bluuebunny/crossref_metadata_2025 huggingface dataset:
Zuccagnia punctata: A Review of its Traditional Uses, Phytochemistry, Pharmacology and Toxicology
Authors: Isla María Inés , Moreno María Alejandra , Nuño Gabriela , Rodriguez Fabiola , Carabajal Antonella , Alberto María Rosa , Zampini Iris Catiana
Published: March 2019

Zuccagnia punctata Cav. (Fabaceae, Caesalpiniaceae) is a plant with a long history of use in Argentine traditional medicines; it belongs to a monotypic genus, and is an endemic species of Argentina. This review provides a comprehensive overview of the traditional uses, phytochemistry, pharmacological activity and toxicology of Z. punctata. A wide range of traditional uses are cited in the literature such as antibacterial, antifungal, anti-inflammatory, and antitumor, among others. Pharmacological studies to date have demonstrated significant activities that support the traditional uses of this plant. No human clinical trials had been completed up to the time of this review and no toxic effect had been detected in animals. Compounds from different chemical groups have been isolated such as phenolic compounds and essential oils. Plant extracts and phytochemicals isolated exhibit a broad range of activities, anti-inflammatory, antibacterial, antifungal, antigenotoxic, antioxidant, antiulcer, and nematicidal. The main bioactive phytochemicals in the aerial parts (leaf, stem and flower) were identified as 2′, 4′-dihydroxy-3′-methoxychalcone and 2′, 4′-dihydroxychalcone and were proposed as chemical markers. Consequently, standardized dry extracts of aerial parts of Z. puntacta could be used in herbal medicinal products. Also, they could be included in phytotherapeutic preparations such as capsules, creams, and gels, and for microencapsulation.
Characterization of 12-Oxophytodienoic Acid Reductases from Rose-scented Geranium (Pelargonium graveolens)
Authors: Iijima Miu , Kenmoku Hiromichi , Takahashi Hironobu , Lee Jung-Bum , Toyota Masao , Asakawa Yoshinori , Kurosaki Fumiya , Taura Futoshi
Published: March 2019

Pelargonium graveolens L'Hér, also referred to as rose geranium, is a popular herbal plant with typical rosy fragrance largely based on the blend of monoterpenoid constituents. Among them, citronellol, which is biosynthesized from geraniol via double bond reduction, is the most abundant scent compound. In this study, three 12-oxophytodienoic acid reductases (PgOPR1–3) have been cloned from P. graveolens, as possible candidates for the double-bond reductase involved in citronellol biosynthesis. The bacterially expressed recombinant PgOPRs did not reduce geraniol to citronellol, but stereoselectively converted citral into ( S)-citronellal in the presence of NADPH. Thus, the α,β-unsaturated carbonyl moiety in the substrate is essential for the catalytic activity of PgOPRs, as reported for OPRs from other plants and structurally related yeast old yellow enzymes. PgOPRs promiscuously accepted linear and cyclic α,β-unsaturated carbonyl substrates, including methacrolein, a typical reactive carbonyl compound. The possible biotechnological applications for PgOPRs in plant metabolic engineering, based on their catalytic properties, are discussed herein.
Oxytoxin-2, An Algal-Derived Molecule from a Cultured Mollusc Volvatella vigourouxi
Authors: Chen Wu-Fu , Chang Yu-Chia , Chiu Yuh-Wen , Fang Lee-Shing , Chen Yu-Hsin , Su Yin-Di , Peng Bo-Rong , Lu Mei-Chin , Chen Jih-Jung , Wen Zhi-Hong , Wu Yang-Chang , Sung Ping-Jyun
Published: March 2019

A natural caulerpenyne-derived sesquiterpene, oxytoxin-2 (1), was isolated from a cultured mollusc Volvatella vigourouxi. The structure of 1 was elucidated on the basis of spectroscopic analysis and this compound was suggested to be a diet-derived metabolite from the green alga Caulerpa sertularioides. This is the first study on the chemical constituents of V. vigourouxi. Oxytoxin-2 (1) was found to inhibit significantly the expression of the pro-inflammatory inducible nitric oxide synthase (iNOS) protein of lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells.
Inhibitory Activities of Essential Oil Obtained from Turmeric and Its Constituents against β-Secretase
Authors: Matsumura Shinichi , Murata Kazuya , Zaima Nobuhiro , Yoshioka Yuri , Morimoto Masanori , Kugo Hirona , Yamamoto Ayami , Moriyama Tatsuya , Matsuda Hideaki
Published: March 2019

The need for a preventive agent against dementia led us to screen natural plant resources. Among the herbs and spices tested, turmeric, from rhizomes of Curcuma longa, showed high potency against β-secretase. The active principles were determined as α-turmerone, β-turmerone and ar-turmerone, with IC50 values of 39, 62 and 92 μM respectively. In this study, the efficiency of collecting the essential oil using steam distillation of the volatile substance was disclosed. The active principles were explored, and four sesquiterpenoids and five monoterpenoids were revealed as active principles against β-secretase. On the other hand, α-turmerone, β-turmerone and ar-turmerone were also investigated in a pharmacokinetic absorption experiment. After oral administration, these compounds were detected in an intact form in the brain and serum. These results suggest that consumption of turmeric constituents may prevent dementia.
The Isolation of Lutein and Lutein 3′-methyl ether from Peristrophe lanceolaria
Authors: Prapalert Wasana , Santiarworn Dammrong , Liawruangrath Saisunee , Liawruangrath Boonsom , Pyne Stephen G.
Published: March 2019

Two carotenoids, lutein (1) and lutein 3′-methyl ether (2), have been isolated from the EtOAc fraction of the MeOH extract of Peristrophe lanceolaria, growing in Thailand. The structures of these compounds were elucidated from their 1D and 2D NMR spectroscopic data and from comparisons made with the literature data. This is the first report of the isolation of lutein-3′-methyl ether as a natural product.
Anti-inflammatory, Anti-bacterial and Anti-acetylcholinesterase Activities of two Isoquinoline Alkaloids–Scoulerine and Cheilanthifoline
Authors: Wangchuk Phurpa , Sastraruji Thanapat , Taweechotipatr Malai , Keller Paul A , Pyne Stephen G
Published: March 2019

Corydalis plants containing isoquinoline alkaloids are reported to possess promising pharmacological properties for the treatment of important diseases including cancer, inflammation, Alzheimer's disease and microbial infections. As part of a wider program investigating Bhutanese medicinal plants, we have previously identified eight isoquinoline alkaloids from C. dubia. Out of these, we report here on two of the major alkaloids, scoulerine (1) and cheilanthifoline (2) and their inhibitory activities against acetylcholinesterase (anti-AChE), tumor necrosis factor alpha (anti TNF-α) and a bacterial strain, Helicobacter pylori. Both alkaloids showed weak anti TNF-α and antibacterial activities. However, the anti-AChE activity of scoulerine (1) was promising as it significantly inhibited AChE with a minimum inhibitory requirement (MIR) value of 0.0015 nmol, which was two-fold better than the reference drug, galanthamine (MIR value of 0.003 nmol). As there are limited anti-Alzheimer's chemotherapeutics, scoulerine (1) is worthy of further exploration, including lead optimization, structure-activity-relationship studies, analog development, pharmacodynamics and in vivo animal studies
Chemical Differentiation of Pseudostellariae Radix from Different Cultivated Fields and Germplasms by UPLC-Triple TOF-MS/MS Coupled with Multivariate Statistical Analysis
Authors: Hua Yu-Jiao , Hou Ya , Wang Sheng-Nan , Ma Yang , Zou Li-Si , Liu Xun-Hong , Luo Yi-Yuan , Liu Juan-Xiu
Published: March 2019

To explore rapidly the potential chemical markers for differentiating Pseudostellariae Radix from different cultivated fields and germplasms, a method is proposed based on ultra-performance liquid chromatography-triple time-of-flight mass/mass spectrometry (UPLC-Triple TOF-MS/MS) coupled with multivariate statistical analysis. Peak matching, peak alignment, and noise filtering were used in analyzing mass spectrometric data. Accurate m/z value analysis of MS data based on software of database search and MS/MS fragment analysis were applied to identify constituents. The obtained data were statistically analyzed with hierarchical cluster analysis (HCA), principal component analysis (PCA), and partial least squared-discriminant analysis (PLS-DA) to compare the differences among these samples. The PLS-DA loading plot obtained from all mass data showed that 21 compounds were identified as the potential chemical markers to characterize the samples. The results provide experimental data to reveal the influence of ecological environments and germplasms on metabolite biosynthesis in Pseudostellariae Radix.
Characterization of the α-Amylase Inhibitory Activity of Oligomeric Proanthocyanidins from Acacia mearnsii Bark Extract
Authors: Matsuo Yosuke , Kusano Rie , Ogawa Sosuke , Yazaki Yoshikazu , Tanaka Takashi
Published: March 2019

Acacia mearnsii (Fabaceae) contains acacia polyphenols, which are a complex mixture of proanthocyanidins that are mainly composed of 5-deoxycatechin units. In this study, an aqueous extract of A. mearnsii bark was fractionated and the α-amylase inhibitory activity of each fraction was evaluated. The 13C NMR and MS data and the pyrolysis products obtained from the active and inactive fractions were compared. The spectroscopic results clearly indicated that fractions with strong inhibitory activity contained proanthocyanidin oligomers with catechol-type B-rings rather than pyrogallol-type B-rings. HPLC analysis of the pyrolysis products showed peaks for pyrocatechol were only observed in the mixtures obtained from the fractions with high inhibitory activities. In addition, (+)-pinitol was isolated as a major polyol of the extract at a level comparable with that of sucrose.
A New Lactone from Chaetomium globosum Strain M65 that Inhibits the Motility of Zoospores
Authors: Mondol Muhammad Abdul Mojid , Farthouse Jannatul , Islam Mohammad Tofazzal , Schüffler Anja , Laatsch Hartmut
Published: March 2019

In a search for endophytes from medicinal plants of Bangladesh, we isolated the M65 fungal strain from the fruit of Azadirachta indica. Following chemical screening, chromatographic purification of the culture extract of strain M65 led to the isolation of the previously reported lasiodiplodin (2), the known derivative 1, and the new derivative 3a, along with two further known compounds (4 and 5). The new (3 R,5 R)-5-hydroxylasiodiplodin (3a), the enantiomer of the known (3 S,5 S)-5-hydroxylasiodiplodin (3b), inhibited the motility of zoospores of a devastating late blight phytopathogen Phytophthora capsici by 100% at a concentration of 10 μg/mL. The respective activities of the other metabolites were negligible.
Cytotoxic Activity of Microalgal-derived Oxylipins against Human Cancer Cell lines and their Impact on ATP Levels
Authors: Ávila-Román Javier , Talero Elena , de los Reyes Carolina , Zubía Eva , Motilva Virginia , García-Mauriño Sofía
Published: March 2019

Oxylipins are metabolites derived from lipid peroxidation. The plant oxylipin methyl jasmonate (MJ) shows cytotoxic activity against cancer cell lines of various origins, with ATP-depletion being one of the mechanisms responsible for this effect. The cytotoxic activity of oxylipins (OXLs) isolated from the microalgae Chlamydomonas debaryana (13-HOTE) and Nannochloropsis gaditana (15-HEPE) was higher against UACC-62 (melanoma) than towards HT-29 (colon adenocarcinoma) cells. OXLs lowered the ATP levels of HT-29 and UACC-62 cells, but the effect was higher on the second cell line, which had higher basal ATP. This result proves a link between the cytotoxicity and the capability of these compounds to deplete ATP. In addition, the combination of 13-HOTE with the anticancer drug 5-fluorouracil (5-FU) induced a synergistic toxicity against HT-29 cells. These results highlight the therapeutic potential of oxylipins derived from microalgae.
Enzyme-Treated Asparagus Extract Prevents Hydrogen Peroxide-Induced Pro-Inflammatory Responses by Suppressing p65 Nuclear Translocation in Skin L929 Fibroblasts
Authors: Shirato Ken , Takanari Jun , Sakurai Takuya , Ogasawara Junetsu , Imaizumi Kazuhiko , Ohno Hideki , Kizaki Takako
Published: March 2019

We recently reported that enzyme-treated asparagus extract (ETAS) attenuates hydrogen peroxide (H2O2)-stimulated matrix metalloproteinase-9 expression in skin fibroblast L929 cells. To further elucidate the anti-aging effects of ETAS on skin, we examined whether ETAS has preventive effects on H2O2-induced pro-inflammatory responses of skin fibroblasts. H2O2 induced Ser536 phosphorylation and nuclear accumulation of nuclear factor-κB (NF-κB) p65, and increased the mRNA levels of interleukin-12α (IL-12α) and inducible nitric oxide synthase (iNOS) in L929 cells. Pretreatment of the cells with JSH-23, an inhibitor of NF-κB nuclear translocation, abolished the H2O2-induced expression of IL-12α and iNOS, indicating that the increased transcription is regulated by p65. The H2O2-stimulated nuclear accumulation of p65 and induction of IL-12α and iNOS mRNA were significantly attenuated after pretreatment with ETAS for 3 h, and these responses were completely abolished when the duration was extended to 24 h. However, ETAS did not affect the H2O2-stimulated degradation of IκBα and phosphorylation of p65. On the other hand, ETAS treatment for 24 h resulted in decreased protein levels of importin-α. These results suggest that ETAS prevents pro-inflammatory responses by suppressing the p65 nuclear translocation in skin fibroblasts induced by H2O2.
Constituents and Insecticidal Activity of Deinbollia pinnata Essential Oil
Authors: Sotubo Sunkanmi E. , Lawal Oladipupo A. , Osunsami Adesola A. , Ogunwande Isiaka A.
Published: March 2019

The volatile constituents and insecticidal activity of the essential oil obtained by hydrodistillation of pulverized air-dried leaves of Dehinbollia pinnata Schum. & Thonn (Sapindaceae) growing in Nigeria were studied. The constituents of the oil were analyzed by gas chromatography (GC) and gas chromatography coupled with mass spectrometry (GC-MS). The percentage yield of the oil was 0.04% (v/w). Fourteen compounds were characterized, representing 94.0% of the total volatile component of the oil. The major constituents of the oil were hexahydrofarnesyl acetone (37.5%), farnesyl acetone (17.2%) and geranyl acetone (14.6%). The essential oil, at a concentration of 120 mg/mL, displayed 100% mortality against Sitophilus zeamais at 72 h with a LC50 > 40.00 mg/mL air.
Chemical Composition of the Essential Oils of Some Central Asian Nepeta Species (Lamiaceae) by GLC-MS
Authors: Mamadalieva Nilufar Z. , Sharopov Farukh S. , Satyal Prabodh , Azimova Shahnoz S. , Wink Michael
Published: March 2019

The chemical composition of the essential oils obtained from aerial parts of Nepeta alatavica Lipsky, N. nuda L., and N. olgae Regel (Lamiaceae), growing wild in Central Asia (Tajikistan and Uzbekistan), were analyzed by GLC and GLC-MS. The main constituents of the essential oil from N. nuda were 1,8-cineole (24.6%), 4a-α,7-β,7a-α-nepetalactone (21.0%), germacrene D (13.5%), and β-caryophyllene (12.7%), whereas those of N. alatavica were thymol (48.5%), verbenone (7.7%), and carvacrol (7.5%). In the essential oil of N. olgae the most abundant compounds were acetylcyclohexene (31.5%), 4-tridecyne (13.2%), 2-methyl cyclopentanone (6.8%) and 1,8-cineole (6.0%). The potential antioxidant activity of these essential oils was studied by using DPPH, ABTS and FRAP assays. The essential oil of N. alatavica showed the highest in vitro free radical scavenging activity, probably due to its high thymol and carvacrol content.
Chemical Composition, Enantiomeric Distribution, and Biological Activities of Rhododendron anthopogon Leaf Essential Oil from Nepal
Authors: Dosoky Noura S. , Satyal Prabodh , Pokharel Suraj , Setzer William N.
Published: March 2019

Rhododendron anthopogon D. Don., a small compact Himalayan shrub growing in Nepal, is a known medicinal plant used to treat sore throat, colds, blood disorders, bone disease, potato allergies, and vomiting, and to relieve liver disorders, headaches and back pain. The present study investigated the chemical composition and bioactivities of the leaf essential oil from R. anthopogon from Dhankuta, Nepal. The essential oil from leaves was obtained by hydrodistillation and a detailed chemical analysis was conducted by gas chromatography – mass spectrometry (GC-MS). The enantiomeric distribution of monoterpenoid components was determined using chiral gas chromatography and represents the first chiral examination of R. anthopogon essential oil. The essential oil was screened for antimicrobial activity using the microbroth dilution test, and for cytotoxic activity against MCF-7, MDA-MB-231, and 5637 using the MTT assay. A total of 70 volatile components were identified from the essential oil. The major components were α-pinene (21.5%), δ-cadinene (13.8%), β-pinene (9.5%), limonene (5.9%), δ-amorphene (4.6%), α-muurolene (4.5%), and ( E)-caryophyllene (3.2%) with other minor constituents (< 3%). The essential oil showed marginal antibacterial and cytotoxic activities, but no antifungal effects.
Chemical Composition, Antibacterial and α-Glucosidase Inhibitory Activities of the Essential Oils of Neolitsea coccinea (Lauraceae)
Authors: Jani Nor Akmalazura , Sirat Hasnah Mohd , Ahmad Farediah , Ali Nor Azah Mohamad , Zainal Muhd Hafizi
Published: March 2019

The chemical composition, antibacterial and α-glucosidase inhibitory activities of the essential oils obtained from hydrodistillation of the fresh stem and leaf of Neolitsea coccinea B. C. Stone are reported for the first time. GC and GC-MS analysis revealed the presence of 42 volatile compounds from the stem and leaf oils, accounting for 84.9% and 90.4%, respectively of the identified components. The principle compounds in the stem oil were δ-cadinene (21.2%), 1-epi-cubenol (11.3%) and cyperotundone (10.7%), while the main compounds in the leaf oil were selin-11-en-4-α-ol (26.8%), bicyclogermacrene (12.6%), γ-eudesmol (7.1%), germacrene D (6.1%) and globulol (5.9%). The leaf oil demonstrated moderate to weak antibacterial activity towards Bacillus subtilis and Staphylococcus aureus with MIC values of 250 μg/mL and 500 μg/mL, respectively, whereas the stem oil possessed weak antibacterial activity against B. subtilis with a MIC value of 500 μg/mL. The stem and leaf oils showed significant α-glucosidase inhibitory activity with IC50 values of 32.2 ± 0.8 μg/mL and 70.9 ± 1.1 μg/mL, respectively.
Micromeria thymifolia Essential Oil Suppresses Quorum-sensing Signaling in Pseudomonas aeruginosa
Authors: Bukvički Danka , Cirić Ana , Soković Marina , Vannini Lucia , Nissen Lorenzo , Novaković Miroslav , Vujisić Ljubodrag , Asakawa Yoshinori , Marin Petar D.
Published: March 2019

The chemical composition, antimicrobial and antiquorum sensing activity of the essential oil of Micromeria thymifolia (Scop.) Fritsch were investigated. Limonene, piperitone epoxide and piperitenone epoxide were found as the main constituents using a gas chromatography-mass spectrometry technique. In vitro antimicrobial activity of the oil was tested against six bacterial and seven fungal strains and high antimicrobial potential was noticed. Minimum inhibitory concentration varied from 0.031 mg/mL to 0.5 mg/mL for bacterial and 0.062 mg/mL to 0.5 mg/mL for fungal strains. The antiquorum properties of the essential oil were evaluated on Pseudomonas aeruginosa PAO1. The oil was tested at subMIC concentrations for anti-quorum sensing activity. The analyses on quorum-sensing functions have been carried out by evaluating twitching and swarming of bacterial cultures and the total amount of pyocyanin production produced by P. aeruginosa. This study showed that M. thymifolia essential oil exhibited antiquorum sensing activity and may be used as an antipathogenic drug.
Phenylpropanoid-rich Essential Oils of Piper Species from the Amazon and their Antifungal and Anti-cholinesterase Activities
Authors: da Silva Joyce Kelly R. , Silva Nayla N. S. , Santana Jessica Fernanda S. , Andrade Eloísa Helena A. , Maia José Guilherme S. , Setzer William N.
Published: March 2019

The essential oils (EOs) from aerial parts of Piper aduncum, P. callosum and P. marginatum, collected from the Amazon region of Brazil, were analyzed by GC-MS and then evaluated for their antifungal and anticholinesterase activities. The essential oils were dominated by phenylpropanoids, such as dillapiole (73.0%) in P. aduncum, safrole (66.0%) in P. callosum and 3,4-methylenedioxypropiophenone (21.8%) in P. marginatum. The analyzed oils showed low to moderate antifungal activity, with detection limits (DL) from 10 to 100 μg against Cladosporium cladosporioides and C. sphareospermum. In the anticholinesterase (AChE) evaluation, the oils of P. callosum (DL = 0.01 ng) and P. marginatum (DL = 0.01 ng) were one hundred times more potent than the standard physostigmine (DL = 1.0 ng). Molecular docking analysis showed that phenylpropanoids docked reasonably well with acetylcholinesterase and may be responsible for the anti-AChE activities of the Piper EOs. This is the first presentation about acetylcholinesterase inhibition by methylenedioxyphenyl-propanoids.
Chemical Composition and Acaricidal Activity of Nemuaron vieillardii Essential Oil against the Cattle Tick Rhipicephalus (Boophilus) microplus
Authors: Lebouvier Nicolas , Hue Thomas , Brophy Joseph , Hnawia Edouard , Nour Mohammed
Published: March 2019

Essential oil from leaves of Nemuaron vieillardii (Baill.) Baill., a shrub used in the kanak pharmacopeia, was analyzed by gas chromatography and combined gas chromatography-mass spectrometry. The main compounds identified were safrole (49.7%), linalool (8.0%), δ-cadinene (5.1%), caryophyllene oxide (4%) and α-copaene (2.4%). This chemical composition is consistent with leaf oils of the Atherospermataceae family and demonstrates the proximity of the two genera Nemuaron and Atherosperma as regards to their essential oil compositions. The modified Larval Packet Test (LPT) was used to assess acaricidal effect of N. vieillardii essential oil on larvae of the cattle tick Rhipicephalus (Boophilus) microplus and LC50 was then calculated to 14.67%. High content of safrole in this oil which is suspected of being a human carcinogen, poses the problem of the use of this oil in a perspective of development of alternative tick control strategy and in the traditional medicinal consumption of Nemuaron vieillardii.
Quantification of Saponins in Asparagus racemosus by HPLC-Q-TOF-MS/MS
Authors: Onlom Churanya , Nuengchamnong Nitra , Phrompittayarat Watoo , Putalun Waraporn , Waranuch Neti , Ingkaninan Kornkanok
Published: March 2019

Asparagus racemosus Willd. or Shatavari (Asparagaceae family) is an important medicinal plant in Ayurvedic medicine as a rejuvenate for women. A method for quantitative analysis of saponin glycosides bioactive constituents in A. racemosus is reported. A high performance liquid chromatography quadrupole time of flight mass spectrometry (HPLC-Q-TOF-MS/MS) method was developed and validated for simultaneous determination of five saponin glycosides, asparacoside, shatavarin IX, shatavarin IV, asparanin A and shatavarin V in A. racemosus extracted with 70% MeOH. The method was validated through intra-and inter-day precision, with the relative standard deviation (RSD) less than 6%, limits of detection (LOD) and limits of quantification (LOQ) <10 and 50 ng, respectively. Overall recoveries ranged from 95% to 105%, with RSD ranging from 0.7% to 4.5%. The method was applied to saponin glycoside contents in the leaves, stems, and roots of A. racemosus sourced from different geographical locations, including four provinces in Thailand, and a sample from India. Saponin glycosides were detected predominantly in the roots, the part used in traditional medicines and these showed wide variations in saponin glycoside profiles from undetectable to 12 mg/g dry weight. The quality control of A. racemosus is crucial for reliable and predictable therapies and only methods like the one developed has the necessary flexibility, sensitivity, accuracy, and selectivity for reliable routine quality control.
New Alkaloids and Anti-inflammatory Constituents from the Leaves of Antidesma ghaesembilla
Authors: Van Kiem Phan , Cuong Le Canh Viet , Trang Do Thi , Nhiem Nguyen Xuan , Anh Hoang Le Tuan , Tai Bui Huu , Huong Le Mai , Van Minh Chau , Lee Taek Hwan , Kim Sun Yeou , Kim Seung Hyun
Published: March 2019

Using various chromatographic methods, two new alkaloids, antidesoic acids A (1) and B (2) along with fourteen known compounds (3-16) were isolated from the leaves of Antidesma ghaesembilla Gaertn. Their chemical structures were elucidated by physical and chemical methods. All the isolated compounds were evaluated for their inhibitory activity on LPS-stimulated nitric oxide (NO) production in BV2 cells and RAW 264.7 macrophages. Bisflavone 8 significantly inhibited LPS-stimulated NO production in BV2 cells and RAW 264.7 macrophages with IC50 values of 5.4 and 8.0 μM, respectively. Compounds 1–3, 7, 10, 12, 14, and 16 showed moderate inhibitory activities with IC50 values ranging from 11.7 to 77.4 μM.
Chemical Characterization of Narcissus poeticus from Sirente –Velino (Apennines - Italy): Galantamine Accumulation and Distribution of Allergenic Compounds in the Flower
Authors: Ferri Donatella , Ubaldi Carla , Marcozzi Giordana , Fasciani Paolo , Bacchetta Loretta , Pace Loretta
Published: March 2019

Species of Narcissus (family Amaryllidaceae) are a potential source for large-scale extraction of alkaloids and fragrances. The bulbs typically accumulate a large number of alkaloids, including galantamine, a benzazepine alkaloid proven to be a cholinesterase inhibitor and which is used in the treatment of Alzheimer's disease. The presence of galantamine in N. poeticus L. collected in Abruzzo (Italy) was assessed and several levels of alkaloid were found in all parts of the plant (flower, stem, bulb and root) and not only in the bulb. The amount of galantamine obtained was tested by using two different extraction solvents. Extraction of N. poeticus absolute from the flowers was also performed, as this product is an important floral note in perfumery, and the distribution of allergenic compounds in the coronas and in the tepals was assessed. Moreover, the in vitro propagation of N. poeticus was tested as it may be a valuable resource from which to produce biomolecules, as an alternative to chemical synthetic processes.
A New Imidazole from the Sponge Dercitus (Halinastra) japonensis
Authors: Hirade Hiromi , Haruyama Takahiro , Kobayashi Nobuyuki , de Voogd Nicole J. , Tanaka Junichi
Published: March 2019

A new imidazole sulfate (1) and three known compounds (2-4) were isolated from the sponge Dercitus (Halinastra) japonensis. The structure of compound 1 was elucidated by spectroscopic means. Compound 2 was confirmed to show anti-HIV activity, whereas compounds 1, 3 and 4 were inactive.
Application of Mixture Analysis to Crude Materials from Natural Resources (V) [1]: Discrimination of Glycyrrhiza uralensis and G. glabra by EI mass spectrometry
Authors: Baba Masaki , Fukuda Eriko , Uesawa Yoshihiro , Kai Hisahiro , Matsuno Koji , Okada Yoshihito
Published: March 2019

The roots and stolons of some Glycyrrhiza species are used worldwide for traditional folk medicines and commercial pharmaceuticals. Phenolic constituents such as flavonoids and coumarins are medicinal and vary according to species. Therefore, species identification is important for quality analysis. In order to identify Glycyrrhiza species by chemical fingerprinting, methanol extracts of the root bark of Glycyrrhiza uralensis Fischer and G. glabra Linné were analyzed using EI-MS. Differences in kinds and quantity of components are reflected in complex EI-MS data and determining characteristic peaks for each species is straightforward. The characteristic peaks were determined statistically by volcano plot, a multivariate analysis method. EI-MS data of G. uralensis and G. glabra showed differential patterns, and the notable peaks in each pattern were identified. Peaks at m/z 153 and 221 are signature peaks of G. uralensis, and at m/z 173, 309, and 324 are those of G. glabra. In conclusion, we found species-specific patterns by EI-MS that distinguish G. uralensis and G. glabra. This method based on chemical constituent patterns can be applied to identify other Glycyrrhiza species and similar natural products.
The Influence of Extraction Parameters on Antimicrobial Activity of Propolis Extracts
Authors: Jug Mario , Karas Ognjen , Kosalec Ivan
Published: March 2019

The extraction optimization of the poplar-type propolis was performed in order to improve the isolation of flavonoids as well as the corresponding antimicrobial activity of the products obtained. The efficiency of flavonoids extraction depended upon the type of extraction media used, following the rank 80% ethanol >40 ethanol>> water, regardless of pH value. Ultrasound assisted extraction was as efficient as the maceration procedure, offering additional benefits such as short duration time and low extraction temperature. The antimicrobial efficiency of extracts prepared with 80 and 40% ethanol against the tested microbial stains was comparable, regardless of the extraction technique used, while aqueous extracts mainly showed scarce activity. Observed activity against the yeast Candida albicans strongly correlated with flavones and flavonols content in extracts prepared (r2=0.8217), while regression analysis showed that beside flavonoids, some other components which were successfully extracted from the crude propolis contributed to the observed antimicrobial efficiency against Bacillus subtilis and Staphylococcus aureus.
Phenanthrenes from Eulophia macrobulbon as Novel Phosphodiesterase-5 Inhibitors
Authors: Temkitthawon Prapapan , Changwichit Kanokwan , Khorana Nantaka , Viyoch Jarupa , Suwanborirux Khanit , Ingkaninan Kornkanok
Published: March 2019

Phosphodiesterase 5 (PDE5) inhibitors can be used for the treatment of erectile dysfunction and pulmonary hypertension. In order to search for new leads of PDE5 inhibitors, we investigated the chemical constituents of the tubers of Eulophia macrobulbon (E.C. Parish & Rchb. f) Hook. f A new phenanthrene, 9,10-dihydro-4-(4′-hydroxybenzyl)-2,5-dimethoxyphenanthrene-1,7-diol (1) and three known phenanthrenes i.e., 1-(4′-hydroxybenzyl)-4,8-dimethoxyphenanthrene-2,7-diol (2), (9,10-dihydro-2,5-dimethoxyphenanthrene-1,7-diol (3) and 1,5,7-trimethoxyphenanthrene-2,6-diol) (4) were isolated. Among these, 2 was the most potent PDE5 inhibitor (IC50 =1.67±0.54 μM) evaluated by the [3H]cGMP radioassay method, whereas 1 showed mild activity (IC50 = 62.3±3.3 μM). Their inhibitory selectivities against PDE5 over PDE6 were also studied. This study suggests phenanthrenes as a new class of PDE5 inhibitors.
Bioactive Glucitol-Core Containing Gallotannins and other Phytochemicals from Silver Maple (Acer saccharinum) Leaves
Authors: Muhsinah Abdullatif Bin , Ma Hang , DaSilva Nicholas A. , Yuan Tao , Seeram Navindra P.
Published: March 2019

In the course of our group's investigation of members of the maple ( Acer) genus, a series of glucitol-core containing gallotannins (GCGs) were isolated and identified (by NMR and HREISMS). Among higher plants, only certain maple species are known to produce GCGs, compounds with potential nutraceutical and cosmetic applications due to their reported antioxidant, antidiabetic, anti-α-glucosidase, anti-glycation, anticancer, and skin health promoting effects. Herein, we sought to investigate whether the previously un-investigated silver maple (Acer saccharinum) species was also a source of GCGs. Nine phenolic compounds, including six GCGs, were identified (by HPLC-DAD analyses using previously isolated standards) as ginnalins A-C (1-3), maplexins B, D, and F (4-6), methyl syringate (7), methyl gallate (8), and 3-methoxy-4-hydroxyphenol-1-β-D-(6-galloyl)-glucopyranoside (9). In addition, one sesquiterpenoid, namely, pubineroid A (10), was isolated and identified (by NMR).
Pterostilbene and Its Glucoside Induce Type XVII Collagen Expression
Authors: Hamada Hiroki , Shimoda Kei , Horio Yoshiyuki , Ono Tsubasa , Hosoda Ryusuke , Nakayama Noriyuki , Urano Koichi
Published: March 2019

The glycosylation of pterostilbene by cultured plant cells of Phytolacca americana gave pterostilbene 4′- O-β-D-glucoside. Both pterostilbene and its 4- O-β-D-glucoside induced type XVII collagen expression in the EpiDermFT EFT-400 human skin cell model. Pterostilbene 4′- O-β-D-glucoside strongly induced type XVII collagen expression rather than pterostilbene.
Ferulic Acid Esters of Oligo-glucose from Allium macrostemon
Authors: Usui Ayaka , Matsuo Yosuke , Tanaka Takashi , Ohshima Kazusato , Fukuda Shinji , Mine Takara , Nakayama Hideyuki , Ishimaru Kanji
Published: March 2019

Two new ferulic acid esters of oligo-glucose, 1- O- (E)-feruloyl-β-D-gentiobioside (1) and 1- O-( E)-feruloyl-{β-D-glucopyranosyl (1→6)-[β-D-glucopyranosyl (1→2)]}-β-D-glucopyranoside (allimacronoid D, 2) were isolated together with 1- O-( E)-feruloyl-β-D-glucopyranoside (3) and trans-ferulic acid (4) from the leaves of Allium macrostemon Bunge. The chemical structures were elucidated based on the analyses of the spectroscopic and chemical data.
Quantitative Analysis of Phenolic Acids and Antiplatelet Activity of Melissa officinalis Leaf Extracts
Authors: Maleš Željan , Antolić Andrea , Babić Ivana , Jurić Sandra , Bojić Mirza
Published: March 2019

The contents of total phenolic acids and rosmarinic acid were determined and the antiplatelet potential assessed of extracts of lemon balm ( Melissa officinalis L., Lamiaceae) leaf samples collected during 2014 and 2015. The quantity of total phenolic acids ranged from 4.8 to 8.5%, while the rosmarinic acid content ranged from 1.78 to 4.35%. Results of statistical analysis showed that the undiluted extracts have antiplatelet activity in the ADP test (final concentration 31.25 mg/L). While there are reports on antiplatelet activity of lemon balm essential oil, to the best of our knowledge, this is the first report on antiplatelet activity of lemon balm leaf extracts.
A Concise Synthesis of Rhodanthpyrone A and B, Natural 4-(Hydroxyphenyl)-substituted α-Pyrones
Authors: Han Young Taek
Published: March 2019

A concise synthesis of rhodanthpyrone A and B was accomplished via a Suzuki coupling reaction. To find the conditions appropriate to install hydroxyphenyl moieties to the α-pyrone skeleton, a model study was conducted using commercially available boronic acids. It was revealed that the hydroxy moiety of the phenylboronic acids should be concealed when reacted with labile 4-tosyl α-pyrone. Consequently, rhodanthpyrone A and B could be synthesized in high yields by Suzuki reaction using TIPS-protected arylboronic acids. This procedure provided a concise and versatile route for the synthesis of rhodanthpyrones and their 4-aryl substituted α-pyrone analogs.
A New Lignan from the Leaves of Zanthoxylum armatum
Authors: Bhatt Vinod , Sharma Sushila , Kumar Neeraj , Singh Bikram
Published: March 2019

A new furofuran lignan, zanthonin (1) together with 13 known compounds including seven furofuran lignans (2–8), one isobutyl amide (9), a furanocoumarin (10) and four flavonoids (11–14) have been isolated from the leaves of Zanthoxylum armatum. The chemical structures of these compounds were elucidated mainly on the basis of NMR (1D and 2D) and MS data. This is the first report on the isolation of methylxanthoxylol (4) from Z. armatum.
Production of Podophyllotoxin by Plant Tissue Cultures of Juniperus virginiana
Authors: Kašparová Marie , Martin Jan , Tůmová Lenka , Spilková Jiřina
Published: March 2019

Plant tissue cultures are a potential source of secondary metabolites. However, their production, when compared with intact plants, is usually lower. Phenylalanine, a biogenetic precursor of podophyllotoxin, was used to stimulate podophyllotoxin production in callus and suspension cultures of Juniperus virginiana L. The best phenylalanine effect on podophyllotoxin production was manifested in three-years-old callus cultures after a 21-days application of a 10 mmol/L concentration. A podophyllotoxin content of 0.15 mg/g DW was determined, which was about 400% higher in comparison with the control. The maximum content (0.48 mg/g DW) in newly derived suspension cultures (the 4th passage) was induced by 14-days application of a 1 mmol/L concentration; this was about 243% higher than the control. In one-year-old suspension cultures the highest podophyllotoxin content (0.56 mg/g DW) was recorded also after 14-days application of a 1 mmol/L concentration; this was about 211% higher than in the control cultures.
New Data on Vanillin-Based Isothiazolic Insecticide Synergists
Authors: Kletskov Alexey V. , Potkin Vladimir I. , Dikusar Evgenij A. , Zolotar Romualda M.
Published: March 2019

By alkylation of vanillin with 4,5-dichloro-3-chloromethylisothiazole the corresponding ether was synthesized. The latter was then reacted with p-toluidine to afford the corresponding azomethine. During the bioassays of synthesized isothiazolic derivatives of vanillin in mixtures with insecticides (imidacloprid and α-cypermethrin) a strong synergetic effect was observed.
OM-X®, a Fermented Vegetables Extract, Facilitates Muscle Endurance Capacity in Swimming Exercise Mice
Authors: Itoh Tomohiro , Miyake Yasuyoshi , Yamaguchi Takayuki , Tsukaguchi Shota , Mitarai Rena , Enomoto Miyuki , Ensho Seiya , Shimomiya Yoshie , Nakamura Yuki , Ando Masashi , Tsukamasa Yasuyuki , Takahata Muneaki
Published: March 2019

The anti-fatigue effect was investigated of the probiotic supplement, OM-X®, on forced swimming capacity in mice. Mice were administered either vehicle (distilled water; DW) or OM-X® (85 mg/kg body weight) by gavage for 4 weeks. Forced swimming tests were conducted weekly using the Ishihara-modified Matsumoto swimming pool. The endurance swimming time of the final forced swimming exercise in mice fed with OM-X® group showed an approximately 2-fold increase compared with the vehicle control group. Biomedical parameters, including blood lactate, blood superoxide dismutase (SOD) activity, serum triacylglycerol (TG), hepatic total lipids (TL), TG and phospholipid (PL) were significantly lower in mice fed with OM-X® than those in the vehicle control group. Furthermore, the mRNA expression levels of carbamoyl phosphate synthetase 1 (Cps1) and arginase 1 (Arg1), in the urea cycle, were increased by OM-X® feeding. Thus, our findings suggest promotion of lipid metabolism and up-regulation of the urea cycle, at least in part, for the anti-fatigue effect mediated by OM-X®.
Essential Oils of Morus alba and M. nigra Leaves: Effect of Drying on the Chemical Composition
Authors: Radulović Niko S. , Miljković Vojkan M. , Mladenović Marko Z. , Nikolić Goran S.
Published: March 2019

Detailed GC and GC/MS analyses of essential-oil samples obtained by hydrodistillation of Morus alba L. and M. nigra L. leaves (four samples) allowed the identification of 131 constituents representing 95.1 – 96.4% of the total GC peak areas. The most abundant compounds classes were alkanes, diterpenoids, carotenoid-derived compounds and fatty acid-related constituents with trans-phytol (7.9 – 71.2%), ( E,E)-geranyl linalool (0.2 – 8.0%), ( Z)-bovolide (8.1%) and n-chain alkanes (in total, 17.5 – 52.4%) as the major constituents of the analyzed samples. In general, there were only quantitative differences noted between M. nigra essential oils from fresh and dry leaves. The most discernable changes included a variation in the content of the major constituents (e.g. the relative amount of trans-phytol and the total amount of alkanes decreased by 5.8% and ≈ 2%, respectively, while that of ( E,E)-geranyl linalool increased by 7.8%). On the other hand, the composition of M. alba essential oil was much more significantly affected by the drying process. The highest quantitative differences were noted for trans-phytol, geranyl acetone, and all isomers of 4,6,8-megastigmatrien-3-one. Also, a rare plant metabolite, ( Z)-bovolide, characteristic of leaf senescence, was only identified (8.1%) in the essential oil of M. alba dried leaves.
Chemical Composition and Antibacterial Activity of the Essential Oil of Phellodendron lavallei
Authors: Lis Anna , Kowalska Weronika , Sienkiewicz Monika , Banaszczak Piotr
Published: March 2019

The essential oils from inflorescences, fruits and leaves of Phellodendron lavallei Dode were analyzed by GC, GC/MS and 1H NMR spectroscopy. About 100 compounds were identified. The principal components in the fruit oil were myrcene (47.7–52.0%) and limonene (38.4–40.9%), followed by germacrene D (1.2–3.2%) and ( E)-β-caryophyllene (2.4–2.9%). The inflorescence oil contained mainly myrcene (44.8%), limonene (43.2%) and ( E)-β-ocimene (4.1%). The main constituents of the leaf oil were limonene (26.7%) myrcene (22.1%), ( E,E)-α-farnesene (5.6%) and α-pinene (5.0%). The antibacterial activity was examined towards both Gram-positive and Gram-negative bacteria. The fruit oil showed weak activity against the bacteria tested.
Antimicrobial Potential of Rosmarinus officinalis Commercial Essential Oil in the Treatment of Vaginal Infections in Pregnant Women
Authors: Bogavac Mirjana A. , Karaman Maja A. , Suđi Jan J. , Radovanović Bojan B. , Janjušević Ljiljana N. , Ćetković Nenad B. , Tešanović Kristina D.
Published: March 2019

Treating inflammatory conditions such as vaginosis, vaginitis, and vulvovaginitis in pregnancy is a special problem due to limitations of available drugs. However, possible treatment options can be found also in naturally originated products, such as essential oils (EOs) of different plants. The aim of this study was to evaluate in vitro antimicrobial and toxic activities of the commercial EO of Rosmarinus officinalis L. ( Lamiaceae) against five Gram-positive and Gram-negative bacterial strains and two Candida strains obtained from pregnant women with vaginal infection. Gas chromatography-mass spectrometry of the tested EO revealed oxygenated monoterpenes to be the major ingredients, while microdilution assay showed the highest activity on Staphylococcus aureus II strain at 6.2 mg/mL. After 24 hours, toxicity was determined at 19.4 mg/mL on Artemia salina nauplii. The obtained results show this EO to be a promising alternative therapy for vaginal infections, although further toxicity and safety research is required.
Chemical Composition and Acaricidal Activity of Thymus algeriensis Essential Oil against Varroa destructor
Authors: Kouache Benmoussa , Brada Moussa , Saadi Abdelkader , Fauconnier Marie Laure , Lognay Georges , Heuskin Stephanie
Published: March 2019

The aim of the present study was to determine the chemical composition and evaluate the acaricidal activity of Thymus algeriensis essential oil (TAEO) against Varroa destructor. This ectoparasitic mite is a pest of the honey bee Apis mellifera. The essential oil from the aerial parts of T. algeriensis, obtained by hydrodistillation, was obtained in a yield of 2.8± 0.2%, w/w. The TAEO was analyzed by GC and GC/MS. Thirty-four compounds were identified, representing 99.3% of the oil. The main constituents were carvacrol (48.4%), γ-terpinene (14.9%), p-cymene (14.7%), and thymol (5.6%). Four lots were constituted at the level of an apiary in order to study the dynamics of the Varroa destructor and its host, Apis mellifera. After diagnosis by the biological method “install of diapers”, the lots were treated at different doses of TAEO (0.1, 0.3 and 0.5%). TAEO was sprayed on top of the hives. The results show that TAEO at 0.5% resulted in a decrease in the rate of infestation of Varroa destructor, causing a mortality rate of 32.6% without negative effect on the nesting of the queen. The essential oil of T. algeriensis could be used as a bioacaricidal agent.
Cereal Lignans, Natural Compounds of Interest for Human Health?
Authors: Zanella Isabella , Biasiotto Giorgio , Holm Finn , di Lorenzo Diego
Published: March 2019

Cereals are suggested to be the most important sources of lignan in the diets of western populations. Recent epidemiological studies show that European subpopulations in which the major source of lignans are cereals, display lower disease frequency regarding metabolic and cardiovascular diseases. The biological mechanisms of lignan are several. Beyond their antioxidant and anti-inflammatory actions at nutritional doses some lignans regulate the activity of specific nuclear receptors (NRs), such as the estrogen receptors (ERs), and also NRs that are central switches in glucose and fatty acid metabolism such as PPARα, PPARγ and LXRs, highlighting them as selective nuclear receptor modulators (SNRMs). These include enterodiol (END) and enterolactone (ENL), the metabolites produced by the gut microbiota from food lignans. The available knowledge suggests that given some additional research it should be possible to make ‘function' claims for a regular intake of lignans-rich foods related to maintaining a healthy metabolism.
Evaluation of Glaucine Content in Bulgarian Black Sea Coast Localities of Glaucium flavum Cranz. (Papaveraceae)
Authors: Doycheva Iva , Philipov Stefan , Stanilova Marina
Published: March 2019

The content of the alkaloid glaucine was evaluated in Glaucium flavum plants from seven localities along the Bulgarian Black sea coast during two consecutive years, in order to select those with highest glaucine content. Some fluctuations of glaucine content were observed during the two years, and in most of the localities the alkaloid was lower in 2015. Pomorie and Ahtopol maintained high percentages of glaucine in the dry plant material in the two investigated years, being 2.3% for Pomorie in 2014 and for Ahtopol in 2015. The lowest percentages of glaucine were recorded in the plant material from Shkorpilovtsi (0.9% and 0.6%, respectively in 2014 and 2015). Fluctuations in glaucine content were probably due to some abiotic factors as light, temperature, precipitation, soil substrate, salinity, etc.
Crataegus orientalis Leaves and Berries: Phenolic Profiles, Antioxidant and Anti-inflammatory Activity
Authors: Šavikin Katarina P. , Krstić-Milošević Dijana B. , Menković Nebojša R. , Beara Ivana N. , Mrkonjić Zorica O. , Pljevljakušić Dejan S.
Published: March 2019

The present study was designed to define the phenolic content, antioxidant and anti-inflammatory activity of Crateagus orientalis Pall. ex M. Bieb., traditionally used by local people in southern parts of F.Y.R. Macedonia. The presence and content of 7 phenolics in ethanolic extracts of leaves and berries were studied using HPLC-DAD, where the most dominant compounds were hyperoside, isoquercitrin and chlorogenic acid. The leaf extract was more effective as a DPPH radical scavenger (IC50 = 29.7 μg/g) than the berry extract, as well as in the relative reducing power on Fe3+. Anti-inflammatory potential was studied by means of cyclooxygenase-1 (COX-1) and 12-lipoxygenase (12-LOX) inhibitory activity; both extracts evinced activity. Furthermore, C. orientalis leaf extract showed a concentration dependent inhibition of COX-1 pathway products 12-HHT and TXB2, reaching IC50 values below the lowest applied concentration (68.9% and 55.2% of 12-HHT and TXB2 production inhibition, respectively, at concentration of 0.4 mg/mL). Although inhibitors such as acetylsalicylic acid and quercetin showed higher activity, this study demonstrates that the investigated extracts are potential anti-inflammatory agents.