bluuebunny/crossref_metadata_2025 huggingface dataset:
Chemical Composition and Biological Activities of Essential Oil from Hyptis Crenata Growing in the Brazilian Cerrado
Authors: Violante Ivana Maria Póvoa , Garcez Walmir Silva , da Silva Barbosa Carolina , Garcez Fernanda Rodrigues
Published: March 2019

Essential oils from species of the genus Hyptis are well-known for their significant biological properties, including antimicrobial and acaricidal activities. The essential oil from the aerial parts of H. crenata was obtained by hydrodistillation; borneol (17.8%), 1,8-cineol (15.6%) and p-cimene (7.9%) were characterized by GC-MS as its major constituents. The essential oil was evaluated in vitro for its antimicrobial activities against six fungal and five bacterial strains, by measuring the respective MICs, MFCs and MBCs, using broth microdilution methods. The strongest bactericidal activities were shown against Staphylococcus aureus and Enterococcus faecalis, while the strongest fungicidal activities were against Cryptococcus neoformans, Candida glabrata and Candida tropicalis. The oil was also assessed for its anti-tick properties and, at a concentration of 2.5%, it significantly inhibited in vivo oviposition of engorged females of the cattle tick Rhipicephalus (Boophilus) microplus, using the adult immersion test., with an effectiveness of 94.4%.
Chemical Composition and Anti-Proliferative Properties of Bursera graveolens Essential Oil
Authors: Monzote Lianet , Hill Gabrielle M. , Cuellar Armando , Scull Ramón , Setzer William N.
Published: March 2019

Bursera graveolens is a wild tree of commercial importance native to the Neotropics, which has been widely used in folk medicine. In the present study, the chemical composition and anti-proliferative properties of the essential oil from B. graveolens were assayed. The chemical composition of the essential oil, determined by GC-MS, was complex and dominated by limonene (26.5%). Bursera oil inhibited the growth of MCF-7 breast tumor cells as well as amastigotes of L. amazonensis, with IC50 values of 48.9 ± 4.3 and 36.7 ± 4.7 μg/mL, respectively. In addition, the cytotoxicity of the oil was 103.9 ± 7.2 μg/mL against peritoneal macrophages from BALB/c mice. These results demonstrate that the essential oil from B. graveolens is a promissory antiproliferative product.
Can Fruit-form be a Marker for Argan Oil Production?
Authors: Gharby Saïd , Harhar Hicham , Kartah Badr Eddine , Monfalouti Hanae El , Denhez Clément , Hilali Miloudi , Guillaume Dom , Charrouf Zoubida
Published: March 2019

Deforestation is an important matter for the argan forest whose preservation necessitates planting trees. Macroscopic parameters are urgently needed to identify trees presenting good potential as oil producers. This study demonstrates that argan oil produced from kernels of apiculate fruit is richer in d-tocopherol, whereas oil produced from spherical fruit is richer in linoleic acid, and that produced from fusiform fruit is richer in oleic acid. Therefore, the use of fruit-form as a marker could permit an easy organic production of “naturally enriched” oils.
Zephgrabetaine: A New Betaine-type Amaryllidaceae Alkaloid from Zephyranthes grandiflora
Authors: Katoch Deepali , Kumar Dharmesh , Sharma Upendra , Kumar Neeraj , Padwad Yogendra S. , Lal Brij , Singh Bikram
Published: March 2019

Zephgrabetaine (1), a new betaine type Amaryllidaceae alkaloid, along with seven known alkaloids, lycorine, galanthine, lycoramine, hamayne, haemanthamine, tortuosine, and ungeremine were isolated from the bulbs of Zephyranthes grandiflora and their structures elucidated by spectroscopic data analysis. The isolated alkaloids were tested for in vitro cytotoxic activities against two cell lines, C-6 (rat glioma cells) and CHO-K1 (Chinese hamster ovary cells). A dose dependent cytotoxic effect was exhibited by all the alkaloids on these two cancer cell lines with prominent activity of lycorine and haemanthamine.
Diosmin – Isolation Techniques, Determination in Plant Material and Pharmaceutical Formulations, and Clinical Use
Authors: Bogucka –Kocka Anna , Woźniak Michał , Feldo Marcin , Kocki Janusz , Szewczyk Katarzyna
Published: March 2019

Diosmin is a naturally occurring flavone glycoside used in the treatment of venous diseases. In this review, we present the clinical aspects of the use of diosmin preparations in venous stasis, hemorrheologic disorders and vein wall remodeling. Because of its multiple applications in biology and its many therapeutic activities, research on isolation and identification of diosmin is of high relevance. The aim of this review is to present an overview of techniques of isolation and separation of diosmin in plant material, pharmaceutical formulations such as Daflon®, Diosed® and Dioven® tablets, and biological fluids.
Cyclic Peroxides from a Two-Sponge Association of Plakortis communis-Agelas mauritiana
Authors: Jumaryatno Pinus , Lambert Lynette K. , Hooper John N. A. , Blanchfield Joanne T. , Garson Mary J.
Published: March 2019

A cyclic peroxide 1 with an unusual phenethenyl side chain, together with the known peroxide 2 with a C4-sidechain have been isolated from a two-sponge association of Plakortis communis – Agelas mauritiana (Carter, 1883) collected near Mooloolaba, South-East Queensland, Australia. Metabolite purification was complicated by the presence of the free carboxylic acid groups in 1 and 2; therefore, diazomethane treatment was undertaken to afford methyl ester 3. Following RP-HPLC purification, the ring-opened analogues 4 and 5 were also obtained. The structures of the new compounds were elucidated on the basis of their 1D and 2D NMR and MS data, and by comparison with literature data. The relative configuration of the isolated peroxides was determined by the interpretation of JH-H values and comparison of the 13C chemical shift data with literature data for related compounds. The bromopyrrole alkaloid longamide (6) was also isolated.
Cytotoxic Activity of Dihydrochalcones Isolated from Corema Album Leaves against HT-29 Colon Cancer Cells
Authors: León-González Antonio J. , López-Lázaro Miguel , Espartero José L. , Martín-Cordero Carmen
Published: March 2019

During our search for cytotoxic compounds from Andalusian vascular plants, the ethyl acetate extract from the leaves of Corema album (L.) D. Don (Ericaceae) was selected for its cytotoxic activity against the HT-29 human colon adenocarcinoma cell line. Two dihydrochalcones, 2′,4′-dihydroxydihydrochalcone (1) and 2′-methoxy-4′-hydroxydihydrochalcone (2), have been isolated from the leaves of C. album. Their structural identification was based on 1H NMR and 13C NMR data, including 2D NMR, and mass spectrometry. These compounds were subjected to the sulfhorhodamine B (SRB) cytotoxic assay against human colon adenocarcinoma cells (HT-29). Compounds 1 and 2 showed higher cytotoxicity than the positive control 5-fluorouracil (5-FU); the IC50 values (μM ± SEM) were 1.8 ± 0.4 for compound 1, 8.5 ± 2.1 μM for compound 2, and 8.7 ± 4.0 for 5-FU. The cytotoxic activity of 1 and 2 was reduced in the presence of the antioxidants N-acetylcysteine (NAC) and Mn(III) Tetrakis(1-methyl-4-pyridyl) porphyrin pentachloride (MnTMPyP), therefore suggesting that reactive oxygen species generation participates in the cytotoxic activity of these dihydrochalcones.
Chemical Composition, Antioxidant and Antimicrobial Activity of Essential Oil and Extracts of Tragopogon graminifolius, a Medicinal Herb from Iran
Authors: Farzaei Mohammad Hosein , Rahimi Roja , Attar Farideh , Siavoshi Farideh , Saniee Parastoo , Hajimahmoodi Mannan , Mirnezami Tahmineh , Khanavi Mahnaz
Published: March 2019

Tragopogon graminifolius DC., family Compositae, is widely consumed as a green vegetable in the west of Iran and for the treatment of gastrointestinal and hepatic ailments. In this study, the chemical composition of the essential oil from T. graminifolius aerial parts was evaluated by gas chromatography and gas chromatography mass spectrometry. Moreover, antioxidant and antimicrobial activity of the essential oil and various extracts of T. graminifolius were determined. Fifty-eight compounds representing 87.2% of the essential oil were identified. The main components were n-hexadecanoic acid (22.0%), β-caryophyllene (7.5%), heneicosane (6.6%), and nonanal (5.2%). The essential oil demonstrated the highest DPPH radical scavenging activity (56.6 ± 8.8ug/mL) and the 80% ethanolic extract the highest ferric reducing antioxidant activity (908.2±79.5 mmol Fe2+ ion/g extract). The total phenolic content of the 80% ethanolic extract from the aerial parts was the highest (560.7±18.8 mg/g gallic acid equivalent). In the antimicrobial test, Shigella dysenteriae was the most vulnerable microorganism, followed by Proteus vulgaris, and the essential oil exhibited the highest antibacterial activity among the samples. The results indicated that the essential oil and extracts of T. graminifolius could be consumed as a natural herbal preservative or complementary supplement in the food and pharmaceutical industries.
Clastogenic Effect of Atranorin, Evernic acid, and Usnic Acid on Human Lymphocytes
Authors: Stojanović Gordana S. , Stanković Miroslava , Stojanović Igor Ž. , Palić Ivan , Milovanović Vesna , Rančić Soflja
Published: March 2019

Three lichen secondary metabolites atranorin (1), evernic acid (2), and usnic acid (3), were evaluated for their in vitro clastogenic and antiproliferative effects on human lymphocytes using the cytochalasin-B blocked micronucleus (CBMN) assay at concentrations of 2 μg/mL, 4 μg/mL and 6 μg/mL of final culture solution. The frequency of micronucleus (MN) was scored in binucleated cells, and cytokinesis-block proliferation index (CBPI) was calculated. Among the tested compounds, 3 exhibited the most prominent effect decreasing the frequency of MN in the range of 42.5% - 48.9%, that is about double of the positive control amifostin WR-2721 that reduces MN frequency for 22.0%. The effect of evernic acid was approximately equal to action of amifostin (23.2% −32.9%). Atranorin at concentrations of 2 μg/mL and 4 μg/mL decreasing the frequency of MN only for 11.1% and 1.8%, while in concentration of 6 μg/mL increases the frequency of MN for 9.6 %. The comparable CBPI values of the investigated compounds and control suggested that they did not show a statistically significant inhibitory effect on lymphocyte cell proliferation at applied concentrations.
Essential Oil from Leaves of Liquidambar formosana Ameliorates Inflammatory Response in Lipopolysaccharide-activated Mouse Macrophages
Authors: Hua Kuo-Feng , Yang Tzu-Jung , Chiu Huan-Wen , Ho Chen-Lung
Published: March 2019

The essential oil from Liquidambar formosana leaves (EOLF) was demonstrated to exhibit anti-inflammatory activity in mouse macrophages. EOLF reduced nitrite oxide generation, secretion levels of tumor necrosis factor-α and interleukin-6, and expression levels of prointerleukin-1β, inducible nitric oxide synthase, and cyclooxygenase-2 in lipopolysaccharide (LPS)-activated mouse macrophages. EOLF also reduced NLRP3 inflammasome-derived interleukin-1β secretion. The underlying mechanisms for the EOLF-mediated anti-inflammatory activity were (1) reduction of LPS-induced reactive oxygen species generation; (2) reduction of LPS-induced activation of c-Jun N-terminal kinase, extracellular signal-regulated kinase, and p38 MAP kinase; (3) reduction of LPS-induced nuclear factor-κB activation. Furthermore, 25 compounds were identified in the EOLF using GC-FID and GC-MS and the major compounds were terpinen-4-ol (32.0%), β-pinene (18.0%), γ-terpinene (13.8%), and α-terpinene (9.7%). We found that LPS-induced nitrite oxide generation was inhibited significantly by terpinen-4-ol. Our results indicated that EOLF has anti-inflammatory activity and may provide a molecular rationale for future therapeutic interventions in immune modulation.
A Simple Method for Isolation and Purification of DIBOA-Glc from Tripsacum dactyloides
Authors: Willett Cammy D. , Lerch Robert N. , Goyne Keith W. , Leigh Nathan D. , Lin Chung-Ho , Roberts Craig A.
Published: March 2019

Naturally occurring benzoxazinones (Bx) are a highly reactive class of compounds that have received particular attention in the past several decades. Recently, we identified 2-β-D-glucopyranosyloxy-4-hydroxy-1,4-benzoxazin-3-one (DIBOA-Glc) as the compound present in the roots of Eastern gamagrass { Tripsacum dactyloides (L.)} responsible for atrazine degradation. However, characterization of the DIBOA-Glc/atrazine degradation reaction has been limited due to difficulties in attaining sufficient quantities of purified DIBOA-Glc. The objective of the study was to develop a simple purification and isolation method for obtaining bulk quantities of highly purified DIBOA-Glc. T. dactyloides roots were extracted with 90% aqueous methanol, and the crude extract was fractionated using an HPLC equipped with a C8 semi-prep column and fraction collector. UHPLC-DAD-MS/MS was used to confirm the identity of DIBOA-Glc in the fractions collected. Analysis by 13C and 1H NMR and DAD indicated that 542 mg of DIBOA-Glc with a purity of >99% was obtained. The reactivity of the DIBOA-Glc was confirmed in a 16 hour assay with atrazine, which resulted in 48.5% ± 1.2% (SD) atrazine degradation. The method described here offers several advantages over existing extraction and synthesis methods, which are more cumbersome, use hazardous chemicals, and yield only small quantities of purified compound. The newly developed method will facilitate future research characterizing the chemical behavior of DIBOA-Glc and determine its potential as an atrazine mitigation and remediation tool.
One-pot Synthesis of Hollongdione from Dipterocarpol
Authors: Smirnova Irina E. , Kazakova Oxana B. , Huong Do Thi Thu , Minnibaeva El'za M. , Lobov Alexandr N. , Suponitsky Kiryll Yu.
Published: March 2019

A one-pot synthesis of a hybrid triterpenoid-steroid molecule, hollongdione (22,23,24,25,26,27-hexanordammar-3,20-dion), was achieved in a yield of 89%, based on the selective dehydration of dipterocarpol following ozonolysis. The structure of hollongdione was confirmed by X-ray analysis for the first time. Dammar-20(22),24(25)-dien inhibited the growth of Mycobacterium tuberculosis (strain H37Rv) in vitro with a MIC of 50 μg/mL.
Stereocontrolled Total Synthesis of Tetrodotoxin from myo-Inositol and D-Glucose by Three Routes: Aspects for Constructing Complex Multi-Functionalized Cyclitols with Branched-Chain Structures
Authors: Sato Ken-Ichi , Akai Shoji , Yoshimura Juji
Published: March 2019

This report describes the stereocontrolled total synthesis of the multi-functionalized cyclitol derivative, tetrodotoxin, containing eight asymmetric carbons and different types of branched-chains, from myo-inositol and D-glucose using three different methods. The tetrodotoxin derivatives possess a relatively small molecular weight but unique structural and chemical properties. Selection of the appropriate synthetic method may be useful not only for compounds related to TTX (including related derivatives), but also for other highly complex multi-functionalized cyclitols containing branched-chains.
A Stepwise Protocol for Induction and Selection of Prominent Coniferous Cell Cultures for the Production of β-Thujaplicin
Authors: Ogita Shinjiro , Shichiken Masahito , Ito Chizuru , Yamashita Toshiyuki , Nomura Taiji , Kato Yasuo
Published: March 2019

In order to demonstrate the potential of plant cell culture systems to produce a target natural bioactive compound, we proposed a stepwise protocol for β-thujaplicin production as follows. 1. Induction phase: Characteristics of callus cultures originating from newly flushed shoots of 10 conifer species were evaluated on different basal media such as Murashige and Skoog (MS), Schenk and Hildebrandt (SH), and Lloyd and McCown's Woody Plant medium (WP) containing 10 μM 2,4-dichlorophenoxyacetic acid (2,4-D) either alone or in combination with 1 μM of N6-benzyladenine (BA). The conifer species used were as follows: Chamaecyparis ( C. obtusa Sieb. et Zucc. and C. pisifera Sieb. et Zucc), Juniperus (J. chinensis L. ‘Kaizuka', J. chinensis L. var. sargentii, and J. conferta Parlatore), Thuja (T. occidentals L. and T. standishii (Gord.) Carr.), Thujopsis (T. dolabrata Sieb. et Zucc. and T. dolabrata Sieb. et Zucc. var. hondae), and Cryptomeria (C. japonica D. Don). We observed the phenotypes of each callus to determine the optimal conditions for callus induction and to infer biosynthetic activity of the calli over 4–8 weeks. 2. Habituation phase: Each of the cell cultures obtained was transferred to a modified MS medium containing 680 mg L−1 KH2PO4 and 10 μM Picloram to select the habituated cells with synchronous growth pattern. The growth of each cell culture was highly improved in the habituation medium, except that of J. chinensis ‘Kaizuka'. 3. Metabolite-production phase: The concentration of β-thujaplicin (known as hinokitiol in Japan) in the shoots of donor trees and the habituated cell cultures was analyzed via high-performance liquid chromatography (HPLC). Histochemical characteristics of the cells were also observed using laser scanning microscopy (LSM) imaging. After the third step, we tested the biosynthetic activity of two habituated calli ( C. obtusa and J. conferta) on a 0.3%, w/v, yeast extract (YE)-containing medium. We found significant improvement in β-thujaplicin production in J. conferta callus (4600 μg g DW-1), which was up to 20-fold higher than in the habituation phase.
Revisiting Caffeine Biosynthesis – Speculations about the Proximate Source of its Purine Ring
Authors: Baumann Thomas W.
Published: March 2019

The prevailing hypothesis of caffeine biosynthesis starting from xanthosine was combined with Kremers’ speculation on NAD as a biochemical precursor of caffeine and trigonelline in coffee. This bold sketch together with a few free-spirited ideas may channel future caffeine biosynthesis studies into novel directions.
Intracerebral Distribution of α-Pinene and the Anxiolytic-like Effect in Mice following Inhaled Administration of Essential Oil from Chamaecyparis Obtusa
Authors: Kasuya Hikaru , Iida Sayuka , Ono Kurumi , Satou Tadaaki , Koike Kazuo
Published: March 2019

The anxiolytic-like and stress reduction effects following inhaled administration of essential oil from Chamaecyparis obtusa (EOCO) have been reported. Volatile components are thought to produce these effects of EOCO by neurological transfer and pharmacological transfer. The regions of the brain in which inhaled compounds are found due to pharmacological transfer of EOCO are not known. This research was undertaken to clarify the relationship between the intracerebral distribution of α-pinene, which is the main component of EOCO, and emotional behavior. α-Pinene was detected as the main component of volatile EOCO. The amount of α-pinene in each region of the brain was measured following inhaled administration of EOCO. The amount of α-pinene was different in each region of the brain. With inhaled administration of 32 μL/L air EOCO, a high concentration of α-pinene was observed. However, no significant differences in the concentration of α-pinene among brain regions were found. A therapeutic concentration of α-pinene (8 μL/L air EOCO) in each region of the brain may induce an anxiolytic-like effect, and a high concentration of α-pinene (32 μL/L air EOCO) in each region of the brain may induce an excitatory-like effect. The increases in the concentration of α-pinene from 8 to 32 μL/L air EOCO in the striatum and the hippocampus were significantly lower compared with the increases in other brain regions. These results indicate that regions besides the striatum and the hippocampus participated in the increase in locomotor activity due to the high concentration of α-pinene in the brain.
Poplar-type Propolis: Chemical Composition, Botanical Origin and Biological Activity
Authors: Ristivojević Petar , Trifković Jelena , Andrić Filip , Milojković-Opsenica Dušanka
Published: March 2019

Propolis is one of the most used natural products known for centuries for its beneficial effects. Due to significant differences in chemical composition of samples originating from different geographic and climatic zones it is crucial to characterize reliably each type of propolis. This article comprises the latest findings concerning the poplar type propolis, i.e. it gives a cross section of chemical composition, botanical origin and biological activity of poplar type propolis in order to encourage further investigations that would indicate its beneficial effects.
Two New Eremophilane Sesquiterpenes and One New Resorcinol from Ligularia Knorringiana
Authors: Dai Wei , Li Hui , Cong Wenli , Zhao Wenbin , Wang Qi
Published: March 2019

Two new eremophilane sesquiterpenes, 12-oxa-1β, 5β,8,9aβ-tetramethyl-4α,5-ethano-4aβ-hydroxy-7β,10aβ-epoxy-9β-angeloyloxy-1,2,3,4,4a,5,6,7,9,9a,10,10a-dodecahydro-anthracen-13-on (knorringianalarin A, 1) and 6,9-dien-8-oxoeremophil-12-nor-11-ketone (knorringianalarin B, 2), and a new resorcinol, 4-acetyl-6-(2-methylpropionyl)-1,3-resorcinol (knorringianalarin C, 3) were isolated from the roots and rhizomes of Ligularia knorringiana, together with three known eremophilane sesquiterpenes (4–6). The structures of the new compounds were identified by spectroscopic methods including 2D-NMR techniques.
Profiling of Gallic and Ellagic Acid Derivatives in Different Plant Parts of Terminalia Arjuna by HPLC-ESI-QTOF-MS/MS
Authors: Singh Awantika , Bajpai Vikas , Kumar Sunil , Sharma Kulwant Rai , Kumar Brijesh
Published: March 2019

Terminalia arjuna is a medicinal plant used in ethnomedicine and the codified traditional medicine. A number of active constituents are reported, but there is no information on the whole range of gallic and ellagic acid derivatives present in this plant. A rapid and sensitive analytical method was developed using reverse phase high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (HPLC-ESI-QTOF-MS/MS) for qualitative analysis to determine the array of bioactive phytochemicals and their variations in different plant parts viz. bark, unripe fruit, ripe fruit, leaf, root and stem. Separation was performed on a Thermo Betasil C8 column (250 mm×4.5 mm, 5μm) with a mobile phase consisted of 0.1% formic acid aqueous solution and acetonitrile at a flow rate of 0.5 mL/min in 55 min. A wide range of constituents of T. arjuna were characterized and broadly grouped as 27 gallic acid and 52 ellagic acid derivatives.
Medicinal Plants Used in Mali for the Treatment of Malaria and Liver Diseases
Authors: Haidara Mahamane , Bourdy Geneviève , De Tommasi Nunziatina , Braca Alessandra , Traore Korotoumou , Giani Sergio , Sanogo Rokia
Published: March 2019

Today, ethno-pharmacology is a very important resource in order to discover new therapies for the current diseases. Moreover, another good justification for the ethno-pharmacological approach is to obtain new, effective, less expensive and simple therapies, limiting at the same time the cost of pharmaceutical research. Two major anti-malarial drugs widely used today, i.e. quinine and artemisinin, came respectively from Peruvian and Chinese ancestral treatments reported in the traditional medicines. In this contest, there is an urgent need for the discovery of new drugs, due to the critical epidemiological situation of this disease and to the growth of resistances. In Mali, malaria and liver diseases remain one of the leading public health problems. Many medicinal plants are often used, in local traditional medicine, for the treatment at the same time of malaria and liver diseases, including hepatic syndromes, jaundice, hepatitis and other hepatic disorders. Moreover, in the local language Bamanan, the word “ Sumaya” is used both for malaria and some liver diseases. In addition, we noted that some of the improved traditional phytomedicines produced by the Department of Traditional Medicine are prescribed by modern doctors both for malaria and liver diseases. In this review, pharmacological, toxicological and phytochemical data on Argemone mexicana L. (Papaveraceae), Cochlospermum tinctorium Perr. ex A. Rich (Cochlospermaceae), Combretum micranthum G.Don (Combretaceae), Entada africana Guillet Perr. (Mimosaceae), Erythrina senegalensis A. DC (Fabaceae), Mitragyna inermis (Willd) Kuntze (Rubiaceae), Nauclea latifolia Smith syn. Sarcocephalus latifolius (Smith) Bruce (Rubiaceae), Securidaca longepedunculata Fresen (Polygalaceae), Trichilia emetica Vahl. (Meliaceae), and Vernonia colorata (Willd) Drake (Asteraceae) are reported. Some of the collected data could be used to improve the actual herbal drugs and to propose new phytomedicines for the management of malaria and liver diseases.
Hydrolyzable Tannins from Sweet Chestnut Fractions Obtained by a Sustainable and Eco-friendly Industrial Process
Authors: Campo Margherita , Pinelli Patrizia , Romani Annalisa
Published: March 2019

Sweet Chestnut ( Castanea sativa Mill.) wood extracts, rich in Hydrolyzable Tannins (HTs), are traditionally used in the tanning and textile industries, but recent studies suggest additional uses. The aim of this work is the HPLC-DAD-ESI-MS characterization of Sweet Chestnut aqueous extracts and fractions obtained through a membrane separation technology system without using other solvents, and the evaluation of their antioxidant and antiradical activities. Total tannins range between 2.7 and 138.4 mM; gallic acid ranges between 6% and 100%; castalagin and vescalagin range between 0% and 40%. Gallic Acid Equivalents, measured with the Folin-Ciocalteu test, range between 0.067 and 56.99g/100g extract weight; ORAC test results for the marketed fractions are 450.4 and 3050 μmol/g Trolox Equivalents/extract weight. EC50 values, measured with the DPPH test, range between 0.444 and 2.399 μM. These results suggest a new ecofriendly and economically sustainable method for obtaining chestnut fractions with differentiated, stable and reproducible chemical compositions. Such fractions can be marketed for innovative uses in several sectors.
Chemical Composition and Antimicrobial Activity of the Essential Oil from Flowers of Eryngium triquetrum (Apiaceae) Collected Wild in Sicily
Authors: Casiglia Simona , Bruno Maurizio , Rosselli Sergio , Senatore Felice
Published: March 2019

The chemical composition of the essential oil from flowers of Eringium triquetrum Vahl. collected in Sicily was evaluated by GC and GC-MS. The main components were pulegone (50.6%), piperitenone (30.5%) and menthone (7.0%). Comparison of this oil with other studied oils of Eringium species is discussed. The oil showed good antibacterial and antifungal activities against some microorganisms that infest historical art works.
New Chromone, Isocoumarin, and Indole Alkaloid Derivatives from three Sponge-derived Fungal Strains
Authors: Meng Ling-Hong , Chen Hui-Qin , Form Imke , Konuklugil Belma , Proksch Peter , Wang Bin-Gui
Published: March 2019

Two new chromone derivatives, 2-hydroxymethyl-3-methyl-7-methoxychromone (1) and 2-hydroxymethyl-3- tert-butyl-7-methoxychromone (2), together with a related known compound, 2,3-dimethyl-7-methoxychromone (3), were isolated from Rhinocladiella sp. (IO2), a fungus obtained from the sponge Ircinia oros. Furthermore, a new isocoumarin derivative, 3-(3-chloro-2-hydroxypropyl)-8-hydroxy-6-methoxy-isochromen-1-one (4) and a known analogue 3-[( R)-3,3-dichloro-2-hydroxypropyl]-8-hydroxy-6-methoxy-1 H-isochromen-1-one (dichlorodiaportin, 5), were identified from sponge-derived fungal strain Clonostachys sp. (AP4.1), while a new indole alkaloid 1-(4-hydroxybenzoyl)indole-3-carbaldehyde (6) was obtained from the sponge-derived fungus Engyodontium album (IVB1b). The structures of these compounds were established by NMR spectroscopic and mass spectrometric data analysis, as well as by comparison with literature reports. Compounds 4 and 6 were examined for cytotoxic and antimicrobial activities, respectively. None of them showed potent activity.
Structural Features for Furan-Derived Fruity and Meaty Aroma Impressions
Authors: Wailzer Bettina , Klocker Johanna , Wolschann Peter , Buchbauer Gerhard
Published: March 2019

Furan derivatives are part of nearly all food aromas. They are mainly formed by thermal degradation of carbohydrates and ascorbic acid and from sugar-amino acid interactions during food processing. Caramel-like, sweet, fruity, nutty, meaty, and burnt odor impressions are associated with this class of compounds. In the presented work, structure-activity relationship (SAR) investigations are performed on a series of furan derivatives in order to find structural subunits, which are responsible for the particular characteristic flavors. Therefore, artificial neural networks are applied on a set of 35 furans with the aroma categories “meaty” or “fruity” to calculate a classification rule and class boundaries for these two aroma impressions. By training a multilayer perceptron network architecture with a backpropagation algorithm, a correct classification rate of 100% is obtained. The neural network is able to distinguish between the two studied groups by using the following significant descriptors as inputs: number of sulfur atoms, Looping Centric Information Index, Folding Degree Index and Petitjean Shape Indices. Finally, the results clearly demonstrate that artificial neural networks are successful tools to investigate non-linear qualitative structure-odor relationships of aroma compounds.
Pharmacophore Models Derived from Molecular Dynamics Simulations of Protein-Ligand Complexes: A Case Study
Authors: Wieder Marcus , Perricone Ugo , Seidel Thomas , Langer Thierry
Published: March 2019

A single, merged pharmacophore hypothesis is derived combining 2000 pharmacophore models obtained during a 20 ns molecular dynamics simulation of a protein-ligand complex with one pharmacophore model derived from the initial PDB structure. This merged pharmacophore model contains all features that are present during the simulation and statistical information about the dynamics of the pharmacophore features. Based on the dynamics of the pharmacophore features we derive two distinctive feature patterns resulting in two different pharmacophore models for the analyzed system – the first model consists of features that are obtained from the PDB structure and the second uses two features that can only be derived from the molecular dynamics simulation. Both models can distinguish between active and decoy molecules in virtual screening. Our approach represents an objective way to add/remove features in pharmacophore models and can be of interest for the investigation of any naturally occurring system that relies on ligand-receptor interactions for its biological activity.
Chemical Characterization of the Volatiles of Leaves and Flowers from Cultivated Malva sylvestris var. mauritiana and their Antimicrobial Activity Against the Aetiological Agents of the European and American Foulbrood of Honeybees (Apis mellifera)
Authors: Cecotti Roberto , Bergomi Patrizia , Carpana Emanuele , Tava Aldo
Published: March 2019

The composition of the volatile fraction of Malva sylvestris var. mauritiana (L.) Boiss. (Malvaceae) was investigated. This plant species was cultivated in the southeastern Alps as an ingredient for herbal teas and infusions. Flowers and leaves were collected at the end of the summer season and separately steam-distilled to obtain two volatile oils, the yields of which were 0.019% for leaves and 0.012% for flowers. After GC-FID and GC-MS analyses, the two oils revealed differences in the nature and especially in the proportion of their components, which were aldehydes, alcohols, phenolics, esters, hydrocarbons and acids. Eugenol was the single most abundant compound in the leaves, totalling 46.7% of the total oil, followed by phytol with 34.4%. Flowers showed a predominance of hydrocarbons, among which the anteiso branched-chain saturated hydrocarbon, 3-methyl tricosane, was the most abundant compound, accounting for 14.9% of the total volatiles. Eugenol ranked second with 10.3%, followed by the two linear-chain saturated hydrocarbons pentacosane and tricosane forming 8.2 and 7.7% of the total oil, respectively. The occurrence and the relative abundance of compounds from various chemical classes such as phenolics, hydrocarbons and aromatic aldehydes and alcohols are discussed, together with some of their ecological implications. The obtained volatile oils were than tested against two major honeybee ( Apis mellifera) pathogens, namely Paenibacillus larvae and Melissococcus plutonius, the causative agents of the American and the European foulbrood, respectively.
Comparative Evaluation of Phytochemicals, and Antidiabetic and Antioxidant Activities of Cuscuta reflexa Grown on Different Hosts in Northern Thailand
Authors: Tanruean Keerati , Kaewnarin Khwanta , Suwannarach Nakarin , Lumyong Saisamorn
Published: March 2019

For the first time, total phytochemical profiles of methanol crude extracts of Cuscuta reflexa grown on three different hosts, Coccinia grandis, Ficus racemosa and Samanea saman, that were cultivated in northern Thailand were examined, along with their antidiabetic and antioxidant activities. The highest level of total flavonoids (114.4 mg QE/ g extract) and total phenolic content (90.8 mg GAE/ g extract) were observed in the extract of Cu. reflexa that was grown on Co. grandis. The GC-MS results showed that various types of phenolic compounds, hydrocarbons, saturated fatty acids and methyl ester of fatty acids, unsaturated fatty acids and methyl ester of fatty acids, vitamin E, terpenes and sterol contained in the extracts of Cu. reflexa were capable of being grown on three hosts. Moreover, the HPLC results showed the presence of gallic acid, catechin, vanillic acid, rutin and quercetin in all Cu. reflexa samples. The extract of Cu. reflexa that was grown on Co. grandis represented the highest antidiabetic activity with a percent inhibition of 51.2. Moreover, the extract also possessed the greatest antioxidant activity (DPPH; IC50 168.6 μg/mL, FRAP; 40.5 mg GAE/ g extract).
A New Cytotoxic Cyclolanostane Triterpenoid Xyloside from Souliea vaginata
Authors: Wu Haifeng , Yang Zhixin , Wang Qiru , Zhu Nailiang , Xu Xudong , Zou Qiongyu , Tang Yulian
Published: March 2019

A new cyclolanostane triterpenoid xyloside, soulieoside P (1), and a known oleanane-type saponin, hederasaponin B (2), were isolated from the rhizomes of Souliea vaginata. Their structures were established by extensive spectroscopic and HRESIMS analysis, as well as chemical methods. Compound 1 showed significant inhibitory effects with IC50 values of 7.6–11.2 μM against three human cancer cell lines, while compound 2 exhibited no hepatoprotective effect on CCl4-induced injury of human HepG2 cells, in the tested range of 0.1–100 μM.
4α-Methylergosta-22(E),24(28)-dien-3β-ol, a New Marine Sterol from the Octocoral Nephthea Columnaris
Authors: Lin Chin-Cheng , Whuang Ta-Yuan , Su Jui-Hsin , Hwangd Tsong-Long , Wu Ya-Chang , Sung Ping-Jyun
Published: March 2019

A new marine sterol, 4α-methylergosta-22( E),24(28)-dien-3β-ol (1), was isolated from the octocoral Nephthea columnaris. The structure of 1 was elucidated on the basis of spectroscopic and mass spectrometric methods.
Insecticidal Effect of Essential Oils against Fall Webworm (Hypantria cunea Drury (Lepidoptera: Arctiidae))
Authors: Gokturk Temel , Kordali Saban , Bozhuyuk Ayse Usanmaz
Published: March 2019

In this study, insecticidal effects of the essential oils obtained from plants Achillea biebersteinii Afan., Origanum onites L., Rosmarinus officinalis L., Salvia pratensis L., Satureja hortensis L., Tanacetum balsamita L. on American White Butterfly [ Hyphantria cunea Drury, Lepidoptera: Arctiidae] were tested in laboratory conditions. In this context, larvae of the 3rd and 4th periods of H. cunea were exposed to essential oils at doses of 10, 15 and 20 μl/petri for 24, 48, 72 and 96 hours. All of the essential oils used in the study caused mortality at different rates; the highest effect was obtained with the essential oil from O.onites with a mortality rate of 87.7%. The oils from R. officinalis (74.4%), A biebersteinii. (74.4%), S. hortensis (68.8%), T. balsamita (34.4%), and S. pratensis (30.0%) followed this in this order. As a results of the dose effect tests conducted in the second part of the study, it was determined that T. balsamita (LD50=7.1 ppm) and O. onites (LD90=23.2 ppm) were the most toxic plant essential oils when lethal concentration values (LD50 and LD90) were considered. It was found that the essential oils of R. officinalis (LD50 = 86.1 ppm) and S. hortensis (LD90=62722.1 ppm) have the lowest toxic effect. The results obtained show that the essential oils from A. biebersteinii, O. onites, and R. officinalis can be used in the fight against H. cunea.
Composition of Helichrysum thianschanicum Regel Essential Oil from Pamir (Tajikistan)
Authors: Sharopov Farukh S. , Sulaymonova Vasila A. , Sun Yanfang , Numonov Sodik , Gulmurodov Isomiddin S. , Valiev Abdujabbor Kh. , Aisa Haji Akber , Setzer William N.
Published: March 2019

Helichrysum thianschanicum Regel was collected from Khorugh town of Kuhistoni Badakhshon Autonomous Province of Tajikistan. The essential oil was obtained by hydrodistillation and analyzed by gas chromatography – mass spectrometry. A total of 67 compounds were identified representing 88.4% of the total essential oil composition. The major components of H. thianschanicum essential oil were ( E)-1-(6,10-dimethylundec-5-en-2-yl)-4-methylbenzene (pentylcurcumene) (21.6%), β-selinene (6.4%), δ-selinene (3.8%), (2 E, 6 E)-farnesol (3.3%), nerol (4.1%) and neryl decanoate (4.2%). To our best knowledge, no previous studies have been reported on the chemical composition of the essential oil of H. thianschanicum.
Chemical Constituents of Vitex trifolia Leaves
Authors: Ban Ninh Khac , Thoa Nguyen Thi Kim , Linh Tran My , Giang Vu Huong , Trang Do Thi , Nhiem Nguyen Xuan , Tai Bui Huu , Quang Tran Hong , Yen Pham Hai , Van Minh Chau , Van Kiem Phan
Published: March 2019

Using various chromatographic methods, one new lanostane triterpene, 3 α-hydroxylanosta-8,24 E-dien-26-oic acid (1), one new lignan, matairesinol 4'- O-β-D-glucopyranoside (2) along with five known compounds, ecdysone (3), 20-hydroxyecdysone (4), 20-hydroxyecdysone 2,3-monoacetonide (5), turkesterone (6), and polypodine B (7) were isolated from the leaves of Vitex trifolia L. Their structures were elucidated by 1D-, 2D-NMR spectroscopic analysis, HR-ESI-MS, CD, and by comparing with the NMR data reported in the literature.
Identification of the Metabolites of a Novel Anti-MRSA Compound, Kaempferol-3-O-Alpha-L-(2″,3″-di-p-coumaroyl)rhamnoside (KCR), Extracted from American Sycamore
Authors: Shaw Jiajiu , Swartz Kenneth , Valeriote Frederick , Media Joseph , Chen Ben , Hamann Mark T. , Wang Xiaojuan
Published: March 2019

Fractionation of an extract from American sycamore leaves produced the small molecule, kaempferol-3- O-alpha-L-(2″,3″-di- p-coumaroyl)rhamnoside (KCR), which exists in four stereoisomeric forms ( EE, EZ, ZE, and ZZ) at the olefin in the p-coumaroyl; all four isomers exhibit potent anti-MRSA activity in vitro. As part of the preclinical development of KCR, we set out to investigate the metabolites of KCR in mouse plasma as a prelude of ADME studies and therapeutic assessment. When KCR was added to mouse plasma at 37 °C, two new HPLC peaks appeared with increasing intensity as the incubation time increased; their retention times were shorter than that of KCR indicating that KCR was metabolized to produce two compounds that were more polar. HPLC results indicated that the two metabolites mainly came from the ZE and EE isomers and that the ZZ isomer was the most stable. Based on their respective HPLC retention times and UV spectra, these two metabolites were tentatively identified as p-coumaric acid and afzelin; both of which are more polar than KCR. The molecular weights of both metabolites were then confirmed by a Waters Acquity UPLC system with a QDa mass detector. UPLC chromatograms and molecular ions of metabolites 1 and 2 match well with those of reference materials, p-coumaric acid and afzelin, thus confirming the identities of the two major metabolites of KCR. In summary, KCR was metabolized in mouse plasma and two major metabolites ( p-coumaric acid and afzelin) were identified; the metabolites were mainly converted from the ZE and EE isomers.
Pharmaceutical, Ethnopharmacological, Phytochemical and Synthetic Importance of Genus Aerva: A Review
Authors: Musaddiq Sara , Mustafa Kiran , Ahmad Sajjad , Aslam Samina , Ali Basharat , Khakwani Samia , Riaz Naheed , Saleem Muhammad , Jabbar Abdul
Published: March 2019

Aerva plants are known widely for their exceptional medicinal uses. They have been employed conventionally for their medicinal properties by the common folk in several regions of the world. This indicates the efficacy of these remarkable herbs. They are also known for their multiple biological activities such as antioxidant, antibacterial, antilithiatic, hepatoprotective, antidiabetic, anticancer, antihyperlipidemic and nephroprotective potential. These pharmacological actions are associated with the presence of valuable nutrients and biochemical compounds such as sterols/terpenes, flavonoids, alkaloids, phenolics and sugars. The proper utilization of the substances obtained from these plants can enhance the finesse of the capabilities of these plants. These plants are not only medicinally important but are significantly serving several other scientific purposes. In the prospect of medicinal, scientific uses and the bioavailability of precious chemicals of Aerva species, a comprehensive review is compiled, which focuses on the detailed profile of biochemical compounds, pharmacological functions and biological activities of Aerva plants. The review also discusses the synthetic importance and the toxicity of these plants. The study aims to compile comprehensively what is already done and what more is needed to be done in the future investigations related to Aerva species.
Two New Antidepressant Steroidal Aglycones from Stephanotis mucronata
Authors: Hao Shu-Juan , Gao Li-Juan , Xu Shi-Fang , Ye Yi-Ping , Li Xiao-Yu
Published: March 2019

Two new C21 steroidal aglycones, 12- O-( N-methyl) anthraniloyl-deacylmetaplexigenin (1) and 12- O-tigloyl-20- O-tigloylsarcostin (2), were isolated from the hydrolyzed extract of the EtOAc soluble extract of the roots of Stephanotis mucronata. Their structures were determined on the basis of chemical evidence and extensive spectroscopic methods. The potential antidepressant activities of compounds 1 and 2 were evaluated in mice forced swimming test.
New Acetylated Terpenoids from Sponge Rhabdastrella providentiae Inhibit NO Production in LPS Stimulated BV2 Cells
Authors: Dung Duong Thi , Yen Pham Hai , Nhiem Nguyen Xuan , Quang Tran Hong , Tai Bui Huu , Van Minh Chau , Kim Dong Cheol , Oh Hyuncheol , Kim Youn Chul , Van Kiem Phan
Published: March 2019

Three new acetylated terpenoids, rhabdaprovidines A-C (1-3), were isolated from the Vietnamese sponge Rhabdastrella providentiae. Their chemical structures were established by HR-ESI-MS, 1D and 2D-NMR experiments. These compounds share 6,6,5-tricyclic nucleus of isomalabaricane-type triterpene, the specific secondary constituents from Rhabdastrella species. Compounds 1-3 inhibited NO production in LPS stimulated BV2 cells with IC50 values of 20.4 ± 1.5, 17.5 ± 0.9, and 46.8 ± 2.3 μM, respectively.
Curdepsidone A, a Depsidone from the Marine-Derived Endophytic Fungus Curvularia sp. IFB-Z10
Authors: An Fa-Liang , Liu Wei-He , Wei Xing-Chen , Pan Zheng-Hua , Lu Yan-Hua
Published: March 2019

A new depsidone, curdepsidone A (1), was isolated form the culture extracts of curvularia sp. IFB-Z10, a white croaker associated fungus. The structure of 1 was elucidated on the basis of extensive spectroscopic analyses (HRESIMS, 1D and 2D NMR). Compound 1 showed significant cytotoxicity against human hepatoma cell lines BEL7402 and BEL7402/5- FU with IC50 values of 9.85 μM and 2.46 μM, respectively.
Secondary Metabolites Isolated from Tricholoma Species (Basidiomycota, Tricholomatacee): A Review
Authors: Clericuzio Marco , Mellerio Giorgio Giacomo , Finzi Paola Vita , Vidari Giovanni
Published: March 2019

The large mushroom genus Tricholoma (Fr.) Staude comprises hundreds of species growing worldwide. Phytochemical studies on the contents of these mushrooms have been increasing steadily in the last decades; this review is the first complete report about the secondary metabolites isolated to date (January 2018) from the fruiting bodies, with the exclusion of most volatile constituents. The structures, presumed biogenesis, and bioactivities of identified compounds, divided in families according to their biogenesis, are critically discussed. A brief chemotaxonomic discussion of the genus Tricholoma is included in the final part of the review.
Trinulactones A–D, New Dinorsesterterpenoids from Streptomyces sp. S006
Authors: Wei Feifei , Li Wen , Song Rentai , Shen Yuemao
Published: March 2019

Four new dinorsesterterpenoids, designated as trinulactones A–D (1–4), were isolated from the Streptomyces sp. S006 strain. All the compounds contained a tricyclic skeleton, which was attached to a highly oxygenated unsaturated γ-lactone. Their structures were determined by analysis of their spectroscopic data, mainly 1D, 2D NMR and HR-ESIMS data. In particular, compounds 3a/3b and 4a/4b were identified individually as atropisomers.
Quantification of Sambucus nigra (Adoxaceae) Markers Related to Tincture Stability
Authors: Testoni Letícia D. , de Souza Angelita B. , Krueger Clarissa de M. A. , Quintão Nara L. M. , Couto Angelica G. , Bresolin Tania M. B.
Published: March 2019

Stability tests are essential to assuring herbal derivative quality, especially because of the complexity of the herbal matrix. To monitor the stability of Sambucus nigra L. flower tincture, a practical liquid chromatography (LC)-UV method was developed and validated. Rutin, the flower's pharmacopeial marker, in addition to other markers, isoquercitrin and quercetin, were quantified. The last two represent the degradation products of glycosylated flavonoids. In addition, other chromatographic peaks exhibiting typical flavonoid UV absorption profiles (total flavonoids) were also quantified and expressed in rutin equivalents. The method was developed with a reverse phase C18 column, using a gradient mobile phase at 0.7 mL min -1 at 30°C. The herbal drug and tincture obtained by percolation at 60 °C with ethanol 25% (v/v) were submitted to accelerated (40°C/75% RH, 2 months) and long duration (15–30°C, 6 months) studies. The LC-UV method was linear in the ranges of 1–200 μg mL-1 (rutin) and 1–100 μg mL-1 (isoquercitrin and quercetin), without interference of herbal matrix, and was precise (RSD ≤ 2.0% for intra and interday precision), selective, and robust (changes in mobile phase flow, pH and temperature). The tincture revealed the presence of quercetin, which was absent in the herbal drug, likely due to the hydrolysis process. After 2 months under accelerated study, the total flavonoids in the tincture decreased by approximately 20%, and after 6 months at room temperature, they decreased by approximately 30%. These results indicate the thermolability of the S. nigra tincture and the importance of monitoring phytomedicine stability.
A New Coumarin from the Roots of Heracleum dissectum
Authors: Zhang Changlong , Gao Yang , Peng Yajie , Zhang Xiaoqing , Zhang Hailong
Published: March 2019

A new coumarin with a ferulic acid moiety (1), together with three known coumarins, viz. isoscopletin-6-O- β-D-glucopyranoside (2), elebutheroside B1 (3), tert-O- β-D-glucopyranosyl-(R)-heraclenol (4), were isolated from the roots of Heracleum dissectum. Their structures were clarified by extensive spectroscopic data analysis including 1D and 2D NMR and HRESI MS and comparison with previous literatures (known compounds). Moreover, the absolute configuration of the new compound was also determined.