bluuebunny/crossref_metadata_2025 huggingface dataset:
Anticonvulsant Activity of the Linalool Enantiomers and Racemate: Investigation of Chiral Influence
Authors: de Sousa Damião P. , Nóbrega Franklin F. F. , Santos Camila C. M. P. , de Almeida Reinaldo N.
Published: March 2019

The anticonvulsant activity of the racemate and enantiomers of linalool have been evaluated. Pretreatment of the mice with ( S)-(+)-, ( R)-(-)- and rac-linalool increased the latency of convulsions significantly in the PTZ model. Only rac-linalool had an effect at the dose of 200 mg/kg. The enantiomers and their racemic mixture were effective in inhibiting the convulsant effect of PTZ at the dose of 300 mg/kg. The linalools presented pharmacological activity close to that of diazepam. In the PIC seizure model, ( R)-(-)-linalool and rac-linalool presented activity at the dose of 200 mg/kg, but the rac-linalool was more potent than ( R)-(-)-linalool; ( S)-(+)-linalool had no effect at this dose. On the other hand, at the dose of 300 mg/kg this enantiomer was effective, but less potent than ( R)-(-)-linalool and rac-linalool. In the MES model, linalools decreased the convulsion time of the mice in the doses of 200 and 300 mg/kg. rac-Linalool presented maximum effect at 300 mg/kg. Surprisingly, it increased significantly the convulsion time at a dose of 100 mg/kg. Using the parameter of tonic hind convulsions, only ( R)-(-)-linalool produced protection from tonic extension at the dose of 200 mg/kg. When the (+)- and (-)-enantiomers, and rac-linalool were administered at the dose of 300 mg/kg they were also effective in preventing tonic convulsions induced by transcorneal electroshock in the animals. The (+)- and (-)-forms were equipotent and the rac-linalool was more effective than phenytoin. We have demonstrated that the two enantiomers have similar qualitative anticonvulsant activity, but show different potencies.
Kinetic Analysis of Genipin Degradation in Aqueous Solution
Authors: Slusarewicz Paul , Zhu Keng , Hedman Tom
Published: March 2019

Degradation of genipin (GP), a low toxicity natural protein crosslinking agent, in aqueous solution was monitored by HPLC at various pH levels. Degradation of GP was consistent with a mechanism consisting of a first order reaction with a reversible first step. Formation of the intermediate was slowest at more neutral pHs while formation of the irreversible product was correlated to increasing alkalinity. Degradation at all pHs was enhanced by the presence of phosphate ions. Degradation of GP most likely proceeds via the reversible opening of the dihydropyran ring by water followed by irreversible polymerization of the intermediate. Degraded solutions containing no detectable GP or intermediate, however, are still capable of crosslinking proteins.
Microbial Transformation of Marine Halogenated Sesquiterpenes
Authors: Martin Aurelio San , Rovinosa Juana , Carrasco Alvaro , Orejarena Silvia , Soto-Delgado Jorge , Contreras Renato , Chamy M. Cristina
Published: March 2019

The sesquiterpene pacifenol is one of the main constituents of the red alga Laurencia claviformis. Earlier work on the semisynthetic derivatives of pacifenol afforded a series of halogenated sesquiterpenes. The aim of the present work was to obtain new hydroxylated derivatives of halogenated sesquiterpenes by means of microbial transformation using Aspergillus níger, Gibberella fujikuroi and Mucor plumbeus. The best results were obtained with M. plumbeus. The microbiological transformation by M. plumbeus of pacifenol, and two semisynthetic derivatives, is described. The structures of the new compounds obtained were determined by spectroscopic means.
Three New 18-Oxygenated ent-Kaurane Diterpenoids from Isodon leucophyllus
Authors: Zhang Hai Bo , Pu Jian Xin , Zhao Yong , He Fei , Zhao Wei , Lou Li Guang , Xiao Wei Lie , Sun Han Dong
Published: March 2019

Three new 18-oxygenated ent-kaurane diterpenoids, isoleuconins A-C (1–3) and ten known diterpenoids were isolated from the aerial parts of Isodon leucophyllus. The structures were elucidated by 1D and 2D NMR spectroscopic analysis. All of the compounds were evaluated for their cytotoxicity. Rabdokunmin A (13) showed significant cytotoxicity against HT-29 cells, with an IC50 value of 6.2 μM.
Three New Aaptamines from the Marine Sponge Aaptos sp. and Their Proapoptotic Properties
Authors: Shubina Larisa K. , Makarieva Tatyana N. , Dyshlovoy Sergey A. , Fedorov Sergey N. , Dmitrenok Pavel S. , Stonik Valentin A.
Published: March 2019

Three new aaptamine-type alkaloids, 2,3-dihydro-2,3-dioxoaaptamine (1), 6 -( N-morpholinyl)-4,5-dihydro-5-oxo-demethyl(oxy)aaptamine (2) and 3-(methylamino)demethyl(oxy)aaptamine (3), along with known aaptamines were isolated from the sponge Aaptos sp. Their structures were determined on the basis of detailed analysis of their 1D and 2D NMR spectroscopic and mass spectral data. The isolated compounds induced apoptosis in human leukemia THP-1 cells.
Effect of Different Strains of Agrobacterium rhizogenes and Nature of Explants on Plumbago indica Hairy Root Culture with Special Emphasis on Root Biomass and Plumbagin Production
Authors: Gangopadhyay Moumita , Dewanjee Saikat , Bhattacharyya Somnath , Bhattacharya Sabita
Published: March 2019

The aim of the present study was to determine the effect of three strains of Agrobacterium rhizogenes (ATCC 15834, A4 and LBA 9402) and the nature of explants (leaf and stem) on hairy root induction, growth and plumbagin production in Plumbago indica. The first appearance of hairy roots, the transformation frequency, dry root biomass and plumbagin accumulation were found to be maximum in hairy roots induced in leaf explants infected with A. rhizogenes ATCC 15834 as compared with the other two bacterial strains. The hairy roots generated from stem explants infected with all three strains were not found to be productive in terms of the selected parameters. Finally, the insertion of the rolB gene of A. rhizogenes ATCC 15834 in hairy roots of P. indica derived from leaf explants was confirmed by PCR analysis.
Effect of Hibiscus sabdariffa and its Anthocyanins on Some Reproductive Aspects in Rats
Authors: Ali Badreldin H. , Al-Lawati Intisar , Beegam Sumyia , Ziada Amal , salam Suhail Al , Nemmar Abderrahim , Blunden Gerald
Published: March 2019

An aqueous extract of Hibiscus sabdariffa L. is a common beverage in many parts of the world. Reports on its effect on reproduction are conflicting, with anecdotal evidence that the plant is an aphrodisiac, while others report that it is estrogenic, and adversely affects spermatogenesis in rats. We have studied the effect of different concentrations of aqueous extracts of H. sabdariffa calyces (10%, 15% and 20%) used as drinking water for 10 consecutive weeks, and its anthocyanins (50, 100, 200 mg/kg for 5 days, orally) on the weight and histology of the testis, and on some biochemical constituents in testicular homogenates, in addition to the plasma concentrations of testosterone, luteinizing hormone and estradiol. The possible presence of an estrogenic effect of the extract and anthocyanins on the uteri of immature female rats was also tested. Neither the H. sabdariffa extract nor the anthocyanins significantly altered either testicular weight and histology, or uterus weight. Plasma concentrations of the three hormones studied, the testicular concentrations of protein, reduced glutathione and total cholesterol, and superoxide dismutase activity were all insignificantly affected by either the extract or the anthocyanins, except for a slight, but statistically significant, decrease in testicular protein concentration caused by the 15% aqueous extract when compared with controls. These results suggest that H. sabdariffa exerts no adverse effect on the male reproductive system. Consumption of H. sabdariffa aqueous extract inhibited the growth of the rats compared with the controls.
Analysis of Danshen and Twelve Related Salvia Species
Authors: Lu Luyang , Liu Yuan , Zhang Zhifeng , Zhang Hao
Published: March 2019

Danshen is a commonly used traditional Chinese herb, but over twenty Salvia species are used as Danshen by local herbalists. In this study, twelve Salvia species from the plateau of Sichuan and Yunnan Provinces were collected, analyzed and compared with Danshen by HPLC. The results showed that most of the Salvia species were good sources of rosmarinic acid and tanshinones. The highest amount of both rosmarinic acid and tanshinone IIA were found in S. przewalskii Maxim. These results pave the way for a better therapeutic exploitation of these plants.
Meliloester, a New Melilotic Ester from Melilotus alba
Authors: Khatoon Rasheeda , Saba Nikhat , Zahoor Aqib , Summer Shazia , Ahmad Viqar Uddin
Published: March 2019

A new melilotic ester, meliloester [2-ethyl-hexyl-3-(2-hydroxyphenyl) propionate], was isolated from the whole plant of Melilotus alba. Its structure was elucidated on the basis of spectroscopic and mass spectrometric analyses, including EI-MS, HR-MS, and UV, IR, 1D and 2D -NMR spectroscopic studies.
Fast Quality Assessment of German Chamomile (Matricaria chamomilla L.) by Headspace Solid-Phase Microextraction: Influence of Flower Development Stage
Authors: Rafieiolhossaini Mohammad , Adams An , Sodaeizadeh Hamid , Van Damme Patrick , De Kimpe Norbert
Published: March 2019

For an adequate quality evaluation of aromatic plants grown under different conditions, a rapid, simple and sensitive method for the analysis of volatile constituents is indispensable. The main objective of the present study was to compare fast screening of German chamomile ( Matricaria chamomilla L.) by means of headspace solid-phase microextraction (HS-SPME) with conventional isolation of the essential oil (steam distillation-solvent extraction (SDSE)) for the differentiation of chamomile essential oil constituents. Flowers were harvested at two distinct development stages: stage I, when ligulate flowers start to develop and tubular flowers are still closed, and stage II, when tubular flowers are partially to completely opened.

Dried chamomile flowers at two development stages were extracted by means of both SDSE and HS-SPME, followed by GC-MS analysis. Among 30 compounds detected, ( E)-β-farnesene (49%), artemisia ketone (10%) and germacrene D (9%) were the predominant volatile components in the HS-SPME-extract, while α-bisabolol oxide A (42%), chamazulene (21%) and ( Z)-spiroether (8%) were the main essential oil constituents among the 13 compounds obtained by SDSE. After statistical analysis of the data, both techniques enabled the same conclusion: ( E)-β-farnesene was the only compound which showed significant differences between the two flower development stages.

These results suggest that HS-SPME-GC-MS can be used as a sensitive technique for the rapid screening and quality assessment of M. chamomilla.
Composition, Antioxidant and Antimicrobial Activities of the Leaf Essential Oil of Machilus Japonica from Taiwan
Authors: Ho Chen-Lung , Su Yu-Chang
Published: March 2019

The chemical composition, and antioxidant and antimicrobial activities of the essential oil isolated from the leaf of Machilus japonica from Taiwan have been investigated. The essential oil from the fresh leaves was isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC-FID and GC-MS. A total of 97 compounds were identified, representing 100% of the oil. The main components identified were α-phellandrene (14.5%), α-pinene (12.8%), thymol (12.6%), β-pinene (8.3%), α-terpineol (6.5%) and carvacrol (6.0%). The antioxidant activity of the oil was tested by the DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical scavenging capability test. The results showed that the IC50 was 51.8 μg/mL. The antimicrobial activity of the oil was tested by the disc diffusion and micro-broth dilution methods against ten microbial species. The oil exhibited strong growth suppression against Gram-positive bacteria and yeast, with inhibition zones of 48~54 mm and MIC values of 16.12~32.25 μg/mL, respectively. For the antioxidant and antimicrobial activities of the oil, the active source compounds were determined to be thymol and carvacrol.
Chemical Composition, Antimicrobial, Antiradical and Anticholinesterase activity of the Essential Oil of Pulicaria stephanocarpa from Soqotra
Authors: Ali Nasser A. Awadh , Crouch Rebecca A. , Al-Fatimi Mohamed A. , Arnold Norbert , Teichert Axel , Setzer William N. , Wessjohann Ludger
Published: March 2019

The chemical composition of the hydrodistilled leaf essential oil from Pulicaria stephanocarpa Balf Fil was determined by GC-MS analysis, and its antimicrobial, antioxidant and anticholinesterase (AChE) activities were evaluated. Eighty-three compounds were identified representing 97.2% of the total oil. ( E)-Caryophyllene 13.4%, ( E)-nerolidol 8.5%, caryophyllene oxide 8.5%, α-cadinol 8.2% spathulenol 6.8% and τ-cadinol 4.7%, were the main components. Antimicrobial activity of the oil, evaluated using the disc diffusion and broth dilution methods, demonstrated the highest susceptibility on Gram-positive bacteria and Candida albicans. The free radical scavenging ability of the oil was assessed by the DPPH assay to show antiradical activity with IC50 of 330 μg/mL. Moreover, the oil revealed an AChE inhibitory activity of 47% at a concentration of 200 μg/mL using Ellman's method.
Composition of the Essential Oils and Antibacterial Activities of Hymenocrater yazdianus, Stachys obtusicrena and Nepeta asterotricha Three Labiatae Herbs Growing Wild in Iran
Authors: Masoudi Shiva , Rustaiyan Abdolhossein , Mohebat Razieh , Mosslemin Mohammad Hossein
Published: March 2019

Water-distilled essential oils from leaves of Hymenocrater yazdianus Rech.f., flowers of Stachys obtusicrena Boiss., and stems and flowers of Nepeta asterotricha Rech.f, which are endemic to Iran, were analyzed by GC and GC/MS. Fifty-five components of the leaf oil of H. yazdianus were characterized, representing 95.1% of the total components detected. The major constituents were identified as 1,8-cineole (17.6%), β-caryophyllene (13.9%), α-pinene (10.6%) and caryophyllene oxide (10.4%). Germacrene-D (37.5%) and α-bisabolol (23.5%) were the main components among the twenty constituents characterized in the flower oil of S. obtusicrena, representing 90.8% of the total components detected. Thirty-five compounds representing 93.0% of the stem oil of N. asterotrica were identified among which terpinen-4-ol (22.8%) and γ-terpinene (14.1%) were the major ones. The flower oil of the species was characterized by higher amounts of terpinen-4-ol (24.8%), 4aα, 7aβ-nepetalactone (18.2%) and 1,8-cineole (11.6%) among the thirty-three components comprising 98.5% of the total oil detected.

The antibacterial activity of the stem, leaf and flower oils of Hymenocrater yazdianus, Stachys obtusicrena and Nepeta asterotricha against seven Gram-positive and Gram-negative bacteria were determined using the MIC method. The growth inhibitory zone (mm) was also measured.
Evaluation of the Anti-Leishmania Major Activity of Satureja Bakhtiarica Essential Oil in Vitro
Authors: Mohammadpour Ghasem , Marzony Eisa Tahmasbpour , Farahmand Mahin
Published: March 2019

Leishmaniasis is a painless chronic skin disease that is caused by the protozoan parasite Leishmania. Due to the importance of this disease and the side effects of chemical drugs, use of drugs of plant origin to treat Leishmaniasis is very important. In the present study, the chemical composition and the anti- Leishmania major activity of the essential oils obtained from Satureja bakhtiarica were evaluated in vitro. The oils were extracted using a Clevenger apparatus and then the chemical composition was analyzed by GC-MS. Promastigotes of L. major were cultured in both N.N.N and RPMI1640 media. GC-MS analysis showed 13 compounds, in which the major components were the phenolic (37.4%) compounds, thymol (22.6%) and p-cymene (19.3%). The essential oil of S. bakhtiarica showed higher activity against L. major than the standard anti-Leishmania drug, glucantime,. Perhaps because of the high concentration of phenolic compounds in the essential oil, all the parasites were killed after 24 hours. The essential oil from S. bakhtiarica is a potential plant drug against leishmaniasis. Further studies are necessary to evaluate this oil in animal models ( in vivo) for future drug applications.
Antiviral Furanosesquiterpenes from Commiphora erythraea
Authors: Cenci Elio , Messina Federica , Rossi Elisabetta , Epifano Francesco , Marcotullio Maria Carla
Published: March 2019

The crude methanolic extract obtained from C. erythraea resin was chromatographed on silica gel with solvent of increasing polarity. The extract and fractions were evaluated for cytotoxicity and antiviral activity [parainfluenza type 3 virus (PIV3)] by plaque forming units (PFU) reduction assay using HEp-2 cells (human larynx epidermoid carcinoma cell line). From the active fraction, five compounds were isolated and tested. Only two of these showed anti-PIV3 activity with a selectivity index (SI) of 66.6 and 17.5, respectively. Both the compounds are furanosesquiterpenoids.
A Novel Anticancer Diterpenoid from Jatropha Gossypifolia
Authors: Falodun Abiodun , Kragl Udo , Touem Serge-Mitherand Tengho , Villinger Alexander , Fahrenwaldt Thomas , Langer Peter
Published: March 2019

Jatropha gossypifolia root bark is used in ethnomedicine for bacterial infections and cancer of the lungs. Phytochemical investigation resulted in the isolation and characterization of a potent anticancer and novel lathyrane diterpenoid compound, abiodone, with an unusual methylene group. The structure of this novel compound was established by 1D, and 2D NMR spectroscopic experiments and confirmed by X-ray analysis.
Physical Properties and Molecular Conformations of Indole Alkaloids and Model Protein Interactions – Theoretical vs. Experimental Study
Authors: Ivanova Bojidarka , Spiteller Michael
Published: March 2019

The physical properties and molecular structure of five natural indole alkaloids (IAs) and their interaction with protein targets have been studied, experimentally and theoretically. Electronic absorption (EAs) and CD spectroscopy, electrospray ionization (ESI) and matrix-assisted laser desorption/ionization (MALDI) mass spectrometry (MS), as well as imaging mass spectrometric techniques (IMS) were used, analyzing the isolated alkaloids and corresponding IAs/protein molecular complexes. Theoretical quantum chemical DFT calculations were also applied. The mechanism of their biological activity and structure-activity relationship as potential neurologically active compounds were studied, using the model interactions with 5HT2A receptors. The gas-phase stable molecular fragments of the IAs are discussed comparing the experimental mass spectrometric data and theoretical quantum chemical DFT calculations of the different molecular fragments of the IAs.
Synthesis of Uliginosins A and B
Authors: Kraus George A. , Liu Feng
Published: March 2019

The uliginosins have potentially very useful biological activity, but their availability from natural sources is limited. Moreover, the one synthesis can not be reproduced. Here we report reproducible conditions for the synthesis of the uliginosins.
Biotransformation of Gambogenic Acid by Chaetomium Globosum CICC 2445
Authors: Tao Si-Jia , Wang Yang , Zhang Xing , Guan Shu-Hong , Guo De-An
Published: March 2019

Microbial transformation of gambogenic acid (1), a caged polyprenylated xanthone isolated from the resin of Garcinia hanburyi, was carried out with Chaetomium globosum CICC 2445, after screening forty-six strains of filamentous fungi. A new caged polyprenylated xanthone, 16,17-dihydroxygambogenic acid (2), was specifically obtained, as a result of hydroxylation at C-16, and C-17. Its structure was elucidated on the basis of spectroscopic methods. The cytotoxicity of compounds 1 and 2 against HeLa tumor cell line was evaluated, with both of them being modestly active.
Composition, Antioxidant, Antimicrobial and Anti-wood-decay Fungal Activities of the Twig Essential Oil of Taiwania cryptomerioides from Taiwan
Authors: Ho Chen-Lung , Yang Su- Sing , Chang Tsong-Min , Su Yu-Chang
Published: March 2019

This study investigated the chemical composition, antioxidant, antimicrobial and anti-wood-decay fungal activities of the essential oil isolated from the twigs of Taiwania cryptomerioides from Taiwan. The essential oil was isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC-FID and GC-MS. A total of 35 compounds were identified, representing 100% of the oil. The main components identified were α-cadinol (45.9%), ferruginol (18.9%) and β-eudesmol (10.8%). The antioxidant activity of the oil was tested by the DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical scavenging capability test. The results showed an IC50 of 90.8 ± 0.2 μg/mL. The active source compound was ferruginol. The antimicrobial activity of the oil was tested by the disc diffusion and micro-broth dilution methods against ten microbial species. The oil exhibited strong growth suppression against Gram-positive bacteria and yeast with inhibition zones of 45~52 mm and MIC values of 31.25~62.5 μg/mL, respectively. The anti-wood-decay fungal activity of the oil was also evaluated. The oil demonstrated excellent activity against four wood-decay-fungal species. For the antimicrobial and anti-wood-decay fungal activities of the oil, the active source compounds were determined to be α-cadinol, β-eudesmol and ferruginol.
Aurones: Interesting Natural and Synthetic Compounds with Emerging Biological Potential
Authors: Zwergel Clemens , Gaascht François , Valente Sergio , Diederich Marc , Bagrel Denyse , Kirsch Gilbert
Published: March 2019

Aurones [2-benzylidenebenzofuran-3(2H)-ones] are either natural or synthetic compounds, belonging to the flavonoid family. They are isomeric to flavones and provide a bright yellow color to the plants in which they occur. Today, a literature survey indicates that the related flavonoids have been studied not only for their physiological properties and effects on Nature, but also for their therapeutic potential. Aurones are recently attracting the interest of an increasing number of research groups, and, since the last review, some interesting advances have been made in understanding the aurones.

In this review, we report the recent advances made on the synthetic routes towards aurones. We also highlight their activity in different biological areas, as well as applied genetic plant modifications to produce these colored compounds. Their synthesis, structure–activity relationships and the importance of the substitution pattern will also be mentioned. Finally, some aspects regarding the possible development of aurones will be discussed briefly.
Interactions of Calix[n]arenes with Nucleic Acids
Authors: Peters Max Sena , Li Miao , Schrader Thomas
Published: March 2019

DNA interaction with artificial binders is of great interest, especially in light of the broad range of possible biomedical applications. The growing understanding of replication, transcription and translation opened the path for new approaches to target pathological effects at a very early stage. Meanwhile, the competitive binding to nucleic acids by designed molecules, which, for example, block certain sequences for natural binders, such as transcription factors, has become a promising concept in the context of gene therapy. On the other extreme, the transport of nucleic acids over the cell membrane into the nucleus by transfection agents opens the possibility to reprogram protein biosynthesis within host cells.

In the past decades several substance classes have been developed for a noncovalent specific DNA binding with predictable biological effects, such as peptide nucleic acids or polyamide ligands. Calixarenes have not received so much attention, although they consist of a compact aromatic core tuneable in size, and allow the introduction of cationic functionalities at their upper and lower rims. Formerly being utilized as receptor moieties due to the possibility of complexating guests in their cavities, calixarenes are now also used as molecular scaffolds for multivalent ligands and are, therefore, suitable tools for cooperative DNA complexation.

This review surveys specific supramolecular interactions between calixarene derivatives and nucleic acids, with an emphasis on structural elements in the calixarenes and the biological consequences of their complex formation with DNA strands.
Complex Diversity in Ligularia Kanaitzensis
Authors: Shimizu Anna , Suzuki Yurika , Torihata Atsushi , Hanai Ryo , Saito Yoshinori , Tori Motoo , Gong Xun , Kuroda Chiaki
Published: March 2019

Two samples of Ligularia kanaitzensis collected in the Shizhongshan Mountain region of Yunnan Province, as well as one sample collected in Sichuan Province, were analyzed with regard to root constituents and neutral DNA sequences. The two Shizhongshan samples were found to be different from each other and from other samples analyzed previously, indicating that the intra-specific diversity in the species was highly complex.
Enantioselective Synthesis of the Bisabolane Sesquiterpene (+)-1-Hydroxy-1,3,5-Bisabolatrien-10-one and Revision of its Absolute Configuration
Authors: Serra Stefano
Published: March 2019

The enantioselective synthesis of ( S)-1-hydroxy-1,3,5-bisabolatrien-10-one 1 is here described. This sesquiterpene was prepared using ( S)-3-(2-methoxy-4-methyl-phenyl)butan-1-ol as a chiral building block. Two different pathways were employed and both turned out to be high yielding, affording 1 in good chemical purity and without any racemization of the existing stereocenter. The spectroscopic data of the synthetic ( S)-1 were in very good agreement with those reported for the natural compound, which was extracted from Juniperus formosana heartwood and from the leaves of J. chinensis. The positive sign of the measured optical rotation value of synthetic ( S)-1 allows the unambiguous assignment of the absolute configuration of (+)-1 as the ( S)-enantiomer. This finding corrects the previous configuration determination which indicated the opposite result. At last, since even ( R)-3-(2-methoxy-4-methyl-phenyl)butan-1-ol is preparable in high enantiomer purity by mean of a different biocatalytic process, the formal synthesis of natural ( R)-1 was also accomplished.
New Meroterpenoids from the Marine Sponge Aka coralliphaga
Authors: Shubina Larisa K. , Kalinovsky Anatoly I. , Makarieva Tatyana N. , Fedorov Sergey N. , Dyshlovoy Sergey A. , Dmitrenok Pavel S. , Kapustina Irina I. , Mollo Ernesto , Utkina Natalia K. , Krasokhin Vladimir B. , Denisenko Vladimir A. , Stonik Valentin A.
Published: March 2019

Three new sulfated meroterpenoids containing sesquiterpene and hydroquinone moieties, namely siphonodictyal A sulfate (1), akadisulfate A (2) and akadisulfate B (3), along with the known siphonodictyal B3 and bis(sulfato)-cyclosiphonodictyol A were isolated from the sponge Aka coralliphaga. Their structures were elucidated on the basis of spectroscopic data. Akadisulfate B and siphonodictyal B3 showed a radical-scavenging activity comparable with that of the known lipophylic antioxidant BHT.
New Triterpenoid Saponins from Leaves of Panax Japonicus (3). Saponins of the Specimens Collected in Miyazaki Prefecture
Authors: Yoshizaki Kouichi , Yahara Shoji
Published: March 2019

Two new dammarane-type triterpenoid saponins, chikusetsusaponin LM1 (1), chikusetsusaponin LM2 (2), and three known triterpenoid saponins, ginsenoside Re (3), ginsenoside Rg1 (4), ginsenoside F3 (5), were isolated from the leaves of P. japonicus C. A. Meyer collected in Miyazaki prefecture, Japan. The structures of new chikusetsusaponins were elucidated on the basis of spectroscopic and physicochemical evidences.
Ardisikivuoside, A New Triterpenoid Saponin from Ardisia Kivuensis (Myrsinaceae)
Authors: Ndontsa Blanche L. , Tchinda Alembert , Teponno Rémy B. , Mpetga James S. , Frédérich Michel , Tane Pierre
Published: March 2019

Column chromatography of the n-butanol extract of the stem of Ardisia kivuensis (Myrsinaceae) led to the isolation of a new triterpenoid saponin, ardisikivuoside (1) {3- O-β-D-xylopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-3β-hydroxy-13β,28-epoxyoleanan-16-oxo-30-al}. The structure was elucidated on the basis of spectral studies.
Triterpene Glycosides from the Sea Cucumber Eupentacta fraudatrix. Structure and Biological Action of Cucumariosides A1, A3, A4, A5, A6, A12 and A15, Seven New Minor Non-sulfated Tetraosides and Unprecedented 25-Keto, 27-Norholostane Aglycone
Authors: Silchenko Alexandra S. , Kalinovsky Anatoly I. , Avilov Sergey A. , Andryjaschenko Pelageya V. , Dmitrenok Pavel S. , Martyyas Ekaterina A. , Kalinin Vladimir I.
Published: March 2019

Seven new minor triterpene glycosides, cucumariosides A1 (1), A3 (2), A4 (3), A5 (4), A6 (5), A12 (6) and A15 (7) have been isolated from the Far Eastern sea cucumber Eupentacta fraudatrix. Structures of the glycosides were elucidated by 2D NMR spectroscopy and MS. Glycosides 1–7 belong to the group of cucumariosides A, having linear tetrasaccharide carbohydrate moieties without any sulfate group and possessing 3- O-methyl-D-xylose as a terminal monosaccharide unit. The latter peculiarity is rare in sea cucumber glycosides, but typical for the glycosides from E. fraudatrix. Glycosides 1–7 differ from each other by side chain structures in the aglycone moieties; three of them have unique structural features. The first is the presence of a 25-butoxy-group in the side chain of cucumarioside A3 (2), the second is a 23 E,25-diene system in cucumarioside A6 (5) and the third is a 25-keto-27-nor-holostane aglycone in cucumarioside A12 (6); these were never previously found in sea cucumber glycosides. Cytotoxic activity of glycosides 1–7 against mouse spleen lymphocytes and the cells of the ascite form of mouse Ehrlich carcinoma, along with hemolytic activity against mouse erythrocytes and antifungal activity were studied. Glycosides 1 and 5 were the most active in all the tests.
Effect of some ent -Kaurenes on the Viability of Human Peripheral Blood Mononuclear Cells
Authors: Cordero Yndra , Corao Grecia M. , Cova José A. , Usubillaga Alfredo
Published: March 2019

The possible cytotoxic activity of some ent-kaurenes on human mononuclear cells, obtained from peripheral blood, was studied having in mind future studies on their antitumor activity. The cells were obtained using the Ficoll-Hypaque method, adjusted to 2×106cells/mL, and incubated with kaurenes for 48 hours at 3×10-5, 30×10−5, 300×10−5 and 3000×10−5μmol/well. Ent-kaurenic acid showed no toxicity at all concentrations studied. The least toxic of all the kaurene derivatives studied was ent -15,16-epoxy-17-acetoxy-(-)-kauran-19-oic acid, with a cellular viability of 99% at 3×10−5μmol/well, and 94% at 30×10−5μmol/well. Another compound that showed low toxicity was the 2,3,4,6-tetra-acetyl-α-D-pyranosyl ester of ent-15-oxo-(-)-kaur-16-en-19-oic acid with 44% viability at 3000×10−5Vmol/well. The most toxic compounds at all concentrations tested were ent-kaur-16-en-19-ol acetate and ent-16α-hydroxy-(-)-kauran-19-oic acid. On the other hand, ent-kaur-9(11)16-dien-19-oic acid, ent-kauran-19-oic acid, and ent-kaur-16-en-19-ol were toxic only at the highest concentration studied. According to these results, and considering the concentrations employed, ent-kaur-16-en-19-oic acid and ent-15,16-epoxy-17-acetoxy-(-)-kauran-19-oic acid could be used for in vivo experiments and possibly for therapeutic purposes on humans, without much risk.
GC-MS Analysis of Aroma of Medemia argun (Mama-n-Khanen or Mama-n-Xanin), an Ancient Egyptian Fruit Palm
Authors: Hamed Arafa I. , Leonardi Michele , Stochmal Anna , Oleszek Wieslaw , Pistelli Luisa
Published: March 2019

The fruits of the edible and medicinal Egyptian palm, Medemia argun, were collected from Aswan in Egypt and the essential oil (EO) from fruits and headspace (HS) of the seeds and fleshy mesocarps were analyzed by GC and GC-MS. Results obtained by GC-MS analysis indicated a high variability in the oil and in the headspace from seeds and mesocarps. Sesquiterpene derivatives were the main group of volatiles in the EO from fruits and in the HS from seeds (45.0 and 64.0%, respectively), while oxygenated hydrocarbon derivatives were the main constituents in the HS obtained from fleshy mesocarps (96.5%). The different chemical composition of the headspace obtained from the seeds and mesocarps of M. argun can be correlated with the different roles that the different constituents play in the prevention of dehydration of the fruits in the desert region from where the plant was collected.
The Composition and Antimicrobial Activities of Cyperus conglomeratus, Desmos chinensis var. lawii and Cyathocalyx zeylanicus Essential Oils
Authors: Hisham Abdulkhader , Rameshkumar Koranappallil B. , Sherwani Neelam , Al-Saidi Salim , Al-Kindy Salma
Published: March 2019

The essential oil compositions of the rhizomes of Cyperus conglomeratus (Cyperaceae) collected from Oman and the leaves of two Annonaceae plants, Desmos chinensis var. lawii and Cyathocalyx zeylanicus collected from India were studied by GC, GC-MS and 13C NMR spectroscopy. Twenty-six compounds, representing 84.4% of the oil were identified in C. conglomeratus, where eugenol (31.3%), α-cyperone (10.5%) and cyperotundone (8.4%) were the major compounds. Twelve compounds, constituting 100%, were identified in D. lawii oil, of which benzyl benzoate (58.7%), β-caryophyllene (23.2%), limonene (4.9%) and α-humulene (4.0%) were the major constituents. Thirty-two compounds, comprising 98.0%, were identified in C. zeylanicus oil, of which β-caryophyllene (21.6%), α-pinene (20.4%) and E-β-ocimene (11.8%) were the major components. The antibacterial and antifungal activities of the oils were tested against a panel of five bacterial and two fungal strains. The oils showed moderate activity against all the tested microbial strains. The minimum inhibitory concentrations of the oils were also determined.
Synthesis of Taxane ABC Tricyclic Skeleton from Lycoctonine
Authors: Liang Xiao-Xia , Tang Pei , Chen Qiao-Hong , Wang Feng-Peng
Published: March 2019

A new conversional synthesis of the ABC ring system of taxoids from the C19-diterpenoid alkaloid lycoctonine was developed in 6 steps with 2% overall yield. The distinctive features of the conversion include pinacol rearrangement, enlargement of ring B, and opening of a four-membered ring.
Two Antiproliferative Saponins of Tarenna grevei from the Madagascar Dry Forest [1]
Authors: Harinantenaina Liva , Brodie Peggy J. , Callmander Martin W. , Razafitsalama L. Jérémie , Rasamison Vincent E. , Rakotobe Etienne , Kingston David G. I.
Published: March 2019

Antiproliferative bioassay-guided fractionation of the ethanol extract of the endemic Malagasy Rubiaceous plant Tarenna grevei led to the isolation of two new antiproliferative oxygenated oleanane triterpene saponins. The structures of the two active compounds were elucidated as 23-hydroxylongispinogenin 3- O-β-D-glucopyranoside (1) and longispinogenin 3- O-β-D-glucopyranosyl (1→2)-β-D-glucopyranoside (3) by analyses of their spectral data including 1D- and 2D-NMR spectroscopy and chemical evidence. Compounds 1 and 3 displayed moderate antiproliferative activity against the A2780 ovarian cancer cell line with IC50 values of 7.6 and 4 μM, respectively.
Revisit to 25R/25S Stereochemical Analysis of Spirostane-type Steroidal Sapogenins and Steroidal Saponins via 1H NMR Chemical Shift Data
Authors: Agrawal Pawan K. , Burkholz Torsten , Jacob Claus
Published: March 2019

An approach based on the difference (Δab = δa – δb) between 1H NMR chemical shifts (δa, δb) of the geminal protons of oxymethylene (H2-26) (Δab = <0.2 for 25 R; Δab = >0.5 for 25 S) is proposed for ascertaining 25 R/25 S orientation of the 27-methyl group for (22 R)-spirostane-type steroidal sapogenins and steroidal saponins. These studies suggested the 25 R-orientation of the 27-Me group for the steroidal saponins isolated by Temraz et al. from Tribulus alatus.
Structure-Cardiac Activity Relationship of C19-Diterpenoid Alkaloids
Authors: Jian Xi-Xian , Tang Pei , Liu Xiu-Xiu , Chao Ruo-Bing , Chen Qiao-Hong , She Xue-Ke , Chen Dong-Lin , Wang Feng-Peng
Published: March 2019

Thirty three C19-diterpenoid alkaloids, twenty-two prepared from known C19-diterpenoid alkaloids and eleven isolated from Aconitum and Delphinium spp. were evaluated for their cardiac activity in the isolated bullfrog heart assay. Among them, eleven compounds exhibited cardiac activity, with average rate of amplitude increase in the range of 16-118%. Compound 7, mesaconine (17), hypaconine (25), and beiwutinine (26) exhibited strong cardiac activities relative to the reference drug. The structure-activity relationship data acquired indicated that an α-hydroxyl group at C-15, a hydroxyl group at C-8, an α-methoxyl or hydroxyl group at C-1, and a secondary amine or N-methyl group in ring A are important structure features necessary for the cardiac activities of the aconitine-type C19-diterpenoid alkaloids without any ester groups. In addition, an α-hydroxyl group at C-3 is also helpful for the cardiac activity of these alkaloids.
Cytotoxic and Anti-HIV Phenanthroindolizidine Alkaloids from Cryptocarya chinensis†
Authors: Wu Tian-Shung , Su Chung-Ren , Lee Kuo-Hsiung
Published: March 2019

Bioassay-guided fractionation of the cytotoxic ethanol extract of Cryptocarya chinensis has led to the isolation of 11 compounds, including two phenanthroindolizidine alkaloids [(-)-antofine (1) and dehydroantofine (2)], five pavine alkaloids (3-7), and four proaporphine alkaloids (8-11). The structures of the isolated compounds were determined by means of NMR spectroscopic methods, and supported by HRMS and optical rotation data. Compounds 1 and 2 showed cytotoxic activity against four cancer cell lines, L1210, P388, A549, and HCT-8, with 1 being the most potent against A549 and HCT-8 with EC50 values of 0.002 and 0.001 μg/mL, respectively. In addition, 2 is first reported to exhibit significant anti-HIV activity.
Indole Alkaloids from Vinca major and V. minor Growing in Turkey
Authors: Bahadori Fatemeh , Topçu Gülaçtι , Boǧa Mehmet , Türkekul Ayla , Kolak Ufuk , Kartal Murat
Published: March 2019

A new indole alkaloid, 11-hydroxypolyneuridine, was isolated from Vinca major subsp. major L. and the known indole alkaloids vallesiachotamine and isovallesiachotamine from Vinca minor L. This is the first report on the alkaloids of both Vinca species growing in Turkey; vallesiachotamine and isovallesiachotamine were isolated from a Vinca species for the first time. V. minor may be considered as a new source for these two alkaloids due to their occurrence in high amount in the aerial parts of the plant. The alkaloid extracts of the two Vinca species were found to have high lipid peroxidation inhibitory and DPPH radical scavenging activities. Anticholinesterase activity of the extracts was also very strong.
Influence of Nutrient Medium Composition on in vitro Growth, Polyphenolic Content and Antioxidant Activity of Alchemilla mollis
Authors: Stanilova Marina , Gorgorov Rossen , Trendafilova Antoaneta , Nikolova Milena , Vitkova Antonina
Published: March 2019

Alchemilla mollis (Buser) Rothm. (Rosaceae) is a high-mountain medicinal plant growing in the Balkan Peninsula, with only one population in Bulgaria. Alchemilla plants (Lady's mantle) are commonly used in traditional medicine for treatment of many gynecological diseases. The commercial drugs “Herba Alchemillae” induce a rapid regeneration of skin epithelium and have styptic and anti-inflammatory actions. Because of the high content of phenolic compounds (tannins and flavonoids) and the ecological plasticity of the species, field cultivation or in vitro biomass production of A. mollis are possible alternatives to its collection from nature. Four MS based nutrient media differing in the concentration of the minerals and supplemented with α-naphthaleneacetic acid (NAA) and benzylaminopurine (BAP) were tested in order to examine their influence on the shoot multiplication effectiveness and the antioxidant activity of A. mollis, and also the possible relation between these parameters under the conditions of in vitro culture. The cultures grown for two months on these media differed significantly in their multiplication rates ( p<0.001), as well as in their morphological features – height, leaf color and root development. Methanol extracts of in vitro cultivated and ex vitro adapted and acclimated on Vitosha Mt. (1500 m a. s. l.) plants were analyzed for tannin and flavonoid content and for free radical scavenging activity. The contents of flavonoids and tannins in the in vitro cultures of A. mollis cultivated on the four tested media differed significantly ( p<0.05). The highest flavonoid content was found in the shoots cultivated on the control MS medium, as well as in the ex vitro adapted plants. The antioxidant activity of the in vitro cultures correlated positively with the concentrations of the PGRs in the respective media, and the ex vitro adapted plants had the highest antioxidant activity (IC50 13.1±1.9 μg/mL) commensurable with that of the commercial antioxidant butylated hydroxytoluene (BHT) used as a positive control, with an IC50 of 12.65 μg/mL.
Isolation and Characterization of New Ceramides from Aerial Parts of Lepidaploa cotoneaster
Authors: Santos Edlene O. dos , Meira Marilena , Vale Ademir E. do , David Jorge M. , de Queiróz Luciano P. , David Juceni P.
Published: March 2019

Two new ceramides were isolated from the bulbs of Lepidaploa cotoneaster (Willd. ex Spreng.) H. Rob. [ Vernonia cotoneaster (Willd. ex Spreng.) Less.)], in addition to germanicol, β-sitosterol, stigmasterol, 3-β- O-β-D-glucopyranosyl-sitosterol, lupeol, lupeoyl acetate and tiliroside. The structures of the new compounds were elucidated by spectral techniques (MS, 1H NMR, 13C NMR, HSQC, HMBC, DEPT, and TOCSY) and were compared with data reported in literature, and were established as 2 S*,2′ R*,3 S*,4 R*,11 E)- N-[2′-hydroxyhenicosanoyl]-2-amino-nonadec-11-ene-1,3,4-triol (1) and (2 S*,2′ R*,3 S*,4 R*,8 E)- N-[2′-hydroxytricosanoyl]-2-amino-nonadec-8-ene-1,3,4-triol (2). To establish the structure and to locate the double bond, the methyl ester of the fatty acid and dimethyl disulfide (DMDS) derivatives were prepared for both ceramides.
cis-Aconitic Anhydride Ethyl Ester and Phenolic Compounds from the Seeds of Alisma orientale
Authors: Zhao Ming , Chen Jing-ying , Xu Li-jia , Goedecke Tanja , Zhang Xiao-qi , Duan Jin-ao , Che Chun-tao
Published: March 2019

From the seeds of Alisma orientale, cis-aconitic anhydride ethyl ester and cis-2,4,5-trihydroxycinnamic acid were isolated, together with nine known phenolic compounds and a megastigmane sesquiterpene. All compounds are reported for the first time from Alisma species.
Trigonelline and other Betaines in Species of Laminariales
Authors: Blunden Gerald , Guiry Michael D. , Druehl Louis D. , Kogame Kazuhiro , Kawai Hiroshi
Published: March 2019

A collection of Laminariales species was made with examples in each of the presently recognized families of the order. Extracts of each species were examined for betaines, using primarily 1H NMR spectroscopy for their identification. Glycinebetaine was detected in all species tested and would appear to be a consistent feature of the Laminariales. γ-Aminobutyric acid betaine was found in all species of Laminaria examined and in three of the five Saccharina species (family Laminariaceae), but was not detected in species of either other genera of the family or in those of other Laminariales families. Trigonelline was found in some Laminaria and Saccharina species, as well as in the north Pacific species Postelsia palmaeformis ( Laminariaceae), Pseudochorda nagaii ( Pseudochordaceae) and Akkesiphycus lubricus ( Akkesiphycaceae).
Antioxidant Compounds from Algerian Convolvulus tricolor (Convolvulaceae) Seed Husks
Authors: Kacem Nassira , Hay Anne-Emmanuelle , Marston Andrew , Zellagui Amar , Rhouati Salah , Hostettmann Kurt
Published: March 2019

Seed husk extracts of Convolvulus tricolor L. (Convolvulaceae) afforded six compounds, identified for the first time from this plant: isorhamnetin 3- O-β-D-galactopyranoside (1), isorhamnetin 3- O-β-D-(6″-acetyl)-galactopyranoside (2), isorhamnetin 3- O-robinobioside (3), 3,4-di- O-caffeoylquinic acid (4), gentisic acid 5- O-glucoside (5), and scopoletin (6). Separation of compounds was carried out by CC and CPC. Structural elucidations were performed by HPLC-UV-DAD, HPLC-ESI/MS (negative mode) and NMR.
Phytopathogenic Fungal Inhibitors from Celery Seeds
Authors: Liu Tao , Liu Fu-Guang , Xie Hui-Qin , Mu Qing
Published: March 2019

Extract of celery ( Apium graveolens L.) seeds was investigated against phytopathogenic fungi. The light petroleum extract showed promising inhibition activities in the tests against Rhizoctonia solani and Fusarium oxysporum f. sp. vasinfecum. Chromatographic separation of the extract gave 19 fractions, one of which, QCZ-4, possessed significant inhibitory rates of 64.6%, 88.4% and 54.7% at a concentration of 100 ppm against R. solani, F. oxysporium f. sp. vasinfecum and Alternaria alternata, respectively. Major components in the active fraction were identified by GC-MS as p-(2-aminoethyl)phenol (39.7%), 3-(3,4-dimethybenzoyl) propionic acid (32.6%) and p-heptylphenol (26.9%).
Synthesis and Antimicrobial Activities of Some Sulphur Containing Chromene Derivatives
Authors: Şerbetçi Tuba , Birteksöz Seher , Prado Soizic , Michel Sylvie , Tillequin François
Published: March 2019

A series of 3,3-dimethyl-3 Hbenzothieno[3,2- f][1]-benzopyran analogues modified at the pyran 1,2-double bond were synthesized. The corresponding dihydro and (±)-cis-diol derivatives were converted into diacetate and cyclic carbonate upon acylation. The title compounds were characterized by spectroscopic analysis and screened for their antimicrobial activity in vitro.
Antioxidant, Antimicrobial and Wound Healing Activities of Boesenbergia rotunda
Authors: Jitvaropas Rungrat , Saenthaweesuk Suphaket , Somparn Nuntiya , Thuppia Amornnat , Sireeratawong Seewaboon , Phoolcharoen Waranyoo
Published: March 2019

The ethanolic extract of Boesenbergia rotunda (L.) Mansf. was studied for its wound-healing potential. Since wound healing is interrelated with microbial infection and reactive oxygen species (ROS), this study was conducted to evaluate the antimicrobial and antioxidant activity of B. rotunda. The antimicrobial activity of B. rotunda was studied against six bacterial and two yeast strains using disc diffusion, minimum inhibitory concentration (MIC), and minimum microbicidal concentration (MMC). The B. rotunda extract displayed potential antimicrobial and antifungal activities by inhibiting the Gram-positive bacteria Staphylococcus aureus (ATCC 25923), S. epidermidis, and Bacillus subtilis (ATCC 6633), and the yeasts Candida albicans (ATCC 10231), and Saccharomyces cerevisiae. MIC and MMC values varied from 0.04 to 25 mg/mL and from 0.16 to 25 mg/mL, respectively. The antioxidant activity of B. rotunda was evaluated by measuring the Ferric Reducing/Antioxidant Power (FRAP) and DPPH free radical scavenging activity. The FRAP and DPPH values were 22.2 μM /ug and 76.3 mg/mL, respectively. In the wound-healing studies, the topical application of the B. rotunda extract indicated a significantly increased percentage of wound contraction on day 12 compared with the control group. Histological studies showed the complete epidermis and found collagen fibers and hair follicles in the dermis. The results of the present study support the continued and expanded utilization of B. rotunda in Thai folk medicine.