bluuebunny/crossref_metadata_2025 huggingface dataset:
A Randomized Assessor-Blinded Wait-List-Controlled Trial to Assess the Effectiveness of Acupuncture in the Management of Chemotherapy-Induced Peripheral Neuropathy
Authors: Molassiotis Alexander , Suen Lorna K. P. , Cheng Hui Lin , Mok T. S. K. , Lee Sara C. Y. , Wang C. H. , Lee Paul , Leung Howan , Chan V. , Lau T. K. H. , Yeo Winnie
Published: March 2019

Purpose: Chemotherapy-induced peripheral neuropathy is a complex side effect with few available treatment options. The aim of the study was to test the effectiveness of an 8-week course of acupuncture in the management of chemotherapy-induced peripheral neuropathy in cancer patients who were receiving or had received neurotoxic chemotherapy. Methods: Randomized assessor-blinded controlled trial with 2 arms; one arm received acupuncture twice weekly for 8 weeks, while the other arm was a wait-list control group receiving only standard care. Primary outcome was pain intensity and interference over the past week using the Brief Pain Inventory at the end of the intervention. Secondary outcomes included clinical assessment (CTCAE [Common Toxicity Criteria for Adverse Events] grading and Total Neuropathy Score–Clinical Version) and nerve conduction studies; and patient-reported outcome measures (Functional Assessment of Cancer Therapy–Gynecologic Oncology Group–Neurotoxicity Quality of Life scale and Symptom Distress Scale) assessed at baseline, end of treatment (8 weeks), week 14, and week 20 from the beginning of treatment. Results: Eighty-seven patients were randomized to the experimental arm (n = 44) and to the standard care wait-list control arm (n = 43). Significant changes at 8 weeks were detected in relation to primary outcome (pain), the clinical neurological assessment, quality of life domains, and symptom distress (all P < .05). Improvements in pain interference, neurotoxicity-related symptoms, and functional aspects of quality of life were sustained in the 14-week assessment ( P < .05), as were physical and functional well-being at the 20-week assessment ( P < .05). Conclusions: Acupuncture is an effective intervention for treating chemotherapy-induced peripheral neuropathy and improving patients’ quality of life and experience with neurotoxicity-related symptoms with longer term effects evident.
Identifying human and murine M cellsin vitro
Authors: Klisuric Ana , Thierry Benjamin , Delon Ludivine , Prestidge Clive A , Gibson Rachel J
Published: March 2019

M cells are an epithelial cell population found in the follicle-associated epithelium overlying gut-associated lymphoid tissues. They are specialized in the transcytosis of luminal antigens. Their transcytotic capacity and location in an immunocompetent environment has prompted the study of these cells as possible targets for oral drug delivery systems. Currently, the models most commonly used to study M cells are restricted to in vivo experiments conducted in mice, and in vitro studies conducted in models comprised either of primary epithelial cells or established cell lines of murine or human origin. In vitro models of the follicle-associated epithelium can be constructed in several ways. Small intestinal Lgr5+ stem cells can be cultured into a 3D organoid structure where M cells are induced with RANKL administration. Additionally, in vitro models containing an “M cell-like” population can be obtained through co-culturing intestinal epithelial cells with cells of lymphocytic origin to induce the M cell phenotype. The evaluation of the efficiency of the variations of these models and their relevance to the in vivo human system is hampered by the lack of a universal M cell marker. This issue has also hindered the advancement of M cell-specific targeting approaches aimed at improving the bioavailability of orally administered compounds. This critical review discusses the different approaches utilized in the literature to identify M cells, their efficiency, reliability and relevance, in the context of commonly used models of the follicle-associated epithelium. The outcome of this review is a clearly defined and universally recognized criteria for the assessment of the relevance of models of the follicle-associated models currently used.

Impact statement

The study of M cells, a specialized epithelial cell type found in the follicle-associated epithelium, is hampered by the lack of a universal M cell marker. As such, many studies lack reliable and universally recognized methods to identify M cells in their proposed models. As a result of this it is difficult to ascertain whether the effects observed are due to the presence of M cells or an unaccounted variable. The outcome of this review is the thorough evaluation of the many M cell markers that have been used in the literature thus far and a proposed criterion for the identification of M cells for future publications. This will hopefully lead to an improvement in the quality of future publications in this field.
Comparison of In Situ Versus Subcutaneous Versus Submuscular Transpositions in the Management of McGowan Stage III Cubital Tunnel Syndrome
Authors: Izadpanah Ali , Gibbs Christopher , Spinner Robert J. , Kakar Sanjeev
Published: March 2019

Background: The objective of the study was to evaluate and compare the clinical outcomes of in situ decompression with subcutaneous and submuscular transpositions for surgical management of advanced (McGowan stage III) cubital tunnel syndrome (CuTS). Methods: A retrospective review of patients in our institution undergoing primary surgery for CuTS from February 1989 to May 2009 was performed. Patients with advanced CuTS with a minimum of 12 months of follow-up without any previous bony or soft tissue procedures around the elbow were included. Seventy-four patients underwent 80 primary ulnar nerve surgeries. Patients’ demographics, presenting symptoms, physical examination, electrodiagnostic findings, and perioperative complications were recorded. Primary surgical techniques were compared and the risk factors for revision surgery were assessed. Results: Of the 80 surgical procedures, there were 17 decompressions (21%), 47 subcutaneous transpositions (59%), and 16 submuscular transpositions (20%). Fifty-two percent of patients had resolution of their symptoms after primary surgery. The overall complication rate after primary surgery was 12.5%. Nineteen patients (24%) had revision surgery at a median of 30 months after their primary procedure. Eight patients (42%) had symptomatic improvement after revision surgery. Patients with their dominant extremity affected, static 2-point discrimination (S2PD) greater than 10 mm, and age less than 50 years at presentation had a higher rate of revision surgery. Three patients had a second revision surgery and neurolysis for persistent symptoms. Conclusions: The overall revision rate in advanced CuTS was 24%. Forty-two percent of patients had reported subjective symptomatic improvement after revision surgery. Younger age at presentation and a greater S2PD were associated with a higher rate of revision surgery.
5,7-Dihydroxy-5,6,7,8-tetrahydro-1H-azocin-2-one from a Marine-derived Streptomyces sp.
Authors: Fotso Serge , Wu Shao Jie , Qin Song , Laatsch Hartmut
Published: March 2019

In the course of a screening program, we have isolated the new natural product, 5,7-dihydroxy-5,6,7,8-tetrahydroazocin-2( 1H)-one (1), from the staurosporine producing marine-derived Streptomyces sp. strain QD518. Here we report the isolation and structure elucidation of 1 and the artifacts 3 and 4 resulting from 1 by acid catalyzed intra- and inter-molecular reactions.
Seasonal Variation in Bromophenol Content of Polysiphonia lanosa
Authors: Shoeib Nagwa A. , Bibby Michael C. , Blunden Gerald , Linley Peter A. , Swaine David J. , Wright Colin W.
Published: March 2019

The bromophenol content of Polysiphonia lanosa, determined by GLC-MS, was shown to vary considerably between late spring and early autumn. The lowest content was found in material collected in early May and then the levels rose until a peak was reached in July. When the extracts were tested for cytotoxicity against DLD-1 cells, a direct correlation was shown between cytotoxicity and bromophenol abundance, confirming that these compounds are the ones responsible for the cytotoxicity of the species.
Chemical Composition and Bioactivity of the Leaf Oil of Calyptranthes pallens (Poir.) Griseb. from Abaco Island, Bahamas
Authors: Bansal Anita , Boehme Amelia K. , Eiter Lauren C. , Schmidt Jennifer M. , Setzer William N. , Vincent Michael A.
Published: March 2019

The leaf oil of Calyptranthes pallens was obtained by hydrodistillation and analyzed by GC/MS. The most abundant oil components were the monoterpenoids α-pinene (24.7%), α-terpineol (13.8%), and trans-pinocarveol (11.6%). The antimicrobial activity against Bacillus cereus, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Candida albicans, and Aspergillus niger, and the in-vitro cytotoxicity of the oil on Hep G2, MDA-MB-231, Hs 578T, and PC-3 human tumor cells were also examined.
Clerodane Diterpenes from Croton Species: Distribution and a Compilation of their 13C NMR Spectral Data
Authors: Jünior Sebastião F. Palmeira , Conserva Lucia M. , Filho José Maria Barbosa
Published: March 2019

The present work is a review of the literature of clerodane diterpenes from Croton species. It contains a compilation of 13C NMR data of 83 of these diterpenoids and their biological activities. This review covers a period from 1969 to October 2005 and 224 references are cited.
Tephrosia Toxicaria Pers Essential Oil: Chemical Composition and Larvicidal Activity
Authors: Ribeiro Walber H. F. , Vasconcelos Jackson N. , Arriaga Angela M. C. , de Oliveira Maria C. F. , Andrade-Neto Manoel , Lemos Telma L. G. , Santiago Gilvandete M. P. , Nascimento Ronaldo F. , Mafezoli Jair
Published: March 2019

The essential oils obtained by hydrodistillation of the leaves, stems, and shoots of Tephrosia toxicaria Pers (Papilionaceae) were analyzed using GC and GC/MS. Germacrene D was the major component (20.7-33.3 %) of the oils of leaves and shoots, whereas spathulenol was the main constituent (42.3%) of the stem oil. The essential oils from the leaves and stems, when tested for activity against mosquito larvae (Aedes aegypti), gave LC 50 values of 81.3 ± 2.9 and 63.1 ± 1.0 ppm, respectively.
Acetylenic Terrestrial Anticancer Agents
Authors: Dembitsky Valery M , Levitsky Dmitri O
Published: March 2019

Acetylenic metabolites belong to a class of molecules containing triple bond(s). They are found in plants, fungi, microorganisms, and marine invertebrates. This review presents 139 active acetylenic molecules of plant, fungal, and soil bacterial origin that reveal cytotoxic and/or anticancer activities. Although many compounds of this group possess encouraging characteristics, they have never been evaluated as potential anticancer agents. They are of great interest, especially for the medicine and/or pharmaceutical industries. Here we describe structures and biological activities of acetylenic metabolites.
A Pregnane Derivative and an Anti-plasmodial Labdane Diterpenoid from the Stem Bark of Turraenthus Africanus
Authors: Akam Thomas M. , Tane Pierre , Wabo Hippolyte K. , Yong Joseph N. , Fanso-Free Samual N. Y. , Connolly Joseph D. , Evans Cameron , Farrugia Louis J.
Published: March 2019

Chemical investigation of the stem bark of Turraeanthus africanus (Meliaceae) afforded a new pregnane derivative, 17α,20S-dihydroxypregn-4-ene-3,16-dione, named turraeasterodione, together with three known diterpenoids, methyl 14,15-epoxylabda-8(17),12E-dien-16-oate, 16-oxolabda-8(17),12E-dien-15-oic acid, and 16-acetoxy-12R,15-epoxylabda-8(17),13(16)-dien-15β-ol. Their structures were elucidated by spectroscopic and spectrometric methods. Methyl 14,15-epoxylabda-8(17),12E-dien-16-oate was found to exhibit anti-plasmodial activity against a chloroquine-resistant strain of Plasmodium falciparum.
Flavonoid C-Glycosides from Pterocephalus Sanctus Growing in Egypt
Authors: Ahmed Fahem A. , Shahat Abdelaaty A.
Published: March 2019

Two flavonoid C-glycosides, isolated from Pterocephalus sanctus (Dipsaceae), were identified as luteolin-6-C-β-D-glucoside-7-O-methyl ether and apigenin-6-C-β-D-glucoside-7-O-methyl ether on the basis of spectroscopic studies.
Chemical Constituents from Alnus formosana Burk. II. Polar Constituents from the Leaves
Authors: Lee Shoei-Sheng , Chen Su-Chang , Chen Chien-Kuang , Chen Chung-Hsiung , Kuo Chen-Meng
Published: March 2019

This study was aimed to explore the n-BuOH soluble constituents of the leaves of Alnus formosana Burk. A total of 13 compounds were isolated and characterized. Of these, 2″'-cinnamoyloregonin is a new diaryl heptanoid glycoside. Ten of the remaining twelve known compounds, i.e. platyphylloside, aceroside VII, myzodendrone, quercetin, kaempferol-3-O-rhamnoside, quercetin-3-O-rhamnoside, quercetin-3-O-glucoside, rhamnetin-3-O-rhamnoside, inositol, and shikimic acid, are reported for the first time for an Alnus species. The structures were characterized by spectral analysis.
A Simple Differential Pulse Polarographic Method for the Determination of Artemisinin in Artemisia Annua
Authors: Debnath Chhanda , Haslinger Ernst , Ortner Astrid
Published: March 2019

A reliable and simple differential pulse polarographic method is presented for the determination of the antimalarial artemisinin in Artemisia annua. The polarographic behaviour of artemisinin was examined in various buffer systems over the pH range 2–10. Artemisinin was irreversibly reduced at the dropping mercury electrode. In 0.1 M KH2PO4, pH 5.5, mixed with methanol (7:3; v/v), the differential pulse polarograms exhibited reproducible peaks at 0.0 V vs. Ag/AgCl and a plot of peak height against concentration of artemisinin was found to be linear over the range 6.4 × 10−7 - 3.2 × 10−5 mol/L (R = 0.9998). The detection limit was calculated to be 58 ng/mL. The polarographic method was applied to the determination of the content of artemisinin in the traditional Chinese herbal drug Artemisia annua L. by using the standard addition method. The proposed DPP method is sensitive, precise and time-efficient and is, therefore, suitable for quantitative analysis of artemisinin in plant extracts.
A Novel Sesquiterpene Polyol Ester from the Celastrus Rosthornianus with Anti-tumor Activities
Authors: Wang Kuiwu , Pan Yuanjiang
Published: March 2019

A new (1) and a known (2) β-dihydroagarofuran sesquiterpene polyol esters were isolated from Celastrus rosthornianus and their structures were established by 1D- and 2D-NMR spectroscopic techniques. The two compounds exhibited anti-tumor activities against a panel of human tumor cell lines.
Oestrogenic Isoflavone Content in Natural Strains of Subterranean Clover (Trifolium subterraneum L.) from Sardinia
Authors: Tava Aldo , Pecetti Luciano , Bertoli Alessia , Piano Efisio
Published: March 2019

A collection of subterranean clover (Trifolium subterraneum L.) genotypes from Sardinia was evaluated for the content of oestrogenic isoflavones to assess differences in total and individual compounds. Daidzein, genistein, and their respective 4′-methoxy derivatives biochanin A and formononetin, were detected in leaves and quantified by GC/FID and GC/MS methods. A large variation among genotypes for individual compounds and for the total isoflavone concentration was observed. Total isoflavones were measured in the range 0.8-13.4 mg/g fresh weight (0.3-4.5% dry matter). Daidzein was usually present in lower amount compared to the other isoflavones. Genistein and biochanin A were found in most cases in higher concentration than formononetin. Phyto-oestrogens have been shown to have both oestrogenic and anti-oestrogenic properties, and their effects entail a positive role for the human health. T. subterraneum revealed the presence of higher concentration of isoflavones compared to other sources of these compounds, e.g. soybean (Glycine max (L.) Merrill) and red clover (Trifolium pratense L.). This study provided information on the biodiversity of the natural strains from Sardinia, emphasizing the importance of these genetic resources for their variation in the amount of total and individual isoflavones.
Dendrimers as Drug Carriers. A New Approach to Increase the Potential of Bioactive Natural Products
Authors: Demetzos Costas
Published: March 2019

Nanotechnology is a challenging field in science and its application in medicine will bring significant advantages in the treatment of diseases. According to the World Health Organization there is a need for improved therapies against cancer, AIDS and Alzheimer's disease. The new therapies include the design of drug delivery systems, which are able to deliver new bioactive natural products to the target tissues. Dendrimers are hyperbranched polymers with well defined structure and molecular weight; they are composed of a central core and repeated branching units; they have a globular shape, low polydispersity and large void internal spaces that can be used for the encapsulation and delivery of many classes of compounds. Nanosystems, such as dendrimers, can achieve successful administration of poorly water-soluble compounds and those with narrow therapeutic indices.
Anti-Trypanosomal Alkaloids from Xymalos Monospora
Authors: Ngamga Dieudonne , Tane Pierre , Rattendi Donna , Bacchi Cyrus , Okunji Christopher C. , Iwu Maurice M. , Schuster Brian M. , Sterner Olov
Published: March 2019

From an extract of the stem bark of Xymalos monospora, a bis-benzylisoquinoline alkaloid (1), three benzylisoquinoline alkaloids (mollinedine, 1-(p-methoxybenzyl)-6,7-methylenedioxyisoquino-line, doryafranine), and an aporphine alkaloid (N-methyllaurotetanine) were isolated. These compounds were tested for growth inhibitory activity against bloodstream forms of three strains of African trypanosomes. In vitro IC50 values starting from 1.8 μg /mL were obtained.
Chemodiversity of Exudate Flavonoids in Baccharis Concinna and Three Further South-American Baccharis Species
Authors: Wollenweber Eckhard , Valant-Vetschera Karin M. , Fernandes G. Wilson
Published: March 2019

Four Baccharis species were studied for their exudate flavonoid composition. General accumulation trends observed include flavone and flavonol methyl ethers as well as flavanones and also, in part, chromenes. B. concinna was analyzed for infraspecific variability, differentiating between male and female individuals from three different habitat locations and between foliar and cauline flavonoid expression. The minute differences observed between male and female populations and those observed between cauline and foliar material did not lead to a correlation pattern. The exudate flavonoid complements observed in B. concinna, B. linearis, B. confertifolia and B. lycioides are well in agreement with literature data, of which only a few relate to exudate occurrence.
Thiocarbamates from Moringa Oleifera
Authors: Tewari Amit , Bhakuni Rajendra S.
Published: March 2019

Two new thiocarbamates (1 and 2) along with two known compounds have been isolated from the ethyl acetate extract of Moringa oleifera seeds. The new compounds were characterized as O-n-butyl-4-[(α-L-rhamnopyranosyloxy)benzyl] thiocarbamate (E) (1) and O-ethyl-4–[(α-L-rhamnopyranosyloxy)–3-hydroxybenzyl]thiocarbamate (E) (2) on the basis of 1D and 2D NMR spectroscopic data and MS analysis.
Antioxidant and Anti-Proliferative Active Constituents of Tecoma Stans against Tumor Cell Lines
Authors: Marzouk Mohamed SA , Gamal-Eldeen Amira M , Mohamed Mona A , El-Sayed Mortada M
Published: March 2019

A new phenylethanoid, 2-(3,4-dihydroxyphenyl)ethyl-,2-O-(6-deoxy-α-L-mannopyranosyl-,4-(3,4-dihydroxyphenyl)-2-propenoate)-β-D-glucopyranoside (3) and a novel monoterpene alkaloid, 5-hydroxy-skytanthine hydrochloride (8), along with eleven known compounds have been isolated from Tecoma stans Juss. fruits and flowers. 4-O-E-Caffeoyl-α-L-rhamnopyranosyl-(1′→3)-α/β-D-glucopyranose (1), E/Z-acetoside (2), isoacetoside (4), rutin (5), luteolin 7-O-β-D-neohespridoside (6), luteolin 7-O-β-D-glucopyranoside (7) and sucrose (9) were isolated from the fruits, while luteolin 7-O-β-D-glucuronopyranoside (10), diosmetin 7-O-β-D-glucuronopyranoside (11), diosmetin 7-O-β-D-glucopyranoside (12), diosmetin 7-O-β-D-glucuronopyranoside methyl ester (13), and 2 from the flowers. Their structures were determined on the basis of chemical and spectroscopic evidence. It was found that the extract of T. stans fruits and compounds 1, 2 and 4 possess strong scavenging activity to DPPH, peroxyl and hydroxyl radicals. Unlike 4, which potentially induced NO generation in bacterial lipopolysaccharide-stimulated Raw murine macrophages (RAW 264.7), the extract, and compounds 1, 2, and 8 significantly inhibited NO generation. The extract, and compounds 2 and 4 exhibited a cytotoxic effect on human hepatocarcinoma cells (Hep-G2), while the extract, 2 and 8 were potent growth inhibitors of human breast carcinoma (MCF-7). Also, 1 and 2 were remarkable growth inducers of human lymphoblastic leukemia cells (1301), whereas the extract, 2, and 8 stimulated the macrophage proliferation rate.
Phytochemical Studies on Stemona Plants: Isolation of New Tuberostemonine and Stemofoline Alkaloids
Authors: Sastraruji Thanapat , Jatisatienr Araya , Issakul Kritchaya , Pyne Stephen G. , Ung Alison T. , Lie Wilford , Williams Morwenna C.
Published: March 2019

Two new tuberostemonine alkaloids, tuberostemonine L (3) and tuberostemonine M (4) and a new stemofoline alkaloid, (3′S)-hydroxystemofoline (5), along with two known alkaloids, (2′S)-hydroxystemofoline (1) and neotuberostemonine (2) have been isolated from a root extract of an unidentified Stemona species (Stemona sp.). The structure and relative configuration of these new alkaloids has been determined by spectral data interpretation, while the 3′S configuration of 5 was determined from NMR analysis of its (R)- and (S)-Mosher esters.
A General and Efficient Approach to the Proposed Structures of Frog Toxins: The 5-Alkylindolizidines
Authors: Gourlay Brendon S. , Little Ian , Ryan John H. , Smith Jason A.
Published: March 2019

The structural assignments of a number of bicyclic alkaloids isolated from frogs have been reassigned or questioned after synthesis of the proposed structures. Herein we report a practical and short formal synthesis of the 5-alkylindolizidine core, from readily available α-amino acids or homoserine that could be utilized to support structural assignments.
Preparation of Cyclic Peptide Alkaloids Containing Functionalized Tryptophan Residues
Authors: Yuen Alexander K. L. , Hutton Craig A.
Published: March 2019

This review covers the synthesis of various cyclic peptide natural products possessing highly functionalized tryptophan residues, focusing on the examples of diazonamide A, the TMC-95 compounds, the celogentin/moroidin family and the complestatin/chloropeptin system. Recent efforts toward the preparation of these modified-tryptophan-containing peptides will be outlined, focusing primarily on the novel methods for the assembly of the highly functionalized indole/tryptophan moieties at the core of these structures.
Comparative Investigation of O- and C-Glycosylflavones in Leaves of Six Santalum Insulare (Santalaceae) Varieties
Authors: Butaud Jean-François , Raharivelomanana Phila , Loquet Denis , Bianchini Jean-Pierre , Faure Robert , Gaydou Emile M.
Published: March 2019

Leaves (108 samples) of six Santalum insulare (Santalaceae) varieties, i.e. raivavense, margaretae, marchionense, raiateense, alticola, and insulare from French Polynesia, have been investigated for their O- and C-glycosylflavone contents. Apigenin-7-O-neohesperidoside was found in low amounts in all varieties except in some samples of variety insulare, whereas luteolin-7-O-neohesperidoside was found in high amounts in alticola and insulare varieties (19.2 and 24.9%, respectively). Apigenin-8-C-β-D-glucopyranoside (vitexin) was found in all varieties with contents ≤ 4.3 %, and the content of apigenin-6-C-β-D-glucopyranoside (isovitexin) was highest in marchionense variety (12.5%). Luteolin-6-C-β-D-glucopyranoside (isoorientin) contributes to the differentiation of marchionense and alticola varieties (39.6 and 40.5%, respectively), whereas apigenin-6,8-di-C-β-D-glucopyranoside (vicenin-2) was found in high amounts in raivavense, margaretae, and raiateense varieties (56.2, 53.7 and 55.8% respectively), together with luteolin-6,8-di-C-β-D-glucopyranoside (lucenin-2) (12.4, 15.8 and 18.6% respectively).
Plant Sources of Propolis: An Update from a Chemist's Point of View
Authors: Bankova Vassya , Popova Milena , Trusheva Boryana
Published: March 2019

The newest developments in research on propolis plant sources are summarized. Special attention is paid to data based on reliable chemical evidence including comparison between propolis samples and plant material, and on well-documented bee behavior. A number of new proved propolis source plants are listed. Hypothetical sources, suggested as a result of comparison of propolis chemical composition and literature data about particular plants are also discussed.
Hypericum Perforatum L., H. Maculatum Crantz., H. Calycinum L. and H. pulchrum L.: Phytochemical and Morphological Studies
Authors: Fico Gelsomina , Vitalini Sara , Colombo Noemi , Tomè Franca
Published: March 2019

Four species of Hypericum growing in Italy were characterized morphologically and chemically: Hypericum perforatum L., H. maculatum Crantz., H. calycinum L. and H. pulchrum L. The composition of secondary metabolites (phloroglucinols, naphthodianthrones, flavonoids) in the aerial parts of plants collected in different habitats was analysed. The four species show different compositions of phloroglucinols and naphthodianthrones, but there was no qualitative difference in flavonoid content of the species analysed. Study of main-constituent variation during the ontogenetic cycle showed that hypericin decreases and hyperforin increases during the reproductive phase. In St. John's Wort, hypericin and hyperforin are thought to be localised in black nodules. Our investigation shows no clear correlation between either the presence or absence of nodules and hypericin or hyperforin content.
A Convenient Synthesis of 5′-Iodoresiniferatoxin (I-RTX)
Authors: Ech-Chahad Abdellah , Bouyazza Lahboub , Appendino Giovanni
Published: March 2019

Starting from resiniferonol orthophenylacetate (ROPA, 2) and commercial 5-iodovanillin (5a), a convenient synthesis of the ultrapotent vanilloid antagonist 5′-iodoresiniferatoxin (1a) was achieved, overcoming the problems involved in the direct iodination of either resiniferatoxin (1b) or homovanillic acid (3a).
A New Irregular Diterpenoid of Biogenetic Interest from the Flowers of Magydaris Tomentosa (Desf.) DC. (Apiaceae)
Authors: Rosselli Sergio , Maggio Antonella Maria , Bellone Gabriella , Formisano Carmen , Senatore Felice , Bruno Maurizio
Published: March 2019

A new irregular acyclic diterpene, magytomol acetate (2), has been isolated from the light petroleum extract of the flowers of Magydaris tomentosa (Desf.) DC. (Apiaceae) and its structure has been elucidated by means of extensive spectroscopic experiments. The new compound can be considered the acetyl derivative of the biogenetic precursor of other irregular diterpenes isolated from other species belonging to the family Apiaceae.
Phenolic Constituents of Leaves of Diospyros Montana
Authors: Tanaka Toshiyuki , Furusawa Miyuki , Ito Tetsuro , Iliya Ibrahim , Oyama Masayoshi , Iinuma Munekazu , Tanaka Nobuyuki , Murata Jin
Published: March 2019

Five flavonol glycosides (1–5) and two naphthalene dimer glycosides (7 and 8), including three new compounds (1, 2 and 8), were isolated from the leaves of Diospyros montana. The structures of the isolated compounds were determined by spectroscopic analysis. One of the isolated compounds (1) showed DPPH radical scavenging activity.
Two Phorbol Esters from Sapium Hippomane
Authors: Grosvenor Sumieya N. J. , McLean Stewart , Reynolds William F. , Tinto Winston F.
Published: March 2019

A chemical study of the bark of Sapium hippomane (Euphorbiaceae), obtained in the parish of St. John, Barbados, led to the isolation of two new phorbol esters (1 and 2), in addition to the known compound 4-deoxyphorbol (3). Compounds 1 and 2 were C-4 epimers, with a tigliane-type skeleton possessing C5 esters at C-12 and C-13. Chromatographic methods were utilized to separate the compounds and their structures determined through interpretation of physical data.
Diterpenes from the Brazilian Brown Alga Dictyota Crispata (Dictyotaceae, Phaeophyta)
Authors: De-Paula Joel Campos , Cassano Valéria , Yoneshigue-Valentin Yocie , Teixeira Valéria Laneuville
Published: March 2019

Diterpenes from the Dictyoteae tribe appear to be valuable taxonomic markers and have showed, for various species, strong correlation with morphological data. Dictyota crispata Lamouroux is close to D. cervicornis Kützing. Crude extract of Brazilian D. crispata was analysed and compared by analytical TLC and NMR data with both the crude extract and the most abundant diterpenes of D. cervicornis. The results showed that D. crispata produces the same diterpenes as D. cervicornis, and thus the two species cannot be separated by chemotaxonomic studies. Our results indicate that the divergence time between these two species is small.
Amides Produced by Streptoverticillium Morookaense
Authors: Feng Na , Ye Wanhui , Wu Ping , Huang Yicun , Lin Lidong , Wei Xiaoyi
Published: March 2019

A new amide, 5,8-dimethoxynaphthalene-2-carboxamide (1), together with 2-phenylacetamide (2), 4-methoxybenzamide (3), 3,4-dimethoxybenzamide (4), 3,4-dimethoxycinnamamide (5), and 4,6-diacetylaminoresorcinol (6), was isolated from the solid culture of Streptoverticillium morookaense. The structure was elucidated by spectroscopic methods. The antifungal activity of the isolated amides was assessed against Peronophythora litchii.
Structural Elucidation of a New Aromatic Metabolite from Melilotus Neapolitana and its Potential Allelopathic Effect on Wild Species
Authors: Fiorentino Antonio , D'Abrosca Brigida , Oriano Palma , Golino Annunziata , Natale Angela , Monaco Pietro
Published: March 2019

From the ethereal extract of Melilotus neapolitana Ten., an herbaceous plant living in the Mediterranean macchia, a new aromatic metabolite was isolated. The structure 1-(2,4-dihydroxyphenyl)2-(4-hydroxy-2-methoxyphenyl)1,3-propandiol, was elucidated on the basis of its mass spectrum and 1D and 2D NMR spectroscopic data (DQ-COSY, TOCSY, HSQC, HMBC). The relative configuration was determined from NOESY/ROESY experiments and computational calculations. The compound was tested for its potential allelopathic effect on two wild plant species living in the same habitat as M. neapolitana.
Molluscicidal Activity of Polyacetylenes from Ambrosia maritima Hairy Roots
Authors: AbouZid Sameh , Orihara Yutaka , Kawanaka Masanori
Published: March 2019

Thiarubrine A, thiarubrine A epoxide, thiarubrine A diol, and their precursor pentayneene were produced by hairy roots of Ambrosia maritima. The molluscicidal activity of the lipophilic extract of the hairy roots and isolated polyacetylenes were investigated. The activity was studied against Schistosome intermediate host Biomphalaria glabrata. Thiarubrine A diol, the main form detected in the medium, showed the highest activity with LC50 = 0.37 ppm. This activity is 23 times higher than that of ambrosin, a sesquiterpene lactone that has long been regarded as the main molluscicidal agent of the plant. Thiarubrine A diol can be an environmentally accepted molluscicidal agent in areas endemic with schistosomiasis.
Aporphine Alkaloids from the Chinese Tree Neolitsea Aurata Var. Paraciculata
Authors: Buchanan Malcolm S. , Carroll Anthony R. , Pass David , Quinn Ronald J.
Published: March 2019

Three new oxygenated noraporphine alkaloids were isolated from the bark of the Chinese tree Neolitsea aurata var. paraciculata. The new compounds, (+)-11-methoxynorcassythicine, (+)-11-methoxynorneolitsine, (+)-11-methoxynorboldine, were isolated along with eight known aporphine alkaloids, hernovine, ovigerine, N-methylovigerine, 10-O-methylhernovine, lindcarpine, N,O-dimethylhernovine, laurolitsine and nandigerine. Their structures were determined by 1D and 2D NMR spectroscopy. This is the first report of chemical constituents from N. aurata var. paraciculata.
Potential Anti-obesity and Lipid Lowering Natural Products: A Review
Authors: Bhutani Kamlesh Kumar , Birari Rahul , Kapat Kausik
Published: March 2019

Obesity has reached epidemic proportions globally, with more than 1 billion adults overweight - at least 300 million of them clinically obese. In Ayurveda, obesity is called ‘medoroga’. The detailed features and treatments of the disease have been described in an old Ayurvedic text, Charak and Sushrut Samhita. There are some native plants that are commonly used for the treatment of obesity in Ayurveda. Unfortunately, only few medications are available in the market, with side effects and unacceptable efficacy. With the current view that botanical drugs can be developed faster and more cheaply than conventional single entity pharmaceuticals, the review mainly focuses on the rationality of their use with appropriate literature data support.
Assessment of the Antioxidant Ability of Thymus albicans, T. mastichina, T. camphoratus and T. carnosus Essential Oils by TBARS and Micellar Model systems
Authors: Miguel M. Graça , Costa Ludmila A. , Figueiredo A. Cristina , Barroso José G. , Pedro Luís G.
Published: March 2019

The essential oils isolated by hydrodistillation from different populations of Thymus albicans, T. mastichina, T. carnosus and T. camphoratus, collected during the vegetative phase, were analysed by GC and GC-MS. The same oils were used in the antioxidant activity evaluation using the TBARS assay and the micellar model systems. T. albicans oils and two of the oils from T. mastichina populations were 1,8-cineole-rich. The third T. mastichina oil was linalool-rich. trans-Sabinene hydrate, borneol and linalool in similar amounts, and 1,8-cineole were the main components of the oils from each of the three populations of T. camphoratus. T. carnosus oils were mainly composed of borneol. All essential oils revealed some degree of antioxidant activity either in the presence or absence of ABAP in the TBARS method. The micellar model system showed higher antioxidant indices than those obtained by the TBARS method.
Chemical Composition, Olfactory Evaluation and Antimicrobial Activities of Jasminum grandiflorum L. Absolute from India
Authors: Jirovetz Leopold , Buchbauer Gerhard , Schweiger Thomas , Denkova Zapriana , Slavchev Alexander , Stoyanova Albena , Schmidt Erich , Geissler Margit
Published: March 2019

The chemical composition of a sample of Jasminum grandiflorum L. absolute from India was analyzed by GC and GC/MS. The major compounds identified were benzyl acetate (23.7%), benzyl benzoate (20.7%), phytol (10.9%), linalool (8.2%), isophytol (5.5%), geranyl linalool (3.0%), methyl linoleate (2.8%) and eugenol (2.5%). The odor of this absolute sample was olfactorically evaluated as intense and heavy floral-flowery, with penetrant-animalic and fruity side-notes. Some main and minor compounds were found to be responsible for the aroma impression of this sample.

The antimicrobial activities of the J. grandiflorum sample and of some of its main and minor compounds were tested against Gram-positive and Gram-negative bacteria, as well as against the yeast Candida albicans, using agar dilution and agar diffusion methods. The jasmine absolute showed medium to high activity (reference compounds: eugenol and three synthetic antibiotics) against the Gram-positive bacterium Enterococcus faecalis, against the Gram-negative bacteria Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae and Salmonella sp., as well as against the yeast Candida albicans. A comparison of these biological data with those of some constituents of the jasmine absolute is also given.
Reliable Identification of Terpenoids and Related Compounds by using Linear Retention Indices Interactively with Mass Spectrometry Search
Authors: Costa Rosaria , De Fina Maria Rosa , Valentino Maria Rita , Dugo Paola , Mondello Luigi
Published: March 2019

An innovative tool in GC-MS peak assignment procedures is described. Besides considering the conventional spectra similarity matching, Linear Retention Indices are used as filters for enhancing reliability in compounds identification, especially in those cases ruled by ambiguity and uncertainty. This is a common issue when analyzing natural compounds (e.g. terpenoids) present in flavors, essential oils and fragrances that give rise to similar fragmentation patterns, and thus, to approximately identical spectra, making harder the unequivocal identification by the databases. Some applications of the method and its capabilities are reported.
Anti-tumor Properties of Stilbene-based Resveratrol Analogues: Recent Results
Authors: Chillemi Rosa , Sciuto Sebastiano , Spatafora Carmela , Tringali Corrado
Published: March 2019

Recent literature about stilbene-based analogues of resveratrol (1) has been reviewed, and a total of 94 compounds are reported (see structures 4 – 97), selected either for their promising anti-tumor properties or as comparative terms in SAR studies. As a general outline, these recent literature data confirm the previously reported observation that minimal modification in the nature and position of the substituents on the stilbene nucleus may cause large variations in their biological activity and, more specifically, in their anti-tumor properties. Among the polyhydroxylated stilbenes, it has been established that those with either a catechol or pyrogallol moiety are far better radical scavengers than either 1 or other analogues lacking an ortho-dihydroxy group, and this property was shown to be related to pro-apoptotic activity. In the large majority of cases where couples of E- and Z-isomers were evaluated for either cytotoxic or pro-apoptotic activity, the Z-isomers were significantly more active than their E analogues; nevertheless, a general rule stating that stilbenoids with Z configuration of the double bond display a considerably higher antiproliferative activity than their E-isomers cannot be considered as established. A variety of methoxystilbenes has been reported recently: in many cases these analogues showed either potent antiproliferative and pro-apoptotic activity or strong inhibition of TNFα-induced activation of NF- kB. Globally considered, polymethoxystilbenes are a sub-group of great interest among the resveratrol analogues: these analogues appear worthy of a deeper evaluation also in connection with their potential anti-angiogenic properties. In addition, in vivo studies indicate that methoxystilbenes undergo different metabolic conversion and have a higher bioavailability than resveratrol. The potent activity of some amino- and halogenated stilbenes is undoubtedly worthy of attention, but the toxicity of these compounds to normal cells has rarely been evaluated. In conclusion, the synthesis and evaluation of stilbene-based resveratrol analogues proved to be a highly active field of research and has recently afforded compounds with either cytotoxic or pro-apoptotic activity in the nanomolar range. Nevertheless, the exact structural determinants to optimize the anti-tumor properties of these compounds and details of their mechanism of action remain to be clarified.
Ferulol and epi-Samarcandin, Two New Sesquiterpene Coumarins from Ferula Sinaica
Authors: Ahmed Ahmed A. , Mohamed Abou El-Hamd H. , El-Razek Mohamed H. Abd , Hegazy Mohamed-Elamir F.
Published: March 2019

Re-investigation of the methylene chloride extract of the root of Ferula sinaica gave a sesquiterpene coumarin with a rare carbon skeleton and 3′,9′-di- epi-samarcandin. The structure elucidation was determined by MS; 1H- and 13C- 1D and 2D NMR spectral data.
Effect of Acylation of Flavones with Hydroxycinnamic Acids on their Spectral Characteristics
Authors: Stochmal Anna , Oleszek Wieslaw
Published: March 2019

The absorption spectra of twenty-one flavones including glycosides of apigenin, luteolin, chrysoeriol and tricin, nonacylated or acylated with coumaric, ferulic or sinapic acids, were examined to document the influence of acylation on their spectral characteristics. Acylation did not shift the absorption maximum of band II, but the molar absorption coefficients of this band increased 1.3–2.0 fold. Acylation of apigenin and chrysoeriol glycosides did not shift the absorption maximum of band I and the absorption maxima of nonacylated and acylated compounds were at 319–334 nm, but this increased their molar absorption coefficients 1.7–3.0 fold.

For luteolin and tricin glycosides, nonacylated compound maxima of absorption of band I were in the range of 342–349 nm. Acylation shifted band I absorption maxima to 329–340 nm and increased their molar absorption coefficient 1.6–1.8 fold. These data document that acylation of flavones leads to significant increase of their absorption in the 280–320 nm region and can be an effective mechanism of protecting plants against UV-B radiation.
Substituent Effect in Color of Ehrlich's Test of Tetrahydrobenzofuran
Authors: Kuroda Chiaki , Nishio Eriko
Published: March 2019

Reaction of 4,5,6,7-tetrahydrobenzofuran derivatives, model compounds of furanoeremophilanes, with p-dimethylamino-benzaldehyde (Ehrlich's reagent) under acidic conditions was studied both on TLC and in a flask. 4-Hydroxy, 4-methoxy, and 4-acetoxy derivatives showed a pink/purple color, while 7-hydroxy, 7-methoxy, and 7-acetoxy derivatives showed a dark green color. The reaction of a 4-oxo derivative was slow showing an orange color on TLC. 7-Oxo derivatives and benzofuran were negative to Ehrlich's test. It was shown that an intermediate cation corresponding to the pink color was generated from both 4- and 7-substituted derivatives except for the oxo-derivatives.
Selective Cytotoxicity and Antioxidant Effects of Compounds from Dioscorea membranacea Rhizomes
Authors: Itharat Arunporn , Plubrukan Anuchit , Kaewpradub Niwat , Chuchom Titima , Ratanasuwan Pranee , Houghton Peter J.
Published: March 2019

Bioassay-guided isolation was used to separate the active ingredients of the ethanolic extract of Dioscorea membranacea by testing cytotoxic activity against three human cancer cell lines, i.e. large cell lung carcinoma (COR-L23), colon cell line (LS-174T) and breast cancer cell line (MCF-7), and two normal human cell lines, keratinocytes (SVK-14) and normal human fibroblasts (HF), using the SRB assay. The DPPH test for antioxidant activity was also employed, as was a test for LDH release as an indicator of damage to the cell membrane. Eight compounds were isolated, two naphthofuranoxepins (dioscorealides A [1] and B [2]), a 1,4-phenanthraquinone (dioscoreanone [3]), three steroids (β-sitosterol [4], stigmasterol [5] and β-D-sitosterol glucoside [8]) and two steroid saponins diosgenin-(3- O-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranoside [6] and diosgenin 3- O-β-D-glucopyranosyl (1→3)-β-D-glucopyranoside [7]). Cytotoxic activity of 2, 3 and 6 was shown against three cancer cell lines, and 2 showed selective cytotoxic activity against lung and breast cancer, but was less active against the two normal cells, and was not toxic to cell membranes in the LDH assay. The highest antioxidant activity was shown by 3.
Volatile Constituents of the Stem and Root Barks of Pyrenacantha staudtii Engl
Authors: Lasisi Adebayo A. , Ogunwande Isiaka A. , Walker Tameka M. , Setzer William N.
Published: March 2019

The volatile oils obtained by hydrodistillation of the stem and root barks of Pyrenacantha staudtii Engl. (Icacinaceae) were analyzed for their constituents by Gas chromatography-Mass spectrometry (GC-MS). Hexadecanoic acid (38.7% and 63.0%) and 1, 8-cineole (11.1% and 4.6%) are the quantitatively significant constituents of the oils, respectively.
Anti-inflammatory Effects of a Sesquiterpene Lactone Extract from Chicory (Cichorium intybus L.) Roots
Authors: Ripoll Christophe , Schmidt Barbara M. , Ilic Nebojsa , Poulev Alexander , Dey Moul , Kurmukov Anvar G. , Raskin Ilya
Published: March 2019

A chicory root extract rich in sesquiterpene lactones significantly reduced inflammation in two animal models. In a rat paw edema model, chicory extract at 50 and 100 mg/kg significantly reduced inflammation by 58 and 76%, respectively, 24 h after carrageenan injection. In a mouse collagen induced arthritis model, chicory extract (200 mg/kg) reduced paw edema by 71% while the extract was being administered, and 31% 48 h after extract administration was discontinued. Two possible modes of action were investigated, pro-inflammatory gene expression and nitric oxide production by LPS-elicited macrophages. Chicory root extract down-regulated COX-2, TNF-α, IL1β, and iNOS expression and reduced nitric oxide production in a dose dependant manner. Several compounds were isolated from the chicory extract and tested in vitro to confirm activity. Dihydrolactucopicrin and 8-deoxylactucin showed particularly high nitric oxide inhibitory activity (IC50 = 13 μM for both). Dihydrolactucopicrin also was shown to down-regulate pro-inflammatory gene expression. These data demonstrate that chicory extracts rich in sesquiterpene lactones have potent anti-inflammatory activity with potential therapeutic use.
Spirostanol Saponins from Asparagus sprengeri and Their Molluscicidal Activity
Authors: Mohamed Mona A.
Published: March 2019

Two new spirostane saponins namely (25 R)-6α-[(β-D-glucopyranosyl)oxy]-5α-spirostan-3β-yl β-D-galactopyranoside (1) and (25 R)-6α-[(β-D-glucopyranosyl)oxy]-27-hydroxy-5α-spirostan-3β-yl β-D-glucopyranoside (2), together with three known metabolites (25 S)-5β-spirostan-3-β-yl O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (3), (25 R)-5α-spirostan-3-β-yl O-β-D-galactopyranosyl-(1→2)- O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (4) and (25 R)-5α-spirostan-3-β-yl O-β-D-glucopyranosyl-(1→3)- O-[β-D-xylopyranosyl-(1→2)]- O-β-D-glucopyranosyl-(1→4)-β-D-glactopyranoside (5) were identified from the leaves of Asparagus sprengeri Regel (Asparagaceae). Determination of the structures was based on chemical and spectroscopic data (HRESI-MS/MSn, 1H, DEPT 13C NMR, 1H-1H COSY, HSQC and HMBC). The dry powder, the 1-butanol extract of the leaves, and the isolated compounds (3–5) exhibited molluscicidal properties against Biomphalaria alexandrina snails (the intermediate host of Schistosoma mansoni) [LC90 = 150, 40, 7, 10 and 13 ppm, respectively], while compounds 1 and 2 were molluscicidally inactive.
Phytoecdysteroids in the Genus Microsorum (Polypodiaceae) of French Polynesia
Authors: Ho Raimana , Teai Taivini , Loquet Denis , Bianchini Jean-Pierre , Girault Jean-Pierre , Lafont René , Raharivelomanana Phila
Published: March 2019

A chemical survey of the six species of Microsorum in French Polynesia has been performed to determine and quantify the phytoecdysteroids. The content and composition of these compounds in the fronds of each of the six species were established. The highest concentrations of ecdysteroids were found in M. membranifolium (1.6% w/w) and M. scolopendria (0.47%), used in Polynesian traditional medicine. Seven phytoecdysteroids were quantified in these species and the major components were ecdysone, 20-hydroxyecdysone, and 2-deoxy-20-hydroxyecdysone, besides the minor ones (inokosterone, makisterone A, makisterone C, and 2-deoxyecdysone). Both the fronds of M. membranifolium and the rhizomes of M. scolopendria grown in French Polynesia could be considered as uncommonly rich sources of ecdysteroids.
Coumestoside A, Coumestoside B and Erythrodiside A, Three Glycosides from Cylicodiscus gabunensis (Mimmosaceae)
Authors: Kouam Jacques , Tane Pierre , Alain Meli Lanang , Noundou Xavier Siwe , Choudhary Muhammad Iqbal , Fomum Zacharias Tanee
Published: March 2019

Chemical analysis of the stem bark of Cylicodiscus gabunensis (Mimosaceae) yielded, in addition to the known eryhrodiol (4) and sojagol (IV) (5), three new glycosides designated coumestoside A (1), coumestoside B (2) and erythrodiside A (3). Their structures were established by chemical and spectroscopic means as 9- O-β-D-glucopyranosyl-4-hydroxycoumestrol, 9- O-α-L-rhamnopyranosyl-4-hydroxycoumestrol and 3- O-α-L-rhamnopyranosylerythrodiol-28- O-β-D-galactopyranoside, respectively.