bluuebunny/crossref_metadata_2025 huggingface dataset:
Secondary Metabolites from the Aerial Parts of Salvia Aethiopis L
Authors: Malafronte Anna , Piaz Fabrizio Dal , Cioffi Giuseppina , Braca Alessandra , Leone Antonella , De Tommasi Nunziatina
Published: March 2019

Three new sesterterpenes (1–3), and one new diterpene (4) were isolated from the aerial parts of Salvia aethiopis L. (Lamiaceae), together with two known sesterterpenes, and four diterpenes. Their structural elucidation was accomplished by extensive spectroscopic methods including 1D (1H, 13C, 13C DEPT, TOCSY, NOESY) and 2D NMR experiments (DQF-COSY, HSQC, HMBC, ROESY), as well as ESIMS and chemical analysis.
An Immunomodulator from Terminalia Arjuna and Biological Evaluation of its Derivatives
Authors: Saxena Mohit , Yadav Sachidanand , Bawankule Dhyaneshwar U. , Srivastava Santosh K. , Pal Anirban , Mishra Rupal , Gupta Madan M. , Darokar Mahendra P. , Priyanka  , Khanuja Suman P. S.
Published: March 2019

Detailed chemical investigation of Terminalia arjuna bark resulted in the isolation and identification of an immunomodulatory constituent, arjunic acid (1), which was converted into seven semi-synthetic derivatives (2–8). All the test compounds in 0.1, 1 and 10 μg/mL concentrations exhibited immunomodulatory effects in a dose dependant manner. 2- O-Lauroyl arjunic acid (3) and 2- O-palmitoyl arjunic acid (4) exhibited immunostimulatory response at all the tested concentrations, while arjunic acid (1), 2,3-di- O-acetyl arjunic acid (2), 2,3-di -O-benzoyl arjunic acid (6), and 2- O-p-anisoyl arjunic acid (7) exhibited immunostimulatory responses at lower doses, whereas at higher concentrations they exhibited immunosuppressive activity. Only 2,3-di- O-palmitoyl arjunic acid (5) showed immunosuppressive activity at all the concentrations; this is being reported for the first time.
Triterpene Bisdesmosides from the Stems of Akebia Quinata
Authors: Mimaki Yoshihiro , Doi Saya
Published: March 2019

Five new triterpene saponins (1–5) were isolated from the stems of Akebia quinata. On the basis of extensive spectroscopic analysis, including 2D NMR data, and chemical evidence, the structures of the new compounds were determined to be 3β-[( O-β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl)oxy]-29-hydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (1), 3β-[( O-β-D-glucopyranosyl-(1→3)- O-[α-L-rhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl)oxy]-29-hydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (2), 3β-[( O-β-D-glucuronopyranosyl-(1→3)- O-[α-L-rhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl)oxy]-29-hydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (3), 3β-[( O-β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl)oxy]-23,29-dihydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (4), and 3β-[( O-β-D-glucopyranosyl-(1→3)- O-[α-L-rhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl)oxy]-23,29-dihydroxy-olean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (5), respectively.
Essential Oil Analysis and Antimicrobial Activity of Paeonia Mascula from Turkey
Authors: Yaylı Nurettin , Yaşar Ahmet , Yaylı Nuran , Albay Mesut , Coşkunçelebi Kamil
Published: March 2019

The present work describes the chemical composition and antimicrobial activity of the essential oil of Paeonia mascula (L) Miller collected in Torul, Gümüşhane-Turkey. The essential oil was obtained from all parts of the plant by hydrodistillation and analyzed by GC-FID and GC-MS. Twenty-five components representing 91.8% of the total oil were characterized and the main components of this species were found to be E-phytol (33.0%), hexahydrofarnesyl acetone (13.7%), Z-phytol (9.1%), geraniol (4.7%), and p-cymene (3.8%). The antimicrobial activity of the isolated essential oil of the plant was also investigated; it showed moderate activity against Yersinia pseudotuberculosis and Bacillus cereus.
Antimicrobial Activity of Nepeta Isolates
Authors: Mathela Chandra S. , Joshi Neeta
Published: March 2019

Iridodial β-monoenol acetate and actinidine, constituents of Nepeta leucophylla Benth and N. clarkei Benth respectively were investigated for their in vitro antimicrobial activity against 11 fungi and 8 bacteria. Both compounds demonstrated broad spectrum antifungal activity. Iridodial β-monoenol acetate showed remarkable activity against Penicillium citrinum and Aspergillus fumigates, while actinidine was most active against A. ochraceus. Both were moderately active against Bacillus anthracis and Streptococcus pyrogenes.
Rearranged Clerodane and Abietane Derived Diterpenoids from American Salvia Species
Authors: Esquivel Baldomero
Published: March 2019

The genus Salvia L. (Tribe Mentheae) is the largest of the Lamiaceae with 1000 species widespread throughout the world. Phytochemical studies of several Salvia species have established an interesting chemical profile for the genus including sterols, flavonoids and triterpenoids. However, the most characteristic secondary metabolites of the genus are diterpenoids. One of the most distinguishing features of Salvia genus is the number of rearranged diterpene skeletons isolated from these plants. Until now, over 30 rearranged diterpene skeletons have been described for both Old and New World representatives of the genus. In this review, a survey of recent literature data regarding rearranged clerodane and abietane diterpenoids from American Salvia species is presented.
Diterpenes from Euphorbia as Potential Leads for Drug Design
Authors: Barile Elisa , Corea Gabriella , Lanzotti Virginia
Published: March 2019

In the course of our chemical survey of bioactive plant metabolites, a large number of diterpenes have been isolated from Euphorbia species that showed interesting pharmacological activities. In particular, over sixty jatrophane, modified jatrophane, segetane, pepluane, and paraliane diterpenoids, fifty of them reported for the first time, were extracted, purified and characterized from Euphorbia dendroides, E. characias, E. peplus, E. amygdaloides, and E. paralias. The compounds based on jatrophane and modified jatrophane skeletons were shown to be potent inhibitors of P-glycoprotein, a membrane protein that confers upon cells the ability to resist lethal doses of certain cytotoxic drugs by pumping them out of the cells, thus resulting in a reduced cytotoxic effect. Those belonging to the rare classes of pepluane and paraliane were shown to be promising anti-inflammatory agents in vivo. In addition, by using LPS-stimulated J774 murine macrophages, it was demonstrated that the effect is ascribable to the reduction in the production of nitric oxide, prostaglandin E2 and TNF-α by inhibiting the expression of inducible nitric oxide synthase, cyclooxygenase-2 and TNF-α mRNA, respectively, through the down-regulation of NF-κB binding activity. The isolation of structurally-related analogues allowed us to perform SAR studies, which gave information on the key pharmacophoric elements of these new classes of promising drugs.
Comparative Evaluation of Antimicrobial Activity and Composition of Rose Oils from Various Geographic Origins, in Particular Bulgarian Rose Oil
Authors: Gochev Velizar , Wlcek Katrin , Buchbauer Gerhard , Stoyanova Albena , Dobreva Anna , Schmidt Erich , Jirovetz Leopold
Published: March 2019

In the present study we evaluated the composition and antimicrobial activity of various rose oils from Bulgaria, Turkey, Morocco, Iran and China against three Gram-positive, three Gram-negative bacteria and two yeasts. The composition of the studied essential oils was determined by GC and GC/MS. Citronellol was the major compound of all the oil samples: 31.7% (Chinese oil); 32.6% (Iranian oil); 33.6% (Moroccan oil); 34.9% (Bulgarian oil) and 38,7 % (Turkish oil). For the Bulgarian oil we could determine the highest activity against all microorganisms. Bacillus cereus ATCC 11778 was the most sensitive strain to Bulgarian rose oil (MCC 128 μg/mL) and Pseudomonas aeruginosa ATCC 9627 and P. fluorescens were more resistible strains (MCC 4096 μg/mL). Antimicrobial activity of rose oils is mainly due to the action of oxygenated acyclic monoterpenes citronellol, geraniol, nerol and linalool, their acetate derivatives and the phenolic compound eugenol.
Composition and Antimicrobial Analysis of the Essential Oil of Litsea Laevigata Nees. (Lauraceae)
Authors: Muhammed Arif M , Subbu Raj M , Jirovetz Leopold , Mohamed Shafi P
Published: March 2019

The essential oil of the berries of Litsea laevigata Nees., growing wild in Western Ghats, Kerala, India, was obtained by hydrodistillation and was fractionated by passage through a column using n-pentane and diethyl ether as eluents. The essential oil and its fractions were analysed by GC and GC-MS. Twenty seven compounds representing 99.2% of the original oil were identified. The major components are the terpene hydrocarbons trans-α-bergamotene(26.7%), α-pinene (25%) and β-pinene (8.2%). The antimicrobial activity of the essential oil and its fractions against four Gram-positive and four Gram-negative bacteria ( Staphylococcus aureus, Bacillus subtilis, Streptococcus faecalis, Staphylococcus albus, Escherichia coli, Pseudomonas aeruginosa, Proteus vulgaris, Klebsiella aerogenes), as well as two fungi ( Candida albicans, Aspergillus niger) was studied. The bioassay showed that the oil exhibited moderate to high antimicrobial activity, being very active against gram-positive bacteria, such as Streptococcus albus, and the fungus Aspergillus niger.
Development of a Miniaturized 24-well Strawberry Leaf Disk Bioassay for Evaluating Natural Fungicides
Authors: Wang Xiaoning , Wedge David E. , Tabanca Nurhayat , Johnson Robert D. , Cutler Stephen J. , Pace Patrick F. , Smith Barbara J. , Zhou Ligang
Published: March 2019

There is great incentive to discover biologically active natural products from higher plants that are more effective than synthetic agrochemicals and are environmentally safe. Research emphasis at the US Department of Agriculture has therefore been on the development of alternative approaches to utilizing natural plant products in pest management. Discovery and evaluation of natural product fungicides is largely dependent upon the availability of miniaturized antifungal bioassays. We report on the development of a miniaturized 24-well leaf disk assay for evaluating plant extracts and pure compounds. Compounds applied directly to the leaf surface can be evaluated in a dose-response for fungicidal activity and phytotoxicity. The assay is sensitive to microgram quantities, can determine chemical sensitivity between fungal isolates, and adaptable to complex mixtures, lipophilic extracts, and non-polar compounds. The use of digital imaging and analytical software provided quantitative data and the ability to fine tune the data analysis. Identification of new potential lead compounds can be repeated quickly in time and real on-the-leaf-surface activity can be evaluated in high throughput formats and published in a reasonable time.
Limonene - a Review: Biosynthetic, Ecological and Pharmacological Relevance
Authors: Erasto Paul , Viljoen Alvaro M.
Published: March 2019

Limonene is one of the most common compounds found in the essential oils of aromatic plants. The occurrence of this monoterpene hydrocarbon in various plant genera could be attributed to its precursory role in the biosynthesis of other monoterpenes and its defensive role against herbivores. Due to the medicinal potential and application in the flavor and fragrance industries, limonene has been extensively investigated. In this paper the biosynthetic, ecological and pharmacological importance of limonene is presented in an attempt to coherently summarize some of the most salient aspects from various studies in a form of a concise review.
Plant Secondary Metabolism: Diversity, Function and its Evolution
Authors: Wink Michael
Published: March 2019

A typical character of plants is the production and storage of usually complex mixtures of secondary metabolites (SM). The main function of secondary metabolites is defense against herbivores and microbes; some SM are signal compounds to attract pollinating and seed dispersing animals or play a role in the symbiotic relationships with plants and microbes. The distribution of SM in the plant kingdom shows an interesting pattern. A specific SM is often confined to a particular systematic unit, but isolated occurrences can occur in widely unrelated taxonomic groups. This review tries to explain the patchy occurrence of SM in plants. It could be due to convergent evolution, but evidence is provided that the genes that encode the biosynthesis of SM appear to have a much wider distribution than the actual secondary metabolite. It seems to be rather a matter of differential gene regulation whether a pathway is active and expressed in a given taxonomic unit or not. It is speculated that the genes of some pathways derived from an early horizontal gene transfer from bacteria, which later became mitochondria and chloroplasts. These genes/pathways should be present in most if not all land plants. About 80% of plants live in close symbiotic relationships with symbiotic fungi (ectomycorrhiza, endophytes). Recent evidence is presented that these fungi can either directly produce SM, which were formerly considered as plant SM or that these fungi have transferred the corresponding pathway gene to the host plant. The fungal contribution could also explain part of the patchy occurrence patterns of several secondary metabolites.
Major Constituents of the Predominant Endophytic Fungi from the Nigerian Plants Bryophyllum Pinnatum, Morinda Lucida and Jathropha Gossypiifolia
Authors: Sowemimo Abimbola A. , Edrada-Ebel RuAngelie , Ebel Rainer , Proksch Peter , Omobuwajo Olanrewaju R. , Adesanya Saburi A.
Published: March 2019

In a chemical screening of fungal strains endophytic to Nigerian plants, Diaporthe phaseolorum, the endophyte of Bryophyllum pinnatum, gave cytochalasin D and (3 R,4 R)-3,4,5-trihydroxy-1-tetralone, Neurospora discreta from Morinda lucida yielded multiforisin I and 4-hydroxyphenylacetic acid, while Aspergillus japonicus from Jatropha gossypiifolia gave (+)-eupenoxide and microsphaerone C, a new 4-pyridone derivative. When tested for cytotoxic activity, cytochalasin D displayed strong activity towards the mouse lymphoma cell line L5178Y, while the remaining compounds, except 4-hydroxyphenylacetic acid, were found to be moderately active.
Selective Elicitation of the Phytoalexin Rutalexin in Rutabaga and Turnip Roots by a Biotrophic Plant Pathogen
Authors: Pedras M. Soledade C. , Gadagi Ravi S. , Zheng Qing-An , Rimmer S. Roger
Published: March 2019

Stress responses of roots of rutabaga ( Brassica napus ssp. napobrassica) and turnip ( B. rapa ssp. rapa) were analyzed. Phytoalexin production due to biotic elicitation by the biotroph Albugo candida and abiotic elicitation using UV irradiation was quantified by HPLC. The phytoalexin rutalexin was produced in substantially higher amounts in rutabaga and turnip roots inoculated with A. candida than in UV irradiated roots. By contrast, production of the phytoalexins brassinin in rutabaga and cyclobrassinin in turnip was higher in UV irradiated roots than in roots inoculated with A. candida. Overall, the results suggest that A. candida is able to redirect the phytoalexin biosynthetic pathway towards rutalexin, a phytoalexin substantially less inhibitory than either brassinin or cyclobrassinin.
Unraveling the Biochemical Base of Dahlia Flower Coloration
Authors: Halbwirth Heidi , Muster Gerlinde , Stich Karl
Published: March 2019

Dahlia ( Dahlia variabilis) exists in a dazzling array of cultivars, showing red, orange, magenta, lilac, yellow and white flower color, which is exclusively based on the presence of flavonoids and biochemically related compounds. Red hues (red, orange, magenta, lilac) are a result of anthocyanin accumulation in varying concentration and composition, while a yellow color is based on the formation of 6′-deoxychalcones in the petals. Red dahlia pigments are all derived from pelargonidin and cyanidin. Delphinidin derivatives are not formed due to the absence of flavonoid 3′,5′-hydroxylase in dahlia petals, which provides an explanation for the lack of blue dahlia flowers. Orange, lilac and rose cultivars are characterized by a lower anthocyanin content compared to many red cultivars. We investigated 198 cultivars for the presence of flavonoid enzymes. The activities of chalcone isomerase (CHI), chalcone synthase (CHS), dihydroflavonol 4-reductase (DFR), flavanone 3-hydroxylase (FHT), flavone synthase II (FNSII), flavonol synthase (FLS) and flavonoid 3′-hydroxylase (F3′H) were demonstrated in enzyme preparations of dahlia petals. CHI accepted 6′-hydroxychalcones as substrates, but did not catalyze the conversion of 6′-deoxychalcones to the corresponding flavanones. White cultivars were frequently characterized by the lack of DFR activity, whereas in many yellow cultivars neither FHT nor DFR activity could be shown.
Bioisosteric Replacement of Molecular Scaffolds: From Natural Products to Synthetic Compounds
Authors: Grabowski Kristina , Proschak Ewgenij , Baringhaus Karl-Heinz , Rau Oliver , Schubert-Zsilavecz Manfred , Schneider Gisbert
Published: March 2019

Natural products often contain scaffolds or core structures that prevent immediate synthetic accessibility. It is, therefore, desirable to find isosteric chemotypes that allow for scaffold-hopping or re-scaffolding. The idea is to obtain simpler chemotypes that are synthetically feasible and exhibit either the same or similar bioactivity as the original natural product or reference compound. We developed and applied a virtual screening technique that represents a molecular scaffold by its side-chain attachment points (exit-vectors) and properties of the side-chain substituents. The technique was validated by retrospective screening for beta-turn mimetics and HMG-CoA inhibitors. A prospective application aimed at finding new chemotypes of PPAR-alpha agonists. Two such compounds were found in a commercially available screening compound library yielding EC50 values in the low micromolar range. This study demonstrates the applicability of exit-vector based virtual screening to scaffold-hopping tasks.
Composition of Essential Oil from Lavandula Angustifolia and L. Intermedia Varieties Grown in British Columbia, Canada
Authors: Lane W. Alexander , Mahmoud Soheil S.
Published: March 2019

Lavender essential oils have been used since antiquity as natural active constituents in products designed for dealing with a broad range of issues including those related to human hygiene, health and personal care, and those concerned with organic agriculture and pest management. The recent and rapidly growing public interest in “natural products” has renewed attention to these plants. Here we report on the composition and insect repellent properties of the essential oils obtained from 12 varieties of the two most commonly cultivated lavender species ( L. angustifolia and L. intermedia), grown in an experimental plot in the Okanagan Valley of British Columbia, Canada. For comparison, we also analyzed oil composition for three additional lavender oil samples. Our results demonstrate that the locally grown plants produce essential oils that are similar to those found in other parts of the world in terms of the overall olfactory properties, and in that they contain the same constituents found in comparable lavender oils. Some of these oils, including those extracted from Premier, Grosso, Hidcote Giant, and Mailette exhibited potent insect repellent properties.
6-Bromo-5-hydroxyindolyl-3-glyoxylate from the Far Eastern Ascidian Syncarpa oviformis
Authors: Santalova Elena A. , Denisenko Vladimir A. , Berdyshev Dmitry V. , Aminin Dmitry L. , Sanamyan Karen E.
Published: March 2019

The ethanol extract of the marine ascidian Syncarpa oviformis (Kuril Islands, Russia) has been shown to contain three indole derivatives, ethyl indolyl-3-glyoxylate (1), ethyl 6-bromoindolyl-3-glyoxylate (2), and ethyl 6-bromo-5-hydroxyindolyl-3-glyoxylate (3), along with p-hydroxyphenylglyoxylate, 2,6-dimethylheptyl sulfate and (3 Z)-3-decenyl sulfate. The structure of the novel compound 3 has been elucidated on the basis of NMR, MS, IR and UV analyses.
Guaiane Sesquiterpenoids from Jatropha curcas
Authors: Wang Xia-Chang , Ma Shi-Ping , Liu Jing-Han , Hu Li-Hong
Published: March 2019

Two new guaiane sesquiterpenoids named jatrophaols A and B (1, 2), along with three known analogues, were isolated from the roots of Jatropha curcas. Their structures were determined by spectroscopic methods, including 1D and 2D NMR spectroscopy, HR-EI-MS, HR-ESI-MS, and X-ray diffraction, as well as by comparison of their spectral data with those of related compounds.
Sesquiterpenes of the Brazilian Marine Red Alga Laurencia filiformis (Rhodophyta, Ceramiales)
Authors: Antunes Bruno Lopes , Fleury Beatriz Grosso , Fujii MutueToyota , Teixeira Valéria Laneuville
Published: March 2019

Sesquiterpenes from the red algal genus Laurencia appear to be valuable taxonomic markers and have shown, for various species, strong correlation with morphological data. In the present study, four chamigrane sesquiterpenes (1–4) were isolated from L. filiformis collected in Salvador, Brazil; these compounds have also been reported for L. scoparia. As discussed by various phycologists, Brazilian specimens of L. scoparia should be considered synonymous with L. filiformis.
New Pyrenocines from an Endophytic Fungus
Authors: Krohn Karsten , Sohrab Md. Hossain , Draeger Siegfried , Schulz Barbara
Published: March 2019

Three new pyrenocines, F (6), G (7), and H (8), along with the known pyrenocine A (1) were isolated from the ethyl acetate extract of an unidentified endophytic fungus. Metabolites 1 and 7 exhibited good antifungal and algicidal activities.
Chemoenzymatic Synthesis and Some Biological Properties of O-phosphoryl Derivatives of (E)-resveratrol
Authors: Aleo Danilo , Cardile Venera , Chillemi Rosa , Granata Giuseppe , Sciuto Sebastiano
Published: March 2019

3- O-, 3,5-di- O- and 4′- O-phosphoryl derivatives of ( E)-resveratrol have been obtained following a chemoenzymatic strategy. Variedly acylated resveratrol derivatives have been obtained first by exploiting regioselective properties of Pseudomonas cepacea or Candida antarctica lipases in organic solvents. Each acyl-resveratrol was then phosphorylated by the phosphoramidite chemistry protocol and in sequence freed of protective groups, affording the desired O-phosphoryl derivative. Following UV-absorption spectroscopic investigation on the interaction of the newly synthesized compounds with DNA, 4′- O-phosphorylresveratrol exhibited the best binding affinity. As a result of cytotoxicity tests, 3- O-phosphorylresveratrol was more active than resveratrol against DU 145 prostate cancer cells.
In vitro Cytotoxic Activity of Sesamin Isolated from Vismia baccifera var. dealbata Triana & Planch (Guttiferae) Collected from Venezuela
Authors: Salas Fabiola , Rojas Janne , Morales Antonio , Ramos-Nino Maria E. , Colmenares Nelida G.
Published: March 2019

Sesamin extracted from Vismia baccifera var. dealbata was demonstrated to have cytostatic activity on the cancer cell lines tested, particularly the lung cancer cell line, with an IC50 of 1 g/L.
A New Flavonoid Glycoside from the fern Dryopteris Villarii
Authors: Imperato Filippo
Published: March 2019

A new flavonoid, identified as kaempferol 3- O-(4′”- O-acetylrutinoside) by chemical and spectral methods, has been isolated from aerial parts of the fern Dryopteris villarii, together with the new fern constituent, chrysin 3- O-rutinoside, and kaempferol 3- O-rhamnoside-7- O-glucoside.
Antimicrobial Activity and Chemical Composition of Melaleuca genistifolia Leaf Essential Oil from the Northern Plains of India
Authors: Kumar Ajai , Srivastava Santosh K. , Dwivedi Gaurav R. , Khan Merajuddin , Darokar Mahendra P. , Saxena Mohit , Syamsundar Kodakandla V. , Luqman Suaib , Khanuja Suman P. S.
Published: March 2019

Biological and chemical investigations were carried out to evaluate the antimicrobial potential of Melaleuca genistifolia leaf oil for herbal medicines. The disk diffusion and micro broth dilution methods were used for the evaluation of the antimicrobial activity of the essential oil and its major constituent, methyl eugenol against the five selected bacterial and five fungal strains. The oil was active against all the tested bacterial and fungal strains. The oil was highly active against Staphylococcus epidermidis and significantly active against S. aureus, Sporothrix schenckii and Trichophyton rubrum, while methyl eugenol was significantly active against Enterococcus faecalis, Streptococcus mutans and Escherichia coli. GC and GC-MS analysis of the oil resulted in the identification of twenty two constituents representing 99.4% of the oil. The chemo type identified had a high methyl eugenol (88.1%) content. The essential oil could be of use for the future development of antimicrobial herbal products.
Asymmetric N-Acyliminium Cyclization as an Approach to Heterocyclic Natural Product Synthesis
Authors: Gaskell Sean N. , Duffy Liam J. , Allin Steven M.
Published: March 2019

This paper describes the development of a highly stereoselective N-acyliminium cyclization protocol for the construction of a range of non-racemic heterocyclic templates. Due to the nature of this review, we have focused primarily on developments made within our own research group, but have included relevant and noteworthy contributions in the same area from others, most notably the research groups of Amat, Bosch and Lete. As a result, we apologize in advance for the omission of much excellent work carried out by many other talented researchers in this field.
New Purine Derivatives from the Marine Sponge Petrosia nigricans
Authors: Ashour Mohamed , Edrada-Ebel RuAngelie , Ebel Rainer , Wray Victor , van Soest Rob.W.M. , Proksch Peter
Published: March 2019

Four new purine analogues (nigricines 1 – 4) have been isolated from the Indonesian marine sponge Petrosia nigricans. The structures were elucidated by extensive 2D-NMR spectroscopic experiments and mass spectrometry.
Comparison of the Chemical Compositions of the Essential Oils from the Aerial Parts, Fruits and Roots of Nigerian Laportea aestuans (L.) Chew (Urticaceae)
Authors: Olufunke Moronkola D. , Adebayo Oladosu I. , Ajani Ogunwande I. , Ose Olubomehin
Published: March 2019

Essential oils obtained by hydrodistillation, using an all-glass apparatus, from the aerial parts, fruits and roots of Laportea aestuans (L.) Chew were analyzed using GC and GC-MS. From the oil of the aerial parts, 27 out of the 33 detected compounds, representing 95.1% of the total oil, were characterized. For the fruit oil, 10 out of 12 detected compounds were identified (89.3% of total), and for the root oil 19 of the 22 compounds (98.6%). The dominant components of the oil of the aerial parts were methylcyclohexane (20.9%), isodecyl octyl 1,2-benzenedicarboxylate (9.2%), di-n-octyl phthalate (9.0%), bis(7-methyloctyl)phthalate (7.0%), and toluene (6.9%); in the fruit oil, butyl 8-methylnonyl-1,2-benzenedicarboxylate (14.6%), 8-decyloxy-3-phenyl-2,4,7-trioxabicyclo[4.4.0]dec-9-ene (13.7%), dicyclohexyl-1,2-benzene dicarboxylate (13.6%), didodecyl phthalate (12.0%), and butyl-8-methylnonyl-1,2-benzenedicarboxylate (11.3%); and in the root oil, di-n-octyl phthalate (36.8%), butyldecyl-1,2-benzenedicarboxylate (7.5%), bis(2-ethylhexyl)hexanedioate (6.4%), butyl-2-ethylhexyl-1,2-benzenedicarboxylate (5.4%), and bis(2-ethylbutyl)-1,2-benzenedicarboxylate (5.0%)].
A Polar Cannabinoid from Cannabis Sativa Var. Carma
Authors: Appendino Giovanni , Giana Anna , Gibbons Simon , Maffei Massimo , Gnavi Giorgio , Grassi Gianpaolo , Sterner Olov
Published: March 2019

The aerial parts of Cannabis sativa var. Carma afforded a novel polar cannabinoid whose structure was established as rac-6′,7′-dihydro,6′,7′-dihydroxycannabigerol (carmagerol, 1) on the basis of spectroscopic data and semisynthesis from cannabigerol (2a). The dihydroxylation of the ω-double bond was detrimental to the anti-bacterial activity.
Diterpenoid Alkaloids and Phenol Glycosides from Aconitum Naviculare (Brühl) Stapf
Authors: Dall'Acqua Stefano , Shrestha Bharat B. , Gewali Mohan Bikram , Jha Pramod Kumar , Carrara Maria , Innocenti Gabbriella
Published: March 2019

Phytochemical investigation of the aerial parts of Aconitum naviculare, a medicinal plant used in traditional Nepalese medicine, led to the isolation and characterization of two new diterpenoid alkaloids, navirine B (1), and navirine C (2), along with (+) chellespontine (3), kaempferol-7-O-β-D-glucopyranosyl(1→3)α-L-rhamnopyranoside (4), kaempferol-7-O α-L-rhamnopyranoside,3-O-β-D-glucopyranoside (5), p-coumaric-4-O-β-D-glucopyranoside acid (6), and ferulic-4-O-β-D-glucopyranoside acid (7). The structures of the isolated compounds were elucidated on the basis of extensive analyses of 1D and 2D NMR spectra (HMQC, HMBC, COSY, ROESY) and HR-MS data. The antiproliferative activity of alkaloids 1–3 against human tumor cell lines (LoVo and 2008) was also evaluated.
Inhibition of PGHS-1 and PGHS-2 by Triterpenoid Acids from Chaenomelis Fructus
Authors: Reininger Eveline , Bauer Rudolf
Published: March 2019

The dichloromethane extract of the dried fruits of Chaenomeles speciosa (Sweet) Nakai (Rosaceae) showed strong inhibitory activity against both prostaglandin-H-synthase isoenzymes [IC50 (PGHS-1) = 5.1 μg/mL; IC50 (PGHS-2) = 2.3 μg/mL]. The lipophilic portion of the extract was mainly responsible for the inhibitory effect. Several triterpenoid acids were isolated and identified as contributing to this inhibitory activity (oleanolic, pomolic, 3β-O-acetylursolic and 3β-O-acetylpomolic acids). Comparison of their inhibitory potential with their selectivity to PGHS-2 showed that 3β-O-acetylursolic acid had the highest potency in the inhibition of PGHS-1 and PGHS-2 enzymes, whilst pomolic and 3β-O-acetylpomolic acid, with a hydroxyl group at position 19α, showed selectivity for PGHS-2. The inhibitory effect of the extract seems to be the result of the activity of the mixture of these different triterpenoid acids.
Preparative Isolation of Antimycobacterial Shoreic Acid from Cabralea canjerana by High Speed Countercurrent Chromatography
Authors: Leitão Gilda G. , Abreu Lisandra F. , Costa Fernanda N. , Brum Thiago B. , Ramos Daniela Fernandes , Silva Pedro Eduardo A. , Lourenço Maria Cristina S. , Leitão Suzana G.
Published: March 2019

High speed countercurrent chromatography (HSCCC) was used to isolate the dammarane type triterpene shoreic acid from the dichloromethane extract of leaves of Cabralea canjerana, which showed activity against Mycobacterium tuberculosis. A preparative scale-up of the process was also developed.
Antiplasmodial Effects of a few Selected Natural Flavonoids and their Modulation of Artemisinin Activity
Authors: Bilia Anna Rita , Sannella Anna Rosa , Vincieri Franco Francesco , Messori Luigi , Casini Angela , Gabbiani Chiara , Severini Carlo , Majori Giancarlo
Published: March 2019

The direct antiplasmodial effects of five structurally-related flavonoids, namely quercetin, rutin, eriodictyol, eriodictyolchalcone and catechin, were analyzed in vitro on P. falciparum. Notably, all these flavonoids, with the only exception of rutin, caused relevant inhibition of P. falciparum growth when given at 1 mM concentration. In addition, they were found to affect greatly the potent antiplasmodial activity of artemisinin, leading to significant additive and even synergistic effects. In particular, quercetin induced a pronounced synergistic effect. The observed synergisms might be conveniently exploited to design new and/or more effective combination therapies.
In Vitro Radical Scavenging and Anti-Yeast Activity of Extracts from Leaves of Aloe Species Growing in Congo
Authors: Romani Annalisa , Vignolinia Pamela , Isolani Laura , Tombelli Sara , Heimler Daniela , Turchetti Benedetta , Buzzini Pietro
Published: March 2019

Extracts obtained from leaves of Aloe barbadensis and A. congolensis, growing in Congo, were analyzed for their in vitro antiradical and anti-yeast activity. Different leaf tissues (tegument and gel) were analyzed separately. Their phenolic fractions showed the presence of chromones and anthrones (aloesin, aloin B, aloin A, and isoaloeresin), flavonoids (apigenin and kaempferol derivatives), and hydroxycinnamic acids. A differential quantitative composition was observed between leaf tegument and gel: in the first, higher concentrations of the four classes of compounds were observed. The extracts from the tegument exhibited higher in vitro antiradical and antimycotic activity than gel extracts. In a few cases, extracts from teguments were active against amphotericin B-insensitive yeasts. Due to the lack of radical scavenging and yeast inhibition observed when aloin was used, it was possible to postulate that the in vitro activities of the teguments could be related to their high concentration of flavonoids and hydroxycinnamic acids.
Antioxidant Principles and Volatile Constituents from the North-Western Iberian Mint “Erva-Peixeira”, Mentha Cervina
Authors: Politi Matteo , Rodrigues César L , Gião Maria S , Pintado Manuela E , Castro Paula ML
Published: March 2019

Total phenol content determined by the Folin-Ciocalteu assay and total antioxidant capacity measured by the ABTS•+ method were applied for the first time to analyze the aqueous extract prepared from the dried aerial parts of Mentha cervina, a Portuguese mint species traditionally used as a culinary herb in river fish-based dishes and currently commercialized to prepare digestive infusions. LC-MS/MS analysis was performed directly on the crude aqueous extract allowing the identification of seven phenolic compounds. The overall plant aroma was analyzed by the SPME/GC-MS method; this approach allowed the characterization of various constituents, as well as the comparison between the fresh and dried plant material. Such a comparison highlighted several metabolic changes that occur during the drying process of the aerial parts of this plant.
Antihyperalgesic Effect of Eschscholzia Californica in Rat Models of Neuropathic Pain
Authors: Vivoli Elisa , Maidecchi Anna , Bilia Anna Rita , Galeotti Nicoletta , Norcini Monica , Ghelardini Carla
Published: March 2019

Eschscholzia californica Cham. (Papaveraceae) is traditionally used by the Indians as a medicinal plant for its anxiolytic, anticonflict, analgesic and sedative properties. The mechanisms of action for the sedative and anxiolytic activities have not been clearly established and so to further investigate the pharmacological profile of E. californica in some painful conditions, a 70% v/v ethanol extract, DERnative=5:1, was tested in rat models of neuropathy induced by chronic constriction injury of the sciatic nerve (CCI), with chemotherapeutic oxaliplatin, and osteoarthritis caused by intrarticular injection of monoiodoacetate. In the CCI model evaluated in the rat paw-pressure test, the examined extract (100 mg kg−1 p.o.) showed an antihyperalgesic effect. Eschscholzia extract, after single injection at a dose of 100–300 mg kg−1 p.o., produced also a statistically significant decrease of pain perception on hyperalgesia induced by oxaliplatin and osteoarthritis, while in the same condition gabapentin did not display any antihyperalgesic effect. Furthermore, in the range of antihyperalgesic doses, the extract was efficacious in the hot-plate (thermal stimulus) and carrageenan tests (inflammatory model) without producing any behavioral impairment, as evaluated by the Irwin test. The analgesic effect exhibited by Eschscholzia extract in the mouse hot-plate test was not antagonized by naloxone, indicating that opioid neurotransmission is not involved in the effect.

The above reported results suggest that a 70% (v/v) ethanol dried extract (DERnative=5:1) of E. californica might represent a promising product for the therapy of acute and chronic pain.
A New Dolabrane-type Diterpene from Ceriops tagal
Authors: Ouyang Xiao-Wei , Wang Xia-Chang , Yue Qing-Xi , Hu Li-Hong
Published: March 2019

A new dolabrane-type diterpene named tagalsin O 1, together with six known analogues 2-7, were isolated from the aerial part of the mangrove plant Ceriops tagal. The structures and relative configurations were elucidated on the basis of their spectroscopic data. Cytotoxicity of the isolated compounds against HeLa human cervical carcinoma cancer cell line was evaluated.
Plakinamine L: A New Steroidal Alkaloid from the Marine Sponge Corticium sp
Authors: Aknin Maurice , Rudi Amira , Kashman Yoel , Vacelet Jean , Gaydou Emile M.
Published: March 2019

A new steroidal alkaloid, plakinamine L (1) with an unprecedented acyclic side chain, was isolated from the marine sponge Corticium sp. collected near Salary (south-west of Madagascar). The structure was elucidated by combined spectroscopic methods.
Influence of the Extraction Method on the Yield of Flavonoids and Phenolics from Sideritis spp. (Pirin Mountain tea)
Authors: Alipieva Kalina , Petreska Jasmina , Gil-Izquierdo Ángel , Stefova Marina , Evstatieva Ljuba , Bankova Vassya
Published: March 2019

The influence of the extraction method on the yield and composition of extracts of Sideritis (Pirin mountain tea) has been studied. Maceration, ultrasound-assisted (USAE) and microwave assisted extraction (MAE) were applied. Total phenolics and total flavonoids were quantified spectrophotometrically, and individual compounds were analyzed by HPLC-DAD-MSn. This preliminary study reveals that the traditional way of tea preparation from Sideritis is the most appropriate in order to extract the maximum of total flavonoids and total phenolics. In the case of methanol extraction, the optimal method is USAE
A New Phenolic and a New Lignan from the Roots of Juniperus chinensis
Authors: Chang Chi-I , Chen Chiy-Rong , Chen Wen-Ching , Kuo Chao-Lin , Kuo Yueh-Hsiung
Published: March 2019

A new phenolic, (4-hydroxy-2-isopropylphenyl)ethanoic acid and a new lignan, epi-calocedrin were obtained from the roots of Juniperus chinensis Linn. The structures were elucidated on the basis of spectroscopic analysis and chemical evidence.
Flavones from the Stem of Andrographis paniculata Nees
Authors: Radhika Parvataneni , Prasad Yejella Rajendra , Lakshmi Koduru Rajya
Published: March 2019

Chemical investigation of Andrographis paniculata Nees (Acanthaceae) resulted in the isolation of three flavones identified as 5-hydroxy-7,8,2′-trimethoxyflavone 1, 5-hydroxy-7,8-dimethoxyflavone 2 and 5-hydroxy-7,8,2′,5′-tetramethoxyflavone 3 from the hexane, methanol and chloroform extracts of the root and stem.
Inhibitory Effects of Indirubin Derivatives on the Growth of HL-60 Leukemia Cells
Authors: Cuong Nguyen Manh , Tai Bui Huu , Hoan Dang Hoang , Huong Tran Thu , Kim Young Ho , Hyun Jae-Hee , Kang Hee-Kyoung
Published: March 2019

Six indirubin derivatives have been synthesized and their inhibitory effects on the growth of HL-60 human promyelocytic leukemia cells investigated. Cell viability was determined using the trypan blue exclusion method. Indirubin-3′-oxime (I-1) inhibited the growth of HL-60 cells with a GI50 value of 36.6 μM, whereas I-0, I-2, I-3, I-4 and I-6 showed only weak cytotoxic activities against HL-60 cancer cells with GI50 values in the range of 97.3 to over 100 μM. These results indicate that indirubin derivatives might be useful candidate agents for exploring potential antileukemic drugs.
Essential Oil Composition of Achillea clusiana from Bulgaria
Authors: Trendafilova Antoaneta , Todorova Milka , Vitkova Antonina
Published: March 2019

The essential oil compositon of Achillea clusiana Tausch from Bulgaria has been studied by GC and GC/MS. Fifty-four components were registered, representing 92.5% of the oil. The oil was characterized by the presence of oxygenated mono- and sesquiterpenoids. The main components were β-thujone (17.2%), 1,8-cineole (11.2%), camphor (11.1%) and α- thujone (7.8%). Farnesol (3.1%), nerolidol (2.7%) and oxygenated nerolidol derivatives (cabreuva oxides A-D, isohumbertiols A-D, bejarol and 7-hydroxy-6,7-dihydro-5,6E-dehydronerolidol) were the main sesquiterpenoids in the oil.
Effects of Essential Oils on the Growth of Giardia lamblia Trophozoites
Authors: Machado Marisa , Sousa Maria do Céu , Salgueiro Lígia , Cavaleiro Carlos
Published: March 2019

Giardia lamblia is one of the most important worldwide causes of intestinal infections produced by protozoa. Current therapy for giardiasis is unsatisfactory due to high incidence of undesirable side effects and significant failure in clearing parasites from the gastrointestinal tract. In the search for new therapeutic agents, we report on the effect of several essential oils on G. lamblia growth. Among eighteen tested essential oils, those with phenolic compositions were the most active, particularly if containing high contents of carvacrol, such as Thymbra capitata and Origanum virens (IC50 values of 71 and 85 μg.mL−1, respectively). The oils from Syzygium aromaticum and Thymus zygis subsp. sylvestris (IC50 values from 100 to 200 μg.mL−1), as well as, those from Mentha x piperita and Lippia graveolens (IC50 values over 200 μg.mL−1) were less active. Results support the concept that several essential oils or some of their constituents may be useful in the clinical management of Giardia infections.
Two New Terpenoids from Trichilia quadrijuga (Meliaceae)
Authors: Rodrigues Virginia F. , Carmo Hadria M. , Filho Raimundo Braz , Mathias Leda , Vieira Ivo J. Curcino
Published: March 2019

Two new terpenoids, ambrosanoli-10(14)-en-11,12-diol (1), a sesquiterpene named quadrijugol, and a pregnane steroid, 3β,4β-dihydroxypregnan-16-one (2), were isolated from the stem and leaves of Trichilia quadrijuga, along with eleven known compounds, spathulenol, kudtdiol, 2β,3β,4β-trihydroxypregnan-16-one, bourjotinolone B, piscidinol, niloticin, dihydroniloticin, β-sitosterol, 3-O-β-D-glucopyranosyl-sitosterol, itesmol and stigmasterol. Structures were elucidated by spectral data analysis, mainly afforded by 1H and 13C NMR (1D and 2D NMR HMQC, HMBC, NOESY and COSY) and mass spectra.
Steroids from the South China Sea Gorgonian Subergorgia suberosa
Authors: Qi Shu-Hua , Gao Cheng-Hai , Qian Pei-Yuan , Zhang Si
Published: March 2019

From the South China sea gorgonian Subergorgia suberosa, two new steroids, (22E)-14α-hydroxy-cholesta-1,4,22-trien-3-one (1) and 3-(1′,2′-ethandiol)-cholest-3β,5α,6α, 11α-tetraol (2) were obtained, in addition to six known steroids. The structures of compounds 1 and 2 were determined by spectroscopic methods. Cytotoxicity of the six known steroids against human cancer cell lines A549, HONE1, and HeLa was evaluated by MTT methods, and their anti-larval activity was evaluated in settlement inhibition assays with laboratory-reared Balanus amphitrite and Bugular neritina larvae.
Auroside, a Xylosyl-sterol, and Patusterol A and B, two Hydroxylated Sterols, from two Soft Corals Eleutherobia aurea and Lobophytum patulum
Authors: Yeffet Dina , Rudi Amira , Ketzinel Sharon , Benayahu Yehuda , Kashman Yoel
Published: March 2019

A new sterol glycoside, auroside (1) and two new hydroxylated sterols, patusterol A and B (2, 3) have been isolated from the South African soft coral Eleutherobia aurea and from the Kenyan soft coral Lobophytum patulum. The structure elucidation was achieved from extensive 1D- and 2D- NMR and MS data, and in the case of auroside also by chemical reactions. In addition, from Lobophytum patulum, was also isolated a known nitrogen containing compound (Z)-N-[2-(4-hydroxyphenyl)ethyl]-3-methyldodec-2-enamide, and from Eleutherobia aurea several, earlier reported, diterpenoids. Compound 2 was found to be toxic to brine shrimp embryos with an LC50 value of 2.30 μM.
Secondary Metabolites of the Phytopathogen Peronophythora litchii
Authors: Xie Haihui , Liang Yaoguang , Xue Jinghua , Xu Qiaolin , Jiang Yueming , Wei Xiaoyi
Published: March 2019

Two new metabolites, 4R*-hydroxy-3,5R*-dimethoxycyclohex-2-enone (1) and 2-hydroxy-N-(2-hydroxyphenyl)propionamide (2), were isolated from solid cultures of the phytopathogen Peronophythora litchii, along with 4-hydroxybenzyl alcohol (3) and methyl D-indole-3-lactate (4). Their structures were elucidated on the basis of spectroscopic and spectrometric data. These metabolites were not toxic to brine shrimps (LC50 > 500 μg/mL).
Salaramides A and B; Two α-Oxoamides Isolated from the Marine Sponge Hippospongia sp. (Porifera, Dictyoceratida)
Authors: Bensemhoun Julia , Rudi Amira , Kashman Yoel , Gaydou Emile M. , Vacelet Jean , Aknin Maurice
Published: March 2019

Two novel α-oxoamides, salaramide A (1) and its homologue salaramide B (2), were isolated from the Madagascar marine sponge, Hippospongia sp., collected in Salary Bay, north of Tulear. The structures of 1 and 2 were elucidated by interpretation of mass spectra, 1D and 2D NMR spectra, and confirmed by chemical transformation.
Compositional Variability in Essential Oil from Different Parts of Alpinia speciosa from India
Authors: Padalia Rajendra C. , Chanotiya Chandan S. , Sundaresan V.
Published: March 2019

The essential oils from the leaves, flowers and roots of cultivated Alpinia speciosa K. Schum. were examined by capillary GC and GC-MS. Monoterpenoids composed 89.6% of the total identified constituents of the leaf oil, out of which 59.3% were oxygenated, represented mainly by terpinen-4-ol (28.4%) and 1,8-cineole (19.2%). The flower and leaf oils had a uniform qualitative, but different quantitative composition. However, the flowers oil was also dominated by oxygenated monoterpenoids (68.9%) viz., terpinen-4-ol (26.0%), 1,8-cineole (24.4%) and linalool (6.1%), along with the monoterpene hydrocarbon, sabinene (11.3%). On the contrary, the root oil had an entirely different composition and was characterized by endo-fenchyl acetate (40.1%), 1,8-cineole (11.8%), camphene (7.8%), bornyl acetate (6.9%) and borneol (5.8%). Moreover, endo-fenchyl acetate, exo-fenchyl acetate and endo-fenchol were characteristic of only the A. speciosa root oil.
Biological Activity of Essential Oils from Aloysia polystachya and Aloysia citriodora (Verbenaceae) against the Soybean Pest Nezara viridula (Hemiptera: Pentatomidae)
Authors: Werdin González Jorge O. , Gutiérrez María M. , Murray Ana P. , Ferrero Adriana A.
Published: March 2019

The objective of the current study was to determine the chemical constituents, ovicidal activity, fumigant, contact toxicity and repellent effects of essential oils isolated by hydrodistillation from Aloysia polystachya and A. citriodora against eggs and second instar nymphs of Nezara viridula. The major components were carvone (83.5%) for A. polystachya, and citronellal (51.3%) and sabinene (22.9%) for A. citriodora. The ovicidal activity of both oils was tested by topical application at different concentrations ranging from 1.2 to 12.5 μg/egg; all concentrations had a toxic effect. Data probit analysis showed that the LC50 value for A. polystachya was 2.3 μg/egg and for A. citriodora 1.9 μg/egg. The fumigant activity was evaluated in an enclosed chamber. The toxicity increased with concentration from 11 to 176 μg/mL air, and with exposure times from 1 to 48 h. The LC50 values for A. polystachya and A. citriodora were 29.9 and 13.5 μg/mL air 24 h after treatment, respectively. To evaluate contact activity a glass-vial bioassay was used. The toxicity increased with concentration from 2.8 to 45 μg/cm2 and with exposure time from 1 to 48 h. The LC50 for A. polystachya was 3.4 μg/cm2 and for A. citriodora 8.1 μg/cm2. The repellency bioassay demonstrated that both oils were active at the highest concentration (2.6 and 5.3 μg/mL air) and neutral at 1.3 μg/mL air. These results show that the essential oils from Aloysia polystachya and A. citriodora could be applicable to the management of populations of Nezara viridula.