bluuebunny/crossref_metadata_2025 huggingface dataset:
Fatty Acids Composition of Two Holothuroidea Species – Cucumaria japonica and C. okhotensis
Authors: Rybin Viatcheslav , Pavel Konstantin , Boltenkov Eugene , Karlina Anastasiya , Timchishina Galina , Moiseenko Olga
Published: March 2019

The fatty acid compositions of the lipids of two holothurian species ( Cucumaria japonica and C. okhotensis) were investigated. High contents of 12-methyltetradecanoic acid and eicosapentaenoic acid (up to 17.7 % and 28.4% of total fatty acids, respectively) in the lipids of both species were revealed. Species specific differences in the content of 23:1 n-9 fatty acid in the lipids from viscera and body wall were found. In C. japonica, the viscera to body wall ratio was 0.07, while in C. okhotensis this ratio was 0.28. The fatty acid compositions of the lipids from both investigated holothurian species permit their use for the manufacturing of foodstuff, as well as for biologically active additives.
Chemical Composition and Antimicrobial Studies of the Essential Oils of Jatropha integerrima Jacq (Leaf and Seeds)
Authors: Eshilokun Adeolu O. , Kasali Adeleke A. , Ogunwande Isiaka A. , Walker Tameka M. , Setzer Williams N.
Published: March 2019

The chemical composition of the essential oils of the leaves and seeds of Jatropha integerrima was investigated by GC and GC-MS. The results showed significant variation in the chemical constituents of the tissue/parts analyzed. The leaf has pentadecanal (32.4%), 1,8-cineole (11.2%) and β-ionone (10.8%) as the major components. On the other hand, the seed oil is comprised mainly of aliphatic hydrocarbons represented by pentacosane (13.6%), hexacosane (13.3%), octacosane (12.3%) and heptacosane (10.1%). However, the defatted seed oil was predominantly made up of the monoterpenes 1,8-cineole (35.5%), p-cymene (20.5%) and α-pinene (16.5%). The oils displayed weak antimicrobial activity against Bacillus cereus and Staphylococcus aureus.
Reniformin, a Unique Diterpene Ester from the Roots of Pelargonium reniforme
Authors: Lattè Klaus Peter , Kaloga Maki , Kolodziej Herbert
Published: March 2019

The natural occurrence of the first diterpene in the roots of Pelargonium reniforme (Geraniaceae) is demonstrated. The unique metabolite, reniformin, represents an ester in which a novel diterpene acid with an uncommon -CH2-CH2-bridging element is linked to 2-(4-hydroxyphenyl)ethansulfonic acid. The latter entity has also hitherto not been encountered as a component in natural products. The structure of reniformin was established on the basis of spectroscopic methods.
An in-vivo Study of the Immunomodulatory Activity of Coumarinolignoids from Cleome viscosa
Authors: Bawankule Dyaneshwar U. , Chattopadhyay Sunil K. , Pal Anirban , Saxena Kopal , Yadav Sachidanand , Yadav Narayan P. , Mani Dayanandan , Tripathi Arun K. , Beg Salim U. , Srivastava Amit , Gupta Anil K. , Khanuja Suman Preet S
Published: March 2019

Cleome viscosa (Capparidaceae) is used in fever, inflammation and liver diseases. Systematic investigation of the seeds of this species has resulted in the isolation of three coumarinolignoids, cleomiscosin A, B and C. The present study was undertaken to determine the immunomodulatory activity of these coumarinolignoids using inbred female Swiss albino mice as an in-vivo study. Experimental animals were divided into six groups, each comprised of six mice. These received oral treatment for a period of 28 days. Body weight variation, and hematological, humoral and cell mediated immune response related parameters were studied in which coumarinolignoids at a dose of 10 mg/kg body weight enhanced the body immune function by significantly increasing the white blood cell count, hemagglutination antibody titer responses, and reducing delayed type hypersensitivity response towards rabbit red blood cells.
Chemical Composition and Antibacterial Activity of Cupressus dupreziana A. Camus
Authors: Ramdani Messaoud , Rached Oualida , Laouer Hocine , El Koli Meriem , Lograda Takia
Published: March 2019

The essential oils obtained by hydrodistillation from the green branchlets of Cupressus dupreziana A. Camus growing wild in Tassili n'Ajjer (Algeria) were analyzed by GC and GC/MS. The main constituents of the essential oils were α-pinene (27.2% - 44.2%), germacrene D (16.2% - 27.2%) and Δ3-carene (14.2% - 26.7%). The oils showed insignificant activity on the growth of Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853) and Staphylococcus aureus (ATCC 25923), when investigated by the diffusion method.
Bioactive Flavone Sulfates of Abutilon indicum Leaves
Authors: Matławska Irena , Sikorska Maria , El-Sayed Nabil H. , Budzianowski Jaromir , Hołderna-Kędzia Elżbieta , Mabry Tom J.
Published: March 2019

Two flavones, hypolaetin 8- O-β-glucuronopyranoside 3″- O-sulfate and isoscutellarein 8- O-β-glucuronopyranoside 3″-O-sulfate, together with hypolaetin 8- O-β-glucuronopyranoside, kaempferol 3- O-α-rhamnopyranosyl (1“→6′”)-β-glucopyranoside and quercetin 3- O-α-rhamnopyranosyl (1″→6″”)-β-glucopyranoside were isolated from the leaves of Abutilon indicum, and their structures elucidated by acid hydrolysis and spectroscopic methods, including HPLC/ESI-MS, and 1H, 13C NMR, COSY, HMQC, HSQC and HMBC spectroscopic experiments. The antimicrobial activity of hypolaetin 8- O-β-glucuronopyranoside 3″- O-sulfate and of isoscutellarein 8- O-β-glucuronopyranoside 3″- O-sulfate against Staphylococcus aureus was confirmed.
Black Cohosh and Climacteric Symptoms: Growing Knowledge about the Efficacy and Safety
Authors: Bilia Anna Rita , Eterno Federico , Vincieri Franco Francesco
Published: March 2019

Hormone therapy of perimenopausal and postmenopausal disorders includes, in many cases, treatment with estrogens but many recent studies have raised the question as to whether it brings more dangers than benefits for patients. This has led to an increased use of alternatives, mainly plant derived extracts. Among the botanical supplements and herbal medicinal products, extracts of the rhizome and roots of black cohosh are used worldwide for these purposes. This plant has a long-standing history of being used to treat climateric complaints and its clinical efficacy has been proven in several double-blind placebo controlled studies. In terms of safety, minor and transient adverse effects such as nausea, vomiting, headaches and dizzness have been observed in clinical trials. A few cases of hepatotoxicity have been reported, but a direct association with the use of black cohosh has not been demonstrated. Black cohosh was first thought to be estrogenic in nature, but recent studies have proposed it as selective estrogen receptor modulator (SERM) and serotoninergic, dopaminergic and cholinergic mechanisms have been described. Black cohosh shows great promise for relief of menopausal symptoms, primarly of vasomotor and possibly mood symptoms, with an overall positive safety profile of at least 6 months and likely longer. However, data from longer and in some cases more rigorous clinical trials are necessary to assess high efficacy and to substantiate safety.
Bio-Assay Guided Isolation of Germacranes with Anti-Protozoan Activity from Magnolia sororum
Authors: Sánchez Luis A. , Capitan Zeuz , Romero Luz I. , Ortega-Barría Eduardo , Gerwick William H. , Cubilla-Rios Luis
Published: March 2019

In the course of our search for antiprotozoal agents from terrestrial plants, three new germacranes 1, 2 and 3, together with the well known sesquiterpene lactones parthenolide (4) and costunolide (5), were isolated from Magnolia sororum using bioassay-guided fractionation methods. The structures of these new compounds were elucidated by 1D and 2D NMR spectroscopic analysis. Compound 5 exhibited activity (IC50 = 9.4 μM) in vitro against the Leishmania mexicana parasite. Additionally, all compounds were also evaluated against Trypanosoma cruzi and Monkey Vero cells without showing much activity.
A New Cytotoxic Sesquiterpene and Three Anti-inflammatory Flavonoids from Egyptian Tanacetum Santolinoides
Authors: Ibrahim Sabrin R. M. , Badr Jihan M. , Sayed Khalid A. El , Youssef Diaa T. A.
Published: March 2019

A re-investigation of the methanolic extract of the aerial parts of Tanacetum santolinoides has resulted in the isolation of a new sesquiterpene, tanacetonic acid (1), along with three known methoxylated flavonoids. The structure of the isolated compounds was secured based on their IR, UV, 1D and 2D (1H-1H COSY, HSQC and HMBC) NMR spectroscopic and FAB mass spectral characteristics. The new sesquiterpene showed a significant cytotoxic activity when tested using the brine shrimp bioassay, while the three flavonoids demonstrated anti-inflammatory effects in the rat paw oedema test.
New Prenylated Dihydrostilbenes from Croton Laevifolius
Authors: Ahmat Norizan , Said Ikram M. , Latip Jalifah , Din Laily B. , Syah Yana M. , Hakim Euis H.
Published: March 2019

Two prenylated dihydrostilbenes have been isolated from the methanol extract of the flower of Croton laevifolius. The structures of these compounds were assigned as 3,5,3′,4′-tetrahydroxy-2,6,2′-tris(3-methylbut-2-enyl)dihydrostilbene (laevifolin A) and 3,5,3′,4′-tetrahydroxy-2,6,5′-tris(3-methylbut-2-enyl)dihydrostilbene (laevifolin B) based on spectroscopic evidence, including UV, IR, 1D and 2D NMR, and mass spectra. The chemotaxonomic significance of the presence of these dihydrostilbene derivatives is briefly discussed.
Chemical Composition and Antibacterial Activity of Pituranthos Chloranthus Volatile Oil
Authors: Dahia Mostepha , Laouer Hocine , Chaker Adel N. , Prado Soizic , Meierhenrich Uwe J. , Baldovini Nicolas
Published: March 2019

The chemical composition of the essential oil of Pituranthos chloranthus ssp. cossonianus Maire (Apiaceae) was investigated by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) to reveal 54 compounds. The main constituents were myristicine (27.4%), limonene (15.8%), α-pinene (11.4%), and α-phellandrene (8.3%). The antibacterial activity of the oil was evaluated against several strains and was shown to be significant against Pseudomonas aeruginosa.
Cruzain Inhibitory Activity of the Leaf Essential Oil from an Undescribed Species of Eugenia from Monteverde, Costa Rica
Authors: Stokes Sean L. , Cole Ramona A. , Rangelova Mariana P. , Haber William A. , Setzer William N.
Published: March 2019

The leaf essential oil of Eugenia sp. nov. “San Bosco” inhibits cruzain, a cysteine protease from Trypanosoma cruzi, the parasitic protozoan responsible for Chagas disease, with an IC50 of 36.4 μg/mL. Eugenia “San Bosco” leaf oil is dominated by the sesquiterpene hydrocarbons zingiberene (24.7%) and germacrene D (11.1%), and these two compounds (IC50 = 8.6 and 21.2 μg/mL, respectively) are likely responsible for the cruzain inhibitory activity observed in the essential oil.
Biological Activities of Essential Oils from Monteverde, Costa Rica
Authors: Werka Jennifer Schmidt , Boehme Amelia K. , Setzer William N.
Published: March 2019

Essential oils from Calyptranthes pittieri (Lauraceae), Cinnamomum tonduzii (Lauraceae), Croton niveus and C. monteverdensis (Euphorbiaceae), Dendropanax arboreus (Araliaceae), Eugenia austin-smithii and E. haberi (Myrtaceae), Myrcianthes fragrans and M. rhopaloides (Myrtaceae), Nectandra membranacea (Lauraceae), Ocotea floribunda (Lauraceae), Oreopanax xalapensis (Araliaceae), Piper umbellatum (Piperaceae), Psidium guajava (Myrtaceae), Stauranthus perforatus (Rutaceae), Zanthoxylum acuminatum, Z. melanostictum, Z. monophyllum, and Zanthoxylum sp. nov. “brillante” (Rutaceae), have been screened for cytotoxic activity against a panel of human tumor cell lines, antibacterial activity against Gram-positive and Gram-negative bacteria, as well as brine shrimp (Artemia salina) lethality.
Composition and Antibacterial Screening of the Essential Oils of Leaves and Roots of Espeletiopsis Angustifolia Cuatrec
Authors: Meccia Gina , Rojas Luis B. , Velasco Judith , Díaz Tulia , Usubillaga Alfredo
Published: March 2019

Hydrodistillation of leaves and roots of Espeletiopsis angustifolia Cuatrec. (Asteraceae) yielded 0.18% and 0.15% essential oils, respectively. GC-MS analysis allowed identification of 24 components, which made up 92.9% of the total oil from the leaves, while only 16 compounds (67.2%) were identified in the roots. The most abundant compounds in the leaves were α-pinene (29.9%), β-caryophyllene (14.1%), α-gurjunene (9.9%), β-pinene (9.6%), and 19-oxo-ent-kaur-16-ene (5.3%). In the roots, the main ones were α-pinene (27.9%), β-pinene (10.9%), β-caryophyllene (10.2%), and bicyclogermacrene (8.6%). Antibacterial activity was tested against Gram-positive and Gram-negative bacteria using the agar diffusion method. Activity was observed only against Gram-positive bacteria. MIC values were determined for Staphyloccocus aureus ATCC 25923 (1000 μg/mL, both roots and leaves) and Enteroccocus faecalis ATCC 29212 (240 μg/mL, roots and 360 μg/ mL, leaves).
GC-MS Analysis of the Leaf Essential Oil of Ipomea Pes-caprae, a Traditional Herbal Medicine in Mauritius
Authors: Marie Daniel E.P. , Dejan Brkic , Quetin-Leclercq Joëlle
Published: March 2019

The chemical compositions of the essential oils of the fresh and dried leaves of Ipomea pes-caprae from Mauritius were studied for the first time by gas chromatography-mass spectrometry and 70 compounds were identified. The major components were found to be 8-cedren-13-ol (13.0%), (E)-nerolidol (7.0%), guaiol (6.2%), α-cadinol (6.2%) and limonene (6.1%) in fresh leaves and β-caryophyllene (36.6%), α-copaene (8.0%), germacrene D (7.3%), phytol (5.8%), δ-cadinene (5.7%), and α-humulene (5.4%) in the dried leaf samples. The relationship between the anti-hemorrhoidal activity of Ipomea pes-caprae, one of its traditional uses in Mauritius, and the chemical composition of the essential oil samples is also discussed.
Chemical Composition, Antiradical and Antifungal Activities of Essential Oil of the Leaves of Cinnamomum Zeylanicum Blume from Cameroon
Authors: Dongmo Pierre M. Jazet , Tatsadjieu Léopold N. , Tchoumbougnang François , Sameza Modeste L. , Dongmo Bernadin Ndongson , Zollo Paul H. Amvam , Menut Chantal
Published: March 2019

The aim of the present study was to investigate the essential oil of Cinnamomum zeylanicum from Cameroon for its chemical composition, antiradical and antifungal activities against some common fungi causing spoilage of stored food product. The essential oil, obtained by hydrodistillation of fresh leaves, was analysed by GC and GC/MS. The oil contains 11 components among which eugenol (89.1%), linalool (4.3%), benzoate benzyl (3.1%) and cinnamaldehyde (1.5%) were the main components. Determination of antiradical activity of the oil was studied by the DPPH (diphenyl picryl hydrazyl) method. The antiradical activity of Cinnamomum essential oil (SC50 = 4.5 mg/L) was higher than that of butylated hydroxy toluene (BHT), which was used as the reference compound (SC50 = 7 mg/L). The growth inhibitory effect of C. zeylanicumn essential oil on Aspergillus flavus and Fusarium moniliforme was determined on potato dextrose agar. After 9 days of incubation on essential oil-supplemented medium, the growth of A. flavus and Fusarium was totally inhibited by 500 ppm of Cinnamommum zeylanicum oil. Results obtained in the present study indicate the possibility of exploiting C. zeylanicum essential oil to prevent diseases such as diabetes and cancer, to slow down ageing, and also to combat strains of A. flavus and Fusarium moniliforme responsible for biodeterioration of stored food products.
Biological Activities of Selected Essential Oils
Authors: Williams Lawrence A. D. , Porter Roy B. , Junor Grace O.
Published: March 2019

The manuscript reviews the broad spectrum of biological activities associated with essential oils. From the analyses of the data it is evident that essential oils could have tremendous application in the therapeutic, food, agrochemical and poultry industries.
The Biology of Essential Oils in the Pollination of Flowers
Authors: Cseke Leland J. , Kaufman Peter B. , Kirakosyan Ara
Published: March 2019

Pollination is an essential biological process in higher plant reproduction that involves the transfer of pollen to the female sexual organs of flowers or cones. It plays a critical role in the reproductive success and evolution of most plant species by allowing plants to share genetic material from other members of the same or closely-related species, thus increasing genetic diversity. In many cases, non-plant organisms are involved in carrying out this cross-pollination, including insects, bats, mammals, and birds. In order to attract such pollinators, plants have evolved the ability to produce a mind-boggling array of volatile compounds that have also found abundant use for humans when collected as essential oils. In this review, we focus on the role of essential oil compounds that are produced by flowers as chemical attractants used to draw in their often highly-specific pollinators. We examine in some detail various questions behind the biology of floral scent, including how these compounds are produced in flowers, how they are detected by potential pollinators, and how biotechnology can be used to alter their activity.
A Novel Sesquiterpene from Pulicaria Crispa (Forssk.) Oliv
Authors: Stavri Michael , Mathew Koyippally T. , Gibbons Simon
Published: March 2019

Using 1- and 2-dimensional NMR experiments and high-resolution mass spectrometry, a novel sesquiterpene, possessing a new skeleton, has been characterized from the n-hexane extract of the aerial parts of Pulicaria crispa (Asteraceae) as rel-2α,6α-dimethyltetracyclo-decal-3-en-2,12-diol-8α,13-olide and given the trivial name pulicrispiolide.
Cassane diterpenoids from Lonchocarpus laxiflorus
Authors: Igoli John O. , Onyiriuka Samuel O. , Letzel Matthias C. , Nwaji Martin N. , Gray Alexander I.
Published: March 2019

Phytochemical investigation of the stem bark of Lonchocarpus laxiflorus yielded three new cassane diterpenoids, lonchocassane A [cassa-13 (14), 15-dien-18, 20-dioic acid], lonchocassane B [cassa-13 (14), 15-dien-20-oxo-18-oic acid] and lonchocassane C [cassa-13 (14), 15-dien-20-carboxyl-18-methylcarboxylate]. The known compounds betulinic acid, betulinic acid acetate, betulin, lupeol, lupenone, trilinoleate, hexacosanyl and triacontanyl caffeates, 4-hydroxy-4-methylpentan-2-one, β-sitosterol, β-sitosterol acetate and stigmasterol were also isolated. The structures and identities of the compounds were established by spectroscopic methods.
Antimicrobial Activities of Alkaloids and Lignans from Zanthoxylum budrunga
Authors: Rahman M. Mukhlesur , Gray Alexander I. , Khondkar Proma , Islam M. Anwarul
Published: March 2019

Eight alkaloids (2–9) and two lignans (1 and 10) isolated from the stem bark of Zanthoxylum budrunga were tested against a panel of bacteria (both Gram positive and Gram negative) and fungi. Significant antibacterial activities were exhibited by all compounds against the test bacterial strains, except Klebsiella aerogenes. All compounds except the mixture of 2 and 3 showed reasonable antifungal activity against Aspergillus niger and Candida albicans. The MICs of the compounds against the test organisms were recorded in the range of 0.06–1.568 μmol.
Saponins from Fresh Fruits of Randia siamensis (Lour) Roem. & Schult. (Rubiaceae)
Authors: Khwanchuea Rapheeporn , Queiroz Emerson Ferreira , Marston Andrew , Jansakul Chaweewan , Hostettmann Kurt
Published: March 2019

Bioactivity-directed fractionation of the n-butanol extract of fresh fruits of Randia siamensis led to the isolation of 4 new ginsenosides: pseudoginsenosides-RT2, -RT3, -RT4 and -RT5, together with 7 known compounds. Tyramine was found to be responsible for the hypertensive activity, whereas pseudoginsenosides-RT1 and -RP1 were responsible for the hypotensive activity. The structures were determined by spectroscopic and chemical methods.
New Acylated Flavonol Diglycosides of Cynanchum Acutum
Authors: Mohamed Mona A. , Ahamed Wafaa S. , El-Said Mortada M. , Hayen Heiko
Published: March 2019

Three new acylated flavonol diglycosides that were characterized as quercetin 3- O-(6′”- O-E-isoferuloyl)-sophoroside (1), quercetin 3- O-(6′”- O-Z-isoferuloyl)-sophoroside (2) and quercetin 3- O-[2″- O-( E-6″′- O-isoferuloyl)-β-D-glucopyranosyl]-β-D-galactopyranoside (3), along with twelve known metabolites, have been isolated from the leaves of Cynanchum acutum L. The latter were identified as quercetin 3- O-β-D-neohesperidoside (4), rutin (5), quercetin 3- O-sophoroside (6), kaempferol 3- O-β-D-rutinoside (7), quercitrin (8), isoquercitrin (9), hyperin (10), guaijaverin (11), quercetin 7- O-β-D-glucopyranoside (12), quercetin (13), scopoletin (14) and ( E)-3-(3,4-dihydroxyphenyl)-propenoic acid (15). All metabolites have been isolated for the first time from the genus Cynanchum, except for 9 and 14. The structures were determined on the basis of chromatographic behavior, acid hydrolysis, chemical and physicochemical evidence (UV, HRESI-MS/MSn, 1H, 13C NMR, 1H-1H COSY, HSQC and HMBC). The chloroform extract and compounds 8 and 10 exhibited lethal effects towards brine shrimp, Artemia salina.
Free Radical Scavenging and Cytoprotective Activity of Salacia Euphlebia Merr
Authors: Subhadhirasakul Sanan , Keawpradub Niwat , Promwong Charuporn , Yuenyongsawad Supreeya
Published: March 2019

The present study reports the antioxidant activity of Salacia euphlebia stem extract. To understand the antioxidant activity of this plant, four compounds were isolated and elucidated as vitexin, 15α-hydroxyfriedelan-3-one, siphulitol and mangiferin. Mangiferin showed high free radical scavenging activity (EC50 1.10 ± 0.18 μg/mL) in comparison with quercetin (EC50 1.35 ± 0.02 μg/mL), while vitexin (IC50 37.6 ± 1.1 μg/mL) showed a good cytoprotective effect compared with quercetin (IC50 76.1 ± 1.0 μg/mL). This is the first report of the activities and bioactive compounds of S. euphlebia. These results may scientifically explain the folk and alternative-medicine use of this plant in longevity formulas.
A New Ferulic Ester and Related Compounds from Bombax Malabaricum DC
Authors: Singh Pahup , Mewara Durga K. , Sharma Mahesh C.
Published: March 2019

A new ferulic ester, trans-triacontyl-4-acetoxy-3-methoxycinnamate (2), was isolated, along with related known ferulates and triterpenes, from the spines of stem bark of Bombax malabaricum DC. The structures were elucidated from chemical and spectroscopic data.
Natural Variability in Enantiomeric Composition of Bioactive Chiral Terpenoids in the Essential Oil of Solidago Canadensis L. from Uttarakhand, India
Authors: Chanotiya Chandan S. , Yadav Anju
Published: March 2019

The natural variability in the enantiomeric distribution of biologically active chiral terpenoids in Solidago canadensis L. essential oil from Kumaon was evaluated by enantioselective capillary GC, capillary GC, and GC-MS. Germacrene D, a sesquiterpene hydrocarbon, was noticed as the major compound, contributing 56.7%, 75.5% and 69.7% to the samples, while other constituents with variable compositions were limonene (0.2 to 12.5%), bornyl acetate (2.1 to 2.9%), δ-elemene (2.4 to 3.2), β-elemene (1.3 to 1.8%), and elemol (1.4 to 2.6%). The enantiomeric excess has been determined for germacrene D with (+)-enantiomer (>41.8% to >47%) dominating over the (-)-enantiomer in all the samples. Furthermore, there has been above 95% enantiomeric excess for ( R)-(+)-limonene (>95.1% to >99%), whereas moderate to low excess for (1 R)-(+)-α-pinene (>47.9%), and (1 S)-(-)-β-pinene (>30.3%) was established. Notably, only (-)-bornyl acetate was found as a single enantiomer with >99% enantiomeric excess. However, for all the identified chiral terpenoids, the enantiomeric distribution varied within only a narrow range in all the samples.
Germacrone Dominates the Leaf Oil of Siparuna Grandiflora from Monteverde, Costa Rica
Authors: Setzer William N. , Agius Brittany R. , Walker Tameka M. , Moriarity Debra M. , Haber William A.
Published: March 2019

The leaf oil of Siparuna grandiflora (Monimiaceae) has been obtained by hydrodistillation and analyzed by GC-MS. The major components were germacrone (66.9%), germacrene B (8.2%), δ-cadinene (2.5%), trans-β-elemenone (2.2%), and β-elemene (2.1%). The leaf oil exhibited notable in-vitro cytotoxic activity on MCF-7 cells, brine shrimp lethality, and limited antimicrobial activity. DFT calculations (B3LYP/6-31G*) indicate that germacrone is slightly more stable than its Cope rearrangement product trans-β-elemenone.
Structural Elucidation of Pimarane and Isopimarane Diterpenoids: The 13C NMR Contribution
Authors: Seca Ana M. L. , Pinto Diana C. G. A. , Silva Artur M. S.
Published: March 2019

13C NMR spectroscopy is actually one of the first tools used for the structural elucidation of natural and synthetic compounds and it is also used in biosynthetic studies. The aim of this review is to present the 13C NMR assignments of a large number of pimarane diterpenoids, describing the most significant effects caused by different substitution patterns and different stereochemistry at their chiral centers.
Therapeutic Potential and Chemical Composition of Plants from the Genus Rubus: A Mini Review of the Last 10 Years
Authors: Niero Rivaldo , Filho Valdir Cechinel
Published: March 2019

Rubus species (Rosaceae) are appreciated for their fruits and their traditional therapeutic uses. Several experimental investigations indicate important biological effects of these plants, related to the presence of different classes of chemical substances, especially terpenoids and phenolic compounds. This work outlines the main biological properties and chemical constituents of the genus Rubus over the last 10 years, with particular emphasis on the plants that occur in Brazil.
Ring Contraction of Gummiferolic Acid, a Diterpene Isolated from Margotia Gummifera, Leading to Atisagibberellins
Authors: Anaya Josefa , Fernández Juan José , Grande Manuel , Martiáñez Justo , Torres Pascual
Published: March 2019

Gummiferolic acid (1) is an atisenoic acid derivative that shows phytohormonal activity. In order to increase this activity the natural product, after careful functionalisation, was subjected to several reaction conditions to provoke the contraction of the ring B from six to five members. Pinacolinic acid and basic rearrangements led to the desired gibberellin-like epimers (atisagibberellaldehydes) 28 and 29.
Searching for Natural Bioactive Compounds in Four Baccharis species from Bolivia
Authors: Dávila Marcelo , Loayza Ingrid , Lorenzo Daniel , Dellacassa Eduardo
Published: March 2019

The volatile oil composition of four Baccharis species ( Baccharis papilosa, B. polycephala, B. buxifolia, and B. convawyi) growing wild in Bolivia were studied by GC and GC/MS. The antimicrobial activity of the oils was determined by the agar diffusion and bioautography methods. Solvent extracts, polar and non-polar, of the same species were also tested for antimicrobial and antioxidant activities. Extracts from B. polycephala, B. papilosa and B. convawyi presented significant antioxidant activity, determined using the DPPH radical scavenging method, showing EC50 values of 4.74, 7.17 and 7.97 μg/mL, respectively. Screening for antimicrobial activity was conducted using the agar diffusion test. The most active extracts (% inhibition ≥ 50) were further examined by the dilution method. All the plant extracts studied showed higher antimicrobial activity against S. aureus (Gram-positive) than against E. coli and P. fluorescens (Gram-negative).
Terpenoids in Grapes and Wines: Origin and Micrometabolism during the Vinification Process
Authors: Carrau Francisco M. , Boido Eduardo , Dellacassa Eduardo
Published: March 2019

Terpenoids, which are typical components of the essential oils of flowers and fruits, are also present as free and glycosylated conjugates amongst the secondary metabolites of wine grape varieties of Vitis vinifera. Hence, when these compounds are present in wine, they are considered to originate from the grapes and not from fermentation. However, the biosynthesis of monoterpenes by Saccharomyces cerevisiae in the absence of grape derived precursors was shown recently to be of de novo origin in wine yeast strains. The contribution of yeast and bacterial fermentation metabolites to the aromatic profile of wine is well documented. However, the biotechnological application of this knowledge is still rather limited and often contradictory. Redox conditions, size of inoculums, temperatures of fermentation, osmotic pressure and the medium nutritional content can profoundly affect the profile of yeast and bacterial metabolites produced or their biotransformation capacity in wine. Results obtained in the last decades in relation to microbial micrometabolism of aroma compounds measured with more sophisticated GC-MS methods are discussed in relation to the known terpenoid biosynthetic pathways and wine composition. Further development of metabolic footprinting techniques for the discrimination of wine quality must be one of the main challenges for wine biotechnologists in the near future.
Monoaminergic, Ion Channel and Enzyme Inhibitory Activities of Natural Aporphines, their Analogues and Derivatives
Authors: Cassels Bruce K. , Asencio Marcelo
Published: March 2019

The aporphine alkaloids constitute the second-largest group of isoquinoline alkaloids. Nevertheless, only a relatively small number of natural aporphines and their derivatives have been studied from a pharmacological viewpoint. Here we review the pharmacological data available for these compounds as related to their dopaminergic, noradrenergic and serotonergic activities, and also some results pertaining to their effects on ion channels and enzymes.
Identification and Quantification of three Tubeimosides in Rhizoma Bolbostematis by High Performance Liquid Chromatography with Evaporative Light Scattering Detection and Electrospray Mass Spectrometric Detection
Authors: Huang Hao , Liang MingJin , Xu Wen , Zhang Chuan , Zhang WeiDong
Published: March 2019

Tubeimoside I, tubeimoside II and tubeimoside III were simultaneously determined and identified by high performance liquid chromatography coupled with electrospray tandem mass spectrometry (HPLC-ESI/MS), and a novel and sensitive high performance liquid chromatography - evaporative light scattering detection (HPLC-ELSD) in a 70% methanol extract of Rhizoma Bolbostematis. The chromatographic separation was performed on a Zorbax Extend C18 analytical column using gradient elution with a solution of acetonitrile and 0.5% acetic acid. The method was validated with acceptable linearities (r > 0.9992) and recoveries (98.6 to 102.4 %). The limits of detection of these three tubeimosides were as low as 0.05 μg. The intra- and inter-day precisions of the method were evaluated and were less than 3.6%. The method was successfully used to analyze 15 batches of Rhizoma Bolbostematis. The content of tubeimosides in the plant material varied from habitat to habitat confirming the necessity to control the quality of Rhizoma Bolbostematis during its preparation and application in the clinic.
New Derivatives of Chromene and Acetoxyeudesmane Obtained by Microbial Transformation
Authors: Haridy Mamdouh S. A. , Mohamed Abou El-Hamd H.
Published: March 2019

Microbial transformation of dihydrobenzofuran derivative 1 and 4, 6-dihydroxy-1,5(H)-guai-9-ene (2), the major isolated compounds from Chrysothamnus viscidiflorus, afforded a new chromene derivative 3 and a new acetoxyeudesmane derivative 4, respectively. The structures of the new compounds were determined by comprehensive NMR studies, including DEPT, COSY, NOE, HMQC, HMBC and HRMS.
Chemical Composition of the Essential Oils from Flower, Leaf, and Stem of Senecio Trapezuntinus Boiss. Grown in Turkey
Authors: Üçüncü Osman , Yaylı Nuran , Yaşar Ahmet , Terzioğlu Salih , Yaylı Nurettin
Published: March 2019

The chemical composition of the essential oils obtained by hydrodistillation of air-dried flower, leaf and stem of Senecio trapezuntinus Boiss were analysed by GC-FID and GC-MS. Thirty-eight compounds were identified, constituting over 91.7%, 86.2% and 73.5% of the total oil composition of flower, leaf and stem of S. trapezuntinus, respectively. Sesquiterpene hydrocarbons were shown to be the main group of constituents of all three part of the plant. The main component of the flower, leaf and stem essential oils was ( E)-β-farnesene (26.3%, 16.9%, and 31.2%, respectively).
Essential Oil Analysis of the Follicles of Four North American Magnolia Species
Authors: Schühly Wolfgang , Ross Samir A. , Mehmedic Zlatko , Fischer Nikolaus H.
Published: March 2019

The chemical composition of the essential oils obtained by steam distillation of fruits (follicles) of Magnolia fraseri Walt., M. tripetala L., M. acuminata L., and M. grandiflora L., collected in the Southeastern United States, were studied by GC/MS. A total of 35 out of 41 components were identified, most of which were monoterpenes and sesquiterpenes. Among the four investigated species, only few similarities in the compound patterns were found. The major constituents (> 10% of the essential oil) were found to be trans-nerolidol (20.0%) and 9-oxofarnesol (11.0%) in M. acuminata, β-pinene (26.3%) and β-myrcene (13.1%) in M. fraseri, β-elemene (12.2%) in M. grandiflora and bornyl acetate (17.0%), and β-caryophyllene (21.0%) and α-humulene in M. tripetala.
Essential Oil Compounds of Origanum Vulgare L. (Lamiaceae) from Corsica
Authors: Lukas Brigitte , Schmiderer Corinna , Mitteregger Ulrike , Franz Chlodwig , Novak Johannes
Published: March 2019

The essential oil compounds of 274 individual plants belonging to 13 populations of Origanum vulgare L. (Lamiaceae) from Corsica were studied by GC/FID and GC/MS. On the basis of their monoterpene chemistry three different chemotypes were obvious in the Origanum populations: The first and most common type was a ‘cymyl’ type, with either carvacrol (0.6–65.5%) or thymol (0.0–49.5%) as the main compound. The second, which was very rare, was a ‘sabinyl’ type with sabinene (7.8–20.2%) and cis-sabinene hydrate (0.7–24.8%) as main compounds. The third type was a ‘mixed’ type combining compounds of the ‘cymyl’ and the ‘sabinyl’ pathway. The ‘mixed’ type was rich in cis-sabinene hydrate (0.0–52.4%) and γ-terpinene (0.6–35.4%).
Comparative Study of the Chemical Profiles of the Essential Oils of Ripe and Rotten Fruits of Citrus Aurantifolia Swingle
Authors: Afolayan Anthony J. , Asekun Olayinka T.
Published: March 2019

Most often during the processing of lime fruits for essential oil extraction, rotten fruits are used along with ripe ones. In this study, we examine the volatile constituents of the essential oils from both ripe and rotten lime fruits (Citrus aurantifolia Swingle) from Nigeria. The oils were isolated by hydrodistillation and analyzed using GC-MS. The ripe and rotten lime oils contained 55 and 49 components, respectively. Both oils were rich in limonene (21.0%, ripe lime; 21.3% rotten lime), α-terpineol (11.7%, ripe; 14.1%, rotten), terpinene (8.3%, ripe; 8.9% rotten lime), α–terpinolene (2.5%, ripe; 8.5%, rotten) and ( E)-α-farnesene (6.3% ripe lime; 4.8% rotten lime). The other major components, α-pinene (11.1%), and linalool (5.5%) were identified in ripe lime oil only. Limonene and citral, which are believed to be the two major citrus odour contributors, were present in both ripe and rotten lime oils. Aldehydes like decanal and the farnesenes, which are also important in citrus flavor, were represented in both lime oils. Some notable components of ripe lime fruit oil, like trans-β-ocimene, linalool, myrcenol, dodecanal, trans-β–bergamotene and trans-γ–bisabolene, were absent in the rotten fruit oil. It could be suggested that some compounds like cis-ocimene, trans-linalool oxide, p-mentha-3-en-1-ol, mentha-1,4,8-triene, citronellal, trans- β–bergamotene and α–copaene, which were not identified in the ripe fruit oil, were introduced into the lime oil by the incorporation of rotten fruits in the distilled samples.
Chemical Variation in the Essential Oil Composition of Hyptis suaveolens (L.) Poit. (Lamiaceae)
Authors: Grassi Paolo , Nuñez Marvin José , Reyes Tomás Sigfrido Urías , Franz Chlodwig
Published: March 2019

Hyptis suaveolens (Lamiaceae) is an annual species which is used for aromatic and medicinal purposes. The species is polymorphic in its essential oil composition, with three distinct chemotypes in El Salvador of which the fenchone-fenchole type will be the focus of this communication. The fenchone-fenchol chemotype showed strong relative changes, especially within the monoterpenes. The main compounds of the essential oil were sabinene, 1,8-cineole, γ-terpinene, fenchone, fenchol and the sesquiterpene β-caryophyllene. Due to strong inter-individual differences, these changes are explained based on several individuals separately. Fenchol was found to decrease drastically when leaves enter the last development stage of yellowing, whereas the proportion of the ketone, fenchone, increased. Furthermore, the proportion of sesquiterpenes decreased in older tissues compared to the monoterpenes. These changes were surprising, because it was expected that yellowish leaves would lose compounds with higher vapor pressures, like sabinene and 1,8-cineole.
Micro-bore Column Fast Gas Chromatography-Mass Spectrometry in Essential Oil Analysis
Authors: Tranchida Peter Quinto , Costa Rosaria , Dugo Paola , Dugo Giovanni , Mondello Luigi
Published: March 2019

The present research is focused on the use of micro-bore column fast gas chromatography in combination with rapid-scanning quadrupole mass spectrometry for mediumly-complex essential oil analysis. A basil essential oil sample was initially subjected to conventional GC-MS (analysis time: 25 min) under optimum analytical conditions. Peak identification was carried by using a dual-filtered MS library search procedure: the first filter deleted “hits” with a less than 90% spectral similarity, while the second filter eliminated matches with a linear retention index (LRI) outside a pre-defined LRI window. The same essential oil sample was analyzed under optimized fast GC-MS conditions by using a micro-bore column, with the same aforementioned MS library search process (analysis time: 5.3 min). Resolution was altogether similar in both applications, with the same number of compounds reliably-identified, namely fifty-nine. The experiment demonstrated the usefulness of the rapid GC approach in this type of experiment.
Carbon Isotope Ratio Analysis of Authentic and Commercial Essential Oils of Lemon Balm
Authors: Wagner Susanne , Vreca Polona , Leis Albrecht , Boechzelt Herbert
Published: March 2019

Several commercial and authentic essential oils of lemon balm ( Melissa officinalis L.) were investigated for the carbon isotope ratio of their main compounds (citral as its enantiomers geranial and neral, citronellal, β-caryophyllene, germacrene D and caryophyllene oxide) by GC-C(ombustion)-IRMS. Authentic samples of lemon balm were distilled in 2003, 2004 and 2007. In addition, commercially available samples of the individual main compounds of the oil with proclaimed synthetic and natural origins were investigated for their carbon isotopic composition by GC-C-IRMS and EA-C-IRMS in order to compare the investigated carbon isotopic values. All oils were analyzed via GC-MS and GC-FID to enable the identification of the compounds in the GC-C-IRMS chromatograms and to investigate the quantity of the single essential oil compounds. Data were interpreted regarding suitability for authenticity assessment of the analyzed essential oil samples.

Synthetic citral showed δ13CPDB values of −28.68 and −29.00±, whereas the natural labelled standard showed a value of −26.89±. For the authentic oils, δ13CPDB values between −29.36 and −24.54± were determined. The commercial lemon balm oil samples indicated δ13CPDB values between −27.72 to −24.04± for citral. The synthetic citronellal standard showed a δ13CPDB value of −28.77 and the natural standard −12.91±. The value of −12.91± of the natural citronellal standard indicates, that it was possibly produced by the distillation of a C4 plant (e.g. citronella), because the δ13CPDB value is more positive than usual for C3 plants (lemon balm). The same applies to four commercial lemon balm oils with δ13CPDB values for citronellal of −15.04 to −12.24±. Authentic samples of lemon balm oils presented δ13CPDB values of −32.15 and −30.59± for citronellal. For the three minor compounds, β-caryophyllene, germacrene D and caryophyllene oxide, no clear differentiation could be made due to the lack of standards and the minor concentration of the compounds. The determination of the isotopic ratio of the stable carbon isotopes by GC-C-IRMS is a very powerful tool in authenticity assessment of essential oils for differentiation between C3 and C4 plants. Four of the investigated 19 lemon balm oils could be identified as oils of C4 plants (e.g. citronella oils), although they were labelled as lemon balm oils.
Linalool – a Review of a Biologically Active Compound of Commercial Importance
Authors: Kamatou Guy P. P. , Viljoen Alvaro M.
Published: March 2019

Since the earliest times fragrant materials have been used in rituals. Today, a lucrative industry has developed to produce and deliver fragrances and aromatic chemicals with various applications in modern society. Linalool, a much sought after compound in the flavor and fragrance industry is a monoterpene alcohol which occurs naturally in many aromatic plants. Linalool and linalool-rich essential oils are known to exhibit various biological activities such as antimicrobial, anti-inflammatory, anticancer, anti-oxidant properties and several in vivo studies have confirmed various effects of linalool on the central nervous system. The applications of linalool are not confined to simply adding or enhancing a specific scent to domestic products such as soaps, detergents and shampoos. Linalool also plays an import role in nature as a key compound in the complex pollination biology of various plant species to ensure reproduction and survival. Linalool is also a key compound for the industrial production of a variety of fragrance chemicals such as geraniol, nerol, citral and its derivatives, as well as a lead compound in the synthesis of vitamins A and E. The repellent properties of linalool on various crop-destroying insects has been well documented accentuating the application of this molecule in eco-friendly pest management. This review aims to highlight the various biological properties of linalool and to emphasize the value of linalool and linalool-rich essential oils in phytotherapy.
Integration of Plasma Membrane and Nuclear Signaling in Elicitor Regulation of Plant Secondary Metabolism
Authors: Stockman Gastón , Boland Ricardo
Published: March 2019

The plant kingdom represents a valuable source of natural products of commercial interest. These compounds, named secondary metabolites, are not essential for the survival of plants, but confer them some advantages that allow adaptation to changes in their environment. Nevertheless, yields of secondary metabolites are low for commercial purposes, so it has become important to design strategies for increasing their production. Plants manage to adapt to physical changes in their environment, defending themselves against pathogen attack or herbivore wounding. Such aggressive stimuli, also known as elicitors, initiate signaling metabolic cascades that induce accumulation of certain secondary metabolites. Progress has been recently achieved in the understanding of signaling events originating from elicitation and related transcriptional regulation. These advances will allow maneuvering expression of key enzymes implicated in biosynthetic pathways of secondary metabolites, thereby enhancing their accumulation.
Activity-guided Isolation and Identification of Free Radical-scavenging Components from Ethanolic Extract of Boneset (Leaves of Eupatorium Perfoliatum)
Authors: Habtemariam Solomon
Published: March 2019

Activity-directed fractionation and isolation procedures were used to identify the antioxidant components of Boneset (Eupatorium perfoliatum). Dried powdered leaves were extracted with ethanol and subsequently fractionated into light petroleum, chloroform, ethyl acetate, and n-butanol fractions. The ethyl acetate fraction, which showed the strongest antioxidant activity, reducing power and highest phenolic content, was subjected to Sephadex LH-20 chromatography followed by repetitive preparative TLC to afford protocatechuic acid as the major antioxidant constituent, together with small amounts of other antioxidants (hyperoside, quercetin and rutin). Similar treatment of the n-butanol fraction, the second most potent fraction, yielded predominantly rutin and a trace amount of hyperoside as active constituents. The identity of the compounds was established based on direct comparison of spectral data (UV, IR, 1D- and 2D-NMR and MS) with those of authentic samples and literature values.
Oxidative Transformations of Lappaconitine and 19-Oxolappaconine, Structural Revision of an obtained 8,9-Seco Product
Authors: Shafikova Elza U. , Tsyrlina Elena M. , Spirikhin Leonid V. , Balandina Alsu A. , Latypov Shamil K. , Yunusov Marat S. , Sinyashin Oleg G.
Published: March 2019

The oxidative transformations of lappaconitine and 19-oxolappaconine were studied. The product of oxidation of the latter with K2Cr2O7/30% H2SO4 in methylene chloride was proved to be 10,12-dihydro-8,9-seco-19-oxolappaconine in contrast to the earlier proposed structure of this compound.
New Polar Steroids from Starfish
Authors: Stonik Valentin A. , Ivanchina Natalia V. , Kicha Alla A.
Published: March 2019

A short review concerning new polar steroids isolated from starfish with 75 citations is given. This review covers the literature published from 2001 through 2007. The emphasis is on new structures, together with their relevant biological activities, source organisms, and localities of collections.
Steroidal Saponins from the Rhizomes of Ruscus Hypophyllum
Authors: Mimaki Yoshihiro , Aoki Tsukasa , Jitsuno Maki , Yokosuka Akihito , Kiliç Ceyda Sibel , Coşkun Maksut
Published: March 2019

Phytochemical screening of the rhizomes of Ruscus hypophyllum (Liliaceae) has resulted in the isolation of five spirostanol saponins (1-5) including a new saponin (4) and nine furostanol saponins (6–14) including three new saponins (9–11), together with a known cholestane glycoside (15) and a new cholestane glycoside (16). The structures of the new compounds were determined on the basis of extensive spectroscopic analysis, including 2D NMR data, and chemical evidence. The spirostanol saponins 1, 2, and 5 showed moderate cytotoxic activity against HL-60 human promyelocytic leukemia cells.
Secondary Metabolites from Teclea amanuensis (Rutaceae) from Tanzania
Authors: Magadula Joseph J. , Kapingu Modest C , Mbwambo Zakaria H. , Mulholland Dulcie A.
Published: March 2019

The dichloromethane extract of the stem bark of Teclea amaniensis has yielded two novel furoquinoline alkaloids, 5-[3-methylbut-2-enyl]-4,6,7-trimethoxyfuro[2,3- b]quinoline and 6-(2′,3′-epoxy-3-methylbutyl)-5-hydroxyl-4,7-dimethoxyfuro[2,3- b]quinoline, in addition to an acridone alkaloid, 2-hydroxy-1,3-dimethoxy-10-methylacridone. Three known alkaloids, dictamnine, kokusaginine and evoxanthine, and two known triterpenoids, lupeol and lupeol acetate were also isolated. Structures of the new compounds were established by means of NMR spectroscopic and MS data.
Chemical Constituents and Insecticidal Activity of Rollinia leptopetala (Annonaceae)
Authors: Arriaga Ângela M.C. , Feitosa Edinilza M.A. , Lemos Telma L.G. , Santiago Gilvandete M.P. , Lima Jefferson Q. , De Oliveira Maria C.F. , Vasconcelos Jackson N. e , Rodrigues Francisco E. A. , Gomes Tathilene B. M. , Braz-Filho Raimundo
Published: March 2019

The present work describes the isolation of dehydrodiscretamine, discretamine, liriodenine, lichexanthone, molvizarin, rolliniastatin-1, annonacin and bullatacin from roots of Rollinia leptopetala R E Fries. The structures were established after analysis of their NMR spectral data including 2D NMR experiments. With the exception of discretamine, the presence of these compounds in R. leptopetala and the NMR data of dehydrodiscretamine are reported for the first time. The CH2Cl2 extract of the roots demonstrated high larvicidal activity against Aedes aegypti, with an LC50 value of 1.44±2.0 ppm.