bluuebunny/crossref_metadata_2025 huggingface dataset:
A New Cytotoxic Tirucallane from the Twigs of Walsura trichostemon
Authors: Sichaem Jirapast , Siripong Pongpun , Tip-pyang Santi , Phaopongthai Jatuporn
Published: March 2019

A new tirucallane, trichostemonol (1), together with five known compounds (2–6) were isolated from the twigs of Walsura trichostemon. The structures of the isolated compounds were determined by extensive analysis of their spectroscopic data. All isolated compounds were evaluated for their cytotoxicity against KB and HeLa cells.
A New Ergostane Triterpenoid from Cultures of the Basidiomycete Inocybe lilacina
Authors: Liu Dong-Ze , Liu Qi , Yang Ping , Jiang Wen-Xia
Published: March 2019

A new ergostane triterpenoid (4α-methylergost-8,24(28)-dien-3,7,11-trione, 1) together with four known compounds (2–5) were isolated from cultures of the basidiomycete Inocybe lilacina. The structure of the new compound was established on the basis of IR, 1D and 2D NMR spectroscopic and MS experiments.
Phytotoxic Terpenes Produced by Phytopathogenic Fungi and Allelopathic Plants
Authors: Cimmino Alessio , Andolfi Anna , Evidente Antonio
Published: March 2019

This review is about the isolation as well as chemical and biological characterization of simple and complex mono-, sesqui-, di-, sester- and tri-terpenes produced by fungal pathogens of agrarian and forest plants and by some allelopathic plants. In several cases, the structure activity relationships are also discussed, as well as their potential application in agriculture as natural safe herbicides, fungicides and bactericides. Furthermore, the potential application of some fungal terpenes as anticancer compounds with a new mode of action is also discussed.
A New Pyrrolosesquiterpene from the Terrestrial Streptomyces sp. Hd7-21
Authors: Dong-Ze Liu , Liang Bo-Wen
Published: March 2019

One new pyrrolosesquiterpene 1 was isolated from cultures of the soil actinomycete Streptomyces sp. Hd7-21. Its structure was elucidated by extensive MS and 1D and 2D NMR spectroscopic data analyses.
Chemical Modifications of Cinchona Alkaloids Lead to Enhanced Inhibition of Human Butyrylcholinesterase
Authors: Karlsson Daniela , Fallarero Adyary , Shinde Pravin , Anju CP , Busygin Igor , Leino Reko , Mohan C. Gopi , Vuorela Pia
Published: March 2019

Butyrylcholinesterase (BChE) inhibitors were identified from a collection containing cinchonine, cinchonidine and synthetic derivatives, and further characterized using cytotoxicity and molecular docking studies. The most active ones were: (10≡)-10,11-dibromo-10,11-dihydrocinchonidine (11), a competitive inhibitor with Ki, = 3.45±0.39 μM, and IC50 BChE = 9.83±0.30 μM/human (h)BChE = 34.47±4.63 and O-(trimethylsilyl)cinchonine (15), a mixed inhibitor with Kiuc = 1.73±0.46 μM and Kic = 0.85±0.26 μM, and IC50 BChE = 0.56±0.14 μM / hBChE = 0.24±0.04. In cytotoxicity experiments, ≥80% of the cells remained viable when exposed to concentrations of up to 80 μM of both inhibitors in four different cell lines, including neurons. Due to the bulkier trimethylsilyl side group of 15, it covered the active site of hBChE better than 11 with an OH-group while not being able to fit into the active site gorge of hAChE, thus explaining the selectivity of 15 towards hBChE.
Crinane Alkaloids of the Amaryllidaceae with Cytotoxic Effects in Human Cervical Adenocarcinoma (HeLa) Cells
Authors: Nair Jerald J. , Rárová Lucie , Strnad Miroslav , Bastida Jaume , Cheesman Lee , van Staden Johannes
Published: March 2019

The family Amaryllidaceae has a long history of usage in the traditional medicinal practices of the indigenous peoples of South Africa, with three of its species known to be used for cancer treatment. Furthermore, the Amaryllidaceae is widely recognized for its unique alkaloid constituents, several of which exhibit potent and selective cytotoxic activities. In this study, several crinane alkaloids derived from local Amaryllidaceae species were examined for cytotoxic effects against the human cervical adenocarcinoma cell line, of which distichamine was the most potent (IC50 2.2 μM).
Alkaloids from Xylariaceae sp., a Marine-derived Fungus
Authors: Nong Xu-Hua , Zhang Xiao-Yong , Xu Xin-Ya , Sun Yun-Lin , Qi Shu-Hua
Published: March 2019

A new pyridine derivative, 5-(2′-hydroxypropyl)pyridin-3-ol (1), with seven known alkaloids, 3-hydroxy-5-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one (2), penicillenol A1 (3), penicillenol A2 (4), a mixture of quinolactacin A1 (5a) and quinolactacin A2 (5b), and a mixture of quinolactacin C1 (6a) and quinolactacin C2 (6b), were isolated from the culture broth of a marine-derived fungus Xylariaceae sp. SCSGAF0086. Their structures were elucidated by spectroscopic methods. Compound 2 showed weak antimicrobial activity against Bacillus subtilis, and a mixture of 6a and 6b exhibited strong antifouling activity toward Bugula neritina larval settlement.
Occurrence of a Taurine Derivative in an Antarctic Glass Sponge
Authors: Carbone Marianna , Núñez-Pons Laura , Ciavatta M. Letizia , Castelluccio Francesco , Avila Conxita , Gavagnin Margherita
Published: March 2019

The n-butanol extract of an Antarctic hexactinellid sponge, Anoxycalyx (Scolymastra) joubini, was found to contain a taurine-conjugated anthranilic acid, never reported so far either as a natural product or by synthesis. The compound was inactive against human cancer cells in an in vitro growth inhibitory test, and also showed no antibacterial activity.
MAO-A Inhibition Profiles of Some Benzophenone Glucosides from Gentiana verna subsp. pontica
Authors: Kaya Duygu , Jäger Anna K , Yalçın Funda N. , Ersöz Tayfun
Published: March 2019

Gentiana verna L. subsp. pontica (Soltok.) Hayek, G. pyrenaica L., and G. verna L. subsp. balcanica Pritchard from Turkey were tested for their MAO-A inhibitory effects. A photometric peroxidase linked MAO-A bioassay performed on the H2O extracts prepared from the methanolic extracts of the title plants revealed the potential effect of G. verna subsp. pontica and three benzophenone glucosides; 2,3′-dihydroxy-4-methoxy-benzophenone-6-O-β-glucopyranoside (1), 2,4,3′,4′-tetrahydroxy-benzophenone-6-O-β-glucopyranoside (maclurin-6-O-β-glucopyranoside) (2) and 2,4,3′-trihydroxy-benzophenone-6-O-β-glucopyranoside (3) isolated from G. verna subsp. pontica. Among the benzophenone glucosides 1 and 2 exhibited significant inhibition of MAO-A (IC50=31.3±4 μM and 41±4.7 μM resp.).
Phytochemical Investigations of Lonchocarpus Bark Extracts from Monteverde, Costa Rica
Authors: Deskins Caitlin E. , Vogler Bernhard , Dosoky Noura S. , Chhetri Bhuwan K. , Haber William A. , Setzer William N.
Published: March 2019

The acetone bark extracts of three species of Lonchocarpus from Monteverde, Costa Rica, L. atropurpureus, L. oliganthus, and L. monteviridis, were screened for antibacterial, cytotoxic, and antioxidant activities. L. orotinus extract was antibacterial against Bacillus cereus (MIC = 39 μg/mL), while L. monteviridis exhibited the most antioxidant activity. None of the Lonchocarpus extracts showed cytotoxic activity against MCF-7 cells. Fatty acids and atraric acid were isolated and purified from L. atropurpureus bark, fatty acids and loliolide from L. oliganthus bark, and leonuriside A and β-D-glucopyranos-1-yl N-methylpyrrole-2-carboxylate from L. monteviridis bark. Atraric acid showed cytotoxic and antimicrobial activities.
Immune Enhancing Effects of Echinacea purpurea Root Extract by Reducing Regulatory T Cell Number and Function
Authors: Kim Hyung-Ran , Oh Sei-Kwan , Lim Woosung , Lee Hyeon Kook , Moon Byung-In , Seoh Ju-Young
Published: March 2019

Echinacea purpurea preparations (EPs) have been traditionally used for the treatment of various infections and also for wound healing. Accumulating evidence suggests their immunostimulatory effects. Regulatory T cells (Tregs) are known to play a key role in immune regulation in vivo. However, there have been no reports so far on the effects of EP on the frequency or function of Tregs in vivo. Therefore, in the present study, we investigated the quantitative and functional changes in Tregs by in vivo administration with EP. The frequencies of CD4+FoxP3+ and CD4+CD25+ Tregs in the spleens of BALB/c mice administered with EP for 3 weeks were investigated by flow cytometry. The suppressive function of CD4+CD25+ Tregs in association with the proliferative activity of CD4+CD25- effector T cells (Teffs) and the feeder function of CD4- antigen-presenting cells (APCs) were analyzed by carboxyfluorescein succinimidyl ester-dilution assay. The results showed a lowered frequency of CD4+FoxP3+ and CD4+CD25+ Tregs and attenuated suppressive function of CD4+CD25+ Tregs, while the feeder function of APCs was enhanced in the EP-administered mice. On the other hand, the proliferative activity of Teffs was not significantly different in the EP-administered mice. The results suggest that decreased number and function of Tregs, in association with the enhanced feeder function of APCs, may contribute to the enhancement of immune function by EP.
Isocorilagin, a Cholinesterase Inhibitor from Phyllanthus niruri
Authors: Koay Yee-Hui , Basiri Alireza , Murugaiyah Vikneswaran , Chan Kit-Lam
Published: March 2019

Drugs that have dual inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) produce better clinical efficacy against Alzheimer's disease (AD) than those that selectively inhibit one enzyme. A dual cholinesterase inhibitory-guided fractionation of Phyllanthus niruri leaves afforded isocorilagin, a bioactive tannin possessing good inhibitory activities against AChE (IC50: 0.49 μM) and BChE (IC50: 4.20 μM). Interestingly, isocorilagin was relatively 2- to 3-fold more potent than galanthamine, the clinically used inhibitor. The kinetic analyses suggested that isocorilagin was a non-competitive inhibitor for AChE and an uncompetitive inhibitor for BChE, with calculated Ki values of 1.49 μM and 2.86 μM, respectively. In silico molecular docking revealed that isocorilagin effectively blocked the substrate entry by forming hydrogen bonding with residues at the entrance of the AChE active site. With BChE, the compound completely docked inside and occupied the active site of the enzyme. This study demonstrated for the first time the potent cholinesterase inhibitory activities of isocorilagin, a promising lead that is worthy of further investigation.
Antioxidant Activity and Total Phenolic Contents of Three Bupleurum Taxa
Authors: Kim Hyeusoo , Kim Sea Hyun , Yun Kyeong Won
Published: March 2019

Bupleuri Radix (Bupleurum spp. root) is one of the most important crude drugs in Korea, China and Japan. We investigated the total phenolic content and antioxidant activity of three Bupleurum taxa (B. falcatum, B. falcatum ‘Mishima’ and B. latissimum). The highest total phenolic content was found in B. latissimum (18.6±1.7 mg/g) and the least in B. falcatum ‘Mishima’ (9.4±0.5 mg/g). The ethyl acetate fractions obtained from B. falcatum and B. falcatum ‘Mishima’ showed higher DPPH radical scavenging activity than the other fractions. In the case of B. latissimum, the DPPH radical scavenging activity of the diethyl ether fraction was higher than that of the other fractions. These results suggest that the three Bupleurum plants may be used as a food additive as a natural antioxidant.
Quantification of γ-Aminobutyric Acid in Sri Lankan Tea by Means of Ultra Performance Tandem Mass Spectrometry
Authors: Carvalho Elisabete , Punyasiri P.A. Nimal , Somasiri H.P.P Sudarshana , Abeysinghe I. Sarath B. , Martens Stefan
Published: March 2019

γ-Aminobutyric acid (GABA), an important bioactive component of tea, acts as a major inhibitory neurotransmitter and is considered to influence other physiological processes in human as well as in planta. In the hereby presented study, the content of this valuable metabolite was investigated in two novel types of Ceylon Tea, explicitly “Silver Tips” and “White Tea”, originating from minimally processed buds of the unique cultivar, “TRI 2043″. The samples were subjected to hot water infusion, equivalent to the traditional beverage preparation procedure, and analyzed by means of hydrophilic interaction ultra performance liquid chromatography coupled to tandem mass spectrometry (HILIC LC-MS/MS). The registered GABA levels were compared with those obtained for the classic “Black Tea” and “Green Tea” samples from Sri Lanka. A high variation of GABA content was observed among the different tea types, especially in the case of “Silver Tips” and “White Tea”, indicating the crucial influence of the manufacturing procedure (processing extent) on the final abundance of the bioactive component of interest. Furthermore, “White Tea” samples boasted the highest GABA concentration reported for this type of tea so far, reaching up to 50% of that characteristic of the high-priced “GABA Tea”. Therefore, “White Tea” and “Silver Tips” were proved to be high quality teas with amounts of γ-aminobutyric acid comparable with those described for similar types before. To our knowledge, this is the first report on HILIC LC-MS/MS application for the quantification of GABA and for in-depth characterization of teas from Sri Lanka.
5-(Hydroxymethyl)-2-furaldehyde Inhibits Adipogenic and Enhances Osteogenic Differentiation of Rat Bone Mesenchymal Stem Cells
Authors: Tan Xiang-ling , Zhang Yan-Hong , Cai Jian-Ping , Zhu Li-Hua , Ge Wen-Jie , Zhang Xian
Published: March 2019

Eucommiae Cortex (Eucommia ulmoides Oliver Bark) has been used for anti-osteoporosis usually as an ethnic drug for hundred years in China. In this study, a bioactive compound, 5-(hydroxymethyl)-2-furaldehyde (5-HMF), was isolated from Eucommiae Cortex. We found that after rat bone mesenchymal stem cells (bMSCs) were induced by 5-HMF at the concentration of 0.05, 0.10 and 0.20 μg/mL in the normal medium for 7 and 14 days, the mRNA expression of ALP, COLlαl (7 days only), OCN and OPN increased. However, in the adipogenic induction medium (AIM), the mRNA expression of PPARγ, FABP4, C/EBPα and LPL decreased with the 5-HMF treatment. Mineralized nodule formations were enhanced after bMSCs were induced by 5-HMF for 14 and 21 days in normal medium. In the AIM medium, 5-HMF not only inhibited the formation of adipose cells obviously, but also stimulated the mineralized nodule formation after induced for 21 days. These results indicated that 5-HMF was a powerful inhibitor of adipogenesis and enhancer of osteoblastogenesis. It may be one of the constituents contributing to anti-osteoporosis in Eucommiae Cortex.
Variation of Glucosinolate Accumulation and Gene Expression of Transcription Factors at Different Stages of Chinese Cabbage Seedlings under Light and Dark Conditions
Authors: Kim Yeon Bok , Chun Jin-Hyuk , Kim Hye Ran , Kim Sun-Ju , Lim Yong Pyo , Park Sang Un
Published: March 2019

Chinese cabbage is one of the most important leafy vegetables widely used in East Asian cuisines. The glucosinolate (GSL) accumulation and transcript levels of 7 transcription factors (Dofl.l, IQD1-1, MYB28, MYB29, MYB34, MYB51, and MYB122, and their isoforms) involved in the biosynthesis of aliphatic and indolic glucosinolates (GSLs) were analyzed at different stages of Chinese cabbage (Brassica rapa ssp. pekinensis) seedlings under light and dark conditions using high performance liquid chromatography and quantitative real time PCR. During seedling development, transcription of almost all transcription factors under light conditions was higher expressed than under dark conditions. Five aliphatic GSLs (progoitrin, sinigrin, glucoalyssin, gluconapin, and glucobrassicanapin) and four indolic GSLs (4-hydroxyglucobrassicin, glucobrassicin, 4-methoxyglucobrassicin, and neoglucobrasscin) were detected. Total GSL contents under light conditions 6, 8, and 10 days after sowing (DAS) were 3.2-, 3.9-, and 6.9-fold higher, respectively than those of dark conditions. Interestingly, total GSL contents 2 {85.4 μmol/g dry weight (DW)} to 10 (7.74 μmol/g DW) DAS under dark conditions were gradually decreased. In this study, our results suggest that light affects the levels of GSL in Chinese cabbage seedlings. These results could be useful for obtaining cabbage varieties rich in GSLs.
Identification of the Hydroxamate Siderophore Ferricrocin in Cladosporium cladosporioides
Authors: Pourhassan Nina , Gagnon René , Wichard Thomas , Bellenger Jean-Philippe
Published: March 2019

The hydroxamate siderophore ferricrocin was identified in Cladosporium cladosporioides growth medium by solid phase extraction and ultra high pressure liquid chromatography coupled to a time of flight mass spectrometer (UHPLC/QTOF-MS). Both desferricrocin and ferricrocin were detected in the extracellular medium assisted by high resolution mass spectrometry. This is the first identification of a hydroxamate siderophore in Cladosporium cladosporioides. This finding emphasizes the common meaning of ferricrocin in fungi.
Korean Propolis Suppresses Angiogenesis through Inhibition of Tube Formation and Endothelial Cell Proliferation
Authors: Park Seon-Il , Ohta Toshiro , Kumazawa Shigenori , Jun Mira , Ahn Mok-Ryeon
Published: March 2019

Propolis, a sticky material that honeybees collect from living plants, has been used for its pharmaceutical properties since ancient times. In this study, we examined the effects of ethanol extracts of Korean propolis (EEKP) from various geographic regions on the inhibition of angiogenesis, both in vitro and in vivo. The effects of EEKP were tested on in vitro models of angiogenesis, that is, tube formation and proliferation of human umbilical vein endothelial cells (HUVECs). All EEKP samples exhibited significant inhibitory effects on tube formation of HUVECs in a concentration-dependent manner (6.25-25 μg/mL). In addition, two EEKP samples, prepared from Uijeongbu and Pyoseon propolis, significantly suppressed the proliferation of HUVECs in a concentration-dependent manner (3.13-25 μg/mL). Furthermore, in an in vivo angiogenesis assay using the chick embryo chorioallantoic membrane (CAM) system, we found that the two EEKP samples significantly reduced the number of newly formed vessels. These results indicate that Korean propolis may have potential applications in the prevention and treatment of angiogenesis-related diseases such as cancer.
Cytotoxicity and Antimicrobial Activity of the Essential Oil from Satureja montana subsp. pisidica (Lamiceae)
Authors: Kundaković Tatjana , Stanojković Tatjana , Kolundžija Branka , Marković Stevan , Šukilović Branka , Milenković Marina , Lakušić Branislava
Published: March 2019

The antimicrobial and cytotoxic activities of the essential oil of Satureja montana ssp. pisidica from two localities (mountains Korab and Galičica) were studied. Forty-nine components were identified in the each sample. Oxygenated monoterpene hydrocarbons were the major compounds: carvacrol, thymol, carvacrol methyl ether and β-linalool. Both tested essential oils showed very high and similar antimicrobial activity. Minimal inhibitory concentrations ranged from 12.5 μg/mL against S. epidermidis to 50 μg/mL against P. aeruginosa and C. albicans. The cytotoxic effect of the essential oils was tested against MDA-MB-361, MDA-MB-453, HeLa, LS174 and MRC5 cells. The essential oil from Korab demonstrated significantly better results than the oil from Galičica, particularly against HeLa and MDA-MB-453 cell lines, with IC50 values of 63.5 and 72.3 μg/mL, while the oil from Galičica was the most active on the human epithelial cervical cancer HeLa cells (IC50 99.7 μg/mL).
Chemical Composition of Essential Oils of Grindelia squarrosa and G. hirsutula
Authors: Veres Katalin , Roza Orsolya , Laczkó-Zöld Eszter , Hohmann Judit
Published: March 2019

The essential oils of Grindelia squarrosa (Pursh) Dunal and G. hirsutula Hook. & Arn. cultivated in Romania were isolated by hydrodistillation. The essential oils were analyzed by a combination of GC-FID and GC-MS. The identification of the constituents was achieved from their retention indices and comparison of their MS data with computer library database and literature data. The fifty-six identified constituents accounted for 72.1-81.3% of the oils. The oils were found to contain α-pinene, β-pinene, limonene, borneol, bornyl acetate and germacrene D as main constituents. The oils obtained from the two species showed small differences in chemical composition. However, menthol, menthone and pulegone were detected only in the essential oil of G. hirsutula.
Volatile Compounds from Roots, Stems and Leaves of Angelica acutiloba growing in Taiwan
Authors: Chen Hsin-Chun , Tsai Yi-Jr , Lin Li-Yun , Wu Chin-Sheng , Tai Shan-Pao , Chen Yu-Chang , Chiang Hsiu-Mei
Published: March 2019

The present study analyzed and compared the volatile compounds in fresh Angelica acutiloba roots, stems and leaves both qualitatively and quantitatively. The volatile compounds were isolated by either steam distillation (SD) or headspace-solid phase microextraction (HS-SPME). A total of 61 compounds were identified using gas chromatography/mass spectrometry (GC/MS). All 61 compounds were verified by SD, with 3n-butyl phthalide, γ-terpinene, p-cymene and cis-β-ocimene as the main compounds. Thirty-three compounds were verified by HS-SPME, with γ-terpinene and p-cymene as the main compounds. The leaf samples contained the highest essential oil content. Compared with SD, HS-SPME sampling resulted in relatively higher amounts of highly volatile monoterpenes and lower amounts of less volatile compounds such as 3n-butyl phthalide. These findings demonstrate that A acutiloba roots, stems and leaves have high 3 n-butyl phthalide contents; thus, all parts of A. acutiloba may be used for further application and development.
Induced Production of New Diterpenoids in the Fungus Penicillium funiculosum
Authors: Liu Dong-Ze , Liang Bo-Wen , Li Xiao-Fei , Liu Qiang
Published: March 2019

The supplementation of a DNA methyltransferase inhibitor, 5-azacytidine (5-AZ), to the culture medium of Penicillium funiculosum, dramatically altered its metabolic profiles. Analysis of the culture broth extract led to the isolation of two new prenyleudesmane diterpenoids (1-2). The isolated compounds were further evaluated for their cytotoxic and antibacterial activities. Our findings confirmed that the use of chemical epigenetic modifiers is an effective technique for promoting the expression of silent biosynthetic pathways to produce unique secondary metabolites.
Triterpene Saponins from the Sea Cucumber Stichopus chloronotus
Authors: Thao Nguyen Phuong , Luyen Bui Thi Thuy , Vien Le Thi , Tai Bui Huu , Dat Le Due , Cuong Nguyen Xuan , Nam Nguyen Hoai , Van Kiem Phan , Van Minh Chau , Kim Young Ho
Published: March 2019

Sea cucumbers have been used as a dietary delicacy and important ingredient in Asian traditional medicine and functional foods over many centuries. Using combined chromatographic methods, six triterpene saponins (1-6), including a new compound, stichloroside F (1), were isolated from a methanol extract of the sea cucumber Stichopus chloronotus Brandt. Their structures were determined on the basis of spectroscopic (1H and 13C NMR, HSQC, HMBC, 1H-1H COSY, ROESY) and FTICR-MS data and by comparison with literature values.
Ferulaldehyde and Lupeol as Direct and Indirect Antimicrobial Compounds from Cordia gilletii (Boraginaceae) Root Barks
Authors: Okusa Philippe N. , Stévigny Caroline , Névraumont Marie , Gelbcke Michel , Van Anrwerpen Pierre , Braekman Jean Claude , Duez Pierre
Published: March 2019

Cordia gilletii De Wild (Boraginaceae), a medicinal plant used against infectious diseases in the Democratic Republic of Congo, was investigated for direct and indirect antimicrobial properties. On one hand, the methanol extract is active against many pathogenic bacteria, including resistant strains. Its bio-guided fractionation led to the isolation of ferulaldehyde; this compound showed antimicrobial and antioxidant properties that may support the activity we observed for the methanol extract and some of the traditional uses of C. gilletii. On the other hand, the n-hexane extract of root barks possesses indirect antimicrobial properties, enhancing the activity of antibiotics against methicillin-resistant Staphylococcus aureus (MRSA). The fractionation of this extract led to the isolation of lupeol, which decreases the minimum inhibitory concentration of several antibiotics (4 to 8 fold) against MRSA and contributes to the effects observed for the raw n-hexane extract.
New C20-Diterpenoid Alkaloids from Delphinium laxicymosum var pilostachyum
Authors: Chen Dong-Lin , Tang Ping , Chen Qiao-Hong , Wang Feng-Peng
Published: March 2019

From the whole herb of Delphinium laxicymosum var pilostachyum, three new C20-diterpenoid alkaloids, laxipilostine, laxipilosdine, and laxipilosline (1-3), were isolated, together with fourteen known diterpenoid alkaloids. Their structures were determined by extensively interpretation of their spectroscopic data (1D- and 2D-NMR, MS, and IR).
Diastereoselective Synthesis of (+)-Pseudohygroline via Proline-catalyzed α-Hydroxylation
Authors: Anusha Bheemreddy , Reddy Ummareddy V. Subba , Reddy Basireddy V. Subba , Reddy Cirandur Suresh
Published: March 2019

A highly diastereoselective total synthesis of (+)-pseudohygroline (1) starting from D-proline is described using Wittig olefination and MacMillan-α-hydroxylation as key reactions. (+)-Pseudohygroline is an important molecule in alkaloid chemistry as it was prepared as part of the first chemical proof of the absolute stereochemistry of biosynthetically important (+)-hygroline (2) and (+)-hygrine (3).
Identification of Nucleosides and Nucleobases from Cultured Cordyceps militaris
Authors: Chen Li-hua , Yang Min-juan , Guan Yong-mei , Zhu Wei-feng , Huang Hui-Lian
Published: March 2019

Four nucleosides and seven nucleobases were isolated from the BuOH subfraction of the extract of cultured Cordyceps militaris; one of them, 6-acetylpurine (1) is a new natural compound. The structure of 1 was determined on the basis of HR-ESI-MS, and 1D and 2D NMR spectroscopic analysis.
Orthosiphol A from the Aerial Parts of Orthosiphon aristatus is Putatively Responsible for Hypoglycemic Effect via α-Glucosidase Inhibition
Authors: Damsud Thanakorn , Grace Mary H. , Adisakwattana Sirichai , Phuwapraisirisan Preecha
Published: March 2019

An infusion of Orthosiphon aristatus has long been used for diabetes therapy; however, the active principles remained unknown. Herein, we report the identification of the putative agents responsible for this antidiabetic activity using an α-glucosidase-guided isolation. Four flavonoids named sinensetin (1), salvigenin (2), tetramethylscutellarein (3) and 3,7,4′-tri- O-methylkaempferol (4), together with a diterpenoid named orthosiphol A (5), were characterized, based on analysis of their spectroscopic data. Flavonoids 3 and 4 inhibited yeast α-glucosidase with IC50 values of 6.34 and 0.75 mM, respectively, whereas orthosiphol A (5) selectively inhibited intestinal maltase with an IC50 value of 6.54 mM. A kinetic investigation of 5 indicated that it retarded maltase function in a noncompetitive manner.
New Dihydrochalcone and Propenamide from Lithocarpus polystachyus
Authors: Li Xiong , Zhao Ya , Huang Song , Song Weifeng , Zeng Xing , Hou Shao Zhen , Lai Xiao Ping
Published: March 2019

Two new compounds, (E)-4-(3, 4-dihydroxyphenyl)-N-(1-hydroxy-2-(4-hydroxyphenyl) ethyl)-2-oxobut-3-enamide (1) and phloretin2-O-β-D-apiofuranosyl (1→6)-β-D-glucopyranoside (2) were isolated from Lithocarpus polystachyus Rehd. Their structures were determined on the basis of analysis of their 1D and 2D NMR spectroscopic and mass spectral data.
Cytotoxic Constituents from the Vietnamese Fungus Xylaria schweinitzii
Authors: Linh Doan Thi Phuong , Hien Bui Thi Thu , Que Do Due , Lam Duong Minh , Arnold Norbert , Schmidt Jürgen , Porzel Andrea , Quang Dang Ngoc
Published: March 2019

Two new fungal pigments named schweinitzins A and B (1-2), together with (S)-torosachrysone-8-O-methyl ether (3) and emodin-6,8-di-O-methyl ether (4) have been isolated from the methanolic extract of the fruit bodies of Xylaria schweinitzii (Xylariaceae) collected in Cuc Phuong national park, Ninh Binh province, Vietnam, by silica gel column chromatography and preparative HPLC. Their structures were elucidated by spectroscopic analysis such as IR, UV-Vis, 2D NMR and FT-ICR-MS. In addition, two compounds (1 and 3) showed strong cytotoxicity against all four cancer cell lines, KB (a human epidermal carcinoma), MCF7 (human breast carcinoma), SK-LU-1 (human lung carcinoma) and HepG2 (hepatocellular carcinoma).
Bioactive Metabolites Produced by the Endophytic Fungus Phomopsis sp. YM355364
Authors: Ma Kai-Xia , Shen Xin-Tian , Huang Rong , Wang Tang , Xie Xiao-Song , Liu Shu-Wen , Wu Shao-Hua , He Jian
Published: March 2019

A new compound, 16-acetoxycytosporone B (1), along with four known ones, dankasterone A (2), dankasterone B (3), 3β,5α,9α-trihydroxy-(22E,24R)-ergosta-7,22-dien-6-one (4), and cyclonerodiol oxide (5), were isolated from Phomopsis sp. YM355364, an endophytic fungus of Aconitum carmichaeli. Their structures were characterized by spectral analysis. Compound 2 exhibited significant inhibitory activity against influenza A/Thailand/Kan353/2004(H5N1) pseudovirus with an IC50 value of 3.56 μM. Compounds 1, 2, and 4 showed either moderate or weak antifungal activities against four pathogenic fungi.
A New Ellagic Acid Glycoside and DNA Topoisomerase IB Inhibitory Activity of Saponins from Putranjiva roxburghii
Authors: Kumar Ashish , Chowdhury Somenath Roy , Chakrabarti Tulika , Majumdar Hemanta K , Jha Tarun , Mukhopadhyay Sibabrata
Published: March 2019

Chemical investigation of the stem bark and leaves of Putranjiva roxburghii has resulted in the isolation of a new ellagic acid glycoside (5) along with four saponins (1-4). The structures of the isolated compounds were established by detailed spectral analysis. Incidentally putranoside-A methyl ester (4) has been isolated for the first time from this species and the saponins (1-4) exhibited potent DNA topoisomerase IB inhibitory activity.
Synthesis of Substituted 1,3-Diesters of Glycerol Using Wittig Chemistry
Authors: Lowe Henry IC , Toyang Ngeh J. , Watson Charah T. , Bryant Joseph
Published: March 2019

1,3-di-O-Cinnamoyl-glycerol is a natural compound isolated from a Jamaican medicinal plant commonly referred to as Ball moss (Tillandsia recurvata). The synthesis of this compound was achieved via a Wittig chemistry process. The synthetic approach started with acylation of a di-protected glycerol with cinnamoyl chloride, deprotection of the glycerol moiety, reaction of the primary alcohol with bromo acetylbromide followed by treatment with triphenyl phosphine to give the corresponding phosphonium bromide. The phosphonium bromide was then converted in situ to the Wittig reagent which is the basis for a novel route to 1,3-di-O-cinnamoyl glycerol. Four analogs were also synthesized, three of which are new and are being reported in this article for the first time. The new compounds include 3-(3,4-diemthoxy-phenyl)-acrylic acid 2-hydroxy-3-(3-ptolyl-acryloyloxy)-propyl ester (3), 2-acetoxy-5-((E)-3-(3-((E’)-3-(3,4-dimethoxyphenyl)acryloyloxy)-2-hydropropoxy)-3-oxoprop-1-enyl)benzoic acid (4) and 4-((E)-3-(3-((E)-3-(3,4-dimethoxyphenyl)acryloyloxy)-2-hydropropoxy)-3-oxoprop-1-enyl)benzoic acid (5). The compounds showed no activity in our anticancer assay.
In vitro Cancer Cell Growth Inhibition and Antioxidant Activity of Bombax ceiba (Bombacaceae) Flower Extracts
Authors: Tundis Rosa , Rashed Khaled , Said Ataa , Menichini Francesco , Loizzo Monica R.
Published: March 2019

The flowers of Bombax ceiba were investigated for their chemical composition, antioxidant effects and antiproliferative activity against seven human cancer cell lines. The antiproliferative responses of diethyl ether (DE) and light petroleum (PE) extracts were evaluated by sulforhodamine B (SRB) assay against MCF-7, HeLa, COR-L23, C32, A375, ACHN, and LNCaP cells in comparison with a human normal cell line, 142BR. Moreover, extracts were characterized by GC-MS analysis and tested for their antioxidant properties by different in vitro systems, namely DPPH, Fe-chelating activity and β-carotene bleaching test. Both PE and DE extracts showed the highest antiproliferative activity against human renal adenocarcinoma (ACHN) in a concentration-dependent manner. PE extract showed the highest radical scavenging activity against the DPPH radical, while DE extract was more active in the β-carotene bleaching test. The presence of β-sitosterol and some fatty acids may contribute to the bioactivity of B. ceiba flower extracts.
Chemical Composition and Antibacterial Activity of Essential Oil and Extracts of Citharexylum spinosum Flowers from Thailand
Authors: Mar Ae , Pripdeevech Patcharee
Published: March 2019

The chemical composition and antibacterial and antioxidant activities of the essential oil and various solvent extracts of Citharexylum spinosum flowers are reported. The chemical compositions were determined by GC-MS with 151 volatile constituents identified. Methyl benzoate, piperitone, maltol, and maple furanone were the major constituents. All extracts were tested for their antibacterial activity against eight microorganisms. The flower oil had the greatest antibacterial activity against all bacterial strains (MIC values of 31.2 μg/mL), while the other solvent extracts had MIC values ranging from 31.2 to 1000 μg/mL. The essential oil had the highest antioxidant activity and total phenol content with IC50 values of 62.7 and 107.3 μg/mL, respectively.
Chemical Composition and Anti-inflammatory Activity of Chamaecyparis obtusa f. formosana Wood Essential Oil from Taiwan
Authors: Chien Tzu-Chao , Lo Sheng-Fong , Ho Chen-Lung
Published: March 2019

Chamaecyparis obtusa Siebold & Zucc. f. formosana Hayata (Cupressaceae) is one of the treasured conifers in Taiwan. In this study, the wood essential oil of the species was extracted and its anti-inflammatory bioactivities analyzed. The composition analysis of the essential oil yielded a total of 57 compounds with α-terpineol (19.4%), τ-muurolol (16.9%), borneol (16%), and α-cadinol (10.9%) predominating. The anti-inflammatory assays of the essential oil suggest that C. obtusa f. formosana wood oil has no cytotoxicity, and was capable of inhibiting the expressions of tumor necrosis factor (TNF-α), IL-6, IL-1, pro IL-1β, NO, iNOS, and NLRP3 in murine macrophage cells. It was unable, however, to inhibit the expression of COX-2. Further investigation of the effect of the essential oil on the cellular signal transduction indicated that it was capable of inhibiting ERK1/2, JNK1/2 and p38; it also showed excellent inhibition against ROS. Thus, the overall results indicated that C. obtusa f. formosana wood oil had very good anti-inflammatory efficacies.
Improved Synthesis of (±)-Trichodiene – A Volatile Marker for Trichothecene Mycotoxins
Authors: Gebauer Julian , Werneburg Martina , Koch Matthias
Published: March 2019

Trichodiene is the first and only volatile intermediate in the biosynthesis of Fusarium mycotoxins and its detection in the gas-phase might therefore be of potential interest as a marker for food safety analysis. We herein present an improved diastereoselective synthesis of trichodiene which can be used as an analytical standard for a headspace gas chromatography / mass spectrometry method to be developed.
Diastereoselective Addition of Diazomethane to Zaluzanin A
Authors: Ortiz-León Adriana , Torres-Valencia J. Martín , Manríquez-Torres J. Jesús , Alvarado-Rodríguez José G. , Hernández-Balderas Uvaldo , Cerda-García-Rojas Carlos M. , Joseph-Nathan Pedro
Published: March 2019

The diastereoselectivity of diazomethane addition to the conjugated double bond of α,β-unsaturated sesquiterpene lactones was explored using zaluzanin A (1) as a model. Thus, the absolute configuration of 1 was assured by X-ray diffraction analysis including evaluation of Flack and Hooft parameters, and by vibrational circular dichroism spectroscopy of its diacetyl derivative 2, while the absolute configuration of the diazomethane addition product, zaluzanin A pyrazoline (3), was determined by evaluation of the 1H NMR chemical shift changes with respect to 1, and confirmed by X-ray diffraction analysis, again including evaluation of Flack and Hooft parameters.
Tauroarenarones A and B, New Taurine-containing Meroterpenoids from the Marine Sponge Dysidea sp
Authors: Utkina Natalia K. , Denisenko Vladimir A.
Published: March 2019

Two new taurine-containing meroterpenoids, both arenarone derivatives, tauroarenarone A (1) and tauroarenarone B (2), have been isolated from the Australian marine sponge Dysidea sp. Their structures were established from NMR spectroscopic data.
Novel Cucurbitane Triterpenoids and Anti-cholinesterase Activities of Constituents from Momordica charantia L
Authors: Kuanhut Wichuta , Aree Thammarat , Pornpakakul Surachai , Sawasdee Pattara
Published: March 2019

The C-19 epimers of 5β,19-epoxycucurbita-6,23( E),25(26)-triene-3β,19-diol (1) and 5β,19-epoxy-25-methoxycucurbita-6,23-diene-3β,19-diol (2) along with (19 R, 23 E)-5β,19-epoxy-19-methoxycucurbita-6,23,25-trien-3β-ol (3), (23 E)-5β,19-epoxycucurbita-6,23-diene-3β,25-diol (4), ligballinol (5), charantin (6) and momordicoside K (7) were isolated from the green fruits of Momordica charantia. The ( S)-epimers of 1 and 2 are the first reports in nature. The acetyl- and butyryl-cholinesterase inhibitory activities of the isolated compounds were evaluated, and 5 showed the highest activity of these compounds against butyrylcholinesterase (IC50 = 32.20 μM) with a reversible and non-competitive inhibition mode.
Immunomodulatory Action of Triterpene Glycosides Isolated from the Sea Cucumber Actinocucumis typica. Structure-Activity Relationships
Authors: Pislyagin Evgeny A. , Aminin Dmitry L. , Silchenko Alexandra S. , Avilov Sergey A. , Andryjashchenko Pelageya V. , Kalinin Vladimir I. , Padmakumar Krishna
Published: March 2019

Stimulation of lysosomal activity and ROS formation in mouse peritoneal macrophages by five triterpene glycosides, typicosides A1 (1), A2 (2), B1 (3), C1 (4) and C2 (5) has been studied and compared with their cytotoxic activities. Glycosides 1–3 possess moderate activities, but the most cytotoxic glycoside 5 is not active. Typicoside C1 (4), with low toxicity, was proved to be the most active concerning stimulation of ROS formation. This is the first example of a triterpene glycoside from sea cucumbers with low cytotoxicity, but which demonstrates a strong immunostimulatory effect on mouse peritoneal macrophages in vitro.
Accumulation and Function of Trigonelline in Non-leguminous Plants
Authors: Ashihara Hiroshi , Watanabe Shin
Published: March 2019

As part of our studies of the occurrence, biosynthesis, function and human use of trigonelline, we looked at trigonelline-accumulating plant species and at the distribution of trigonelline in different organs of trigonelline-accumulating non-leguminous plants. There are many trigonelline-synthesizing plant species, but apart from legume seeds only a few species accumulate high concentrations of trigonelline. We have found only three species that accumulate high levels of trigonelline: Murraya paniculata (orange jessamine), Coffea arabica (coffee) and Mirabilis jalapa (four o'clock flower). Trigonelline was found in all parts of Murraya paniculata seedlings at 4–13 μmol/g fresh weight; more than 70% was distributed in the leaves. In the coffee plant, trigonelline was found in all organs, and the concentrations in the upper stems, including tips (48 μmol/g FW) and seeds (26 μmol/g FW), were higher than in other organs. In Mirabilis jalapa plants, trigonelline was found in leaves, stems, flowers, roots and seeds; the concentration varied from 0.3 to 13 μmol/g FW and was generally higher in young tissues than in mature tissues, except for seeds. Exogenously supplied nicotinamide increases the trigonelline content. The in planta role of trigonelline and the possible use of trigonelline-accumulating plants in herbal medicine are discussed.
Metabolites of the Endophytic Fungus Penicillium sp. FJ-1 of Acanthus ilicifolius
Authors: Liu Jian-Fang , Chen Wei-Jie , Xin Ben-Ru , Lu Jie
Published: March 2019

Two new compounds, named as (2 R,3 S)-pinobanksin-3-cinnamate (1), and 15α-hydroxy-(22 E,24 R)-ergosta-3,5,8(14),22-tetraen-7-one (2), were isolated from the endophytic fungus Penicillium sp. FJ-1 of Acanthus ilicifolius Linn. Their structures were elucidated on the basis of spectroscopic analysis. Additionally, compound 1 exhibited potent neuroprotective effects on corticosterone-damaged PC12 cells, and compound 2 showed potent cytotoxicity on glioma cell lines.
Variability of Procyanidin type A- and -B Trimers Content in Aerial Parts of Some Vaccinium Species and Cultivars
Authors: Toomik Peeter , Püssa Tõnu , Raal Ain
Published: March 2019

Based on the ethnopharmacological data showing that either wild bilberry leaves or whole aerial parts of the plants have been used as antidiabetic drugs, it can be hypothesized that the controversial results of various clinical and animal investigations may be caused by different contents of the active principles in different aerial parts of the bilberry/blueberry ( Vaccinium spp.) plants, as well as by their geographical and seasonal variability. The aim of this study was to compare the content of procyanidin type A- and -B trimers in different parts of wild bilberry ( Vaccinium myrtillus L.) and northern highbush blueberry ( V. corymbosum L.) cultivars. Stems (60 samples) and leaves (30 samples) of wild bilberries and northern highbush blueberry cultivars ‘Ama’ and ‘North Blue’ were collected at different locations in Estonia around the year, and analyzed for the concentration of the target polyphenols by HPLC-MS/MS. The highest content of type A doubly linked trimer, a known antidiabetic substance, was established in the stems of V. myrtillus. These contained up to 100 times more of the active substance than the leaves of V. myrtillus and at least 1000 times more than the leaves of V. corymbosum, whereas the seasonal/geographical variation was nearly tenfold. We suggest using stems of V. myrtillus for future animal and clinical investigations of bilberry preparations against diabetes.
Three New Isoflavonoids from Erythrina caffra
Authors: Desta Zelalem Yibralign , Majinda Runner R. T.
Published: March 2019

Three new isoflavonoids, 5,7-dihydroxy-2′,4′-dimethoxy-5′-(3-methylbut-2-enyl) isoflavanone (erycaffra A) (1), 5,7-dihydroxy-2′,4′-dimethoxy-5′-(2-hydroxy-3-methylbut-3-enyl)isoflavanone (erycaffra B) (2), and 5,7-dihydroxy-6,8-di-(2-hydroxy-3-methylbut-3-enyl)isoflavone (erycaffra C) (3), were isolated from the stem bark of E. caffra Thunb., along with eight known compounds, namely, alpinumisoflavone (4), isoerysenegalensein E (5), β-amyrin (6), oleanolic acid (7), octacosyl- E-ferulate (8), triacontyl-4-hydroxycinnamate (9), n-tetracosyl p-coumarate (10) and octacosan-1-ol (11). The structures were determined on the basis of spectroscopic (1D, 2D-NMR) and MS data and by comparison with literature values.
Bijayasaline: A New C-Glucosyl-α-hydroxydihydrochalcone from the Heartwood of Bijayasal (Pterocarpus marsupium)
Authors: Joshi Khem Raj , Devkota Hari Prasad , Yahara Shoji
Published: March 2019

A new C-glucosyl-α-hydroxydihydrochalcone derivative, (α S)-3′- C-β-glucopyranosyl-α,3,4,2′4′-pentahydroxydihydrochalcone, named as bijayasaline (1) was isolated from the heartwood of Bijayasal (Pterocarpus marsupium) and characterized on the basis of NMR and circular dichroism (CD) spectral data. Bijayasaline (1) showed potent DPPH free radical scavenging activity.
Nelumal A, the Active Principle of Ligularia nelumbifolia, is a Novel Aromatase Inhibitor
Authors: Epifano Francesco , Genovese Salvatore , Fiorito Serena , Nde Chantal Magne , Clyne Colin
Published: March 2019

Nelumal A, the active principle of Ligularia nelumbifolia was preliminarily tested as an aromatase inhibitors in HEK293 cells transfected with aromatase cDNA and using anastrazole as the reference drug. This screening revealed that it showed an appreciable level of inhibition. Subsequent experiments aimed to evaluate the aromatase activity and expression in KGN cells confirmed that the title natural product, after an incubation of 48 h, compared favourably with anastrazole (1 μM) in the concentration range 10 - 30 μM. Moreover, nelumal A (30 μM) abolished the aromatase mRNA expression in the same cell line.
HPLC-PDA Simultaneous Determination and Protective Effect of Anemarrhena asphodeloides Against Acute Renal Failure
Authors: Seo Chang-Seob , Ha Hyekyung , Kim Young-Jung , Jung Ju-Young
Published: March 2019

We investigated the protective effects against acute renal failure (ARF) of Anemarrhena asphodeloides (AA) and performed simultaneous analysis of three compounds, neomangiferin (1), mangiferin (2), and isomangiferin (3) in AA using a high-performance liquid chromatography-photodiode array. To measure the protective effect of ARF, the levels of reactive oxygen species (ROS) and glutathione depletion were determined using a kit. HPLC analysis was performed using a Gemini C18 column at 40°C. The mobile phase used gradient elution with 1.0% (v/v) aqueous acetic acid (A) and 1.0% (v/v) acetic acid in acetonitrile (B). The flow rate was 1.0 mL/min. In our assay, AA extract inhibits cisplatin-induced production of intracellular ROS. Pre-incubation of AA extracts (10–200 μg/mL) markedly maintained cell viability compared with controls in the noncisplatin-treated cells. Calibration curves of all compounds showed good linearity ( r2  0.9992). Recoveries of the three compounds were 98.9–103.4%. The relative standard deviations of intra- and inter-day precision were 0.07–1.73% and 0.12–1.49%, respectively. The amounts of the three components were 1.22–20.63 mg/g. The AA extract has potential as a therapeutic agent for treatment of ARF. In addition, the established method will help to improve quality control of AA.
New Rocaglamide Derivatives from Vietnamese Aglaia species
Authors: Duong Ngoc Tu , Edrada-Ebel RuAngelie , Ebel Rainer , Lin Wenhan , Duong Anh Tuan , Dang Xuan Quy , Nguyen Ngoc Hieu , Proksch Peter
Published: March 2019

Phytochemical analysis of the leaves of different Aglaia species collected in Vietnam yielded eight rocaglamide derivatives, which are responsible for the strong insecticidal activity against Spodoptera littoralis, including rocaglamide A (1), rocaglamide I (2), rocaglamide W (3), rocaglamide AB (4), rocaglamide J (5), rocaglaol (6), rocaglamide S (7) and the new rocaglamide AY (8). The structures of these compounds were elucidated through extensive 1D and 2D NMR spectroscopy and analysis of their mass spectrometric (ESI-MS) and HRESIMS data.
Concerning the Structure of Islandoquinone Isolated from the Lichen Cetraria islandica
Authors: Borisova Ksenia L. , Pelageev Dmitry N. , Kochergina Tatiana Yu. , Pokhilo Nataly D. , Pushilin Michael A. , Denisenko Vladimir A. , Berdyshev Dmitry V. , Anufriev Victor Ph.
Published: March 2019

An investigation of the oxidative coupling products of some substituted hydroxynaphthazarins led to a revision of the proposed structure of islandoquinone, previously isolated from the lichen Cetraria islandica, and yielding (7a S*,13a S*)-6,7a-diethyl-2,5,9,11,12,13a-hexahydroxy-7,14-dioxabenzo[ a]tetracene-1,4,8,13(7a H,13a H)-tetraone through X-ray diffraction analysis of its 2,11-dimethyl ether.