bluuebunny/crossref_metadata_2025 huggingface dataset:
Physicochemical Properties of Honey from Marche, Central Italy: Classification of Unifloral and Multifloral Honeys by Multivariate Analysis
Authors: Truzzi Cristina , Illuminati Silvia , Annibaldi Anna , Finale Carolina , Rossetti Monica , Scarponi Giuseppe
Published: March 2019

The purpose of this study was the physicochemical characterization and classification of Italian honey from Marche Region with a chemometric approach. A total of 135 honeys of different botanical origins [acacia ( Robinia pseudoacacia L.), chestnut ( Castanea sativa), coriander ( Coriandrum sativum L.), lime ( Tilia spp.), sunflower ( Helianthus annuus L.), Metcalfa honeydew and multifloral honey] were considered. The average results of electrical conductivity (0.14 – 1.45 mS cm−1), pH (3.89 – 5.42), free acidity (10.9 – 39.0 meqNaOH kg−1), lactones (2.4 – 4.5 meqNaOH kg−1), total acidity (14.5 – 40.9 meqNaOH kg−1), proline (229–665 mg kg−1) and 5-(hydroxy-methyl)-2-furaldehyde (0.6–3.9 mg kg−1) content show wide variability among the analysed honey types, with statistically significant differences between the different honey types. Pattern recognition methods such as principal component analysis and discriminant analysis were performed in order to find a relationship between variables and types of honey and to classify honey on the basis of its physicochemical properties. The variables of electrical conductivity, acidity (free, lactones), pH and proline content exhibited higher discriminant power and provided enough information for the classification and distinction of unifloral honey types, but not for the classification of multifloral honey (100% and 85% of samples correctly classified, respectively).
GC/MS Analysis of the Essential Oil of Leucas indica from India
Authors: Joshi Rajesh K.
Published: March 2019

The aim of the present study was to investigate and identify the essential oil constituents of Leucas indica (L.) R.Br. (Lamiaceae). The chemical composition of the hydro-distilled essential oil was obtained from the flowering aerial parts of L. indica for the first time. The oil was analyzed by gas chromatography equipped with flame ionization detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC/MS). Fifty-six compounds were identified, representing 99.1% of the total oil. The main constituents were β-caryophyllene (51.1%) and α-caryophyllene (10.2%). The oil was found to be rich in sesquiterpene hydrocarbons (71.8%).
Skin Regeneration Effect and Chemical Composition of Essential Oil from Artemisia montana
Authors: Yoon Mi-So , Won Kyung-Jong , Kim Do Yoon , Hwang Dae il , Yoon Seok Won , Kim Bokyung , Lee Hwan Myung
Published: March 2019

Artemisia montana Pampan (Compositae) (AMP) contains various compounds, including phenolic acids, alkaloids, and essential oil. It has been widely used in oriental medicine due to a variety of biological effects. However, the biological activity of the essential oil from AMP (AMPEO) on skin has not been investigated. In the present study, AMPEO was evaluated for its composition and its effect on cellular events (migration and proliferation) related to skin regeneration using normal human keratinocytes (HaCats). AMPEO, which was extracted by steam distillation, contained 42 components. AMPEO increased proliferation in HaCats in a dose-dependent manner (EC 50, 8.5 ng/mL) and did not affect migration. AMPEO also enhanced the phosphorylation of Akt and ERK 1/2 and induced the synthesis of type IV collagen, but not type I collagen in HaCats. In addition, AMPEO promoted wound closure in the dorsal side skin of rat tail. These results demonstrated that AMPEO extracted by steam distillation induced proliferation and synthesis of type IV collagen in human skin keratinocytes, and may thereby exert positive effects on skin regeneration and wound healing in human skin.
Chemical Composition and Antimicrobial Activity of the Essential Oils of Pinus peuce (Pinaceae) Growing Wild in R. Macedonia
Authors: Karapandzova Marija , Stefkov Gjose , Cvetkovikj Ivana , Trajkovska-Dokik Elena , Kaftandzieva Ana , Kulevanova Svetlana
Published: March 2019

The chemical composition and antimicrobial activity of the essential oils isolated from twigs with needles (T+N) and from twigs without needles (T-N) from wild Pinus peuce Griseb. (Pinaceae), from three different locations in R. Macedonia, were investigated. Essential oil yields of T+N ranged from 7.5 mL/kg to 12.5 mL/kg and for T-N from 13.8 mL/kg to 17.3 mL/kg. GC/FID/MS analysis of the essential oils revealed eighty-four components, representing 93.7–95.7% and 91.2–92.0% of the T+N and T-N oils, respectively. The major components in T+N and T-N oils were monoterpenes: α-pinene (23.8–39.9%, 21.2–23.3%), camphene (2.2–5.5%, 0.7–2.0%), β-pinene (10.1–17.1%, 8.2–16.4%), myrcene (1.2–1.41%, 1.6–2.5%), limonene+β-phellandrene (6.8–14.0%, 8.8–23.6%) and bornyl acetate (2.3–6.9%, 1.1–3.4%), followed by the sesquiterpenes: trans-( E)-caryophyllene (3.6–4.3%, 3.2–7.3%), germacrene D (7.1–9.5%, 5.0–10.3%) and δ-cadinene (2.1–3.1%, 3.3–4.2%, respectively). Antimicrobial screening of the essential oils was made by disk diffusion and broth dilution methods against 13 bacterial isolates of Gram-positive and Gram-negative bacteria and one strain of Candida albicans. T-N essential oils showed antimicrobial activity toward Streptococcus pneumoniae, Staphylococcus aureus, S. epidermidis and Candida albicans as well as Streptococcus agalactiae, Acinetobacter spp. and Haemophilus influenzae. The antimicrobial activity of T+N essential oils was greater, especially against Streptococcus agalactiae, S. pyogenes, Enterococcus and Candida albicans, followed by Haemophilus influenzae, Acinetobacter spp., Escherichia coli, Salmonella enteritidis, Staphylococcus aureus and S. epidermidis. Minimal inhibitory concentrations (MICs) of all tested essential oils ranged from 15–125 μL/mL. Summarizing the obtained results, the antimicrobial activity of Pinus peuce T+N and T-N essential oils collected from different localities in R. Macedonia varied considerably. These alterations in the antimicrobial activity can be attributed to the differences in the quantitative composition and percentage amounts of the components present in the respective essential oils, although it was evident that there were no differences in the qualitative composition of the essential oils, regardless of the locality of collection, or the type of plant material (T+N or T-N).
Nutrigenomics of Essential Oils and their Potential Domestic Use for Improving Health
Authors: Sánchez José Antonio Cayuela , Elamrani Abdelaziz
Published: March 2019

The use of essential oils as industrial food additives is notorious, like their medicinal properties. However, their use in household food spicing is for now limited. In this work, we have made a review to reveal the nutrigenomic actions exerted by their bioactive components, to promote awareness of their modulating gene expression ability and the potential that this implies. Also considered is how essential oils can be used as flavoring and seasoning after cooking and before consumption, such as diet components which can improve human health. Genetic mechanisms involved in the medicinal properties of essential oils for food use are identified from literature. These genetic mechanisms reveal nutrigenomic actions. Reviews on the medicinal properties of essential oils have been particularly considered. A wide diversity of nutrigenomic effects from essential oils useful potentially for food spicing is reviewed. General ideas are discussed about essential oils and their properties, such as anti-inflammatory, analgesic, immunomodulatory, anticancer, hepatoprotective, hypolipidemic, anti-diabetic, antioxidant, bone-reparation, anti-depressant and mitigatory for Alzheimer's disease. The essential oils for food use are potentially promoting health agents, and, therefore, worth using as flavoring and condiments. Becoming aware of the modulating gene expression actions from essential oils is important for understanding their potential for use in household dishes as spices to improve health.
Biotechnological Valorization of Pectinolytics and Their Industrial Applications: A Review
Authors: Irshad Muhammad , Asgher Muhammad , Anwar Zahid , Ahmad Aftab
Published: March 2019

In the last several years, in serious consideration of the worldwide economic and environmental issues there has been an increasing research interest in the value of naturally occurring bio-sourced materials. Agro-industrial based biomass comprised of pectin is an inexpensive, renewable, abundant natural resource that could be utilized for large-scale and cost-effective production of natural products i.e., pectinolytics. Pectinolytics are one of the most widely distributed enzymes in bacteria, fungi and plants. From ancient times to date, many methods have been introduced to improve the optimization of pectinolytics to obtain high yields of maximal purity. To expand the range of natural bio-resources the rapidly evolving tools of biotechnology can lower the conversion costs and also enhance target yield of the product of interest. This green biotechnology presents a promising approach to convert most of the agricultural materials into a value-added product with multiple applications. Major advances have already been achieved in recent years in order to obtain high levels of purity with optimal yields. The present review begins with an overview of pectinolytics and their physico-chemical features, and their specific role with classification based on pectic materials. Information is also given on the culture influences and potential sources of pectinolytics, followed by a brief summary of various industrial and biotechnological applications and future considerations.
Anticancer Agents from Diverse Natural Sources
Authors: Khazir Jabeena , Riley Darren L. , Pilcher Lynne A. , De-Maayer Pieter , Mir Bilal Ahmad
Published: March 2019

This review attempts to portray the discovery and development of anticancer agents/drugs from diverse natural sources. Natural molecules from these natural sources including plants, microbes and marine organisms have been the basis of treatment of human diseases since the ancient times. Compounds derived from nature have been important sources of new drugs and also serve as templates for synthetic modification. Many successful anti-cancer drugs currently in use are naturally derived or their analogues and many more are under clinical trials. This review aims to highlight the invaluable role that natural products have played, and continue to play, in the discovery of anticancer agents.
Chemical Constituents of Tilia taquetii Leaves and their Inhibition of MMP-1 Expression and Elastase Activities
Authors: Kim Su Yeong , Kim Jung Eun , Bu Hee Jung , Hyun Chang-Gu , Lee Nam Ho
Published: March 2019

The ethanol extract of Tilia taquetii Schneider leaves was investigated for its anti-wrinkle properties and for the relevant chemical constituents. Phytochemical studies led to the identification of five known compounds, viz. phytol (1), isoquercitrin (2), oleanderolide (3), arjunolic acid (4) and maslinic acid (5) from the extract. Of these, compounds 4 and 5 inhibited the expression of matrix metalloproteinase-1 (MMP-1), an enzyme responsible for the breakdown of collagen fiber. Moreover, compound 5 showed inhibition activity on elastase, a protease enzyme capable of degrading elastin. These results suggest that the extract of T. taquetii containing the triterpenes 4 and 5 could be applied as anti-wrinkle ingredients in cosmetic preparations.
Phenolic Constituents of Erigeron floribundus (Asteraceae), a Cameroonian Medicinal Plant
Authors: Berto Chiara , Maggi Filippo , Nya Prosper C. Biapa , Pettena Anna , Boschiero Irene , Dall'Acqua Stefano
Published: March 2019

HPLC-MSn analysis of extracts of the Cameroonian medicinal plant Erigeron floribundus (Kunth) Sch. Bip. (Asteraceae) led to the identification of 40 different phenolic constituents. Four triterpene derivatives were isolated using semi-preparative HPLC and structures were elucidated on the basis of 1D and 2D NMR measurements. Compound 1, olean-3-oleil-12,18 diene, was a new natural product. Quali-quantitative measurements on the infusion obtained from dried aerial parts were also performed by HPLC-MSn and HPLC-DAD analysis showing that a cup of E. floribundus tea contains about 2.7 mg/mL of phenolics, with the caffeoyl quinic derivatives being the most abundant constituents.
C-24 Stereochemistry of Marine Sterols: (22E)-25,28-Dimethyl-stigmasta-5,22,28-trien-3β-ol and 25,28-Dimethylstigmasta-5,28-dien-3β-ol
Authors: Nojo Rie , Echigo Shizue , Hara Noriyuki , Fujimoto Yoshinori
Published: March 2019

The C-24 configurations of (22 E)-25,28-dimethylstigmasta-5,22,28-trien-3p-ol (1) and 25,28-dimethylstigmasta-5,28-dien-3β-ol (2), isolated from the sponge Topsentia ophiraphidites in our previous work, were determined to be both S, through the synthesis of stereodefined (24 S)- and (24 R)-epimers of 1 and 2 and comparison of the 1H and 13C NMR spectroscopic data. In addition, the C-24 configurations of the marine sterols having the same structures as 1 and 2 and their derivatives were also assigned for the first time by NMR comparison.
Antibacterial Compounds from Glycosmis puberula Twigs
Authors: Tantapakul Cholpisut , Sripisut Tawanun , Maneerat Wisanu , Ritthiwigrom Thunwadee , Laphookhieo Surat
Published: March 2019

The first phytochemical investigation of Glycosmis puberula twigs led to the isolation and identification of a new quinolone alkaloid, glycosmispuberulone (1), along with ten known compounds (2–11). The structures were elucidated by spectroscopic analyses and comparison with previously reported data. Their antibacterial activities against Gram-positive and Gram-negative bacteria were also evaluated.
Antimicrobial Activity of Extracts and Isoquinoline Alkaloids of Selected Papaveraceae Plants
Authors: Opletal Lubomír , Ločárek Miroslav , Fraňková Adéla , Chlebek Jakub , Šmíd2 Jakub , Hošt'álková Anna , Šafratová Marcela , Hulcová Daniela , Klouček Pavel , Rozkot Miroslav , Cahlíková Lucie
Published: March 2019

Alkaloidal extracts of seven selected plants of the family Papaveraceae were studied with respect to their activity against six strains of pathogenic bacteria and their alkaloidal fingerprint. Twenty-four alkaloids were determined by GC/MS, and twenty of them identified from their mass spectra, retention times and retention indexes. In the antibacterial assay, three Gram-positive ( Enterorococcus faecalis, Staphylococcus aureus and S. hyicus), and three Gram-negative ( Escherichia coli, Proteus mirabilis and Pseudomonas aeruginosa) strains were used. The most promising antimicrobial activity was shown by the alkaloidal extract of Macleaya cordata with MIC values of 16 μg/mL for Staphylococcus aureus, 32 μg/mL for Enterococcus faecalis and 64 μg/mL for Staphylococcus hyicus and Escherichia coli. All the tested pure isoquinoline alkaloids were considered inactive within the tested concentrations.
Isolation of Phenolics from Rhizophora mangle by Combined Counter-current Chromatography and Gel-Filtration
Authors: Costa Fernanda das Neves , da Silva Marcos Daniel , Borges Ricardo Moreira , Leitão Gilda Guimarães
Published: March 2019

Nine phenolic compounds, quercetin, epi-catechin, catechin, 4-hydroxybenzoic acid, kaempferol 3- O-β-glucopyranoside, quercetin 3- O-β-glucopyranoside, quercetin 3- O-6″- trans-coumaroyl-β-glucoside, kaempferol 3- O-β-rutinoside and quercetin 3- O-β-rutinoside, were isolated from the EtOAc leaf extract of Rhizophora mangle (Rhizophoraceae) combining counter-current chromatography (CCC) and gel-filtration. A solvent system of n-hexane-ethyl acetate-methanol-water (1.5:6:1.5:6) was employed at the preliminary stage of EtOAc extract fractionation as it was shown to contain compounds that differed highly in their hydrophobicity. The obtained fractions were further purified by either CCC or gel-filtration depending on their complexity. The isolated compounds were analyzed by NMR spectroscopy and the proposed structures were confirmed by HRES/ESI/TOF MS. Some of these compounds were isolated and/or identified for the first time in R. mangle.
Phenolic Acids Profile, Antioxidant and Antibacterial Activity of Chamomile, Common Yarrow and Immortelle (Asteraceae)
Authors: Mekinić Ivana Generalić , Skroza Danijela , Ljubenkov Ivica , Krstulović Luka , Možina Sonja Smole , Katalinić Višnja
Published: March 2019

Chamomile, common yarrow and immortelle ethanolic extracts were chemically analysed with respect to phenolics. Twelve phenolic acids were separated and identified by HPLC-DAD and the presence of rosmarinic acid was additionally confirmed by LC-MS. Five methods were applied for the evaluation of extracts’ antioxidant properties (FRAP, DPPH, ABTS, chelating activity, Briggs-Rauscher reaction), while the antibacterial activity was tested against some of the major food-borne pathogens ( Campylobacter coli, Escherichia coli, Salmonella Infantis, Bacillus cereus, Listeria monocytogenes and Staphylococcus aureus). Immortelle extract was the richest in phenolics with a dominant flavonoid fraction, while the other two extracts contained higher amount of non-flavonoids. The phenolic acid profile also varied; high concentration of rosmarinic acid was found in chamomile and common yarrow, while caffeic acid was dominant in immortelle. The best antioxidant properties were obtained for chamomile extract, while good antimicrobial activity, especially against Gram-positive bacterial species, was detected for immortelle. The obtained results could be used as a tool for chemotaxonomic classification of the investigated plants or for their potential application as natural antioxidants/antimicrobials.
Activity-guided Fractionation of Ipomea fistulosa Leaves for Pro-inflammatory Cytokines and Nitric Oxide Inhibitory Constituents
Authors: Patel Neeraj K. , Ramandeep  , Bhutani Kamlesh K.
Published: March 2019

In the continuous search for new anti-inflammatory agents from natural products, dichloromethane (DCM), ethyl acetate (EtOAc) and methanol (MeOH) extracts of Ipomea fistulosa leaves were evaluated for inhibition of production of nitric oxide (NO), interleukin 1beta (IL-1β) and tumor necrosis factor alpha (TNF-α) in lipopolysaccharide (LPS) stimulated J774A.1 cells. Among the tested extracts, the ethyl acetate (EtOAc) extract was found to be most active and activity based fractionation of this extract by column chromatography led to the identification of seven compounds for the first time from this plant. Furthermore, 3,4-dimethoxy cinnamic acid (1) exhibited two folds more potent inhibition of LPS-induced NO production (IC50 = 10.7 μg/mL) as compared with the standard, L-NAME (IC50=19.8 μg/mL). The present study supports the use of Ipomea fistulosa leaves for the treatment of inflammation.
Reactive Oxygen Species Scavenging Activity of Jixueteng Evaluated by Electron Spin Resonance (ESR) and Photon Emission
Authors: Toyama Toshizo , Wada-Takahashi Satoko , Takamichi Maomi , Watanabe Kiyoko , Yoshida Ayaka , Yoshino Fumihiko , Miyamoto Chihiro , Maehata Yojiro , Sugiyama Shuta , Takahashi Shun-suke , Todoki Kazuo , Lee Masaichi-Chang-il , Hamada Nobushiro
Published: March 2019

Jixueteng, the dried stem of Spatholobus suberectus Dunn (Leguminosae), is a traditional Chinese herbal medicine that is commonly classified as a herb that promotes blood circulation and can be used to treat blood stasis. The aim of this study was to examine the reactive oxygen species (ROS) scavenging activity of Jixueteng and other herbal medicines. The ROS scavenging activities of the water extracts of Jixueteng, Cnidium officinale and Salvia miltiorrhiza were examined using an electron spin resonance (ESR) technique and faint luminescence measurement. The ESR signal intensities of the superoxide anion (O2•-) and hydroxyl radical (HO•) were reduced more by Jixueteng than the other herbal medicines we tested. High photon emission intensity to hydrogen peroxide (H2O2) and HO• was observed in Jixueteng using the XYZ chemiluminescence system that was used as faint luminescence measurement and analysis. The results of the present study revealed that the ROS scavenging activity of 8% Jixueteng was the strongest among the herbal medicines we tested. It has been reported that Jixueteng includes various polyphenols. In the ROS scavenging activity by Jixueteng, it is supposed that the antioxidant activity caused by these polyphenols would contribute greatly. In conclusion, a water extract component of Jixueteng had potent free radical scavenging activity and an antioxidative effect that inhibited the oxidative actions of O2•-, H2O2 and HO•. Therefore, Jixueteng represents a promising therapeutic drug for reactive oxygen-associated pathologies.
Volatile Constituents of the Seeds and Fruit of Pycnocycla nodiflora
Authors: Nasr Mojdeh , Asgarpanah Jinous
Published: March 2019

The essential oil contents of the fruit and seeds of Pycnocycla nodiflora Decne. ex Boiss. growing wild in southern Iran were found to be 0.05% and 0.1% (v/w), respectively based on the fresh weight. The oils were analyzed by GC and GC–MS. Twenty-eight and twenty-seven constituents, representing 94.7% and 89.6% of the oils were identified, respectively. The major components of the P. nodiflora fruit oil were identified as E-sesquilavandulol (18.6%), spathulenol (11.9%), δ-cadinol (9.0%), t-cadinol (8.9%) and β-caryophyllene (7.9%), while the main components of that of the seeds were characterized as E-sesquilavandulol (17.2%), lavandulyl acetate (13.5%), β-caryophyllene (11.1%), bicyclogermacrene (10.5%), δ-cadinol (9.0%) and t-cadinol (6.8%).
Chemical Compositions and Antimicrobial Activity of the Essential Oils of Piper abbreviatum, P. erecticaule and P. lanatum (Piperaceae)
Authors: Salleh Wan Mohd Nuzul Hakimi Wan , Ahmad Farediah , Yen Khong Heng
Published: March 2019

The study was designed to examine the chemical composition and antimicrobial activities of essential oils extracted from the aerial parts of three Piper species: Piper abbreviatum, P. erecticaule and P. lanatum, all from Malaysia. GC and GC/MS analysis showed qualitative and quantitative differences between these oils. GC and GC-MS analysis of P. abbreviatum, P. erecticaule and P. lanatum oils resulted in the identification of 33, 35 and 39 components, representing 70.5%, 63.4% and 78.2% of the components, respectively. The major components of P. abbreviatum oil were spathulenol (11.2%), ( E)-nerolidol (8.5%) and β-caryophyllene (7.8%), whereas P. erecticaule oil mainly contained β-caryophyllene (5.7%) and spathulenol (5.1%). Borneol (7.5%), β-caryophyllene (6.6%) and α-amorphene (5.6%) were the most abundant components in P. lanatum oil. Antimicrobial activity was carried out using disc diffusion and broth micro-dilution method against nine microorganisms. All of the essential oils displayed weak activity towards Gram-positive bacteria with MIC values in the range 250–500 μg/mL. P. erecticaule oil showed the best activity on Aspergillus niger (MIC 31.3 μg/mL), followed by P. lanatum oil (MIC 62.5 μg/mL). This study demonstrated that the essential oils have potential as antimicrobial agents and may be useful in the pharmaceutical and cosmetics industries.
Chemical Composition and Biological Activities of the Essential Oils from Two Pereskia Species Grown in Brazil
Authors: Souza Lucéia Fátima , de Barros Ingrid Bergman Inchausti , Mancini Emilia , Martino Laura De , Scandolera Elia , Feo Vincenzo De
Published: March 2019

The chemical composition of the essential oils of Pereskia aculeata Mill. and P. grandifolia Haw. (Cactaceae), grown in Brazil, was studied by means of GC and GC-MS. In all, 37 compounds were identified, 30 for P. aculeata and 15 for P. grandifolia. Oxygenated diterpenes are the main constituents, both in the oil of P. grandifolia (55.5%) and in that of P. aculeata (29.4%). The essential oils were evaluated for their in vitro phytotoxic activity against germination and initial radicle growth of Raphanus sativus L., Sinapis arvensis L., and Phalaris canariensis L. seeds. The essential oil of P. grandifolia, at all doses tested, significantly inhibited the radicle elongation of R. sativus. Moreover, the antimicrobial activity of the essential oils was assayed against ten bacterial strains. The essential oils showed weak inhibitory activity against the Gram-positive pathogens.
Stemona Alkaloids: Biosynthesis, Classification, and Biogenetic Relationships
Authors: Wang Feng-Peng , Chen Qiao-Hong
Published: March 2019

Stemona alkaloids form a unique class, which can be attributed to hemiterpenoid pyrrolidine- and monoterpenoid pyrrolidine-class alkaloids originated from L-ornithine and glutamic acid. By the end of 2013, approximately 183 Stemona alkaloids had been isolated from nature. The literature on Stemona alkaloids in the realms of chemical structure, synthesis, and bioactivities has been elegantly summarized and reviewed. We thus summarize in this review the biosynthesis, structural classification, and the intrinsic, biogenetic relationships of Stemona alkaloids. Based on the comprehensive consideration of biogenetic pathways and chemical features, the 183 Stemona alkaloids are classified into two classes (hemiterpenoid pyrrolidine- and monoterpenoid pyrrolidine) and fourteen types.
Chemotypes of Ligularia vellerea, its Hybrids, and L. melanothyrsa
Authors: Shimizu Anna , Inoue Kyosuke , Ichihara Mayu , Hanai Ryo , Saito Yoshinori , Okamoto Yasuko , Tori Motoo , Gong Xun , Kuroda Chiaki
Published: March 2019

Ligularia vellerea and L. melanothyrsa have been found to share chemical characteristics based on geography. In one chemotype (Shangrila type), the major components were either 15-oxygenated furanoeremophilanes or eremophilanolides; and in another (Luguhu type), either 1-angeloyloxyfuranoeremophilanes or corresponding lactones. The two L. vellerea samples were found to have experienced hybridization with either L. cyathiceps or L. kanaitzensis; however, compounds typical of L. vellerea alone were isolated from them.
Phytotoxicity of Triterpenes and Limonoids from the Rutaceae and Meliaceae. 5α,6β,8α,12α-Tetrahydro-28-norisotoonafolin – a Potent Phytotoxin from Toona ciliata
Authors: Nebo Liliane , Varela Rosa M. , Molinillo José M. G. , Severino Vanessa G. P. , Sarria André L. F. , Cazal Cristiane M. , Fernandes Maria Fátima das Graças , Fernandes João B. , Macías Francisco A.
Published: March 2019

Limonoids and triterpenes are the largest groups of secondary metabolites and have notable biological activities. Meliaceae and Rutaceae are known for their high diversity of metabolites, including limonoids, and are distinguished from other families due to the frequent occurrence of such compounds. The increased interest in crop protection associated with the diverse bioactivity of these compounds has made these families attractive in the search for new allelopathic compounds. In the study reported here we evaluated the bioactivity profiles of four triterpenes (1–4) and six limonoids (5–10) from Meliaceae and Rutaceae. The compounds were assessed in a wheat coleoptile bioassay and those that had the highest activities were tested on the standard target species Lepidium sativum (cress), Lactuca sativa (lettuce), Lycopersicon esculentum (tomato) and Allium cepa (onion). Limonoids showed phytotoxic activity and 5 α,6 β,8 α,12 α-tetrahydro-28-norisotoonafolin (10) and gedunin (5) were the most active, with bioactivity levels similar to, and in some cases better than, those of the commercial herbicide Logran. The results indicate that these products could also be allelochemicals involved in the ecological interactions of these plant species.
Triterpene Glycosides of Sea Cucumbers (Holothuroidea, Echinodermata) as Taxonomic Markers
Authors: Kalinin Vladimir I. , Avilov Sergey A. , Silchenko Alexandra S. , Stonik Valentin A.
Published: March 2019

Triterpene glycosides are characteristic metabolites of sea cucumbers (Holothurioidea, Echinodermata). The majority of the glycosides belong to the holostane type {lanostane derivatives with an 18(20)-lactone}. Carbohydrate chains of these glycosides contain xylose, glucose, quinovose, 3- O-methylglucose, and, rarely, 3- O-methylxylose, 3- O-methylglucuronic acid, 3- O-methylquinovose, and 6- O-acetyl-glucose. The glycosides are specific for genera, groups of genera and even for species. The advantages and problems in the use of triterpene glycosides as taxonomic markers in the systematics of sea cucumbers are discussed.
Amurensiosides L-P, Five New Cardenolide Glycosides from the Roots of Adonis amurensis
Authors: Kubo Satoshi , Kuroda Minpei , Yokosuka Akihito , Sakagami Hiroshi , Mimaki Yoshihiro
Published: March 2019

Five new cardenolide glycosides, amurensiosides L–P (1–5), were isolated from the roots of Adonis amurensis. Their structures were determined based on extensive spectroscopic analysis, including two-dimensional (2D) NMR data, and on the results of hydrolytic cleavage. Compounds 1–5 were evaluated for their cytotoxic activities against HL-60 human promyelocytic leukemia and HSC-2 human oral squamous cell carcinoma cell lines.
Spirostane-type Saponins from Dracaena fragrans « Yellow Coast »
Authors: Rezgui Abdelmalek , Mitaine-Offer Anne-Claire , Miyamoto Tomofumi , Tanaka Chiaki , Lacaille-Dubois Marie-Aleth
Published: March 2019

Three steroidal glycosides were isolated from the bark of Dracaena fragrans (L.) Ker Gawl. « Yellow Coast », and a fourth from the roots and the leaves. Their structures were characterized on the basis of extensive 1D and 2D NMR experiments and mass spectrometry, and by comparison with NMR data of the literature. These saponins have the spirostane-type skeleton and are reported in this species for the first time.
Chemical Prospection of Important Ayurvedic Plant Tinospora cordifolia by UPLC-DAD-ESI-QTOF-MS/MS and NMR
Authors: Bala Manju , Verma Praveen Kumar , Awasthi Shiv , Kumar Neeraj , Lal Brij , Singh Bikram
Published: March 2019

A rapid, sensitive, and accurate ultra-performance liquid chromatography coupled with mass spectrometric method (UPLC-MS) was developed and validated for simultaneous determination of four bioactive compounds, syringin (3), cordifolioside A (4), magnoflorine (6) and tinocordiside (10) in the stem of Tinospora cordifolia. The analysis was performed using an Acquity C18 column and gradient elution of 0.05% formic acid in water and acetonitrile at a detection wavelength of 267 nm in 5 min. A high correlation coefficient (r2 > 0.998) indicated good correlation between investigated compounds concentration and their peak area within the test ranges. The LODs for compounds 3, 4, 6 and 10 were 1.95, 0.97, 3.90 and 0.97 ng/mL, respectively, and LOQs were 6.64, 3.20, 12.87 and 3.20 ng/mL, respectively. The overall intra- and inter-day variations of the four compounds were less than 1%. The variation of these four bioactive compounds in T. cordifolia hosted on fifteen different trees was also determined. The compounds (3, 4, 6 and 10) were found in high amount in the T. cordifolia hosted on Azadirachta indica and Mangifera indica as compared with other plants. Twelve compounds were identified on the basis of their mass and UV-vis spectra. The NMR fingerprinting of the extract revealed the presence of alkaloids, fatty acid methyl esters, polysaccharides and marker components of T. cordifolia.
Kopsiyunnanines J1 and J2, New Strychnos-type Homo-Monoterpenoid Indole Alkaloids from Kopsia arborea
Authors: Kitajima Mariko , Koyama Tetsuya , Wu Yuqiu , Kogure Noriyuki , Zhang Rongping , Takayama Hiromitsu
Published: March 2019

Two new indole alkaloids, kopsiyunnanines J1 and J2, were isolated from Yunnan Kopsia arborea, and their structures were determined by spectroscopic analyses. Kopsiyunnanines J1 and J2 are unprecedented Strychnos-type indole alkaloids having an additional C1 unit in the secologanin moiety of the molecule.
Diversity in the Flavonoid Composition of Stellera chamaejasme in the Hengduan Mountains
Authors: Shirai Kei , Okamoto Yasuko , Tori Motoo , Kawahara Takayuki , Gong Xun , Noyama Teruaki , Watanabe Eiji , Kuroda Chiaki
Published: March 2019

The presence of diversity in the Stellera chamaejasme population was found via their chemical composition. The eight collected samples were grouped into two chemotypes on the basis of the amount of neochamaejasmin B and chamaejasmine. Diversity was also found in the amount of afzelechin. The stereochemistry of neochamaejasmin B was confirmed by NOE experiment.
Constituents of Indonesian Medicinal Plant Averrhoa bilimbi and Their Cytochrome P450 3A4 and 2D6 Inhibitory Activities
Authors: Auw Lidyawati , Subehan  , Sukrasno  , Kadota Shigetoshi , Tezuka Yasuhiro
Published: March 2019

As constituents of Averrhoa bilimbi leaves we identified three new compounds (1-3) together with 12 known ones (4-15); their inhibitory activities on cytochrome P450 3A4 (CYP3A4) and 2D6 (CYP2D6) were examined. Among the isolated compounds, the mixture of 1 and 2, and compounds 4 and 9 showed strong inhibition on CYP3A4, but mild or no inhibition on CYP2D6. These compounds revealed the characteristics of 1) time- and concentration-dependent inhibition, 2) requirement of NADPH for the inhibition, 3) no protection by nucleophiles, and 4) suppression of the inhibition by competitive inhibitor. Thus, they are suggested to be mechanism-based inactivators of CYP3A4 and CYP2D6. The kinetic parameters for the inactivation (kinact and KI) were 0.19 min–1 and 36.7 μM for the mixture of 1 and 2, 0.126 min–1 and 10.5 μM for 4, and 0.29 min–1 and 23.4 μM for 9.
Flavonoids from Curcuma longa Leaves and their NMR Assignments
Authors: Jiang Chia-Ling , Tsai Sheng-Fa , Lee Shoei-Sheng
Published: March 2019

Chemical investigation of the n-BuOH-soluble fraction of the EtOH extract of the aerial part of Curcuma longa led to the isolation of 11 flavonol glycosides and one dihydroflavonol glucoside (1) via chromatography over Sephadex LH-20 and Lobar RP-18 columns. Although they are known, the 1H and 13C NMR data recorded in CD3OD rather than the common DMSO- d6 are doubly checked via extensive 2D NMR spectroscopic analyses, leading to some revisions of the reported data, especially for the glycon part.
Phytochemical Analysis and Biological Evaluation of Selected African Propolis Samples from Cameroon and Congo
Authors: Papachroni Danai , Graikou Konstantia , Kosalec Ivan , Damianakos Harilaos , Ingram Verina , Chinou Ioanna
Published: March 2019

The objective of this study was the chemical analysis of four selected samples of African propolis (Congo and Cameroon) and their biological evaluation. Twenty-one secondary metabolites belonging to four different chemical groups were isolated from the 70% ethanolic extracts of propolis and their structures were elucidated on the basis of spectral evidence. Three triterpenes and two diprenyl-flavonoids were identified from Congo propolis, which has been investigated for the first time, while thirteen triterpenes, three diprenyl-flavonoids, two monoterpenic alcohols and one fatty acid ester have been identified from Cameroon propolis samples. To our knowledge, the identified diprenyl-flavonoids, as well as five of the isolated and determined triterpenes, are reported for the first time in propolis. Moreover, the total polyphenol content was estimated in all extracts and the antimicrobial activities of all four extracts were studied against six Gram-positive and -negative bacteria and three pathogenic fungi, showing an interesting antibacterial profile.
Improved Chromatographic Fingerprinting Combined with Multi-components Quantitative Analysis for Quality Evaluation of Penthorum chinense by UHPLC-DAD
Authors: Deng Wangping , Xu Tongtong , Yang Min , Cui Yajun , Guo De-an
Published: March 2019

A high performance liquid chromatographic (HPLC) fingerprint is commonly used for quality consistency evaluation of herbal medicines. Recently, an improved chromatographic technique resulted in ultra high performance liquid chromatography (UHPLC), which could provide higher resolution in less time under higher pressure using finer particles (less than 2μm) of stationary phase. A simple and sensitive method was developed and validated for fingerprint analysis of Penthorum chinense Pursh (PC), with the simultaneous determination of seven components using UPLC coupled with a diode-array detector (DAD). It took less than 20 min for analysis of one sample. Both similarity analysis and principle components analysis (PCA) were employed to evaluate the quality consistency of 17 sample batches. The analysis was performed on a Waters ACQUITY UPLC HSS T3 (2.1 × 150 mm, 1.7 μm) column, which was maintained at 45°C and the eluents were monitored with DAD at 270 nm. A gradient elution with acetonitrile and water containing 0.075% phosphoric acid was used. The solvent flow rate was 0.4 mL/min. Standard calibration curves showed good linear behavior (R2>0.9994) in the range of 0.20-337.05 μg/mL. Acceptable repeatability (RSD<0.61%), reproducibility (RSD<2.72%), stability (RSD<1.59%) and recovery in the range of 94.7%-102.9% were obtained (precision and accuracy). The validated method was successfully applied to evaluate the quality of 21 samples of PC.
Maqui berry vs Sloe berry – Liquor-based Beverage for New Development
Authors: Gironés-Vilaplana Amadeo , Moreno Diego A. , García-Viguera Cristina
Published: March 2019

“Pacharán” is an aniseed liquor-based beverage made with sloe berry ( Prunus spinosa L.) that has been produced in northern Spain. On the other hand, maqui berry ( Aristotelia chilensis) is a common edible berry from Chile, and currently under study because of its multiple beneficial effects on health. The aim of this work was to design a new aniseed liquor-based beverage with maqui berry, as an industrial alternative to a traditional alcoholic product with bioactive berries. The characterization of its composition, compared with the traditional “Pacharán”, and its evolution during maceration (6 and 12 months) showed that the new maqui liquor had significantly-higher anthocyanin retention over time. More studies on the organoleptic properties and bioactivity are underway.
Rapid Dereplication and Identification of the Bioactive Constituents from the Fungus, Leucocoprinus birnbaumii
Authors: Brkljača Robert , Urban Sylvia
Published: March 2019

A series of fatty acids were rapidly dereplicated and partially identified from the flowerpot fungus, Leucocoprinus birnbaumii using HPLC-NMR and HPLC-MS. Subsequent off-line isolation unequivocally established the structures, and anti-microbial testing concluded that the fatty acids displayed moderate but selective anti-microbial activity. This represents the first report of these compounds occurring in this particular terrestrial fungus.
Cardanols, Long Chain Cyclohexenones and Cyclohexenols from Lannea schimperi (Anacardiaceae)
Authors: Okoth Dorothy A. , Koorbanally Neil A.
Published: March 2019

Alkenyl cyclohexenones (1a-d), alkenyl cyclohexenols (2a-c and 3b-d) and cardanols (4a-d) were isolated from the stem bark and root of Lannea schimperi. The alkenyl cyclohexenones (1a and 1d) and cardanols (4a and 4d) have side chains which have not been reported previously, in combination with the core skeletal structures. In addition, compounds 2a-c and 3b-d are all new cyclohexenols. Also isolated were the triterpenes, taraxerone and taraxerol, and sitosterol. The suite of compounds isolated (cyclohexenones and cyclohexenols) make up a nice biosynthetic pathway to the cardanols. The 5-[alkenyl]-4,5-dihydroxycyclohex-2-enone mixture (1a-d) exhibited good in vitro cytotoxicity against the Chinese Hamster Ovarian mammalian cell-line. The compounds were identified mainly from GCMS and NMR spectroscopic techniques.
Potent Anti-Calmodulin Activity of Cyclotetradepsipeptides Isolated from Isaria fumosorosea Using a Newly Designed Biosensor
Authors: Madariaga-Mazón Abraham , González-Andrade Martín , Toriello Conchita , Navarro-Barranco Hortensia , Mata Rachel
Published: March 2019

Seven cyclotetradepsipeptides, namely beauverolides C (1), F (2), I (3), Ja (4), L (5), M (6), and N (7), were isolated from the entomopathogenic fungus Isaria fumosorosea. The beauverolides were evaluated as potential calmodulin (CaM) inhibitors using the newly designed CaM biosensor hCaM M124C- AF350; these peptides displayed high affinity to the protein with dissociation constants ( Kd) ranging from 0.078 μM to 3.44 μM. Beauverolide Ja, the only one containing a tryptophan residue in its structure, showed the highest affinity. The docking study predicted that beauverolides could bind to CaM in the same site of interaction as chlorpromazine, a well-known calmodulin ligand.
Chemical Composition and Biological Activity of Essential Oils of Dracocephalum heterophyllum and Hyssopus officinalis from Western Himalaya
Authors: Stappen Iris , Wanner Jürgen , Tabanca Nurhayat , Wedge David E. , Ali Abbas , Kaul Vijay K. , Lal Brij , Jaitak Vikas , Gochev Velizar K. , Schmidt Erich , Jirovetz Leopold
Published: March 2019

The essential oils of two representatives of the Lamiaceae, Dracocephalum heterophyllum Benth. and Hyssopus officinalis L., are described for their antifungal, antibacterial, larvicidal and inect biting deterrent activities. Additionally, the chemical compositions of the essential oils, analyzed by simultaneous GC-MS and GC-FID, and odor descriptions are given. The main components of H. officinalis oil were pinocarvone, cis-pinocamphone, and β-pinene. Citronellol was found as the main compound of D. heterophyllum essential oil. Antibacterial testing by agar dilution assay revealed greater activity of D. heterophyllum against Staphylococcus aureus compared with H. officinalis. D. heterophyllum essential oil also showed promising antifungal activity against Colletotrichum species and was more toxic to Aedes aegypti larvae in a larvicial bioassay. Both essential oils showed high activity in the biting deterrent bioassay.
Radical Scavenging and Antioxidant Activities of Essential Oil Components – An Experimental and Computational Investigation
Authors: Sharopov Farukh S. , Wink Michael , Setzer William N.
Published: March 2019

The antioxidant activities of eighteen different essential oil components have been determined using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging assay, the 2,2 ’-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid (ABTS) radical cation assay, and the ferric reducing antioxidant power (FRAP) assay. The phenolic compounds, carvacrol, thymol, and eugenol, showed the best antioxidant activities, while camphor, menthol, and menthone were the least active. The structural and electronic properties of the essential oil components were assessed using density functional theory (DFT) at the B3LYP/6-311++G** level. Correlations between calculated electronic properties and antioxidant activities were generally poor, but bond-dissociation energies (BDEs) seem to correlate with DPPH radical-scavenging activities, and the ferric reducing antioxidant power (FRAP) assay correlated with vertical ionization potentials calculated at the Hartree-Fock/6-311++G** level.
Enzyme-Mediated Synthesis of Sesquiterpenes
Authors: Serra Stefano
Published: March 2019

This review article focuses mainly on the scientific developments concerning the enzyme-mediated synthesis of sesquiterpenes which have been reported in the academic and patent literature during the last twenty years. Nevertheless, this is not a comprehensive description of every single biotransformation involving sesquiterpenes. Only synthetic approaches that have represented a new and innovative perspective from a scientific standpoint are reported. More specifically, the review describes in depth how the use of metabolic engineering of the microbial biotransformations and of the isolated enzymes were exploited in order to perform chemo- and stereoselective chemical transformations of interest for sesquiterpenes synthesis.
Lignins of Bioenergy Crops: A Review
Authors: Guragain Yadhu N. , Herrera Alvaro I. , Vadlani Praveen V. , Prakash Om
Published: March 2019

Lignin provides structural support, a mechanical barrier against microbial infestation and facilitates movement of water inside plant systems. It is the second most abundant natural polymer in the terrestrial environments and possesses unique routes for the production of bulk and specialty chemicals with aromatic/phenolic skeletons. The commercial applications of lignin are limited and it is often recognized for its negative impact on the biochemical conversion of lignocellulosic biomass to fuels and chemicals. Understanding of the structure of lignin monomers and their interactions among themselves, as well as with carbohydrate polymers in biomass, is vital for the development of innovative biomass deconstruction processes and thereby valorization of all biopolymers of lignocellulosic residues, including lignin. In this paper, we review the major energy crops and their lignin structure, as well as the recent developments in biomass lignin characterization, with special focus on 1D and 2D Nuclear Magnetic Resonance (NMR) techniques.
Plant Chemical Defenses: Are all Constitutive Antimicrobial Metabolites Phytoanticipins?
Authors: Pedras M. Soledade C. , Yaya Estifanos E.
Published: March 2019

A critical perspective on phytoanticipins, constitutive plant secondary metabolites with defensive roles against microbes is presented. This mini-review focuses on the chemical groups and structural types of defensive plant metabolites thus far not reviewed from the phytoanticipin perspective: i) fatty acid derivatives and polyketides, ii) terpenoids, iii) shikimates, phenylpropanoids and derivatives, and iv) benzylisoquinoline and pyrrolizidine alkaloids. The more traditional groups of phytoanticipins are briefly summarized, with particular focus on the latest results: i) benzoxazinoids, ii) cyanogenic glycosides, iii) glucosinolates and their metabolic products, and iv) saponins. Current evidence suggests that a better understanding of the functions of plant metabolites will drive their application to protect crops against microbial diseases.
Ursolic Acid and Oleanolic Acid from Eriobotrya fragrans Inhibited the Viability of A549 Cells
Authors: Yuan Yuan , Gao Yongshun , Song Gang , Lin Shunquan
Published: March 2019

Loquat { Eriobotrya japonica (Lindl.)}, a kind of Chinese herb, has many efficacies such as anti-inflammatory, antimicrobial and curing chronic bronchitis. However, reports on the pharmacological action of wild loquat extract are limited. In this work, the A549 cell line was selected to study the inhibitory effect of ursolic acid and oleanolic acid (UA, OA) from the leaves of E. fragrans. Results showed that UA/OA inhibited A549 cell viability and induced apoptosis in a dose and time dependent manner. The cell fraction in the G0/G1 phase dramatically increased under treatment with UA/OA. Data showed that UA activated the expression of PARP. UA and OA down-regulated MMP-2 and Bcl-2; on the contrary, they up-regulated Bid. This work demonstrated that UA/OA extracted from wild loquat leaves can significantly inhibit the viability of A549 cells.
New Cytotoxic Triterpene Glycoside from the East China Sea Cucumber Holothuria nobilis
Authors: Zhang Jia-Jia , Zhu Qi-Ke , Wu Jun , Zhang Hui-Wen
Published: March 2019

A new cytotoxic triterpene glycoside named nobiliside E (1) has been obtained from the East China Sea cucumber Holothuria nobilis Selenka. Its structure was determined on the basis of NMR spectroscopic and MS analyses, together with chemical evidence. The new compound showed significant cytotoxicity to eight human tumor cell lines with IC50 values in the range of 0.53–4.06 μg/mL.