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Jin-Sik Nam, Seo-Yeon Park, Hyo-Jeong Lee, Seon-Ok Lee, Hye-Lim Jang, Young Ha Rhee
Pawpaw (Asimina triloba [L.] Dunal) is widely cultivated in Korea for its fruit, which contains bioactive compounds, such as acetogenins. In this study, we investigated the acetogenin content and antiproliferative activity of pawpaw fruit pulp against various cancer cell lines and evaluated the relationship between these two variables at different maturation stages. Unripe fruit had higher antiproliferative activity than ripe fruit, and the activity level depended on acetogenin content. In addition, the presence of specific acetogenins was related to inhibition of certain cancer cell types...
April 16, 2018: Journal of Food Science
Haowen Li, Yijing Li, Hui Ao, Dongdong Bi, Meihua Han, Yifei Guo, Xiangtao Wang
Annonaceous acetogenins (ACGs) are one of the most active constituents isolated from Annona species with potent antitumor activity. However, the poor solubility and severe side effect greatly limit their use in clinic. In this study, folic acid (FA) modified annonaceous acetogenins nanosuspensions (FA-PEG-ACGs-NSps) had been successfully prepared using DSPE-PEG-FA and soybean lecithin (SPC) as stabilizers. The resultant FA-PEG-ACGs-NSps had a mean particle size of 119.7 nm, a zeta potential of -23.0 mV and a high drug payload of 49...
November 2018: Drug Delivery
Hélène Esselin, Félix Tomi, Ange Bighelli, Sylvain Sutour
The chemical investigation of an ethyl acetate extract (EtOAc) obtained from Laurencia obtusa , collected in Corsica, allowed for the identification of three new compounds ( 1 , 2 , and 4 ) and six known compounds. Compounds 1 to 4 were isolated and fully characterized by a detailed spectroscopic analysis. Compounds 1 and 2 are two C15 -acetogenins sharing the same ring system: a tetrahydropyran linked by a methylene to a tetrahydrofuran ring. Compound 1 exhibits a bromoallene unit whereas compound 2 possesses an uncommon α-bromo-α,β-unsaturated aldehyde terminal unit...
March 21, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Muhammad Fiaz, Luis Carlos Martínez, Marilza da Silva Costa, Jamile Fernanda Silva Cossolin, Angelica Plata-Rueda, Wagner Gonzaga Gonçalves, Antônio Euzébio Goulart Sant'Ana, José Cola Zanuncio, José Eduardo Serrão
Annonaceous acetogenins (Annona squamosa Linnaeus) comprises of a series of natural products which are extracted from Annonaceae species, squamocin proved to be highly efficient among those agents. Squamocin is mostly referred as a lethal agent for midgut cells of different insects, with toxic effects when tested against larva of some insects. In present study, LC50 and LC90 of squamocin for A. gemmatalis Hübner (Lepidoptera: Noctuidae) were calculated using probit analysis. Morphological changes in midgut cells were analyzed under light, fluorescence and transmission electron microscopes when larvae were treated with LC50 and LC90 of squamocin for 24, 48 and 72 h...
March 7, 2018: Ecotoxicology and Environmental Safety
Asif Khurshid Qazi, Jawed A Siddiqui, Rahat Jahan, Sanjib Chaudhary, Larry A Walker, Zafar Syed, Dwight T Jones, Surinder K Batra, Muzafar A Macha
Cancer remains a leading cause of death in the United States and around the world. Although the current synthetic inhibitors used in targeted therapies have improved patient prognosis, toxicity and development of resistance to these agents remain a challenge. Plant-derived natural products and their derivatives have historically been used to treat various diseases, including cancer. Several leading chemotherapeutic agents are directly or indirectly based on botanical natural products. Beyond these important drugs, however, a number of crude herbal or botanical preparations have also shown promising utility for cancer and other disorders...
February 15, 2018: Carcinogenesis
Noraziah Nordin, Nazia Abdul Majid, Rozana Othman, Fatima Abdelmutaal Ahmed Omer, Muhammad Nazil Afiq Nasharuddin, Najihah Mohd Hashim
Plagioneurin B belongs to acetogenin group has well-established class of compounds. Acetogenin group has attracted worldwide attention in the past few years due their biological abilities as inhibitors for several types of tumour cells. Plagioneurin B was isolated via conventional chromatography and tested for thorough mechanistic apoptosis activity on human ovarian cancer cells (CAOV-3). Its structure was also docked at several possible targets using Autodock tools software. Our findings showed that plagioneurin B successfully inhibits the growth of CAOV-3 cells at IC50 of 0...
February 12, 2018: Apoptosis: An International Journal on Programmed Cell Death
Sylvain Sutour, Bruno Therrien, Stephan H von Reuss, Félix Tomi
NMR chemical profiling of a Laurenciella sp. using a computerized method developed in our laboratory resulted in the identification of five new compounds (1-5) and 17 known compounds, among which 3-(E)-laurenyne represented by far the most abundant metabolite. Compounds 1 to 5 were isolated and fully characterized by detailed spectroscopic analysis. The absolute configuration and structural features of compound 1 were determined by single-crystal X-ray diffraction analysis. Compounds 1 to 4 are 12-membered cyclic ether acetogenins that are present in solution as interconverting conformers exhibiting an (aR) configuration of the bromoallene unit together with an S configuration at C-4...
January 30, 2018: Journal of Natural Products
Adrián Morales-Amador, Caterina R de Vera, Olivia Márquez-Fernández, Antonio Hernández Daranas, José M Padrón, José J Fernández, María L Souto, Manuel Norte
Red algae of Laurencia continue to provide wide structural diversity and complexity of halogenated C15 acetogenin medium-ring ethers. Here, we described the isolation of three new C15 acetogenins ( 3 - 5 ), and one truncated derivative ( 6 ) from Laurencia viridis collected on the Canary Islands. These compounds are interesting variations on the pinnatifidenyne structure that included the first examples of ethynyl oxirane derivatives ( 3 - 4 ). The structures were elucidated by extensive study of NMR (Nuclear Magnetic Resonance) data, J -based configuration analysis and DFT (Density Functional Theory) calculations...
December 29, 2017: Marine Drugs
Takashi Kamada, Chin-Soon Phan, Charles S Vairappan
Two new halogenated nonterpenoids C15 -acetogenins, nangallenes A-B (1-2), together with two known halogenated compounds itomanallene A (3) and 2,10-dibromo-3-chloro-α-chamigrene (4), were isolated and identified from the organic extract of the marine red alga Laurencia nangii Masuda collected from the coastal waters in Semporna, Borneo. Their structures were established by means of spectroscopic analysis including IR, high-resolution electrospray ionization mass spectrometry (HRESI-MS), and 1D and 2D NMR techniques...
December 27, 2017: Journal of Asian Natural Products Research
Mohamad Norisham Mohamad Rosdi, Shahkila Mohd Arif, Mohamad Hafizi Abu Bakar, Siti Aisyah Razali, Razauden Mohamed Zulkifli, Harisun Ya'akob
Annona muricata Linn or usually identified as soursop is a potential anticancer plant that has been widely reported to contain valuable chemopreventive agents known as annonaceous acetogenins. The antiproliferative and anticancer activities of this tropical and subtropical plant have been demonstrated in cell culture and animal studies. A. muricata L. exerts inhibition against numerous types of cancer cells, involving multiple mechanism of actions such as apoptosis, a programmed cell death that are mainly regulated by Bcl-2 family of proteins...
January 2018: Apoptosis: An International Journal on Programmed Cell Death
F Corrales Chahar, S B Díaz, A Ben Altabef, C Gervasi, P E Alvarez
In this paper we study the interactions of two biomolecules (ascorbic acid and Annonacin) with a bilayer lipid membrane. Egg yolk phosphatidylcholine (eggPC) liposomes (in crystalline liquid state) were prepared in solutions of ascorbic acid (AA) at different concentration levels. On the other hand, liposomes were doped with Annonacin (Ann), a mono-tetrahydrofuran acetogenin (ACG), which is an effective citotoxic substance. While AA pharmacologic effect and action mechanisms are widely known, those of Ann's are only very recently being studied...
January 2018: Chemistry and Physics of Lipids
Amalia B Gallardo, Mercedes Cueto, Ana R Díaz-Marrero, José M de la Rosa, Victor Fajardo, Aurelio San-Martín, José Darias
Ptilonines A-F, pyranosylmagellanicus D-E and magellenediol are previously undescribed acetogenins isolated from the red alga Ptilonia magellanica. Their structures were determined from spectroscopic evidence. The absolute configuration of the known pyranosylmagellanicus A, was established by derivatization with (R)- and (S)-α-methoxy -α-phenylacetic acids (MPA). Ptilonines exhibit an unusual halogenation pattern, that may confer evolutionary advantages to Ptilonia magellanica, for which a biogenetic origin is proposed...
January 2018: Phytochemistry
Daeyeon Jeong, Te-Ik Sohn, Jong Yup Kim, Gyudong Kim, Deukjoon Kim, Robert S Paton
A highly efficient and stereoselective route to potential synthetic intermediates for ocellenyne and related C15 acetogenin natural products with 6,10-syn- and 6,10-anti-2,5-dioxabicyclo[2.2.1]heptane core structures has been developed by means of an iterative biogenesis-inspired oxonium ion formation/fragmentation sequence. In accordance with chemical transformations, the most likely stereostructure for (E)-ocellenyne on the basis of GIAO (13)C NMR calculations possesses a 6,10-anti-2,5-dioxabicyclo[2.2.1]heptane core, as predicted from a plausible biosynthetic pathway, instead of the spectroscopically proposed 6,10-syn-2,5-dioxabicyclo[2...
November 17, 2017: Organic Letters
Ali Attiq, Juriyati Jalil, Khairana Husain
Inventories of tropical forests have listed Annonaceae as one of the most diverse plant families. For centuries, it is employed in traditional medicines to cure various pathological conditions including snakebite, analgesic, astringent, diarrhea, dysentery, arthritis pain, rheumatism, neuralgia, and weight loss etc. Phytochemical analysis of Annonaceae family have reported the occurrence of alkaloids, flavonoids, triterpenes, diterpenes and diterpene flavone glycosides, sterols, lignans, and annonaceous acetogenin characteristically affiliated with Annonaceae sp...
2017: Frontiers in Pharmacology
Hiroyoshi Takamura, Tomoya Katsube, Kazuki Okamoto, Isao Kadota
The first total synthesis of two possible diastereomers of natural 6-chlorotetrahydrofuran acetogenin 1 has been achieved. The synthetic route features 5-exo-tet cyclization, Z selective Wittig reaction and Julia olefination for the construction of conjugated diene and enyne moieties, and stereoselective chlorination. Comparison of their1 H and13 C NMR data and specific rotation with those of the natural product elucidated the absolute configuration of natural (-)-6-chlorotetrahydrofuran acetogenin 1.
December 6, 2017: Chemistry: a European Journal
Yahaya Gavamukulya, Fred Wamunyokoli, Hany A El-Shemy
Annona muricata (A. muricata) is a tropical plant species belonging to family Annonaceae and known for its many medicinal uses. This review focuses on the research history of its traditional uses, phytochemicals, pharmacological activities, toxicological aspects of the extracts and isolated compounds, as well as the in vitro propagation studies with the objective of stimulating further studies on this plant for human consumption and treatment. A. muricata extracts have been identified in tropical regions to traditionally treat diverse conditions ranging from fever to diabetes and cancer...
September 2017: Asian Pacific Journal of Tropical Medicine
Carlos Eduardo Rodríguez-López, Carmen Hernández-Brenes, Víctor Treviño, Rocío I Díaz de la Garza
BACKGROUND: Avocado fruit contains aliphatic acetogenins (oft-acetylated, odd-chain fatty alcohols) with promising bioactivities for both medical and food industries. However, we have scarce knowledge about their metabolism. The present work aimed to study changes in acetogenin profiles from mesocarp, lipid-containing idioblasts, and seeds from 'Hass' cultivar during fruit development, germination, and three harvesting years. An untargeted LC-MS based lipidomic analysis was also conducted to profile the lipidome of avocado fruit in each tissue...
September 29, 2017: BMC Plant Biology
Christian Anabí Riley-Saldaña, María Del Rocío Cruz-Ortega, Mariano Martínez Vázquez, Iván De-la-Cruz-Chacón, Marisol Castro-Moreno, Alma Rosa González-Esquinca
In plants, the presence and distribution of specialized metabolites during the early stages of development are not documented enough, even though their biosynthesis is one of the most important strategies for survival. In this study, five alkaloids and four acetogenins were detected in Annona muricata L. during early development seedling, including three phases of root emergence and three of seedling formation. Hexane and alkaloid extracts were obtained from each organ, which were analyzed in a gas-mass chromatograph and in a high-performance liquid chromatograph coupled with a photodiode array UV detector (HPLC-DAD)...
October 26, 2017: Zeitschrift Für Naturforschung. C, A Journal of Biosciences
Lindsay B Tulloch, Stefanie K Menzies, Andrew L Fraser, Eoin R Gould, Elizabeth F King, Marija K Zacharova, Gordon J Florence, Terry K Smith
Current drugs to treat African sleeping sickness are inadequate and new therapies are urgently required. As part of a medicinal chemistry programme based upon the simplification of acetogenin-type ether scaffolds, we previously reported the promising trypanocidal activity of compound 1, a bis-tetrahydropyran 1,4-triazole (B-THP-T) inhibitor. This study aims to identify the protein target(s) of this class of compound in Trypanosoma brucei to understand its mode of action and aid further structural optimisation...
September 2017: PLoS Neglected Tropical Diseases
Xu-Nan Wang, Xiang Li, Yong Chen, Yue Li
The present research was launched to investigate the effects of 12 annonaceous acetogenins (ACGs) on human hepatic carcinoma cell line SMMC-7721/ADR, and to find out their structure-activity relationship. SMMC-7721/ADR cells were treated with 12 ACGs including annosquamin A(1),annosquamin B(2),annotemoyin-1(3),uvariamicin Ⅱ(4),annosquacin D(5),annosquacin B(6),isodesacetyluvaricin(7),uvarigrandin A(8),squamostatin D(9),squamostatin E(10),squamostatin A(11),and 12,15-cis-squamostatin A(12) for 24 h, and the different expression of the target gene NDUFV2 were detected by quantitative real-time PCR...
July 2017: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
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