bluuebunny/crossref_metadata_2025 huggingface dataset:
Preventive Effects of Resveratrol-enriched Extract of Peanut Sprout on Bacteria- and Estradiol-induced Prostatitis in Mice
Authors: Pyo Kyoung-Ho , Lee You-Won , Lee Sang-Hoon , Xin Chun-Feng , Shin Ji-Hun , Shin Eun-Hee
Published: March 2019

The present study investigated the effect of peanut sprout extract (PSE) as a natural resveratrol supplement on chronic bacterial prostatitis (CBP) and estradiol-induced benign prostatic hyperplasia (BPH). PSE contained a high level of resveratrol (148.51 ± 3.05 μg/g), and was tested on the mouse models of CBP (induced by Escherichia coli 292 infection) and BPH (induced by treatment with β-estradiol and dihydrotestosterone). PSE toxicity was assessed on the basis of changes in body weight, alanine aminotransferase activity (an indicator of hepatotoxicity), and expression of the kidney injury marker KIM-1. The effects of PSE on the histopathology of prostate tissue, the proportion of neutrophils, and immune cell profiles in the blood and spleen were examined. PSE administration did not result in any toxicity but reduced the bacterial burden and histopathological changes in the prostate. In addition, lymphocytes (CD4+, CD8+, and CD19+) in the spleen were significantly increased after PSE administration in CBP mice, suggesting immune enhancement. PSE treatment of bone marrow–derived macrophages increased the expression of CD40, which is related to the pro-inflammatory function and host defense against pathogens. It is concluded that PSE would be a good supplement for the mitigation of prostate hyperplasia and prostatitis.
Metabolites from Penicillium sp. Associated with Paris polyphylla
Authors: Li Xiao-Zhan , Ruan Bao-Hui , Yang Ya-Bin , Yang Xue-Qiong , Chen Guang-Yi , Hu Ming , Wang Bang-Yan , Zhou Hao , Ding Zhong-Tao
Published: March 2019

One new gentisyl alcohol derivative and seven known compounds were isolated from the culture of Penicillium sp. Their chemical structures were elucidated by extensive spectroscopic analysis. Compounds 1, 4, and 6 inhibited Bacillus subtilis, Staphylococcus aureus, and Escherichia coli with MICs of 32–128 μg/mL.
Phileucin - A Cyclic Dipeptide Similar to Phevalin (Aureusimine B) from Streptomyces coelicolor M1146
Authors: Böhringer Nils , Gütschow Michael , König Gabriele M. , Schäberle Till F.
Published: March 2019

Overexpression of a putative type III polyketide synthase (PKSIII) from the marine myxobacterium Enhygromyxa salina SWB007 in Streptomyces coelicolor M1146 led to the accumulation of a novel monoketopiperazine consisting of phenylalanine and isoleucine. This compound was named phileucin and shows high structural similarity to phevalin (aureusimine B). The protease inhibiting activity was tested against human cathepsin L, human leukocyte elastase, bovine trypsin and bovine chymotrypsin. In contrast to phevalin, no protease inhibition was observed.
LC/DAD/MSn and ICP-AES Assay and Correlations between Phenolic Compounds and Toxic Metals in Endemic Thymus alsarensis from the Thallium Enriched Allchar Locality
Authors: Stanoeva Jasmina Petreska , Stefova Marina , Andonovska Katerina Bačeva , Stafilov Trajče
Published: March 2019

Samples of Thymus alsarensis Ronniger, an endemic species for the Allchar locality, were evaluated for their polyphenolic composition and heavy metals. Allchar district is an abandoned antimony-arsenic-thallium deposit in the north-west of Kožuf Mountain, R. Macedonia, with a unique mineral composition affecting the mineral composition of the flora. A systematic method for phenolic compounds characterization was developed using mass spectrometry coupled to HPLC/DAD. Analyses were focused on the polyphenolic compounds to establish a possible correlation to the region specific heavy metals As and Tl in the different organs of T. alsarensis. Twenty-seven polyphenols: phenolic acid derivatives and flavonoid glycosides of luteolin, apigenin, quercetin, and kaempferol were detected; contents were higher in the leaves and flowers compared with stems and roots. Quinic acid (1), prolithospermic acid (6), salvianolic acid B (7), salvianolic acid A (8), monomethyl lithospermate (9), luteolin dihexoside (12), luteolin pentosyl-hexoside (14), luteolin acetyl pentosyl-hexoside (16), luteolin acetyl hexoside (17), luteolin dipentoside (21), luteolin pentoside (24), luteolin acetyl dipentoside (25), kaempferol pentosyl-hexoside (19) and kaempferol acetyl pentosyl-hexoside (22) were detected in T. alsarensis for the first time.

To assay the content of As and Tl, root, stem, leaf and flower samples were analyzed by inductively coupled plasma atomic emission spectrometry (ICP-AES). Significant accumulation of As and Tl was observed with As content from 0.25 to 140 mg/kg and Tl from 0.10 to 496 mg/kg. The content of As was much higher in the roots, while the content of Tl was significantly higher in the roots, flowers and leaves in all T. alsarensis specimens. Comparison of the results obtained for total polyphenols and for As and Tl content does not suggest any correlation (positive or negative) between the total phenolic content and the content of Tl and As. On the other hand, it is evident that the soil rich with specific heavy metals (Tl and As) affects the type of polyphenolic compounds produced in different organs, compared with other Thymus species growing on soil that is not contaminated.
Effect of Drought and Salinity on Volatile Organic Compounds and Other Secondary Metabolites of Citrus aurantium Leaves
Authors: Eirini Sarrou , Paschalina Chatzopoulou , Ioannis Therios , Kortessa Dimassi-Theriou
Published: March 2019

Research was carried out in order to evaluate the effect of drought and salinity on Citrus aurantium L. plant physiological characteristics, total phenolic, flavonoid and ascorbic acid contents, and volatile organic compounds. C. aurantium plants were exposed to different levels of drought and salinity for an experimental period of 60 days. Moderate water deficit (MWD) and 100 mM NaCl increased significantly leaf total phenolic, flavonoid and ascorbic acid contents. Both drought and salinity promoted the accumulation of essential oil in leaves, while MWD and 100 mM NaCl resulted in the highest concentrations of essential oil. The main compounds of the essential oil were linalool, linalyl acetate, neryl acetate, geranyl acetate and α-terpineol. MWD and severe water deficit (SWD) reduced the concentration of hydrocarbon monoterpenes and promoted the accumulation of oxygenated compounds, while treatment with 50 and 100 Mm NaCl, promoted the accumulation of hydrocarbon monoterpenes and reduced oxygenated monoterpene concentrations in C. aurantium.
Essential Oil Content, Composition and Bioactivity of Juniper Species in Wyoming, United States
Authors: Zheljazkov Valtcho D. , Astatkie Tess , Jeliazkova Ekaterina A. , Heidel Bonnie , Ciampa Lyn
Published: March 2019

The objective of this study was to evaluate variations in leaf essential oil (EO) content and composition of Juniperus species in the Bighorn Mountains { J. communis L. (common juniper), J. horizontalis Moench. (creeping juniper), and J. scopulorum Sarg. (Rocky Mountain juniper)} in Wyoming, USA. The EO was extracted via steam distillation of fresh leaves (needles). The EO composition of the three Juniper species varied widely. Overall, the essential oil content of fresh leaves was 1.0% (0.4–1.8% range in different accessions) in J. communis, 1.3% (1.2 to 1.6% range) in J. horizontalis, and 1.1% (0.7–1.5% range) in J. scopulorum. The EO chemical profile of J. communis was very different from that of the other two species. The concentration of α-pinene in the oil was 67–80% in J. communis, 2.8–6% in J. horizontalis, and 2.3–13% in J. scopulorum. The concentration of sabinene was 57–61% of the oil of J. horizontalis and 13–59% in oil of J. scopulorum, whereas sabinene was either below 1% or not detected in J. communis. The oils of J. scopulorum and J. horizontalis had higher antioxidant capacity than that of J. communis. The oils of the three junipers did not show significant antimicrobial activity against 10 organisms. The diversity of the essential oil composition of these three junipers may encourage diverse industrial applications of Juniperus leaf essential oil.
Gas Chromatography-Mass Spectrometry (GC-MS) Combined with Retention Index Prediction for the Rapid Identification of Halogenated monoterpenes from a Namibian Plocamium species
Authors: Louw Stefan , Kandjengo Lineekela , Knott Michael G.
Published: March 2019

Plocamium species collected from the Namibian coast display morphological features similar to those of both P. rigidum and P. suhrii which makes identification of these species a difficult task. It has been reported that the major secondary metabolites found in various Plocamium species are unique to each species [1]. In this study GC-MS combined with a retention index (RI) prediction strategy was used for the rapid identification of halogenated monoterpenes characteristic of a particular Namibian Plocamium species. The RIs of the metabolites were matched with the predicted RIs of halogenated monoterpenes for which similar MS data have been reported for the same species of Plocamium. Based on the identification of the major secondary metabolite, 1 E,3 R,4 S,5 E,7 Z-1-bromo-3,4,8- trichloro-7-(dichloromethyl)-3-methylocta-1,5,7-triene [2], it was proposed that these Namibian samples are closely related to that of P. suhrii. From this, it was determined that the proposed P. suhrii specimens collected in Namibia contain four additional metabolites (with molecular formulae C10H16Br2Cl2, C10H11BrCl4, C10H9BrCl6 and an unknown compound) previously not reported in P. suhrii species. In addition, a compound previously identified in South African P. suhrii was not present in the Namibian Plocamium specimens.
Triterpenes with Anti-invasive Activity from Sclerotia of Inonotus obliquus
Authors: Ryu Kaori , Nakamura Seikou , Nakashima Souichi , Aihara Masaaki , Fukaya Masashi , Iwami Junko , Asao Yasunobu , Yoshikawa Masayuki , Matsuda Hisashi
Published: March 2019

The methanolic extract [inhibition (%): 61.2±3.8 ( p<0.01) at 100 μg/mL] and its EtOAc-soluble fraction [inhibition (%): 82.5±1.7 ( p<0.01) at 100 μg/mL] from the sclerotia of Inonotus obliquus collected in Japan significantly inhibited invasion of human fibrosarcoma HT1080 cells through matrigel-coated filters. In addition, the methanolic extract significantly inhibited lung tumor formation fifteen days after injection of B16F10 melanoma cells in mice [inhibition (%) 66.1 ± 12.8 ( p < 0.05) at 500 mg/kg/d, p.o.]. Lanostane-type triterpenes were isolated as the common principal constituents from Japanese and Russian I. obliquus. Furthermore, we examine the inhibitory effects of the constituents on the invasion of HT 1080 cells. Interestingly, 3β-hydroxylanosta-8,24-dien-21-al [inhibition (%) 37.9 ± 3.0 ( p < 0.05) at 30 μM] significantly inhibited the invasion, and no cytotoxic effect at 30 μM was observed.
Synergistic Activity of Essential Oils from Herbs and Spices Used on Meat Products against Food Borne Pathogens
Authors: García-Díez Juan , Alheiro Joana , Pinto Ana Luisa , Falco Virgilio , Fraqueza Maria João , Patarata Luís
Published: March 2019

Essential oils (EOs) could be utilized as natural agents to improve the safety of meat products. However, the high concentration required to achieve an antimicrobial effect in foods might be incompatible with their sensory acceptance. To avoid this problem, combinations of EOs provide an effective approach reducing the odds of sensory rejection. In our study, 13 EOs of herbs and spices commonly used in the seasoning of meat products were assessed for their antimicrobial activity against Salmonella spp., Listeria monocytogenes, Escherichia coli and Staphylococcus aureus. However, only 7 of them were selected to study their synergistic effect based on their antimicrobial activity and minimum inhibitory concentration (MIC) against foodborne pathogens. EOs of thyme and cinnamon presented the largest antibacterial activity against foodborne pathogens. Combinations of selected EOs displayed a synergic effect against foodborne pathogens and also an important decrease in their individual MIC. Thyme EO presented the lowest individual MIC, but its utilization in combination decreased the MIC of the other EOs. Utilization of cinnamon EO also improved the reduction of the individual MICs of the EOs of cumin and parsley. Our results suggest the potential use of EO mixtures to control foodborne pathogens in meat products. Although the individual MIC values of selected EOs decreased, the sensory impact on meat products needs to be assessed.
A New Cytotoxic Stigmasterone from Agathis Macrophylla
Authors: Li Ya , Wang Tong-Tong , Gao Kun
Published: March 2019

A new stigmasterone 7α,15α-dihydroxystigmast-4-en-3-one (1), along with fifteen known compounds was isolated from the EtOAc and n-BuOH fractions of the EtOH extract of Agathis macrophylla. The structure of these compounds 1-16 were established mainly by spectroscopic analysis and by comparison of the spectroscopic data with those reported for structurally related compounds. The isolated compounds 1-8 were screened for cytotoxicity in A549 tumor cell line using RSB assay. Compounds 1 and 2 displayed moderate cytotoxicity against A549 tumor cell line with IC50 value of 36.5 and 16.0 μmol/L, respectively.
Antioxidant Flavonoids from Asteriscus Maritimus
Authors: Daroui-Mokaddem Habiba , Kabouche Ahmed , Boutaghane Naima , Calliste Claude-Alain , Duroux Jean-Luc , Kabouche Zahia
Published: March 2019

One new flavonol glycoside, patuletin-7- O-[6- O-caffeoyl-2- O-[(S)-3-hydroxyisobutanoyl]glucopyranoside] (astermaritimoside) (1) and four known flavonoids, patuletin-7- O-β-[-6- O-[( S)-3-hydroxyisobutanoyl]glucopyranoside] (2), patuletin-7- O-[6- O-caffeoylglucopyranoside] (3), patuletin-7- O-β-D-glucopyranoside (4) and quercetin-3- O-β-rutinoside (5) have been isolated from Asteriscus maritimus (L.) Less. Chemical structures were elucidated by mass spectrometric, and 1H NMR, 13C NMR, COSY, HMQC and HMBC spectroscopic techniques. The antioxidative effect was evaluated using an electronic spin resonance (ESR) method in order to visualize the inhibition of the DPPH radical. The n-butanol fraction was found to possess a remarkable antioxidant activity that was correlated with the total amount of phenolics. The isolated compounds exhibited good antioxidant activity.
Improvement of Chemical and Physical Properties and Antioxidant Evaluation of Eugenol – PEG Adduct
Authors: Zacchigna Marina , Cateni Francesca , Procida Giuseppe
Published: March 2019

Eugenol (EU) – PEG adduct was synthesized to improve the chemical and physical properties of eugenol. The phenolic group was covalently bound to the carboxyl group of PEG and the release kinetics were studied in vitro in buffer solution at pH 7.4, in simulated gastric fluid and in mouse plasma. Studies in vitro on the release of the parent drug from the prodrug in various media indicate that the adduct may be sufficiently stable to pass intact into the gastrointestinal tract and release EU into the circulation. The antioxidant activity of PEG-EU adduct was also evaluated. Scavenging activity was absent in the original PEG-EU adduct but gradually increased on the basis of drug delivery.
Composition and Variability of Leaf Oil from Monodora Crispata -13C NMR Identification of Heat-sensitive Compounds
Authors: Djié Bi Tra Marc Gabin , Yapi Acafou Thierry , Ouattara Zana Adama , Mamyrbekova-Békro Janat Akhanovna , Paoli Mathieu , Tomi Félix , Castola Vincent , Bighelli Ange
Published: March 2019

The composition of four samples of essential oil isolated from the leaves of individual Monodora crispata trees growing wild in an Ivorian forest (Adiopodoumé) were investigated by a combination of chromatographic (GC(RI)) and spectrometric (GC-MS, 13C NMR) techniques. In total, fifty-seven compounds accounting for 92.3–98.7% of the whole composition were identified. These oils were characterized by the preeminence of sesquiterpene hydrocarbons and the content of the main components varied substantially from sample to sample. Two samples were largely dominated by germacrene D (67.3% and 76.3%, respectively), a third sample was represented by germacrene D (28.3%), germacrene C (14.3%), δ-elemene (12.1%) and β-elemene (9.3%) and the fourth sample was characterized by 3-dimethylallylindole (15.1%), germacrene D (12.0%) and cyperene (7.8%). 13C NMR spectroscopy was particularly efficient for the identification of heat-sensitive compounds.
Chemical Composition of Juniperus Phoenicea and J. Drupacea Essential Oils and their Biological Effects in the Choriallantoic Membrane (CAM) Assay
Authors: Koutsaviti Aikaterini , Tzakou Olga , Galati Enza Maria , Certo Giovanna , Germanò Maria Paola
Published: March 2019

The aim of the present study was the chemical analysis of the essential oils from Juniperus phoenicea and J. drupacea female cones and evaluation of their biological effects. Fresh samples, collected in Greece, were subjected separately to hydrodistillation and the oils obtained analyzed by GC-FID and GC-MS. The oils were assessed using the CAM (chorioallantoic membrane) assay to evaluate their anti-angiogenic potential and the lack of irritant effects in topical application. GC analysis showed that mainly quantitative differences among the samples were observed: limonene was the most abundant compound in J. drupacea (27.0%) compared with J. phoenicea oil (1.6%); the content of α-pinene was high in both essential oils ( J. phoenicea 22.1%, J. drupacea 26.1%) followed by germacrene D ( J. phoenicea 7.4%, J. drupacea 7.1%, respectively). Nevertheless, qualitative differences were also detected as the diterpene 4- epi-abietal was present in a considerable amount (13.2%) in J. phoenicea essential oil, but was not detected in J. drupacea oil. In the CAM assay, only J. phoenicea essential oil evidenced a rather weak anti-angiogenic activity compared with the standard retinoic acid, but no irritant effect was observed for either essential oil suggesting their safety for topical application.
Phytoconstituents and Biological Activities of Garcinia Dulcis (Clusiaceae): A Review
Authors: Khamthong Nanthaphong , Hutadilok-Towatana Nongporn
Published: March 2019

Garcinia dulcis (Roxb.) Kurz is a tropical fruit tree native to Southeast Asia where it has a long history of use as a traditional medicine for the treatment of ailments such as lymphatitis, parotitis, struma, scurvy, cough, and sore throat. Despite its medicinal values, this plant is not well known and rarely found nowadays. Research on the phytochemical constituents and biological activities of G. dulcis have demonstrated that various parts of the plant contain an abundance of bioactive compounds mainly xanthones and flavonoids, with significant pharmacological properties such as anti-atherosclerosis, anti-bacterial, anti-cancer, anti-hypertension, and anti-malarial. In the present review, current knowledge of the phytochemistry of G. dulcis and biological activities of its active constituents based on the available literature are summarized in order to explore application potentials and prospective research works on this plant.
Sesquiterpene Quinones and Diterpenes from Smenospongia cerebriformis and Their Cytotoxic Activity
Authors: Huyen Le Thi , Hang Dan Thuy , Nhiem Nguyen Xuan , Tai Bui Huu , Anh Hoang Le Tuan , Quang Tran Hong , Yen Pham Hai , Van Minh Chau , Van Dau Nguyen , Van Kiem Phan
Published: March 2019

Using various chromatographic methods, one new sesquiterpene quinone named smenohaimien F (1) and five known, neodactyloquinone (2), dactyloquinone C (3), dactyloquinone D (4), isoamijiol (5), and amijiol (6), were isolated from the marine sponge Smenospongia cerebriformis Duchassaing & Michelotti, 1864. Their structures were elucidated by 1D-, 2D-NMR spectroscopic analysis, HR-ESI-MS, and by comparing with the NMR data reported in the literature. The cytotoxic activities of the all compounds were evaluated on five human cancer cell lines, LU-1, HL-60, SK-Mel-2, HepG-2, and MCF-7. Compound 4 was found to exhibit significant cytotoxic activities on all tested human cancer cell lines with IC50 values ranging from 0.7 to 1.6 μg/mL.
Talarofuranone, a New Talaroconvolutin Analog from the Endophytic Fungus Talaromyces purpurogenus from Pouteria campechiana Seeds
Authors: Padmathilake K.G.E. , Bandara H.M.S.K.H. , Qader M. Mallique , Kumar N. Savitri , Jayasinghe Lalith , Masubuti Hironori , Fujimoto Yoshinori
Published: March 2019

An endophytic fungus Talaromyces purpurogenus was isolated from the seeds of the popular edible fruit Pouteria campechiana. The fungus was fermented in potato dextrose agar and the fungal media were extracted with EtOAc. Chromatographic separation of the EtOAc extracts over silica gel, Sephadex LH-20 and preparative thin layer chromatography furnished a furanone analogue of talaroconvolutin A, named talarofuranone (1), along with talaroconvolutin A (2), 4-hydroxyacetophenone, tyrosol and ergosterol. The structure of 1 was determined by comparing the NMR data with that of 2 and by HRFABMS.
Effects of Intestinal Microecology on Metabolism and Pharmacokinetics of Oral Wogonoside and Baicalin
Authors: Xing Shihua , Wang Mengyue , Peng Ying , Li Xiaobo
Published: March 2019

Baicalin and wogonoside are two of the most abundant flavonoid glycosides in the root of Scutellaria baicalensis Georgi, which is a widely used peroral herbal medicine with anticancer, antiviral, antibacterial and anti-inflammatory properties. In the present study, the effects of intestinal microecology on the metabolism and pharmacokinetics of orally administered baicalin and wogonoside were investigated by UPLC-QTOF/MS measurement of the difference in metabolites between normal and antibiotic-pretreated rats. In the antibiotic-pretreated rats, the plasma concentration-time profile and pharmacokinetic parameters of the two flavonoid glycosides and their relevant aglycone forms were significantly changed compared with those in normal rats. Further, hydrolysis and glucuronidated metabolites were not detected in the cecum contents and urine samples from antibiotic-pretreated rats. These results suggested that intestinal microbiota may play a key role in the pharmacokinetics and metabolism of peroral baicalin and wogonoside. According to our findings, it is recommended that the root of S. baicalensis should not be co-administered with antibiotics in clinical use.
Isoflavone Composition, Total Phenolic Content and Antioxidant Capacity of Soybeans with Colored Seed Coat
Authors: Bursać Mira , Krstonošić Milica Atanacković , Miladinović Jegor , Malenčić Đorđe , Gvozdenović Ljiljana , Cvejić Jelena Hogervorst
Published: March 2019

The influence of soybean seed coat color and genotype on antioxidant capacity, phenolic content and isoflavone profile was investigated. Isoflavone content and composition of 21 seed samples - yellow, green, brown, black and rarely mentioned ocher and reddish, were determined by high-performance liquid chromatographic analysis. Antioxidant capacity and total phenolic content (TPC) were evaluated spectrophotometrically. Significant correlation between total isoflavone content and total genisteins was established in all colored groups. Total isoflavone content was in the range from 2.11 mg/g in a green wrinkled sample to 5.24 mg/g in yellow seed. It was found that black genotypes had the highest TPC and antioxidant capacity, which were significantly different ( p<0.05) from other colored soybeans. The obtained interconnections among analyzed isoflavones can be used as a model for estimation of their specific content.
The Antitumor Antibiotics Complex of Aureolic Acids from the Marine Sediment-associated Strain of Streptomyces sp. KMM 9048
Authors: Kalinovskaya Nataliya I. , Romanenko Lyudmila A. , Kalinovsky Anatoly I. , Ermakova Svetlana P. , Dmitrenok Pavel S. , Afiyatullov Shamil Sh.
Published: March 2019

A new antibiotic complex of six aureolic acids was isolated from the marine sediment-associated strain Streptomyces sp. KMM 9048. Four of the compounds (3–6) were found to be similar but not identical to the known chromomycins A2, A3, demethyl chromomycin A3 and A4. The two remaining compounds, A2–1 (1) and A3–1 (2), were established as novel chromomycin analogs, which did not contain sugar B. Spectroscopic methods including 1D and 2D NMR, and HRMS and MS/MS were applied for structure elucidation. Compounds 1-5 showed strong antimicrobial activity against Gram-positive indicatory bacteria Enterococcus faecium, Staphylococcus aureus, S. epidermidis, and Bacillus subtilis. Antitumor assay indicated that all tested compounds, in different manners, inhibited colony formation of RPMI-7951 and SK-Mel-28 cancer cells. This is the first study reporting the inhibitory effects of chromomycin analogs 1–5 on the colony formation of the investigated cancer cell lines. Compound 3, in a concentration of 5 nM, inhibited colony formation of RPMI-7951 and SK-Mel-28 cells by 82 % and 72 %, respectively. Our finding indicated that, of the compounds tested, 3 and 4 are promising anticancer and antimicrobial agents.
Chemical Composition and Bactericidal Activity of the Essential Oils of Four Species of Annonaceae Growing in Brazilian Amazon
Authors: Alcântara Joelma Moreira , de Lucena Juliana Mesquita V. M. , Facanali Roselaine , Marques Marcia Ortiz M. , da Paz Lima Maria
Published: March 2019

A study was conducted to determine the chemical composition and the antibacterial activity of essential oils from Bocageopsis multiflora (Mart.) R.E. Fr., Ephedranthus amazonicus R.E. Fr., Guatteria blepharophylla Mart. and Xylopia aromatica (Lam.) Mart. The essential oils were obtained from the leaves by hydrodistillation and analyzed by GC-FID and GC-MS. The chromatograms showed the predominance of sesquiterpenoids. Spathulenol was the major constituent of oils of B. multiflora (20.3%), X. aromatica (21.5%) and E. amazonicus (16.9%); followed by caryophyllene oxide of G. blepharophylla (55.7%). Other constituents with significant percentages were the sesquiterpenes β-bisabolene (11.9%) in the samples oil of B. multiflora, humulene epoxide II (16.3%) of E. amazonicus, the monoterpenes trans-pinocarveol (10.2%) and dihydrocarveol (11.6%) of X. aromatica. The essential oils of X. aromatica and G. blepharophylla showed strong activity against Gram-positive bacteria Streptococcus sanguinis by microdilution method. The antimicrobial activity against Staphylococcus aureus also was detected by G. blepharophylla essential oil.
2α-Acetoxy-15-acetylartemisiifolin, a new Anti-trypanosomal Sesquiterpene Lactone from Mikania guaco
Authors: Hussein Ahmed A. , Romero Luz , López-Pérez Jose Luis , Gupta Mahabir P.
Published: March 2019

Mikania guaco Bonpl. methanol extract showed an interesting activity against Trypanosoma cruzi with an IC50 of 4 μg/mL. Bioassay-guided fractionation of the methanol extract resulted in the isolation of a new sesquiterpene lactone, 2α-acetoxy, 15-acetylartemisiifolin (1), which was shown to be active (IC50 = 25 μM) against the amastigote form of T. cruzi,. The chemical structure of 1 was elucidated using 2-D NMR techniques and mass spectrometry.
Profiling of Phenolic Natural Products in the Seagrass Zostera noltei by UPLC-MS
Authors: Manck Lauren , Quintana Ester , Suárez Rocío , Brun Fernando G. , Hernández Ignacio , Ortega María J. , Zubía Eva
Published: March 2019

Seagrasses are marine plants that play important ecological functions in coastal ecosystems. The species Zostera noltei is widely distributed along the European coasts thriving in a variety of environmental conditions. In this study, the phenolic natural products of Z. noltei have been analyzed quantitatively by using UPLC-MS. Plants from the Natural Park of the Bay of Cadiz (Spain) were shown to contain rosmarinic acid (1) and the flavonoids apigenin-7- O-glucoside (2), luteolin-7-sulfate (7), apigenin-7-sulfate (8), diosmetin-7-sulfate (9), and acacetin-7-sulfate (10). The analysis by UPLC-MS of extracts allowed the quantification of all the compounds and evidenced the intraspecific variations in the profile of natural products among plants collected at different dates and locations within the Bay. The flavonoids 2, and 7-10 were present in all the analyzed samples with a total flavonoid content in the range 12.8–72.3 mg/g dry wt, while rosmarinic acid (1) was only present in some samples, reaching up to 19.6 mg/g dry wt. A distinctive feature of plants from the Bay of Cadiz is the common presence of apigenin-7-sulfate (8) as major flavonoid, differing from plants from other regions whose major flavonoid is diosmetin-7-sulfate (9).
Cannabidiolic Acid-Mediated Interference with AP-1 Transcriptional Activity in MDA-MB-231 Breast Cancer Cells
Authors: Suzuki Masayo , Takeda Shuso , Okazaki Hiroyuki , Watanabe Kazuhito , Takiguchi Masufumi , Aramaki Hironori
Published: March 2019

We reported that cannabidiolic acid (CBDA), a non-psychotropic constituent of fiber-type cannabis plants, down-regulates the mRNA expression of cyclooxygenase-2 (COX-2) in highly aggressive MDA-MB-231 human breast cancer cells. However, the molecular mechanism(s) underlying the CBDA suppression of COX-2 have not yet been elucidated in detail. In MDA-MB-231 cells, COX-2 expression is known to be tightly regulated by the transcriptional activity of activator protein-1 (AP-1), which is composed of a heterodimer of c-Fos and c-Jun. AP-1-mediated transcriptional activity was inhibited by CBDA in a dose-dependent manner. The expression of c-fos was maintained at markedly lower levels (0.035) than basal c-jun expression levels (1.0), implicating c-fos as a limiting factor in the regulation of COX-2. Analyses indicated that CBDA abrogated the expression of c-fos mRNA without affecting c-jun. Collectively, these results suggest that CBDA abolishes the expression of COX-2 by interfering with AP-1 activity in MDA-MB-231 cells.
Exploiting Substrate Diversity of NRPS Led to the Generation of New Sansanmycin Analogs
Authors: Wang Shan-Shan , Zhang Ning-Ning , He Ning , Guo Wen-Qiang , Lei Xuan , Cai Qiang , Hong Bin , Xie Yun-Ying
Published: March 2019

Further exploration of substrate diversity of the sansanmycin biosynthetic pathway using available halogen- and methyl-phenylalanines led to the generation of diverse sansanmycin derivatives, either at the single C- or N-terminus alone or at both C- and N-termini. The structures of all of these derivatives were determined by MS/MS spectra, and amongst them, the structures of [2-Cl-Phe]-sansanmycin H (1) and [2-Cl-Phe]-sansanmycin A (2) were further identified by NMR. Both the C-terminal derivative 1 and the N-terminal derivative 2 were assayed for their antibacterial activities, and compound 1 exhibited moderate activity against P. aeruginosa and ΔtolC mutant E. coli.
γ-Butyrolactones from Aspergillus Species: Structures, Biosynthesis, and Biological Activities
Authors: Ibrahim Sabrin R. M. , Mohamed Gamal A. , Khedr Amgad I.M.
Published: March 2019

Recently, numerous metabolites possessing uncommon structures and potent bioactivity have been isolated from strains of fungi collected from diverse environments. The genus Aspergillus is known as a rich source of γ-butyrolactones. These are a group of fungal secondary metabolites, consisting of a five-membered lactone bearing two aromatic rings, which shows a great variety of biological activities. This review summarizes the research on the biosynthesis, source, and biological activities of the naturally occurring γ-butyrolactones that have been isolated from Aspergillus species published over the last decades. More than 75 compounds are described and 65 references are cited.
Modeling of the Behavior of Natural Polysaccharides Hydrogels for Bio-pharma Applications
Authors: Caccavo Diego , Cascone Sara , Lamberti Gaetano , Dalmoro Annalisa , Barba Anna Angela
Published: March 2019

Hydrogels, even if not exclusively obtained from natural sources, are widely used for pharmaceuticals and for biomedical applications. The reasons for their uses are their biocompatibility and the possibility to obtain systems and devices with different properties, due to variable characteristics of the materials. In order to effectively design and produce these systems and devices, two main ways are available: i) trial-and-error process, at least guided by experience, during which the composition of the system and the production steps are changed in order to get the desired behavior; ii) production process guided by the a-priori simulation of the systems’ behavior, thanks to proper tuned mathematical models of the reality. Of course the second approach, when applicable, allows tremendous savings in term of human and instrumental resources.

In this mini-review, several modeling approaches useful to describe the behavior of natural polysaccharide-based hydrogels in bio-pharma applications are reported. In particular, reported case histories are: i) the size calculation of micro-particles obtained by ultrasound assisted atomization; ii) the release kinetics from core-shell micro-particles, iii) the solidification behavior of blends of synthetic and natural polymers for gel paving of blood vessels, iv) the drug release from hydrogel-based tablets. This material can be seen as a guide toward the use of mathematical modeling in bio-pharma applications.
Cucurbitane-Type Triterpenoids from Momordica charantia
Authors: Chen Chiy-Rong , Liao Yun-Wen , Kuo Yueh-Hsiung , Hsu Jue-Liang , Chang Chi-I
Published: March 2019

Two new cucurbitane-type triterpenoids, 7β,23( S)-dimethoxycucurbita-5,24-dien-3β-ol (1) and 3 β-hydroxycucurbita-6,23( E),25-trien-5 β,19-olide (2), and two known cucurbitane-type triterpenoids, 7 β,25-dimethoxycucurbita-5,23( E)-dien-3 β-ol (3) and karavilagenin D (4), were isolated from the fruit pulp of Momordica charantia. Their structures were established by means of 1D and 2D NMR spectra (1H, 13C, COSY, HMQC, HMBC, and NOESY) as well as EI-MS data.
New Steroidal Glycoside and Flavonoid Constituents from Ophiopogon japonicus
Authors: Chung Nguyen Dinh , Thao Nguyen Phuong , Tuan Ha Manh , Van Thanh Nguyen , Dang Nguyen Hai , Huong Nguyen Thi Mai , Dat Nguyen Tien
Published: March 2019

Chromatographic separations of a methanolic extract of Ophiopogon japonicus tubers resulted in the isolation of a new steroidal glycoside, (25 R)-ruscogenin 1- O-(4- O-sulfo)-β-D-fucopyranoside (1), a new C-methylflavonol, 3,4′-dimethoxy-3′,5,5′,7-tetrahydroxy-8-methylflavone (2), and a known flavonol, 3,4′-dimethoxy-3′,5,5′,7-tetrahydroxyflavone (3). The C-methylflavonol was reported for the first time from the genus Ophiopogon. Compound 1 showed moderate cytotoxicity against SK-Mel-2 and KB cells with IC50 values of 24.3 and 28.8 μM, respectively. Compound 2 was active on SK-Mel-2 cells (IC50 20.3 μM).
Moracin VN, A New Tyrosinase and Xanthine Oxidase Inhibitor from the Woods of Artocarpus heterophyllus
Authors: Le Tho Huu , Nguyen Hai Xuan , Do Truong Van Nhat , Dang Phu Hoang , Nguyen Nhan Trung , Nguyen Mai Thanh Thi
Published: March 2019

Bioactivity-guided fractionation of the woods extract of Artocarpus heterophyllus collected in Vietnam revealed that a new 2-arylbenzofuran, moracin VN (1) together with two known compounds were isolated. Compound 1 possessed the inhibitory activity on tyrosinase with IC50 value of 0.82 μM, more potent than the positive control kojic acid (IC50, 44.6 μM). Compound 1 also showed moderate inhibitory activity on xanthine oxidase with IC50 value of 22.8 μM. The kinetic study of tyrosinase was performed on moracin VN (1) showed non-competitive inhibition with Ki value of 2.40 μM.
Profiling of the Bioactive Compounds in Flowers, Leaves and Roots of Vinca sardoa
Authors: Foddai Marzia , Maldini Mariateresa , Addis Roberta , Petretto Giacomo Luigi , Chessa Mario , Pintore Giorgio
Published: March 2019

Vinca sardoa (Stern) Pignatti (Apocynaceae) is largely distributed in Sardinia where it is considered a typical endemism. Since the plant is used in traditional folk medicine, the aim of the present work was to identify and quantify the polyphenolic metabolites, due to the well-known importance of polyphenolic compounds, as well as to evaluate antioxidant activity in different parts of the plant. The compounds were identified and determined in the methanol extracts of leaves, flowers, and roots by developing different LC-MS/MS methods. The obtained data show that leaves possess the highest amount of polyphenols, in particular quinic acid (3401 mg/100 g), chlorogenic acid (1082 mg/100 g), caffeoylquinic acid isomer 1 (190 mg/100 g), and robinin (633 mg/100 g). Likewise, antioxidant tests showed that leaves possess the main radical scavenging activities in both ABTS (49.19 ± 3.41 μg/mL, 30.88 ± 3.04 μg/mL at time zero and after 50 min, respectively) and DPPH assays (223.97 ± 30.81 μg/mL, 109.52 ± 12.89 μg/mL at time zero and after 30 min, respectively). Taking into account that leaves differed most from flowers and roots in the content of caffeoylquinic acid and chlorogenic acid, of which antioxidant properties are widely recognized, it is reasonable to assume that these two compounds are involved in the differences described. The relationship between the high polyphenolic content and interesting antioxidant activities, justifies its use in ethnobotany and may be suggest a use of this specie, after removal of the alkaloid fraction, in the pharmaceutical, phytotherapy, and cosmetic industries.
Development of an Analysis Method for 4-Deoxy-l-erythro-5-hexoseulose Uronic Acid by LC/ESI/MS with Selected Ion Monitoring
Authors: Shibata Toshiyuki , Fujii Reona , Miyake Hideo , Tanaka Reiji , Mori Tetsushi , Takahashi Mami , Takagi Toshiyuki , Yoshikawa Hiroyuki , Kuroda Kouichi , Ueda Mitsuyoshi
Published: March 2019

This study describes a simple and rapid analytical quantitative method for measuring 4-deoxy-L-erythro-5-hexoseulose uronic acid (DEH) using liquid chromatography-electrospray ionization-mass spectrometry (LC/ESI/MS). For a chromatographic condition, Shodex IC NI-424 column (4.6 mm i.d. x 100 mm, 5 μm) for anion analysis and an isocratic elution of 40 mM ammonium formate buffer including 0.1% formic acid (pH 3.75) at a flow rate of 0.5 mL/min was used. The column temperature was set to 40°C. In the analysis of DEH produced by exo-type alginate lyase (AlyFRB) from Falsirhodobacter sp. alg1, a peak was detected with a retention time of 3.207 min. The prepared calibration curves for DEH analysis using the selected ion monitoring (SIM) mode of a mass spectrometer revealed a good linear relationship (correlation factor: 0.9998) within the test range (0.1–100 μg/mL). The limits of detection (S/N = 3) and quantification (S/N = 10) for DEH in SIM analysis were 0.008 and 0.027 μg/mL, respectively. Using the developed condition of LC/ESI/MS analysis, separation and detection of alginate unsaturated oligosaccharides were also tested. In an analysis time of about 13 min, this method was able to separate and detect an alginate unsaturated disaccharide, a trisaccharide, and a tetrasaccaride produced by poly(β-D-mannuronate) lyase, respectively. The analysis method established in this study will contribute to the quantitative and qualitative analysis of DEH, and the activity measurement of exo-type alginate lyase.
Diversity in the Syntheses of Muscone, Muscopyridine and Civetone
Authors: Hagiwara Hisahiro
Published: March 2019

Syntheses of muscone, muscopyridine and civetone since 1997 have been reviewed.
Two Isospongian Diterpenes from the Sponge Luffariella sp
Authors: Faricha Ana , Ahmadi Peni , de Voogd Nicole J. , Tanaka Junichi
Published: March 2019

Two isospongian diterpenes 3 and 4 in addition to known metabolites, cacofurans A (1) and B (2), were isolated from a specimen of the sponge Luffariella sp. The structures of 3 and 4 were elucidated by analyzing spectral data and chemical conversions. Although compound 3 has been reported as a synthetic entity, it was found in nature for the first time. Compound 3 showed moderate cytotoxicity.
Structural Reassignment of Koetjapic Acid following X-ray Crystallography and NMR Spectroscopy
Authors: Abubakar Saifullah , Murugaiyah Vikneswaran , Teh Chin-Hoe , Chan Kit-Lam
Published: March 2019

The crystal structure and absolute configuration of koetjapic acid were unambiguously reassigned by X-ray crystallography with strong support from NMR spectroscopic data. The acid contained 9 quaternary carbon atoms existing as an orthorhombic crystal with a space group of P21 21 21 and unit cell parameters of a = 7.6641(2), b = 14.6844(4) and c = 23.9316(6). Ring A adopted a chair conformation, ring B has an envelope conformation, whilst ring C assumed a half-chair and D displayed a chair conformation. The absolute configurations at C1 ( R), C5 ( R), C7 ( S), C10 ( S), C13 ( R), C14 ( R), C17 ( S) and C18 ( S) were assigned for the first time. The X-ray crystal of koetjapic acid was therefore reassigned as 3,4-seco-olean-4(23),12-diene-3,30-dioic acid. A plausible biogenetic synthetic pathway for compound 1 is also proposed.
Metabolomic Profiling, Antioxidant and Anti-inflammatory Activities of Hypericum Species Growing in South Korea
Authors: Yuk Heung Joo , Oh Kyeong Yeol , Kim Doo-Young , Song Hyuk-Hwan , Kim Jun Young , Oh Sei-Ryang , Ryu Hyung Won
Published: March 2019

Although Hypericum species are best known as plants that produce hypericin and are used in folk medicine, their other chemical constituents are poorly understood. Polyphenolic secondary metabolites from whole plants of representative Korean Hypericum species ( H. laxum Koidz., H. erectum Thunb., and H. ascyron L.) were analyzed using a ultra performance liquid chromatography-quadrupole time-of-flight/mass spectrometry (UPLC-Q-TOF/MS)-based approach combined with unsupervised principal component analysis (PCA) multivariate analysis. On the loading scatter plot, significant changes in metabolites were found between species, and three flavonol glycosides (8: quercetin-3- O-galactoside, 12: kaempferol-3- O-glucoside, and 13: quercetin-3- O-rhamnoside) were evaluated as key markers among 17 isolated metabolites. The extracts of H. laxum Koidz. exhibited significant quenching effects on DPPH and ABTS radicals, with IC50 values of 10–20 μg/mL, and were slightly higher in total phenol (TP) and total flavonoid (TF) contents than other species. Additionally, anti-inflammatory activity was observed by reduced nitric oxide (NO) and interleukin-6 (IL-6) production from lipopolysaccharide (LPS)-stimulated macrophages (RAW 264.7 cells). This is the first study to report the presence of bioactive metabolites and their correlating biological activities in H. laxum Koidz.
Chemical Composition of Umbilicaria crustulosa and U. cylindrica
Authors: Zlatanović Ivana , Zrnzević Ivana , Jovanović Olga , Stojanović Igor , Petrović Goran , Stojanović Gordana
Published: March 2019

The chemical composition of ether, ethyl acetate and dichloromethane extracts of Umbilicaria crustulosa and U. cylindrica were determined for the first time by HPLC-UV, GC-FID and GC-MS. The HPLC-UV analysis was revealed the presence of methyl orsellinate, lecanoric acid, crustinic acid, gyrophoric acid and atranorin in U. crustulosa extracts while in U. cylindrica extracts were detected following compounds: salazinic acid, norstictic acid, atraric acid, gyrophoric acid and atranorin. GC-FID and GC-MS analysis were enabled the identification of orsellinic acid (40.4%) and orcinol (48.1%) as main components of U. crustulosa extracts and atraric acid (8.5%) and orcinol (10.3%) in U. cylindrica extracts.
Croatian Micromeria fruticulosa – Essential Oil Composition and Antiphytoviral Activity
Authors: Ruščić Mirko , Vuko Elma , Bezić Nada , Kremerb Dario , Dunkić Valerija
Published: March 2019

The essential oil of Micromeria fruticulosa (Lamiaceae) growing wild in Croatia was obtained by hydrodistillation and analyzed by GC and GC/MS. Sixty-four compounds, representing 90.1% of the oil, were identified. The major components were oxygenated monoterpenes and sesquiterpenes with pinocarvone (17.6%), borneol (11.2%), α-bisabolol (10.5%), caryophyllene oxide (4.6%) and linalool (4.5%) as the most abundant. The essential oil showed antiviral activity against CMVsat infection.
Germacranolides from Enhydra fluctuans with TRAIL-resistance Abrogating Activity
Authors: Ahmed Firoj , Karmakar Utpal K. , Arai Midori A. , Ishikawa Naoki , Sadhu Samir K. , Ishibashi Masami
Published: March 2019

TRAIL selectively kills cancer cells without harming most normal cells. However, TRAIL resistance is a major problem for its therapeutic use. Developing a strategy to overcome resistance is crucial for the successful use of TRAIL as an antitumor agent. In our screening program of natural products that can abrogate TRAIL resistance, four germacranolides (1–4) were isolated from the aerial parts of Enhydra fluctuans. All compounds exhibited potent TRAIL-resistance overcoming activity against TRAIL-resistant human gastric adenocarcinoma (AGS) cells.
Sesqui- and Diterpenoids from Tahitian and Japanese Liverworts Jungermannia species
Authors: Nagashima Fumihiro , Asakawa Yoshinori
Published: March 2019

A new cembrane diterpenoid was isolated from the Tahitian liverwort Jungermannia species, together with several known sesquiterpenoids, and labdane and verticillane diterpenoids. Two new labdane diterpenoids, and known labdane and clerodane diterpenoids were isolated from the Japanese Jungermannia infusca collected in the three different locations. Their structures were determined by use of NMR techniques.
Saponins from Solanum torvum and S. macaonense with Their Cytotoxic and Anti-allergic Effects
Authors: Lee Chia-Lin , Yang Juan-Cheng , Peng Chieh-Yu , Wu Yang-Chang
Published: March 2019

Spirostanol saponins, 1–6 and 18–19 (normal-type F ring), isolated from Solanum torvum and S. macaonense showed anti-metastatic and anti-inflammatory effects, especially 2 and 18 could be chosen as the promising candidates against inflammation-associated tumors.
Chlokamycin, a New Chloride from the Marine-derived Streptomyces sp. MA2-12
Authors: Fukuda Takashi , Takahashi Misaki , Kasai Hiroaki , Nagai Kenichiro , Tomoda Hiroshi
Published: March 2019

A new chlorinated metabolite designated chlokamycin (1), was isolated along with ikarugamycin (2) from the culture broth of the marine-derived Streptomyces sp. MA2–12. The structure of 1 was elucidated based on spectroscopic analyses (1D and 2D NMR data and ROESY correlations). Chlokamycin moderately inhibited the growth of Jurkat cells and HCT116 cells with IC50 values of 24.7 and 33.5 μM, respectively.
Isomeric Polycyclic Polyprenylated Acylphloroglucinols from the Bark of Mesua ferrea (Clusiaceae)
Authors: Rasol Nurulfazlina Edayah , Naz Humera , Awang Khalijah , Ridhwan Mohamad Jemain Mohamad , Choy Yap Ken , Ismail Nor Hadiani
Published: March 2019

Five new isomeric polycyclic polyprenylated acylphloroglucinols (PPAPs) named mesuaferroic acid A, B, C, E and F (1–5) were isolated from ethyl acetate extract of Mesua ferrea L. (Clusiaceae). The isomeric compounds were obtained after extensive chromatographic procedures mainly using preparative HPLC. Structures were established after detailed spectroscopic analysis mostly by 2D NMR techniques. Compounds 4 and 5 exhibited good α-glucosidase inhibitory activity with IC50 values of 0.43 and 0.60 mM, respectively, comparing to the positive control, 1-deoxynojirimycin (IC50 0.63 mM).