bluuebunny/crossref_metadata_2025 huggingface dataset:
Two New Sulfonoglycolipids from the Green Alga Codium dwarkense
Authors: Ali Liaqat , Al-Kharusi Lubna , Al-Harrasi Ahmed
Published: March 2019

Two new sulfonoglycosides named Codioside E (1) and Codioside F (2) have been isolated from the MeOH extract of the marine green alga Codium dwarkense collected from the coastal areas of the Gulf of Oman. The structures of these secondary metabolites were elucidated by combined analysis of 1D (1H- and 13C-) and 2D (H–C correlations; HSQC and HMBC) NMR spectroscopic and MS data.
A Convergent Total Synthesis of Balticolid
Authors: Srilatha Avuluri , Yadav Jhillu S. , Reddy Basi V. Subba
Published: March 2019

A convergent total synthesis of the 12 membered macrolide, Balticolid (1) is described, starting from readily available homoallylic alcohol and 1,3 propane diol. The synthetic strategy involves the construction of the 12-membered lactone.
Improvement Effects of Wasabi (Wasabia japonica) Leaves and Allyl Isothiocyanate on Stomach Lesions of Mongolian Gerbils Infected with Helicobacter pylori
Authors: Masuda Shuichi , Masuda Hideki , Shimamura Yuko , Sugiyama Chitose , Takabayashi Fumiyo
Published: March 2019

The relationship between Helicobacter pylori infection and gastric cancer associated with stomach lesions has been reported. Improvement of the adverse effects induced by H. pylori is required for human health. It has been reported that wasabi ( Wasabia japonica Matsum) leaves have various effects on bacteria and mammals. In this study, the effect was examined of wasabi leaf extract and allyl isothiocyanate (AIT), which is a main functional component of wasabi, on stomach lesions in Mongolian gerbils infected with H. pylori. After the gerbils infected with H. pylori were orally administrated with wasabi leaf extract and AIT for two weeks, colony forming units (CFU) of H. pylori, the degree of gastric mucosal erosion, and petechial hemorrhage in the stomachs of the gerbils were evaluated. Wasabi leaf extract and AIT exhibited a decreasing tendency of CFU in the stomachs. The degree of gastric mucosal erosion and petechial hemorrhage were significantly decreased by the intake of wasabi leaf extract and AIT. Wasabi leaf extract and AIT did not affect body weight, dietary intake, water intake, and the pH of the stomach. From these results, wasabi leaves and AIT may provide a natural remedy for stomach lesions induced by H. pylori.
Antiviral Activity of Aspalathus linearis against Human Influenza Virus
Authors: Rahmasari Ratika , Haruyama Takahiro , Charyasriwong Siriwan , Nishida Tomoki , Kobayashi Nobuyuki
Published: March 2019

Influenza A viruses are responsible for annual epidemics and occasional pandemics, which cause significant morbidity and mortality. The limited protection offered by influenza vaccination, and the emergence of drug-resistant influenza strains, highlight the urgent need for the development of novel anti-influenza drugs. However, the search for antiviral substances from the library of low molecular weight chemical compounds is limited. Thus, because of their natural diversity and accessibility, plants or plant-derived materials are rapidly becoming valuable sources for the discovery and development of new antiviral drugs. In this study, crude extracts of Aspalathus linearis, a plant reported to have anti-HIV activity, were evaluated in vitro for their activity against the influenza A virus. Of the extracts tested, an alkaline extract of Aspalathus linearis demonstrated the strongest inhibition against influenza A virus and could also inhibit different types of influenza viruses, including Oseltamivir-resistant influenza viruses A and B. Our time course of addition studies indicated that the alkaline extract of Aspalathus linearis exerts its antiviral effect predominantly during the late stages of the influenza virus replication process.
Methyl 3-(5-(prop-1-yn-1-yl)thiophen-2-yl)propanoate: A Rare Acetylene Derivative from Artemisia absinthium Root Essential Oil
Authors: Blagojević Polina D. , Pešić Marko S. , Radulović Niko S.
Published: March 2019

Methyl 3-(5-(prop-1-yn-1-yl)thiophen-2-yl)propanoate (1), biosynthetically and structurally related to dehydromatricaria ester, was isolated from the root essential oil of Artemisia absinthium L. (0.7% of the total oil). This is the second record of this compound and the very first one regarding it as an essential-oil constituent. In this paper, we give details regarding its isolation, structural elucidation and gas chromatographic properties (RI on DB-5 MS column: 1694). The NMR-based identification of the compound was corroborated by simulation of its 1H- and 13C-NMR spectra using a GIAO method (DFT level of theory). A tentative biosynthetic pathway, possibly leading to this compound, is also proposed.
Chemical Composition and Anti-inflammatory Activity of Algerian Thymus vulgaris Essential Oil
Authors: Abdelli Wafae , Bahri Fouad , Romane Abderrahmane , Höferl Martina , Wanner Juergen , Schmidt Erich , Jirovetz Leopold
Published: March 2019

This work aims to elucidate the chemical composition of two essential oil (EO) samples obtained from the leaves of Thymus vulgaris L. ( Lamiaceae) collected in two regions of Northwestern Algeria (Tlemcen and Mostaganem) and to assess their in vivo acute toxicity and anti-inflammatory activity. Sixty-six compounds could be identified by means of simultaneous GC-FID and GC-MS, accounting for 99.3% of total thyme oil of Mostaganem (EO.TM) and 99.0% of Tlemcen (EO.TT). In both samples, thymol was the major component, amounting to 59.5% (EO.TM) and 67.3% (EO.TT) of the total oil. EO.TT proved to be acutely toxic to mice at a dose of 4500 mg/kg p.o., whereas EO.TM did not show signs of acute toxicity, even at the highest dose tested (5000 mg/kg p.o.). Both EO samples were proven to possess anti-inflammatory activities, significantly reducing carrageenan-induced paw edema in mice (after 6 hours at a dose of 400 mg/kg p.o) at 58.4% for EO.TT and 50.4% for EO.TM, respectively. In conclusion, it could be demonstrated that EOs of T. vulgaris exhibit a considerable in vivo anti-inflammatory activity at non-toxic doses.
Coriander (Coriandrum sativum) Essential Oil: Effect on Multidrug Resistant Uropathogenic Escherichia coli
Authors: Scazzocchio Francesca , Mondì Lorenzo , Ammendolia Maria Grazia , Goldoni Paola , Comanducci Antonella , Marazzato Massimiliano , Conte Maria Pia , Rinaldi Federica , Crestoni Maria Elisa , Fraschetti Caterina , Longhi Catia
Published: March 2019

Coriander ( Coriandrum sativum L., Apiaceae) is known for its antimicrobial activity and the aim of this study was to investigate the effect of its essential oil (CDO) against multidrug resistant uropathogenic Escherichia coli (UPEC). CDO was able to inhibit the growth of UPEC strains and propidium iodide uptake, and electron microscopy examination suggested that bacterial structural modifications occurred. The presence of CDO reduced the MIC of gentamicin. E.coli adhesion efficiency on cell monolayers and abiotic surfaces was not affected by subMIC oil concentrations; furthermore, CDO showed cytotoxic activity towards the HEp-2 tumor cell line. These findings contribute to the knowledge about essential oils as sources of potential antimicrobial agents against uropathogenic E. coli and encourage further investigations.
Dietary Soy Isoflavone: A Mechanistic Insight
Authors: Chadha Renu , Bhalla Yashika , Jain Ankita , Chadha Kunal , Karan Maninder
Published: March 2019

Soy, a major component of the diet for centuries contains the largest concentration of isoflavones, a class of phytoestrogens. A variety of health benefits are associated with the consumption of soy primarily because of the isoflavones genistein, daidzein, and glycitein with a potential protective effect against a number of chronic diseases. Owing to the pharmaceutical and nutraceutical properties allied with isoflavonoids and their use in functional foods, there is a growing interest in these compounds. This review throws light on the chemistry, and significant pharmacological and biopharmaceutical aspects of soy isoflavones. This article critically describes the mechanisms of action, infers conclusions and shows opportunity for future research.
Distribution and Diversity of Usage of the Amaryllidaceae in the Traditional Remediation of Infectious Diseases
Authors: Nair Jerald J. , van Staden Johannes , Bonnet Susanna L. , Wilhelm Anke
Published: March 2019

Globalization and multidrug resistance are amongst the factors implicated in the resurgence of infectious diseases in recent years. This has fostered a compelling need in drug discovery to replace (or supplement) existing schedules. The floral biodiversity has been identified as a viable resource platform due to its inimitable chemical characteristics as well as the presence of numerous of its members in traditional medicinal approaches towards these diseases. Whilst the plant family Amaryllidaceae is conventionally associated with cancer and motor-neuron disease therapies, this survey shows that it has a significant presence in the remediation of infections and infection-related ailments. This verifiable indigenous knowledge could amplify efforts towards the identification of the active chemical constituents.
Vibrational Circular Dichroism: Recent Advances for the Assignment of the Absolute Configuration of Natural Products
Authors: Burgueño-Tapia Eleuterio , Joseph-Nathan Pedro
Published: March 2019

Vibrational circular dichroism (VCD) emerged during the last decade as a reliable tool for the absolute configuration (AC) determination of organic compounds. The principles, instrumentation, and methodology applied prior to early 2013 were recently reviewed by us. Since VCD is a very dynamic field, the aim of this review is to update VCD advances for the AC assignment of terpenoids, aromatic compounds, alkaloids, and other natural products for the 2013–2014 period, when VCD was applied to the AC assignment of some 70 natural products. In addition, although discovered in 2012, a brief introduction to the VCD exciton coupling approach and its applications in natural products AC assignment is presented.
Antioxidant Activity of Carvone and Derivatives against Superoxide Ion
Authors: Pombal Sofia , Hernández Yaiza , Diez David , Mondolis Eily , Mero Aldahir , Morán-Pinzón Juan , Guerrero Estela I. , Rodilla Jesús M.
Published: March 2019

Carvone has corroborated its versatility as starting material for building blocks synthesis in organic chemistry, being achieved a new chiral lactone. It has been done a study on the antioxidant activity against superoxide of carvone and a chloro derivative that show the potent activity of the natural product ( R)-carvone, 1.
Studies in Cyclization of Aromatic Epoxy-acyclicpolyprenes: Lewis Superacids and Titanocene Chloride
Authors: Castillo Alexis , del Moral José Fco Quilez , Barrero Alejandro F.
Published: March 2019

Two catalytic cascade cyclization methods (radical and cationic) to obtain aromatic polycyclic diterpenes hydroxylated at C3 starting from aromatic epoxypolyprenes were developed. The catalytic use of the Lewis superacid bismuth triflate produces a good yield of cyclized 2 from epoxypolyprene 3. This research may well direct future efforts to the synthesis of bioactive natural products.
Structure-Dependent Cytotoxic Effects of Eremophilanolide Sesquiterpenes
Authors: Agulló-Ortuño M. Teresa , Díaz Carmen E. , González-Coloma Azucena , Reina Matías
Published: March 2019

The aim of this research was to determine the cytotoxic action of sixteen structurally-related eremophilane-type sesquiterpenes, isolated from several species of Senecio, against a panel of cancer cell lines. The cytotoxic activities were evaluated by WST-1 test and the IC50 values calculated. The investigated compounds exerted dose-dependent cytotoxic actions against selected cancer cell lines and no-tumoral HS5 cell line. The comparative structure-activity relationships demonstrated the importance of C-1, C-6, and C-8 substituents in the molecule. Our results show that eremophilane-type sesquiterpenes may represent an important source of novel potential antitumor agents due to their pronounced cytotoxic actions towards malignant cells.
Highly Functionalized Ring B Labdane Synthesis as Key Intermediate in the Route to Forskolin
Authors: Tobal Ignacio E. , Castañeda Lourdes , Roncero Alejandro M. , Moro Rosalina F. , Diez David , Marcos Isidro S.
Published: March 2019

Sclareol has been employed as starting material for the synthesis of several advanced intermediates towards the synthesis of highly ring B oxygenated labdanes. Dinorlabdanes 6,7,8,9-tetraoxygenated with 6,7-dioxygenated functionalities with α- cis or β- cis dispositions, have been prepared and can be used for forskolin or analogues synthesis.
Optimization of the Number of Considered Conformers for the Absolute Configuration Determination of Catechin and Epicatechin Peracetates by VCD
Authors: Burgueño-Tapia Eleuterio , Sánchez-Castellanos Mariano , Joseph-Nathan Pedro
Published: March 2019

Epimeric catechin and epicatechin peracetates offer the possibility to explore the number of conformers needed for the absolute configuration determination without affecting the reliability of the assignment. Comparisons between experimental and DFT B3PW91/DGDZVP calculated curves showed that, in molecules where the conformational flexibility generates a large number of conformers, it is possible to significantly reduce the number of conformers needed to generate VCD results that provide secure absolute configuration assignment.
The Dimerization of Precocene I
Authors: Fraga Braulio M. , Cabrera Inmaculada
Published: March 2019

In an earlier work we reported that treatment of precocene I with Brönsted and Lewis acids produces its oligomerization, giving dimers, trimers, tetramers, etc. Now, in this article we show that bromination of precocene I with phenyltrimethylammonium tribromide (PTT) blocks its oligomerization giving a dibromo-dimer, which was reduced with tri- n-butyl tin hydride affording the same dimer obtained in the reactions with acid, thus avoiding the oligomerization. Additionally, the oxidations of precocene I with Jones reagent afforded the corresponding 3-hydroxy-4-chromanone, 3,4-chromandione, 3,4-diacid, and two dimers.
Synthesis and Biological Evaluation of Imines Structurally Related to Resveratrol as Dual Inhibitors of VEGF Protein Secretion and hTERT Gene Expression1
Authors: Martí-Centelles Rosa , Murga Juan , Falomir Eva , Carda Miguel , Marco J. Alberto
Published: March 2019

A group of 28 N-benzylidene aniline derivatives structurally related to the natural stilbene resveratrol has been prepared through condensation of anilines with the corresponding aldehydes. The ability of these imines to inhibit proliferation of two tumor cell lines (HT-29 and MCF-7) and one non-tumor cell line (HEK-293) was first determined. Subsequently, we determined the ability of some of the most cytotoxic compounds to inhibit the secretion of the VEGF-A factor in HT-29 cells and to downregulate the expression of the VEGF and hTERT genes, the latter one being involved in the activation of telomerase.
Nematicidal Activity of the Essential Oil of Three Varieties of Tagetes minuta from Argentina
Authors: Massuh Yamile , Cruz-Estrada Angel , González-Coloma Azucena , Ojeda Marta S. , Zygadlo Julio A. , Andrés Maria Fe
Published: March 2019

Essential oils composition of three Tagetes minuta varieties and a wild population (WP) from Argentina and their in vitro and in vivo nematicidal activity against root-knot nematode, Meloidogyne javanica, are described. All T. minuta EOs tested were very active against nematode juveniles (J2), but the strongest nematicidal effects were exhibited by the TmV3 variety oil, characterized by a high content of ( E)-ocimenone. High nematode egg hatching suppression (> 90%) was induced by TmV3 EO after five days of incubation. In vivo tests on tomato seedlings showed a significant reduction of infection rate of M. javanica J2 treated with TmV3 and WP oils at sub lethal dose. Therefore, EOs from chemically stable new varieties of T. minuta could be environmentally friendly nematicidal agents.
Trypanocidal Effects of Essential Oils from Selected Medicinal Plants. Synergy among the Main Components
Authors: Guardo Nuria I. , Sainz Paula , González-Coloma Azucena , Burillo Jesús , Martínez-Díaz Rafael A.
Published: March 2019

Fourteen essential oils (EOs) from selected live germplasm of medicinal plants have been tested for their antitrypanosomal and cytotoxic activity. These plants have been domesticated and maintained under experimental cultivation. Their EOs were tested on epimastigote forms of Trypanosoma cruzi strain Y and human lung fibroblasts LC5 cell line, along with the major components of the active oils, both separately and in binary combinations. Mentha rotundifolia, Thymus zygis, T. vulgaris and Hyssopus officinalis were the most active EOs against T. cruzi. Among the main components of these EOs (1-8-cineole, thymol, p-cymene, piperitenone oxide, β-pinene, γ-terpinene, carvacrol and linalool), the most active against the parasite and less toxic to human cells was thymol. In general, the activity of the main components did not exceed that of their origin EO, and the study of the activity of these compounds in combination indicates the existence of antagonistic and synergistic effects depending on the concentration tested.
Ring Rearrangement Metathesis in 7-Oxabicyclo[2.2.1]heptene (7-Oxanorbornene) Derivatives. Some Applications in Natural Product Chemistry
Authors: Roscales Silvia , Plumet Joaquín
Published: March 2019

Metathesis reactions is firmly established as a valuable synthetic tool in organic chemistry, clearly comparable with the venerable Diels-Alder and Wittig reactions and, more recently, with the metal-catalyzed cross-coupling reactions. Metathesis reactions can be considered as a fascinating synthetic methodology, allowing different variants regarding substrate (alkene and alkyne metathesis) and type of metathetical reactions. On the other hand, tandem metathesis reactions such Ring Rearrangement Metathesis (RRM) and the coupling of metathesis reaction with other reactions of alkenes such as Diels-Alder or Heck reactions, makes metathesis one of the most powerful and reliable synthetic procedure.

In particular, Ring-Rearrangement Metathesis (RRM) refers to the combination of several metathesis transformations into a domino process such as ring-opening metathesis (ROM)/ring-closing metathesis (RCM) and ROM-cross metathesis (CM) in a one-pot operation. RRM delivers complex frameworks that are difficult to assemble by conventional methods constitutingan atom economic process. RRM is applicable to mono- and polycyclic systems of varying ring sizes such as cyclopropene, cyclobutene, cyclopentene, cyclohexene, pyran systems, bicyclo[2.2.1]heptene derivatives, bicyclo[2.2.2]octene derivatives, bicyclo[3.2.1]octene derivatives and bicyclo[3.2.1]octene derivatives.

In this review our attention has focused on the RRM reactions in 7-oxabicyclo[2.2.1]heptene derivatives and on their application in the synthesis of natural products or significant subunits of them.
Study of Anti-Tuberculosis Activity Behaviour of Natural Kaurane and Trachylobane Diterpenes Compared with Structural Properties Obtained by Theoretical Calculations
Authors: Soares Ana C. F. , Cabral Mirela M. W. , Martins Carlos H. G. , Ferreira Alexsandro E. , Bergamo Pedro A. S. , Omosa Leonida K. , Midiwo Jacob O. , Parreira Renato L. T. , Heleno Vladimir C. G.
Published: March 2019

A set of seven diterpenes, three kauranes and four trachylobanes, isolated from the African plant Psiadia punctulata were assayed against Mycobacterium tuberculosis and reached activity comparable with cycloserine, a second line drug used to treat tuberculosis (TB). Several structural properties of those diterpenes, such as lipophilicity, HOMO and LUMO energies, charge density, and intramolecular hydrogen bond (IHB) formation, were obtained by theoretical calculations and compared with their activities. Peculiar correlations were observed, especially between activity, lipophilicity and IHB formation.
Canthin-6-one Isolated from Brucea javanica Root Blocks Cancer Cells in the G2/M phase and Synergizes with Cisplatin
Authors: Samat Norazwana , Ng Mei Fong , Lee Hui Mei , Ling Sui Kiong , Tan Pei Jean , Patel Vyomesh
Published: March 2019

Poor prognosis of most cancer patients is in part, due to limited therapeutic options. Furthermore, as chemotherapy remains the standard-of-care for several cancers, partial or lack of response remains a concern and compounding this are the adverse side effects of the treatment that severely impacts the quality of life and survival. In pursuit of improving treatment options, we have opted to investigate the unique chemical skeleton of natural compounds as anticancer therapies. In this study, from an initial screen of 31 crude methanol extracts from ~15 plant species using HL60 cells, the root extract of Brucea javanica (L.) Merr indicated the presence of bioactive compounds. Subsequent bioassay-guided purification on the root extract yielded two alkaloids canthin-6-one (1) and bruceolline J (2), which were further investigated for their bioactivity in representative human cancer lines and normal phenotypic counterparts. MTT assay demonstrated ED50 values from 34.7–72.9 μM for 1 and 16.0–54.0 μM for 2 for the cancer cell lines panel. NP69 cells also demonstrated sensitivity to both compounds (9.3 μM and 4.5 μM). As amount of 2 isolated were limiting, we focused on 1 to further identify novel anticancer properties in PC3 and HeLa cancer lines. We observed at 30 μM, 1 induced a G2/M phase arrest coinciding with decreased cell proliferation. Furthermore, 1 was able to synergize the cytotoxic effect of cisplatin when used in combination, suggesting the potential of combination therapy for those less responsive lesions to standard chemotherapy.
Chemical Constituents of the Root of Angelica tenuissima and their Anti-allergic Inflammatory Activity
Authors: Choi Hyun Gyu , Je In-Gyu , Kim Geum Jin , Nam Joo-Won , Shim Sang Hee , Kim Sang-Hyun , Choi Hyukjae
Published: March 2019

A phthalide, levistolide A (1), and six coumarins, demethylsuberosin (2), fraxetin (3), (-)-marmesinin (4), 3'( S)- O-β-D-glucopyranosyl-3’,4'-dihydroxanthyletin (5), 3'( R)- O-β-D-glucopyranosyl-3’,4'-dihydroxanthyletin (6), and isopraeroside IV (7) were isolated from the methanolic extract of the roots of Angelica tenuissima Nakai. Their chemical structures were confirmed by comparing spectroscopic and reported data. All seven compounds were isolated for the first time from this plant source. The anti-allergic activities of compounds 1-7 were examined using human mast cells, and compounds 1-3 at 10 μM potently suppressed IL-6 expression and inhibited histamine release from human mast cells by more than 30%.
Antioxidant Activity and Chemical Composition of Essential Oils of some Aromatic and Medicinal Plants from Albania
Authors: Hodaj-Çeliku Entela , Tsiftsoglou Olga , Shuka Lulëzim , Abazi Sokol , Hadjipavlou-Litina Dimitra , Lazari Diamanto
Published: March 2019

The chemical compositions have been investigated of the volatile oils of nine populations of six species from Albania, namely Artemisia absinthium, Calamintha nepeta, Hypericum perforatum, Sideritis raeseri subsp. raeseri, Origanum vulgare subsp. hirtum from two wild populations, and Salvia officinalis (sage) from two wild and one cultivated population,. The essential oils were obtained by hydrodistillation and their analyses were performed by GC–MS. The major constituents were: A. absinthium: neryl isovalerate (19.5%), geranyl isobutanoate (16.4%) and carvacrol (8.8%); C. nepeta: pulegone (31.7%), spathulenol (20.0%) and isomenthone (12.7%); H. perforatum: caryophyllene oxide (31.0%), δ-selinene (10.5%) and carvacrol (10.4%); O. vulgare: carvacrol (81.0, 78.6%), γ-terpinene (5.5, 7.1%) and p-cymene (4.9, 4.1%) for O. vulgare originating from Tepelena and Vlora, respectively; S. raeseri: carvacrol (36.7%), caryophyllene oxide (17.8%), β-caryphyllene (8.7%), spathulenol (7.7%) and myrtenol (6.4%); S. officinalis: camphor (40.2, 47.8, 45.9%), α-thujone (19.2, 22.2, 13.7%), eucalyptol (5.4, 2.6, 6.0%), camphene (5.8, 6.1, 3.9, %), borneol (2.1, 2.9, 5.7%) and bornyl acetate (3.3, 1.4, 5.6%) for samples originating from Tepelena, Tirana and Vlora, respectively. The essential oils were also tested for their free radical scavenging activity using the following in vitro assays: i) interaction with the free stable radical of DPPH (1,1-diphenyl-2-picrylhydrazyl), and ii) inhibition of linoleic acid peroxidation with 2,2'-azobis-2-methyl-propanimidamide, dihydrochloride (AAPH). Finally, their inhibitory activity toward soybean lipoxygenase was evaluated, using linoleic acid as substrate. The essential oil of O. vulgare (OV-VL) presented the highest interaction with the stable radical DPPH (76.5%), followed by that of A. absinthium (54.7%). O. vulgare (OV-TP) and A. absinthium showed high anti-lipid peroxidation activity, 97.5% and 96.5%, respectively, higher than that of the reference compound trolox (73.0%). Only the tested sample of O. vulgare (OV-VL) significantly inhibited soybean lipoxygenase (54.2%).
Polysaccharides in Human Health Care
Authors: van Dam Jan E.G. , van den Broek Lambertus A.M. , Boeriu Carmen G.
Published: March 2019

Polysaccharides are abundant natural polymers found in plants, animals and microorganisms with exceptional properties and essential roles to sustain life. They are well known for their high nutritive value and the positive effects on our immune and digestive functions and detoxification system. The knowledge and recognition of the important role they play for promoting and maintaining human health and wellbeing is continuously increasing. This review describes some important polysaccharides (e.g. mucilages and gums, glycosamine glycans and chitin/chitosan) and their medical, cosmetic and pharmaceutical applications, with emphasis on the relationship between structure and function. Next, the use of polysaccharides as nutraceuticals and vaccines is discussed in more detail. An analysis of the trends and challenges in polysaccharide research concludes the paper.
Exploitation of Old Wheat Properties for Prevention of Human Disease
Authors: Jirillo Emilio , Carone Tommaso , Toffanin Renato
Published: March 2019

Cereals occupy an important place in the Mediterranean diet pyramid and carbohydrates derived from whole grains seem to exert a beneficial role. In this context, some ancient wheat varieties such as khorasan wheat ( Triticum turgidum ssp. turanicum) may offer unique nutritional and functional properties to prevent human disease. The current paper reviews specific features of dietary carbohydrates focussing the attention on khorasan wheat and its major potential health benefits once regularly introduced in the diet.
Starch Polysaccharides in the Human Diet: Effect of the Different Source and Processing on its Absorption
Authors: Perin Danilo , Murano Erminio
Published: March 2019

Starch is the main source of carbohydrates in human diet. It is widely used in food processing and non-food industrial applications. The effects on starch digestion and absorption in humans are reviewed in relation to the starch composition, sources, plant genetic variation, food processing and cooking. The impact of food industrial processing and starch modification on the digestibility of starch containing foods and on gut microbiota are discussed. Considering that the resistant starch (RS) fraction escaped from the small intestine is fermented in large intestine, all the variables that influence starch digestibility and absorption must be taken into account when discussing about healthy properties of fibers. Future trends in food industries are aimed to increase the RS fraction in processed foods in order to improve nutritional quality as well as to clarify the influence of RS3 and RS4 on gut microbiota.
A New Monoterpene Isolated from Nigella sativa Essential Oil
Authors: Benharref Ahmed , Fdil Rabia , Hanbali Fadwa El , Zeroual Abdellah , Dakir Mohamed , Mazoir Noureddine
Published: March 2019

A new monoterpene 2-allyl-1,4-dihydroxy-5-methylbenzene 1 has been isolated from the essential oil of Nigella sativa seeds along with five known compounds including thymoquinone, carvacrol, dihydrothymoquinone, terpinen-4-ol and dithymoquinone. The structure of the new monoterpene 1 was elucidated using 1D and 2D NMR studies.
Synthesis and Cytotoxic Evaluation of Novel Ester Derivatives of Betulin with AZT, d4T, and 3TC
Authors: Anh Dang Thi Tuyet , Giang Le Nhat Thuy , Hien Nguyen Thi , Cuc Dinh Thi , Thanh Nguyen Ha , Tra Nguyen Thanh , Phuong Hoang Thi , Van Tuyen Nguyen , Van Kiem Phan
Published: March 2019

Novel ester derivatives of betulin with AZT, d4T, and 3TC were synthesized and assessed for antitumor activities against the KB and HepG2 human cancer cell lines in vitro by MTT assay. Some derivatives displayed high anticancer properties, with IC50 values between 1 and 21 μM on the two cancer cell lines.
Quantitation of Bacopaside I in Rat Biological Samples by LC-QTOF-MS/MS and Its Pharmacokinetic Application
Authors: Sookying Sontaya , Pekthong Dumrongsak , Oo-Puthinan Sarawut , Nuengchamnong Nitra , Ingkaninan Kornkanok
Published: March 2019

Bacopaside I is a triterpenoid saponin, a major compound in Bacopa monnieri, which exhibits several potentially useful clinical activities including memory enhancement. Accordingly, a sensitive liquid chromatography tandem mass spectrometric method was developed and validated to determine bacopaside I in rat serum, urine, and feces. Digitoxin was the internal standard. Simple protein precipitation was used in the sample preparation. The separation was performed using a C18 column with gradient elution, and electrospray ionization in the negative ion mode was selected. The method proved to be precise (both intra- and inter-day CV <13.2% in serum, urine, and feces), accurate (intra- and inter-day recovery within 93.1–112.0 %), and selective, while providing high sensitivity (LLODs were 0.13 ng for rat serum and urine and 0.25 ng for rat feces and LLOQs were 0.13 ng for rat serum and urine and 0.25 ng for rat feces). We successfully applied this method to the pharmacokinetics of bacopaside I in rats. This report describes mean residence time and elimination of bacopaside I.
A Novel Steroid Derivative and a New Steroidal Saponin from Endophytic Fungus Xylaria sp
Authors: Li Wei , Yang Xue-Qiong , Yang Ya-Bin , Zhao Li-Xing , Zhou Qing-Yan , Zhang Zhuo-Xi , Zhou Hao , Hu Ming , Ruan Bao-Hui , Ding Zhong-Tao
Published: March 2019

Two new steroids, (24 R)-22, 23-dihydroxy-ergosta-4,6,8(14)-trien-3-one 23-β-D-glucopyranoside (1), and xylarester (2), together with 16 known compounds were isolated from the extract of endophytic Xylaria sp. solid culture. Their structures were elucidated by spectroscopic methods. Compound 2 has an unprecedent ergosta skeleton with a six-membered lactonic group in A ring. The X-ray single crystal diffraction data of 4,7-dihydroxy-13-tetradeca-2,5,8-trienolide (4) were also reported for the first time. The antibacterial, anti-acetylcholinesterase, nitric oxide inhibition and cytotoxic activities of 1–3 were investigated. Compound 1 showed cytotoxicity to MCF-7 with the ratio of inhibition at 72 % for a concentration at 40 μM.
Isoprenylated Phenolics from Roots of Artocarpus heterophyllus
Authors: Zhai Xiao Xiao , Xiao Chuan Yun , Jiang Wei , Chen Yun Long , Ding Yuan Qing , Ren Gang
Published: March 2019

Thirteen compounds were isolated from Artocarpus heterophyllus, including one new di-isoprenylated stilbene, (±)-artoheterin A (1), and twelve known isoprenylated phenolics, artocarbene (2), 3′,5′,2,4-tetrahydroxy-4′-(3-methyl-2-butenyl) stilbene (3), cudrastilbene (4), 3-(3-methyl-2-butenyl) luteolin (5), 5,7,2′,4′-tetrahydroxy-6-(3-methyl-2-butenyl) flavone (6), 6-(3-methyl-2-butenyl) apigenin (7), artochamin B (8), 5′-hydroxycudraflavone A (9), artonins A and B (10–11), heterophyllin (12), and 8-(3-methyl-2-butenyl)-6,7-dihydroxycoumarin (13). The structures of these compounds were identified by spectroscopic methods. All isolated compounds were screened for their inhibitory abilities against cathepsin K (CatK). Of them, compounds 1–4 and 8–13 were found to have suppression capabilities against CatK with IC50 values ranging from 1.9 to 73.7 μM.
Inhibitory Effect of Zingerone on Secretory Group IIA Phospholipase A2
Authors: Lee In-Chul , Kim Dae Yong , Bae Jong-Sup
Published: March 2019

The expression of secretory group IIA phospholipase A2 (sPLA2-IIA) has been shown to be elevated in various inflammatory diseases, and lipopolysaccharide (LPS) up-regulates the expression of sPLA2-IIA in human umbilical vein endothelial cells (HUVECs). Zingerone (ZGR), a phenolic alkanone isolated from ginger, has been reported to have various pharmacological activities. Here, we examined the effects of ZRG on the expression and activity of sPLA2-IIA in LPS-activated HUVECs and in mouse models of endotoxemia and sepsis. Treatment of cells or mice with ZRG inhibited LPS-induced expression and activity of sPLA2-IIA. In addition, ZRG suppressed LPS-mediated activation of cytosolic phospholipase A2 (cPLA2) and extracellular signal-regulated kinase (ERK) 1/2. These results suggest that ZRG inhibits LPS-mediated activation of sPLA2-IIA expression by suppressing cPLA2 and ERK 1/2.
Production of Schisandrin A and Schisandrin B from Callus and Suspension Cell Cultures of Schisandra chinensis
Authors: Zhou Yong-Qiang , Li Tian-Cong , Cheng Yu-Peng
Published: March 2019

For establishing the fermentation system of synthetic schizandrin A and schizandrin B, culture conditions of the Schisandra chinensis callus and the suspension cell were studied in this paper. The friable calluses of Schisandra chinensis (Turcz.) Baill. were induced from hypocotyls in Murashige-Skoog (MS) solidified medium supplemented with hormone 6-benzylaminopurine (6-BA) and 2,4-Dichlorophenoxyacetic butyl acetate (2,4-D) in different concentrations, and suspension cells initiated from friable callus were cultured in MS liquid medium with various concentrations and combinations of 6-BA, 2,4-D and kinetin (KT). The optimal culture condition for callus inducement was found to be MS solidified medium with 6-BA 1.0 mg/l and 2,4-D 0.3 mg/l and the optimal condition for suspension cells was MS liquid medium with 6-BA 1.0 mg/l, 2,4-D 0.2 mg/l and KT 0.5 mg/l. UPLC/Q-TOF-MS method was used for accurate identification of schisandrin A and schisandrin B in the seeds, callus and suspension cells of S. chinensis. And HPLC analytical method was used successfully for identification and quantification of these metabolites in cultures of S. chinensis. As a result, schisandrin A was obtained 0.251 mg/g, 0.118 mg/g and 0.115 mg/g from seeds, callus and suspension cells and schisandrin B was 0.142 mg/g, 0.086 mg/g and 0.05 mg/g from seeds, callus and suspension cells, respectively. Our datas indicate that callus and suspension cells had capability as seeds of S. chinensis for schisandrin A and schisandrin B synthesizing and can be used as potential sources of these biologically active lignans.
N-Didehydrotyrosine identified from the Northeastern Atlantic marine sponge Hymeniacidon perlevis after Chemical Screening
Authors: Mahajan Nipun , Calabro Kevin , Morrow Christine , Thomas Olivier P.
Published: March 2019

Chemical screening of bio-resources coupled with dereplication is an efficient method to discover new chemical scaffolds. In this study, twenty Irish marine sponges were subjected to rapid SPE fractionation followed by their chemical screening based on 1H NMR and HPLC-DAD-ELSD profiles. A fraction obtained from the sponge Hymeniacidon perlevis had the most promising profile, and further purifications and spectroscopic investigations including HRMS, 1D and 2D NMR led to the identification of a new metabolite N-didehydrotyrosine (1) and the known compound N9-methyladenine (2).
Investigation of Echinacea purpurea Root Proteins with Hemagglutinating Activity
Authors: Balciunaite Gabriele , Dam Svend , Pesliakas Henrikas , Zvirblis Gintautas , Mistiniene Edita , Ragazinskiene Ona , Pampariene Ina , Zymantiene Judita , Baniulis Danas , Savickiene Nijole
Published: March 2019

Proteins were extracted and fractionated from Echinacea purpurea L. (Moench) (purple coneflower) roots, to evaluate their hemagglutinating activity. Our data suggests that the ~ 25 kDa glycosylated protein is responsible for the hemagglutinating activity and might be worth for its investigation for other biological activities.
One-Step Synthesis of 2-Alkenecarbodithioate Esters from Substituted Propargyl Ethers, and Their Conversion into Isothiazole Ring through a [4+1] Type Oxidative Ring Closure
Authors: Shimada Kazuaki , Ishikawa Fumiya , Alam Md. Ashraful , Korenaga Toshinobu
Published: March 2019

Treatment of substituted propargyl methyl ethers with a base and elemental sulfur in the presence of a thiolate ion afforded 2-alkenecarbodithioate esters in good yields. The reaction is assumed to proceed through a pathway involving in situ generation of propadienethione intermediates. Further conversion of 2-alkenecarbodithioate esters into 2,3-dihydroisothiazoles were efficiently performed by treating with chloramine-T through a [4+1] type oxidative ring closure via thiocarbonyl S-tosylimides.
Prospection of Effects of Guava Leaves Infusion: Antigenotoxic Action and Enzymatic Inhibition
Authors: Cesar Pedro H S , Trento Marcus V C , Oliveira Daniela A , Simão Anderson A , Vieira Larissa F A , Marcussi Silvana
Published: March 2019

Several forms of Psidium guajava L. (guava) leaf preparations have been widely used for prevention and treatment of illnesses. However, researches about the protective action of guava's natural products on the genetic material of animal cells is scarce. Accordingly, the aim of this study was to evaluate the antigenotoxic potential of infusions of guava leaves from three cultivars (Pedro Sato, Paluma and Roxa) against DNA damage induced by Doxorubicin (DXR) in human leukocytes, and their effects on enzymatic inhibition. To assess the antigenotoxic potential of these infusions, a comet assay (single cell electrophoresis) was conducted. In addition, their inhibitory potential on phospholipase and hemolytic activities was assessed. The evaluated infusion volumes (25, 50 and 300μL) presented inhibitions around 75% of the DXR-induced damage frequencies. Their protective effect was demonstrated by arbitrary unit calculations, with values between 52.51 and 66.60 for all treatments, 250.51 for positive control (DXR), and 45.49 for phosphate buffered saline (negative control). The infusions significantly inhibited phospholipase and hemolytic activities induced by Bothrops alternatus and B. moojeni venoms, with inhibitions ≥ 50% for both activities induced by B. alternatus. The infusions of P. guajava from the cultivars analyzed present antigenotoxic potential, but also demonstrate potential of enzymatic inhibition on A2 phospholipases and proteases.
Bark Essential Oils of Zanthoxylum clava-herculis and Ptelea trifoliata: Enantiomeric Distribution of Monoterpenoids
Authors: Steinberg Kelly Marie , Satyal Prabodh , Setzer William N.
Published: March 2019

The bark essential oils of Zanthoxylum clava-herculis and Ptelea trifoliata (Rutaceae) were obtained by hydrodistillation and analyzed by both gas chromatography as well as chiral gas chromatography coupled with mass spectrometry. Z. clava-herculis bark oil was dominated by sabinene [47.0%, 95% (–)-sabinene], limonene [18.7%, 99% (+)-limonene], and terpinen-4-ol [12.9%, 75% (–)-terpinen-4-ol]. The major components in P. trifoliata bark oil were limonene [15.2%, 99% (–)-limonene], sabinene [6.9%, 79% (–)-sabinene], and β-phellandrene [6.2%, 87% (–)-β-phellandrene].
Chemical Composition and Antibacterial Activity of Melaleuca bracteata Essential Oil from India: A Natural Source of Methyl Eugenol
Authors: Goswami Prakash , Verma Sajendra K. , Chauhan Amit , Venkatesha KT , Verma Ram S. , Singh Ved R. , Darokar Mahendra P. , Chanotiya Chandan S. , Padalia Rajendra C.
Published: March 2019

The aim of this study was to investigate the chemical composition and antibacterial activity of the essential oil of Melaleuca bracteata F. Muell from India. The hydrodistilled essential oils of M. bracteata in spring, summer, rainy, autumn and winter seasons were analyzed using GC-FID and GC-MS. Altogether, 25 constituents, comprising 97.3–99.7% of the total oil were identified with methyl eugenol (87.2–89.5%), ( E)-methyl cinnamate (2.8–5.4%), methyl chavicol (0.2–0.5%), and elemicin (0.2–0.4%) as major constituents. The antibacterial efficacy of the essential oil was evaluated against nine pathogenic bacterial strains. Zone of inhibition and MIC of the essential oil ranged from 5–10 mm and 500–1000 μg/mL against the tested pathogens, respectively. Results showed that essential oil of M. bracteata from Indian origin possessed good activity against Salmonella typhimurium, Staphylococcus epidermidis, and moderate activity against Bacillus subtilis, Staphylococcus aureus, Klebsiella pneumonia, and Streptococcus mutans. Results of the present seasonal variation study clearly indicated that M. bracteata grown in foothills of Uttarakhand, India could be classified as seasonally stable ‘methyl eugenol’ chemotype (>85.0%), hence may be considered as a novel natural resource for methyl eugenol rich essential oil for flavor, fragrance and pharmaceutical applications.
Chemical Composition, Antimicrobial, and Cytotoxic Activities of the Essential Oil of Otostegia fruticosa subsp. schimperi from Yemen
Authors: Ali Nasser A. Awadh , Alhamzy Ebtesam Hasan , Chhetri Bhuwan K. , Dosoky Noura S. , Setzer William N.
Published: March 2019

The leaf essential oil of Otostegia fruticosa subsp. schimperi (Lamiaceae) was obtained by hydrodistillation and analyzed by gas chromatography – mass spectrometry (GC-MS). The major components in the leaf oil were τ-cadinol (9.3%), β-caryophyllene (8.8%), and bornyl formate (5.2%) as well as two unidentified diterpenoids (12.7% and 9.4%, respectively). The leaf oil was screened for antibacterial ( Bacillus cereus, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa), antifungal ( Aspergillus niger, Candida albicans, and Botrytis cinerea), and cytotoxic (MCF-7 and MDA-MB-231) activity. The oil did not show antimicrobial or antifungal activity, but it showed very good cytotoxicity against MCF-7 (IC50 = 55.1 μg/mL) and MDA-MB-231 (IC50 = 70.3 μg/mL) cell lines.
Insecticidal Effects of Essential Oils against Nymphal and Adult Stage of Ricania simulans (Hemiptera: Ricanidae)
Authors: Gokturk Temel , Kordali Saban , Bozhuyuk Ayse Usanmaz
Published: March 2019

Ricania simulans (Walker, 1851) (Hemiptera: Ricanidae) nymphal and adult stages prefer all agricultural plants, bushes and young trees as their hosts, and feed on the juice of these plants and damage them areas in the Eastern Black Sea coastline since 2006. Nymphs have 5 nymphal stages and emerge in the end of May. The adults emerge early July and start to lay their eggs in early August, overwinter egg stage and gives one generation in a year. Nymphal and adult stages of R. simulans were tested against the toxicities of essential oils obtained from six plant species ( Achillea biebersteinii Afan. (Asteraceae), Origanum onites L. (Lamiaceae), Rosmarinus officinalis L. (Lamiaceae), Salvia pratensis L., (Lamiaceae), Satureja hortensis L. (Lamiaceae) and Tanacetum balsamita L. (Asteraceae)). In comparison with the control group (Ethanol+ Sterile water mix), six different plant essential oils showed an insecticidal effect against the nymphal and adult stage of R. simulans, while Neemazal was used as positive control group. It was shown that mortality of the nymphs of R. simulans increased significantly after the treatment with essential oils (P≤0.05). The essential oils were dissolved in DMSO water solution (Ethanol+ Sterile water mix), and were sprayed to adults and nymphs at 10, 15 and 20 μL/petri doses respectively. However, the mortality increased with the increment of exposure time. After an exposure of 96 h at the concentration of 20 μL/petri dish, mortality rates of R. simulans nymphal and adult stages were reported as 42.5–74.1% and 23.3–50.8%, respectively. At the end of 24 hours, the doses of 10, 15, 20 μL/petri were reported to be the most effective in 8.33% mortality of essential oil R. officinalis R. simulans nymphal stage. Similarly, 26.6, 47.5, 74.1% mortality rates was seen after 48, 72 and 96 h with the application of volatile oil of R. officinalis respectively. Positive control (Neemazal) have highest mortality rates for nymphs (98.7%) and adults (70.0%).
Aroma Profile and Essential Oil Composition of Helichrysum species
Authors: Reidel Rose Vanessa Bandeira , Cioni Pier Luigi , Ruffoni Barbara , Cervelli Claudio , Pistelli Luisa
Published: March 2019

Essential oils and volatile emission from leaves and flowers of three Helichrysum species ( H. arenarium, H. nudifolium, H. graveolens) were analysed by GC-MS and SPME analysis. A total of 112 components were identified in the EOs representing 92.3–99.9% of the whole oil composition, while 109 constituents were identified in the spontaneous volatile emission accounted for 78.7–98.8% of the total volatile organic compounds (VOCs). Sesquiterpenes represented the main class of constituents in the EOs of the majority studied species. β-caryophyllene was the key compound of H. arenarium and H. nudifolium leaves, even though ( E)-2-hexenal showed high percentage in H. arenarium leaves. H. graveolens EO showed a good amount of diterpenes (cembrene and beyerene), absent in the other species. SPME analyses were carried out for the first time to complete the chemotaxonomic investigation on the volatile organic constituents of these plants.
Biomedical Properties and Origins of Sesquiterpene Lactones, with a Focus on Dehydroleucodine
Authors: Abood Steven , Eichelbaum Steven , Mustafi Sushmita , Veisaga Maria-Luisa , López Luis A. , Barbieri Manuel
Published: March 2019

Dehydroleucodine, a sesquiterpene lactone, belongs to the terpenoid class of secondary metabolites. Dehydroleucodine and other Artemisia-derived phytochemicals evolved numerous biodefenses that were first co-opted for human pharmacological use by traditional cultures in the Middle East, Asia, Europe and the Americas. Later, these phytochemicals were modified through the use of medicinal chemical techniques to increase their potency. All sesquiterpene lactones contain an α-methylene-γ-lactone group, which confers thiol reactivity, which is responsible, in part, for their therapeutic effects. A wide range of therapeutic uses of sequiterpene lactones has been found, including anti-adipogenic, cytoprotective, anti-microbial, anti-viral, anti-fungal, anti-malarial and, anti-migraine effects. Dehydroleucodine significantly inhibits differentiation of murine preadipocytes and also significantly decreases the accumulation of lipid content by a dramatic down regulation of adipogenic-specific transcriptional factors PPARγ and C-EBPα. Dehydroleucodine also inhibits secretion of matrix metalloprotease-2 (MMP-2), which is a known protease involved in migration and invasion of B16 cells. In addition to these anti-adipogenic and anti-cancer effects, dehydroleucodine effectively neutralizes several bacterial species, including Bacillus cereus, Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Helicobacter pylori, methicillin resistant Staphylococcus aueus (MRSA) and S. epidermis (MRSE). The compound also inhibits the growth and secretion of several toxins of Pseudomonas aeruginosa, possesses gastro-protective qualities and possesses anti-parasitic properties against Trypanosoma cruzi, responsible for Chagas disease. Other sesquiterpene lactones, such as parthenolide, costunolide, and helanin, also possess significant therapeutic utility.