bluuebunny/crossref_metadata_2025 huggingface dataset:
neo-Clerodane Diterpenoids from Scutellaria galericulata
Authors: Bozov Petko I. , Penchev Plamen N. , Coll Josep
Published: March 2019

Four neo-clerodane diterpenoids, neoajugapyrin A, scutegalerins A and B and scutecolumnin C have been isolated from the acetone extract of the aerial parts of Scutellaria galericulata. Neoajugapyrin A and scutecolumnin C are reported in this species for the first time, whereas scutegalerins A and B are new compounds. NMR data of neoajugapyrin A are discussed in detail to support the proposed revised structure of ajugapyrin A.
New Ursane Triterpene from the Fruits of Terminalia arjuna
Authors: Hossain Rashadul , Sultana Rajia , Adhikari Aychout , Choudhary Muhammad Iqbal , Ali Yusuff , Zaman Shahed
Published: March 2019

A new ursane triterpene, torment (2 α,3 β,19 α-trihydroxyurs-12-en) (1), was isolated from the fruits of Terminalia arjuna along with four known ursane and oleane triterpenes. The structures were established on the basis of extensive NMR (1D & 2D) and MS (EI & ESI) studies. Tormentic acid (2), 19α-hydroxy asiatic acid (3) and olean-12-en-2 α,3 β-diol (4) were isolated for the first time from this species. Compounds 1 and 2 lacked significant enzyme inhibition, cytotoxicity, immunomodulatory and antiglycation activities.
New Acylated Triterpene Glycosides from the Roots of Polygala tenuifolia
Authors: Kuroda Minpei , Shizume Takaaki , Mimaki Yoshihiro
Published: March 2019

Two new and five known acylated triterpene glycosides were isolated from the MeOH extract of the roots of Polygala tenuifolia. Based on extensive spectroscopic analysis, including 2D NMR experiments, and the results of alkaline hydrolysis, the structures of the new compounds were assigned as 3β-[(β-D-glucopyranosyl)oxy]–2β,27-dihydroxyolean-12-ene-23,28-dioic acid 28- O-β-D-apiofuranosyl-(1→3)-[β-D-galactopyranosyl-(1→4)-β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-3- O-( E)-3,4,5-trimethoxycinnamoyl-β-D-fucopyranosyl ester (1) and 3β-[(β-D-glucopyranosyl)oxy]–2β,27-dihydroxyolean-12-ene-23,28-dioic acid 28- O-β-D-apiofuranosyl-(1→3)-[β-D-galactopyranosyl-(1→4)-β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-4- O-( E)-3,4-dimethoxycinnamoyl-β-D-fucopyranosyl ester (2).
Pungent and Bitter, Cytotoxic and Antiviral Terpenoids from Some Bryophytes and Inedible Fungi
Authors: Asakawa Yoshinori , Nagashima Fumihiro , Hashimoto Toshihiro , Toyota Masao , Ludwiczuk Agnieszka , Komala Ismiarni , Ito Takuya , Yagi Yasuyuki
Published: March 2019

Most liverworts elaborate characteristic odiferous, pungent and bitter tasting compounds many of which show antimicrobial, antifungal, antiviral, allergenic contact dermatitis, cytotoxic, insecticidal, anti-HIV, superoxide anion radical release, plant growth regulatory, neurotrophic, NO production inhibitory, muscle relaxant, antiobesity, piscicidal and nematocidal activities. Several inedible mushrooms produce female spider pheromones, strong antioxidant, and cytotoxic compounds. The present paper is concerned with the extraction and isolation of terpenoids from some bryophytes and inedible fungi and their pungent and bitter taste, and cytotoxic and antiviral activity.
Activation of Cell-mediated Immunity by Morinda citrifolia Fruit Extract and Its Constituents
Authors: Murata Kazuya , Abe Yumi , Futamura-Masuda Megumi , Uwaya Akemi , Isami Fumiyuki , Matsuda Hideaki
Published: March 2019

Morinda citrifolia, commonly known as noni, is a traditional natural medicine in French Polynesia and Hawaii. Functional foods derived from M. citrifolia fruit have been marketed to help prevent diseases and promote good health. The objective of this study was to assess the effects of M. citrifolia fruit on cell-mediated immunity. In the picryl chloride-induced contact dermatitis test, M. citrifolia fruit extract (Noni-ext) inhibited the suppression of cell-mediated immunity by immunosuppressive substances isolated from freeze-dried ascites of Ehrlich carcinoma-bearing mice (EC-sup). In addition, Noni-ext inhibited reduction of IL-2 production in EC-sup-treated mice and activated natural killer cells in normal mice. These results suggest that Noni-ext has multiple effects on the recovery of cell-mediated immunity. Furthermore, we investigated the active principles of Noni-ext and identified an iridoid glycoside, deacetylasperulosidic acid. Oral administration of deacetylasperulosidic acid inhibited the reduction of ear swelling, and also cancelled the suppression of IL-2 production along with the activation of natural killer cells in the same manner as that of Noni-ext.
Alkaloids from Marine Sponges as Stimulators of Initial Stages of Development of Agricultural Plants
Authors: Anisimov Mikhail M. , Chaikina Elena L. , Utkina Natalia K
Published: March 2019

Damirone A (1), damirone B (2), makaluvamine G (3), debromohymenialdisine (4), and dibromoagelaspongin (5) were examined for their ability to stimulate growth of seedling roots of barley (Hordeum vulgare L.), buckwheat (Fagopyrum esculentum Moench), corn (Zea mays L.), soy {Glycine max (L.) Merr.}, and wheat (Triticum aestivum L.). It was shown that the stimulatory effects depend on the chemical structure of the alkaloids and on the plant species. Compounds 1, 3, and 4 are efficient for growth of seedling roots of barley, compounds 2-5, at different concentrations, stimulate growth of buckwheat roots, and compound 5 stimulates growth of wheat roots. These compounds can be recommended for field study as plant growth stimulators.
Two New Thyminenol Derivatives from the Marine Sponge Haliclona sp
Authors: Wang Bin , Lin Yaocai , Chen Yinning , Huang Riming
Published: March 2019

Investigation of the marine sponge Haliclona sp. led to the isolation of two new thyminenol derivatives, named cis-thyminenol (1) and trans-thyminenol (2). The structures of the new isolates were elucidated on the basis of extensive spectroscopic analysis.
In vitro Cultures of Bituminaria bituminosa: Pterocarpan, Furanocoumarin and Isoflavone Production and Cytotoxic Activity Evaluation
Authors: D'Angiolillo Francesca , Pistelli Laura , Noccioli Cecilia , Ruffoni Barbara , Piaggi Simona , Scarpato Roberto , Pistelli Luisa
Published: March 2019

Bituminaria bituminosa L. is known for producing several compounds with considerable pharmaceutical interest, such as phenylpropanoids, furanocoumarins and pterocarpans. In vitro cultures of seedlings, shoots, and callus have been produced to obtain plant materials useful for the production of these metabolites. The secondary metabolite profile was evaluated by HPLC-DAD. The extracts of all the in vitro material contained the flavonoid daidzein, while plicatin B, erybraedin C and bitucarpin A were found only in the extracts of the in vitro shoots and in wild shoots. The furanocoumarins angelicin and psoralen were found in in vivo and in vitro plants, but in the callus were not detectable. The extracts were also tested for cytotoxic activity in HeLa cell culture; the highest level of cytotoxicity was found in in vitro shoot extracts.
Antioxidant Activity and Phenolic Content of Bergenia crassifolia, B. x ornata and B. ciliata
Authors: Hendrychová Helena , Vildová Anna , Kočevar-Glavač Nina , Tůmová Lenka , Kanybekovna Elnura Abdykerimova , Tůma Jiří
Published: March 2019

This study focused on a phytochemical analysis of Bergenia crassifolia (L.) Fritsch., B. ciliata (Haw.) Sternb., and B. x ornata Stein. and evaluation of their free radical scavenging properties. Arbutin and total tannin contents of the leaves of the Bergenia species were determined during different seasons. The present study also aimed at analyzing, for the first time, environmental influence on concentrations of phenolic metabolites in Bergenia leaves. The highest total tannin content was found in the leaves of B. crassifolia (24.9 – 48.7 mg.g−1 DW) and B. x ornata (36.9 mg.g−1 DW). The highest amount of arbutin was in the leaves of B. x ornata (35.8 – 51.0 mg.g−1 DW) and B. crassifolia (24.6 – 41.7 mg.g−1 DW). Autumn was better than spring for the collection of Bergenia leaves for the highest amount of arbutin ( B. x ornata: 51.0 mg.g−1 DW). Free radical scavenging potential, in DPPH and ABTS assays, of the water leaf extracts revealed that extracts of B. crassifolia and B. x ornata are the most active radical scavengers. Antioxidant activity correlated well with the content of total tannin, especially in the ABTS assay, which suggests an important role for these compounds in antioxidant activity. It was shown that phenolic concentrations in Bergenia leaves are affected by seasonal factors. A significant correlation was found between arbutin and tannin contents and the average humidity.
Structure Characterization and Adhesive Ability of a Polysaccharide from Tendrils of Parthenocissus heterophylla
Authors: Zhang Li , Deng Wenli
Published: March 2019

In order to reveal the structure of the polysaccharide and its contribution to the biological adhesion system of Parthenocissus heterophylla, a water-soluble polysaccharide (PT-A) was isolated from tendrils using DEAE-cellulose and Sephadex G-100 columns. PT-A mainly consisted of a backbone of (1→3)-linked-β-D-Galp residues and substituted at O-6 with side chains of (1→5)-linked-α-L-Ara f residues and glucomannopyranosyl residues. Individual polysaccharide chains of PT-A with the approximately height of 0.75 nm were observed by AFM. The analysis of force curves indicated that PT-A was a kind of elastic polysaccharide with a maximum adhesion force of 279.98 nN, which could be applied as a potential bio-adhesive.
Two Peptides, Cycloaspeptide A and Nazumamide A from a Sponge Associated Marine Actinobacterium Salinispora sp
Authors: Bose Utpal , Hodson Mark P. , Shaw P. Nicholas , Fuerst John A. , Hewavitharana Amitha K
Published: March 2019

Marine sponges are a major component of benthic communities and act as a reservoir for microbial species. In terms of biomass, they are the richest source of secondary metabolite production, with the potential to influence both benthic and pelagic systems. In most cases it is the sponge-associated microbes that account for many of the secondary metabolites assigned to the host. Here we report the occurrence of cycloaspeptide A, a fungus-derived cyclic peptide, in a culturable bacterium Salinispora arenicola. We have also identified nazumamide A, a sponge-derived linear tetrapeptide currently used as a thrombin inhibitor, in Salinispora pacifica. Their structures were determined using an integrated approach consisting of: (1) HPLC-UV-Vis-QToF-MS analysis with multimode ionization (ESI and APCI) and fast polarity switching; (2) database searching and matching of monoisotopic masses, retention times, mass spectra of the precursor and product ions of the compounds of interest and the authentic reference standards thereof.
Composition of the Essential Oil of Wild Grown Caraway in Meadows of the Vienna Region (Austria)
Authors: Chizzola Remigius
Published: March 2019

The essential oil compositions of the different plant parts of wild growing caraway (Carum carvi, Apiaceae) were analyzed by GC/MS and GC/FID. The plants came from two meadows in the Vienna region, Austria. The oils from young fruits had a high proportion of limonene (61-83%), and those from inflorescences limonene (39-62%) and germacrene D (23-41%). The carvone contents of fruits, inflorescences and leaves varied greatly. Leaves and stems, low in volatiles, were dominated by germacrene D and germacrene A. Therefore, wild caraway appears as a valuable aromatic herb in meadows.
Shoot Accumulation Kinetics and Effects on Herbivores of the Wound-Induced Antioxidant Indole Alkaloid Brachycerine of Psychotria brachyceras
Authors: Porto Diogo D. , Matsuura Hélio N. , Vargas Lúcia R. B. , Henriques Amélia T. , Fett-Neto Arthur G.
Published: March 2019

A major shoot-specific monoterpene indole alkaloid produced by Psychotria brachyceras, brachycerine, is regulated by either wounding or jasmonate application. Highest concentrations of the alkaloid are found in inflorescences, suggesting a defence role. Brachycerine has antimutagenic and antioxidant properties, capable of quenching singlet oxygen, hydroxyl radical, and superoxide. This study aimed at characterizing the putative role of brachycerine in P. brachyceras responses to wounding and herbivory. Damage to leaves increased the content of brachycerine locally. Wounding did not affect phenolics content in P. brachyceras leaves, and no tannins were detected in the species. In generalist herbivore bioassays, neither brachycerine nor P. brachyceras extracts showed toxic effects. In vivo hydrogen peroxide staining assay showed less wound-generated peroxide accumulation in alkaloid treated tissues. This pattern was confirmed in quantitative assays measuring tissue hydrogen peroxide concentrations. Data indicate that brachycerine is not a herbivore deterrent, but rather an indirect chemical defence, modulating oxidative stress caused by mechanical damage.
Glycosylation of Quercetin with Cultured Plant Cells and Cyclodextrin Glucanotransferase
Authors: Shimoda Kei , Kubota Naoji , Hamada Manabu , Uesugi Daisuke , Tanigawa Masato , Hamada Hatsuyuki , Hamada Hiroki
Published: March 2019

Quercetin was glucosylated by cultured plant cells of Ipomoea batatas to its 3- and 7- O-β-D-glucosides, and 3,7- O-β-D-diglucoside. On the other hand, further glycosylation of quercetin 3-O-β-D-glucoside by cyclodextrin glucanotransferase gave the 3-O-β-maltoside, 3-O-β-maltotrioside, and 3-O-β-maltotetraosides of quercetin.
Hedyotis diffusa Water Extract Diminished the Cytotoxic Effects of Chemotherapy Drugs against Human Breast Cancer MCF7 Cells
Authors: Dong Qiulin , Ling Binbing , Gao Bosong , Maley Jason , Sammynaiken Ramaswami , Yang Jian
Published: March 2019

Hedyotis diffusa is a Chinese herbal medicine widely used in combination with other herbal medicines such as Scutellaria barbata to treat various types of cancer. Late-stage and recurrent cancer patients usually use H. diffusa during chemotherapy in expecting to achieve additive or synergistic therapeutic effects. Several classes of active ingredients, including anthraquinones, iridoid glucosides and stigmasterols, have been isolated and characterized from H. diffusa. In the current study, we isolated alkaloid/flavonoid from H. diffusa and showed that the crude alkaloid/flavonoid extract rather than its three major components possessed antitumor activity against human breast cancer cell line MCF7. Co-administration of H. diffusa water extract diminished the cytotoxicities of chemotherapy drugs doxorubicin, cyclophosphamide and docetaxel towards the MCF7 cells, implicating that H. diffusa should not be used during breast cancer chemotherapy.
Composition and Chemical Variability of Eucalyptus bosistoana Essential Oil from Algerian Sahara
Authors: Bouzabata Amel , Bighelli Ange , Abed Lahouari , Casanova Joseph , Tomi Félix
Published: March 2019

The composition of eight oil samples isolated from leaves of Eucalyptus bosistoana F. Muell., acclimatized in Tamanrasset (southern Algeria, Saharan climate), has been investigated by GC (retention indices), GC-MS and 13C NMR spectroscopy. Two groups may be distinguished. The five samples of group I have their composition dominated by p-cymene (32.0-39.5%), cryptone (11.5-15.6%), 1,8-cineole (7.8-10.5%) and spathulenol (6.8-16.5%). The three oil samples of group II contained mainly 1,8-cineole (55.3-63.9%) and α-pinene (11.6-12.1%).
Volatile Constituents of Melissa officinalis Leaves Determined by Plant Age
Authors: Nurzyńska-Wierdak Renata , Bogucka-Kocka Anna , Szymczak Grażyna
Published: March 2019

The present study investigated changes in the content and chemical composition of the essential oil extracted by hydrodistillation from air-dried Melissa officinalis L. (lemon balm) leaves in the first and second year of plant growth. The lemon balm oil was analysed by GC-MS and GC-FID. The presence of 106 compounds, representing 100% of the oil constituents, was determined in the oil. The predominant components were geranial (45.2% and 45.1%) and neral (32.8% and 33.8%); their proportions in the examined samples of the oil obtained from one- and two-year-old plants were comparable. However, the age of lemon balm plants affected the concentration of other constituents and the proportions of the following compounds were subject to especially high fluctuations: citronellal (8.7% and 0.4%), geraniol (trace amounts and 0.6%), and geranyl acetate (0.5% and 3.0%), as well as, among others, isogeranial, E-caryophyllene, caryophyllene oxide, germacrene D, and carvacrol. The essential oil of two-year-old plants was characterized by a richer chemical composition than the oil from younger plants.
Antimicrobial Activity of Ammodaucus leucotrichus Fruit Oil from Algerian Sahara
Authors: El-Haci Imad Abdelhamid , Bekhechi Chahrazed , Atik-Bekkara Fewzia , Mazari Wissame , Gherib Mohamed , Bighelli Ange , Casanova Joseph , Tomi Félix
Published: March 2019

Three fruit oil samples of Ammodaucus leucotrichus Cosson & Durieu from Algerian Sahara were obtained by hydrodistillation and analyzed by GC(RI), GC-MS and 13C NMR spectroscopy. The main compounds were perillaldehyde (87.0-87.9%) and limonene (7.4-8.2%). The antimicrobial effect of the essential oil was evaluated against bacteria, yeasts and filamentous fungi. High antibacterial activity was observed against Escherichia coli, Staphylococcus aureus, Enterobacter cloaceae, Bacillus cereus and Salmonella typhimurium, with MIC values between 0.5-1.0 μL/mL. Fungal strains were also sensitive to the essential oil (MIC values: 0.25-0.75 μL/mL). The most potent activity was observed against the filamentous fungi, Fusarium oxysporum and Aspergillus flavus (0.25-0.50 μL/mL).
Chemical Composition and Termiticidal Activity of Essential Oils from Different Tissues of Chinese Cedar (Cryptomeria fortunei)
Authors: Xie Yongjian , Li Mang , Huang Qiuying , Lei Chaoliang
Published: March 2019

In this study antitermitic activities of essential oils from different tissues of Chinese cedar (Cryptomeria fortunei Hooibrenk) against Reticulitermes chinensis were investigated. In addition, the yields of essential oils obtained by water distillation were compared and their constituents determined by GC-MS analyses. The yields of bark, sapwood, heartwood, and leaf essential oils of Chinese cedar were 0.9, 0.4, 1.0, and 1.5%, respectively. GC-MS analyses showed that the major compounds of bark, sapwood, heartwood, and leaf essential oils of Chinese cedar were ferruginol (30.6%), γ-cadinene (18.3%), γ-cadinene (31.0%), and kaurene (30.6%), respectively. Bioactivity tests against R. chinensis demonstrated that the leaf and heartwood essential oils had an excellent effect, and the LC50 values after 5 days were 0.9 and 1.8 μL/mL (LC90=1.4 and 2.9 μL/mL), respectively. The results of this study showed that the leaf and heartwood essential oils of Chinese cedar might be considered as a potential source of a fine natural termiticide.
Chemical Composition and Anti-inflammation Activity of Essential Oils from Citrus unshiu Flower
Authors: Kim Min-Jin , Yang Kyong-Wol , Kim Sang Suk , Park Suk Man , Park Kyung Jin , Kim Kwang Sik , Choi Young Hun , Cho Kwang Keun , Hyun Chang-Gu
Published: March 2019

Though many essential oils from citrus peels are claimed to have several medicinal functions, the chemical composition and biological activities of the essential oils of Citrus flowers have not been well described. Therefore, this study intended to investigate the chemical composition and anti-inflammatory potential of essential oils from C. unshiu flower (CEO) to support its purported beneficial health effects. The chemical constituents of the CEO, analyzed by gas chromatography-mass spectrometry (GC-MS), included γ-terpinene (24.7%), 2-β-pinene (16.6%), 1-methyl-2-isopropylbenzene (11.5%), L-limonene (5.7%), β-ocimene (5.6%), and α-pinene (4.7%). The effects of the CEO on nitric oxide (NO) and prostaglandin E2 (PGE2) production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages were also examined. The results indicate that the CEO is an effective inhibitor of LPS-induced NO and PGE2 production in RAW 264.7 cells. Additionally, CEO was shown to suppress the production of inflammatory cytokines including interleukin (IL)-1β, tumor necrosis factor (TNF)-α, and IL-6. Based on these results, CEO may be considered a potential anti-inflammatory candidate with human health benefits.
Composition, Antioxidant and Antimicrobial Activities of Methanol Extracts of Some Acinos Miller Species
Authors: Golubović Tatjana , Palić Radosav , Kitić Dušanka , Stojanović Gordana , Zlatković Bojan , Ristić Mihailo , Pavlović Dragana
Published: March 2019

GC and GC/MS analyses of the methanol extracts obtained from the aerial parts of six Acinos Miller species from Serbia and Montenegro were performed. Seventy-four constituents, accounting for 84.9-99.0% of the total composition of the extracts, were identified. The common feature of the A. suaveolens, A. majoranifolius and A. alpinus methanol extracts was the high content of monoterpenes, while the common feature of the A. graveolens, A. arvensis and A. hungaricus methanol extracts was the prevalence of sesquiterpenes. The total flavonoids, polyphenols and tannins content, as well as antioxidant activity (FRAP and DPPH assay) of the methanolic extracts were investigated. The highest antioxidant activity was observed in the extract of A. alpinus which had high levels of all polyphenol classes examined. A disk diffusion method was used for the evaluation of the antimicrobial activities of the extracts against a panel of microorganisms (bacteria: Bacillus subtilis, Clostridium pyogenes, Enterococcus sp., Micrococcus flavus, Sarcina lutea, Staphylococcus aureus, Klebsiella pneumoniae, Proteus vulgaris, Pseudomonas aeruginosa, Salmonella enteritidis and Escherichia coli; fungi: Aspergillus niger, Candida albicans and Saccharomyces cerevisiae). The preliminary bioassay results indicated that the methanol extract of A. alpinus could be a possible source of antioxidant and antimicrobial compounds.
A New Source of (R)-Limonene and Rotundifolone from Leaves of Lippia pedunculosa (Verbenaceae) and their Trypanocidal Properties
Authors: Menezes Leociley Rocha Alencar , Santos Nilmara Nunes , Meira Cássio Santana , dos Santos Jamyle Andrade Ferreira , Guimarães Elisalva Teixeira , Soares Milena Botelho Pereira , Nepel Angelita , Barison Andersson , Costa Emmanoel Vilaça
Published: March 2019

Investigation by GC-FID and GC-MS of the essential oil (LPOE) from the leaves of Lippia pedunculosa revealed, as the major compounds, the monoterpenes rotundifolone (71.7%) and ( R)-limonene (21.8%). These two compounds and the minor constituent piperitenone (1.2%) were also isolated from the leaves and identified by spectrometric analysis. LPOE and isolated compounds were evaluated for their trypanocidal activity against epimastigote and trypomastigote forms of Trypanosoma cruzi. Significant results with IC50 values lower than 34.0 μg.mL−1 were observed against these forms of T. cruzi for LPOE and isolated compounds. Rotundifolone was the most active compound with an IC50 lower than 10.0 μg.mL–1 for both forms of T. cruzi. The effects of LPOE and isolated compounds were also evaluated in cultures of macrophages infected with T. cruzi. Treatment with ( R)-limonene and rotundifolone caused a moderate reduction in the percentage of macrophages infected by T. cruzi and in the number of intracellular parasites at concentrations non-toxic to macrophages.
Scalarane Sesterterpenes from the Paracel Islands Marine Sponge Hyrtios sp
Authors: Yang Fan , Gan Jian-Hong , Liu Xiao-Yan , Lin Hou-Wen
Published: March 2019

A new scalarane sesterterpene, sesterstamide (1), together with four known sesterterpenes (2–5), were isolated from the Paracel Islands marine sponge Hyrtios sp. The chemical structures were established on the basis of spectroscopic analysis and comparison with known compounds. The cytotoxic and antileishmanial activities of the isolated compounds were also evaluated.
Ring a Conformation of Aconine and Pseudaconine in CDCl3
Authors: Deng Hong-Ying , Chen Qiao-Hong , Wang Feng-Peng
Published: March 2019

On the basis of intensive interpretation of the 1H NMR spectroscopic data, the ring A conformation of aconine (1) was speculated as twist boat in CDCl3, and as chair or twist boat in acetone-d6 and pyridine-d5. The ring A of pseudaconine (2) adopts the chair conformation in CDCl3, acetone- d6, and pyridine- d5. Accordingly, the boat conformation of ring A in these two diterpenoid alkaloids in CDCl3 reported in the literature [1] should be revised. The difference in 13C NMR data for the same compound (1 or 2) in two different solvents (CDCl3, pyridine- d5) can be attributed to solvent effects.
Structure Revision of N-Mercapto-4-formylcarbostyril Produced by Pseudomonas fluorescens G308 to 2-(2-Hydroxyphenyl)thiazole-4-carbaldehyde [aeruginaldehyde]
Authors: Ye Lumeng , Cornelis Pierre , Guillemyn Karel , Ballet Steven , Christophersen Carsten , Hammerich Ole
Published: March 2019

An antibiotic substance isolated from Pseudomonas fluorescens strain G308 was earlier assigned the structure of N-mercapto-4-formylcarbostyril, but computational predictions of the 1H and 13C NMR magnetic shielding tensors show this structure to be incompatible with the published spectroscopic data. The same is true for six quinoline derivatives related to N-mercapto-4-formylcarbostyril by permutation of the O and S atoms. In contrast, 2-(2-hydroxyphenyl)thiazole-4-carbaldehyde [aeruginaldehyde], isolated from Pseudomonas protegens Pf-5, together with the reduced derivative aeruginol, displays spectroscopic data identical with those of the alleged carbostyril derivative. In addition, the published 1H and 13C NMR data are in agreement with those calculated for aeruginaldehyde. We propose that aeruginaldehyde and aeruginol originate from the non-ribosomal peptide synthetase enzymes involved in the siderophores enantio-pyochelin (or pyochelin) biosynthetic pathways.
Overexpression of Cinnamate 4-Hydroxylase and 4-Coumaroyl CoA Ligase Prompted Flavone Accumulation in Scutellaria baicalensis Hairy Roots
Authors: Kim Young Seon , Kim Yeon Bok , Kim YeJi , Lee Mi Young , Park Sang Un
Published: March 2019

Scutellaria baicalensis Georgi, a species of the Lamiaceae family, is considered as one of the 50 fundamental herbs used in traditional Chinese medicine. In order to enhance flavone (baicalein, baicalin, and wogonin) content in S. baicalensis roots, we overexpressed a single gene of cinnamate 4-hydroxylase (C4H) and 4-coumaroyl coenzyme A ligase (4CL) using an Agrobacterium rhizogenes-mediated system. SbC4H- and Sb4CL-overexpressed hairy root lines enhanced the transcript levels of SbC4H and Sb4CL compared with those in the control and also increased flavones contents by approximately 3- and 2.5-fold, respectively. We successfully engineered the flavone biosynthesis pathway for the production of beneficial flavones in S. baicalensis hairy roots. The importance of upstream gene C4H and 4CL in flavone biosynthesis and the efficiency of metabolic engineering in promoting flavone biosynthesis in S. baicalensis hairy roots have been indicated in this study.
New Isoflavone Glycosides from the Stems of Dalbergia vietnamensis
Authors: Loan Pham Thanh , Anh Hoang Le Tuan , Cuc Nguyen Thi , Yen Duong Thi Hai , Hang Dan Thi Thuy , Ha Tran Minh , Nhiem Nguyen Xuan , Van Du Nguyen , Thai Tran Huy , Van Minh Chau , Van Kiem Phan
Published: March 2019

Two new isoflavone glycosides, dalspinosin 7- O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (1) and caviunin 7- O-(5- O-trans-p-coumaroyl)-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (2), and two known compounds, caviunin 7- O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (3) and caviunin (4) were isolated from the stems of Dalbergia vietnamensis. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D- and 2D-NMR spectroscopy, as well as by comparing with the NMR data reported in the literature.
A Characterization of Content, Composition and Scavenging Capacity of Phenolic Compounds in Parsnip Roots of Various Weight
Authors: Nikolić Nada Č. , Lazić Miodrag M. , Karabegović Ivana T. , Stojanović Gordana S. , Todorović Zoran B.
Published: March 2019

The contents, composition and radical scavenging capacity of phenolic compounds from parsnips of various root weights grown in Serbia were examined. The content of phenolic compounds depended on root size, and the highest content was in the group where the samples with the lowest root size were grouped. The content of phenolic compounds varied from 109.7 to 125.3 μmol of chlorogenic acid per g dry extract, i.e.5470.8 to 6245.1 mg per kg fresh weight. Among the identified compounds were quercetin, kaempferol, apigenin and genkwanin glucosides and hydroxycinnamic and caffeoylshikimic acids. The highest antioxidant capacity was found for the group with the lowest root weight; the IC50 values ranged from 1.59 to 2.49 mg mL–1. There was positive correlation between the total phenolic content and scavenging capacity, and the kaempferol glucosides content could be an indicator of DPPH scavenging capacity of parsnip roots.
Oxirapentyns A, B and E from the Marine-Derived Strain of Isaria felina KMM 4639 as Stimulators of Initial Stages of Development of Agricultural Plants
Authors: Anisimov Mikhail M. , Chaikina Elena L. , Smetanina Olga F. , Afiyatullov Shamil Sh.
Published: March 2019

Oxirapentyn A (1), oxirapentyn B (2), and oxirapentyn E (3) were examined for their ability to stimulate growth of seedling roots of barley ( Hordeum vulgare L.), buckwheat ( Fagopyrum esculentum Moench), corn ( Zea mays L.), soy { Glycine max (L.) Merr.}, and wheat ( Triticum aestivum L.). It was shown that the stimulatory effects depend on the chemical structure of the oxirapentyns and on the plant species. Compounds 1, and 2 are efficient for growth of seedling roots of barley, and wheat, whereas compound 3, at different concentrations, stimulates growth of seedling roots of maize, soy, and wheat. These compounds can be recommended for field study as plant growth stimulators.
Methodology for Porphyrin Isolation by High-Performance Countercurrent Chromatography
Authors: Ramos Amaro C. , Neves Fernanda S. , Vega Maria Raquel G. , Maria Edmilson J. , Oliveira’ Rodrigo R.
Published: March 2019

Countercurrent chromatography is a versatile technique for the isolation of a wide variety of plant substances. However, little attention has been devoted to the application of this technique for the isolation of porphyrins. This class of compounds are of great importance in the medical area and in photocatalysis due to their heterocyclic structure, composed of four modified pyrrol subunits interconnected on their α carbon atoms by methinic bridges. The methanol extract of Gallesia integrifolia was partitioned using different solvents; the dichloromethane fraction was then submitted to countercurrent chromatography. The solvent system composed of n-hexane, ethyl acetate, methanol, and water (1:2.5:2.5:1) was chosen to perform the chromatographic analysis due to the enhanced solubility and the best distribution coefficients of the target compounds. Two porphyrins were isolated by this method and identified as 132-hydroxypheophorbide a methyl ester and pheophorbide a, methyl ester. The solvent system proposed provided good distribution coefficients for both substances (1.27 and 1.87, respectively), and a high resolution factor.
Chemical Composition, and Cytotoxic, Antioxidant and Antibacterial Activities of the Essential Oil from Ginseng Leaves
Authors: Jiang Rui , Sun Liwei , Wang Yanbing , Liu Jianzeng , Liu Xiaodan , Feng Hao , Zhao Daqing
Published: March 2019

Panax ginseng C.A.Meyer is one of the most valuable traditional Chinese medicines. In this study, the essential oil of ginseng leaves (EOGL), collected using hydrodistillation and analyzed by GC/MS, contained a complex mixture of aliphatic (69.0%), terpenoid (21.5%) and aromatic compounds (2.4%). Among 54 components identified, the major ones were palmitic acid (36.1%), β-farnesene (15.4%), linoleic acid (9.8%) and phytol (5.6%). In the cytotoxicity study, EOGL exhibited obvious cytotoxic activities against different cancer cell lines, including Hela, A549, ZR-75-1, HT-29, SGC7901 and B16 cells. Furthermore, Annexin V-FITC/PI staining assay indicated that EOGL can induce late apoptosis of ZR-75-1 cells, and the percentage of apoptotic cells increased in a concentration-dependent manner (0.9% to 5.6% and 67.4%). In addition to this, we also found that EOGL exhibited weak DPPH radical scavenging (12.0 ± 0.4 mg/mL) and ABTS radical scavenging activities (1.6 ± 0.1 mg/mL), and showed antibacterial activity against the Gram-positive bacteria, Staphylococcus aureus and Bacillus subtilis, and the Gram-negative bacterium, Escherichia coli. The data suggest that EOGL, which possesses important biological activities, especially significant anticancer activity, could be a potential medicinal resource.
Accumulation of Silicon in Cacti Native to the United States: Characterization of Silica Bodies and Cyclic Oligosiloxanes in Stenocereus thurberi, Opuntia littoralis, Opuntia ficus-indica, and Opuntia stricta
Authors: Wright Cynthia R. , Waddell Emanuel A. , Setzer William N.
Published: March 2019

Four different cactus species growing in the United States, Stenocereus thurberi growing in Organ Pipe Cactus National Monument, Arizona, Opuntia littoralis and Opuntia ficus-indica, growing on Santa Catalina Island, California, and Opuntia stricta, growing in northern Alabama, were examined for the presence of silica bodies (opaline phytoliths). Silica bodies were found in all four of these cactus species, parallelepiped-shaped crystals in S. thurberi, and starburst-shaped crystalline structures in the three Opuntia species. In addition, the essential oils of the four cactus species were obtained by hydrodistillation and analyzed by gas chromatography – mass spectrometry. To our surprise, S. thurberi, O. littoralis, and O. ficus-indica (but not O. stricta) essential oils contained cyclic oligosiloxanes. To our knowledge, cyclic oligosiloxanes have not been previously found as essential oil components.
Antifeedant and Phagostimulant Activity of Extracts and Pure Compounds from Hymenoxys robusta on Spodoptera exigua (Lepidoptera: Noctuidae) Larvae
Authors: Juárez Zaida N. , Fortuna Antonio M. , Sánchez-Arreola Eugenio , López-Olguín Jesús F. , Bach Horacio , Hernández Luis R.
Published: March 2019

In this study, the insecticidal and antifeedant activities of compounds from the leaves of Hymenoxys robusta on Spodoptera exigua, also known as armyworm, are reported. The methanol extract possessed suppressive activity, as well as a high antifeedant activity, suggesting that this extract has toxic effects on larvae. Compounds isolated from the plant show that a derivative of inositol and hymenolides stimulate the feeding, while vermeerin shows a high antifeedant effect. In addition, the methanol extract inhibited oviposition, whereas consumption of the n-hexane extract and hymenolides produced infertile eggs. These findings suggest that compounds extracted from H. robusta have potential for the development of products for pest control.
Theoretical Research into Anticancer Activity of Diterpenes Isolated from the Paraiban Flora
Authors: Scotti Luciana , Ishiki Hamilton , Junior Francisco J.B. Mendonça , Santos Paula F. , Tavares Josean F. , Silva Marcelo S. , Scotti Marcus T.
Published: March 2019

Many studies of the scientific literature discuss the anticancer activity of diterpenes inhibiting the Akt/IKK/NF-κB pro-survival signaling cascade, mainly by the activation of serine/threonine phosphatase PP2A. The aim of this work was to evaluate and compare the anticancer potential of three atisane, three kaurane and three trachylobane diterpenes extracted from the roots of Xylopia langsdorffiana. Thus, we investigated the reactivity (H-LGAP parameter), HOMO atmosphere favorable to neutralize the radical reactivity, and the docking of compounds with PP2A. With all approaches, this theoretical study showed that atisane diterpenes have favorable characteristics for antitumor activity, like electron donating ability and greater hydrophilic interactions with the enzyme, by inhibition of Akt/IKK/NF-κB, and activation of PP2A.
Seed Dormancy Breaking Diterpenoids from the Liverwort Plagiochila sciophila and their Differentiation Inducing Activity in Human Promyelocytic Leukemia HL-60 Cells
Authors: Kenmoku Hiromichi , Tada Hiroyuki , Oogushi Megumi , Esumi Tomoyuki , Takahashi Hironobu , Noji Masaaki , Sassa Takeshi , Toyota Masao , Asakawa Yoshinori
Published: March 2019

To obtain the structural diversity of bioactive compounds similar to cotylenins and fusicoccins that modulate 14-3-3 protein-protein interactions in eukaryotes, screening tests were carried out using the lettuce seed dormancy breaking-assay. An acetone extract of the liverwort Plagiochila sciophila exhibited significant activity against the seeds in the presence of the plant hormone abscisic acid. Activity-guided fractionation of the extract afforded the isolation of seven novel fusicoccane-type diterpenoids, named fusicosciophins A-E (1–5), 8-deacetyl (6) and 9-deacetyl fusicosciophin E (7). Their structures were determined by spectroscopic methods and X-ray crystallographic analyses. All the pure isolated compounds (1–7) exhibited moderate lettuce seed dormancy breaking activity. In addition, the differentiation-inducing activity and cytotoxicity of these isolates, together with fusicoccin A (FC-A) and all- trans retinoic acid (ATRA), were evaluated in human promyelocytic leukemia HL-60 cells and human mouth epidermal carcinoma KB cells, respectively. Fusicosciophins (2 and 4) and FC-A exhibited moderate differentiation-inducing activity (EC50 31.2~59.1μM) compared with ATRA (EC50 0.3μM), while 2, 4 and ATRA exhibited higher selectivity indices (IC50/EC50 >3.38~667) than FC-A (IC50/EC50 1.05). This is the first report on the isolation of fusicoccane-type diterpenoids from liverworts having seed dormancy breaking activity and differentiation-inducing activity in mammal cells.
Synthetic and Structure-Activity Relationship of Insecticidal Bufadienolides
Authors: Hidayat Ace Tatang , Zainuddin Achmad , Dono Danar , Hermawan Wawan , Hayashi Hideo , Supratman Unang
Published: March 2019

A new synthetic analog of bufadienolide, methyl isobryophyllinate A (1), and a known synthetic analog, methyl isobersaldegenate-1,3,5-orthoacetate (2), were obtained by methanolysis of bryophyllin A (3) and bersaldegenin-1,3,5-orthoacetate (5) in basic solution. Structure-insecticidal activity relationship studies revealed both orthoacetate and α-pyrone moieties seemed to be essential structural elements for exhibiting insecticidal activity, whereas oxygenated substituents in the C ring enhanced the insecticidal activity against the third instar larvae of silkworm (Bombyx mori).
Rare Prenylated Isoflavones from Tephrosia calophylla
Authors: Ganapaty Seru , Nair Vimal , Devi Devarakonda Rama , Pannakal Steve Thomas , Laatsch Hartmut , Dittrich Birger
Published: March 2019

Chemical re-examination of the roots of T. calophylla led to the isolation of four isoflavones, namely 2′,4′,5-trihydroxy-6,7-(2″,2″-dimethylchromene)-8-γ,γ-dimethylallylisoflavone (1a, auriculatin), 2′,5-dihydroxy-6,7-(2″,2″-dimethylchromene)-4′-γ,γ-dimethylallyloxyisoflavone (2a, isoauriculatin), 3′,4′,5-trihy-droxy-6,7-(2″,2″-dimethylchromene)-8-γ,γ-dimethylallylisoflavone (1b, auriculasin), and 3′,5-dihydroxy-6,7-(2″,2″-dimethylchromene)-4′-γ,γ-dimethylallyl-oxyisoflavone (2b, isoauriculasin). Auriculasin and isoauriculasin are reported for the first time with full NMR assignments. All metabolites were fully characterized by 1D and 2D NMR techniques including COSY, HSQC, HMBC experiments, mass spectra and in part on the basis of X-ray diffraction. Accurate ‘invariom’ refinements with aspherical scattering factors were carried out for 1a, 1b and 2a.
Synthesis and Biological Evaluation of Oseltamivir Analogues from Shikimic Acid
Authors: Nguyen Van Hung , Pham Van Cuong , Do Thi Thao , Mai Huong Doan Thi , Le Nguyen Thanh , Vu Van Nam , Tran Van Hieu , Nguyen Thi Minh Hang , Dehaen Wim , Chau Van Minh
Published: March 2019

New oseltamivir analogues were designed and synthesized, starting from shikimic acid. Biological evaluation against three human cancer cell lines (KB, MCF7 and Lu-1) showed that many of them exhibited cytotoxic activity. Azides 5 are more active than the corresponding amines 6. Thus, the reduction of the azide group into amine led to the loss of cytotoxicity. The compounds with a cyclohexanemethyloxy group at C-3 were more active than the other investigated compounds belonging to the same series. This cyclohexanemethyloxy group seems to be critical for the cytotoxic activity of this class of compounds. The synthetic oseltamivir analogues 6a-e had no inhibition activity, even at the concentration of 50 μM when they were evaluated for their in vitro influenza A neuraminidase inhibitory activity by an enzymatic assay.
PPZPMs - a Novel Group of Cyclic Lipodepsipeptides Produced by the Phytophthora alni Associated Strain Pseudomonas sp. JX090307 -the Missing Link between the Viscosin and Amphisin Group
Authors: Weißhoff Hardy , Hentschel Sarah , Zaspel Irmtraut , Jarling René , Krause Eberhard , Pham Thi Lam Huong
Published: March 2019

The closely related to the Pseudomonas orientalis strain Pseudomonas sp. acc. no. JX090307 was isolated from hyphae of the phytopathogenic oomycete Phytophthora alni spp. alni. In in-vitro antagonistic tests, the living bacterium JX090307 and its cell extract showed antibiosis activity against different fungal pathogens of forest tree species, particularly against Verticillium dahliae and some strains of P. alni ssp. alni. Investigating the cell extract of JX090307 by means of LC-ESI-Q-TOF-MS and -MS/MS techniques, more than 30 cyclic lipodepsipeptids (CLPs) were found. 24 of them belong to a novel group of CLPs named PPZPM. The cyclic lipodepsidecapeptides PPZPMs are composed of a β-hydroxy fatty acid linked to a peptide part comprising 10 amino acids, where 8 of them are organized in a cyclic structure. PPZPMs differ from members of the Viscosin and Amphisin group by the number of amino acids forming the cyclic structure. The two main components, PPZPM-1a and PPZPM-2a, were investigated additionally by means of NMR spectroscopy.
Chemical Composition of Vernonia albicans Essential Oil from India
Authors: Joshi Rajesh K.
Published: March 2019

The chemical composition of the hydro-distilled essential oil obtained from the flowering aerial parts of Vernonia albicans DC. (Asteraceae) was analyzed by gas chromatography equipped with a flame ionization detector (GC-FID) and gas chromatography coupled with a mass spectrometry (GC/MS). Thirty-nine compounds have been identified, representing 97.5% of the total oil. The major constituents were β-caryophyllene (34.3%), γ-amorphene (19.5%), 9-epi-β-caryophyllene (6.9%), and α-pinene (6.9%). The oil was found to be rich in sesquiterpene hydrocarbons (73.9%).
Chemical Composition and Biological Activities of the Essential Oil from Anredera cordifolia 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 oil of Anredera cordifolia (Ten.) Steenis (Basellaceae), grown in Brazil, was studied by means of GC and GC-MS analysis. In all, 19 compounds were identified, accounting for 91.6% of the total oil; hydrocarbons were the main constituents (67.7%). The essential oil was evaluated for its in vitro potential phytotoxic activity against germination and initial radicle growth of Raphanus sativus L., Sinapis arvensis L., and Phalaris canariensis L. seeds. At 1.25 μg/mL and 0.625 μg/mL, the oil significantly promoted the germination of S. arvensis. Moreover, the antimicrobial activity of the essential oil was assayed against ten bacterial strains. The essential oil showed a weak inhibitory activity against the Gram-positive pathogens.
Profile of Volatile Components of Hydrodistilled and Extracted Leaves of Jacaranda acutifolia and their Antimicrobial Activity Against Foodborne Pathogens
Authors: Singab Abdel Nasser B. , Mostafa Nada M. , Eldahshan Omayma A. , Ashour Mohamed L. , Wink Michael
Published: March 2019

Volatile constituents of the essential oil and n-hexane extract of Jacaranda acutifolia Humb. and Bonpl. (Bignoniaceae) leaves were determined, and their antimicrobial activities were investigated using an agar diffusion method. The minimum inhibitory concentrations (MIC) were determined and compared with those of standard antibiotics (penicillin, gentamicin and nystatin). The chemical composition of the oils was analyzed by capillary gas chromatography (GLC-FID) and gas chromatography–mass spectrometry (GLC-MS). Thirty-four components, comprising almost 93.8% of the total peak area, were identified in the leaf essential oil. The main components were methyl linolenate (26.7%), 1-octen-3-ol (10.8%), methyl phenyl acetate (9.9%), β-linalool (5.5%) and palmitic acid (4.7%). The n-hexane extract revealed similar oil constituents, but also p-benzoquinone, phenyl acetic acid, resorcinol and homogentisic acid. The oil showed some activity against Staphylococcus aureus and Escherichia coli with MIC values of 2.2 and 2.9 mg/mL, respectively, and moderate activity against Candida albicans, Salmonella typhimurium and Shigella flexneri. The n-hexane extract showed moderate activities against all tested microorganisms, with MIC values ranging from 3.5 to 10.2 mg/mL. The antimicrobial activities of the hydrodistilled and extracted leaves make their local traditional uses rational.
Bioactive Secondary Metabolites from Acid Mine Waste Extremophiles
Authors: Stierle Andrea A. , Stierle Donald B.
Published: March 2019

The extremophilic microbes of the Berkeley Pit Lake are a valuable source of new and interesting secondary metabolites. It is of particular interest that these acidophilic microbes produce small molecule inhibitors of pathways associated with low pH and high Eh. These same small molecules also inhibit molecular pathways induced by reactive oxygen species (ROS) and inflammation in mammalian cells. Low pH is a hallmark of inflammation and high Eh is one of ROS, so the suitability of this collection as a source of bioactive metabolites is actually quite biorational. Compound isolation was guided by inhibition of caspase-1 and matrix metalloproteinase-3, and active compounds were sent to the National Cancer Institute-Developmental Therapeutics Program and Memorial Sloan Kettering Cancer center for evaluation as either antiproliferative or cytotoxic agents.
Microbial Transformation of the Diterpene 7-epi-Foliol by Fusarium fujikuroi
Authors: Fraga Braulio M. , Bressa Carlo , González Pedro , Guillermo Ricardo
Published: March 2019

The incubation of 3α,7α,18-trihydroxy- ent-kaur-16-ene (7- epi-foliol) with the fungus Fusarium fujikuroi gave 3α,7α,18-trihydroxy- ent-kaur-16-en-18-al as the sole product. The biotransformation of other 7α- or 7β-hydroxy derivatives had led to the oxidation of C-19, which is a main step in the biosynthesis of gibberellins and kaurenolides. Now, the presence of the 3a-hydroxyl impedes that oxidation, which is directed to the adjacent C-18 hydroxymethyl forming the corresponding aldehyde.
Mechanistic Studies on the Intramolecular Cyclization of O-Tosyl Phytosphingosines to Jaspines
Authors: Crehuet Ramón , Mormeneo David , Anglada Josep M. , Delgado Antonio
Published: March 2019

A theoretical study to elucidate the mechanistic aspects involved in the tosylation-cyclization reaction of diastereomeric phytosphingosines 1a-1d to jaspines 4a-4d is presented. The stereochemistry of the starting stereoisomers is crucial for the development of weak interactions, both in the reactants and in the transition states. The analysis of the energy barriers of each elementary reaction is consistent with the observed reluctance of tosylate 2d to undergo cyclization. In addition, the initial tosylation can be identified as the limiting step in cyclizations from 1a and 1b.