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Acetogenins

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https://www.readbyqxmd.com/read/28626912/structural-characterisation-of-acetogenins-from-annona-muricata-by-supercritical-fluid-chromatography-coupled-to-high-resolution-tandem-mass-spectrometry
#1
Laurent Laboureur, Natacha Bonneau, Pierre Champy, Alain Brunelle, David Touboul
INTRODUCTION: Acetogenins are plant polyketides known to be cytotoxic and proposed as antitumor candidates. They are also suspected to be alimentary neurotoxins. Their occurrence as complex mixtures renders their dereplication and structural identification difficult using liquid chromatography coupled to tandem mass spectrometry and efforts are required to improve the methodology. OBJECTIVE: To develop a supercritical fluid chromatography (SFC) high-resolution tandem mass spectrometry method, involving lithium post-column cationisation, for the structural characterisation of Annonaceous acetogenins in crude extracts...
June 19, 2017: Phytochemical Analysis: PCA
https://www.readbyqxmd.com/read/28554707/squamocin-an-annonaceous-acetogenin-enhances-naphthalene-degradation-mediated-by-bacillus-atrophaeus-cn4
#2
Eduardo A Parellada, Mercedes Igarza, Paula Isacc, Alicia Bardón, Marcela Ferrero, Keshav Lalit Ameta, Adriana Neske
Squamocin belongs to a group of compounds called annonaceous acetogenins. They are secondary products of Annonaceae metabolism and can be isolated from Annona cherimolia seeds. This paper deals with the stimulation of biofilm formation of Bacillus atrophaeus CN4 by employing low squamocin concentrations to increase naphthalene degradation. Bacillus atrophaeus CN4, isolated from contaminated soil, has the ability to degrade naphthalene as the only source of carbon and energy. In the absence of additional carbon sources, the strain removed 69% of the initial concentration of naphthalene (approx...
May 26, 2017: Revista Argentina de Microbiología
https://www.readbyqxmd.com/read/28505125/isolaurenidificin-and-bromlaurenidificin-two-new-c15-acetogenins-from-the-red-alga-laurencia-obtusa
#3
Nahed O Bawakid, Walied M Alarif, Najla A Alburae, Hajer S Alorfi, Khalid O Al-Footy, Sultan S Al-Lihaibi, Mohamed A Ghandourah
Chromatographic fractionation of the CH₂Cl₂/MeOH extract of the Red Sea red alga Laurencia obtusa gave two new hexahydrofuro[3,2-b]furan-based C15-acetogenins, namely, isolaurenidificin (1) and bromlaurenidificin (2). The chemical structures were elucidated based on extensive analyses of their spectral data. Compounds 1 and 2 showed no toxicity (LC50 > 12 mM) using Artemia salina as test organism. Both compounds showed weak cytotoxicity against A549, HepG-2, HCT116, MCF-7, and PC-3 cells, however, they exhibited a relatively potent cytotoxic activity against peripheral blood neutrophils...
May 15, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28492496/chemical-composition-of-laurencia-obtusa-extract-and-isolation-of-a-new-c15-acetogenin
#4
Hélène Esselin, Sylvain Sutour, Joana Liberal, Maria Teresa Cruz, Ligia Salgueiro, Benjamin Siegler, Ingrid Freuze, Vincent Castola, Mathieu Paoli, Ange Bighelli, Félix Tomi
A new C15-acetogenin, sagonenyne (20), exhibiting an unusual single tetrahydropyran ring was isolated from an ethyl acetate extract of Laurencia obtusa collected on the Corsican coastline. Its structure was established by detailed NMR spectroscopic analysis, mass spectrometry, and comparison with literature data. Twenty-three known compounds were identified in the same extract by means of column chromatography steps, using a (13)C-NMR computer aided method developed in our laboratory. In addition to sesquiterpenes, which represent the main chemical class of this extract, diterpenes, sterols, and C15-acetogenins were identified...
May 11, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/28487731/the-value-of-caspase-3-after-the-application-of-annona-muricata-leaf-extract-in-colo-205-colorectal-cancer-cell-line
#5
Murdani Abdullah, Ari Fahrial Syam, Sofy Meilany, Bayu Laksono, Oryza Gryagus Prabu, Heri Setiyo Bekti, Lili Indrawati, Dadang Makmun
Annona muricata, commonly known as soursop, contains annonacin, acetogenin, and polyphenol which are known to have chemopreventive effects on cancer. In this study, we tend to evaluate the apoptosis-inducing effect of soursop (Annona muricata) leaf extract on the colorectal cancer cell line COLO-205 through the activities of caspase-3 which is a marker of cell apoptosis. Cell cultures were incubated with soursop leaf with a concentration of 10 μg/ml and then compared with those of the incubated positive control leucovorin 10 μg/ml and placebo as a negative control...
2017: Gastroenterology Research and Practice
https://www.readbyqxmd.com/read/28416750/annonaceous-acetogenins-mediated-up-regulation-of-notch2-exerts-growth-inhibition-in-human-gastric-cancer-cells-in-vitro
#6
Yan Li, Jianbin Ye, Zhongbiao Chen, Junjie Wen, Fei Li, Pengpeng Su, Yanqing Lin, Bingxin Hu, Danlin Wu, Lijun Ning, Qi Xue, Hongxiang Gu, Yunshan Ning
BACKGROUND: Gastric cancer (GC) is a global health problem because of limited treatments and poor prognosis. Annonaceous acetogenins (ACGs) has been reported to exert anti-tumorigenic effects in cancer, yet the mechanism underlying its effects on GC remains largely unknown. Notch signaling plays a critical role in cell proliferation, differentiation and apoptosis. Therefore, it may contribute to the development of GC. This study aims to explore the role of Notch2 in ACGs' activities in GC cells...
March 28, 2017: Oncotarget
https://www.readbyqxmd.com/read/28415154/annona-species-annonaceae-a-rich-source-of-potential-antitumor-agents
#7
REVIEW
Rosa Tundis, Jianbo Xiao, Monica R Loizzo
Plants have provided the basis of traditional medicine systems throughout the world for thousands of years and continue to yield molecules for new remedies. We analyzed studies published from 2009 to 2016 on the Annona species (Annonaceae), including A. coriacea, A. crassifolia, A. hypoglauca, A. muricata, A. squamosa, A. sylvatica, and A. vepretorum, as sources of potential antitumor agents. Here, we report and discuss the mechanisms of action and structure-activity relationships of the most active Annona constituents...
April 17, 2017: Annals of the New York Academy of Sciences
https://www.readbyqxmd.com/read/28353149/toxicity-of-an-annonin-based-commercial-bioinsecticide-against-three-primary-pest-species-of-stored-products
#8
L P Ribeiro, O Z Zanardi, G L P Gonçalves, T F Ansante, P T Yamamoto, J D Vendramim
The effects of a bioinsecticide formulation based on extract of Annona squamosa L. (Annonaceae) containing 10,000 mg L(-1) of acetogenin annonin as the main active ingredient were investigated against three primary pest species of stored grains in Brazil [maize weevil Sitophilus zeamais Motschulsky (Coleoptera: Curculionidae), Mexican bean weevil Zabrotes subfasciatus (Boheman) (Coleoptera: Chrysomelidae: Bruchinae), and cowpea weevil Callosobruchus maculatus (Fabricius) (Coleoptera: Chrysomelidae: Bruchinae)] by means of residual contact bioassays...
March 28, 2017: Neotropical Entomology
https://www.readbyqxmd.com/read/28254016/the-fruit-of-annona-squamosa-l-as-a-source-of-environmental-neurotoxins-from-quantification-of-squamocin-to-annotation-of-annonaceous-acetogenins-by-lc-ms-ms-analysis
#9
Natacha Bonneau, Lamia Baloul, Idensi Bajin Ba Ndob, François Sénéjoux, Pierre Champy
Annonaceous acetogenins (AAGs) are neurotoxins possibly responsible for atypical Parkinsonism/dementia clusters, via the consumption of edible Annonaceae fruits. Their presence was investigated in fruit pulps of Annona squamosa from different locations. Qualitative analysis of other AAGs was performed. We here report the identification of squamocin in batches from Asia, the Caribbean Basin and the Indian Ocean. This molecule was quantified by HPLC-UV, evidencing a content of 13.5-36.4mg/fruit. HPLC-ESI-Q-TOF allowed the detection of 25 different raw formulas matching with AAGs...
July 1, 2017: Food Chemistry
https://www.readbyqxmd.com/read/28185724/simplifying-nature-towards-the-design-of-broad-spectrum-kinetoplastid-inhibitors-inspired-by-acetogenins
#10
Eoin R Gould, Elizabeth F B King, Stefanie K Menzies, Andrew L Fraser, Lindsay B Tulloch, Marija K Zacharova, Terry K Smith, Gordon J Florence
The need for new treatments for the neglected tropical diseases African sleeping sickness, Chagas disease and Leishmaniasis remains urgent with the diseases widespread in tropical regions, affecting the world's very poorest. We have previously reported bis-tetrahydropyran 1,4-triazole analogues designed as mimics of the annonaceous acetogenin natural product chamuvarinin, which maintained trypanocidal activity. Building upon these studies, we here report related triazole compounds with pendant heterocycles, mimicking the original butenolide of the natural product...
January 28, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28155166/a-histochemical-technique-for-the-detection-of-annonaceous-acetogenins
#11
Guillermo Laguna-Hernández, Alicia Enriqueta Brechú-Franco, Iván De la Cruz-Chacón, Alma Rosa González-Esquinca
Annonaceous acetogenins (ACGs) are molecules with carbon numbers C35-C37, usually with tetrahydrofuran and tetrahydropyran rings and one terminal γ-lactone (usually α,β-unsaturated), in a large aliphatic chain that is varyingly hydroxylated, acetoxylated or ketonized. ACGs have ecological functions as insecticides and are pharmacologically promising due to their cytotoxic and antitumoral properties. They are found in the seeds, leaves, roots, flowers and fruits of annonaceous plants and can be detected during isolation via thin-layer chromatography using Kedde's reagent, which reacts with the unsaturated lactone...
2017: Methods in Molecular Biology
https://www.readbyqxmd.com/read/28116099/a-novel-thiophene-3-carboxamide-analog-of-annonaceous-acetogenin-exhibits-antitumor-activity-via-inhibition-of-mitochondrial-complex-i
#12
Akinobu Akatsuka, Naoto Kojima, Mutsumi Okamura, Shingo Dan, Takao Yamori
Previously we synthesized JCI-20679, a novel thiophene-3-carboxamide analog of annonaceous acetogenins which have shown potent antitumor activity, with no serious side effects, in mouse xenograft models. In this study, we investigated the antitumor mechanism of JCI-20679. The growth inhibition profile (termed "fingerprint") of this agent across a panel of 39 human cancer cell lines (termed "JFCR39") was measured; this fingerprint was analyzed by the COMPARE algorithm utilizing the entire drug sensitivity database for the JFCR39 panel...
August 2016: Pharmacology Research & Perspectives
https://www.readbyqxmd.com/read/28092423/-1-h-qnmr-quantification-of-annonaceous-acetogenins-in-crude-extracts-of-annona-muricata-l-fruit-pulp
#13
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
#14
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
#15
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
#16
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
#17
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
#18
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
#19
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
#20
K Mulia, F Fauzia, E Krisanti, A Faried
No abstract text is available yet for this article.
December 2016: Planta Medica
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