bluuebunny/crossref_metadata_2025 huggingface dataset:
Ganoderic Acid TR, a New Lanostanoid with 5α-Reductase Inhibitory Activity from the Fruiting Body of Ganoderma Lucidum
Authors: Liu Jie , Shimizu Kuniyoshi , Kondo Ryuichiro
Published: March 2019

By means of 5α-reductase inhibitory activity-guided fractionation, a new lanostanoid, 15α-hydroxy-3-oxolanosta- 7, 9(11), 24(E)-trien-26-oic acid, named as ganoderic acid TR, was isolated from the ethanol extract of the fruiting bodies of Ganoderma lucidum (Fr.) Karst (Ganodermataceae). The compound showed potent inhibitory activity with an IC50 of 8.5 μM. Modified Mosher's method established the S-configuration of the secondary hydroxyl group at C-15. In addition, a carboxyl group on the side chain of ganoderic acid TR is essential to elicit the inhibitory activity because of the considerably lower activity of its methyl ester.
Polyanxanthone, a Xanthone from the Stem Bark of Garcinia Polyantha
Authors: Komguem Justin , Lannang Alain M. , Tangmouo Jean G. , Louh Gabin N. , Ngounou Fernande N. , Lontsi David , Choudhary Muhammad I. , Sondengam Beiban L.
Published: March 2019

A new xanthone polyanxanthone, together with five known xanthones, a pentacyclic triterpene and a benzophenone were isolated from the stem bark of Garcinia polyantha.
Antioxidant Activity of Metabolites from Coleonema Album (Rutaceae)
Authors: Esterhuizen Lindy L. , Meyer Riaan , Dubery Ian A.
Published: March 2019

Coleonema album, a member of the South African ‘Fynbos’ biome, was evaluated for its antioxidant and free radical scavenging activity. Ethanol- and acetone-based extracts from plant material obtained from two different geographical areas were analysed. A bioassay-guided fractionation methodology was followed for screening of active compounds. The 1,1-diphenyl-2-picrylhydrazyl (DPPH)-TLC method revealed the presence of a number of antioxidants which were quantified by the DPPH-spectrophotometric assay and the oxygen radical absorbance capacity (ORAC) assay. The C. album extracts possessed significant in vitro antioxidant activity, a large portion of which appeared to be contributed by the phenolic compounds. In contrast, the reducing power of the extracts could not be correlated with the observed antioxidant activity. Identification and structural information of the active components were obtained by a combination of preparative TLC and LC-MS which revealed the presence of coumarin aglycones and glycosides. The results of this study indicate that C. album contains strong antioxidants that warrant further investigation into the relationship between the structure and activity of the active coumarin metabolites.
Volatile Constituents of Geranium Tuberosum L. from Iran
Authors: Barra Andrea , Norouzi-Arasi Hassan , Sedaghat-Sharehjini Sajjad , Baldovini Nicolas
Published: March 2019

The SDE extract of Geranium tuberosum L. from Iran was analysed by GC and GC/MS. A total of 93 compounds, representing 89.8% of the entire extract were identified. The composition was dominated by 3-methylbutanal (5.4%), furfural (5.3%), α-pinene (4.1%) and linalool (6.4%), as well as fragranol (4.4%) and fragranyl acetate (7.4%), two rare cyclobutane monoterpenoids never reported previously in the genus Geranium.
Influence of Roasting and Seed Collection on Argan Oil Odorant Composition
Authors: Charrouf Zoubida , Hamchi Halima El , Mallia Silvia , Licitra Giuseppe , Guillaume Dominique
Published: March 2019

Argan tree (Argania spinosa (L.) Skeels) is endemic in Morocco. The aroma compounds of argan oil prepared from roasted and unroasted argan kernels were analyzed using GC-MS and olfactometry. Influence of the fruit peeling method on the olfactometric parameters was also studied. Oil coming from unroasted kernels furnished fourteen compounds if the fruits had been mechanically-peeled fruits (uRK), and twenty two when the kernels had been goat digested (GuRK). Thirteen compounds were common to the two studies. The oil obtained from roasted kernels of mechanically-peeled fruits (RK) furnished nineteen compounds. Twenty one were isolated from the oil obtained from roasted kernels of goat digested fruits (GRK). Twelve compounds were common to the two analyses. In all oil samples, the aldehyde/ketone derivatives composed the largest group of odorants. Acetophenone and p-methylacetophenone appear to be the most important contributors to the RK oil aroma. The unpleasant smell presented by argan oil prepared from naturally-peeled argan fruits (GuRK, GRK) could result from the presence of one or two odorants presenting a rancid odor.
Galanthamine Content of Bulbs and in Vitro Cultures of Leucojum Aestivum L
Authors: Diop Mamadou F. , Ptak Agata , Chrétien Françoise , Henry Max , Chapleur Yves , Laurain-Mattar Dominique
Published: March 2019

In vitro cultures, at different stages of morphogenesis, were established from leaves of Leucojum aestivum (Amaryllidaceae) for determination of their galanthamine content, an alkaloid that possesses cholinesterase inhibitory activity and which is used for the treatment of Alzheimer's disease. A suitable HPLC method for qualitative and quantitative determination of galanthamine in both in vitro and in vivo extracts has been developed. Confirmation of the identity of galanthamine in sample extracts was achieved using LC-MS-MS. A correlation was observed between the state of differentiation and the galanthamine content of the tissue cultures. No galanthamine was detected in the roots grown in vitro, while all bulblets grown in vitro showed the presence of this alkaloid, with dramatic variations in concentration levels, according to the growth substance balance. The best result (6.79 × 10−3 % of D.W.) was obtained with bulblets initiated with NAA (10 μM) combined with BA (0.5 μM).
Chemical Evolution in the Asteraceae. The Oxidation– Reduction Mechanism and Production of Secondary Metabolites
Authors: Emerenciano Vicente P. , Cabrol-Bass D. , Ferreira Marcelo J. P. , Alvarenga Sandra A.V. , Brant Antonio J. C. , Scotti Marcus T. , Barbosa Karina O.
Published: March 2019

This work describes the application of partial least squares (PLS) regression to variables that represent the oxidation data of several types of secondary metabolite isolated from the family Asteraceae. The oxidation states were calculated for each carbon atom of the involved compounds after these had been matched with their biogenetic precursor. The states of oxidation variations were named oxidation steps. This methodology represents a new approach to inspect the oxidative changes in taxa. Partial least square (PLS) regression was used to inspect the relationships among terpenoids, coumarins, polyacetylenes, and flavonoids from a data base containing approximately 27,000 botanical entries. The results show an interdependence between the average oxidation states of each class of secondary metabolite at tribe and sub tribe levels.
Some Biological Properties of Curcumin: A Review
Authors: Ali Badreldin H. , Marrif Husnia , Noureldayem Salwa A. , Bakheit Amel O. , Blunden Gerald
Published: March 2019

Curcumin (diferuloyl methane), a small-molecular weight compound isolated from the roots of Curcuma longa L. (family Zingiberaceae), has been used traditionally for centuries in Asia for medicinal, culinary and other purposes. A large number of in vitro and in vivo studies in both animals and man have indicated that curcumin has strong antioxidant, anti-carcinogenic, anti-inflammatory, anti-angiogenic, antispasmodic, antimicrobial, anti-parasitic and other activities. The mechanisms of some of these actions have recently been intensively investigated. Curcumin inhibits the promotion/ progression stage of carcinogenesis by induction of apoptosis and the arrest of cancer cells in the S, G2/M cell cycle phase. The compound inhibits the activity of growth factor receptors. The anti-inflammatory properties of curcumin are mediated through their effects on cytokines, lipid mediators, eicosanoids and proteolytic enzymes. Curcumin scavenges the superoxide radical, hydrogen peroxide and nitric oxide, and inhibits lipid peroxidation. These actions may be the basis for many of its pharmacological and therapeutic properties.

Curcumin is a nutraceutical of low toxicity, which has been used successfully in a number of medical conditions that include cataracts, cystic fibrosis, and prostate and colon cancers.
Argolic Acid A and Argolic Methyl Ester B, Two New Cyclopentano-monoterpenes Diol from Nepeta Argolica
Authors: Ahmed Ahmed A. , Hassan Husaam E. , Hegazy Mohamed F. , Tzakou Olga , Couladis Maria , Mohamed Abou El-Hamed H. , Abdella Mohamed A. , Paré Paul
Published: March 2019

Two new cyclopentanomonoterpenes, argolic acid A (1) and argolic methyl ester B (2), in addition to four known compounds, were isolated from the aerial parts of Nepeta argolica subsp. argolica. The structures of the compounds were elucidated by one and two dimensional NMR spectroscopy.
Chemical Constituents of Gentiana Macrophylla Pall. From Shaanxi
Authors: Chen Qianliang , Sun Wenji , Tu Guangzhong , Shi Zhangyan , Zhang Yongmin
Published: March 2019

A novel amide, qinjiaoamide and a novel iridoid, erythrocentaurin acid, together with seven known compounds [erythrocentaurin (3), roburic acid (4), oleanolic acid (5), gentiopicroside (6), swertiamarine (7), sweroside (8), and 6′-O-β-D-glucosylgentiopicroside (9)], were isolated from the root of Gentiana macrophylla Pall. from Shaanxi Province, China. The novel compounds were identified as N-pentacosyl-2-carboxy-benzoyl amide (1) and 5-carboxyl-3,4-dihydrogen-1H-2-benzopyran-1-one (2), on the basis of spectroscopic (UV, IR, 1D- and 2D-NMR) and mass spectrometric data. Among the known compounds, erythrocentaurin (3) was isolated from the genus Gentiana for the first time.
Leishmanicidal, Antifungal, and Cytotoxic Activity of Triterpenoid Glycosides Isolated from the Sea Cucumber Neothyone Gibbosa
Authors: Encarnacion-Dimayuga Rosalba , Murillo-Álvarez Jesús Iván , Christophersen Carsten , Chan-Bacab Manuel , Reiriz María Luz García , Zacchino Susana
Published: March 2019

Neothyosides A - C, isolated from the body walls of the sea cucumber Neothyone gibbosa Deichmann, and a partially purified mixture of these saponins, were tested in vitro against promastigotes of two strains of Leishmania mexicana and a panel of several fungi using the broth microdilution technique. In addition, the cytotoxicity of these saponins was tested against Artemia salina. The IR, 1H and 13C NMR spectroscopic and FAB MS data of neothyoside C revealed that its structure was identical to that of pervicoside B, isolated from another sea cucumber species, Holothuria pervicax. Neothyoside C was the most active antiparasitic compound, inhibiting 100% of the promastigotes at 5 and 10 μg/mL of both L. mexicana strains. The mixture of saponins and pure neothyoside C showed the best activity against Aspergillus niger strains with MIC values between 15.6 μg/mL and 16.7 μg/mL for the mixture, and 4.65 μg/mL and 7.8 μg/mL for neothyoside C. Assays for cytotoxicity using Artemia salina showed that neothyosides A and C caused 50% brine-shrimp deaths at 130 and 63 μg/mL with this cytotoxicity 4 to 6 times greater than the concentration at which these compounds produce an antimicrobial effect. This is the first report describing the antileishmanial, antifungal, and cytotoxic activity of N. gibbosa saponins.
Isolation and Structure of Cordifolin, A Novel Insecticidal Oxygenated Chalcone, from the Stem of Tinospora Cordifolia Miers
Authors: Shakil Najam A. , Saxena Dinesh B.
Published: March 2019

Cordifolin, a chalcone reported for the first time from a natural source, has been isolated from the ethanolic extract of the woody stem of Giloe (Tinospora cordifolia). The chemical structure was established as 1-(2′,3′,4′-trihydroxyphenyl)-3-(4′‘-methoxyphenyl)-propen-1-one by spectroscopic analysis. The compound exhibited good insect growth regulatory activity against larvae of Spodoptera litura.
Chemical Compositions of the Bark Essential Oils of Croton Monteverdensis and Croton Niveus from Monteverde, Costa Rica
Authors: Setzer William N.
Published: March 2019

The essential oils of the barks of Croton monteverdensis Huft and C. niveus Jacq. (Euphorbiaceae) from Monteverde, Costa Rica, were isolated by hydrodistillation in yields of 0.03% and 0.10%, respectively. The chemical composition of the oils was determined by GC–MS. The most abundant essential oil components of C. monteverdensis were α-pinene (17.1%), β-pinene (10.5%), and linalool (8.3%), while C. niveus bark oil was made up largely of α-pinene (14.4%), 1,8-cineole (11.6%), and borneol (8.5%). The major components account for the fragrances and are consistent with the traditional medicinal uses of these plants.
The Diterpenoids of the Genus Marrubium (Lamiaceae)
Authors: Piozzi Franco , Bruno Maurizio , Rosselli Sergio , Maggio Antonella
Published: March 2019

The occurrence and chemical structures of labdane diterpenoids from the genus Marrubium are reviewed and the published 13C NMR spectroscopic data for these compounds is presented. The pharmacological activities and biogenesis of these diterpenoids are also reported.
Diterpenoid Constituents from the Brown Alga Dictyota Menstrualis (Dictyotaceae, Phaeophyta)
Authors: Cavalcanti Diana N. , Rezende Claudia M. , Pinto Angelo C. , Teixeira Valéria L.
Published: March 2019

The acetone extract of the Brazilian brown alga Dictyota menstrualis (Hoyt) Schnetter, Hörnig & Weber-Peukert was analyzed by HRGC-MS. Eight diterpenoids were identified: pachydictyol A (1), isopachydictyol A (2), dictyol C (3), dictyotadiol (4), dictyoxide (5), 9-hydroxy- and 9-acetoxy-dichotoma-2, 13-diene-16,17-dial (6–7) and 5-hydroxy-1, 6-cycloxenia-2,13-diene-16,17-dial (8). This technique may be an excellent alternative for chemotaxonomic and biogeographic studies.
Flavonoids from Rosa Damascena Mill.
Authors: Kumar Neeraj , Singh Bikram , Kaul Vijay K
Published: March 2019

A new flavanone glycoside, butin 4′-O-(2″-O-β-D-apiofuranosyl)-β-D-glucopyranoside (1), together with liquiritin (2), liquiritin apioside (3), isoliquiritn apioside (4), davidioside (5), quercetin (6), kaempferol (7), kaempferol 3-O-β-D-glucopyranoside (8) and kaempferol 3-O-α-L-arabinofuranoside (9) were isolated from the marc of Rosa damascena flowers after industrial distillation of essential oil. This is the first report of the occurrence of compounds 2, 3, 4 and 5 in R. damascena. The structures of the isolated constituents were established on the basis of spectroscopic {UV, IR, 1D, 2D NMR (DEPT, HMQC, HMBC and COSY)}, spectrometric (ESI-QTOF-MS), and chemical evidence.
Bioactivity of Hirsutanolol, Oregonin and Genkwanin, Isolated from the Seeds of Alnus Glutinosa (Betulaceae)
Authors: Kumarasamy Yashodharan , Cox Philip J. , Jaspars Marcel , Nahar Lutfun , Sarker Satyajit D.
Published: March 2019

The antibacterial and free radical scavenging activity, and the general toxicity of two diarylheptanoids, hirsutanolol (1) and oregonin (2), and a flavonoid, genkwanin (3), isolated from the methanol extract of the seeds of Alnus glutinosa, were assessed by the 96 well-based serial dilution antibacterial assay using resazurin as an indicator of cell growth, the DPPH assay, and the brine shrimp lethality assay, respectively.
Chemical Composition and Antimicrobial Activity of the Essential Oil of Saccocalyx satureioides Coss. et Dur
Authors: Laouer Hocine , Akkal Salah , Debarnot Claire , Canard Bruno , Meierhenrich Uwe J. , Baldovini Nicolas
Published: March 2019

The chemical composition of the essential oil of Saccocalyx satureioides Coss. et Dur. (Lamiaceae) was analyzed by chiral and achiral GC/MS and 42 components were identified. The main constituents were (+)-α-terpineol (35.9%), thymol (15.6%) and borneol (12.4%). The in vitro antibacterial and antifungal activities of the essential oil were assessed by the disc diffusion method, and were significant on the six microorganisms tested. A moderate inhibitory activity against hepatitis C virus polymerase was also evidenced.
Novel Lapachol Derivatives and Their Antioxidant Activity
Authors: Wenceslau João P. S. , de Souza Dávila F. , de Oliveira Maria C. F. , Lemos Telma L. G. , de Sousa Antonia L. , Trevisan Maria T. S. , de Mattos Marcos C.
Published: March 2019

A convenient synthesis of the new enamine derivatives 2-diethylamino-3-(3-methyl-2-butenyl)-1,4-naphthalenedione (2), 2-ethylamino-3-(3-methyl-2-butenyl)-1,4-naphthalenedione (3), 2-diethanolamino-3-(3-methyl-2-butenyl)-1,4-naphthalenedione (4), and 2-(1-piperazinyl)-3-(3-methyl-2-butenyl)-1,4-naphthalenedione (5) was carried out from natural 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphtalenedione (lapachol, 1) and diethylamine, ethylamine, diethanolamine and piperazine, respectively. All products were fully characterized by IR, 1H and 13C NMR spectroscopy. Results revealed no antioxidant behavior for 1 and enamines 2 and 3, but antioxidant activity for enamines 4 and 5.
A New Ionone Glucoside and Terpenoid Constituents from Achillea biebersteinii and their Antifungal Activity
Authors: Mahmoud Ahmed A. , Al-Shihry Shar S.
Published: March 2019

A new ionone glucoside, (-)(4R*, 5R*)-5-(β-D-glucopyranosyloxymethyl)-4-hydroxy-3,5-dimethyl-4-((E)-3-oxobut-1-enyl)cyclohex-2-enone (biebersteiniside) (1), in addition to four known compounds, 6-epiroseoside (2), ascaridole (3), strictic acid (4) and centipedic acid (5) have been isolated from the aerial parts of Achillea biebersteinii Afan. The structures were determined from extensive 500 MHz NMR 1D (1H and 13C NMR) and 2D (1H-1H COSY, HMQC, HMBC and NOESY) spectroscopic data. Compounds 2–5 are reported for the first time from this plant. In addition, compounds 1a and 3–5 showed antifungal activity.
Smooth Muscle Relaxant Triterpenoid Glycosides from Rubus idaeus (Raspberry) Leaves
Authors: Vera Janne Rojas , Dacke Christopher G. , Blunden Gerald , Patel Asmita V.
Published: March 2019

A methanol extract of Rubus idaeus leaves had a relaxant activity on transmurally stimulated Guinea pig ileum preparations in vitro. The extract, when fractionated by column chromatography, yielded two distinct bands with pharmacological activity. After extensive column and preparative TLC separation, several compounds with smooth muscle relaxant properties were obtained. From band two, three triterpenoid glycosides were characterized, which had significant muscle relaxant activity. From spectroscopic and spectrometric data, these were identified as 3β-(O-β-D-glucopyranosyl)-olean-12-ene-1α, 2α, 3β-triol (TG1); 28-(O-β-D-glucopyranosyl)-urs-12-ene-2α, 3β, 19α-trihydroxy-28-oic acid (TG2); and 3β-(O-β-D-glucopyranosyl)-olean-12-ene-1α, 2α, 3β-trihydroxy-28-oic acid (TG3). To the best of our knowledge, TG1 and TG3 are novel compounds.
Occurrence in Kava Roots of Kava Lactone-Yielding Precursor(s)
Authors: Naiker Mani , Prasad Sunny Y , Singh Ranjeeta D. , Singh Joslin A. , Voro Tevita N.
Published: March 2019

This investigation has shown that the highly biologically active kava lactones, specifically those of desmethoxyyangonin, yangonin and kavain, exist in “locked-up” reserve forms. These important lactones can be regenerated from the totally delactoned polar residues when subjected to reflux at various pHs. The percentage of desmethoxyyangonin, yangonin and kavain regenerated from the same quantity of delactoned residue differed with the pH of the solution. Furthermore, treatment of the delactoned residue with β-D-glucosidase enzyme regenerated desmethoxyyangonin, yangonin and kavain in a pattern similar to that obtained under reflux at pH 5 and 8. These observations, when taken together with the outcome of the control experiment, suggest the presence of sugar bound kava lactone precursors in the delactoned residue.
Phenolics and Iridoids of Lippia Alba
Authors: Hennebelle Thierry , Sahpaz Sevser , Joseph Henry , Bailleul François
Published: March 2019

The phytochemical investigation of polar extracts of Lippia alba led to the isolation of a new acetylated flavonoid, apigenin-7-O-[(3-O-acetyl)β-D-glucopyranuronyl(1→2)]-β-D-glucopyranuronide, and of seventeen known compounds: seven iridoids (theveside, geniposidic acid, shanzhiside methyl ester, caryoptoside, 8-epi-loganin, mussaenoside and geniposide), six phenylpropanoids (cistanoside F, forsythoside B, calceolarioside E, acteoside, isoacteoside and 2-acetylacteoside) and four flavonoids (apigenin-7-O-glucuronide, luteolin-7-O-glucuronide, apigenin-7-O-diglucuronide and luteolin-7-O-diglucuronide).
Flavonoid and Flavone C-Glycosides from Dregea volubilis
Authors: Panda Nilendu , Mandal Debayan , Mandal Nirup B. , Sahu Niranjan P. , Banerjee Sukdeb
Published: March 2019

A new acylated flavone C-glycoside, dregeanin (1) was isolated from the flowers of Dregea volubilis, together with vicenin-2, vitexin, isovitexin, isoorientin, rutin, quercetin, luteolin and apigenin. The structure of 1 was established by spectroscopic analysis as apigenin-{6-C-β-D-glucosyl 2″-O-feruloyl}8-C-β-D-glucopyranoside.
Characterization of Seed Oil Components from Nephelium Lappaceum L
Authors: Avato Pinarosa , Rosito Isabella , Papadia Paride , Fanizzi Francesco P.
Published: March 2019

The chemical composition of the oil extracted from the seeds of Nephelium lappaceum L., commonly known as rambutan, has been investigated. The oil from this plant, similar to other members of the Sapindaceae, typically contained triglycerides (83%) and cyanolipids (17%). The latter consisted of type III cyanolipids, 1-cyano-2-hydroxymethylprop-1-en-3-ol diesters. Structural investigation of the oil components was carried out using chemical, chromatographic and spectroscopic methods. Oleic and arachidic acids were the two dominant esterified fatty acyl chains in both triglycerides and cyanolipids. Eicosenoic acids (cis-vaccenic and paullinic acid) were present in higher amounts in the cyanolipid fraction of the oil.
Volatile Constituents of Ficus Exasperata Leaves
Authors: Sonibare Mubo A. , Ogunwande Isiaka A. , Walker Tameka M. , Setzer William N. , Soladoye Mike O. , Essien Emmanuel
Published: March 2019

The composition of the volatile leaf oil of Ficus exasperata Vahl (Moraceae) is reported. The oil was obtained by hydrodistillation and analyzed for its constituents by means of gas chromatography-mass spectrometry (GC-MS). The oil is comprised of terpenoids and aliphatic compounds. The quantitatively significant compounds were 1,8-cineole (13.8%), (E)-phytol (13.7%) and p-cymene (11.4%). In addition, all other compounds were present above 2%. The oil shows no antibacterial activity against the tested organisms (MIC 625ppm).
Acetylenic Aquatic Anticancer Agents and Related Compounds
Authors: Dembitsky Valery M , Levitsky Dmitri O , Gloriozova Tatyana A , Poroikov Vladimir V
Published: March 2019

Although acetylenes are common as components of terrestrial plants, it is only within the last 30 years that biologically active polyacetylenes having unusual structural features have been reported from aquatic organisms: cyanobacteria, algae, fungi, invertebrates, and other sources. Naturally occurring aquatic acetylenes are of particular interest since many of them display important biological activities and possess antitumor, antibacterial, antimicrobial, antifouling, antifungal, pesticidal, phototoxic, HIV inhibitory, and immuno-suppressive properties. There is no doubt that they are of great interest, especially for the medicinal and/or pharmaceutical industries. This review presents structures and describes cytotoxic and anticancer activities of more than 230 acetylenic metabolites isolated from aquatic organisms. With the computer program PASS some additional biological activities are also predicted, which point toward possible new applications of these compounds. This review emphasizes the role of aquatic acetylenic compounds as an important source of leads for drug discovery.
N-Demethylation of Alkaloids
Authors: Thavaneswaran Shanti , McCamley Kristy , Scammells Peter J.
Published: March 2019

The removal of an N-methyl group, or N-demethylation, is a useful chemical transformation in organic synthesis which has particular importance in the field of alkaloid chemistry. Historically, tertiary N-methyl alkaloids have been N-demethylated using the same methods as for N-dealkylating tertiary amines. Such methodologies have included the von Braun reaction, the use of chloroformate and azodicarboxylate reagents and the Polonovski reaction, amongst others. Photochemical and biochemical procedures have also been successfully employed. This review will examine these N-demethylation procedures, with special emphasis on their application to opiate alkaloids.
5-Deoxynevadensin, a Novel Flavone in Sunflower and Aspects of Biosynthesis during Trichome Development
Authors: Göpfert Jens , Conrad Jürgen , Spring Otmar
Published: March 2019

Fluorescent microscopy of sunflower glandular trichomes from anther appendages showed a strong autofluorescence, caused by flavonoids. Chemical analysis with NMR and HRMS lead to the identification of 7-hydroxy-6,8,4′-trimethoxyflavone, a novel 5-deoxyflavone, exclusively found in capitate glandular trichomes. 5-Deoxy flavones are rarely found in Asteraceae and this is the first report for the genus Helianthus. Semiquantitative RT-PCR showed the presence of transcripts for phenylalanine ammonia lyase (PAL) and chalcone synthase (CHS) in all biosynthetically active trichome stages. PAL and CHS are key steps in flavonoid biosynthesis indicating that flavonoid production occurs directly within the trichomes. This offers the possibility for examination of 5-deoxyflavone biosynthesis within Asteraceae.
Flavonol Triglycosides from the Leaves of Silphium Albiflorum
Authors: Wojcińska Małgorzata , Williams Jeffrey , Mabry Tom J. , Ahmed Ahmed A. , Davis Barry D. , Tóth Gabor , El-Sayed Nabil H. , Matławska Irena , Clevinger Jennifer
Published: March 2019

In the course of chemotaxonomic studies of the genus Silphium two new and six known flavonol glycosides were isolated from the leaves of S. albiflorum. The structures of the new flavonoids were established by spectral analysis (1H NMR, 13C NMR, HMQC, HMBC, ROESY, TOCSY, MS) as isorhamnetin 3-O-α-L-rhamnosyl (1′“→6″)-O-β-D-galactopyranoside 7-O-β-D-apiofuranoside (1) and quercetin 3-O-α-L-rhamnosyl (1′“→6″)-O-β-D-galactopyranoside 7-O-β-D-apiofuranoside (2). LC-MS and LC-MSn (with post-column manganese complexation) were applied to elucidate the structures of some of the studied compounds.
Antitumor and Immunostimulatory Activity of Two Chromones and Other Constituents from Cassia Petersiana
Authors: Djemgou Pierre C. , Gatsing Donatien , Tchuendem Marguérite , Ngadjui Bonaventure T. , Tane Pierre , Ahmed Ahmed A. , Gamal-Eldeen Amira M. , Adoga Godwin I. , Hirata Toshifumi , Mabry Tom J.
Published: March 2019

Phytochemical and biological investigation of the leaves of Cassia petersiana afforded two new chromones (1, 2), in addition, to the known glyceryl-1-hexacosanoate (3) and stigmasterol-3-O-β-D-glucoside (4). The structures of the compounds were determined by comprehensive NMR studies, including DEPT, COSY, HMQC, HMBC and IR spectroscopy and MS. 1–4 were investigated against different types of cell lines, including solid tumor cells (Hep-G2, and MCF-7 cells) and leukemia (1301) cells for their cytotoxic effects. 1–3 possessed a dose-dependent cytotoxic effect against Hep-G2 cells, but in relatively high concentrations; 4 was the most cytotoxic with the lowest IC50 value of 82.7 μM. The calculated IC50 values against MCF-7 cells were 112.2 μM, 143.7 μM, 68.1 μM, and 114.3 μM for 1, 2, 3, and 4, respectively. The alteration in the macrophage proliferation index, using Raw 264.7 cells, was monitored. 1 and 3 were the highest stimulators of macrophage proliferation in a dose-dependent manner, whereas 2 and 4 showed a peak point of stimulation at 20 μM. The effect of these compounds on pre-induced NO was explored. 1–4 inhibited the LPS-induced NO, with inhibition percentages of 80.5%, 89.3%, 82.1%, and 92.1%, respectively, at a concentration of 20 μM. The antioxidant capacity of 1–4, using the DPPH assay was also investigated. 1–3 possessed weak scavenging activity; while 4 had an effective SC50 value as low as 36 μM. These results indicated that 4 possessed the highest anti-tumor, immunoproliferative, macrophage proliferation, anti-inflammatory, and antioxidant activities.
New Insight into the Ring Contraction of 2′-Benzyloxyflavanones
Authors: Németh István , Gulácsi Katalin , Antus Sándor , Kéki Sándor , Zsuga Miklós
Published: March 2019

The reactions of 2′-benzyloxyflavanones 9b,c with thallium(III) nitrate or iodobenzene diacetate in the presence of perchloric or sulfuric acid in trimethyl orthoformate was studied. Depending on the substitution pattern and the conditions, these compounds underwent 2-aryl migration (9b → 11a) and/or ring contraction (9c → 10b + 11b) and dehydrogenation (9c → 12). A probable mechanism of these transformations is discussed.
Antibacterial Activity and Irritation Potential of Selected Essential Oil Components – Structure-Activity Relationship
Authors: Reichling Jürgen , Suschke Ulrike , Schneele Jürgen , Geiss Heinrich Konrad
Published: March 2019

A selection of structurally diverse components of essential oils was subjected to an antibacterial screening against the Gram-positive bacteria Staphylococcus aureus and Streptococcus pneumoniae as well as the Gram-negative bacteria Escherichia coli and Haemophilus influenzae using a broth microdilution method. In addition, the irritation potential of these substances to mucous membranes was evaluated by a modified HET-CAM (Hen's Egg Test-Chorioallantoic Membrane) assay. Minimum inhibitory concentrations (MIC) and irritation threshold concentrations (ITC) were compared in order to identify substances with a low mucous membrane irritation potential at the antibacterially effective concentration. Regarding the antibacterial activity, the most active substances were cinnamaldehyde, phenols, monoterpene alcohols and aldehydes. Oxygenated monoterpenes and phenylpropanoids without either alcohol or aldehyde function (ethers, ketones) showed moderate activity. Mono- and sesquiterpene hydrocarbons, as well as sesquiterpene alcohols, were more or less inactive against most of the bacteria tested, with the exception of Streptococcus pneumoniae whose growth was inhibited by sesquiterpenes at exceptionally low concentrations. In most cases, the irritation potential of the test compounds could also be traced back to their structural features. 2-Phenylethanol, monoterpene alcohols, phenols and aromatic aldehydes had the lowest ITC-values, followed by monoterpene aldehydes, ketones and ethers. In contrast, monoterpene hydrocarbons caused irritation only at higher doses. Of special interest was the fact that all the sesquiterpenes tested were not irritant even when applied undiluted to the chorioallantoic membrane (CAM).
Nutritional Relevance of Flavonoids in Disease Prevention
Authors: Kyle Janet , Duthie Garry
Published: March 2019

Flavonoids are not essential nutrients in that their absence from the diet does not produce deficiency conditions in animals and man. However, many have important similarities to pharmacological agents used in the treatment of disease. Their role as dietary components in disease prevention is less clear. Many potentially anti-carcinogenic and anti-atherogenic effects observed in cell cultures will not be of nutritional relevance unless flavonoids gain access to appropriate cellular sites. The bioavailability of flavonoids will depend on numerous factors including molecular structure, the amount consumed, the food matrix, degree of bioconversion in the gut and tissues, the nutrient status of the host and genetic factors. Moreover, extensive and rapid intestinal and hepatic metabolism of flavonoids suggests that the body may treat them as xenobiotic and potentially toxic compounds requiring rapid elimination. Consequently, in addition to potential health benefits, possible adverse effects of flavonoids in the diet also need to be considered when assessing their roles in the prevention of degenerative diseases.
Plant Epicuticular Waxes: Chemistry, Form, Self-Assembly and Function
Authors: Koch Kerstin , Barthlott Wilhelm
Published: March 2019

Plant epicuticular waxes represent the outermost boundary layer of the majority of land plants. Based on their micromorphology and chemical composition they form a multifunctional surface. Their most important functions are the protection against uncontrolled water loss, reflection of solar radiation from UV to visible light, and their crucial influence on surface wettability and particle adhesion. The three-dimensional epicuticular wax crystals are of particular importance for the majority of these interfacial interactions. This article provides an overview on plant epicuticular waxes, focusing on chemical composition, morphology, self-assembly and function. It is dedicated to Prof. Dr. Eckhard Wollenweber on the occasion of his 65th birthday, and his continuous and fundamental work on a special class of plant secondary metabolites that are collectively called flavonoids.
Triterpenes from Maytenus macrocarpa and Evaluation of Their Anti-HIV Activity
Authors: Piacente Sonia , Santos Lourdes Campaner Dos , Mahmood Naheed , Pizza Cosimo
Published: March 2019

A set of pentacyclic triterpenes has been isolated from the bark of Maytenus macrocarpa (Celastraceae). It includes two new olean-12-ene derivatives, namely 3β, 22α-dihydroxy-olean-12-en-30-oic acid (1) and 22α-hydroxy-olean-12-en-3-oxo-30-oic acid (2), and the new urs-12-ene derivative 3-(E)-coumaroyluvaol (7), along with 10 known compounds possessing olean-12-ene, urs-12-ene, lupane and friedelane skeletons. The structures have been elucidated by extensive spectroscopic methods including 1D- and 2D-NMR experiments, as well as ESI-MS analysis. All isolated compounds were tested for anti-HIV activity in C8166 cells infected with HIV-1MN. The most active compound was 22α-hydroxy-12-en-3-oxo-29-oic acid (triterpenonic acid A, 4), with an EC50 value of 1 μg/mL and a selectivity index of 35.
New Oxidized 4-Oxo Fatty Acids from Hygrophorus Discoxanthus
Authors: Gilardoni Gianluca , Clericuzio Marco , Marchetti Alberto , Finzi Paola Vita , Zanoni Giuseppe , Vidari Giovanni
Published: March 2019

The results are reported from the first investigation of the secondary metabolites of the basidiomycete Hygrophorus discoxanthus (Fr.) Rea. Five new oxidized 4-oxo fatty acids (C16, C18) were isolated from the fruiting bodies and their structures established on the basis of their spectroscopic data and an ozonolysis experiment. Preliminary data indicate a moderate fungicidal activity, suggesting a possible function of these acids as chemical deterrents against mushroom parasites and predators.
Kenyaloside, a Novel O,O,O-Triglycosylated Naphthalene Derivative from the Exudate of Kenyan Aloe Species
Authors: Speranza Giovanna , Monti Daniela , Crippa Sergio , Cairoli Paola , Morelli Carlo F. , Manitto Paolo
Published: March 2019

A new naphthalene O,O,O-triglycoside, kenyaloside (1), was isolated from the dried exudate of Kenyan Aloe species, a bittering and laxative agent. Its structure was established by combined spectral and chemical methods as 1-(β-D-glucopyranosyloxy)-8-(α-L-rhamnopyranosyloxy)-3-(β-D-xylopyranosyloxymethyl)naphthalene.
N1,N2,N3-Trisisopentenyl Guanidine and N1,N2-Diisopentenyl Guanidine, Two Cytotoxic Alkaloids from Alchornea Cordifolia (Schumach. & Thonn.) Müll. Arg. (Euphorbiaceae) Root Barks
Authors: Mavar-Manga Hélène , Chapon David , Hoet Sara , Block Sébastien , De Pauw-Gillet Marie-Claire , Quetin-Leclercq Joëlle
Published: March 2019

This paper describes the purification of two guanidine alkaloids: N1, N2-diisopentenyl guanidine (DIPG) 1 and N1,N2,N3-triisopentenyl guanidine (TIPG) 2 from Alchornea cordifolia root bark and reports their cytotoxic properties on cancer (HeLa, Mel-5, J774) and non cancer (WI 38) cells. TIPG showed the highest cytotoxicity with IC50 values from 0.7 to 14.3 μg/mL (2.6 to 54.3 μM) on the four cell lines while DIPG was much less active: IC50 45.8 and 97.6 μg/mL (234.8 and 500.5 μM) on Mel-5 and HeLa and > 512.8 μM on J774 and WI 38. The results indicate that the cytotoxicity notably decreased with the loss of one isopentenyl substituent.
Indole Monoterpenes with Antichemotactic Activity from Psychotria myriantha: Chemotaxonomic Significance
Authors: Simões-Pires Cláudia A. , Farias Fabianne M. , Marston Andrew , Queiroz Emerson F. , Chaves Célia G. , Henriques Amélia T. , Hostettmann Kurt
Published: March 2019

The alkaloid extract of the aerial parts of Psychotria myriantha (Rubiaceae) displayed antichemotactic activity on polymorphonuclear leukocytes (PMN) assessed by the Boyden chamber assay. On analysis of the crude extract by LC/APCI/MS and LC/UV/DAD, two major constituents could be detected. In order to rapidly identify the active compounds, a microfractionation was conducted during LC/UV/DAD analysis. By this means, both the collected compounds could be assayed separately in the Boyden chamber and were shown to inhibit PMN chemotaxis. Their isolation was performed by semi-preparative HPLC and their structures elucidated by classical spectroscopic methods, including UV, NMR, MS and HRMS. Both compounds showed characteristics of monoterpene indole glucoside alkaloids; one of them was identified as strictosidinic acid and the other was a new natural product, myrianthosine. The antichemotactic activity of the compounds may be related to an antiacute inflammation activity.
HPLC Based Activity Profiling for Inhibitors of Human Neutrophil Elastase in Isatis tinctoria Leaf Extracts
Authors: Hamburger Matthias , Rüster Georg-Ulrich , Melzig Matthias F.
Published: March 2019

In continuation of our search for anti-inflammatory constituents in lipophilic extracts of Isatis tinctoria, an HPLC-based profiling for inhibitors of human neutrophil elastase was performed. Using a linear gradient profile, fractions with significant activity (>50%) appeared in the second half of the chromatogram and corresponded to moderately to highly lipophilic constituents. The active fractions of intermediate polarity were further analyzed by HPLC, TLC and GC. They contained mainly α-linolenic, linoleic, cis-11-octadecenoic acid, oleic and palmitic acids.
Antifungal Evaluation of Hypericum Triquetrifolium Polar Extracts against Fusarium spp
Authors: Fraternale Daniele , Bertoli Alessandra , Giamperi Laura , Bucchini Anahi , Ricci Donata , Menichini Francesco , Trinciarelli Elena , Pistelli Luisa
Published: March 2019

The chemical composition of different kinds of Hypericum triquetrifolium extracts was analyzed by LC-DAD-ESI-MS. Hyperoside, rutin, isoquercitrin and biapigenin were the main constituents. As these natural compounds were reported in the literature for their antifungal activity, the total extracts were tested for their antifungal activity against eight phytopathogenic strains of Fusarium species.
Antioxidant Activity Analysis for the Selection of Rosmarinus officinalis L
Authors: Garbarino Juan Antonio , Troncoso Nicolás , Delpiano Pia , Carvajal Loreto , Russo Alessandra
Published: March 2019

Rosmarinus officinalis L. presents a high genetic variability, which is reflected in the chemical composition of the different individuals, and consequently in its biological activity, including antioxidant capacity. The aim of the present research was to correlate the chemical composition of methanolic extracts of the dried leaves of eight rosemary accessions with their antioxidant activity for the selection of plants to optimize the use of rosemary. The eight samples examined, starting from a collection of more than 160 individuals selected by BOTANE Ltd, were cultivated at Illapel, north central Chile, using the same cultivation techniques. The free radical-scavenging capacity was tested by the ability of extracts to bleach the stable 1,1-diphenyl-2-picryl-hydrazyl radical (DPPH) and to inhibit superoxide anion (O2-) and hydroxyl radical (.OH) production. The metal chelating activity was estimated by the ferrozine assay. All extracts (1–8) contained high concentrations of carnosic acid, and to a minor extent rosmarinic acid, and exhibited antioxidant activity. However, extracts 7 and 8, containing 31.7 and 26.1% of carnosic acid, respectively, have shown a higher biological effect, confirming that the antioxidant activity of R. officinalis leaves is primarily related to this phenolic diterpene and suggesting that the measure of antioxidant activity could be considered a good method in the selection of this plant for its optimization. Interestingly, our experimental evidence also suggests that air pollution negatively influences the carnosic acid content. In fact, samples 3 and 4, with a low carnosic acid content, originated from a highly polluted metropolitan area of Santiago city.
Chemical Composition and Antimicrobial Activities of Essential Oil of Stachys Glutinosa L. from Sardinia
Authors: Giorgio Pintore , Mario Chessa , Paola Manconi , Stefania Zanetti , Antonella Deriu , Bruno Tirillini
Published: March 2019

The oil composition of Stachys glutinosa L. from two different areas of Sardinia was analyzed by GC/MS. The oil from Gallura plants was characterized by the four main constituents: terpinen-4-ol (12.7%), α-terpinyl acetate (10.6%), trans-cadina-1(6),4-diene (8.5%), and α-terpineol (8.4%) whilst α-cedrene (19.2%), α-terpineol (18.5%), terpinen-4-ol (12.6%), and α-terpinyl acetate (8.6%) were the main compounds in the oil from Ulassai plants. The oils showed good bacteriostatic activities against Vibrio cholerae (MIC 0.6%), all the Candida tested (1.25%) and Rodotorula rubra (2.5%). There were also bactericidal activities against Candida glabrata (1.25 %) and Rodotorula rubra (2.5%).
Acaricides of Natural Origin. Part 2. Review of the Literature (2002–2006)
Authors: Flamini Guido
Published: March 2019

Acari are responsible for millions of dollars worth of damage each year as a result of infestations of animals, plants and man. They directly affect our health and prosperity as animal and plant parasites, vectors of disease, and producers of allergens. The indiscriminate use of pesticides has quickly induced resistance in many parasites. At present, the control of acarid parasitic diseases in agriculture, human and veterinary medicine is mainly based on the use of drugs; and for this reason the lack of effective drugs often prevents the control of some parasitic diseases, making them more serious and important. The use of commercial drugs involves many problems, besides the drug-resistance shown by the most important parasites. Environmental damage and the toxicity of many synthetic drugs, represent the main problems that strongly limit drug use. In addition, drug residues in plant and animal food products are important reasons for further economic losses for farmers and must be regarded as potentially hazardous to man and the environment. Plant-derived compounds are generally more easily degradable and could show a smaller negative environmental impact with respect to synthetic drugs. For these reasons, the evaluation of the antiacarid activity of plant extracts is increasingly being investigated in order to obtain new leads, as demonstrated by recent studies that have evaluated and confirmed the effectiveness of many plant compounds on bacteria, fungi, protozoa, helminths and arthropods. This review will be limited to the class Arachnida, sub-class Acaridi, particularly to their control in agriculture, veterinary and human medicine using natural methods.
Chemical and Biological Activity of Triterpene Saponins from Medicago Species
Authors: Tava Aldo , Avato Pinarosa
Published: March 2019

Naturally occurring saponins are a large group of triterpene and steroid glycosides characterized by several biological and pharmacological properties. The Medicago genus represents a valuable source of saponins which have been extensively investigated. This review summarizes the chemical features of saponins from Medicago species and their biological activity, with particular attention to their antimicrobial, insecticidal, allelopathic and cytotoxic effects. Influence of saponins on animal metabolism is also reported.
Chemical Variation in the Diterpenes from the Brazilian Brown Alga Dictyota Mertensii (Dictyotaceae, Phaeophyta)
Authors: Freitas Odinéia do Socorro Pamplona , de Oliveira Aline Santos , De-Paula Joel Campos , Pereira Renato Crespo , Cavalcanti Diana Negrão , Teixeira Valéria Laneuville
Published: March 2019

Crude extracts of specimens from five populations of the Brazilian brown seaweed Dictyota mertensii (Martius) Kützing were analysed by HRGC-MS. A total of seven diterpenoids were identified: pachydictyol A (1), isopachydictyol A (2), dictyol B and its natural acetate (3–4), dictyoxide (5), dictyol C (6), dictyol H (7), and fucosterol (8), the last being the most abundant metabolite in four of the extracts. The results confirm that small-scale local variability in the chemicals found in D. mertensii probably is more significant than the overall latitudinal differences commonly observed in some marine organisms.
Analysis and Antiproliferative Activity of Bark Extractives of Betula Neoalaskana and B. Papyrifera. Synthesis of the Most Active Extractive Component - Betulin 3-Caffeate
Authors: Kolomitsyn Igor V. , Holy Jon , Perkins Edward , Krasutsky Pavel A.
Published: March 2019

The chemical content of outer birch bark extractive from the North American birches Betula papyrifera Marshall (paper birch) and B. neoalaskana Sargent (Alaskan paper birch) has been evaluated by GC/MS, HPLC and NMR spectroscopy. The comparative antiproliferative activity of the extractive and major triterpenoid components was studied using a number of human and murine malignant (P19, N2/D1, K1735-M2, PC-3 and CaOV3) and normal (BJ) cell lines. Betulin 3-caffeate was found to exhibit the highest antiproliferative activity among all triterpenoid components, including betulinic acid. Synthesis of betulin 3-caffeate from betulin has been developed.
Steroidal Glycosides from the Underground Parts of Agapanthus inapertus and Their Cytotoxic Activity
Authors: Yokosuka Akihito , Mimaki Yoshihiro
Published: March 2019

Phytochemical investigation of the underground parts of Agapanthus inapertus (Liliaceae) has resulted in the isolation of three new spirostanol glycosides (1, 3, and 4), along with a known spirostanol glycoside (2) and two known spirostanols (5 and 6). The structures of the new glycosides were determined by spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activity against HL-60 human promyelocytic leukemia cells.
New Neuritogenic Steroid Glycosides from the Vietnamese Starfish Linckia Laevigata
Authors: Kicha Alla A. , Ivanchina Natalia V. , Kalinovsky Anatoly I. , Dmitrenok Pavel S. , Palyanova Natalia V. , Pankova Tatyana M. , Starostina Marina V. , Gavagnin Margherita , Stonik Valentin A.
Published: March 2019

Two new steroid glycosides, linckosides L1 (1) and L2 (2), were isolated, along with the previously known echinasteroside C (3) from the ethanolic extract of the Vietnamese blue starfish, Linckia laevigata. The structures of the new compounds were elucidated by spectroscopic methods (mainly 2D NMR) and chemical transformations. Lifetime observations and analyses of silver impregnated preparations on the culture of neuroblastoma C-1300 cells showed that glycosides 1, 2, and 3 are capable of inducing neuronal differentiation similar to that of neurotrophins and of enhancing substantially the neuritogenic activity of NGF.
Synthesis of Polyhydroxylated Δ13-17,17-dialkyl-18-norsteroids by BF3·Et2O/Ac2O-promoted Wagner-Meerwein Rearrangement of Furostanols
Authors: Iglesias-Arteaga Martín A. , Mendez-Stivalet José. M. , Pérez Nury
Published: March 2019

Two polyhydroxylated Δ13-17,17-dialkyl-18-norsteroids were prepared by BF3·Et2O/Ac2O-promoted regioselective E-ring cleavage/ 1-2 hydride shift/ Wagner-Meerwein rearrangement of furostanols derived from the steroid sapogenins diosgenin and sarsasapogenin. Details of the spectroscopic characterization are discussed.