bluuebunny/crossref_metadata_2025 huggingface dataset:
A New Naphthoquinone from Sinningia leucotricha (Gesneriaceae)
Authors: Verdan Maria Helena , Koolen Hector H. F. , Salvador Marcos José , Barison Andersson , Stefanello Maria Elida A.
Published: March 2019

A new naphthoquinone, 7,8-dimethoxydunnione (1), was isolated from Sinningia leucotricha (Hoehne) Moore tubers, together with four known compounds: 7-hydroxy-α-dunnione (2), 6-methoxy-7-hydroxy-α-dunnione (3), presilphiperfolan-9-ol (4), and betulinic acid (5). All compounds were identified by spectroscopic and mass spectrometric techniques and comparison with literature data. Compounds 2-5 are being reported for the first time in S. leucotricha.
Anti-allergic Inflammatory Activities of Compounds of Amomi Fructus
Authors: Choi Hyun Gyu , Je In-Gyu , Kim Geum Jin , Choi Hyukjae , Kim Sang Hyun , Kim Jeong Ah , Lee Seung Ho
Published: March 2019

Activity-guided isolation of compounds from the fruits of Amomum xanthioides resulted in the purification of fourteen phenolic compounds, 4-hydroxy-benzaldehyde (1), 3,4-dihydroxybenzaldehyde (2), 3,5-dimethoxy-4-methylbenzaldehyde (3), syringic aldehyde (4), benzoic acid (5), 3,4-dihydroxy benzoic acid (6), vanillic acid (7), 3-hydroxy-2-methoxybenzoic acid (8), o-vanillic acid (9), phenylacetic acid (10), tyrosol (11), pyrocatechol (12), 1,2,4,5-tetramethoxybenzene (13), and 3,3′,5,5′-tetramethoxybiphenyl-4,4′-diol (14). To evaluate the anti-allergic inflammatory activities of these compounds, we examined the inhibitory effects of the isolates (1-14) on histamine release and on the expressions of tumor necrosis factor (TNF)-α and interleukin (IL)–6 genes by using human mast cells. Of the tested compounds, 9, 11, and 13 suppressed histamine release from mast cells, and all isolates attenuated the expressions of the pro-inflammatory cytokines, TNF-α and IL-6 genes in human mast cells.
Hydropiperside, a new Sphingoglycolipid from Polygonum hydropiper
Authors: Sultana Rajia , Hossain Rashadul , Adhikari Achyut , Ali Zulfiqar , Choudhary Muhammad Iqbal , Zaman Muhammad Shahed
Published: March 2019

One new sphingoglycolipid, hydropiperside, along with two known compounds, flaccidine and quercetin were isolated from the methanolic extract of Polygonum hydropiper. Elucidation of structures was achieved by NMR (1D and 2D) data, mass (EI and FAB) spectroscopy and chemical means.
Synthetic Studies of Enacyloxins: A Series of Antibiotics Isolated from Frateuria sp. W-315: C1′-C8′ and C9′-C15′ Fragments
Authors: Saito Aki , Igarashi Wataru , Furukawa Hiroyuki , Hoshikawa Hiroki , Yamada Teiko , Kuwahara Shigefumi , Kiyota Hiromasa
Published: March 2019

Synthetic studies of enacyloxins (ENXs), a series of yellow-colored, polyene-polyol antibiotics produced by Frateuria sp. W-315, are described. The C1′-C8′ polyene fragments were prepared using successive Wittig reactions. The C9′-C15′ and C10′-C15′ fragments were constructed from ( S)-isopropylideneglyceraldehyde using Yamaguchi's nucleophilic substitution reaction of acetylide to epoxide, and/or Marshall's allenylindium mediated reaction as the key steps.
Chemical Composition of the Essential Oil of Gynoxys meridana from Mérida, Venezuela
Authors: Hernández Johanna , Rojas-Fermin Luis B. , Amaro-Luis Juan , Pouységu Laurent , Quideau Stéphane , Usubillaga Alfredo
Published: March 2019

The volatile components from the fresh leaves of Gynoxys meridana Cuatrec. were obtained by hydrodistillation and analyzed by GC/MS. A total of 25 compounds, representing 99.3% of the oil, were identified. The dominant compounds were γ-curcumene (31.9%), fukinanolide (22.3%), β-pinene (9.5%), α-phellandrene (7.1%) and α-pinene (5.7%).
Chemical Composition and Anti-mildew Activities of Essential Oils from Different Parts of Michelia compressa var. formosana
Authors: Su Yu-Chang , Hsu Kuang-Ping , Wang Eugene I-Chen , Ho Chen-Lung
Published: March 2019

In this study, anti-mildew activities of the essential oils of the leaves, wood, twigs, flowers, and their constituents from Michelia compressa var. formosana were evaluated in vitro against 7 mildew fungi. The main compounds responsible for the anti-mildew activities were isolated and identified. The essential oils from the fresh leaves, wood, twigs, and flowers of M. compressa var. formosana were isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC-FID and GC-MS. The essential oil yield from the flowers was the highest, and the oils obtained from the 4 parts of the tree were composed mainly of sesquiterpenoids. The leaf oil consisted primarily of α-cadinol (18.9%) and germacrene D (18.5%); the twig oil's main constituent was α-cadinol (19.1%); the wood oil's major components were α-cadinol (25.7%) and β-eudesmol (20.2%); and the flower oil contained α-cadinol (11.4%). Comparing the anti-mildew activities of the oils suggested that wood oil was the most effective. Further fractionation of the wood oil produced α-cadinol, β-eudesmol, τ-cadinol, and elemol. The 4 compounds exhibit very strong anti-mildew activities, and these in descending order are α-cadinol, elemol, β-eudesmol, and τ-cadinol. For the anti-mildew activities of the wood oil, the active source compounds were determined to be α-cadinol, elemol, β-eudesmol, and τ-cadinol.
Comparative Analysis of Two DOPA Dioxygenases from Phytolacca americana
Authors: Takahashi Kana , Yoshida Kazuko , Sakuta Masaaki
Published: March 2019

The comparative analysis of two Phytolacca americana DOPA dioxygenases (PaDOD1 and PaDOD2) that may be involved in betalain biosynthesis was carried out. The recombinant protein of PaDOD1 catalyzed the conversion of DOPA to betalamic acid, whereas DOD activity was not detected in PaDOD2 in vitro. The role of DOD genes is discussed in the evolutionary context using phylogenetic analysis, suggesting that DOD might have been duplicated early in evolution and that accumulation of base substitutions could have led to the different characteristics of DODs within the betalain-producing Caryophyllales.
Biochemical Analysis of Phytolacca DOPA Dioxygenase
Authors: Takahashi Kana , Yoshida Kazuko , Yura Kei , Ashihara Hiroshi , Sakuta Masaaki
Published: March 2019

The biochemical analysis of Phytolacca americana DOPA dioxygenases (PaDOD1 and PaDOD2) was carried out. The recombinant protein of PaDOD1 catalyzed the conversion of DOPA to betalamic acid, whereas DOD activity was not detected in PaDOD2 in vitro. While the reported motif conserved in DODs from betalain-producing plants was found in PaDOD1, a single amino acid residue alteration was detected in PaDOD2. A mutated PaDOD1 protein with a change of 177 Asn to Gly showed reduced specific activity compared with PaDOD1, while DOPA dioxygenase activity was not observed for a mutated PaDOD2 protein which had its conserved motif replaced with that of PaDOD1. A three-dimensional (3D) structural model of PaDOD1 and PaDOD2 showed that the conserved motif in DODs was located in the N-terminal side of a loop, which was found close to the putative active site. The difference in stability of the loop may affect the enzymatic activity of PaDOD2.
Cyanamide Phytotoxicity in Soybean (Glycine max) Seedlings involves Aldehyde Dehydrogenase Inhibition and Oxidative Stress
Authors: Maninang John S. , Okazaki Shin , Fujii Yoshiharu
Published: March 2019

The phytotoxic effect of the allelochemical cyanamide has been well-documented yet the underlying mechanism for this phenomenon has not been fully characterized. Cognizant of the putative inhibitory effect of cyanamide on aldehyde dehydrogenases (ALDHs), we hereby show that the capacity of mitochondrial preparations from cyanamide-treated soybean seedlings to oxidize acetaldehyde and succinic-semialdehyde was dose-dependently reduced to at most 55% and 70%, respectively. Cyanamide-treated plants exhibited oxidative stress (i.e. increased lipid peroxidation and H2O2 accumulation) that was exacerbated upon exposure to UV-A – symptoms reminiscent of ALDH and succinic-semialdehyde dehydrogenase (SSADH) knock-out Arabidopsis mutants. We suggest that the inhibition of mitochondrial ALDH and SSADH may be a contributory mechanism to the burst in oxidative stress mediated by cyanamide.
Allelopathy in a Leguminous Mangrove Plant, Derris indica: Protoplast Co-culture Bioassay and Rotenone Effect
Authors: Inoue Aya , Mori Daisuke , Minagawa Reiko , Fujii Yoshiharu , Sasamoto Hamako
Published: March 2019

To investigate allelopathic activity of a leguminous mangrove plant, Derris indica, the ‘Protoplasts Co-culture Method’ for bioassay of allelopathy was developed using suspension culture. A suspension culture was induced from immature seed and sub-cultured in Murashige and Skoog's (MS) basal medium containing 10 μM each of 2,4-dichlorophenoxyacetic acid (2,4-D) and 6-benzyladenine (BA). The protoplasts were isolated using the separate wells method with 2% each of Cellulase RS, Driselase 20 and Macerozyme R10 in 0.4 M mannitol solution. Protoplast cultures of D. indica revealed that high concentrations of cytokinins, BA and thidiazuron, were effective for cell divisions. The co-cultures of D. indica protoplasts with recipient lettuce protoplasts using 96 multi-well culture plates were performed in MS basal medium containing 0.4 M mannitol solution and 1 μM 2,4-D and 0.1 μM BA. The protoplast density of D. indica used in co-culturing varied from 6 × 103 - 105 / mL. Very strong inhibitory allelopathic effects of D. indica protoplasts on lettuce protoplast growth were found. A similar strong inhibitory allelopathic activity of dried young leaves on lettuce seedling growth was also observed by using the sandwich method. Rotenone, which is a component of Derris root, dissolved in DMSO, was highly inhibitory on the growth of lettuce protoplasts in culture and this could be one of the causes of the strong allelopathic activity of D. indica.
neo-Clerodane Diterpenoids from Ajuga macrosperma var. breviflora
Authors: Castro Amaya , Coll Josep , Pant Anil K. , Pakrash Om
Published: March 2019

Six new naturally occurring ajugarin-like neo-clerodane diterpenoids, ajugaflorins A-F, along with six known compounds [the parent ajugarin I, ajugalides B and C, ajugamarin F4, ajugamacrin E, and ajugatakasin B] were isolated from A. macrosperma var. breviflora. The structures were elucidated by extensive NMR spectroscopic and MS analyses and comparison with data previously reported.
Three New C20-Diterpenoid Alkaloids from Aconitum tanguticum var. trichocarpum
Authors: Zhang Zhong-Tang , Liu Xiao-Yu , Chen Dong-Lin , Wang Feng-Peng
Published: March 2019

Continuous investigations on the whole herbs of Aconitum tanguticum var. trichocarpum led to the isolation of three new C20-diterpenoid alkaloids trichocarpisines A–C (1–3). Their structures were elucidated on the basis of extensive interpretation of the spectroscopic data.
Oleanane-type Triterpene Saponins from Glochidion glomerulatum
Authors: Thu Vu Kim , Thang Nguyen Van , Nhiem Nguyen Xuan , Anh Hoang Le Tuan , Yen Pham Hai , Minh Chau Van , Kiem Phan Van , Kim Nan Young , Park Seon Ju , Kim Seung Hyun
Published: March 2019

Two new oleanane-type triterpene saponins, named glomeruloside I (1) and glomeruloside II (2), were isolated from the leaves of Glochidion glomerulatum (Miq.) Boerl. Their structures were determined by extensive spectroscopic methods, including 1D- and 2D-NMR, MS data, and chemical methods.
Increased Oxidative Stress in Cultured 3T3-L1 Cells was Attenuated by Berberine Treatment
Authors: Dong Shi-Fen , Yasui Naomi , Negishi Hiroko , Kishimoto Aya , Sun Jian-Ning , Ikeda Katsumi
Published: March 2019

The 3T3-L1 cell line is one of the most well-characterized and reliable models for studying adipocytes. Increased oxidative stress in accumulated fat was found in 3T3-L1 cells. Berberine, an isoquinoline alkaloid, could suppress fat deposition in 3T3-L1 cells; however, whether berberine suppresses increased oxidative stress is not well known. In this study, we observed the effect of berberine on increased oxidative stress in 3T3-L1 cells. 3T3-L1 cells were cultured and treated with berberine (5–20μM) from day 3 to day 8. We confirmed that berberine markedly inhibited fat accumulation and lipid droplets in 3T3-L1 adipocytes and decreased triglyceride content. Berberine inhibited increased oxidative stress in 3T3-L1 cells by suppressing reactive oxygen species (ROS) production, and increased glutathione peroxidase (GPx) gene expression and GPx activity. Berberine also markedly reduced adipokines secreted by adipocytes, including leptin and resistin.
Clovamide and Flavonoids from Leaves of Trifolium pratense and T. pratense subsp. nivale Grown in Italy
Authors: Tava Aldo , Pecio Łukasz , Stochmal Anna , Pecetti Luciano
Published: March 2019

The phenolic content and composition in leaves of Trifolium pratense (red clover) and T. pratense subsp. nivale (snow clover) grown in Italy were evaluated by means of ultraperformance liquid chromatography (UPLC) coupled with photodiode array and mass spectrometry detectors. Compound identification was based on UV and MS data comparing results with those of reference compounds. Quantitative evaluation of all detected compounds was based on calibration curves obtained with available standards. Several phenolics were identified in both extracts, including clovamide, flavonols and isoflavones as their glycosilated and malonated derivatives. The total phenolic content was higher in red clover (53.7 ± 2.2 mg/g dry weight) than in snow clover (44.4 ± 4.9 mg/g dry weight). Red clover contained higher amounts of clovamide and isoflavones (15.6 ± 0.6 and 24.6 ± 1.6 mg/g dry weight, respectively) than snow clover (8.2 ± 0.1 mg/g and 16.9 ± 0.4 mg/g dry weight, respectively), while flavonols were quantified almost in the same amount in both extracts (13.2 ± 0.6 mg/g and 15.8 ± 0.6 mg/g dry weight in red clover and snow clover, respectively). Red clover was characterized by the presence of quercetin, formononetin and biochanin A derivatives as the most abundant flavonoids, whereas snow clover was characterized by higher amounts of quercetin and prunetin derivatives. This investigation, conducted for the first time on phenolics from T. pratense subsp. nivale, revealed the presence in this plant of several flavonoid derivatives the same as in T. pratense. The higher amount of prunetin in snow clover suggest a possible role of this isoflavone as a chemotaxonomic marker for this subspecies. Moreover, snow clover may represent an interesting new source of natural isoflavones with a different concentration pattern than in red clover.
Metabolite Fingerprinting of Eugenia jambolana Fruit Pulp Extracts using NMR, HPLC-PDA-MS, GC-MS, MALDI-TOF-MS and ESI-MS/MS Spectrometry
Authors: Sharma Ram Jee , Gupta Ramesh C. , Bansal Arvind Kumar , Singh Inder Pal
Published: March 2019

Eugenia jambolana, commonly known as ‘jamun’ or Indian blackberry, is an important source of bioactive compounds. All parts of the plant like stem bark, leaves, flower, fruit pulp and seeds are traditionally used for many diseases. Metabolite profiling in medicinally important plants is critical to resolve the problems associated with standardization and quality control. Metabolite profiling of the fruit pulp of Jamun was performed by NMR, HPLC, MS, GC-MS and MALDI-TOF mass spectrometry. These hyphenated techniques helped in the identification of 68 chemically-diverse metabolites of the fruit pulp. These include anthocyanins, anthocyanidins, sugars, phenolics and volatile compounds. Five extracts of fruit pulp were prepared i.e. hexane, chloroform, ethylacetate, butanol and aqueous methanolic. Twenty-five metabolites identified and quantified in the n-butanol and aqueous-methanolic extracts of ripe jamun fruit by qNMR. LC-PDA-MS and MALDI-TOF spectrometry helped in deciphering thirty-nine metabolites out of which thirteen were quantified.
Phthalide Anions in Organic Synthesis. A Direct Total Synthesis of Furomollugin
Authors: Kraus George A. , Dong Pengfei
Published: March 2019

Furomollugin was synthesized in three steps from commercially available starting materials using phthalide annulation chemistry.
New Sesquiterpene Glycosides from the Leaves of Eriobotrya japonica
Authors: Ao Xiancan , Zhao Lei , Lü Han , Ren Bingru , Wu Hankui , Chen Jian , Li Weilin
Published: March 2019

One new sesquiterpene glycoside, named nerolidol-3- O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (1), along with one novel natural product nerolidol-3- O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (2) and two known sesquiterpene glycosides (3-4), were isolated from the leaves of Eriobotrya japonica (Thunb.) Lindl.. Their structures were elucidated on the basis of 1D, 2D NMR and HR-MS data. The chemotaxonomic significance of this type of constituents was discussed.
Isolation and Fast Selective Determination of Nor-abietanoid Diterpenoids from Perovskia atriplicifolia Roots Using LC-ESI-MS/MS with Multiple Reaction Monitoring
Authors: Ślusarczyk Sylwester , Topolski Jakub , Domaradzki Krzysztof , Adams Michael , Hamburger Matthias , Matkowski Adam
Published: March 2019

In the first part of this study we extracted, isolated, and identified the main diterpenoid constituents from the roots of a Central Asian medicinal and ornamental plant - Perovskia atriplicifolia Benth. Eight major nor-abietanoid pigments were obtained using NP silica gel column chromatography and preparative RP-HPLC: cryptotanshinone, 1-hydroxycryptotanhinone, miltirone, 1-oxomiltirone, tanshinone IIa, 1,2 didehydrotanshinone IIa, 1,2 didehydromiltirone, the non-quinone diterpenoid - arucadiol, as well as rosmarinic acid as a main phenolic compound. Secondly, we used the obtained compounds for fast and selective determination of the main diterpenes present in P. atriplicifolia root extract. After extraction with n-hexane, the quantitative analysis was carried out by LC–MS/MS with a triple quadrupole (qQq) mass detector without any prior clean-up step. Identification of the diterpenes was confirmed by multiple reaction monitoring (MRM) using the most representative transitions from the precursor ions, while the most sensitive transitions were used for quantification in a 19-minute run. Most of the isolated and analyzed compounds had not been previously reported from this species. This easily cultivated plant is a promising source of several pharmacologically valuable abietanoid diterpenoids.
A Validated, Rapid HPLC-ESI-MS/MS Method for the Determination of Lycopsamine
Authors: Jedlinszki Nikoletta , Csupor Dezső
Published: March 2019

The aim of the present work was to develop and validate an HPLC-MS/MS method for the determination of a major pyrrolizidine alkaloid of comfrey (lycopsamine) in aqueous samples as a basis for the development of a method for the determination of absorption of lycopsamine by human skin. A linear calibration curve was established in the range of 1.32–440 ng. The intraday precision during the 3-day validation period ranged between 0.57 and 2.48% while the interday precision was 1.70% and 1.95% for quality control samples. LOD was 0.014 ng and recovery was above 97%. The lycopsamine content of the samples stored for 9 and 25 days at 22°C, 10°C and −25°C did not vary. These results underline the good repeatability and accuracy of our method and allow the analysis of samples with very low lycopsamine content.
Toxicity of Cephalaria Species and their Individual Constituents against Aedes aegypti
Authors: Sarikahya Nazli Boke , Kayce Peyker , Tabanca Nurhayat , Estep Alden S. , Becnel James J. , Khan Ikhlas A. , Kirmizigul Suheyla
Published: March 2019

Crude acetone and ethanol extracts of the aerial parts of 21 Cephalaria species collected from Turkey were investigated for larvicidal and adult topical activity against Aedes aegypti. The ethanol extracts from C. elazigensis var. purpurea, C. anatolica, and C. elmaliensis possessed the highest mortality against first instar Ae. aegypti larvae. Luteolin-7 -O-β-D-glycoside (1), isolated from C. elmaliensis ethanol extract, demonstrated 33% and 53% mortality at 0.1 μg/mL concentration against first instar ORL (susceptible) and PR (pyrethroid resistant) strains, respectively. C. scoparia acetone extract showed 100% mortality against adult Ae. aegypti. From this extract compounds 2-8 were isolated. Compound 2 (isoorientin) possessed the highest toxicity with 31.7% and 65% mortality at a 10 μg/mL concentration against adult ORL and PR strains, respectively. This is the first screening report of potential insecticides from Cephalaria species against the yellow fever mosquito, Ae. aegypti, and the active compounds (1 and 2) could lead to the development of a new class of insecticide.
Constituents of Bulbs of three Species of the Hyacinthaceae (Hyacinthoideae): Eucomis vandermerwei, E. zambesiaca and Resnova humifusa
Authors: Sihra Jaspreet K. , Thumser Alfred E. , Langat Moses K. , Crouch Neil R. , Mulholland Dulcie A.
Published: March 2019

Phytochemical analyses of the bulbs of Eucomis vandermerwei and E. zambesiaca yielded homoisoflavonoids and triterpenoid derivatives. A new (17 S*,23 S*)-epoxy-3β,15β,29-trihydroxy-27-norlanost-8-en-24-one) was isolated from E. zambesiaca. Resnova humifusa yielded homoisoflavonoids, and a tetrahydropyran derivative, 2-methyl-3-(4 S*,5 R*,7 S*-trihydroxy-8 S*-hydroxymethyltetrahydro-6H-4-pyranyl)-2-propenoic acid. All compounds were assayed for COX-2 inhibition of cyclooxygenase; 3,5,7-trihydroxy-3-(4′-methoxybenzyl)-4-chromanone was found to have significant activity.
Effect of Hinoki and Meniki Essential Oils on Human Autonomic Nervous System Activity and Mood States
Authors: Chen Chi-Jung , Kumar K. J. Senthil , Chen Yu-Ting , Tsao Nai-Wen , Chien Shih-Chang , Chang Shang-Tzen , Chu Fang-Hua , Wang Sheng-Yang
Published: March 2019

Meniki ( Chamecyparis formosensis) and Hinoki ( C. obtusa) are precious conifers with excellent wood properties and distinctive fragrances that make these species popular in Taiwan for construction, interiors and furniture. In the present study, the compositions of essential oils prepared from Meniki and Hinoki were analyzed by gas chromatography-mass spectrometry (GC/MS). Thirty-six compounds were identified from the wood essential oil of Meniki, including 5-cadinene, y-cadinene, 5-cadinol, α-muurolene, calamenene, linalyl acetate and myrtenol; 29 compounds were identified from Hinoki, including α-terpineol, α-pinene, 8-cadinene, borneol, terpinolene, and limonene. Next, we examined the effect of Meniki and Hinoki essential oils on human autonomic nervous system activity. Sixteen healthy adults received Meniki or Hinoki by inhalation for 5 min, and the physiological and psychological effects were examined. After inhaling Meniki essential oil, participant's systolic blood pressure and heart rate (HR) were decreased, and diastolic blood pressure increased. In addition, sympathetic nervous activity (SNS) was significantly decreased, and parasympathetic activity (PSNS) was significantly increased. On the other hand, after inhaling Hinoki essential oil, systolic blood pressure, heart rate and PSNS were decreased, whereas SNA was increased. Indeed, both Meniki and Hinoki essential oils increased heart rate variability (HRV) in tested adults. Furthermore, in the Profile of Mood States (POMS) test, both Meniki and Hinoki wood essential oils stimulated a pleasant mood status. Our results strongly suggest that Meniki and Hinoki essential oils could be suitable agents for the development of regulators of sympathetic nervous system dysfunctions.
Chemical Composition and in vitro Antibacterial Activity of the Essential Oil of Verbesina negrensis from the Venezuelan Andes
Authors: Mora Flor D. , Rojas Yesenia L. , González Viviana , Velasco Judith , Díaz Tulia , Ríos Nurby , Rojas-Fermin Luis B. , Carmona Juan , Silva Bladimiro , Nieto Marcelo
Published: March 2019

The composition and antimicrobial activity of the essential oil from Verbesina negrensis Steyerm. leaves is reported. Analysis was performed by GC/MS. Major constituents were α-pinene (43.1%), α-humulene (13.8%), δ-cadinene (8.1%), limonene (4.6%) and bicyclogermacrene (4.2%). The essential oil showed in vitro activity against the Gram-positive bacteria Staphylococcus aureus ATCC 25923 and Enterococcus faecalis ATCC 29212 (MIC 500 and 350 μL/mL respectively).
Damarane-type Saponins from Gynostemma Longipes and their Cytotoxic Activity
Authors: Anh Pham Tuan , Ky Pham Thanh , Cuc Nguyen Thi , Nhiem Nguyen Xuan , Yen Pham Hai , Ngoc Tran Minh , Anh Hoang Le Tuan , Tai Bui Huu , Trang Do Thi , Van Minh Chau , Van Kiem Phan
Published: March 2019

Two new damarane- type saponins, named gylongiposides II-III (1 and 2), along with one known compound, (23 S)-3β,20ζ,21ζ-trihydroxy-19-oxo-21,23-epoxydammar-24-ene 3- O-α-L-rhamnopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-α-L-arabinopyranoside, were isolated from the leaves of Gynostemma longipes C.Y.Wu. Their structures were determined by 1D- and 2D-NMR and HR-ESI-MS spectra. Compounds 1–3 exhibited moderate activity against four human cancer cell lines, A-549, HT-29, OVCAR, and MCF-7, with IC50 values ranging from 9.8 ± 2.1 to 49.6 ± 2.6 μM.
Effect of Quercetin on Cell Cycle and Cyclin Expression in Ovarian Carcinoma and Osteosarcoma Cell Lines
Authors: Catanzaro Daniela , Ragazzi Eugenio , Vianello Caterina , Caparrotta Laura , Montopoli Monica
Published: March 2019

Resistance to chemotherapeutic drugs is a major problem in cancer treatment. The search for new interventions able to overcome this resistance may involve compounds of natural origin, such as flavonoids, ubiquitously present in many foods. In the present study, the cytotoxic effects and cell cycle modulation of the flavonoid quercetin were investigated in ovarian carcinoma (SKOV3) and osteosarcoma (U2OS) human cell lines and in their cisplatin (CDDP)-resistant counterparts (SKOV3/CDDP and U2OSPt cells, respectively). Quercetin (10–50 μM) caused evident changes in the distribution of cell cycle phases in the CDDP-resistant SKOV3/CDDP ovarian cell line. The levels of cyclin D1 and cyclin B1 were determined by means of Western blot in all cell lines incubated with quercetin (50 μM) for 48 hours. The cyclin D1 expression was significantly decreased following the treatment with quercetin in SKOV3 and U2OSPt cells, but not in SKOV3/CDDP and U2OS cells. The reduction of cyclin D1 level could be linked to the G1/S phase alteration found in quercetin-treated cells. Although cyclin B1 is required for G2/M phase, and despite our observation that quercetin influenced the G2/M phase of cell cycle, the flavonoid did not affect cyclin B1 levels in all cell lines, indicating the involvement of other possible mechanisms. These results suggest that quercetin, exceeding the resistance to CDDP, might become an interesting tool to evaluate cytotoxic activity in combination with chemotherapy drugs.
A Novel C21 Cyclopentenone Derivative from Cipadessa Cinerascens
Authors: Zhang Jing , Chang Yao-Wen , Yuan Chun-Mao , Zhang Fan , Di Ying-Tong , Hao Xiao-Jiang
Published: March 2019

A new C21 cyclopentenone derivative, Cipacyclonone (1), was isolated from the leaves of Cipadessa cinerascens. Its structure was elucidated on the basis of spectroscopic analysis, including extensive 1D- and 2D-NMR techniques. Compound 1 showed strong cytotoxicity activity against HL-60 and A-549 cell lines, with IC50 values of 1.2 and 3.0 μM, respectively.
Effects on MC3T3-E1 Cells and In Silico Toxicological Study of Two 6-(Propan-2-yl)-4-methyl-morpholine-2,5-diones
Authors: Vukelić-Nikolić Marija , Kolarević Ana , Tomović Katarina , Yancheva Denitsa , Cherneva Emiliya , Najman Stevo , Šmelcerović Andrija
Published: March 2019

Recently, we found that two cyclodidepsipeptides, 3,6-di-(propan-2-yl)-4-methyl-morpholine-2,5-dione (1) and 3-(2-methylpropyl)-6-(propan-2-yl)-4-methyl-morpholine-2,5-dione (2), are excellent inhibitors of xanthine oxidase. In order to obtain more information about the toxicological potential of compounds 1 and 2 on bone cells, the current study was designed to evaluate the effect of these compounds on viability and proliferation of MC3T3-E1 cells. Compound 1 showed neither cytotoxic nor stimulatory effect on cell viability, while compound 2 showed a slight stimulatory effect on cell viability. Both studied compounds showed slight stimulatory effects on proliferation of MC3T3-E1 cells, in a dose dependent manner. Additionally, an in silico toxicological study of compounds 1 and 2 was performed, and the results indicate that they have a good probability of safe biological intake.
Genotoxicity and Antigenotoxicity Studies of Traditional Medicinal Plants: How Informative and Accurate are the Results?
Authors: Verschaeve Luc
Published: March 2019

Genotoxicity and antigenotoxicity studies of (traditional medicinal) plants are important from a risk assessment point of view and in the search for new medication against, for example, cancer. It is clear yet that attention should be paid to a number of aspects that may influence the outcome of a study and to which often no or insufficient attention is paid. A short overview is given of such aspects that deserve more attention.
A Synthetic Butenolide Diterpene is now a Natural Product Isolated from Metaporana sericosepala, a Plant from the Madagascar Dry Forest [1a]
Authors: Presley Christopher C. , Rakotondraibe L. Harinantenaina , Brodie Peggy J. , Callmander Martin W. , Randrianaivo Richard , Rasamison Vincent E. , Rakotobe Etienne , Kingston David G. I.
Published: March 2019

Antiproliferative bioassay-guided fractionation of the ethanolic extract of the endemic Madagascan plant Metaporana sericosepala led to the first natural product isolation of a butenolide diterpene, which was synthesized during an anti-inflammatory study in 1988. The structure of the compound was elucidated as 3-homofarnesyl-4-hydroxybutenolide (1) by analysis of its spectroscopic data, including 1D- and 2D-NMR data and chemical evidence. The once synthetic compound can now also be considered as a natural product. Compound 1 had modest antiproliferative activity towards the A2780 ovarian cancer cell line with an IC50 value of 8 μM.
Sagitol D, a New Thiazole Containing Pyridoacridine Alkaloid from a Vietnamese Ascidian
Authors: Utkina Natalia K.
Published: March 2019

A new thiazole containing pyridoacridine alkaloid, named sagitol D (1), and five known alkaloids kuanoniaminesA (2), C (3), D (4), E (5), and F (6), have been isolated from an unidentified Vietnamese ascidian. The structure of the new compound was established from NMR spectroscopic data. Kuanoniamines C, D, E, and F showed moderate antioxidant activity in the DPPH (IC50 36 μM) and ABTS assays (TE = 0.5), while sagitol D showed weak activity (IC50 92 μM; TE = 0.10), and kuanoniamine A was inactive.
A New Flavanone from the Leaves of Chromolaena odorata
Authors: Emani Lakshmareddy , Ravada Suryachandrarao , Meka Bharani , Garaga Machiraju , Golakoti Trimurtulu
Published: March 2019

Chromolaena odorata (Syn: Eupatorium odoratum) is a perennial plant belonging to the Asteraceae family. Extracts of C. odorata have shown strong anti-oxidant and moderate anti-adipogenenesis activities. Detailed phytochemical investigation of C. odorata led to the isolation of 21 secondary metabolites, which include a new flavanone (3), and a chalcone, 3,2′-dihydroxy-4,4′,5′,6′-tetramethoxychalcone (2), reported for the first time from a natural source, besides three known compounds 1, 4 and 5, all of which are reported for the first time from C. odorata. Some of these compounds exhibited potent anti-oxidant and anti-adipogenesis activities and these may be partly responsible for the activity of the extract.
Inhibitory Effect of Isoflavones from Erythrina poeppigiana on the Growth of HL-60 Human Leukemia Cells through Inhibition of Glyoxalase I
Authors: Hikita Kiyomi , Yamada Saori , Shibata Rina , Katoh Miyako , Murata Tomiyasu , Kato Kuniki , Tanaka Hitoshi , Kaneda Norio
Published: March 2019

It has been reported that many malignant human tissues, including breast, colon, and lung cancers, may show an elevated expression of glyoxalase I (GLO I). GLO I catalyzes the reaction to transform hemimercaptal, a compound formed from methylglyoxal (MG) and reduced glutathione, into S-D-lactoylglutathione, which is then converted to D-lactic acid by glyoxalase II. GLO I inhibitors are expected to be useful for inhibiting tumorigenesis through the accumulation of apoptosis-inducible MG in tumor cells. Here, we investigated the anti-proliferative activity of eight kinds of isoflavone isolated from Erythrina poeppigiana against the growth of HL-60 human leukemia cells from the viewpoint of GLO I inhibition. Of the compounds tested, the diprenyl isoflavone, isolupalbigenin, was shown to exhibit the highest anti-proliferative activity against HL-60 cells. Upon the treatment of HL-60 cells with isolupalbigenin, MG was significantly accumulated in the culture medium, and the caspase 3 activity of the cell lysate was elevated in a time-dependent manner. Thus, it is suggested that isolupalbigenin inhibits the enzyme GLO I, resulting in MG accumulation in the medium, and leading to cell apoptosis. Isolupalbigenin, with two prenyl groups in its A- and B-rings, might be expected to become a potent leading compound for the development of anticancer agents.
Biological Activity and Chemical Constituents of Essential Oil and Extracts of Murraya microphylla
Authors: Lv Hai-Ning , Zeng Ke-Wu , Liu Bing-Yu , Zhang Yun , Tu Peng-Fei , Jiang Yong
Published: March 2019

Murraya microphylla is the most closely related species to M. koenigii (Curry tree). Inspired by the traditional effects of M. koenigii, the antioxidant, anti-inflammatory, and cytotoxic activities of the essential oil and extracts of M. microphylla were evaluated for the first time. The light petroleum and chloroform extracts were found to be able to scavenge DPPH free radicals, inhibit linoleic acid peroxidation, and nitric oxide production, as well as to present cytotoxicity to the human cancer cell lines HepG2, Bel7402, Bel7403, and Hela, but the essential oil only showed moderate activities. Chemical analysis of the active extracts by LC-DAD-MSn indicated that carbazole alkaloids were the main constituents. GC-MS analysis of the essential oil resulted in identification of 91 constituents, representing 96.9% of the total oil, with ( E)-caryophyllene (18.4%) and terpinen-4-ol (12.6%) as the major constituents. These results demonstrate that M. microphylla has similar biological activities, as well as chemical constituents to M. koenigii, and the carbazole alkaloids were disclosed to be the main potential active components. A promising development as a flavor and potential therapeutic agent could thus be predicated for this plant.
Polyketides from an Endophytic Aspergillus fumigatus Isolate Inhibit the Growth of Mycobacterium tuberculosis and MRSA
Authors: Flewelling Andrew J. , Bishop Amanda L , Johnson John A. , Gray Christopher A.
Published: March 2019

The crude extract of Aspergillus fumigatus isolate AF3-093A, an endophyte of the brown algaFucus vesiculosus, showed significant antimicrobial activity in initial bioactivity screens. Bioassay-guided fractionation of the extract led to the isolation of flavipin, chaetoglobosin A and chaetoglobosin B, all of which inhibited the growth of Staphylococcus aureus, methicillin-resistant S. aureus and Mycobacterium tuberculosis H37Ra. The antimycobacterial activity of these compounds has not been previously reported.
Isoorientin, a Selective Inhibitor of Cyclooxygenase-2 (COX-2) from the Tubers of Pueraria tuberosa
Authors: Sumalatha Manne , Munikishore Rachakunta , Rammohan Aluru , Gunasekar Duvvuru , Kumar Kotha Anil , Reddy Kakularam Kumar , Azad Rajaram , Reddanna Pallu , Bodo Bernard
Published: March 2019

Bioassay-guided fraction of the methanol extract of the roots of Pueraria tuberose DC yielded puerarin, an isoflavone C-glycoside (PT-1), isoorientin, a flavone C-glycoside (PT-2) and mangiferin, a xanthone C-glycoside (PT-3). The extracts and the isolated compounds were screened for potent antiinflammatory components inhibiting the cyclooxygenases (COX-1 and COX-2) and 5-lipoxygenase (5-LOX), the target enzymes of inflammation, by employing spectroscopic/polorographic methods. Among these, isoorientin was found to be a potent inhibitorof COX-2with an IC50 value of 39 μM. Docking studies were carried out to understand the interactions of isorientin (PT-2) with COX-2. The structures of the isolates were determined by mass spectrometry and 2D-NMR techniques including HSQC, HMBC, NOESY and 1H-1H COSY experiments. Although isoorientin and mangiferin have been reported from several plant sources, this is the first report of their isolation from a Pueraria species.
Proliferative Constituents from the Leaves of Micromelum integerrimum
Authors: Hu Yuan-bin , Sun Jun-ying , Yu Tang-yun , Wang Jing-cheng , He Jin-shan , Zhou Yue-lai , Li Xian-wen
Published: March 2019

wo new compounds, 5- O-methyl-4-desmethyl-myricanol (1) and 6-formyl-5-isopropyl-3-hydroxymethyl-7-methyl-1H-indene (2), were isolated from the leaves of Micromelum integerrimum. Their structures were determined by spectroscopic methods. Additionally, compound 1 could stimulate the growth of NIH3T3 cells and promote cell migration. Compound 1 might exert its effects through increasing the protein expression of connective tissue growth factor.
Separation of Aeruginosin-865 from Cultivated Soil Cyanobacterium (Nostoc sp.) by Centrifugal Partition Chromatography combined with Gel Permeation Chromatography
Authors: Cheel José , Minceva Mirjana , Urajová Petra , Aslam Rabya , Hrouzek Pavel , Kopecký Jiři
Published: March 2019

Aeruginosin-865 was isolated from cultivated soil cyanobacteria using a combination of centrifugal partition chromatography (CPC) and gel permeation chromatography. The solubility of Aer-865 in different solvents was evaluated using the conductor-like screening model for real solvents (COSMO-RS). The CPC separation was performed in descending mode with a biphasic solvent system composed of water-n-BuOH-acetic acid (5:4:1, v/v/v). The upper phase was used as a stationary phase, whereas the lower phase was employed as a mobile phase at a flow rate of 10 mL/min. The revolution speed and temperature of the separation column were 1700 rpm and 25°C, respectively. Preparative CPC separation followed by gel permeation chromatography was performed on 50 mg of crude extract yielding Aer-865 (3.5 mg), with a purity over 95% as determined by HPLC. The chemical identity of the isolated compound was confirmed by comparing its spectroscopic data (UV, HRESI-MS, HRESI-MS/MS) with those of an authentic standard and data available in the literature.
Essential Oil Composition and Antibacterial Activity of Hyptis colombiana from the Venezuelan Andes
Authors: Flores Mayalin , Rojas Luis , Aparicio Rosa , Lucena Maria Eugenia , Usubillaga Alfredo
Published: March 2019

Hyptis colombiana is an aromatic shrub native to the Colombian and Venezuelan Andes. Aerial parts were collected in Mérida State at about 3100 m above sea level in February 2005, and May and October 2006. The essential oil was found to contain germacrene D and β-caryophyllene as main constituents (about 50%). The February 2005 and October 2006 oils were found to have antibacterial activity against Staphylococcus aureus, but not the May 2006 oil, probably due to the lack of some minor constituent.
Synthesis of the Furan Nucleus Promoted by Ytterbium Triflate
Authors: Taddeo Vito Alessandro , Genovese Salvatore , Epifano Francesco , Fiorito Serena
Published: March 2019

An efficient synthesis of differently substituted furans from acetylene dicarboxylates and β-dicarbonyl compounds is described. The furan nucleus was built by means of an Yb(OTf)3 catalyzed cycloaddition reaction yielding desired adducts in 91% – 98% yield.
Analysis of Organic Acids, Deacetyl Asperulosidic Acid and Polyphenolic Compounds as a Potential Tool for Characterization of Noni (Morinda citrifolia) Products
Authors: Bittová Miroslava , Hladůvková Dita , Roblová Vendula , Kráčmar Stanislav , Kubáň Petr , Kubáň Vlastimil
Published: March 2019

Organic acids, deacetyl asperulosidic acid (DAA) and polyphenolic compounds in various noni ( Morinda citrifolia L.) products (4 juices, 4 dry fruit powders and 2 capsules with dry fruit powder) were analyzed. Reversed-phase high-performance liquid chromatography (RP-HPLC) coupled with a variable wavelength detector (VWD) and electrospray ionization time-of-flight mass spectrometer (ESI-TOF MS) was applied for simultaneous analysis of organic acids (malic, lactic, citric and succinic acid) and DAA. An RP-HPLC method with diode-array detector (DAD) was developed for the analysis of polyphenolic compound content (rutin, catechin, quercitrin, kaempferol, gallic acid, caffeic acid and p-coumaric acid). The developed methods can contribute to better characterization of available noni products that is required from the consumers. In our study, we discovered significant dissimilarities in the content of DAA, citric acid and several phenolic compounds in some samples.
Combination of Antioxidants from Different Sources Could offer Synergistic Benefits: A Case Study of Tea and Ginger Blend
Authors: Makanjuola Solomon A. , Enujiugha Victor N. , Omoba Olufunmilayo S. , Sanni David M.
Published: March 2019

Tea and ginger are plants with high antioxidant potential. Combinations of antioxidants from different sources could also produce synergistic antioxidant effects. This study investigated the influence of solvent on antioxidant content of tea, ginger, and tea + ginger blends. Under the investigated extraction conditions, water was the most effective extraction solvent to maximise peroxide scavenging and iron chelating activity of tea, ginger, and their blends. Aqueous ethanol was the most effective solvent to maximise ABTS radical scavenging activity and ethanol was the best solvent to maximise DPPH radical scavenging activity. A good multivariate regression model that explains the relationship between the total flavonoid content of the extracts and their antioxidant activities was obtained (R2 and Q2 of 0.93 and 0.83, respectively). Extracts of tea-ginger blends exhibited synergistic effects in their ABTS and DPPH radical scavenging activity.
New Glycosides and Trypanocidal Metabolites from Vangueria edulis
Authors: Mohamed Shaymaa M. M. , Elokely Khaled M. , Bachkeet Enaam Y. , Bayoumi Soad A. L. , Carnevale Vincenzo , Klein Michael L. , Cutler Stephen J. , Ross Samir A.
Published: March 2019

A new iridoid glucoside, 10-methoxy apodanthoside (1), and a new monoterpene glycoside, (3S,6S)-cis linalool-3,7-oxide O-β-D-glucopyranosyl-(1′'→5′)-β-D-xylofuranoside (2), were isolated from V. edulis (Rubiaceae), along with eighteen known compounds (3–20), including monoterpenes, iridoid glycosides, and a lignin, which were encountered for the first time in the genus Vangueria,. The structural elucidation of the isolates was based on the analysis of spectroscopic (1D and 2D NMR) and HR-ESI-MS data. Detailed stereochemical studies of 1 and related iridoid glucosides (compounds 3, 4 and 8) were made by matching the calculated ECD peaks with the experimental ones. All isolates were tested for their antiprotozoal, antifungal, and antiplasmodial activities. Compounds 9, 15 and 16 showed good trypanocidal activities against Trypanosoma brucei brucei with IC50 values of 8.18, 9.02 and 7.80 μg/mL, respectively and IC90 values of >10, >10 and 9.76 μg/mL, respectively. Compound 16 showed a moderate activity against Candida glabrata with an IC50 value of 8.66 μg/mL. Compound 20 showed a weak antiplasmodial activity against chloroquine-sensitive (D6) and resistant (W2) Plasmodium falciparum with IC50 values of 3.29 (SI, >1.4) and 4.53 (SI, >1) μg/mL, respectively.
Bioassay-guided Isolation of Antiproliferative Triterpenoids from Euonymus alatus Twigs
Authors: Kang Hee Rae , Eom Hee Jeong , Lee Seoung Rak , Choi Sang Un , Kang Ki Sung , Lee Kang Ro , Kim Ki Hyun
Published: March 2019

Euonymus alatus (Celastraceae) has been used as an anticancer agent in Korean traditional medicine. However, the potential bioactive contributors to the anticancer effects have not been thoroughly studied. Our screening test revealed that the MeOH extract of E. alatus twigs exhibited significant cytotoxicity against A549, SK-OV-3, and SK-MEL-2 cell lines. A bioassay-guided separation of the MeOH extract of E. alatus twigs resulted in the isolation and identification of 14 triterpenes as main phytochemicals. The structures of the compounds were elucidated on the basis of spectroscopic evidence as lupeol (1), betulin (2), 3β,28,30-lup-20(29)-ene triol (3), lupenone (4), betulone (5), 28,30-dihydroxy-3-oxolup-20(29)-ene (6), messagenin (7), glut-5-en-3β-ol (8), maslinic acid (9), hederagenin (10), 3-oxo-11α-methoxyolean-12-ene (11), 3β-hydroxy-1-oxo-olean-12-en-28-oic acid (12), ursolic acid (13), and 2α-hydroxy-ursolic acid (14). Of these compounds, 3, 6–8, and 10–14 were isolated for the first time from this plant. All isolated triterpenoids had consistent antiproliferative activities against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines. Compounds 2, 5, and 7 showed significant cytotoxicity against all four cell lines tested, with IC50 values of 3.26–8.61 μM.
Two New Triterpenoidal Saponins from Roots of Pachystela msolo
Authors: Ache Roland N. , Tabopda Turibio K. , Yeboah Samuel O. , Ngadjui Bonaventure T.
Published: March 2019

Two new triterpenoidal saponins, pachystelanosides A (1) and B (2), and six known compounds have been isolated from the roots of Pachystela msolo. Their structures were elucidated on the basis of extensive 1D and 2D NMR studies (1H, 13C, DEPT, COSY, TOCSY, NOESY, HSQC, HMBC), and ESI-MS as 3- O-(β-D-glucopyranosyl-(1→2)-β-D-apiofuranosyl-(1→6)-β-D-glucopyranosyl)-28- O-(β-D-xylopyranosyl-(1→4)[α-L-rhamnopyranosyl-(1→2)]-α-L-arabino-pyranosyl)-hydroxyprotobassic acid (1) and 3- O-(β-D-glucopyranosyl-(1→2)-β-D-apiofuranosyl-(1→6)-β-D-glucopyranosyl)-28- O-(β-D-xylopyranosyl-(1→4)[α-L-rhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl)-7α-hydroxyprotobassic acid (2).
The Influence on LPS-Induced ROS Formation in Macrophages of Capelloside A, a New Steroid Glycoside from the Starfish Ogmaster capella
Authors: Ivanchina Natalia V. , Kicha Alla A. , Malyarenko Timofey V. , Kalinovsky Anatoly I. , Menchinskaya Ekaterina S. , Pislyagin Evgeny A. , Dmitrenok Pavel S.
Published: March 2019

A new steroid glycoside, capelloside A (1), was isolated from the ethanolic extract of the starfish Ogmaster capella along with the previously known coscinasteroside B (2). The structures of 1 was elucidated by extensive NMR and ESI-MS techniques as (24 S)-24- O-(3- O-methyl-β-D-xylopyranosyl)-5α-cholestane-3β,6β,8,15α,24-pentol 15- O-sulfate (1). Compounds 1 and 2 decreased intracellular ROS (reactive oxygen species) levels in murine macrophages of the RAW 264.7 cell line at induction by endotoxic lipopolysaccharide (LPS) from E. coli by 60% and 41%, correspondingly.
A New Isoflavone Apioglucoside from the Roots of Dalbergia spinosa
Authors: Radha Raja , Vasantha Vairathevar Sivasamy , Pitchumani Kasi
Published: March 2019

Targeting the discovery of novel natural products, the roots of Dalbergia spinosa Roxb has yielded a new isoflavone apioglycoside, 5-hydroxy-6-methoxy-3′,4′-methylenedioxy-7-[(6- O-β-D-apiofuranosyl-β-D-glucopyranosyl) oxy]isoflavone (dalspinin-7- O-β-D-[apiofuranosyl (1→6)] glucopyranoside) (1), together with the known isoflavones, dalspinin (2), dalspinosin (3) and caviunin (4). Their structures were elucidated on the basis of extensive spectral and chemical evidence. To the best of our knowledge, this is the first report of the occurrence of an apioglucoside of dalspinin in Nature.