bluuebunny/crossref_metadata_2025 huggingface dataset:
Antibacterial Bromophenol from the Marine Red Alga Pterosiphonia complanata
Authors: Etahiri Samira , El Kouria Abdel Kebir , Bultel-Poncé Valérie , Guyot Michèle , Assobhei Omar
Published: March 2019

The dichloromethane/methanol extract of the red alga Pterosiphonia complanata exhibited antibacterial activity against many potentially pathogenic Gram (+) and Gram (-) bacteria. The compound responsible for this activity was isolated and identified, mainly on the basis of 1H and 13C NMR experiments, as the known 3,4,6-tribromo-5-methoxymethyl-benzene-1,2-diol. Its minimum inhibitory concentration against Staphylococcus aureus was 2.8 μg/mL (7 nM).
Isolation and Characterization of the ‘Flavonoid Crystals’ of Three Species of Prosthechea: Chemotaxonomic Considerations of the Genera Prosthechea and Encyclia
Authors: Bhattacharyya Jnanabrata , de F. de Oliveira Pires Maria , Felix Leonardo P. , Silva Tania M. S. , Majetich George F.
Published: March 2019

The isolation of fragnettin, the so called ‘flavonoid crystals’, from three species of Prosthechea, namely P. fragrans, P. vespa and P. caetensis, and its characterization as 8- C-β-D-quinovopyranosyl apigenin is described. The possibility of fragnettin (8- C-β-D-quinovopyranosyl apigenin), the ‘flavonoid crystals’ absent in the genus Encyclia, being the marker of the genus Prosthechea is suggested.
Anti-Babesial Compounds from Rosa damascena Mill
Authors: Elkhateeb Ahmed , Matsuura Hideyuki , Yamasaki Masahiro , Maede Yoshimitsu , Katakura Ken , Nabeta Kensuke
Published: March 2019

Bioassay-guided investigation of extracts of the flowers of Rosa damascena Mill. led to the isolation of four anti-babesial compounds, 3,4-dihydroxy benzoic acid (1), gallic acid (2), 2-phenylethyl 6- O-galloyl-β-D-glucopyranoside (3), and quercetin 3- O-β-D-(6- O-acetyl)-glucopyranosyl-(1→4)-α-L-rhamnopyranoside (9), in addition to five flavonoid compounds which possessed weak anti-babesial activity, kaempferol 3- O-β-D-glucopyranoside (4), kaempferol 3- O-β-D-xylopyranoside (5), kaempferol 3- O-α-L-rhamnopyranoside (6), quercetin 3- O-β-D-glucopyranoside (7), and quercetin 3- O-α-L-rhamnopyranoside (8). Among the isolated compounds, 3 possessed the greatest anti-babesial activity with an IC50 value of 11.78 μg/mL. Although compound 3 is known, no published reports list detailed spectroscopic data for the molecule. Therefore, the first complete structural elucidation of 3 using 1D and 2D NMR spectroscopic analysis is reported here. This is the first report of the isolation of compounds 1, 5, and 9 from R. damascena.
Bark and Leaf Essential Oil of Umbellularia californica, California Bay Laurel, from Oregon
Authors: Kelsey Rick G. , McCuistion Ovid , Karchesy Joe
Published: March 2019

The bark and leaf essential oil of Umbellularia californica (Hook. & Arn.) Nutt. from west central Oregon, USA, was isolated by steam distillation and the chemical composition analyzed by GC-FID and GC-MS. The three major components in bark oil were 1,8-cineole (36.0%), α-santalene (9.3), and α-terpineol (6.9%), while those in leaf oil were umbellulone (41.0%), 1,8-cineole (22.0%) and sabinene (10.2%).
Two Distinct Essential Oil Bearing Races of Tanacetum nubigenum Wallich ex DC from Kumaon Himalaya
Authors: Chanotiya Chandan S. , Mathela Chandra S.
Published: March 2019

The essential oil from the aerial parts of Tanacetum nubigenum Wallich ex DC collected from the Milam glacier moraine showed the presence of 73 compounds, of which 69, representing 87.9% of the total oil, have been identified, with bornyl acetate (39.7%), borneol (10.6%), ( E)-β-farnesene (6.6%) and 1,8-cineole (5.8%) as major constituents, while the oil from the plant material from the Pindari glacier area contained a total of 81 compounds, of which 77 have been identified. This oil was characterized by the presence of (3 R, 6 R)-linalool oxide acetate (69.4%), β-eudesmol (3.2%), selin-11-en-4α-ol (3.2%) and (3.2% and 1.2%, respectively) for compounds ( E) and ( Z)-2-(2,4-hexadiynylidene)-1,6-dioxospiro [4,4] non-3-ene, respectively. The major constituents of the essential oils from the aerial parts were separated and characterized by GC, GC/MS and 1D- and 2D-NMR spectroscopy. The chemical differences between the two essential oils place them as distinct chemical races or chemotypes.
Myorelaxant Effect of Essential Oil of Rhizome of Alpinia calcarata Rosc. on Rat Duodenal Smooth Muscle
Authors: Pandey Siddharth , Prakash Om , Zafar Anjum , Hore Subrata K. , Pant Anil K. , Mathela Chandra S.
Published: March 2019

Analysis of the essential oil from the rhizome of Alpinia calcarata Rosc. (ACREO) by a combination of GC and GC-MS revealed the presence of 1,8-cineole (42.2%), endo-fenchyl acetate (14.7%), camphene (7.6%), β-pinene (6.9%), α-terpineol (5.3%) and camphor (5.0%). Twenty-three compounds were identified in the oil. ACREO showed dose dependent myorelaxant activity in rat duodenum. The dose response curves of acetylcholine (ACh) and CaCl2 were shifted by ACREO to the right with increases in EC50 values and decreases in Vmax. These findings suggest that ACREO is a non-competitive antagonist of ACh and calcium.
Cytotoxic Sesquiterpene Lactones of Egyptian Tanacetum santolinoides
Authors: Youssef Diaa T. A. , Ramadan Mahmoud A. , Ibrahim Sabrin R. M. , Badr Jihan M.
Published: March 2019

The chloroform soluble fraction of the methanolic extract of the aerial parts of Tanacetum santolinoides afforded six sesquiterpene lactones. Tanacetolide A (1) was isolated for the first time from a natural source, in addition to five known sesquiterpene lactones. The structures were established on the basis of extensive studies of their 1D and 2D (1H-1H COSY, HMQC, HMBC, HOHAHA and NOESY) NMR spectra and FAB mass spectral determinations. The compounds showed good cytotoxic activity when tested using the brine shrimp bioassay.
Protective Role of Trigonella hamosa Saponins Against Diabetic Perturbations and Complications in Rats
Authors: Salah-Eldin Alaa-Eldin , Mahalel Usama Ahmed , Hamed Arafa I.
Published: March 2019

Trigonella hamosa saponins (SS) were purified using Sephadex LH-20. The effects of SS on diabetes, lipid profiles and glucose homeostasis were investigated by supplementation of the diet of rats with SS, which countered the adverse, harmful effects of chronic diabetes by improving insulin synthesis, secretion and action, enhancing lipid and protein metabolism, and removing the oxidative stress concomitant with glucose homeostasis.
Inhibitory Effects of Cissus quadrangularis L. Derived Components on Lipase, Amylase and α-Glucosidase Activity in vitro
Authors: Sharp Hazel , Hollinshead Jackie , Bartholomew Barbara B. , Oben Julius , Watson Alison , Nash Robert J.
Published: March 2019

The stems of Cissus quadrangularis L (Vitaceae) have been consumed for centuries throughout Asia and Africa as a culinary vegetable. The aqueous extract of C. quadrangularis stems and leaves contains flavonoids and stilbenes, which inhibit lipase, amylase and α-glucosidase and, therefore, might be, at least in part, related to the claimed anti-obesity activity of the plant. The enzyme inhibition activity is outlined of a novel flavonoid (3- O-α-L-rhamnopyranosylkaempferol) (2) and stilbene (3-(4-hydroxybenzylidene)-2-(2,5-dihydroxyphenyl)-1-(4-hydroxyphenyl)indane-4,6-diol) (7), four known structurally related flavonoids, and one stilbene isolated from the extract.
Investigation of Phenolic Constituents of Carduncellus eriocephalus Boiss. var. albiflora Gauba and their Biological Activities
Authors: Shabana Marwan M. , El-Sherei Moshera M. , Moussa Mohamed Y. , Sleem Amani A. , Abdallah Hosam M.
Published: March 2019

The total ethanolic extract (TEE) of Carduncellus eriocephalus Boiss. var. albiflora Gauba showed antioxidant, antihyperglycaemic, and antihyperlipidaemic activities, which were attributed to the n-butanol fraction (BF). Chemical investigation of the BF led to the isolation of a new flavonoid, kaempferol-3- O-β-D-galactopyranoside-6″-sulfate (16), and a phenyl propenyl glycoside, 1-β-D-glucopyranoside-3-phenyl-2-propenol (rosin) (6), which is reported for the first time in the family Asteraceae. Chrysoeriol (1), 3′- O-methylorobol (2), luteolin (3), quercetin (4), myricetin (5), kaempferol 3- O-α-L-arabinopyranoside (7), kaempferol 3- O-β-D-glucopyranoside (8), quercetin 3- O-β-D-glucopyranoside (12), luteolin 7- O-β-D-rutinoside (13), quercetin 3- O-β-D-rutinoside (14), apigenin 7- O-β-D-rutinoside (15), and 3,5-dicaffeoylquinic acid (17) were isolated for the first time from the genus Carduncellus, in addition to apigenin 7- O-β-D-glucopyranoside (9), chryseriol 7- O-β-D-glucopyranoside (10) and luteolin 7- O-β-D-glucopyranoside (11), which have been previously reported for C. eriocephalus.
Combined Analysis by GC (RI), GC/MS and 13C NMR Spectroscopy of Elsholtzia blanda, E. penduliflora and E. winitiana Essential Oils
Authors: Lesueur Dominique , Bighelli Ange , Tam Nguyen Thi , Than Nguyen Viet , Dung Pham thi Kim , Casanova Joseph
Published: March 2019

The chemical composition of six oil samples, isolated from aerial parts of Elsholtzia blanda, E. penduliflora and E. winitiana, harvested in two provinces of Vietnam, was investigated by GC, in combination with retention indices (RI), GC/MS and 13C NMR spectroscopy. Linalool was the major component (75.2 and 56.8%) of the two samples of E. blanda essential oil, whereas the two oil samples from E. penduliflora were dominated by 1,8-cineole (62.7 and 65.5%). Conversely, the two oil samples of E. winitiana exhibited different compositions, rosefuran (56.0%) and dehydroelsholtzia ketone (22.8%) being the major components of one sample, whilst the second sample was dominated by elsholtzia ketone (87.5%).
Betaines and N-Methylprolines from Venezuelan Plants
Authors: Adrian-Romero Maricela , Blunden Gerald , Patel Asmita V. , Armstrong Nigel , Meléndez Pablo , Cuervo Alfredo Carabot
Published: March 2019

A collection of tropical Angiosperms, mainly collected in Amazonas and Apure States in Venezuela, has been examined for the presence of betaines and N-methylprolines, which were found in 58 out of the 65 species investigated. Betaine yields were generally low, but in the species that contained N-methylprolines, the yields of these compounds were generally in excess of 0.5% of the plant dry weight. N-methylprolines were isolated from four species of Loranthaceae, all four examined species of Miconia (Melastomataceae), Pleonotema variabilis (Bignoniaceae), Gustavia augusta and Lecythis corrugata (Lecythidaceae), and Machaerium humboldtianum (Fabaceae). Trans-4-hydroxyprolinebetaine was isolated in high yields from Amphilophium paniculatum, Arrabidaea candidans and Clytostoma binatum (Bignoniaceae), Combretum laxum (Combretaceae) and Gustavia augusta (Lecythidaceae).
3-O-(3′-Hydroxytetradecanoyl)lupeol from Sorocea trophoides Inhibits Cruzain
Authors: Richter Lori R. , Vogler Bernhard , Penton Ashley F. , Setzer William N. , Haber William A. , Caffrey Conor R. , Hansell Elizabeth , McKerrow James H.
Published: March 2019

The crude chloroform extract from the stem bark of Sorocea trophoides (Moraceae) showed in-vitro inhibition of the cysteine protease cruzain. Activity-directed fractionation led to isolation of the novel 3- O-(3′-hydroxytetradecanoyl)lupeol as the inhibitory agent. The structure was elucidated by analysis of NMR spectra.
A Straight-Chain Alcohol Glycoside, with Smooth Muscle Relaxant Activity, from Rubus idaeus (Raspberry) Leaves
Authors: Patel Asmita V. , Dacke Christopher G. , Blunden Gerald , Vera Janne Rojas
Published: March 2019

A methanolic extract of Rubus idaeus leaves, when fractionated by column chromatography, yielded two distinct bands containing compounds that demonstrated in vitro, dose dependent, smooth muscle relaxant activity using transmurally-stimulated Guinea pig ileum preparations. From band two, following extensive chromatographic separation, several compounds with smooth muscle relaxant activity were obtained, one of which was characterized, from spectroscopic and mass spectrometric data, as 1- O-(1,2-dihydroxyethyl)-4- O-methoxy-β-D-glucopyranosyl-(1→3)-β-D-glucopyranoside.
Spinocoumarin I, a New Coumarin Derivative from Astragalus spinosus Forssk
Authors: Radwan Mohamed M. , El-Sebakhy Nadia A. , Asaad Aya M. , Toaima Soad M. , Kingston David G. I.
Published: March 2019

Phytochemical investigation of the roots of Astragalus spinosus Forssk (Fabaceae) resulted in the isolation of ten metabolites. The structure of spinocoumarin I (1), a new coumarin derivative, was established as 3-[( cis-2′,5′-dihydroxycinnamoyl)]-7-hydroxy-6-methoxycoumarin. The structures of the isolated compounds were determined using spectroscopic methods. All compounds exhibited weak antiproliferative activity against the A2780 ovarian cancer cell line.
1-O-Alkylglycerol Ether Lipids in Two Holothurian Species: Cucumaria japonica and C. okhotensis
Authors: Rybin Viatcheslav , Pavel Konstantin , Mitrofanov Dmitry
Published: March 2019

1- O-Alkylglycerol ether lipids were investigated in two holothurian species, Cucumaria japonica and C. okhotensis. Species specific differences in the content of 1- O-alkylglycerol ether lipids were found. Some alkyl radicals of the 1- O-alkylglycerol ether lipid molecules contained branched hydrocarbon chains. The ratio between the content of linear and branched saturated 1- O-alkylglycerol ether lipids was 1.53 in C. okhotensis and 0.55 in C. japonica.
Furanosesquiterpenoids from Lindera pulcherrima (Nees.) Benth. ex Hook. f
Authors: Joshi Subhash C. , Padalia Rajendra C. , Bisht Dinesh S. , Mathela Chandra S.
Published: March 2019

The essential oil of the leaves of Lindera pulcherrima (Nees.) Benth. ex Hook. f. was examined by GC, GC/MS and NMR spectroscopy. Furanosesquiterpenoids [furanodienone (46.6%) and curzerenone (17.6%)] were the major constituents of the oil, along with furanodiene (1.8%) and curzerene (1.2%). Other constituents in significant amount were spathulenol (4.5%), β-selinene (2.0%), germacrene B (1.9%), curcuphenol (1.9%) and 10- epi-γ-eudesmol (1.8%). The composition of the oil differs from that of other Lindera species with respect to the conspicuous absence of monoterpenoids and other furan derivatives reported so far.
Composition of the Leaf and Inflorescence Essential Oil of Pogostemon benghalensis Burm. F. from Kumaon
Authors: Chanotiya Chandan S. , Yadav Anju , Singh Anil K. , Mathela Chandra S.
Published: March 2019

Two samples of Pogostemon benghalensis Burm. F. collected from different altitudes of the Kumaon region of Uttarakhand have been analyzed by GC and GC-MS. The inflorescence oil of sample I contained β-bisabolene (18%), ( E)-β-ocimene (3.7%), and 1-octen-3-ol (2.7%), but the leaf oil showed a high elemol content (20.5%), along with β-caryophyllene (12.5%), β-copaen-4α-ol (7.7%), α-humulene (4%), and linalool (2.1%). In contrast, the inflorescence oil of sample II possessed β-caryophyllene (15.2%), β-copaen-4α-ol (9.6%), and β-bisabolene (8%), while ( E)-β-ocimene (5.2%), elemol (4%), α-guaiene (3.8%), and humulene epoxide II (2.4%) were found in the leaf essential oil. Elemol, β-copaen-4α-ol, ( Z)- and ( E)-β-ocimene are being reported for the first time from this species.
Genus Chrysothamnus: A Source of Bioactive Compounds
Authors: Hegazy Mohamed-Elamir F. , Mohamed Abou El-Hamd H. , El-Razek Mohamed H. Abd , Hammouda Fayza M. , Hassan Nahed M. , Mahalel Usama A. , El-Halawany Ali M. , Mahmoud Ahmed A. , Karchesy Joe , Hirata Toshifumi , Ahmed Ahmed A.
Published: March 2019

This review is written to take into account the rapid development in the taxonomy and phytochemistry of Chrysothamnus species. The article reviews the usage and biological activities of Chrysothamnus compounds, as well as recent progress regarding the use of this genus in clinical research.
Phytochemical Investigations of an Antitubercular Extract of Chilean Myrcianthes coquimbensis and Related Populations
Authors: Khera Smriti , Montenegro Gloria , Timmermann Barbara
Published: March 2019

The CH2Cl2-MeOH (1:1) extract of a Chilean plant Myrcianthes coquimbensis (Barnéoud) Landrum et Grifo was found to inhibit the growth of Mycobacterium tuberculosis by 73% at a concentration of 50 μg/mL. The bioassay guided separation of this extract led to the isolation of a new monoterpene (1 S,3 S,4 R)-1-methyl-4-(1-methylethenyl)-1,3-cyclohexanediol (3β-hydroxy- cis-β-terpineol, 1), along with oleanolic acid, 3β-caffeoyl-olean-12-en-28-oic acid, trans-(+)-sobrerol, epi-catechin, and catechin. The structure of 1 was determined by GC/MS, and 1D and 2D NMR spectroscopic experiments, and its absolute configuration was established by Mosher's esterification. The antitubercular activities of all isolates were evaluated using the microplate alamar blue assay (MABA). Oleanolic acid was determined to be active with an MIC value of 65.04 μM in MABA and low cytotoxicity to African green monkey vero cells, with an IC50 value of >224.5 μM, whereas all other isolates were inactive. The CH2Cl2-MeOH (1:1) extracts of two additional populations of M. coquimbensis procured from different regions in Chile have also been analyzed by LC/MS and the compounds isolated have been identified in these extracts based on retention time, observed LC/MS parent ion, and MS/MS fragmentation pattern.
Isolation and Structure Determination of Compounds from Stachys yemenensis Hedge
Authors: Soliman Hesham SM , El-Dib Rabab , Shalaby Nagwa MM , Duddeck Helmut , Simon Andras , Tóth Gabor
Published: March 2019

In spite of several studies of Stachys species, the literature lacks any information about the constituents of S. yemenensis Hedge. We report here the isolation of a new sesquiterpenetriol, stachytriol (1), along with the known compounds β-sitosterol (2), ursolic acid (3), penduletin (4), and benghalensin B (5). The structure elucidation of all isolated compounds was performed by extensive 1D and 2D NMR spectroscopic investigation.
Structure Elucidation of a New Rearranged Abietane Diterpene from a Biologically Active Plant, Salvia eriophora
Authors: Topçu Gülaçtı , Kolak Ufuk , Balcı Kubilay , Ulubelen Ayhan
Published: March 2019

A new rearranged abietane diterpenoid, eriophoroxide (1), was obtained from the root extract of Salvia eriophora Boiss. and Kotschy ex Boiss. Its structure was elucidated by spectroscopic methods and semi-empirical/ ab-initio calculations. DNA damaging, cytotoxic and antioxidant activities of the plant extract were tested.
Chemodiversity Studies on Exudate Flavonoids of Cleomaceae species (Brassicales)
Authors: Wollenweber Eckhard , Valant-Vetschera Karin M. , Roitman James N.
Published: March 2019

Seven species of the genus Cleome were analysed for formation of exudate flavonoids. The majority of structures found were polymethoxyflavonols with 6- and/or 8- O-substitution. A novel compound, isolated from C. felina, was determined to be 5,3′,4′-triOH-3,6,7,5′-tetraOMe-flavone (1), and a further novel compound, 5,3′-diOH-3,7,8,4′,5′-pentaOMe-flavone (3), was isolated from C. viscosa. Flavones with corresponding substitution have primarily been found in C. droserifolia. Rather simple flavanones such as naringenin-7-Me have so far been found only in one accession of C. hassleriana. The flavonoid profiles of the newly studied species and accessions are discussed in relation to phytochemical, taxonomical and pharmacological data.
Detection and Quantification of Engineered Proanthocyanidins in Transgenic Plants
Authors: Peel Gregory J. , Dixon Richard A.
Published: March 2019

Proanthocyanidins (PAs) are oligomeric plant natural products mostly derived from epicatechin and/or catechin monomers. In studies aimed at engineering PAs into plant tissues that do not naturally make these compounds, we have expressed PA biosynthetic and regulatory genes in tobacco, alfalfa ( Medicago sativa) and the model legume Medicago truncatula. Because engineered tannins may be produced in small quantities and it is often necessary to screen many independent plant lines, we have developed an improved, highly sensitive method to quantify and determine the composition of oligomeric PAs in plant extracts. The method involves normal-phase HPLC separation of semi-purified PAs followed by post-column reaction with the PA-specific reagent DMACA (dimethylaminocinnamaldehyde). This procedure allows for accurate and sensitive quantification of individual oligomeric PAs and, unlike currently used methods, does not require exhaustive sample preparation and clean-up. Compositional data are shown for genetically engineered PAs in tobacco and alfalfa.
Inhibition of Helicobacter pylori and Gastric Cancer Cells by Lipid Aldehydes from Viburnum opulus (Adoxaceae)
Authors: Laux Maria Teresa , Aregullin Manuel , Rodriguez Eloy
Published: March 2019

A unique group of bioactive, naturally occurring lipid aldehydes were isolated from the fruits of Viburnum opulus, (family Adoxaceae). The natural occurrences of these fatty acid derived aldehydes are reported here for the first time. Helicobacter pylori is a prevalent gastroduodenal pathogen, a causal agent of chronic gastritis and peptic ulcers and an important co-factor in gastric cancer development. We investigated the chemistry and bioactivity of these active constituents by evaluating their ability to inhibit the growth of H. pylori and to induce apoptosis in a gastric cancer cell line (CRL-5971) in vitro.
Purification Method for Multi-residual Pesticides in Green Tea
Authors: Oh Chang-Hwan
Published: March 2019

Dried green tea leaves, fortified with more than 190 multi-class pesticides, were analyzed by the newly modified Luke multiresidue method. This consists of acetone-acetonitrile extraction, dichloromethane partition and florisil cartridge purification, eluting with n-hexane-dichloromethane-acetonitrile (50:45:5), which was optimized in this study. The final sample, in n-hexane, was analyzed by GC-ECD and/or NPD. Of the 194 pesticides tested, 147 pesticides were recovered with more than 70% from dried green tea leaves. Eighteen pesticides were not recovered at all with this method.
Terpenoids from Iranian Salvia Species
Authors: Rustaiyan Abdolhossein , Masoudi Shiva , Tabatabaei-Anaraki Maryam
Published: March 2019

Apart from their common constituents (terpenoids and flavonoids) and their interesting biological activities, the genus Salvia is unusual as it is the only genus in the Labiatae that contains sesterterpenes (C25). Since these rare and interesting compounds were, for the first time, isolated and identified from Iranian Salvia species by the senior author, their NMR spectroscopic data are briefly reviewed. The terpenoid constituents of the Iranian Salvia species are also summarized.
Pentacyclic Triterpenoids from the Aerial Parts of Origanum Syriacum
Authors: Mahmood Iffat , Mohammad Faryal Vali , Firdous Sadiqa , Ahmad Viqar Uddin
Published: March 2019

From the aerial parts of Origanum syriacum a new lupane-type triterpenoid aldehyde has been isolated, together with betulinic acid, lupeol, and oleanolic acid. The new compound, origanal (1), was established as 3β-hydroxy-lup-20(29)-ene-30-al-28-oic acid from spectroscopic data.
A New Lupane Triterpenoid from Peganum Harmala
Authors: Narender Tadigoppula , Khaliq Tanvir , Arora Ashish
Published: March 2019

A new lupane triterpenoid, 27-hydroxylup-20(29)-en-27-O-(3,4-dimethoxycinnamoyl)-28-oic acid methyl ester (1) was isolated from the seeds of Peganum harmala. The structure was determined from extensive 1D- and 2D- NMR spectroscopic data.
Inhibition of Cruzain by Triterpenoids Isolated from a Salacia Species from Monteverde, Costa Rica
Authors: Agius Brittany R. , Vogler Bernhard , Stokes Sean L. , Setzer William N. , Caffrey Conor R. , Hansell Elizabeth , McKerrow James H.
Published: March 2019

The crude chloroform bark extract of an undescribed species of Salacia from Monteverde, Costa Rica, showed cruzain inhibitory activity (IC50 = 11.4 ± 0.6 μg/mL). Activity-directed chromatographic separation led to isolation of four active friedelane triterpenoids, 25,28-dihydroxyfriedelin, canophyllol, tingenone, and the novel 29-hydroxyfriedelan-3-on-28-al.
Isolation of a C-21 Norpregnane Precursor from Hoya Parasitica
Authors: Srivastava Rinky , Narain Deepali , Deepak Desh , Khare Anakshi
Published: March 2019

A novel norpregnane, foligenin (1), was isolated, along with the pregnane calogenin, from Hoya parasitica. The structure of 1 was elucidated as 3β-hydroxy-21-norpregna-5-ene by spectroscopic methods.
A New C-geranylated Isoflavone from Dalbergia Paniculata
Authors: Khalivulla Shaik I. , Reddy Bandi A. K. , Gunasekar Duvvuru , Murthy Madugula M. , Rao Tadikimalli P. , Blond Alain , Bodo Bernard
Published: March 2019

A new geranylated isoflavone, 8-C-geranyl-7-O-methylbiochanin A (1), together with two known isoflavones, olibergin B (2) and biochanin A (3), and a known rotenoid, dehydrodeguelin (4) were isolated from the roots of Dalbergia paniculata. The structures of 1–4 were established by spectroscopic techniques including 1D and 2D NMR methods.
Three New Flavonoids from Aerial Parts of Ambrosia Maritima L
Authors: Salib Josline Y. , Michael Helana N.
Published: March 2019

Three new flavonoids, namely 6-methoxyluteolin-4′-O-lactate, apigenin-4′-O-α-L-rhamnopyranoside and tamarixetin-3-{O-[β-D-glucopyranosyl-(1→2)]-α-L-rhamnopyranoside}-7-O-β-D-glucopyranoside, together with six known flavones have been isolated from the aerial parts of Ambrosia maritima L. The structures of the isolated compounds have been established by conventional methods of chemical and physical analyses and were confirmed by 1H and 13C NMR spectroscopy.
Brevipsidone, a New Depsidone and Other α-Glucosidase Inhibitors from Garcinia Brevipedicellata (Clusiaceae)
Authors: Ngoupayo Joseph , Noungoue Diderot T. , Lenta Bruno N. , Tabopda Turibio K. , Khan Shamsun N. , Ngouela Silvère , Shaiq Mohammad A. , Tsamo Etienne
Published: March 2019

Brevipsidone (1), a new depsidone was isolated from the methanol extract of the stem bark of Garcinia brevipedicellata together with known damnacanthal (2), pilloin (3), scopoletin (4). The structure of the new compound was determined by analysis of spectroscopic data. Compounds 1–4 were evaluated for their α-glucosidase inhibition effect and showed significant inhibitory activity.
New Bromopyrrole Alkaloids from the Marine Sponges Axinella Damicornis and Stylissa Flabelliformis
Authors: Hassan Wafaa , Elkhayat Ehab S. , Edrada Ru AnGelie , Ebel Rainer , Proksch Peter
Published: March 2019

Investigation of the tropical sponges Axinella damicornis and Stylissa flabelliformis, family Axinillidae, afforded five new bromopyrrole alkaloids (1–5) and thirteen known compounds (6–18). Semi synthesis of 5 was carried out in order to confirm its structure. The structures of the isolated compounds were elucidated using 1D- and 2D-NMR spectroscopy and mass spectrometry. The cytotoxicity, antimicrobial and protein-kinase inhibition activities were tested for the isolated compounds.
Cruzain Inhibitory Activity of Leaf Essential Oils of Neotropical Lauraceae and Essential Oil Components
Authors: Setzer William N. , Stokes Sean L. , Penton Ashley F. , Takaku Sayaka , Haber William A. , Hansell Elizabeth , Caffrey Conor R. , McKerrow James H.
Published: March 2019

The leaf essential oils of twenty-three species of Lauraceae from Monteverde, Costa Rica, have been screened for inhibition of the cysteine protease cruzain. Of these, nine showed promising cruzain inhibitory activity (IC50 < 100 μg/mL), six showed marginal activity (IC50, 100–500 μg/mL), and eight were inactive (IC50 > 500 μg/mL). The cruzain inhibitory activities of the essential oils can be attributed to active sesquiterpenoid components as well as synergistic effects between two or more components. The sesquiterpenes α-copaene, β-caryophyllene, α-humulene, and germacrene D are active (IC50 ~5–30 μg/mL) alone, but also show increased activity in combination with other essential oil components.
Chemical Composition and Larvicidal Activity against Aedes Aegypti of Essential Oils from Croton Zehntneri
Authors: Santos Hélcio S. , Santiago Gilvandete M. P. , de Oliveira João P. P. , Arriaga Angela M. C. , Marques Délcio D. , Lemos Telma L. G.
Published: March 2019

The chemical composition of the essential oils from leaves, stalks and inflorescences of Croton zehntneri obtained by hydrodistillation were analyzed by GC-MS and CG-FID. E-Anethole was the main component of the essential oils of all plant parts. Essential oils of leaves, stalks, inflorescences and E-anethole were tested at different concentrations against instar III larvae of Aedes aegypti and showed LC50 values of 56.2 ± 0.3, 51.3 ± 0.3, 57.5 ± 0.1 and 69.2 ± 0.5 μg/mL, respectively.
Composition and Larvicidal Activity of Essential Oil from Stemodia Maritima L
Authors: Arriaga Angela M. C. , Rodrigues Francisco E. A. , Lemos Telma L. G. , de Oliveira Maria da C. F. , Lima Jefferson Q. , Santiago Gilvandete M. P. , Braz-Filho Raimundo , Mafezoli Jair
Published: March 2019

The leaves and stems of Stemodia maritima, collected in the state of Ceara, Brazil, were subjected to hydrodistillation and their essential oils were analyzed by combined GC and GC/MS. The major components found in the leaf oil were β-caryophyllene and 14-hydroxy-9-epi-β-caryophyllene, while in the stem oil β-caryophyllene and caryophyllene oxide were the most abundant constituents. Furthermore, the oils were examined with respect to their larvicidal properties against the larvae of Aedes aegypti and showed LC50 values of 55.4 ± 1.03 and 22.9 ± 0.85 ppm for the leaves and stems, respectively.
Cytotoxic Leaf Essential Oils from Neotropical Lauraceae: Synergistic Effects of Essential Oil Components
Authors: Wright Brenda S. , Bansal Anita , Moriarity Debra M. , Takaku Sayaka , Setzer William N.
Published: March 2019

The leaf essential oils of Beilschmiedia sp. nov. “chancho blanco”, Cinnamomum costaricanum, Ocotea meziana, Ocotea sp. nov. “los llanos” and Ocotea sp. nov. “small leaf” showed notable in-vitro cytotoxic activity on MCF-7 cells. In order to examine possible synergistic effects of essential oil components, cytotoxic activities of 1:1 binary mixtures of a number of volatile compounds were determined. Notable synergistic cytotoxic enhancement was observed for mixtures of various compounds with citral, citronellal, and artemisia ketone. The cytotoxic activity of α-humulene, on the other hand, was antagonized by pinenes, thujene, and camphene. Likewise, camphene and terpinen-4-ol reduced the activity of β-caryophyllene.
Chemical Composition of Leaf Essential Oil of Hedyosmum arborescens and Evaluation of Its Anticancer Activity
Authors: Sylvestre Muriel , Pichette André , Longtin Angélique , De Ker Martin Marie-Anna Couppé , Bercion Sylvie Rodin , Legault Jean
Published: March 2019

The essential oil of Hedyosmum arborescens Sw. (Chloranthaceae), a native plant of the Caribbean archipelago, was extracted by hydrodistillation. The chemical composition of the volatile fraction was determined by GC and GC-MS analyses and 50 components were identified. The major components are α-phellandrene (11.4%), bicyclogermacrene (10.6%) and sabinene (9.7%). The anticancer activities of these extracts were assessed against human lung carcinoma cell line A-549 and human colon adenocarcinoma cell line DLD-1. The leaf essential oil of H. arborescens was found to be moderately active against both cancer cell lines with GI50 values of 158 ± 7 μg/mL for A-549 and 178 ± 9 μg/mL for DLD-1.
Volatile Leaf Constituents and Anticancer Activity of Bursera Simaruba (L.) Sarg. Essential Oil
Authors: Sylvestre Muriel , Longtin André Pichette Angélique , Legault Jean
Published: March 2019

Leaf volatile components of Bursera simaruba (L.) Sarg., a native tree from tropical America used in traditional medicine, were extracted by hydrodistillation. The essential oil was analyzed by GC-MS. We have identified 38 compounds in this oil, of which limonene (46.7%), β-caryophyllene (14.7%), α-humulene (13.2%) and germacrene D (7.6%) are the major components. The anticancer activity of the essential oil was tested on human lung carcinoma cell line A-549 and human colon adenocarcinoma cell line, DLD-1. B. simaruba leaf essential oil was found to be active against both tumor cell lines, with a GI50 of 42 ± 2 μg/mL for A-549 and 48 ± 2 μg/mL for DLD-1. The evaluation of the cytotoxic properties of the major constituents of the oil indicates that α-humulene is possibly responsible for this activity.
Antibacterial and Cytotoxic Activity of Nepeta Cataria L., N. Cataria Var. Citriodora (Beck.) Balb. and Melissa Officinalis L. Essential Oils
Authors: Suschke Ulrike , Sporer Frank , Schneele Jürgen , Geiss Heinrich Konrad , Reichling Jürgen
Published: March 2019

The aim of the present study was to investigate the susceptibility of bacteria that play a role in respiratory tract and skin infections to the essential oils of catnip (Nepeta cataria), lemon catnip (N. cataria var. citriodora) and lemon balm (Melissa officinalis) with regard to their chemical composition. In addition, we wanted to assess whether antibiotic-resistant and -sensitive strains differ in their susceptibility to the oils and if there are cross resistances between standard antibiotics and essential oils. To evaluate the safety of topical application, cytotoxicity of the oils was studied in human keratinocyte and bronchial epithelial cell lines and irritation threshold concentrations were determined in ovo using the HET-CAM-test. The composition of the essential oils was analyzed by GC and GC-MS. Their MICs and MBCs were determined by a broth microdilution method against both reference strains from culture collections and clinical isolates with different susceptibility to standard antibiotics. Cytotoxicity was assessed by the MTT assay. Except for P. aeruginosa (MIC ≥2%), all reference strains tested were susceptible to catnip and lemon balm oils with MIC values ranging from 0.016 % to 0.25% (v/v). The clinical isolates were as susceptible to the oils (± 1 serial dilution) as the corresponding reference strains, regardless of their origin and resistance to standard antibiotics. The oils were cytotoxic to both keratinocytes and bronchial epithelial cells at CC50 values from 0.0012% to 0.015% (v/v). Lemon balm oil, whose main components were monoterpene aldehydes, exhibited the highest antibacterial and cytotoxic activity, followed by lemon catnip oil, which contained mainly monoterpene alcohols, and catnip oil, which was characterized by nepetalactones. Our results provide a rationale for the use of catnip, lemon catnip and lemon balm oils in the complementary topical treatment of respiratory tract infections, as the oils show a high antibacterial activity against respiratory tract pathogens, including clinical isolates with reduced susceptibility to standard antibiotics. However, cytotoxicity must be considered in topical therapy.
Antifungal and Anti-insect Activities of Three Essential Oils on Aspergillus Flavus Link and Sitophilus Zeamais Motsch
Authors: Tatsadjieu Leopold N. , Ngassoum Martin B. , Nukenine Elias N. , Mbawala Augustin , Yaouba Aoudou
Published: March 2019

Combinations of equal volumes of essential oils of Ocimum gratissimum, Lippia rugosa and Xylopia aethiopica were studied for their inhibiting activity on the mycelial growth of Aspergillus flavus by the determination of the minimum inhibiting concentrations (MIC), and on Sitophilus zeamais by the determination of the LV50 (volume that kills 50% of insects) and LV90 (volume that kills 90% of insects) values. All the combinations led to an increase in the inhibition of the mycelial growth of A. flavus with a synergy between these oils. The interesting combination of O. gratissimum and L. rugosa increased the inhibition of the mycelial growth of A. flavus; the observed MIC (600 ppm) was significantly lower than that predicted (900 ppm). Concerning anti-insect activity, a slight reduction in the LV90 on S. zeamais was observed for the combination of the three oils. The binary combinations showed higher LV50 and LV90 values than those predicted. There was no synergistic anti-insect activity between the three essential oils.
Antifungal Activity of the Volatile Phase of Essential Oils: A Brief Review
Authors: Cavanagh Heather M. A.
Published: March 2019

Interest in the antifungal activity of essential oils has increased markedly in recent years. The volatile (vapour) components of several essential oils have been demonstrated to have potent antifungal activity, often in excess of that displayed in direct contact assays. A lack of consistent methodology and reporting, however, hinders direct comparison of publications. A variety of mechanisms have been suggested for the activity of these active volatiles against hyphate fungi. This paper briefly reviews some of the more recent data and identifies areas that require standardization and further study.
The Medicinal Use of Essential Oils and Their Components for Treating Lice and Mite Infestations
Authors: Williamson Elizabeth M.
Published: March 2019

Recent studies have demonstrated that essential oils, and in particular, pennyroyal, tea tree and anise, have potent insecticidal and acaricidal (mite-killing) activity. The individual components of essential oils are now being investigated in order to give a rational basis to discover which essential oils may prove to be the most effective all-round agents for killing headlice and their eggs, and treating scabies, and for eliminating house dust mites, a major cause of asthma.
A Review of Aromatic Herbal Plants of Medicinal Importance from Nigeria
Authors: Ogunwande Isiaka A. , Walker Tameka M. , Setzer William N.
Published: March 2019

Nigeria is blessed with a rich source of aromatic flora, many of which have not been previously investigated for their chemical constituents and biological potentials. This flora constitutes a rich source of potential spices or flavoring, ingredients of formulae intended for pharmaceutical administration, and for perfumery. Interestingly, essential oil constituents such as 1,8-cineole, precocene, 6,10,14-trimethylpentadecan-2-one, eugenol, β-caryophyllene, α-pinene, α-terpineol and even hitherto uncommon compounds such as zerumbone and rare terpenoid esters have been isolated and characterized from these plants. In addition, some of the studied volatile oils have exhibited biological activities of importance such as antimicrobial and cytotoxicity. The majority of these aromatic plants occur either as perennial or annual herbs which are suitable for cultivation purposes in herbal gardens, traditional medicinal centers, parks, research institutes and forest reserves. This paper presents a review of some of the endemic aromatic and medicinal plants of Nigeria with a view to ascertaining their suitability as raw materials for the pharmaceutical and perfumery applications.
COX-2 Inhibitory Activity of Cafestol and Analogs from Coffee Beans
Authors: Muhammad Ilias , Takamatsu Satoshi , Mustafa Jamal , Khan Shabana I. , Khan Ikhlas A. , Samoylenko Volodymyr , Mossa Jaber S. , El-Feraly Farouk S. , Dunbar D. Chuck
Published: March 2019

Two kaurane diterpenes, namely cafestol (1) and kahweol (2), were isolated from hydrolyzed fraction of the fixed oil of Ethiopian Coffea arabica unroasted beans, using AgNO3-impregnated silica gel chromatography. In addition, cafestol palmitate (3) and kahweol palmitate (4), the two natural diterpene esters of C. arabica, were also synthesized. Compounds 1–4 were evaluated for anti-inflammatory activity using cyclooxygenase-2 (COX-2), cell aggregation, cell proliferation, cell adhesion, iNOS and antioxidant assays. The COX-2 inhibitory activity of cafestol (1) was found to be 20-fold more potent than kahweol (2) (IC50 value 0.25 μg/mL vs. 5.0 μg/mL), while compounds 3 and 4 were weakly active. The isolation and structure elucidation of the diterpenes 1 and 2, preparation of compounds 3 and 4, and their biological activities are presented in this paper.
Boswellic Acids with Acetylcholinesterase Inhibitory Properties from Frankincense
Authors: Ota Masahiro , Houghton Peter J.
Published: March 2019

Frankincense, a gum resin secreted from barks of Boswellia species, is reputed in Arabian folk medicine to improve the memory. In this study, the acetylcholinesterase inhibitory effect of extracts of frankincense and their constituents were investigated. The ethyl acetate soluble fraction from methanol extracts showed the greatest inhibition of acetylcholinesterase. Bioassay-guided fractionation was carried out to isolate several boswellic acids, and their structures were determined spectroscopically. The boswellic acids showing the most inhibitory activity on acetylcholinesterase were 11α-hydroxy-β-boswellic acid (1) and 11-keto-β-boswellic acid (5), whilst others isolated i.e. 3α-acetyl-11-keto-β-boswellic acid (2), 3α-acetyl-11α-hydroxy-β-boswellic acid (3), 11α-methoxy-β-boswellic acid (4), β-boswellic acid (6) and α-boswellic acid (7) were inactive. Acetylcholinesterase inhibitory activity appears to be associated with the presence of either the free hydroxyl group or keto group at C-11 and of the free hydroxyl group at C-3 in the ursane skeleton.
Annona muricata (Graviola): Toxic or Therapeutic
Authors: Mohanty Sambeet , Hollinshead Jackie , Jones Laurence , Jones Paul Wyn , Thomas David , Watson Alison A. , Watson David G. , Gray Alexander I. , Molyneux Russell J. , Nash Robert J.
Published: March 2019

The medicinal plant Annona muricata (Annonaceae), also known as Graviola or Soursop, is reported here to contain imino sugar alkaloids. This is the first report of imino sugars in the Annonaceae. Graviola has very broad medicinal claims and is also widely consumed as a food and in drinks in the tropics. The plant produces a wide range of secondary chemicals, some already known to be toxic, but the discovery here of the imino sugars as a new group of chemicals, including the neurotoxin swainsonine, raises questions about the safety of consumption of this plant.
Selective Metabolism of Glycosidase Inhibitors by a Specialized Moth Feeding on Hyacinthoides non-scripta Flowers
Authors: Watson Alison A. , Winters Ana L. , Corbet Sarah A. , Tiley Catherine , Nash Robert J.
Published: March 2019

The British moth Eana incanana (Tortricidae) has been found to selectively metabolize the glycosidase inhibitor 2 R, 3 R, 4 R, 5 R-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP), whereas it excretes related alkaloids from Hyacinthoides non-scripta (Hyacinthaceae). Very few native animals feed on H. non-scripta, but the larvae of E. incanana are specialized herbivores feeding just on the buds and flowers destroying the ovary. DMDP is the major glucosidase inhibitor of H. non-scripta and the moth may overcome inhibition of digestive glucosidases by metabolizing the DMDP. The glucosidase enzymes of the caterpillar are inhibited by DMDP. The caterpillar excretes the other glycosidase inhibitors produced by this plant and the frass has increased concentrations of these alkaloids.
A Pyranochalcone and Prenylflavanones from Tephrosia pulcherrima (Baker) Drumm
Authors: Ganapaty Seru , Srilakshmi Guttula V. K. , Pannakal Steve T. , Laatsch Hartmut
Published: March 2019

A new 2′,6′-dimethoxy-4′,5′-(2″,2″-dimethyl)-pyranochalcone (1) and three known flavanones, namely 5-hydroxy-7-methoxy-8-(3,3-dimethylallyl)-flavanone (methyl glabranin) (2), 5,7-dimethoxy-8-(3,3-dimethylallyl)-flavanone (candinone) (3) and 5- O-methyl obovatin (pongachin) (4), have been isolated from the chloroform extract of the roots of Tephrosia pulcherrima. The flavonoids were fully characterized by detailed 1D- and 2D-NMR spectroscopic investigations. The pyranochalcone 1 showed significant antimicrobial activity when tested against a series of micro-organisms.
Bisresorcinols and Arbutin Derivatives from Grevillea banksii R. Br
Authors: Wang Hao , Leach David , Thomas Michael C. , Blanksby Stephen J. , Forster Paul I. , Waterman Peter G.
Published: March 2019

This work is part of a series of chemical investigations of the genus Grevillea. Two new arbutin derivatives, seven new bisresorcinols, including a mixture of two isomers, three known flavonol glycosides, and four known resorcinols, including a mixture of two homologous compounds, were isolated from the ethyl acetate extract of the leaves and methanol extract of the stems of Grevillea banksii. The new compounds were identified, on the basis of spectroscopic data, as 6′- O-(3-(2-(hydroxymethyl)acryloyloxy)-2-methylpropanoyl)arbutin (1), 6′- O-(2-methylacryloyl) arbutin (2), 5,5′-(4( Z)-dodecen-1,12-diyl)bisresorcinol (6), 2′-methyl-5,5′-(4( Z)-tetradecen-1,14-diyl)bisresorcinol (8), 2,2′-di(4-hydroxyprenyl)-5,5′-(6( Z)-tetradecen-1,14-diyl)bisresorcinol (9), 2-(4-acetoxyprenyl)-2′-(4-hydroxyprenyl) 5,5′-(6( Z)-tetradecen-1,14-diyl)bisresorcinol (10), 2-(4-acetoxyprenyl)-2′-(4-hydroxyprenyl)5,5′-(8( Z)-tetradecen-1,14-diyl)bisresorcinol (11), 5,5′-(10( Z)-tetradecen-1-on-diyl)bisresorcinol (12) and 5,5′-(4( Z)-tetradecen-1-on-diyl)bisresorcinol (13).
Non-Protein Amino Acids: A Review of the Biosynthesis and Taxonomic Significance
Authors: Bell E. Arthur , Watson Alison A. , Nash Robert J.
Published: March 2019

The non-protein amino acids, with which we are concerned here, are not incorporated into the proteins of the organisms that synthesize them nor are their residues formed by the post-translational modification of protein amino acid residues. Non-protein amino acids are of value in the study of relationships between species and higher taxa of organisms because most of them are of restricted distribution. If a particular non-protein amino acid is only known to occur in a limited group of species which are related in other respects then it is probable that these species have all arisen from a common ancestral form in which the biosynthetic pathway to that particular non-protein amino acid already existed.
Secondary Metabolites from Eremostachys Laciniata
Authors: Çalış İhsan , Güvenç Ayşegül , Armağan Metin , Koyuncu Mehmet , Gotfredsen Charlotte H. , Jensen Søren R.
Published: March 2019

From the aerial parts of Eremostachys laciniata (Lamiaceae), a new acidic iridoid glucoside, 5-desoxysesamosidic acid (1) was isolated in addition to thirteen known iridoid glucosides, 5-desoxysesamoside (2), sesamoside (3), 6β-hydroxy-7- epi-loganin (4), chlorotuberoside (5), 5-deoxypulchelloside I (6), lamalbide (7), lamalbidic acid (8), phloyosides I (7- epi-phlomiol) (9), and II (10), phlomiol (11), shanzhiside (12), shanzhiside methyl ester (13), and barlerin (8- O-acetylshanzhiside methyl ester) (14), four phenylethanoid glycosides, verbascoside (15), leucosceptoside A (16), martynoside (17), and forsythoside B (18), and five flavone derivatives, luteolin (19), luteolin 7- O-β-D-glucopyranoside (20), luteolin 7- O-(6″- O-β-D-apiofuranosyl)-β-D-glucopyranoside (21), apigenin 7- O-β-D-glucopyranoside (22), and apigenin 7- O-(6″- O-p-coumaroyl)-β-D-glucopyranoside (23). The structures of the metabolites were elucidated from spectroscopic (UV, IR, 1D- and 2D-NMR) and ESI-MS evidence, as well as from their specific optical rotations. The presence of these metabolites of three different classes strongly supports the close relationship of the genera Eremostachys and Phlomis.
A Novel Iridoid from Plumeria Obtusa
Authors: Ali Firdous Imran , Hashmi Imran Ali , Siddiqui Bina Shaheen
Published: March 2019

Phytochemical investigations of fresh leaves and stem bark of Plumeria obtusa Linn. have led to the isolation and characterization of a new iridoid, p-methoxy- E-cinnamoyloxy plumieride (1), to which the trivial name champalinin has been assigned, and a triterpene lactone, 3β-hydroxy-urs-12-one-13β,28-olide (2). This is the first report of compound 2 as a natural product, although it has been reported earlier as a synthetic compound. Identification of these compounds was achieved through spectroscopic studies and chemical transformations.