. was evaluated for Ca++ antagonist and antispasmodic activities. When studied in isolated rabbit jejunum, nepetolide caused concentration-dependent (0.03–100 μM) relaxation of spontaneous and high K+ (80 mM)-induced contractions, like that caused by verapamil, indicating that nepetolide exhibits spasmolytic activity, possibly mediated through Ca++ channel blocking action, which provides scientific explanation for the medicinal application of Nepeta suavis as an antispasmodic agent.
Anti-proliferative Constituents from Selaginella moellendorffii
Authors: Zhou Xiao-Feng , Tong Guo-Tong , Wang Xiao-Wen , He Yi
Published: March 2019

Two new compounds, (3 R)-5,6,7-trihydroxy-3-isopropyl-3-methylisochroman-1-one (1) and rhamnocitrin-3- O-β-glucopyranosyl-4′- O-β-galactosyl-(1→3)-glucopyranoside (2), were isolated from the whole plants of Selaginella moellendorffii Hieron. Their structures were determined by spectroscopic methods. Additionally, compound 1 could inhibit the proliferation of HT29 cells through inducing cell apoptosis.
Detection and Quantification of Rotenoids from Clitoria fairchildiana and its Lipids Profile
Authors: Santos Rauldenis A. F. , David Jorge M. , David Juceni P.
Published: March 2019

This work describes the isolation and quantification of rotenoids from crude organic extracts of different parts of Clitoria fairchildiana R. A. Howard (Leguminosae) by HPLC-DAD. The lipid composition and the Artemia salina cytotoxic activities of the isolates were also conducted. Clitoriacetal (1), 6-deoxyclitoriacetal (2), stemonal and stemonone were isolated by chromatographic procedures and identified by usual spectroscopic and spectrometric techniques. Clitoriacetal and 6-deoxyclitoriacetal were not found in all parts of the plant, such as leaves and petals, but in the roots they occur in higher concentration. The activity against brine shrimp revealed that the root extract (LD50 = 158 ppm) was the more active.
Chemical Composition, Antioxidant and Cytotoxic Activities of Roots and Fruits of Berberis libanotica
Authors: Hosry Leina El , Boyer Laurent , Garayev Elnur E. , Mabrouki Fathi , Bun Sok-Siya , Debrauwer Laurent , Auezova Lizette , Cheble Edmond , Elias Riad
Published: March 2019

Fourteen compounds belonging to different chemical classes were characterized in the roots and fruits extracts from Berberis libanotica, using the same HPLC-DAD-MS method. Thirteen were reported, for the first time, from the fruits whereas the roots contained mostly alkaloids of which 3 out of 5 are reported for the first time. Their structures were established on the basis of MS data as gallic acid (1), chlorogenic acid (2), delphinidin (3), oxyacanthine (4), rutin (5), hyperoside (6), berbamine (7), isoquercitrin (8), quercitrin (9), jatrorrhizine (10), palmatine (11), berberine (12), quercetin (13) and luteolin (14). Extracts containing compounds 4 and 7 showed significant cytotoxicity against the HT29 cell line with an IC50 of 12.2–26.1 μg/mL. Fruits extracts, due mostly to compounds 1 and 2, showed potent antioxidant activities with an EC50 of 0.0025-0.019 mg/mL.
Four New Minor Compounds from Seeds of Plantago asiatica
Authors: Gao Zhonghua , Zhang Ling , Kong Lingmei , Yang Yan , Pu Debing , Gao Junbo , Shang Shanzhai , Li Yan , Xiao Weilie
Published: March 2019

Four new compounds, a dibenzylbutane lignin, plasiaticine F (1), an acetylenic glycoside, plasiaticine G (2), an indole alkaloid, plasiaticine H (3), and an ionone derivative, plasiaticine I (4), were isolated from the seeds of Plantago asiatica. The structures of the new compounds were elucidated on the basis of comprehensive analysis of spectroscopic data. Compounds 1–3 were tested for their cytotoxicity, but lacked significant activity.
Plant Tissue Cultures of Juniperus virginiana
Authors: Kašparová Marie , Spilková Jiřina , Cvak Ladislav , Siatka Tomáš , Martin Jan
Published: March 2019

Callus cultures of Juniperus virginiana L. (varieties ‘Hetzii’, ‘Glauca’, ‘Grey Owl’) were derived from fresh leaves of garden-grown trees on Schenk and Hildebrandt medium supplemented with 3.0 mg/L of α-naphthaleneacetic acid, 0.2 mg/L of kinetin and 15 mg/L of ascorbic acid. The growth characteristics of one-year-old and two-years-old cultures were determined. The maximum biomass in all varieties was achieved on the 35th day of the cultivation period. The increase in fresh weights of two-years-old callus cultures, when compared with one-year-old callus cultures, was as follows: variety ‘Hetzii’ by 25%, variety ‘Glauca’ by 29% and variety ‘Grey Owl’ by 49%. J. virginiana suspension cultures (varieties ‘Hetzii’, ‘Glauca’, ‘Grey Owl’) were derived from two-years-old callus cultures on Schenk and Hildebrandt medium supplemented with 3.0 mg/L of α-naphthaleneacetic acid, 0.2 mg/L of kinetin and 15 mg/L of ascorbic acid. The maximum biomass of all varieties was found on the 21st day of the cultivation period. These results indicate that a sub-cultivation interval of 35 days for callus cultures and of 21 days for suspension cultures can be recommended. The callus and suspension cultures of J. virginiana of the variety ‘Glauca’ have the best survivability and thus provide the most biomass.
Immunomodulatory Activity of Leaf Infusions of Selected Cornaceae Species on Human Leukocytes
Authors: Forman Vladimír , Bukovský Marián , Grančai Daniel
Published: March 2019

Particular Cornus species are known for their edible fruits and their leaves are used as a tea in some countries. In the present study, the immunomodulatory activity of water infusions of leaves of Cornus mas (CM), C. kousa (CK), C. alba (CA), C. flaviramea (CF), C. coreana (CC) and C. amomum (CU) was tested on human leukocytes. Phagocytic and antimicrobial activity was determined for concentrations of 0.17 and 0.25 mg.mL−1. All samples significantly enhanced the phagocytic activity of cells. Samples at the concentration of 0.17 mg.mL−1 were in all cases, except CK, slightly more effective than those at 0.25 mg.mL−1. The strongest bactericidal ( E. coli) and also candidacidal ( C. albicans) activity was exerted by CM at 0.25 mg.mL−1. The most potent samples at the lower concentration were CF (for E. coli) and CK (for C. albicans). CC and CU were antimicrobially non-effective.
P-glycoprotein Mediated Efflux Modulators of Plant Origin: A Short Review
Authors: Silva Nuno , Salgueiro Lígia , Fortuna Ana , Cavaleiro Carlos
Published: March 2019

Drug efflux transporters such as P-glycoprotein (P-gp) help maintain cellular homeostasis but are also major contributors to the development of multidrug resistance (MDR) phenomena. Since P-gp was associated with MDR, several compounds showing potential to inhibit this transporter have been identified. Particular attention has been given to natural products, namely those of plant origin, looking for highly effective and safe P-gp inhibitors with little to no interaction with other cellular or metabolic processes. Here we abridge several examples of plant compounds from distinct classes, polyketides, lignans, anthraquinones, coumarins, alkaloids, mono- and sesqui-terpenes, steroids and limonoids, which have shown the ability to modulate in vitro or in vivo the P-gp activity.
New Cytotoxic Guaianolides from Centaurea Aegyptiaca
Authors: Sary Hanan G. , Singab Abdel Nasser B. , Orabi Khaled Y.
Published: March 2019

The ethanol extract of Centaurea aegyptiaca aerial parts afforded two new chlorinated bioactive guaianolides, cenegyptin A (1) and cenegyptin B (2), in addition to four known sesquiterpenes (3-6). Their identities were established on the basis of their spectral data. The cytotoxicity (IC50, μM) of compounds 1-6 were evaluated against hepatic (HEPG2) and laryngeal (HEP2) carcinoma cell lines in comparison with normal fibroblasts (BHK). Compound 1 showed cytotoxic activity against HEPG2 and HEP2 with IC50 values of 7.2 ± 0.04 and 7.5 ± 0.02, respectively. However, compound 2 exhibited only a limited toxicity against both cell lines.
New Bioactive Semisynthetic Derivatives of 31-Norlanostenol and Obtusifoliol from Euphorbia Officinarum
Authors: Bailen Maria , Khamlichi Mourad Daoubi , Benharref Ahmed , Martinez-Diaz Rafael A. , Gonzalez-Coloma Azucena
Published: March 2019

Fifteen semisynthetic terpenoid derivatives from the major latex components of Euphorbia officinarum have been evaluated against the insect pest Spodoptera littoralis, two species of protozoan parasites, Trypanosoma cruzi and Leishmania infantum, and also against insect Sf9 and mammalian CHO cells to test their selective cytotoxicity. Our results showed that 40% of the test substances were postingestive toxicants to S. littoralis. All the tested derivatives had cytotoxic effects on insect-derived Sf9 cells, whereas mammalian CHO cells were affected by a lower number of compounds (47%). Furthermore, 87% of the test compounds had antiparasitic effects on bothi. infantum and T. cruzi, with some of them being selective parasite toxicants.
Cytotoxicity of Naturally Occurring Isoquinoline Alkaloids of Different Structural Types
Authors: Chlebek Jakub , Doskočil Ivo , Hulcová Daniela , Breiterová Kateřina , Šafratová Marcela , Havelek Radim , Habartová Klára , Hošt'alková Anna , Volštatová Tereza , Cahliková Lucie
Published: March 2019

Forty-six isoquinoline alkaloids, of eleven structural types isolated in our laboratory, have been evaluated for their cytotoxicity against two cancer cell lines (Caco-2 and Hep-G2 cancer cells), as well as against normal human lung fibroblast cells. Only scoulerine, aromoline, berbamine and parfumidine showed significant cytotoxic effects, but only scoulerine was active against both Caco-2 and Hep-G2 cells (IC50 values 6.44 + 0.87 and 4.57 + 0.42, respectively). Unfortunately, except for parfumidine, the other active alkaloids were also cytotoxic to the normal human lung fibroblast cells.
Guarea kunthiana Bark Extract Enhances the Antimicrobial Activities of Human and Bovine Neutrophils
Authors: Jerjomiceva Natalja , Seri Hisham , Yaseen Ragheda , de Buhr Nicole , Setzer William N. , Naim Hassan Y. , von Köckritz-Blickwede Maren
Published: March 2019

Guarea kunthiana is used in folk remedies for the treatment of several diseases including microbial infections. The mechanism behind this phenomenon still needs to be elucidated. Here, we investigated the effect of G. kunthiana bark extract on antimicrobial functions of human and bovine neutrophils as the first line of defense against infections. For this aim, neutrophils were isolated from either human or bovine blood and treated with G. kunthiana bark extract. The antimicrobial activity of the neutrophils against Staphylococcus (S.) aureus and Escherichia (E.) coli was tested in a bacterial survival assay and a fluorescence-based phagocytosis assay. Furthermore, the formation of neutrophil extracellular traps (NETs) was visualized by immunofluorescence microscopy. We show that neutrophils treated with G. kunthiana extract distinctly increased phagocytosis of S. aureus or E. coli. Interestingly, we demonstrate that G. kunthiana bark extract induces the formation of NETs in both cell types. This effect was abolished when treating the cells with diphenyleniodonium chloride (DPI) pointing to a direct implication of the NADPH oxidase-dependent formation of reactive oxygen species in this process. In summary, our data strongly suggest that G. kunthiana bark extract boosts the antimicrobial activities of neutrophils as the first line of defense against invading pathogens.
Red Wine Inhibits Aggregation and Increases ATP-diphosphohydrolase (CD39) Activity of Rat Platelets in Vitro
Authors: Caiazzo Elisabetta , Tedesco Idolo , Spagnuolo Carmela , Russo Gian Luigi , Ialenti Armando , Cicala Carla
Published: March 2019

Moderate consumption of red wine has been shown to exert a peculiar cardioprotective effect compared with other alcoholic beverages; inhibition of platelet aggregation seems to be one of the mechanisms underlying this beneficial effect. CD39/ATP-diphosphohydrolase is an integral membrane glycoprotein metabolizing ATP and ADP to AMP; in concert with CD73/ecto-5′-nucleotidase, it contributes to extracellular adenosine accumulation. CD39 is considered a key modulator of thrombus formation; it inhibits platelet aggregation by promoting ADP hydrolysis. There is evidence that red wine consumption increases CD39 activity in platelets from streptozotocin-induced diabetic rats. Here we show that two kinds of Aglianico red wines inhibit aggregation and increase ATP-and ADPase activity in rat platelets.
How the Addition of Spices and Herbs to Virgin Olive Oil to Produce Flavored Oils Affects Consumer Acceptance
Authors: Issaoui Manel , Flamini Guido , Souid Sondess , Bendini Alessandra , Barbieri Sara , Gharbi Ines , Toschi Tullia Gallina , Cioni Pier Luigi , Hammami Mohamed
Published: March 2019

With the aim to expand the olive oil market to a larger number of consumers who are not familiar with the sensory characteristics of virgin olive oil, the use of novel products known as “flavored olive oils”, obtained by adding different kind of spices and aromatic herbs, is spreading in many countries. In order to test consumer acceptability of this type of product, in a country (Tunisia) in which virgin olive oil is regularly consumed, flavored olive oils were prepared by adding aromatic extracts of thyme, oregano, a mix of herbs (used as pizza seasoning), rosemary, and basil to a monovarietal Chemlali virgin olive oil and a consumer test on 206 subjects was performed. Selected quality parameters (free acidity, peroxide number, oxidative stability, specific absorption at K232 nm and K270 nm) were also measured and no significant variations were detected. Slight differences were found concerning the content of minor compounds (chlorophylls, carotenoids and total phenols). On the other hand, notable differences were seen in the profiles of volatile compounds, which appeared to be responsible for the observed variability in consumer acceptance. Although the unflavored oil was more appreciated than the flavored ones, among the latter, thyme flavored olive oil was the most appreciated.
Erythrina Edulis (Pajuro) Seed Protein: A New Source of Antioxidant Peptides
Authors: Intiquilla Arturo , Jiménez-Aliaga Karim , Zavaleta Amparo I. , Arnao Inés , Peña Carmen , Chavez-Hidalgo Elizabeth L. , Hernández-Ledesma Blanca
Published: March 2019

Erythrina edulis Triana ex Micheli is a protein-enriched legume traditionally used for both dietary and medicinal purposes. In this paper, protein concentrate was obtained from the seed flour. SDS-PAGE analysis revealed a high number and intensity of bands in the range between 10 and 90 kDa. Neutrase®, Flavourzyme®, and Alcalase® were used to hydrolyze the protein concentrate at different times. By SDS-PAGE, the lower resistance of proteins to Alcalase® action was observed, providing hydrolyzates with higher radical scavenging activity. The 120 min-hydrolyzate showed ORAC and TEAC values of 2.51 and 0.91 μmol Trolox equivalents/mg of protein, respectively. A fraction lower than 3 kDa and rich in hydrophobic and aromatic amino acids was demonstrated to be mainly responsible for the observed activity. E. edulis could be a new alternative in the formulation of functional foods not only for its high protein content but also for the potential biological properties of its hydrolyzates.
A Validated HPLC Method for Simultaneous Determination of Caffeoyl Phenylethanoid Glucosides and Flavone 8-C-glycosides in Haberlea rhodopensis
Authors: Zheleva-Dimitrova Dimitrina , Nedialkov Paraskev , Giresser Ulrich
Published: March 2019

A HPLC-UV method for analysis of the main compounds: caffeoyl phenylethanoid glucosides myconoside (1) and paucifloside (2) and flavone 8-C-glycosides: hispidulin 8-C-β-galactopyranoside (3), hispidulin 8-C-(2″-O-syringoyl-β-glucopyranoside) (4), hispidulin 8-C-(6-O-acetyl-β-glucopyranoside) (5) and hispidulin 8-C-(6-0-acetyl-2″-0-syringoyl-β-glucopyranoside) (6) in Haberlea rhodopensis leaves was developed and validated. Compound 3 was isolated for the first time from the title species. Ultrasound extraction with 80% methanol at room temperature allowed a good recovery of analytes (from 87.2 % for 1 to 109.8 % for 3) and the precision of the entire procedure was between 1.6% and 6.9%. The subsequent HPLC separation and quantification was achieved using a Hypersil ODS C18 column and UV detection at 280 nm. The mobile phase comprised methanol and 0.1 % o-phosphoric acid, and gradient elution mode was applied. The detection limits ranged from 0.042 μg/mL (6) to 0.18 μg/mL (5). The total amount in leaves of the assayed phenolic compounds was 374.2 mg/g. Myconoside was found to be the dominant compound in H. rhodopensis extract (332.2 ±0.7 mg/g dw) and reached up to 88.8% of the analyzed mixture in leaves, while the total content of flavone C-glycosides was 17.1 mg/g dw.
New Aminonaphthoquinone from the Sea Urchins Strongylocentrotus pallidus and Mesocentrotus nudus
Authors: Vasileva Elena A. , Mishchenko Natalia P. , Zadorozhny Pavel A. , Fedoreyev Sergey A.
Published: March 2019

The aminonaphthoquinone, spinamine E (5), was isolated for the first time from the sea urchins Strongylocentrotus pallidus (Sars G.O., 1872) and Mesocentrotus nudus (A. Agassiz, 1864). The structure of 5 was elucidated as 2-amino-3,5,6,7,8-pentahydroxy-l,4-naphthoquinone using 1D 1H-, 13C- and 2D NMR procedures, and HR-ESI mass-spectrometric data of 5 and its trimethyl ether. Spinamine E, as well as two other aminonaphthoquinones of sea urchins, echinamines A (2) and B (3), along with their hydroxylated analogues, spinochrome E (4) and echinochrome A (1), were tested for their ability to scavenge the stable DPPH radical and to inhibit lipid peroxidation. All investigated naphthoquinones obtained from the sea urchins showed a high antiradical activity, which was up to 1.5 times higher than that of α-tocopherol. Echinamine B showed the highest scavenging effect (EC50 = 6.5-10−6 M); this effect decreases in the series 3>5>1>2>4>α-tocopherol. In a lipid peroxidation inhibition testing model, echinamine B and spinamine E showed the highest inhibitory effect. The stability of compounds 1-5 in weakly alkaline solutions was evaluated.
Insight into the Presence of Stilbenes in Medicinal Plants Traditionally Used in Croatian Folk Medicine
Authors: Mekinić Ivana Generalić , Skroza Danijela , Ljubenkov Ivica , Katalinić Višnja
Published: March 2019

Over the last years, great interest has arisen concerning plant stilbenes, especially resveratrol, which has a whole spectrum of positive biological activities. In this study, we investigated the presence of resveratrol monomers (trans- and cis- form) and naturally occurring derivatives of fraas-resveratrol (piceid, astringin and isorhapontin) in phenolic extracts of twenty medicinal plants traditionally used in Croatian folk medicine. The investigated compounds were present in the samples, in free form or as glucosides, and the highest share was found in immortelle, common yarrow and Lamiaceae plants. The obtained results indicate that biological activity of selected medicinal plants can be related to the presence of this valuable group of phytochemicals.
Chemical Composition, Herbicidal and Antifungal Activity of Satureja cuneifolia Essential Oils from Spain
Authors: Garcia-Rellán David , Verdeguer Mercedes , Salamone Adele , Blázquez Maria Amparo , Boira Herminio
Published: March 2019

The chemical composition of essential oils from Satureja cuneifolia growing in east Spain was analyzed by GC, GC/MS. Forty-five compounds accounting for 99.1% of the total oil were identified. Camphor (47.6%), followed by camphene (13.6%) were the main compounds. Their herbicidal and antifungal activity was tested in vitro against three weeds (Amaranthus hybridus, Portulaca oleracea and Conyza canadensis) and eleven common pathogenic or saprophytic fungi (Phytophthora citrophthora, P. palmivora, Pythium litorale, Verticillium dahlia, Rhizoctonia solani, Penicillium hirsutum, Colletotrichum gloeosporioides, Phaeoacremonium aleophilum, Phaemoniella chlamydospora, Cylindrocarpon liriodendri and C. macrodidymum). The essential oil was very active against A. hybridus and C. canadensis significantly inhibiting their germination and seedling growth. Minor activity was shown against P. oleracea, depending on the concentration applied. P. palmivora, P. citrophthora and Pa. chlamydospora were the most sensitive fungi to the treatment with the essential oil, whereas R. solani showed no inhibition. Results showed that S. cuneifolia essential oil could be used for biocontrol of weeds and fungal plant diseases.
A New Secoiridoid Glucoside, and a Metabolite Profile of Scabiosa lucida
Authors: Corradi Elisabetta , De Mieri Maria , Gafner Frank , Hamburger Matthias , Potterat Olivier
Published: March 2019

Fourteen secondary metabolites, including a new secoiridoid glucoside (1), were isolated from the aerial parts of Scabiosa lucida by a combination of column chromatography, preparative and semi-preparative HPLC. They were identified by extensive NMR, and ESI-MS experiments, and by comparison with literature data.
Rickicaryophyllane A, a Caryophyllane from the Ascomyceteous Fungus Hypoxylon rickii and a 10-Norbotryane Congener
Authors: Wiebach Vincent , Surup Frank , Kuhnert Eric , Stadler Marc
Published: March 2019

Herein we report the isolation from Hypoxylon rickii of a new sesquiterpenoid (1) with a caryophyllane skeleton. The planar structure of 1 was elucidated by NMR and HRMS data as the 1,12-dihydro-1 -hydroxyl derivative of caryophyllenol-I, for which we propose the name rickicaryophyllane A. Its relative stereochemistry was assigned with a series of 1D NOESY experiments, while the 1 R,2 S,5 R,9 R absolute configuration was demonstrated by Mosher‘s analysis. Besides, we isolated 3-(hydroxymethyl)-1,1,3,5-tetramethyl-1,2,3,5,6,7-hexahydro-4 H-inden-4-one (2) as a new 10-norbotryane derivative and the known metabolite orcacetophenone (3).
7α-Hydroxyfriedelan-3-one-26-ol-29-oic acid and other Constituents from Pileostegia viburnoides var. glabrescens
Authors: Chen Sheng-Huang , Yu Juan , Li Qin-Wen , Zhao Jian-Ping , Wedge David E. , Duke Stephen O. , Liao Duan-Fang , Wang Yu-Hong , Fronczek Frank R. , Khan Ikhlas A. , Wang Wei
Published: March 2019

Phytochemical investigation of the roots and rhizomes of Pileostegia viburnoides var. glabrescens led to the isolation and identification of 31 compounds (1-31), 25 of which (1-2, 4-7, 9-12, 15-18, 21-31) were isolated from the Pileostegia genus for the first time. 7α-Hydroxyfriedelan-3-one-26-ol-29-oic acid (1) is a new friedelane-type triterpene. The structure of n-butyl-β-D-fructopyranoside (2) was determined by single-crystal X-ray diffraction. Compounds 4 and 12 displayed marginal cytotoxicity against the P388 murine leukemia cell line with IC50 values of 13.4 μM and 25.0 μM, respectively. Compound 23 exhibited marginal anti-inflammatory activity by the inhibition of lipopolysaccharide induced nitric oxide production in RAW 264.7 macrophage cells, with an IC50 value of 32.0 μM. Compounds 3, 8-10, 25, and 27 were phytotoxic to the dicot Lactuca sativa (lettuce) and/or the monocot Agrostis stolonifera (bentgrass).
Crataegusins A and B, New Flavanocoumarins from the Dried Fruits of Crataegus pinnatifida var. major (Rosaceae)
Authors: Kazuma Kohei , Isobe Yuka , Asahina Haruka , Nehira Tatsuo , Satake Motoyoshi , Konno Katsuhiro
Published: March 2019

Crataegusins A (1) and B (2), new flavanocoumarins, were isolated from the crude drug Crataegus Fructus, i.e., the dried fruits of Crataegus pinnatifida var. major. Their structures were determined by spectroscopic methods. They were unique in terms of carrying a 3-(or 4-)substituted coumarin substructure while a flavanocoumarin generally does not carry any substituents in the 2-pyron ring. They showed a significant DPPH reducing activity compared with epicatechin. Their production would be biosynthetically regulated considering the results of an LC-MS analysis of the dried and fresh fruits, fruit skin, hypanthia, and leaves. Their structures led the authors to consider a hypothetical general biosynthetic pathway of the flavanocoumarins, to which a flavan-3-ol is converted through a Michael addition and successive oxidative decarboxylation or dehydration pathway.
A New Neolignan Glycoside from Vetiveria zizanioides Roots
Authors: Matsuo Yukiko , Ohba Chika , Maeda Saori , Fukaya Haruhiko , Mimaki Yoshihiro
Published: March 2019

A new neolignan glycoside (1) and four known aromatic compounds (2-5) were isolated from the roots of Vetiveria zizanioides. The structure of compound 1 was determined based on spectroscopic analysis and hydrolysis. The structure of known flavonoid glycoside 3 was confirmed by X-ray crystallography. Compound 5 showed weak cytotoxic activity against HL-60 cells with an IC50 value of 13.1 ± 0.04 μM.
A New Neolignan from Panicum turgidum
Authors: Zaki Ahmed A. , Ali Zulfiqar , El-Amier Yasser A. , Khan Ikhlas A.
Published: March 2019

A new neolignan, paniculignan (1), and a known lignan, tetracentronside B (2), were isolated from Panicum turgidum. The structure of 1 was elucidated by extensive spectroscopic methods including 1D and 2D NMR and HR-ESI-MS. The relative configuration of 1 was determined on the basis of circular dichroism spectroscopy, optical rotation, and NOESY correlations.
Antioxidant, Antimicrobial, and Cytotoxic Properties of Aniba parviflora Essential Oils from the Amazon
Authors: da Silva Joyce Kelly R. , Maia José Guilherme S. , Dosoky Noura S. , Setzer William N.
Published: March 2019

Essential oils (EOs) from leaves and branches of Aniba parviflora (Meisn.) Mez were obtained by hydrodistillation and their chemical compositions determined by gas chromatography-mass spectrometry. Oxygenated sesquiterpenoids were the most representative compound class in both EOs ( ≅ 40%). However, the leaf EO was rich in β-phellandrene (15.1%), linalool (14.1%), and γ-eudesmol (12.9%). The EO from the branches showed high concentrations of γ-eudesmol (16.8%), β-caryophyllene (15.7%), linalool (12.4%), β-phellandrene (6.7%), and bicyclogermacrene (6.0%). The EOs were screened for radical-scavenging activity using the DPPH assay. In the DPPH assay, the EOs showed an antioxidant activity with TEAC values of 296.8 ± 20.2 and 357.3 ± 43.8 mg.TE.mL−1, about one-third that of the Trolox standard. The EOs were subjected to antibacterial screening and displayed promising activity against Escherichia coli (MIC < 19.5 μg.mL−1). In addition, the EOs were tested for cytotoxic activity against MCF-7 breast tumor cells and the leaf EO (IC50 = 67.9 ± 3.0 μg.mL−1) was more active than that from the branches (IC50 = 102.2 ± 3.0 μg.mL−1).
Antioxidant, Anti-inflammatory and Anti-hyperglycaemic Activities of Essential Oils from Thymbra capitata, Thymus albicans, Thymus caespititius, Thymus carnosus, Thymus lotocephalus and Thymus mastichina from Portugal
Authors: Aazza Smail , El-Guendouz Soukaina , Miguel Maria Graça , Antunes M. Dulce , Faleiro M. Leonor , Correia A. Isabel , Figueiredo A. Cristina
Published: March 2019

The in vitro antioxidant, anti-inflammatory, anti-hyperglycaemic, and anti-acetylcholinesterase activities of the essential oils (EOs) isolated from six Lamiaceae species ( Thymbra capitata, Thymus albicans, Th. caespititius, Th. carnosus, Th. lotocephalus and Th. mastichina) grown in Portugal, were evaluated. Th. caespititius and T. capitata carvacrol/thymol-rich EOs showed the best capacity for preventing lipid peroxidation, and scavenging the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) and peroxyl free radicals, as well as for inhibiting lipoxygenase and α-amylase. However, Th. caespititius and Th. lotocephalus 1,8-cineole and linalool rich EOs were the best inhibitors of α-glucosidase. T. capitata, Th. lotocephalus and Th. albicans EOs were the most active for inhibiting acetylcholinesterase. Th. caespititius and Th. mastichina EOs were the main scavengers of nitric oxide (NO) radicals. The comparison between the present data with a survey of the existing literature on the in vitro biological activities of the essential oils isolated from the same species from Portuguese origin, using other methodologies, showed some differences. For instance the use of two oxidizable substrates (egg yolk and lecithin liposomes) led to distinct results mainly for those samples with relatively low activity. In addition, the EOs capacity for scavenging peroxyl radicals was also influenced by the presence of cyclodextrins, as a synergism seemed to occur between EOs and those carbohydrates.
Biosynthetic Pathways of Purine and Pyridine Alkaloids in Coffee Plants
Authors: Ashihara Hiroshi
Published: March 2019

Caffeine (1,3,7- N-trimethylxanthine) and trigonelline (1 N-methylnicotinic acid) are major alkaloids in coffee plants. The key enzymes involved in the biosynthesis of these compounds are very closely related N-methyltransferases belonging to the motif B’ family of methyltransferases. The major biosynthetic pathways of caffeine and trigonelline are summarized in this review, including new evidence obtained from recombinant enzymes. In addition, precursor supply pathways are discussed with newly obtained results. Transgenic plants produced by the modification of the expression of N-methyltransferase genes are also introduced.
Capgermacrene C, a New Sesquiterpenoid from a Bornean Soft Coral, Capnella sp.
Authors: Ishii Takahiro , Phan Chin-Soon , Kamada Takashi , Vairappan Charles Santhanaraju
Published: March 2019

A new bicyclogermacrene, capgermacrene C (1), along with a known compound, 1,4-peroxy-5-muurolene (2), were isolated from a population of Bornean soft coral Capnella sp. The structures of these metabolites were determined by extensive spectroscopic analysis, including NMR, and HRESIMS. Both compounds were subjected to antibacterial activity tests against antibiotic resistant clinical bacteria, but produced only negligible inhibition.
Daphnane Diterpenoids from Daphne altaica
Authors: Nugroho Alfarius Eko , Chin-Piow Wong , Hirasawa Yusuke , Janar Jenis , Kaneda Toshio , Shirota Osamu , Morita Hiroshi
Published: March 2019

Three new daphnane diterpenoids, altadaphnans A-C (1 – 3), have been isolated from the aerial parts of Daphne altaica, together with 7 known daphnane diterpenoids. Their structures were elucidated on the basis of 1D and 2D NMR data. Altadaphnans A-C (1 – 3) showed significant antiproliferative activity against human lung carcinoma cell line A549.
Glycosylation of Chrysin by Cultured Cells of Eucalyptus perriniana
Authors: Shimoda Kei , Kubota Naoji , Tanigawa Masato , Hamada Hiroki
Published: March 2019

The biotransformation of chrysin was investigated using cultured plant cells of Eucalyptus perriniana as biocatalysts. Chrysin was glucosylated to chrysin 7- O-β-D-glucoside and chrysin 7- O-β-gentiobioside.
A New Bioactive Secondary Metabolite from Artocarpus elasticus
Authors: Ramli Faiqah , Rahmani Mawardi , Ismail Intan Safinar , Sukari Mohd Aspollah , Rahman Mashitoh Abd , Zajmi Asdren , Akim Abdah Md , Hashim Najihah Mohd , Go Rusea
Published: March 2019

Detailed phytochemical investigation has been carried out on the bark of Artocarpus elasticus Reinw. ex Blume, which led to the isolation of artonin E (1), a new dihydrobenzoxanthone derivative named elastixanthone (2), cycloartobiloxanthone (3) and artobiloxanthone (4). Structures of these compounds were elucidated on the basis of various spectroscopic (UV, IR, 1D-NMR and 2D-NMR) and MS data. Compounds 1-3 displayed outstanding scavenging activity for 1,1-diphenylpicrylhydrazyl (DPPH) with IC50 values of 11.5, 21.6 and 40.0 μg/mL, respectively. In addition, compounds 1-3 displayed broad spectrum antimicrobial activities against thirteen different bacterial strains when tested using the disc diffusion assay. Cytotoxic screening revealed that artonin E (1) constantly exhibited strong cytotoxic activity against human estrogen receptor (ER+) positive breast cancer (MCF-7) and human estrogen receptor (ER-) negative (MDA-MB 231) cells in comparison with the other two, with IC50 values of 2.6 and 13.5 μg/mL, respectively, without being toxic towards the WRL68 (human normal liver) cell line (IC50 value more than 30 μg/mL). However, the compound was inactive against HepG2 (human liver carcinoma) cancer cells.
Pyranonigrin L, a New Antioxidant, Produced by the Hot Spring-derived Fungus Penicillium adametzii BF-0003
Authors: Uchida Ryuji , Miyazaki Hidetoshi , Yamaguchi Yuichi , Ishijima Hiroyuki , Tomoda Hiroshi
Published: March 2019

A new antioxidant, designated pyranonigrin L, was isolated from the culture materials of the hot spring-derived fungus Penicillium adametzii BF-0003 by solvent extraction, ODS column chromatography, and HPLC. Its planar structure was elucidated using various analytical techniques including UV, IR, and NMR spectroscopy and MS. Its absolute configuration was determined by a comparison of its circular dichroism (CD) spectrum with those of structurally related compounds. Pyranonigrin L was found to exhibit anti-oxidative activity with an EC50 value of 553 μM.
Structure of a Coumaric Acid Analogue with a Monoterpene Moiety from the Flowers of Osmanthus fragrans var. aurantiacus and Evaluation of Cinnamic Acid Analogues as Nitric Oxide Production and Degranulation Inhibitors
Authors: Nakamura Seikou , Liu Jiang , Nakashima Souichi , Ogawa Keiko , Ueda Takashi , Onishi Eri , Kurooka Kiwako , Moriwaki Yuko , Ryu Kaori , Xu Bin , Matsumoto Takahiro , Ohta Tomoe , Fukaya Masashi , Yoshikawa Masayuki , Matsuda Hisashi
Published: March 2019

A coumaric acid analogue with a monoterpene moiety named floraosmanol A (1) was isolated from the flowers of Osmanthus fragrans var. aurantiacus. The chemical structure was elucidated on the basis of chemical and physicochemical evidence. Floraosmanol A (1) significantly inhibited nitric oxide (NO) production in lipopolysaccharide- (LPS) activated RAW264.7 macrophages and the release of β-hexosaminidase as a marker of degranulation from rat basophile leukemia (RBL-2H3) cells. In addition, several cinnamic acid analogues were conjugated with geraniol and 3-methyl-2-buten-1-ol through an ester linkage. The inhibitory effects on NO production and the release of β-hexosaminidase of the synthesized compounds were examined for structure-activity relationships.
Identification of Cardioactive Leonurus and Leonotis Drugs by Quantitative HPLC Determination and HPTLC Detection of Phenolic Marker Constituents
Authors: Kuchta Kenny , Ortwein Jutta , Çaliş İhsan , Volk Rainer B. , Rauwald Hans W.
Published: March 2019

Officinal European Leonurus cardiaca, East Asian L. japonicus, and South African Leonotis leonurus are traditionally used for cardiovascular, gynecological, and neurological disorders. Nevertheless, a phytochemical assessment as a basis for their quality control and comparison amongst them has not yet been reported up to now. Here, a novel RP-HPLC method is presented for quantifying twelve phenolics, lavandulifolioside, verbascoside, hyperoside, ferulic acid, isoquercitrin, rutoside, apigenin-7- O-D-glucoside, and quercitrin, as well as chlorogenic, caffeic, rosmarinic, and cichoric acids, in 18 herbal and fruit samples of the three species, as well as in a L. cardiaca refined extract. Only ferulic acid was found in every sample, whereas rosmarinic acid and apigenin-7- O-D-glucoside were not detected in any sample. Chlorogenic, caffeic, and cichoric acids and rutoside were detected in all three species. Lavandulifolioside and verbascoside, the dominant phenolics of L. cardiac, were not present in any sample of L. japonicus. Lavandulifolioside was found in this first ever HPLC analysis on phenolics of L. leonurus. Hyperoside was not found in L. cardiaca, but in both L. japonicus and L. leonurus, whereas isoquercitrin was detected in L. cardiaca and L. leonurus, but not in L. japonicus. This approach facilitates identification and quality control via HPLC/HPTLC fingerprints.
Secondary Metabolites from Fungal Endophytes of Echinacea purpurea Suppress Cytokine Secretion by Macrophage-Type Cells
Authors: Kaur Amninder , Oberhofer Martina , Juzumaite Monika , Raja Huzefa A. , Gulledge Travis V. , Kao Diana , Faeth Stanley H. , Laster Scott M. , Oberlies Nicholas H. , Cech Nadja B.
Published: March 2019

Botanical extracts of Echinacea purpurea have been widely used for the treatment of upper respiratory infections. We sought to chemically examine fungal endophytes inhabiting E. purpurea, and to identify compounds produced by these endophytes with in vitro cytokine-suppressive activity. Twelve isolates from surface sterilized seeds of E. purpurea were subjected to fractionation and major components were isolated. Sixteen secondary metabolites belonging to different structural classes were identified from these isolates based on NMR and mass spectrometry data. The compounds were tested for their influence on cytokine secretion by murine macrophage-type cells. Alternariol (1), O-prenylporriolide (4), porritoxin (10) β-zearalenol (13), and ( S)-zearalenone (14) inhibited production of TNF-α from RAW 264.7 macrophages stimulated with LPS in the absence of any significant cytotoxicity. This is the first report of a cytokine-suppressive effect for 4. The results of this study are particularly interesting given that they show the presence of compounds with cytokine-suppressive activity in endophytes from a botanical used to treat inflammation. Future investigations into the role of fungal endophytes in the biological activity of E. purpurea dietary supplements may be warranted.
Characteristic Volatile Components of Trifoliate Orange Peel (Poncirus trifoliata)
Authors: Tomiyama Kenichi , Sakurai Kazutoshi , Yaguchi Yoshihiro , Kawakami Yukihiro , Asakawa Yoshinori
Published: March 2019

The volatile components of the peel of trifoliate orange { Poncirus trifoliata (L.) Raf.}, family Rutaceae, were investigated using SAFE technique after solvent extraction. Limonene was the most abundant component in the peel aroma extract, followed by myrcene, trans-β-ocimene, indole, β-caryophyllene, (3 E,6 E)-α-farnesene, germacrene D, and β-phellandrene. In this study, the single sulfur- and nitrogen-containing compound, 4-methyl-5-vinylthiazole, and two macrocyclic lactones, cyclododecanolide and (7 Z,10 Z,13 Z)-hexadecatrien-16-olide, were identified as citrus aroma components for the first time. As a result of AEDA for the polar fraction of the aroma extract, indole, ethyl octanoate and those macrocyclic lactones with musky notes were found to be responsible for the characteristic aroma profile of the peel of trifoliate orange. The enantiomeric distributions of the four odor-active components, linalool, β-citronellol, ethyl 2-methylbutanoate, and 2-methylbutanoic acid, were also determined by means of multidimensional chiral GC/MS.
Characteristic Aroma Features of Tencha and Sencha Green Tea Leaves Manufactured by Different Processes
Authors: Hasegawa Toshio , Shimada Yuta , Saito Hiroki , Fujihara Takashi , Haraguchi Kenji , Takahashi Atsushi , Nakajima Kenta
Published: March 2019

There are many varieties of tea ( Camellia sinensis) obtained by different processing methods. In Japan, sencha tea has been used to brew beverages for centuries, and tencha leaves are used to make powdered green tea, matcha, which is used as an important food additive to impart the odor of green tea. We investigated the differences between the odors of sencha and tencha and their aroma profiles. We used our new technique to evaluate the odor of green tea, based on the theory that the aroma characteristics of materials arise from the interactions of groups of compounds with similar structures. Hexane extracts from sencha and tencha leaves were analyzed by gas chromatography-olfactometry. We detected several important compounds for tencha. The hexane extracts were separated by distillation, and groups of compounds with different boiling points were obtained. We investigated the group of high-boiling point constituents, which had a matcha-like odor and consisted of a group of odor constituents common to sencha and tencha. Tencha had a characteristic seaweed-like odor, and the low-boiling point constituents caused the differences in the tencha and sencha odors.
Enhanced Production of δ-Guaiene, a Bicyclic Sesquiterpene Accumulated in Agarwood, by Coexpression of δ-Guaiene Synthase and Farnesyl Diphosphate Synthase Genes in Escherichia coli
Authors: Kato Takahiro , Lee Jung-Bum , Taura Futoshi , Kurosaki Fumiya
Published: March 2019

Two genes involved in δ-guaiene biosynthesis in Aquilaria microcarpa, δ-guaiene synthase (GS) and farnesyl diphosphate synthase (FPS), were overexpressed in Escherichia coli cells. Immunoblot analysis revealed that the concentration of GS-translated protein was rather low in the cells transformed by solely GS while appreciable accumulation of the recombinant protein was observed when GS was coexpressed with FPS GS-transformed cells liberated only a trace amount of δ-guaiene (0.004 μg/mL culture), however, the concentration of the compound elevated to 0.08 μg/mL culture in the cells transformed by GS plus FPS δ-Guaiene biosynthesis was markedly activated when E. coli cells coexpressing GS and FPS were incubated in enriched Terrific broth, and the content of the compound increased to approximately 0.6 μg/mL culture. These results suggest that coexpression of FPS and GS in E. coli is required for efficient 6-guaiene production in the bacterial cells, and the sesquiterpene-producing activity of the transformant is appreciably enhanced in the nutrients-enriched medium.
Antioxidants from Annatto Seeds as Possible Inhibitory Agents of the Hepatotoxicity Induced by the Antitumor Agent Cisplatin
Authors: Souza Lucéia Fátima , Medeiros Niara da Silva , Santos Paula Cilene Pereira dos , Pagno Carlos Henrique , Nora Cleice Dalla , de Jong Erna Vogt , de Oliveira Rios Alessandro
Published: March 2019

The effects of annatto seeds and of bixin on the oxidative damage induced by cisplatin in male Wistar rats was evaluated in the present study by way of lipid peroxidation, weight gain, the food efficiency coefficient, fat deposits in the hepatocytes and dosing of the enzymes in this organ. The animals were divided into four groups: control group (CG), cisplatin group (CPG), bixin+cisplatin group (CBG) and annatto+cisplatin group (CUG). Cisplatin (5 mg/kg body weight) was injected intraperitoneally 48 hours before the end of the experiment. The bixin and annatto were administered daily together with the commercial feed. The pre-treatment with annatto and bixin attenuated the cisplatin-induced liver damage and significantly reduced the enzymes AST and ALT. Annatto was shown to be capable of inhibiting lipid peroxidation as determined by TBARS. These results suggest that annatto seeds and bixin could be important agents in the reduction of cisplatin-induced hepatotoxicity.
In vitroAnticancer Activities of Some Triterpene Glycosides from Holothurians of Cucumariidae, Stichopodidae, Psolidae, Holothuriidae and Synaptidae families
Authors: Fedorov Sergey N. , Dyshlovoy Sergey A. , Kuzmich Alexandra S. , Shubina Larisa K. , Avilov Sergey A. , Silchenko Alexandra S. , Bode Ann M. , Dong Zigang , Stonik Valentin A.
Published: March 2019

Triterpene glycosides isolated from holothurians are natural products known to possess cytotoxic properties against cancer cells. However, their anticancer prophylactic activity has not been studied sufficiently. The anticancer prophylactic, cytotoxic, and pro-apoptotic properties of 18 triterpene glycosides, as well as their effects on the transcriptional activities of activator protein-1 (AP-1) and nuclear factor-κB (NF-κB), were examined using methods that included EGF-induced JB6 Cl41 P+ cell transforation in soft agar, flow cytometry, MTS assessment of cell viability, and a luciferase activity assay. The compounds inhibited EGF-induced neoplastic JB6 Cl41 P+ cell transforation in soft agar and caused apoptosis and necrosis of human HL-60 and THP-1 leukemia cells. AP-1 and NF-κB were involved in the cellular response to the treatment by the compounds. Conclusion: glycosides isolated from holothurians of Cucumariidae, Stichopodidae, Psolidae, Holothuriidae and Synaptidae families have potential for development as new antitumor agents and as instruments to study AP-1 and NF-κB.