bluuebunny/crossref_metadata_2025 huggingface dataset:
7-Bromo-1-ethyl-β-carboline, an Alkaloid from the New Zealand Marine Bryozoan Pterocella vesiculosa
Authors: Prinsep Michèle R. , Dumté Mérine
Published: March 2019

A new alkaloid, 7-bromo-1-ethyl-β-carboline (1) has been isolated from the New Zealand marine bryozoan Pterocella vesiculosa (Lamarck, 1816). Structural elucidation was achieved through NMR spectroscopic and mass spectrometric analysis.
Variability of the Polyphenolic Content and Antioxidant Capacity of Methanolic Extracts of Pomegranate Peel
Authors: Kam Antony , Li Kong M , Razmovski-Naumovski Valentina , Nammi Srinivas , Chan Kelvin , Li George Q
Published: March 2019

Pomegranate is a popular food due to its high polyphenolic content and antioxidant capacities. Pomegranate peel is used in traditional medicine and has greater antioxidant capacity compared with other parts of pomegranate. This study elucidated the differences in the polyphenolic content and antioxidant capacities of the methanolic extracts of pomegranate peel from different geographical localities including Australia, China and USA. The results showed that pomegranate peel from China generally had higher polyphenolic contents and antioxidant capacities than those from Australia and USA. The total contents of polyphenols and flavonoids, but not condensed tannins, were closely correlated with their total antioxidant activities. Differentiation of extracts from Chinese pomegranate peel to those extracts originating from Australia and USA were achieved by multivariate analyses based on their polyphenolic content and antioxidant capacities. The results indicate that polyphenols are useful indicators to differentiate the geographical localities of pomegranate peel and to predict their antioxidant activities. Overall, geographical localities should be taken into consideration when evaluating the polyphenolic content and antioxidant activity of pomegranate peel.
Combination Effects of Curcumin and Aqueous Extract of Lignosus rhinocerotis Mycelium on Neurite Outgrowth Stimulation Activity in PC-12 Cells
Authors: John Priscilla A. , Wong Kah - Hui , Naidu Murali , Sabaratnam Vikineswary , David Pamela
Published: March 2019

Neurotrophic factors are necessary for neuronal navigation to form viable neuronal networks. These factors are high molecular weight polypeptides that cannot cross the blood brain-barrier. Therefore, small molecules from mushrooms and plants are utilized to maintain neuronal function or up-regulate neurotrophic factors. The present study investigated whether a combination of Lignosus rhinocerotis mycelium aqueous extract and curcumin was more effective than L. rhinocerotis mycelium or curcumin alone in the stimulation of neurite outgrowth of PC-12 cells. The maximum neurite extension for L. rhinocerotis and curcumin was at 21.1% at 20 μg/mL and 29.5% at 10 μg/mL, respectively. Combining 20 μg/mL of L. rhinocerotis with one μg/mL curcumin gave 27.2% neurite extension. This combination was preferred because high concentrations of curcumin were toxic to cells. In the combination, 20 μg/mL of L. rhinocerotis enhanced neurite outgrowth activity at a lower dosage of curcumin at one μg/mL, and produced a comparable percentage of neurite outgrowth stimulation activity to L. rhinocerotis and curcumin alone in PC-12 cells.
Antimicrobial Activity of Essential Oils and Solvent Extracts from Zieria species (Rutaceae)
Authors: Sadgrove Nicholas J. , Jones Graham L.
Published: March 2019

Essential oils were hydrodistilled from six Zieria species, including two previously not investigated: Z. floydii and Z. odorifera subsp. williamsii, and characterized using GC-MS. Additionally, solvent extracts of leaf material from five of these species were prepared using n-hexane, acetone and methanol as solvents, respectively. These solvent extracts were examined, along with essential oils, for antibacterial activity using micro titer plate broth dilution assays. Antifungal activity against pathogenic Trichophyton species responsible for dermal infections such as Tinea and Kangaroo Pox (uncommon), was examined using a similar method. Results of essential oil characterizations are relatively consistent with those previously reported. Interestingly, the essential oil composition of Z. floydii showed car-3-en-2-one at a concentration of 71%, similar to that observed in a previous study for Z. furfuracea and Z. granulata, thus complementing the observations of A.G. Floyd that Z. floydii is morphologically allied with these two species (CANB 598758). Antimicrobial assays demonstrated relatively high antibacterial and antifungal activity, using both essential oils and solvent extracts. This is particularly true for the n-hexane extract from Z. smithii. We therefore conclude that Zieria species may be a useful source for the development of antiseptic, cosmaceutical and/or topical nutraceutical products. In addition, they may well serve as a source of further novel, purified compounds providing scaffolds for pharmaceutical development in the future.
Coumarin Precursor from Micromelum integerrimum Leaves
Authors: Phakhodee Wong , Pongparn Preetiya , Saovapakhiran Angkana , Laphookhieo Surat
Published: March 2019

Integerriminol (1), a coumarin precursor, was isolated from the leaves of Micromelum integerrimum along with 10 known coumarins and a flavonoid. Their structures were intensively elucidated on the basis of spectroscopic data including UV, IR, NMR, and TOF-HRMS and compared with those previously reported. A plausible biosynthetic pathway of coumarins derived from integerriminol (1) is also proposed.
Chemical Composition and Antimicrobial Activity of Daucus aureus Essential Oils from Algeria
Authors: Meliani Nawel , Dib Mohammed El Amine , Djabou Nassim , Costa Jean , Allali Hocine , Tabti Boufeldja , Muselli Alain
Published: March 2019

The volatile components of Algerian Daucus aureus Desf. were investigated using a combination of analytical techniques. Analyses of essential oils obtained by hydrodistillation from the aerial parts and roots of the plant were performed using capillary GC/RI and GC/MS analysis. Seventy-one compounds were identified, constituting 90.2–96.0% of the total essential oils,. The main components from the aerial parts of the plants were germacrene D (11.3–67.2%), followed by caryophyllene oxide (0.9–9.5%), spathulenol (0.6–8.4%), ( Z)-α-santalol (1.4–6.5%), viridiflorol (0.9–5.8%), cadin-4-en-7-ol (1.5–5.6%), and τ-cadinol (1.2–5.2%). The main components of the essential oils obtained from the roots of the plant were ( Z)-α-santalol (14.1%), caryophyllene oxide (10.6%), spathulenol (9.8%), nonadecane (6.8%), and tetradecanoic acid (5.2%). The intraspecies variations of the chemical compositions of the essential oils from the aerial parts of D. aureus from 14 Algerian sample locations were investigated using statistical analysis. Essential oil samples were clustered into two groups according to their chemical compositions. This chemical variability could be attributed to growing conditions and environmental factors. The essential oils exhibited an interesting antimicrobial effect against the microorganisms tested, with MIC values in the range of 0.125–4.6 mg/mL. It is suggested that the essential oils from D. aureus may be a new potential source of natural antimicrobial compounds that could be applied in the pharmaceutical and food industries.
Regioselective Hydroxylation and Glucosylation of α- and β-Pinenes with Cultured Cells of Eucalyptus perriniana
Authors: Shimoda Kei , Kubota Naoji , Hamada Manabu , Suwada Ken , Hamada Hatsuyuki , Hamada Hiroki
Published: March 2019

Cultured plant cells of Eucalyptus perriniana regioselectively hydroxylated (+)- and (-)-α-pinenes to the corresponding (+)- and (-)-verbenols. In addition, (+)-and (-)-verbenols were converted into mono-β-D-glucosides. On the other hand, (+)- and (-)-β-pinenes were transformed into (+)- and (-)-pinocarveol 3- O-β-D-glucosides via (+)- and (-)-pinocarveols.
Structural Factors in the Odor of α-Santalol Derivatives
Authors: Hasegawa Toshio , Izumi Hiroaki , Yamada Hideo
Published: March 2019

α-Santalol is a sesquiterpene that is a major constituent of sandalwood (Santalum album L.), and is responsible for its distinctive woody odor. We replaced the polycyclic moiety and hydroxyl group of α-santalol with other moieties, and we compared the odors of the E/Z-isomers and their saturated analogues. Our previous study of the structure-odor relationships of α-santalols bearing hydroxyl, formyl, formyloxy, and acetoxy functional groups showed there was a similarity in odor between the Z-isomer and its saturated analogue. We synthesized α-santalols with a benzyl group in place of the hydroxyl group, because many benzyl compounds have strong characteristic odors. We found similar odors for the E-isomer and its saturated analogue. In contrast, the odors of the α-santalol derivatives with a hydroxyl, formyl, formyloxy, or acetoxy group were different. We also replaced the bulky polycyclic moiety with a linear alkyl chain. The polycyclic moiety was the most important structural factor in the characteristic sandalwood odor. The synthesis of derivatives and the evaluation of their odor allowed us to identify the key structural factors in the odor of α-santalol.
Formal Synthesis of (+)-Madindoline A a Potent IL-6 Inhibitor Utilizing Enzymatic Discrimination of Quaternary Carbon
Authors: Shimizu Ken-ichi , Tomita Mina , Fuhshuku Ken-ichi , Sugai Takeshi , Shoji Mitsuru
Published: March 2019

A formal synthesis of (+)-madindoline A was achieved. The Sunazuka's key intermediate (4 R,5 S)-(–)-3-butyl-4-( tert-butyldimethylsiloxy)-5-methoxycarbonyl-2,5-dimethyl-2-cyclopentenone was synthesized from easily available (2 S,3 S)-3-acetoxy-2-ethenyl-2-methylcyclopentanone. The starting material was reliably supplied by a chemo-enzymatic procedure in enantiomerically pure form. The synthesis was performed by straightforward transformations involving enone formation and regioselective introduction of the two alkyl side chains.
Total Synthesis of Bisbibenzyl Dibenzofuran Asterelin A via Intramolecular Oxidative Coupling
Authors: Makino Kosho , Harada Kenichi , Kubo Miwa , Hioki Hideaki , Fukuyama Yoshiyasu
Published: March 2019

Total synthesis of asterelin A was accomplished by applying intramolecular Suzuki-Miyaura and oxidative couplings to the formation of an 18-membered macrocyclic ring and a dibenzofuran respectively.
Synthesis of Both Enantiomers of 12-Methyl-13-tridecanolide and 14-Methyl-15-pentadecanolide (Muscolide)
Authors: Noda Yoshihiro , Mamiya Natsuki , Kashin Hitoshi
Published: March 2019

Both enantiomers of 12-methyl-13-tridecanolide{( R)-(+)-1 ( S)-(-)-1} and 14-methyl-15-pentadecanolide (muscolide) {( R)-(+)-2 ( S)-(-)-2} were synthesized from either ( S)-(+)- or ( R)-(-)-3-bromo-2-methyl-1-propanol 8 as a chiral building block.
Synthesis of a Hydrindenone in Rings C and D of YW3699
Authors: Mizutani Reiko , Morimitsu Takahiro , Nakashima Katsuyuki , Tori Motoo
Published: March 2019

A hydrindenone in rings C and D of YW3699 was synthesized starting from (-)-isocarvone. The stereochemical requirement in this ring was successfully achieved by Eschenmoser–Claisen rearrangement followed by alkylation and the aldol reaction to afford the desired hydrindenone which can be used for further elaboration of YW3699.
Collective Total Synthesis of PPAPs: Total Synthesis of Clusianone via Intramolecular Cyclopropanation
Authors: Uwamori Masahiro , Nakada Masahisa
Published: March 2019

The total synthesis of clusianone was accomplished through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence which has been utilized for the total syntheses of nemorosone garsubellin A and hyperforin: intramolecular cyclopropanation formation of a geminal dimethyl group and regioselective ring opening of cyclopropane. Further elaboration including chemo- and stereoselective hydrogenation to generate the C7 stereogenic center and cross-metathesis to construct prenyl groups in the side-chains was employed to complete the total synthesis of clusianone.
Development of a Second Generation Palladium-Catalyzed Cycloalkenylation and its Application to Bioactive Natural Product Synthesis
Authors: Toyota Masahiro
Published: March 2019

A novel palladium-catalyzed intramolecular oxidative alkylation of unactivated olefins is described. This protocol was devised to solve one of the drawbacks of the original palladium-catalyzed cycloalkenylation that we developed. We call this new procedure the ‘second generation palladium-catalyzed cycloalkenylation’. This protocol has been applied to the total syntheses of cis-195A trans-195A boonein scholareins A C D and α-skytanthine.
Evolution of the Total Syntheses of Batzellasides the First Marine Piperidine Iminosugar
Authors: Sengoku Tetsuya , Wierzejska Jolanta , Takahashi Masaki , Yoda Hidemi
Published: March 2019

Batzellasides A-C are C-alkylated piperidine iminosugars isolated from a sponge Batzella sp. The first total synthesis of (+)-batzellaside B was achieved by employing a chiral pool approach starting from L-arabinose for the construction of a piperidine ring system. Subsequently a practical second-generation synthesis was developed by utilizing a Sharpless asymmetric dihydroxylation for the preparation of the common piperidine intermediate elaborated in the first-generation synthesis. The overall yield of batzellaside B was improved to 3.3% by introducing the exocyclic C8 stereocenter via facial selective hydride addition to a linear ketone. These syntheses allowed for the determination of the absolute stereochemistry of this natural product as well as for providing precious samples which would pave the way for further biological studies.
Triterpene Glycosides from the Sea Cucumber Eupentacta Fraudatrix. Structure and Biological Action of Cucumariosides I1, I3, I4, Three New Minor Disulfated Pentaosides
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

Three new minor triterpene glycosides, cucumariosides I1 (1), I3 (2) and I4 (3) have been isolated from the Far Eastern sea cucumber Eupentacta fraudatrix. Structures of the glycosides were elucidated by 2D NMR spectroscopy and MS. Glycosides 1–3 belong to the group of cucumariosides I, having branched pentasaccharide carbohydrate moieties with two sulfate groups and possessing 3- O-methyl-D-xylose as a terminal monosaccharide unit that is a characteristic feature of all the glycosides isolated from E. fraudatrix. Glycosides 1 and 2 differ from each other by the side chain structures in the holostane aglycone moieties, while cucumarioside I4 (3) has a 23,24,25,26,27-pentanorlanostane aglycone with an 18(16)-lactone. Cytotoxic activities of glycosides 1–3 against mouse spleen lymphocytes and ascite form of mouse Ehrlich carcinoma cells, along with hemolytic activity against mouse erythrocytes and antifungal activity were studied. Glycoside 1, having an aglycone side chain with a 24(25)-double bond, possesses moderate activity in all the tests, while glycoside 2, having 23(24)-double bond and 25-hydroxy group in the side chain, and glycoside 3 with an aglycone with an 18(16)-lactone and shortened side chain have either low activity or are non-active.
Improved Extraction and Complete Mass Spectral Characterization of Steroidal Alkaloids from Veratrum Californicum
Authors: Chandler Christopher M. , Habig Jeffrey W. , Fisher Ashley A. , Ambrose Katherine V. , Jiménez Susana T. , McDougal Owen M.
Published: March 2019

Four steroidal alkaloids extracted from the roots and rhizomes of Veratrum californicum were separated by high performance liquid chromatography (HPLC) and identified using high resolution electrospray ionization time of flight tandem mass spectrometry (ESI-TOF-MS/MS) as veratrosine, cycloposine, veratramine, and cyclopamine. This paper compares ethanol and benzene as extraction solvents, HPLC solvent conditions leading to good separation of steroidal alkaloids, and MS/MS fragmentation patterns for the four steroidal alkaloids which have been released to the public database MassBank.jp. The reported Soxhlet extraction method nearly triples the recovery of steroidal alkaloids from V. californicum.
Chiroptical Studies of Flavanone
Authors: Muñoz Marcelo A. , Bucio María A. , Joseph-Nathan Pedro
Published: March 2019

Chiral HPLC coupled to electronic circular dichroism and laser optical rotation detection (HPLC-ECD-OR) permitted the on-line chiroptical characterization of both enantiomers of racemic flavanone (1) as ECD(-)310-OR(-)670-flavanone and ECD(+)310-OR(+)670-flavanone for the first and second eluted peaks, respectively. Calculation of the ECD spectrum of one enantiomer at the TD-DFT/DGTZVP level of theory yielded the ( S)-ECD(-)310-OR(-)670 and ( R)-ECD(+)310-OR(+)670-1 absolute configuration, in agreement with the use of empirical rules for stereochemical assignment. Vibrational circular dichroism spectra of enantiopure compounds, obtained through fraction collection during repeated HPLC runs, were recorded and compared with theoretical traces produced from DFT calculations at the B3LYP/DGDZVP and B3PW91/DGDZVP levels of theory, which further confirmed the absolute configuration obtained from the on-line chiroptical data.
Orphan Flavonoids and Dihydrochalcones from Primula Exudates
Authors: Bhutia Tshering Doma , Valant-Vetschera Karin M. , Brecker Lothar
Published: March 2019

Two orphan flavonoids containing an oxepin structure in ring A and named as Primcortusin (1) and 3’-OH-Primcortusin (2) were isolated from leaf exudates of Primula cortusoides, while P. glutinosa exudates yielded two dihydrochalcone derivatives (3,4). These novel structures have not been detected in other species of Primula so far. Chemical structures were elucidated by 2D NMR and mass spectrometry. The nature of compounds 1 and 2 is discussed, and ideas about their possible origin and that of unsubstituted flavone and other irregular substituted Primula flavones are presented.
Variation in the Contents of Neochlorogenic Acid, Chlorogenic Acid and Three Quercetin Glycosides in Leaves and Fruits of Rowan (Sorbus) Species and Varieties from Collections in Lithuania
Authors: Gaivelyte Kristina , Jakstas Valdas , Razukas Almantas , Janulis Valdimaras
Published: March 2019

Our research aim was to investigate the quantitative composition of neochlorogenic acid, chlorogenic acid, rutin, hyperoside and isoquercitrin in leaves and fruit of introduced rowan plants to Lithuania using a HPLC method. In leaf and fruit samples, quantitative estimation of neochlorogenic acid (in leaf samples 1.11–11.49 mg/g, in fruit samples 0.93–5.43 mg/g), chlorogenic acid (in leaf samples 2.74–21.91 mg/g, in fruit samples 0.55–7.50 mg/g), rutin (in leaf samples 0.03–4.88 mg/g, in fruit samples 0.02-0.39 mg/g), hyperoside (in leaf samples 0.15–7.44 mg/g, in fruit samples 0.02–1.19 mg/g) and isoquercitrin (in leaf samples 0.75–5.24 mg/g, in fruit samples 0.02-0.65 mg/g) was performed. In leaf samples, the total content of identified phenolic compounds ranged from 7.18 to 35.74 mg/g. In fruit, raw material total content of neochlorogenic acid, chlorogenic acid and identified flavonoids varied from 2.24 to 11.19 mg/g. Comparison of raw material samples of Sorbus species according to their quantitative composition of identified phenolic compounds using cluster analysis singularized S. commixta leaf and fruit samples. These contained the highest contents of chlorogenic acid, hyperoside and isoquercitrin, but also the lowest contents of neochlorogenic acid and rutin. The highest contents of neochlorogenic acid were recorded for S. lancifolia leaves, and of rutin for S. anglica leaves.
A New Nervogenic Acid Glycoside with Pro-coagulant Activity from Liparis Nervosa
Authors: Song Qin , Shou Qingyao , Gou Xiaojun , Chen Fengzhen , Leng Jing , Yang Weifeng
Published: March 2019

In an effort to identify hemostatic components from Liparis nervosa (Thunb.) Lindl. using a bioactivity-guided fractionation approach, the n-BuOH extract was found to promote ADP-induced platelet aggregation and two compounds were isolated from the active extract. Compound 1 was a new nervogenic acid glycoside and the structure was elucidated as 3,5-bis(3-methyl-but-2-enyl)-4- O-[β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl]-benzoic acid by extensive spectroscopic measurements. Adenosine (2) was isolated from this plant for the first time. Compound 1 also showed good pro-coagulant activity in vitro.
Absolute Configuration of Falcarinol (9Z-heptadeca-1,9-diene-4,6-diyn-3-ol) from Pastinaca Sativa
Authors: Corell Mireia , Sheehy Emile , Evans Paul , Brunton Nigel , Valverde Juan
Published: March 2019

Falcarinol (9 Z-heptadeca-1,9-diene-4,6-diyn-3-ol; (1) is a polyacetylene commonly found in several plant families. The absolute configuration of naturally occurring 1 is not clear and contradictory results have been reported in the literature. Determination of the absolute configuration of 1 from Pastinaca sativa L. was carried out. Isolation of 95% pure 1 was performed via successive fractionation and preparative-HPLC. A racemic mixture comprised of 3 R-1 and 3 S-1 was synthesized in order to confirm the absolute configuration of the isolated natural product using chiral HPLC. Based on a combination of chiral HPLC and specific rotation, 1 present in P. sativa was found to have a 3 R absolute configuration (i.e. (3 R, 9 Z)-heptadeca-1,9-diene-4,6-diyn-3-ol).
Essential Oils of Chiliadenus Lopadusanus (Asteraceae)
Authors: Zito Pietro , Sajeva Maurizio , Scirica Elena , Bruno Maurizio , Rosselli Sergio , Maggio Antonella , Senatore Felice
Published: March 2019

The essential oils from the leaves and flowers of Chiliadenus lopadusanus growing on Lampedusa Island were obtained by hydrodistillation and analyzed by GC-MS. The major component was camphor (39.4% in the leaves and 24.0% in the flowers), followed in the leaves by torreyol (6.7%), t-cadinol (5.2%) and 1,8-cineole (3.8%), while in the flowers by t-cadinol (15.2%), t-muurolol (5.1%) and torreyol (4.5%). Among the compounds identified, several seem to play a role in antibacterial, antifungal, allelopathic and spasmolytic activity. In addition, several compounds identified in this study seem to influence the attraction of Megachile ( Eutricharaea) apicalis (Megachilidae) and Halictus ( Seladonia) gemmeus (Halictidae), two hymenopteran here identified as pollinators of Chiliadenus lopadusanus.
Leaf Oil from Vepris Madagascarica (Rutaceae), Source of (E)-Anethole
Authors: Rabehaja Delphin J. R. , Ihandriharison Harilala , Ramanoelina Panja A. R. , Ratsimamanga-Urverg Suzanne , Bighelli Ange , Casanova Joseph , Tomi Félix
Published: March 2019

The volatile components isolated from leaves of Vepris madagascarica (Baillon) H. Perier (Rutaceae), an endemic species of north-eastern, sub-humid forests of Madagascar, were investigated by GC (Retention Indices), GC-MS and 13C NMR spectroscopy. Oil samples obtained on laboratory and industrial scales exhibited similar composition, dominated by phenylpropanoids. ( E)-anethole (78.2% and 78.6%) was the major component followed by estragole (15.6% and 15.4%). In addition, trunk bark oil also contained ( E)-anethole as its major component (84.6%), as well as various sesquiterpenes in low contents.
Chemical Composition and Antioxidant Activity of the Essential Oil and Fatty Acids of the Flowers of Rhanterium Adpressum
Authors: Hamia Chahrazed , Gourine Nadhir , Boussoussa Hadjer , Saidi Mokhtar , Gaydou Emile M. , Yousfi Mohamed
Published: March 2019

The essential oil obtained by hydrodistillation of the flowers of Rhanterium adpressum Coss. & Durieu was analyzed using GC and GC-MS. The essential oil was very rich in monoterpene compounds. The major components identified were the monoterpene hydrocarbons: camphene (21.8%), myrcene (19.3%) and α-pinene (17.4%). Other compounds, including limonene, β-pinene and terpinol-4-ol, were present in low content (4–6%). The composition of the fatty acids in the lipid extract obtained from the flowers was also investigated by GC and GC-MS. The main fatty acids identified were palmitic (47.4%), oleic (12.9%) and stearic acids (10.6%). The total phenolic contents and the antioxidant activities were also evaluated for both extracts. The total phenolic contents were determined using the Folin-Ciocalteu reagent and the antioxidant activities were measured using three different assays: DPPH (1,1-diphenyl-2-picrylhydrazyl) free radical scavenging activity, FRAP (ferric reducing antioxidant potential) and a molybdenum assay. As a result of these tests, the lipid extract exhibited the highest antioxidant activities in comparison with the essential oil extract.
Chemical Composition and Biological Activity of Conyza Bonariensis Essential Oil Collected in Mérida, Venezuela
Authors: Araujo Liliana , Moujir Laila M. , Rojas Janne , Rojas Luis , Carmona Juan , Rondón María
Published: March 2019

The essential oil from aerial parts of Conyza bonariensis (L) Cronquist collected in Mérida was obtained by hydrodistillation and analysed by GC/MS. The major components were trans-β-farnesene (37.8%), trans-ocimene (20.7%) and β-sesquiphellandrene (9.8%). Cytotoxicity assay was also performed with the essential oil against HeLa (cervix carcinoma), A-459 (lung carcinoma) and MCF-7 (breast adenocarcinoma) human cell lines and against normal Vero cells (African green monkey kidney) with IC50 values ranging from 1.4 to 45.8 μg/mL. Additionally, the essential oil presented a significant bactericidal effect against Bacillus cereus, while a moderate activity was observed against Staphylococcus epidermidis and Candida albicans.
Alternate Biosynthesis of Valerenadiene and Related Sesquiterpenes
Authors: Paknikar Shashikumar K. , Kadam Shahuraj H. , Ehrlich April L. , Bates Robert B.
Published: March 2019

It is proposed that the biosynthesis of the sesquiterpene valerenadiene, a key intermediate in the biosynthesis of a sedative in valerian, involves cyclopropane and not cyclobutane intermediates and includes as a key step a cyclopropylcarbinylcation-cyclopropylcarbinylcation rearrangement analogous to the one observed in the conversion of presqualene to squalene in triterpene and steroid biosynthesis. Similar mechanisms are proposed for the biosynthesis of the related sesquiterpenes pacifigorgiol, tamariscene and (+)-pacifigorgia-1,10-diene.
A Facile Synthesis of (±)-Heliannuol-D
Authors: Zhang Tao , Huang Liang-Zhu , Li You-Qiang , Xu Yimg-Meng , Du Zhen-Ting
Published: March 2019

A facile synthesis of (±)-heliannuol-D 1, which serves as an allelopathic chemical in nature and a potential lead compound in the search for new herbicides, has been achieved in a linear 11 steps, together with its epimer. The synthesis commenced with 4-methoxy-3-methyl-acetophenone, through the Baeyer-Villiger reaction, lithiation and addition, epoxidation and intramolecular cyclization to give (±)-heliannuol-D (1) and its epimer (1a) in 32.6% overall yield. Our synthetic approach is cost-effective; this will be helpful in applying this kind of compound for the development of a new generation of agrochemicals.
Nitric Oxide and Tumor Necrosis Factor-Alpha Inhibitory Substances from the Rhizomes of Kaempferia Marginata
Authors: Kaewkroek Kanidta , Wattanapiromsakul Chatchai , Kongsaeree Palangpon , Tewtrakul Supinya
Published: March 2019

The ethanol extract of the rhizomes of Kaempferia marginata showed a potent inhibitory effect against lipopolysaccharide (LPS)-induced nitric oxide (NO) and tumor necrosis factor-alpha (TNF-α) release in RAW264.7 cells. Moreover, the partition with various organic solvents also inhibited NO production. One new pimarane-type diterpene, 1α-acetoxysandaracopimaradien-2α-ol (5), along with four known diterpenes (1–4), were isolated from the n-hexane and chloroform layers, respectively. Among these metabolites, compounds 1 and 4 were isolated for the first time from K. marginata. Compounds 1–5 showed significant inhibitory effects on NO production, with IC50 values ranging from 38.6 to 51.9 μM. Furthermore, compound 2 also exhibited significant activity against TNF-α release (IC50 = 48.3 μM). These findings may support the use of K. marginata by traditional doctors for treatment of inflammatory-related diseases.
Chemical Constituents from an Endophytic Fungus Chaetomium Globosum Z1
Authors: Zhang Chun-Yan , Ji Xiao , Gui Xuan , Huang Bao-Kang
Published: March 2019

A new ergosterol, 15β-hydroxyl-(22 E,24 R)-ergosta-3,5,8,22-tetraen-one (1), along with three known ergosterols, two known cytochalasins, and two known azapholines were isolated from Chaetomium globosum Z1. The structures of these compounds were elucidated on the basis of spectroscopic methods (HR-ESI-MS, 1D NMR, and 2D NMR). Compound 6 showed significant cytotoxic activity against A-549 and MG-63 cell lines with IC50 values of 6.96 and 1.73 μg/mL, respectively.
Chemical Constituents from the Fruit Body of Chlorophyllum Molybdites
Authors: Su Zushang , Wang Ping , Yuan Wei , Li Shiyou
Published: March 2019

A new glycoxyuracil and 15 known compounds were isolated from the fruit body of Chlorophyllum molybdites. The structures were determined from their NMR and MS data and by comparison with literature data. Compounds 2–5, 10–11, 13, and 15–16 were isolated from the genus Chlorophyllum for the first time. Compounds (1–9) did not show cytotoxicity against two human cancer cell lines, A549 and Panc-28 (GI50 > 50 μM).
Biflavonoids, Main Constituents from Garcinia Bakeriana Leaves
Authors: Al-Shagdari Ahmed , Alarcón Adonis Bello , Cuesta-Rubio Osmany , Piccinelli Anna Lisa , Rastrelli Luca
Published: March 2019

The genus Garcinia is a source of a large variety of organic compounds including biflavonoids, acylphloroglucinols and xanthones mainly, but few data are available about the chemical composition of Cuban species. The aim of this investigation was to identify the main constituents of G. bakeriana Urb., a rare Cuban endemic plant. A new biflavonoid, 4″’- O-methyl-I3,II8-biapigenin (1), together with 9 known compounds, namely, the biflavonoids amentoflavone (2), 4″’- O-methylamentoflavone (3), 4′- O-methylcupressuflavone (4), GB-2a (5), volkensiflavone (6), 6″-(2-hydroxy-3-methyl-3-butenyl)-amentoflavone (7), I3,II8-biapigenin (8), and GB-1a (9), and the xanthone norathyriol (10), were isolated from the leaves of this species. All the structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments, as well as ESIMS analysis. These results showed that the isolated biflavonoids possess a C-C interflavonoid linkage between the apigenin units or its derivatives.
Analysis of Flavonoids and Iridoids in Vitex Negundo by HPLC-PDA and Method Validation
Authors: Roy Somendu K. , Bairwa Khemraj , Grover Jagdeep , Srivastava Amit , Jachak Sanjay M.
Published: March 2019

The leaves of Vitex negundo have been reported to contain various bioactive constituents including iridoids and flavonoids. This is the first report on the simultaneous determination of iridoids and flavonoids by HPLC in three different samples of V. negundo leaves collected from three regions of India. Separation of iridoids and flavonoids was accomplished by HPLC and further elaborated for their quantification in V. negundo leaves using a C-18 column with detection at 254 and 330 nm, respectively. The developed HPLC method showed good linearity (r2≥0.999), high precision (RSD<5%) and a good recovery (99.3–103.0%) of the compounds. All the validation parameters of the developed HPLC were found to be within the permissible limits according to the ICH guidelines. The developed method was robust, accurate and reliable for the quality control of V. negundo leaves.
Anticarcinogenic Effect and Carcinogenic Potential of the Dietary Phenolic Acid: O-Coumaric Acid
Authors: Sen Alaattin , Atmaca Pelin , Terzioglu Gulsum , Arslan Sevki
Published: March 2019

Among hydroxycinnamic acids, caffeic, ferulic and p-coumaric acids have received considerable attention due to their biological activities. However, studies related to the biological activities of o-coumaric acid (OCA) are limited. In this regard, this study was designed to determine the chemopreventive potential of OCA in human breast cancer cells (MCF-7). The EC50 value of OCA was found to be 4.95 mM and was used throughout the study. Caspase-3 protein and mRNA levels increased by 59% and 72%. Similarly, protein and mRNA levels of Bax were increased by 115% and 152%. However, OCA treatment caused 48% and 35% decreases in Bcl-2 protein and mRNA levels. Cyclin D1 and cyclin dependent kinase-2 protein and mRNA levels decreased significantly. Moreover, p53 protein and mRNA levels increased by 178% and 245%, respectively. In addition to p53, PTEN protein and mRNA levels were induced. Although, CYP1A1, CYP1A2 and CY2E1 mRNA levels increased, CYP3A4 and CYP2C9 mRNA levels decreased in response to OCA treatment. These results suggest that OCA demonstrates anticarcinogenic activity on MCF-7 cells by activating multiple pathways. However, it also has high carcinogen activating and drug interaction potential. Therefore, serious precautions must be taken before using OCA.
Cancer-Suppressive Potential of Extracts of Endemic Plant Helichrysum Zivojinii: Effects on Cell Migration, Invasion and Angiogenesis
Authors: Matić Ivana Z. , Aljančić Ivana , Vajs Vlatka , Jadranin Milka , Gligorijević Nevenka , Milosavljević Slobodan , Juranić Zorica D.
Published: March 2019

Helichrysum zivojinii Černjavski & Soška is an endemic plant species that grows in the National Park Galičica in Macedonia. Five extracts were isolated as fractions from the aerial parts of the plant: a n-hexane extract (1), a dichloromethane extract (2), an ethyl-acetate extract (3), a n-butanol extract (4) and a methanol extract (5). A dose-dependent cytotoxic activity of the extracts on MDA-MB-231 and EA.hy926 cells was observed. Extracts exhibited more pronounced cytotoxic actions on MDA-MB-231 cells than on EA.hy926 cells. The n-hexane extract (1), at a non-toxic concentration, exhibited an inhibitory effect on the migration as well the invasiveness of MDA-MB-231 cells. The dichloromethane extract (2), at a non-toxic concentration, demonstrated inhibition of MDA-MB-231 cells invasion. Each of the five extracts applied at non-toxic concentrations inhibited migration of EA.hy926 cells. The prominent inhibitory effect of the n-hexane extract on EA.hy926 cells migration was associated with a notable anti-angiogenic action of this extract. The other four tested extracts demonstrated mild anti-angiogenic activity. Our data highlight the prominent anticancer potential of n-hexane (1) and dichloromethane (2) extracts, which could be attributed to their very pronounced and selective cytotoxic activities as well as their anti-invasive and anti-angiogenic properties.
Analysis of Volatile Components, Fatty Acids, and Phytosterols of Abies Koreana growing in Poland
Authors: Wajs-Bonikowska Anna , Olejnik Karol , Bonikowski Radosław , Banaszczak Piotr
Published: March 2019

Extracts and essential oils from seeds as well as essential oils from cone scales and needles with twigs of the Abies koreana population were studied. An analysis of Korean fir essential oils allowed us to determine 147 volatile compounds. The identified compounds constituted 97–99% of the seed, cone and needle oils. The main volatile in the seed and needle oils was limonene (56.6% and 23.4%, respectively), while the predominant volatile in cone oils was α-pinene (51.2%). Korean fir seeds provided a rich source of both essential oil (3.8–8.5%) and extract, which was isolated with a 24.5% yield and contained numerous groups of fatty acids and phytosterols (414 μg/100g extract). The most prominent fatty acids were unsaturated, among which linoleic (41.2%) and oleic (31.2%) fatty acid were the main ones while the dominant sterols were isomers of ergostadienol and β-sitosterol. A. koreana seeds, cones and needles are a source of many volatile bioactive compounds while the seed extract, with a pleasant scent, contained not only volatiles, but also fractions rich in fatty acids and phytosterols. These facts make A. koreana essential oils and especially the seed extract potential components of cosmetics.
GC/GC-MS Analysis, Isolation and Identification of Bioactive Essential Oil Components from the Bhutanese Medicinal Plant, Pleurospermum Amabile
Authors: Wangchuk Phurpa , Keller Paul A. , Pyne Stephen G. , Taweechotipatr Malai , Kamchonwongpaisan Sumalee
Published: March 2019

We have hydrodistilled the essential oil (EO) from the aerial parts of the Bhutanese medicinal plant, Pleurospermum amabile using a Clevenger apparatus and evaluated this EO by GC/GC-MS and NMR analysis followed by testing for bioactivity. The GC-MS analysis identified 52 compounds with ( E)-isomyristicin as a major component (32.2%). Repeated purification yielded four compounds; ( E)-isomyristicin (1), ( E)-isoapiol (2), methyl eugenol (3) and ( E)-isoelemicin (4). Compound 2 and the mother EO showed the best antiplasmodial activity against the Plasmodium falciparum strains, TM4/8.2 (chloroquine and antifolate sensitive) and K1CB1 (multidrug resistant). They exhibited mild antibacterial activity against Bacillus subtilis. None of the test samples showed cytotoxicity.
Chemical Composition and Synergistic Antioxidant Activities of Essential Oils from Atractylodes Macrocephala and Astragalus Membranaceus
Authors: Li Jinkui , Li Feng , Xu Yan , Yang Wenjian , Qu Lili , Xiang Qian , Liu Cong , Li Dapeng
Published: March 2019

Chemical composition of the essential oils derived from Atractylodes macrocephala (AMA), Astragalus membranaceus (AME) and AMA-AME herb pair was investigated using gas chromatography-mass spectrometry (GC-MS). Antioxidant activities were evaluated by 1,1-diphenyl-2-picyrlhydrazyl (DPPH) radical-scavenging and Trolox equivalent antioxidant capacity (TEAC) assays. Forty-five, ten and forty-three components were identified in AMA, AME and AMA-AME essential oils, respectively. AMA-AME essential oil exhibited a significantly higher radical scavenging capacity than the theoretical sum of those of the respective herb essential oils ( P < 0.05). Principal component analysis showed that twenty-three components contributed to the scavenging activities against DPPH and ABTS•+ radicals. Moreover, the concentrations of these major components exhibited various increases to some extent when compared with the theoretical sum of the respective herb essential oils. These findings suggest that combination of two or more herbs might be used as a promising source of natural antioxidants in the pharmaceutical and food industries.
Meeting Report: First National Meeting on Aloe, April 20–21, 2013, Isernia, Italy New Perspectives in Aloe Research: From Basic Science to Clinical Application
Authors: Capasso Raffaele , Laudato Massimiliano , Borrelli Francesca
Published: March 2019

Aloe preparations have maintaining their popularity over the of course time. Aloe latex is used for its laxative effects; aloe gel is used topically for skin ailments and internally for variety of disturbances; aloe extract is potentially useful for cancer.
Major Constituents of Boswellia Carteri Resin Exhibit Cyclooxygenase Enzyme Inhibition and Antiproliferative Activity
Authors: Ali Sami I. , Zhang Chuan-Rui , Mohamed Amal A. , EL-Baz Farouk K. , Hegazy Ahmad K. , Kord Maimona A. , Nair Muraleedharan G.
Published: March 2019

Aromatic gum from Boswellia carteri (olibanum oleogum) has long been used in Egyptian traditional medicine. Cyclooxygenase-1 (COX-1) enzyme inhibitory assay guided purification of the extracts of this resin resulted in five bioactive compounds, 3α- O-acetyl-8,24-dien-tirucallic acid (1), verticilla-4(20),7,11-triene (2), cembrene A (3), incensole acetate (4), and incensole (5). The pure isolates were investigated for their inhibitory effects on COX-1 and −2 enzymes and human tumor cell lines Hep-G2, MCF-7 and RAW 264.7. Compounds 1–5 inhibited COX-2 enzyme by 39.0, 32.7, 60.0, 46.3, and 49.8%, respectively. Furthermore, compound 2 showed an inhibitory concentration of 50% (IC50) at 9 μg/mL against Hep-G2 tumor cell line. This is the first report of COX-1 and -2 enzyme and tumor cell proliferation inhibitory effects of compounds 1 and 2.
Cucurbitane-type Triterpenes from Citrullus Lanatus (Watermelon) Seeds
Authors: Kikuchi Takashi , Okada Rina , Harada Yu , Ikushima Kenji , Yamakawa Takahiro , Yamada Takeshi , Tanaka Reiko
Published: March 2019

Two new cucurbitane-type triterpenes, 24-hydroperoxycucurbita-5,25-dien-3β-ol (1) and 25-hydroperoxycucurbita-5,23-dien-3β-ol (2), were isolated from a MeOH extract of Citrullus lanatus seeds. Compounds 1 and 2 exhibited moderate cytotoxic activities with IC50 values of 33.4–52.4 μM against HL-60 (human leukemia), P388 (murine leukemia), and L1210 (murine leukemia) cells. Compound 1 showed melanogenesis inhibitory activity (melanin content 80.0 %) with low cytotoxicity (cell viability 97.6 %) at a low concentration (10 μM).
Monanchomycalin C, a New Pentacyclic Guanidine Alkaloid from the Far-Eastern Marine Sponge Monanchora Pulchra
Authors: Tabakmakher Ksenya M. , Denisenko Vladimir A. , Guzii Alla G. , Dmitrenok Pavel S. , Dyshlovoy Sergey A. , Lee Hyi-Seung , Makarieva Tatyana N.
Published: March 2019

A new pentacyclic guanidine alkaloid, monanchomycalin C (1), along with the earlier known ptilomycalin A (2), were isolated from the Far-Eastern marine sponge Monanchora pulchra. The structure of 1 was elucidated using 1D and 2D NMR spectroscopic and mass spectrometric data. Compounds 1 and 2 exhibited cytotoxic activities against human breast cancer MDA-MB-231 cells with IC50 values of 8.2 μM and 4.3 μM, respectively.
Antiinflammatory and Antioxidant Flavonoids from Helichrysum Kraussii and H. odoratissimum Flowers
Authors: Legoale Percival B. , Mashimbye Mahlori J. , van Ree Teunis
Published: March 2019

Organic extracts of the flowers of Helichrysum kraussii and H. odoratissimum contain several bioactive flavonoids, characterized by 1H NMR, 13C NMR and mass spectrometry. Four flavonoids, 5,6-dihydroxy-3,7,8-trimethoxyflavone, 5,7-dihydroxy-3-methoxyflavone, 3′,4′,5,7-tetrahydroxy-3-methoxyflavone and 3′,4′,3,5-tetrahydroxy-7-methoxyflavone, have antioxidant activity by the DPPH free radical assay, while 5,6-dihydroxy-3,7,8-trimethoxyflavone and 3′,4′,3,5-tetrahydroxy-7-methoxyflavone have promising anti-inflammatory activity.
Polyphenolic Compounds from Callus Cultures of Iris Pseudacorus
Authors: Tarbeeva Darya V. , Fedoreyev Sergey A. , Veselova Marina V. , Kalinovskiy Anatoliy I. , Seletskaya Ludmila D. , Mazurok Tamara I. , Bulgakov Victor P.
Published: March 2019

A callus culture of Iris pseudacorus L. (Iridaceae) was established from plant leaves using a modified Murashige and Skoog medium. A derivative of cinnamic acid (lavandoside) (1), a neolignan (dehydrodiconiferyl alcohol-4- O-β-D-glucopyranoside) (2) as well as three isoflavonoids, tectoridin (3), tectorigenin (4), and iristectorigenin A (5) were isolated from the callus culture. Under normal conditions, the calli accumulated 0.4% DW of polyphenols. The addition of phenylalanine to a concentration of 1 mM resulted in a 1.5-fold increase in isoflavonoid production, allowing the accumulation of 0.69% of polyphenols in the callus dry weight. Tectorigenin, a promising chemotherapeutic and chemopreventive agent for the treatment of carcinomas, was produced in I. pseudacorus calli in high quantities (0.3% DW).
Pterocarpans from the Root Bark of Aeschynomene Fascicularis
Authors: Caamal-Fuentes Edgar , Moo-Puc Rosa , Torres-Tapia Luis W. , Peraza-Sanchez Sergio R.
Published: March 2019

A new pterocarpan, aeschynocarpin (1), and the known pterocarpan 2-methoxymedicarpin (2) were isolated for the first time from Aeschynomene fascicularis (Fabaceae) and their structures elucidated by means of spectroscopic {UV/Vis, IR, and NMR (1H, 13C, COSY, HMQC, and HMBC)} and mass spectrometric (EI-MS and HRCIMS) techniques. Both compounds were tested in vitro for their cytotoxic and antiproliferative activities against a panel of cancer cell lines. This is the first report on the presence of pterocarpans in the genus Aeschynomene.
(+)-Rumphiin and Polyalthurea, New Compounds from the Stems of Polyalthia Rumphii
Authors: Wang Tian-Shan , Luo You-Ping , Wang Jing , He Meng-Xiong , Zhong Ming-Guo , Li Ying , Song Xiao-Ping
Published: March 2019

Two new compounds, (+)-rumphiin (3) and polyalthurea (7), together with seven known ones, 3,4,5-trimethoxy benzoic acid (1), (-)-seselinone (2), cannabisin D (4), allantoin (5), oxostephanine (6) and a mixture of β-sitosterol (8) and stigmasterol (9) were isolated from the stems of Polyalthia rumphii. The chemical structures of 3 and 7 were elucidated by the combination of spectroscopic data, and the absolute configuration of 3 at C-2 was determined by the matrix method to be R. All compounds were evaluated for their cytotoxicity on four human cancer cell lines, which demonstrated that 3 was a moderate bioactive lignan, and 6 showed significant anticancer activity against SPC-A-1 and BEL-7402 cell lines with IC50 values of 1.47 and 1.73 μg/mL, respectively.
Potent Microbial and Tyrosinase Inhibitors from Stem Bark of Bauhinia Rufescens (Fabaceae)
Authors: Muhammad Aminu , Sirat Hasnah Mohd
Published: March 2019

The stem bark extracts of Bauhinia rufescens Lam. (Fabaceae) yielded 6-methoxy-7-methyl-8-hydroxydibenz[ b,f]oxepin, α-amyrin acetate, β-sitosterol 3- O-β-D-xylopyranoside, 4-(2′-Hydroxyphenethyl)-5-methoxy-2-methylphenol, menisdaurin and sequoyitol. Their structures were determined using spectroscopic methods and comparisons with the literature data. For the antimicrobial assay Gram-positive and Gram-negative bacterial and fungal strains were tested, while the tyrosinase inhibition assay utilized L-DOPA as a substrate for the tyrosinase enzyme. 6-Methoxy-7-methyl-8-hydroxydibenz[ b,f]oxepin, α-amyrin acetate, β-sitosterol 3- O-β-D-xylopyranoside, menisdaurin and sequoyitol showed weak to moderate activities with minimum inhibition concentration (MIC) values in the range of 112.5–900 μg/mL against all bacterial strains, while the MIC values for the fungal strains were in the range of 28.1–450 μg/mL. In the tyrosinase inhibition assay, α-amyrin acetate was found to be moderately active against tyrosinase with an inhibition of 62% at 0.1 mg/mL. This activity was lower than that of the positive control, kojic acid (85%).
An Alkenylresorcinol Derivative from Hakea Sericea Fruits and their Antimicrobial Activity
Authors: Luís Ângelo , Cruz Carla , Duarte Ana Paula , Domingues Fernanda
Published: March 2019

Hakea sericea has been introduced to Portugal for ornamental purposes. The phytochemical composition and the antioxidant, antibacterial, antibiofilm and cytotoxic properties of this shrub species have been previously reported. The present work describes the bioassay-guided fractionation of the crude methanolic extract of H. sericea fruits and the isolation of 9-(3,5-dihydroxy-4-methylphenyl)nona-3( Z)-enoic acid. The structure of this new compound was established by one- and two-dimensional NMR and IR spectroscopy, and high-resolution mass spectrometry. The antibacterial properties of the new alkenylresorcinol were studied by determining its MIC values against several strains of Gram-positive and Gram-negative bacteria using the resazurin microtiter assay. The new alkenylresorcinol inhibited the growth of Enterococcus faecalis, Listeria monocytogenes and Bacillus cereus with MIC values of 0.31, 0.02 and 0.16 mg/mL, respectively. Good MIC values were obtained against Staphylococcus aureus strains (0.005 – 0.16 mg/mL), including the clinical isolates (SA 01/10, SA 02/10 and SA 03/10) and MRSA strains.