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Acetogenins

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https://www.readbyqxmd.com/read/28092423/-1-h-qnmr-quantification-of-annonaceous-acetogenins-in-crude-extracts-of-annona-muricata-l-fruit-pulp
#1
Natacha Bonneau, Timothé Cynober, Jean-Christophe Jullian, Pierre Champy
INTRODUCTION: Annonaceous acetogenins (AAGs) constitute a group of environmental neurotoxins, possibly implicated in sporadic atypical Parkinsonism/dementia complexes. The recent evidencing of complex mixtures of AAGs in edible fruits and derived food products requires efficient and practical analytical tools for an estimation of human exposure. OBJECTIVE: To develop a simple method for the direct quantitation of the majority of AAGs (sub-types 1a and 1b) within crude extracts, using commonly available (1) H-NMR spectrometers, for food control...
January 16, 2017: Phytochemical Analysis: PCA
https://www.readbyqxmd.com/read/28079013/natural-product-inhibitors-of-topoisomerases-review-and-docking-study
#2
L Scotti, F J B Mendonça Júnior, F F Ribeiro, J F Tavares, M S Da Silva, J M Barbosa Filho, M T Scotti
Since ancient times, natural products have been used in treating various diseases effectively and safely. Nowadays, these natural compounds are submitted to sophisticated methodologies from isolation, computing, analytical, and even serving as pharmacophore suggestions for synthesis. The substances extracted from marine species, plants, and microorganisms present activities beneficial to our health, including protection against malignant tumors. The topoisomerase enzymes play an important role in DNA metabolism, and searching for enzyme inhibitors is an important target in the search for new anticancer drugs...
January 11, 2017: Current Protein & Peptide Science
https://www.readbyqxmd.com/read/28070565/activation-of-respiratory-complex-i-from-escherichia-coli-studied-by-fluorescent-probes
#3
Nikolai Belevich, Galina Belevich, Zhiyong Chen, Subhash C Sinha, Marina Verkhovskaya
Respiratory Complex I from E. coli may exist in two interconverting forms: resting (R) and active (A). The R/A transition of purified, solubilized Complex I occurring upon turnover was studied employing two different fluorescent probes, Annine 6+, and NDB-acetogenin. NADH-induced fluorescent changes of both dyes bound to solubilized Complex I from E. coli were characterized as a function of the protein:dye ratio, temperature, ubiquinone redox state and the enzyme activity. Analysis of this data combined with time-resolved optical measurements of Complex I activity and spectral changes indicated two ubiquinone-binding sites; a possibility of reduction of the tightly-bound quinone in the resting state and reduction of the loosely-bound quinone in the active state is discussed...
January 2017: Heliyon
https://www.readbyqxmd.com/read/28064519/three-new-antitumor-annonaceous-acetogenins-from-the-seeds-of-annona-squamosa
#4
Chengyao Ma, Qiwen Wang, Yeye Shi, Yue Li, Xunan Wang, Xiang Li, Yong Chen, Jianwei Chen
Two new annonaceous acetogenins squamocin P (2) and annosquatin III (3) and one new ACG precursor dieporeticenin B (1) along with five known precursors (4-8) were isolated from the seeds of Annona squamosa. Their structures were ascertained by chemical methods and various spectral evidences. These compounds showed inhibitory effects against three multidrug-resistant (MDR) cancer cell lines. Compound 2 and 3 displayed selective cytotoxicity against SMMC 7721/T (IC50 0.435 and 1.79 μM) and MCF-7/ADR (IC50 values 3...
January 9, 2017: Natural Product Research
https://www.readbyqxmd.com/read/28043557/antimycobacterial-potency-and-cytotoxicity-study-of-three-medicinal-plants
#5
Patrick Valere Tsouh Fokou, Regina Appiah-Opong, Dorothy Yeboah-Manu, Abena Adomah Kissi-Twum, Lauve Rachel Tchokouaha Yamthe, Aristide Laurel Mokale Kognou, Phyllis Addo, Fabrice Fekam Boyom, Alexander Kwadwo Nyarko
OBJECTIVE/BACKGROUND: Mycobacterial infections including tuberculosis, leprosy, and buruli ulcer are among the most prevalent, debilitating, and deadly tropical diseases, especially in Sub-Saharan Africa. The development of drug resistance to the currently available drugs and the poor compliance emphasize the need for new chemotherapeutic agents. This study was designed to evaluate the in vitro activity of Cleistopholis patens, Annona reticulata, and Greenwayodendron suaveolens against Mycobacterium smegmatis...
December 2016: International Journal of Mycobacteriology
https://www.readbyqxmd.com/read/28000792/mechanistic-study-of-tetrahydrofuran-acetogenins-in-triggering-endoplasmic-reticulum-stress-response-apotoposis-in-human-nasopharyngeal-carcinoma
#6
Shin-Hun Juang, Chang-Ying Chiang, Fong-Pin Liang, Hsiu-Hui Chan, Jai-Sing Yang, Shih-Hao Wang, Yu-Chin Lin, Ping-Chung Kuo, Meng-Ru Shen, Tran Dinh Thang, Bui Thi Minh Nguyet, Sheng-Chu Kuo, Tian-Shung Wu
For past three decades, numerous studies have elucidated the antiproliferative effects of acetogenins in hopes of developing a new class of clinical anticancer agents. However, clear and definitive action mechanisms of acetogenins were less clarified. In the present study, three tetrahydrofuran (THF)-containing acetogenins were found to have potent and selective antiproliferative activity against human nasopharyngeal carcinoma (NPC) cell lines and their methotrexate-resistant counterparts. The THF-containing acetogenins induced G2/M phase arrest, mitochondrial damage and apoptosis, and increased cytosolic and mitochondrial Ca(2+) in NPCs...
December 21, 2016: Scientific Reports
https://www.readbyqxmd.com/read/27976249/quantification-of-the-neurotoxins-annonaceous-acetogenins-in-the-edible-fruits-of-several-annona-species-using-1h-nmr
#7
N Bonneau, T Cynober, P Coulerie, V Kagy, P Champy
No abstract text is available yet for this article.
December 2016: Planta Medica
https://www.readbyqxmd.com/read/27975649/chitosan-tripolyphosphate-microparticles-for-controlled-release-of-acetogenins-extracted-from-annona-muricata-leaves
#8
K Mulia, F Fauzia, E Krisanti, A Faried
No abstract text is available yet for this article.
December 2016: Planta Medica
https://www.readbyqxmd.com/read/27975485/annonaceous-acetogenins-from-the-fruit-pulps-of-annona-reticulata-and-a-squamosa-dereplicative-studies
#9
N Bonneau, P Champy
No abstract text is available yet for this article.
December 2016: Planta Medica
https://www.readbyqxmd.com/read/27876785/characterization-of-the-annonaceous-acetogenin-annonacinone-a-natural-product-inhibitor-of-plasminogen-activator-inhibitor-1
#10
Stéphane Pautus, Mouad Alami, Fréderic Adam, Guillaume Bernadat, Daniel A Lawrence, Allan De Carvalho, Gilles Ferry, Alain Rupin, Abdallah Hamze, Pierre Champy, Natacha Bonneau, Philippe Gloanec, Jean-Louis Peglion, Jean-Daniel Brion, Elsa P Bianchini, Delphine Borgel
Plasminogen activator inhibitor-1 (PAI-1) is the main inhibitor of the tissue type and urokinase type plasminogen activators. High levels of PAI-1 are correlated with an increased risk of thrombotic events and several other pathologies. Despite several compounds with in vitro activity being developed, none of them are currently in clinical use. In this study, we evaluated a novel PAI-1 inhibitor, annonacinone, a natural product from the Annonaceous acetogenins group. Annonacinone was identified in a chromogenic screening assay and was more potent than tiplaxtinin...
November 23, 2016: Scientific Reports
https://www.readbyqxmd.com/read/27871119/inhibitory-activity-of-avocado-seed-fatty-acid-derivatives-acetogenins-against-listeria-monocytogenes
#11
Carmen Salinas-Salazar, Carmen Hernández-Brenes, Dariana Graciela Rodríguez-Sánchez, Elena Cristina Castillo, Jesús Manuel Navarro-Silva, Adriana Pacheco
High standards regarding Listeria monocytogenes control and consumer demands for food products without synthetic additives represent a challenge to food industry. We determined the antilisterial properties of an enriched acetogenin extract (EAE) from avocado seed, compared it to two commercial antimicrobials (one enriched in avocado acetogenins), and tested purified molecules. Acetogenin composition in pulp and seed of Hass avocado was quantified. EAE were obtained by two sequential centrifuge partition chromatography separations and molecules purified by preparative chromatography and quantified by HPLC-MS-TOF and HPLC-PDA...
January 2017: Journal of Food Science
https://www.readbyqxmd.com/read/27813410/total-synthesis-of-the-proposed-structure-for-aromin-and-its-structural-revision
#12
Shunya Takahashi, Daisuke Satoh, Misato Hayashi, Kohta Takahashi, Kazunori Yamaguchi, Takemichi Nakamura, Hiroyuki Koshino
This paper describes the first total synthesis of the proposed structure for aromin, an annonaceous acetogenin possessing an unusual bis-THF ring system, and its 4S,7R-isomer. The key steps involve an oxidative cyclization of a couple of terminal-diene alcohols and an intermolecular metathesis of an alkenyl tetrahydrofuran with an enone carrying a tetrahydrofuranyl lactone. The spectral data of both samples did not match those of aromin. Re-examination of the NMR data using the CAST/CNMR Structure Elucidator and chemical derivations suggested that the real structure of aromin should be revised to be a tetrahydropyran acetogenin, montanacin D...
November 18, 2016: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/27704814/epimeric-face-selective-oxidations-and-diastereodivergent-transannular-oxonium-ion-formation-fragmentations-computational-modeling-and-total-syntheses-of-12-epoxyobtusallene-iv-12-epoxyobtusallene-ii-obtusallene-x-marilzabicycloallene-c-and-marilzabicycloallene
#13
James Clarke, Karl J Bonney, Muhammad Yaqoob, Savade Solanki, Henry S Rzepa, Andrew J P White, David S Millan, D Christopher Braddock
The total syntheses of 12-epoxyobtusallene IV, 12-epoxyobtusallene II, obtusallene X, marilzabicycloallene C, and marilzabicycloallene D as halogenated C15-acetogenin 12-membered bicyclic and tricyclic ether bromoallene-containing marine metabolites from Laurencia species are described. Two enantiomerically pure C4-epimeric dioxabicyclo[8.2.1]tridecenes were synthesized by E-selective ring-closing metathesis where their absolute stereochemistry was previously set via catalytic asymmetric homoallylic epoxidation and elaborated via regioselective epoxide-ring opening and diastereoselective bromoetherification...
October 21, 2016: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/27569447/chronic-consumption-of-annona-muricata-juice-triggers-and-aggravates-cerebral-tau-phosphorylation-in-wild-type-and-mapt-transgenic-mice
#14
Robert Rottscholl, Marlen Haegele, Britta Jainsch, Hong Xu, Gesine Respondek, Matthias Höllerhage, Thomas W Rösler, Emilie Bony, Jessica Le Ven, Vincent Guérineau, Isabelle Schmitz-Afonso, Pierre Champy, Wolfgang H Oertel, Elizabeth S Yamada, Günter U Höglinger
In the pathogenesis of tauopathies, genetic and environmental factors have been identified. While familial clustering led to the identification of mutations in MAPT encoding the microtubule-associated protein tau, the high incidence of a sporadic tauopathy endemic in Guadeloupe was linked to the plant-derived mitochondrial complex I inhibitor annonacin. The interaction of both factors was studied in the present work in a realistic paradigm over a period of 12 months. Mice over-expressing either human wild-type tau or R406W mutant tau as well as non-transgenic mice received either regular drinking water or commercially available tropical fruit juice made of soursop (Annona muricata L...
November 2016: Journal of Neurochemistry
https://www.readbyqxmd.com/read/27566205/antitumor-activity-of-annona-squamosa-seed-oil
#15
Yong Chen, Yayun Chen, Yeye Shi, Chengyao Ma, Xunan Wang, Yue Li, Yunjie Miao, Jianwei Chen, Xiang Li
CONTEXT: Custard apple (Annona squamosa Linn.) is an edible tropical fruit, and its seeds have been used to treat "malignant sore" (cancer) and other usage as insecticide. A comparison of extraction processes, chemical composition analysis and antitumor activity of A. squamosa seed oil (ASO) were investigated. MATERIALS AND METHODS: The optimal extraction parameters of ASO were established by comparing percolation, soxhlet, ultrasonic and SFE-CO2 extraction methods...
December 4, 2016: Journal of Ethnopharmacology
https://www.readbyqxmd.com/read/27564691/modular-and-stereodivergent-approach-to-unbranched-1-5-9-n-polyenes-total-synthesis-of-chatenaytrienin-4
#16
Juliane Adrian, Christian B W Stark
An iterative strategy for the stereodivergent synthesis of unbranched 1,5,9,n-polyenes (and -polyynes) was investigated. Starting from a terminal alkyne the iteration cycle consists of a C3 extension (allylation), a chemoselective hydroboration, an alkyne reduction, and an oxidation of the associated alcohol with subsequent C1 homologation. Double bond geometry is controlled using stereoselective alkyne reductions, employing either the Lindlar hydrogenation protocol or an aluminum hydride reduction. In a model sequence it was demonstrated that the strategy is applicable to the synthesis of 1,5,9,n-polyenes with any possible double bond configuration accessible in equally high efficiency and selectivity...
September 16, 2016: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/27551943/substrate-controlled-asymmetric-total-synthesis-and-structure-revision-of-bisezakyne-a
#17
Iljin Shin, Dongjoo Lee, Hyoungsu Kim
The first asymmetric total synthesis and subsequent structure revision of (-)-bisezakyne A, a Laurencia C15 acetogenin from Alpysia oculifera, has been accomplished. Our substrate-controlled synthesis of this oxolane natural product features a highly stereoselective "protecting-group-dependent" intramolecular amide enolate alkylation strategy for the synthesis of the key 9,10-trans-9,12-cis-10-hydroxytetrahydrofuran intermediate through "nonchelate" control. In addition, our synthesis determined the absolute configuration of the halogenated marine natural product...
September 2, 2016: Organic Letters
https://www.readbyqxmd.com/read/27533261/short-route-to-the-total-synthesis-of-natural-muricadienin-and-investigation-of-its-cytotoxic-properties
#18
Usein M Dzhemilev, Vladimir A D'yakonov, Regina A Tuktarova, Lilya U Dzhemileva, Svetlana R Ishmukhametova, Milyausha M Yunusbaeva, Armin de Meijere
An original synthesis of the acetogenin muricadienin, the bioprecursor of solamin, has been developed. The key step in the five-step 41% overall yield synthesis is the catalytic cross-cyclomagnesiation reaction of functionally substituted 1,2-dienes with EtMgBr in the presence of Cp2TiCl2 and magnesium metal. It has been demonstrated for the first time that muricadienin exhibits a moderate in vitro inhibitory activity against topoisomerases I and IIα, key cell cycle enzymes. Using flow cytometry, muricadienin was shown to have high cytotoxicity toward the HEK293 kidney cancer cells (IC50 0...
August 26, 2016: Journal of Natural Products
https://www.readbyqxmd.com/read/27532504/multiple-modes-of-action-of-the-squamocin-in-the-midgut-cells-of-aedes-aegypti-larvae
#19
Marilza da Silva Costa, Sérgio Oliveira de Paula, Gustavo Ferreira Martins, José Cola Zanuncio, Antônio Euzébio Goulart Santana, José Eduardo Serrão
Annonaceous acetogenins are botanical compounds with good potential for use as insecticides. In the vector, Aedes aegypti (L.) (Diptera: Culicidae), squamocin (acetogenin) has been reported to be a larvicide and cytotoxic, but the modes of action of this molecule are still poorly understood. This study evaluated the changes in the cell morphology, and in the expression of genes, for autophagy (Atg1 and Atg8), for membrane ion transporter V-ATPase, and for water channel aquaporin-4 (Aqp4) in the midgut of A...
2016: PloS One
https://www.readbyqxmd.com/read/27486323/annonaceous-acetogenins-nanosuspensions-stabilized-by-pcl-peg-block-polymer-significantly-improved-antitumor-efficacy
#20
Jingyi Hong, Yanhong Li, Yijing Li, Yao Xiao, Haixue Kuang, Xiangtao Wang
Annonaceous acetogenins (ACGs) have shown superior antitumor activity against a variety of cancer cell lines, but their clinical application has been limited by their poor solubility. In this study, ACGs-nanosuspensions (NSps) were successfully prepared by a precipitation ultrasonic method using monomethoxypoly (ethylene glycol)2000-poly (ε-caprolactone)2000 (mPEG2000-PCL2000) as a stabilizer. The resultant ACGs-NSps had a mean particle size of 123.2 nm, a zeta potential of -20.17 mV, and a high drug payload of 73...
2016: International Journal of Nanomedicine
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