bluuebunny/crossref_metadata_2025 huggingface dataset:
Synthesis of Polyhydroxylated Aminonaphthazarins Related to Natural Pigments
Authors: Melman Galina I. , Pokhilo Natalia D. , Atopkina Lyubov N. , Denisenko Vladimir A. , Anufriev Victor Ph.
Published: March 2019

Amino analogs of echinochrome and ethylmompain, metabolites of sea urchins Scaphechinus mirabilis and Echinothrix diadema, and amino analogs of cristazarin, a metabolite of lichen Cladonia cristatella, were synthesized.
A New Tannin from Fruits of Torreya Nucifera with Protein Tyrosine Phosphatase 1B Inhibitory Activity
Authors: Guo Dao-Li
Published: March 2019

A new compound 1, 3, 6-tri -O-galloyl-2- O-(4 - carboxylgalloyl)-β-D-glucopyranose (1), together with six known compounds (2-7) were isolated from EtOAc-soluble extract of fruits of Torreya nucifera. Their structures were elucidated on the basis of detailed spectroscopic and physico-chemical analyses. All the isolates were evaluated for in vitro inhibitory activity against PTP1B, VHR and PP1. Among them, new compound 1 was found to exhibit selective inhibitory activity on PTP1B with IC50 value 8.9 ± 1.4 μM.
Comprehensive Metabolomics Study of Traditionally Important Rumex Species Found in Western Himalayan Region
Authors: Sharma Ritika , Jandrotia Rupali , Singh Bikram , Sharma Upendra , Kumar Dinesh
Published: March 2019

Rumex species are traditionally known to cure constipation, pain, inflammation, ulcer and tumor. The biological potential of Rumex nepalens is lies in chemical diversity of its constituents. In the present study, UPLC-DAD-MS method was developed for the concurrent estimation of polyphenols in Rumex species ( R. nepalensis, R. hastatus and R. dentatus) and validated for linearity (r2 > 0.999), limit of quantification and detection, inter and intraday precession, stabilities and recovery. The developed method has also been employed for metabolomic analysis of Rumex species. Qualitative and quantitative variation of polyphenols was observed among the aerial and root parts of Rumex species with highest content of polyphenol detected in aerial part of R. nepalensis. The quantitative data based matrix and HCA plot represents the variation of metabolites among the samples. R. nepalensis being widely used in traditional practices, was incorporated in detail. A total of seven molecules were isolated and characterized among which three compounds viz. 3- O- methyl epicatechin, quercetin-3- O- β-D-glucuronide and β-sitosterol-3- O- β-D-glucoside were isolated for first time from this plant. Eighteen metabolites were profiled in R. nepalensis using UPLC-MS/MS technique. Current comprehensive metabolomics approach will surely help in understanding the chemical diversity, discriminations and quality control analysis of raw materials and furnished products of Rumex.
Antidiabetic Effects of the Auricularia auricular Polysaccharides Simulated Hydrolysates in Experimental Type-2 Diabetic Rats
Authors: Lu Aoxue , Shen Meng , Fang Zhiyu , Xu Yaoyao , Yu Mengen , Wang Shuang , Zhang Yongjun , Wang Weimin
Published: March 2019

A model of type-2 diabetes mellitus (T2DM) using high-fat diet and low-dose STZ was established to assess the antidiabetic effects of Auricularia auricular polysaccharides simulated hydrolysates (AAPHs) obtained from the dried fruiting body of A. auricular. AAPHs were administered intragastrically (i.g.) at the dose of 0.15 g/kg b. W. to diabetic Wistar rats for 4 weeks. Results show that AAPHs was demonstrated to exhibit significant diminution in T-CHO and LDL-C levels (P < 0.05 or P < 0.01) compared to the diabetic control group. In addition, the secretion level of GLP-1 were different with the diabetes model group from 0 to 30 min, and had a tendency to alleviate weight loss. The current study suggests that AAPHs might be incorporated as a supplement in diabetic agents or combined with other health-care foods.
Composition and Chemical Variability of Essential Oils Isolated from Aerial Parts of Cassytha filiformis from Côte d'Ivoire
Authors: Ouattara Zana A. , Sangaré Nouho , Mamyrbekova-Bekro A. Janat , Békro Yves-Alain , Tomi Pierre , Paoli Mathieu , Bighelli Ange , Tomi Felix
Published: March 2019

The essential oils isolated from aerial parts of Cassytha filiformis L. harvested in five locations of Côte d'Ivoire were analyzed by GC(RI), GC-MS and 13C-NMR. The oils were dominated by sesquiterpene derivatives and the content of the main components varied substantially from sample to sample: (E)-β-caryophyllene (1.5-34.9%), bicyclogermacrene (1.0-25.8%), α-humulene (0.5-22.0%), spathulenol (1.0-18.5%) and germacrene D (6.6-16.6%). Two compositions could be distinguished: (i) bicyclogermacrene, germacrene D, spathulenol (2/5 samples) and (ii), (E)-β-caryophyllene, α-humulene (3/5 samples).
Chemical Composition, Antimicrobial and Anti-inflammatory Activity of Algerian Juniperus phoenicea Essential Oils
Authors: Abdelli Wafae , Bahri Fouad , Höferl Martina , Wanner Juergen , Schmidt Erich , Jirovetz Leopold
Published: March 2019

The essential oils (EOs) obtained by steam distillation from the leaves and the berries of Juniperus phoenicea L., harvested in northwest of Algeria were analyzed and their antimicrobial and anti-inflammatory activities were assessed. 63, 46 and 78 volatile compounds were identified by GC-FID and GC-MS from fresh leaves, dried leaves and berries representing 98.1%, 98.3% and 96.4% of the total oil, respectively. The fresh and dried leaves oils were mainly composed of β-phellandrene (43.9% / 44.9%), α-pinene (25.1% / 20.3%), myrcene (8.5% / 8.2%), α-phellandrene (4.7% / 4.5%) p -cymene (2.7%-3.0%) and limonene (2.3%-2.5%) whereas, the berries oil was mainly composed of α-pinene (43.7%), p -cymene (5.8%), β-phellandrene (4.6%), α-terpineol (4.3%) and α-campholenal (4.0%). The study of the antimicrobial activity showed that the 3 EOs were effective only on B. cereus ATCC 10876 and C. albicans ATCC 10231. No signs of acute toxicity have been noted in mice even at the highest dose tested (5000 mg/kg p.o). The fresh leaves, dried leaves and berries oils reduced the carrageenan-induced paw edema in mice by 16.8%, 15.2% and 6.4%, respectively, after 6 hours at a dose of 400 mg/kg p.o.
Phytotoxic Lignans from Artemisia arborescens
Authors: Labruzzo Andrea , Cantrell Charles L. , Carrubba Alessandra , Ali Abbas , Wedge David E. , Duke Stephen O.
Published: March 2019

A systematic bioassay-guided fractionation of methylene chloride extracts of the aerial part of Artemisia arborescens was performed in order to identify its phytotoxic compounds Two lignans were isolated, sesamin and ashantin, that inhibited growth of Agrostis stolonifera (bentgrass), a monocot, and Lactuca sativa (lettuce), a dicot, at 1 mg mL–1. In a dose-response screening of these lignans for growth inhibition against Lemna paucicostata (duckweed), ashantin was the most active with an IC50 of ca. 224 μM. The mode of action of these compounds is still unknown. In mosquito larvicidal bioassays the pure compounds sesamin and ashantin did not cause mortality at the highest dose of 125 mg/L against 1-d-old Aedes aegypti larvae. In bioautography bioassays for antifungal activity using Botrytis cinerea, Fusarium oxysporum, Colletotrichum fragariae, Colletotrichum acutatum, and Colletotrichum gloeosporioides, ashantin and sesamin were inactive at 5 μg and were therefore not subjected to additional screening in secondary antifungal assays.
Oxygenated Terpenes from the Indo-Pacific Nudibranchs Goniobranchus splendidus and Goniobranchus collingwoodi
Authors: Forster Louise C. , White Andrew M. , Cheney Karen L. , Garson Mary J.
Published: March 2019

Three new terpenes each with a highly oxygenated or rearranged spongian framework were characterized from organic extracts of the nudibranchs G. splendidus and G. collingwoodi collected from Eastern Australia.
Cochlearoids L and M: Two New Meroterpenoids from the Fungus Ganoderma cochlear
Authors: Qin Fu-Ying , Yan Yong-Ming , Tu Zheng-Chao , Cheng Yong-Xian
Published: March 2019

Cochlearoids L (1) and M (2), two new meroterpenoids and three known ones, were isolated from the fruiting bodies of Ganoderma cochlear. The new structures were elucidated by spectroscopic and chemical methods. Biological evaluation showed that 1 could inhibit bromodomain-containing protein 4 (BRD4) with IC50 value of 68.7 μM. Besides, 1 was found to have weak cytotoxic activities against three human cell lines (A549, K562, Huh-7) with IC50 values in the range of 39.6–190.0 μM.
Metabolic Profiling and Chemical-Based Antioxidant Assays of Green and Red Lettuce (Lactuca sativa)
Authors: Park Chang Ha , Yeo Hyeon Ji , Baskar Thanislas Bastin , Kim Jae Kwang , Park Sang Un
Published: March 2019

Lettuce ( Lactuca sativa) is an important leaf vegetable crop worldwide. The total phenolic content was higher in the red skirt methanol extracts with a level of 64.9 ± 0.3 mg GA/g, and phenolic content of green skirt was 49.4 ± 0.3 mg GA/g. The total flavonoid content in the methanol extract of red skirt showed the highest concentration (291.6 ± 9.0 mg rutin/g), followed by green skirt (223 ± 9.8 mg rutin/g). The red skirt showed a higher content of anthocyanin (23.7 ± 0.8 mg/100 g) compared to the green skirt (7.4 ± 0.9 mg/100 g). Seven carotenoids i.e., lutein, β–carotene, 9 Z–β–carotene, 13 Z–β–carotene, violaxanthin, zeaxanthin, and α–carotene were detected in both cultivars. The polar metabolites are strongly associated with the metabolites that participate in the TCA cycle. Correlations between primary and secondary metabolites were easily achieved by gas chromatography-time-of-flight mass spectrometry (GC-TOFMS)-based metabolite profiling method. Red skirt methanol extract showed 77.5 ± 0.4% 2,2-diphenyl-1-picrylhydrazyl (DPPH) activity, 50.8 ± 0.8% hydrogen peroxide radical scavenging assay and absorbance value (0.052) reducing power assay at 250 μL/mL, having significantly higher activity than the green skirt extract. The red lettuce extract also showed higher levels of phenolic compounds, flavonoids, and anthocyanins, and it possesses more antioxidant properties compared to the green skirt extract. In this study we compared two cultivars of lettuce, red skirt and green skirt, for various nutritional parameters and to understand the association of secondary metabolites with their corresponding primary metabolites. From the overall analysis, it is confirmed that GC-TOFMS-based metabolite profiling is an appropriate method for determining biochemical reactions and also acts as a combined resource to understand primary and secondary metabolism.
Effect of Guggulsterone on the Expression of Adiponectin in 3T3-L1 Cells
Authors: Saikumar Indira , Rasalkar Avinash A. , Shivakumar Bhadravathi M. , Reddy Divijendra N. , Malempati Rajyalakshmi
Published: March 2019

Obesity is a worldwide threat, affecting both developed and developing countries. Guggulipid obtained from gum guggul is widely prescribed in Ayurveda for various medical conditions including obesity. The present study was designed to investigate the effect of guggulsterone on the expression of adiponectin, the adipokine that regulates glucose and fatty acid metabolism. 3T3-L1 cells were treated with guggulsterone E / Z isomer [(GE) /(GZ)] and mRNA levels of adiponectin as well as PPARγ (a transcription factor that regulates adiponectin expression) were monitored. Treatment of 3T3-L1 cells with GE / GZ during differentiation into adipocytes led to reduced mRNA levels of adiponectin. However, no effect on the mRNA levels of adiponectin was observed when fully differentiated adipocytes were treated with either GE or GZ.
A New Quinolone Alkaloid with Cytotoxic Activity from the Fruits of Euodia Rutaecarpa
Authors: Ma Chen , Liu Xiao , Shan Yu , Xu Shu , Su Xiu-li , Feng Xu , Wang Qi-Zhi
Published: March 2019

A new quinolone alkaloid, 1-methyl-2-[( Z)-1-undecenyl]–4( 1H)-quinolone (1), together with two known quinolone alkaloids (2–3), and three known limonoids (4–6), were isolated from the fruits of Euodia rutaecarpa (Juss.) Benth.. Their chemical structure was determined by UV, MS, NMR and comparison with literatures. Bioassay results indicated that compound 1 had moderate cytotoxicity against tumor cell lines Lovo, MDA-MB-231 and HeLa with IC50 values of 6.72, 14.20 and 13.05 μM, respectively.
Yohimbine-related Alkaloids from Tabernaemontana corymbosa
Authors: Nugroho Alfarius Eko , Moue Miho , Sasaki Tadahiro , Shirota Osamu , Hadi A. Hamid. A. , Morita Hiroshi
Published: March 2019

Five new yohimbine-type indole alkaloids were isolated from the leaves of Tabernaemontana corymbosa. Their structures were determined on the basis of the NMR and Circular Dichroism (CD) spectroscopy.
Synthesis of Ficusnotins, Rare 1,4-Diarylbutanoids Derived from Ficusnota, via Ruthenium-Catalyzed Conjugate Addition
Authors: Yoon Jeong A , Ahn Sungwan , Han Young Taek
Published: March 2019

Ficusnotins are natural biarylbutanoids isolated from leaves of Ficus nota, a plant that is traditionally used as an alternative medicine in Southeast Asia. In this work, a concise synthesis of ficusnotin E was accomplished via ruthenium-catalyzed conjugate addition of 3,4-dimethoxyphenylboronic acid to a benzylvinyl ketone. Additionally, the other related natural 1,4-diarylbutanes derived from Ficus nota, namely, ficusnotin B, C, and F, were readily synthesized by subsequent chemical modifications of ficusnotin E. This procedure provides a concise and versatile route for the synthesis of ficusnotins and their biarylbutanoid analogs.
Anthocyanins from the Red Flowers of Meconopsis wallichi in Bhutan
Authors: Iwashina Tsukasa , Yangzom Rinchen , Murai Yoshinori , Dorji Kencho , Mizuno Takayuki , Wangmo Choki
Published: March 2019

Three anthocyanins were isolated from the red flowers of Meconopsis wallichi in Bhutan. They were characterized as cyanidin 3- O-glucoside, cyanidin 3- O-sambubioside and cyanidin 3- O-(succinylsambubioside) by UV-VIS, LC-MS, acid hydrolysis, alkaline saponification, and HPLC comparisons with authentic samples. The latter anthocyanin was reported in nature for the first time. However, flavonoids except for anthocyanins were not found in the flowers, showing that the red color is due to three cyanidin glycosides alone, without copigments and metals. Although the anthocyanins were reported from the blue flowers of three Meconopsis species, those of red flower Meconopsis species were characterized for the first time.
New Polyisoprenylated Polycyclic Phloroglucines from Clusia gundlachii
Authors: Zhang Jin , Zhao Jianping , Samoylenko Volodymyr , Jain Surendra , Tekwani Babu L. , Muhammad Ilias
Published: March 2019

A bioassay-guided fractionation yielded five new polycyclic phloroglucines derivatives, namely, gundlachiione A (1), gundlachiione B (2), gundlachiione C (3), gundlachiione D (4) and gundlachiione E (5) from the fruits of Clusia gundlachii, collected in Puerto Rico, USA. Their structures were determined by full spectroscopic data, including 2D NMR COSY, HMQC, HMBC, and NOESY experiments, and HRESIMS. Compounds 1 and 3 demonstrated activities against Leishmania donovani intracellular macrophage amastigotes in THP1 cultures, comparable to those observed for the standard drug pentamidine (IC50 and IC90 values 0.84 and 6.13 μg/mL, 2.32 and 3.01 μg/mL, 0.77 and 2.99 μg/mL, respectively). Both compounds, 1 and 3, also showed weak activities against L. donovani promastogotes and absence of cytotoxicity against transformed THP 1 cells.
Synthesis and Insecticidal Activity of β-Dihydroagarofuran Acetal Derivatives
Authors: Xi Xin , Zhao Ximei , Zhu Feng , Wei Jielu , Hu Zhan , Wu Wenjun , Zhang Jiwen
Published: March 2019

To search for improved insecticidal compounds based on β-dihydroagarofuran sesquiterpenoids, forty-four β-dihydroagarofuran acetal derivatives were designed and synthesized. Insecticidal activities and structure-activity relationship of these target compounds were evaluated. Some of the newly synthesized β-dihydroagarofuran acetal compounds were found to show higher insecticidal activity against sixth-instar larvae of Mythimna separate. Especially, compounds 2.2.9, 2.2.10, 2.2.11, 2.3.4, 2.3.6, 2.3.7, 2.5.4, 2.5.7 had great insecticidal activities with lower LD50 than that of the positive control celangulin-V (110.13 μg/g). It deserves mentioning that compound 2.2.11 showed the lowest LD50 (60.33 μg/g) among these compounds. Structure-activity relationship results suggested that the substituent groups of 1-, 6- and 9-positions of the target structures could greatly affect the insecticidal activity. Especially, when the substituent groups of 6-position were n-propyl, n-butyl, allyl, propargyl, o-fluorobenzyl, and p-fluorobenzyl, the compounds showed outstanding insecticidal activities.
New Acetylated Saponins from the Leaves of Trevesia palmata
Authors: Thao Le Thi Thanh , Quyen Do , Vu Duong Binh , Tai Bui Huu , Van Kiem Phan
Published: March 2019

Two new acetylated saponins, acetyltrevesiasaponins A (1) and B (2), were isolated from the leaves of Trevesia palmata. Their chemical structures were determined by analysis of HR-ESI-MS and NMR spectra. Compound 2 was also confirmed by alkaline hydrolysis and identification its prosapogenin 2a. Compounds 1, 2, and 2a were evaluated inhibitory effect on NO production in LPS stimulated BV2 cells. Compound 2 showed weak activity (IC50 40.7 μM).
Daffodils as Potential Crops of Biologically-active Compounds: Assessment of 40 Ornamental Taxa for their Alkaloid Profile and Cholinesterases Inhibition Activity
Authors: Breiterová Kateřina , Ločárek Miroslav , Kohelová Eliška , Talácková Markéta , Hulcová Daniela , Opletal Lubomír , Cahlíková Lucie
Published: March 2019

Many varieties of Narcissus (Amaryllidaceae) are planted on a large scale for ornamental purposes and at the same time they represent a rich reservoir of potential small chemical molecules that display several medicinal properties. Of the Amaryllidaceae alkaloids, considerable attention has been given to galanthamine, which possesses acetylcholinesterase inhibitory activity. Recent investigation has shown the pharmaceutical potential of other Amaryllidaceae alkaloids, such as lycorine, haemanthamine, and pancratistatine, primarily as anticancer drugs. In the current study, 40 Narcissus taxa were evaluated for their alkaloid profile by GC-MS. The aim of this work was to find the most suitable Narcissus varieties for a reliable source of galanthamine, lycorine, and haemanthamine for commercial production. Based on their mass spectra, 97 typical Amaryllidaceae alkaloids were detected of which 49 were identified. The highest concentrations of pharmaceutically-interesting Amaryllidaceae alkaloids were identified in the ornamental taxa N. cv Sundisc (galanthamine), N. cv. Jenny (lycorine), and N. cv. Sealing (haemanthamine). All alkaloidal extracts were also screened for their acetylcholinesterase and butyrylcholinesterase inhibitory activities.
Antifouling Potentials and Metabolite Profiles of Two Marine-derived Fungal Isolates
Authors: Zhang Xiao-Yong , Amin Muhammad , Xu Xin-Ya , Qi Shu-Hua
Published: March 2019

Extracts of the culture broths of Aspergillus sydowii SCSIO 00305 and Penicillium chrysogenum SCSIO 00258 exhibited a relatively broad spectrum of antifouling activity against various biofoulers. The main chemical components of their bioactive fractions were analyzed and identified by LC-MS and from literature data. Two bioactive fractions comprised of 1α-methoxyroquefortine C, meleagrin, roquefortine C and isoroquefortine C exhibited more significant anti-barnacle activity than meleagrin in field bioassays, suggesting that the combination of different bioactive compounds could display a stronger antifouling activity than a single compound in the complicated marine ecological environments.
New Flavanol Dimers from the Bark of Celtis tetrandra and Their TRAIL Resistance-Overcoming Activity
Authors: Seephonkai Prapairat , Ishikawa Ryusho , Arai Midori A. , Kowithayakorn Thaworn , Koyano Takashi , Ishibashi Masami
Published: March 2019

In the courses of our search for bioactive natural products on TRAIL resistance-overcoming activity, the active EtOAc extract from the bark of Celtis tetrandra was chemically investigated. The fractionation of the extract resulted in the isolation of flavanols; (+)-afzelechin (1), (-)- epiafzelechin (2), (-)-catechin (3), and two new flavanol dimers; (-)- epiafzelechin-(4α→8)-(-)-catechin (4) and (-)- epiafzelechin-(4α→8)-(-)- epicatechin (5). All isolated compounds 1-5 were tested for their TRAIL resistance-overcoming activity against AGS cells at the concentrations from 5–20 μM. It is likely that the flavanol dimers 4 and 5 exhibited weak activity in the range of the concentration of 10–20 μM as compared with the standard.
Anti-oxidative Fraction of Lycorma delicatula Alleviates Inflammatory Indicators
Authors: Baek Seung-Hwa , Joung Okjin , Lee Ho-Young , Shin Jae-Cheon , Choi Won-Sik , Lee Tae Hun , Hwang Jae-Sam , Nam Sung-Hee , Son Hyeong-U , Lee Sang-Han
Published: March 2019

Lycorma delicatula is a reluctant pest capable of living in the stems of several tree species. The population has recently expanded in Korea due to several environmental factors including climate change. However, the precise reasons for this rapid and drastic increase in population size remain unknown. In order to examine the potential utility of this surplus biomass of Lycorma delicatula, we prepared an aqueous fraction from a dried imago, and tested its various anti-inflammatory activities and effects on cytokine levels in lipopolysaccharide (LPS)-activated RAW264.7 cells. The aqueous extract of Lycorma delicatula showed potent inhibitory activity on nitric oxide production, by more than 60% at a concentration of 300 μg/mL. We also evaluated interleukin (IL)-13 level using enzyme-linked immunosorbent assays (ELISAs). The anti-oxidative fraction of Lycorma delicatula inhibited LPS-induced IL-13 production in a dose-dependent manner, and T-bet promoter activity of cells treated with 300 μg/mL of Lycorma delicatula extract was also dramatically inhibited to 62% of that of LPS-treated cells. Furthermore, we compared matrix metalloproteinase-7 (MMP-7), -9, -14 and -17 expressions using reverse transcription-polymerase chain reaction (RT-PCR), which showed a drastic decrease in RNA levels in cells treated with the anti-oxidative fraction. Together, the present results suggest that the aqueous fraction of Lycorma delicatula has potential to ameliorate inflammatory characteristics during an inflammation event, supporting the idea that the fraction may be applied as a biomaterial to prevent inflammatory damage in skin tissues.
A New 3-Prenyl-2-flavene and Other Extractives from Baphia massaiensis and Their Antimicrobial Activities
Authors: Keroletswe Ngonye , Majinda Runner R. T. , Masesane Ishmael B.
Published: March 2019

One new 3-prenyl-2-flavene, named baphiflavene A, 1, and eleven known compounds, 2-12, were isolated and reported for the first time from Baphia massaiensis using several chromatographic techniques. Their structures were elucidated using different spectroscopic techniques; 1D and 2D-NMR, HRMS, GC-MS, UV/Vis, FTIR and by comparison with literature data. The isolates were tested against Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, Escherichia coli and Candida albicans to establish their preliminary antimicrobial activities. The results revealed that compound 1 had moderate activities against both Gram positive ( B. subtilis and S. aureus) and Gram negative ( E. coli and P. aeruginosa) bacteria, and good activity against C. albicans with inhibition zones of 10–23 mm (compared to 19 mm for chloramphenicol and miconazole standards). To the best of our knowledge, this is the first phytochemical work reported on Baphia massaiensis.
Effect of Pretreatment of Morin on the Cisplatin-Induced Toxicity on LLC-PK1 and T24 Cells
Authors: Bello-Alvarez Claudia , Moreno-Londoño Ángela Patricia , Pedraza-Chaverri José
Published: March 2019

Cisplatin is a chemotherapeutic drug broadly used in the treatment of solid tumors. However, patients under this chemotherapy develop severe adverse effects, being nephrotoxicity the most frequent. Cisplatin-induced nephrotoxicity has been associated with oxidative stress, inflammation and apoptosis. Morin, a rather abundant flavonoid, presents antioxidant properties and, at the same time, decreases viability in some tumor cells. Taking into account these facts, it has been hypothesized that morin could attenuate cisplatin-induced kidney injury without interfering with antineoplastic activity of cisplatin. The aim of this study was to evaluate the potential cytoprotective effect of morin against cisplatin-induced damage in the Lilly Laboratories cell-porcine kidney 1 (LLC-PK1) cell line. In addition, the effect of pretreatment with morin on the toxicity of cisplatin on human urinary bladder transitional cell carcinoma T24 cell line was investigated. It was found that 200 μM morin attenuates cisplatin-induced damage on LLC-PK1 cells in a heme oxygenase-1 (HO-1) dependent-way. Moreover, it was found that 200 μM morin alone, decreases T24 cell viability in the same proportion as cisplatin. However, when T24 cells were pretreated with morin, the cell viability did not change compared to the cells treated only with cisplatin.
Cancer Chemopreventive Activity of Xanthones from Calophyllum elatum
Authors: Ito Chihiro , Matsui Takuya , Kobayashi Takashi , Tokuda Harukuni , Shanmugam Sivabalan , Itoigawa Masataka
Published: March 2019

In our continuing search for compounds with antitumor-promoting activity, we screened eight xanthones isolated from Calophyllum elatum Bedd. (Guttiferae) by examining their possible inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12- O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. Several compounds tested in this study showed inhibitory activity against EBV, without showing any cytotoxicity. Isogarciniaxanthone E (2) showed more potent activity than any of the other compounds tested. Furthermore, isogarciniaxanthone E (2) exhibited a marked inhibitory effect on mouse skin tumor promotion in an in vivo two-stage carcinogenesis test.
A New Secondary Metabolite from Korean Traditional Herb Plant Hovenia dulcis
Authors: Le Tu Cam , Kang Kyung-Yun , Yang Inho , Leutou Alain S. , Ko Jaeyoung , Son Young-Jin , Yee Sung-Tae , Nam Sang-Jip
Published: March 2019

Investigation of chemical compounds from the butanol soluble layer of the traditional herb Hovenia dulcis has led to the isolation of a new compound, identified as 2-methoxybenzoic acid-5- O-α-L-rhamnopyranoside (1), along with three known compounds, syringic acid-4- O-α-L-rhamnopyranoside (2), syringic acid (3), and vanillic acid (4). Their chemical structures were established from the interpretation of 2D NMR spectroscopic and the high-resolution mass data.
Ultrasound-assisted Extraction of Polysaccharide from Radix Bupleuri using Response Surface Methodology and Antioxidant Research of the Polysaccharide
Authors: Hao Changchun , Qu Hongjin , Chen Shi , Han Wenjing , Sun Runguang
Published: March 2019

This report used Response Surface Methodology (RSM) to analyze the conditions that extracting polysaccharide compound from Radix Bupleuri using ultrasonic wave. For determining the optimal extraction conditions, four independent variables, temperature (°C), ultrasonic intensity (UI, W/cm2), dilution rate (water-material ratio, mL/g) and time (min), were investigated using Box-Behnken design. In the results, the best condition after optimization was dilution rate of 35.0:1, UI of 24.5 W/cm2, temperature of 69.5°C and time of 14.6 min. Extraction efficiency was 7.67% and the purity reached 44.14%. It illustrates that the ultrasound-assisted extraction (UAE) was efficient and suitable for extracting polysaccharide from Radix Bupleuri. This paper also investigated the antioxidant activity of Radix Bupleuri polysaccharide (RBP) on superoxide anion radical, hydroxyl radical, and 2,2-diphenyl-1-picry-hydrazyl (DPPH), in vitro experiment. The result indicated that RBP could remarkably sweep away the hydroxyl radical, and had the capacity for clearing away superoxide radical and DPPH.
α-Glucosidase Inhibitor Isolated from Blechum pyramidatum
Authors: Cherigo Lilia , Martínez-Luis Sergio
Published: March 2019

Blechum pyramidatum (Lam.) Urb. is a species of extensive medicinal use in the American continent. In fact, antidiabetic and anticancer preparations from this plant have been patented in Mexico, even though their active constituents are not yet known. It was recently discovered that B. pyramidatum inhibits the action of the α-glucosidase enzyme, thereby corroborating the antidiabetic properties attributed to this plant. The primary purpose of this study was to identify and characterize the α-glucosidase inhibitors from this species. Bioassay-guided fractionation of a crude extract of B. pyramidatum led to the isolation of a main α-glucosidase inhibitor, Palmitic acid (IC50 237.5). This compound was identified by both spectroscopic and spectrometric analysis. Its inhibitory activity was similar to that of the antidiabetic drug acarbose (IC50 241.6 μM), which was used as a positive control in our bioassay. Kinetic analysis established that palmitic acid acted as a competitive inhibitor. Docking analysis predicted that this compound binds to the same site as acarbose does in the human intestinal α-glucosidase (PDB: 3TOP). The presence of palmitic acid in B. pyramidatum and its potent inhibitory activity against α-glucosidase enzyme provides solid evidence to support the antidiabetic use of this plant in traditional medicine.
Cordyceps militaris Extract Inhibits the NF-κB pathway and Induces Apoptosis through MKK7-JNK Signaling Activation in TK-10 Human Renal Cell Carcinoma
Authors: Park Soo Jung , Jang Hyun-Jin , Hwang In-Hu , Kim Jung Min , Jo Eunbi , Lee Min-Goo , Jang Ik-Soon , Joo Jong Cheon
Published: March 2019

The ubiquitous transcription factor, NF-κB, has been reported to inhibit apoptosis and induce drug resistance in cancer cells. Cordyceps militaris extract (CME) is involved in the regulation of the NF-κB signaling pathway. However, the detailed role of CME in the suppression of the NF-κB signaling pathway is unclear. We found that CME dose-dependently inhibited tumor necrosis factor-α (TNF-α)-induced NF-κB activation in TK-10 human renal cell carcinoma. CME prevented NF-κB from translocating to the nucleus, which resulted in the downregulation of GADD45B, upregulation of MKK7, and phosphorylation of JNK (p-JNK). The increased activation of Bax led to pronounced CME-induced apoptosis, which occurred through caspase-3. Furthermore, the siRNA-mediated knockdown of GADD45B inhibited MKK7 expression, whereas the siRNA-mediated inhibition of MKK7 downregulated p-JNK and the JNK inhibitor, SP600125, inhibited Bax expression. Thus, these results indicated that CME inhibited the activation of GADD45B via the inhibition of NF-κB activation, which upregulated the MKK7-JNK signaling pathway to induce apoptosis in TK-10 cells. Thus, this study reveals a novel anticancer function of CME.
Aceriphyllum rossii Exerts Lipid-Lowering Action in Both Normal and Hyperlipidemic Mice
Authors: Kim Mun Ock , Seo Jee Hee , Kwon Eun Bin , Kang Myung Ji , Lee Su Ui , Moon Dong Oh , Lee Mi Kyeong , Lee Chul-Ho , Lee Hyun Sun
Published: March 2019

This study aimed to evaluate the lipid-lowering effect of the MeOH extract of Aceriphyllum rossii and its CHCl3 fraction, as well as its inhibitory activity on DGAT in vitro, in normal and hyperlipidemic mice. We separated the MeOH extract of A. rossii into two portions, a CHCl3-soluble part and the remaining water residue, and performed DGAT enzymatic activity assay on them. Further assessment carried out to reveal that the MeOH extract and its CHCl3 fraction suppress the intestinal TG absorption after an acute lipid challenge, and ameliorate hyperlipidemia as well as obesity-related parameters (body weight gain, serum lipid profiles, and several adipose tissue weights) in HFD-induced obese mice. First, the MeOH extract and its CHCl3 fraction strongly inhibit DGAT1 and DGAT2 in vitro enzymatic activity. Second, the MeOH extract and the CHCl3 fraction inhibit intestinal TG absorption after an acute lipid challenge in mice. Finally, the CHCl3 fraction ameliorates various parameters of HFD-induced obesity mice, including body weight gain and serum levels of TG and glucose. Data obtained from the results obviously indicated that A. rossii prevents HFD-induced hyperlipidemia as well as obesity in mice possibly by inhibiting DGAT activity. We suggest that A. rossii MeOH extract and its CHCl3 fraction would be a useful material for the therapy of hyperlipidemia.
Microbial Transformation of Calamintha glandulosa Essential Oil by Aspergillus niger
Authors: Novakovic Miroslav , Bukvicki Danka , Vajs Vlatka , Tesevic Vele , Milosavljevic Slobodan , Marin Petar , Asakawa Yoshinori
Published: March 2019

A number of potentially useful compounds with various biological activities can be obtained from plant metabolites by microorganisms. In present research, essential oil of Calamintha glandulosa was subjected to the biotransformation process by mycromicete Aspergillus niger. GC/MS analyses of the original and biotransformed essential oil have revealed six (1–6) biotransformed compounds from one of the main component-limonene and one biotransformed product (7) originating from the less abundant component-thymol. Piperitone epoxide and piperitenone epoxide, the most abundant components of the original oil, were not biotransformed but gave three artefacts (A1, A2, B1) due to the acidic conditions formed in A. niger medium. Compounds 5, 6 as well as 7 have not been previously found as a biotransformation products of limonene (5 and 6) and thymol (7 rebpectively. New uct (5, 6, and 7) together with the artefacts, were isolated by silica gel column chromatography followed by preparative silica gel thin layer chromatography, and their structures were established by a combination of 1D and 2D NMR spectra and GC/MS data. Biotransformation has one more confirmed as useful method, complementary to synthesis, for obtaining different type of molecules.
Altered Antimicrobial and Anti-biofilm Forming Effect of Thyme Essential Oil due to Changes in Composition
Authors: Gömöri Csilla , Vidács Anita , Kerekes Erika Beáta , Nacsa-Farkas Elvira , Böszörményi Andrea , Vágvölgyi Csaba , Krisch Judit
Published: March 2019

The antimicrobial and anti-biofilm forming effect of thyme (Thymus vulgaris) essential oil (TEO) with different compositions was evaluated. Normally the main component in this TEO is thymol, but in 2014 we found that the proportions of γ-terpinene and p-cymene (the precursors in thymol biosynthesis) increased and that of thymol decreased. This altered composition led to changes in the antimicrobial and anti-biofilm forming capacity of the essential oil depending also on the type of microorganisms. In the case of bacteria, minimal inhibitory (MIC) and minimal bactericidal (MBC) concentrations either decreased or increased. In the case of yeasts, minimal fungicidal concentrations (MFC) increased 4- and 8-fold for TEO containing p-cymene as the main component. On the contrary, MIC values decreased for all the tested moulds. Anti-biofilm forming activity of TEO containing p-cymene as its main component decreased in almost all cases and P. fluorescens biofilm forming capacity was even enhanced.
Chemo- and Enantioselective Catalytic Hydrogenation of α,β-Unsaturated Ketones and Aldehydes as a Tool to Introduce Chiral Centers at α- or β-Positions of Ketones
Authors: Hagiwara Hisahiro
Published: March 2019

Catalytic enantioselective hydrogenations of acyclic and cyclic α,β-unsaturated ketones and aldehydes are useful protocols for introduction of chiral centers at α- and/or β-positions of ketones especially in process scale reactions, which are reviewed in addition to conjugate and organocatalytic transfer reductions from the literatures since 2000.
Strychnuxinal, A New Alkaloid from Strychnos nux-blanda Fruits
Authors: Sichaem Jirapast , Tip-Pyang Santi , Lugsanangarm Kiattisak , My Lien Do Thi
Published: March 2019

A new pyrrole alkaloid, strychnuxinal (1), along with ten known compounds (2–11) were isolated from the fruits of Strychnos nux-blanda. The structures of all the isolated compounds (1–11) were fully elucidated using spectroscopic data, as well as comparisons with the previous literature data. In addition, the absolute configuration of 1 at C-8 was determined by means of the ECD calculation. Moreover, all isolated compounds were evaluated for their acetylcholinesterase (AChE) inhibitory activity.
Chemical Constituents of the Different Parts of Colchicum micranthum and C. chalcedonicum and their Cytotoxic Activities
Authors: Gulsoy-Toplan Gizem , Goger Fatih , Yildiz-Pekoz Ayca , Gibbons Simon , Sariyar Gunay , Mat Afife
Published: March 2019

Colchicum species, which have been widely used as a medication for years, still remain important in treatment of Familial Mediterranean Fever, gout and Behcet's Disease. In the present work, alkaloids, phenolic compounds and cytotoxic activities from different parts of two Colchicum species, namely C. chalcedonicum and C. micranthum were investigated for the first time. From different parts of two species, alkaloids were isolated and colchicine concentrations were also determined by HPLC. The methanol extracts were investigated for their cytotoxic activity against the A549 cell line using the MTT and LDH methods. Additionally, the phenolic compounds of each extract were investigated by LC–MS/MS. Six alkaloids, namely colchicine, colchifoline, 2-demethylcolchicine, demecolcine, 4-hydroxycolchicine and N-deacetyl- N-formylcolchicine were isolated from different parts of two species. The autumn corm of C. micranthum possessed the highest amount of colchicine among all extracts. All extracts showed high cytotoxicity, while the highest toxicity was determined in the seed extract. According to the LC–MS/MS analysis, 19 phenolic compounds were shown to be present. This is the first study which highlights that the seeds of C. chalcedonicum and autumn corms of C. micranthum could be valuable for the pharmaceutical industry to obtain colchicine and other tropolone alkaloids.
Eliciting Effect of Catharanthine on the Biosynthesis of Vallesiachotamine and Isovallesiachotamine in Catharanthus roseus Cambial Meristematic Cells
Authors: Zhu Jianhua , He Shuijie , Zhou Pengfei , Zi Jiachen , Liang Jincai , Song Liyan , Yu Rongmin
Published: March 2019

Vallesiachotamine and isovallesiachotamine are pharmacologically active monoterpene indole alkaloids produced by Catharanthus roseus. However, the biosynthetic pathway for these two alkaloids has not been characterized. The results of our experiments demonstrated that catharanthine induced the biosynthesis of vallesiachotamine and isovallesiachotamine in C. roseus cambial meristematic cells (CMCs) in a time- and dosage-dependent manner. The highest yields of vallesiachotamine and isovallesiachotamine (i.e., 1.49 mg l−1 and 1.08 mg l−1, respectively) were observed in CMCs treated with 10 mg catharanthine l−1 for 12 h. The cells growth was inhibited by 20 mg catharanthine l−1 (i.e., 16.3% decrease in dry-cell weight). A quantitative reverse transcription polymerase chain reaction analysis revealed that catharanthine regulated the biosynthesis of vallesiachotamine and isovallesiachotamine by up-regulating the expression of specific genes, including STR (strictosidine synthase), SGD (strictosidine β-D-glucosidase) and ORCA3 (transcription factor octadecanoid-responsive Catharanthus AP2/ERF-domain 3). Finally, considering the up-regulated expression of STR and SGD was consistent with the accumulation of vallesiachotamine and isovallesiachotamine, a potential vallesiachotamine and isovallesiachotamine biosynthetic pathway was proposed.
Anti-inflammatory Effect of Pratol in LPS-stimulated RAW 264.7 Cells via NF-κB Signaling Pathways
Authors: Chung You Chul , Park Sung-Min , Kim Jin Hwa , Lee Geun Soo , Lee Jung No , Hyun Chang-Gu
Published: March 2019

The Trifolium pratense L. (red clover), which blossoms, leaves and stems can be used as medicines for treatment of burns, skin diseases, diabetes and other diseases. Recently study shown that pratol (7-hydroxy-4-methoxyflavone), an O-methylated flavone in T. pratense has been evaluated to induce melanogenesis in B16F10 melanoma cells. However, the anti-inflammatory effect of pratol has not been reported. In this study, we investigated the effects of pratol on anti-inflammation. We also studied the mechanism of action of pratol in LPS-stimulated RAW 264.7 cells. The cells were treated with various concentration of pratol (25, 50, or 100 μM) and 25 μM ammonium pyrrolidinedithiocarbamate (APDC) was used as control. The results in LPS-stimulated RAW 264.7 cells showed that pratol significantly reduced nitric oxide (NO) and prostaglandin E2 (PGE2) production without any cytotoxic. In addition, pratol strongly decreased the expression of inducible nitric oxide synthase (iNOS) and cyclooygenase (COX-2). Furthermore, pratol reduced proinflammatory cytokines such as tumour necrosis factor (TNF)-α, interleukin (IL)-1β and IL-6. We also found that pratol strongly inhibited activation of nuclear factor kappa B (NF-κB) by reducing the p65 phosphorylation and protecting inhibitory factor kappa B alpha (IκBα) degradation. The results suggest that, pratol may be used to treat or prevent inflammatory diseases such as dermatitis, arthritis, cardiovascular and cancer.
LC-MS Identification of Proanthocyanidins in Bark and Fruit of six Terminalia species
Authors: Singh Awantika , Kumar Sunil , Kumar Brijesh
Published: March 2019

Proanthocyanidins (PAs) are the most important and valuable polyphenolic compounds of Terminalia species (family Combretaceae) used for the treatment of several diseases. This study aims to seek identification and characterization of PAs in the ethanolic extracts of bark and fruit of six Terminalia species viz T. arjuna, T. bellerica, T. catappa, T. chebula, T. elliptica and T. paniculata. A high performance liquid chromatography with quadrupole time-of-flight tandem mass spectrometry (HPLC/ESI-QTOF-MS/MS) method was developed for the simultaneous identification and characterization of PAs. The chromatographic separation was carried on a Thermo Betasil C8 column (250 mmx4.5 mm, 5μm) operated with 0.1% formic acid aqueous solution and acetonitrile as the mobile phase. The MS/MS fragmentation study of [M-H]- ions obtained from these PAs showed distinguishable fragment ions with high mass accuracy. Heterocyclic ring fission (HRF), retro-Diels-Alder (RDA) fragmentation, quinone methide (QM) fragmentation and benzofuran formation (BFF) have been identified as the characteristic fragments. Total of 51 PAs were tentatively identified which include 28 dimers, 15 trimers and 8 other flavan-3-ols.
Osmanthus fragrans Flower Aqueous Extract and its Enriched Acteoside inhibit Melanogenesis and Ultraviolet-induced Pigmentation
Authors: Liu Shuo , Zhao Zhen , Huo Zhijun , Xu Zhiru , Zhong Yan , Wang Xiaoling , Yang Yiting , Wang Zhiyong
Published: March 2019

The Osmanthus fragrans flower (OFF) is commonly used as an additive for tea in China and as a traditional medicine to treat dysentery, asthma and hepatitis. In the current study, we have acquired the aqueous extract of the dried OFF (OFFE) and determined its enriched acteoside contents. However, whether OFFE and acteoside can modulate melanogenesis and pigmentation has yet to be determined. We here provide novel data revealing that OFFE and acteoside inhibit melanogenesis induced by α-MSH in B16 melanoma cells via the MITF-tyrosinase signaling pathway. Treatment with α-MSH (1μM) enhanced melanin levels and tyrosinase activity, up-regulated the mRNA levels of MITF and tyrosinase and increased the dendritic number in B16 melanoma cells, effects all being intervened by OFFE and acteoside. Of interest, OFFE and acteoside showed no direct inhibition of tyrosinase activity as revealed by our ex vivo tyrosinase activity assay. In addition, OFFE produced a depigmenting action on UVB-induced hyperpigmentation in guinea pigs, as shown by the improved skin brightness and the decreased melanin staining. Our data have demonstrated that OFFE can alter melanogenesis via modulating the MITF-tyrosinase signaling thereby leading to its depigmenting action in the in vivo model. OFFE could be a substitute for acteoside as a promising skin-whitening agent.
Synthesis of new A-conjugated Quinolone and Spiroindole Dammaranes by the Ozonolysis of 2,3-Indolodipterocarpol
Authors: Smirnova Irina E. , Khusnutdinova Elmira F. , Lobov Alexander N. , Kazakova Oxana B.
Published: March 2019

An one-step and efficient access to the new dammarane A-quinolones by ozonolysis of 2,3-indolodipterocarpol at 0°C through the 1,3-dipolar cycloaddition of ozone to the C2-C3 double bond of the triterpenoid core is reported. In the case of oxidation in AcOH, two spiroindoles were identified as a result of 1,2-cycloaddition of ozone to the C2-C3 double bond with following intramolecular rearrangements of 2,3-epoxy-intermediate. The structures of four new compounds were established by 1H, 13C NMR, COSY, NOSY, HMBC and HSQC analyses.
Element Content is a Highly Reliable Marker for Niche Vegetable Oils
Authors: Mohammed Faez , Guillaume Dom , Abdulwali Nada , Bchitou Rahma , Hajjaji Souad El , Bouhaouss Ahmed
Published: March 2019

The content of twelve elements encountered in four different vegetable oils, each coming from a specific geographical location was precisely determined by ICP-AES over three consecutive years (2015–2017). For each oil type, results were remarkably reproducible indicating that element composition is a powerful fingerprint to depict an oil. Our results allow us to suggest that, once the vegetable origin of any niche oil has been certified (using its element content or not), element content determination can sign its geographical origin.
Chemical Composition of the Essential Oils of Pogostemon auricularius, a Vietnamese Medicinal Plant
Authors: Satyal Prabodh , Chuong Nguyen Thi Hong , Pham Van The , Hung Nguyen Huy , Hien Vu Thi , Setzer William N.
Published: March 2019

The essential oils from the stems, the leaves, and the flowers of Pogostemon auricularius, growing wild in Vietnam, were obtained by hydrodistillation and analyzed by gas chromatography – mass spectrometry. The essential oils were dominated by sesquiterpenoids (62.3–71.0%) and diterpenoids (23.9–27.3%), with β-caryophyllene (20.7–31.5%), α-humulene (8.9–14.1%), and ( E,E)-geranyl linalool (14.0–19.6%) as major components. The abundant concentrations of β-caryophyllene and α-humulene, known analgesic and anti-inflammatory agents, likely account for the traditional use of P. auricularius in Vietnam to treat fevers, malaria, and sore throat.
Comparative Chemical Profiles of Essential Oil Constituents of Eight Wild Cinnamomum Species from the Western Ghats of India
Authors: Ananthakrishnan Ramamoorthy , SanthoshKumar Ettickal. S. , Rameshkumar Koranappallil B.
Published: March 2019

The volatile chemical profiles of 8 wild Cinnamomum species ( C. dubium Nees, C. litseifolium Thwaites, C. mohanense Gangapr. et al., C. palghatensis Gangop., C. riparium Gamble, C. travancoricum Gamble, C. walaiwarense Kosterm. and C. wightii Meissn.) and two chemotypes ( C. agasthyamalayanum Robi et al. and C. keralaense Kosterm.) from the Western Ghats, south India were reported for the first time. A total of 112 constituents belonging to monoterpenoid, sesquiterpenoid and phenyl propanoid classes were identified from the leaf essential oils by GC-FID and GC-MS analytical methods. Monoterpenoids and sesquiterpenoids were the major class of volatile compounds distributed in most of the Cinnamomum species studied. The study lead to the identification of natural sources of aroma compounds such as 1,8-cineole ( C. mohanense), 1,4-cineole ( C. wightii), safrole ( C. walaiwarense) and benzyl benzoate ( C. keralaense). Two new chemotypes of Cinnamomum species viz; C. agasthyamalayanum phellandrene-eugenol type and C. keralaense benzyl benzoate type were also discovered from the Western Ghats. The interrelationships between the studied species were discussed based on the volatile chemical profiles.