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Journal articles on the topic 'Cytotoxic lactones'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Huo, Jun, Sheng-Ping Yang, Jian Ding, and Jian-Min Yue. "Cytotoxic Sesquiterpene Lactones fromEupatoriumlindleyanum." Journal of Natural Products 67, no. 9 (2004): 1470–75. http://dx.doi.org/10.1021/np040023h.

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2

Huo, Jun, Sheng-Ping Yang, Jian Ding, and Jian-Min Yue. "Cytotoxic Sesquiterpene Lactones fromEupatoriumlindleyanum." Journal of Natural Products 68, no. 1 (2005): 156. http://dx.doi.org/10.1021/np0402118.

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3

Semakov, A. V., L. V. Anikina, and S. G. Klochkov. "Synthesis and Cytotoxic Activity of the Products of Addition of Thiophenol to Sesquiterpene Lactones." Russian Journal of Bioorganic Chemistry 47, no. 4 (2021): 906–17. http://dx.doi.org/10.1134/s106816202104018x.

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Abstract— Derivatives of sesquiterpene lactones modified at the lactone ring with a thiophenol residue have been synthesized. The resulting conjugates with thiophenol have capacity for the oxidation–elimination reaction by the action of ROS of a tumor cell with the release of initial cytotoxic lactones. It has been proposed to use the resulting sulfur-containing conjugates as ROS-activated prodrugs of sesquiterpene lactones. The antiproliferative properties of the conjugates have been examined on tumor and pseudonormal cell lines. The cytotoxicity of the conjugates is lower than that of parent

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4

Surowiak, Alicja K., Lucyna Balcerzak, Stanisław Lochyński, and Daniel J. Strub. "Biological Activity of Selected Natural and Synthetic Terpenoid Lactones." International Journal of Molecular Sciences 22, no. 9 (2021): 5036. http://dx.doi.org/10.3390/ijms22095036.

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Terpenoids with lactone moieties have been indicated to possess high bioactivity. Certain terpenoid lactones exist in nature, in plants and animals, but they can also be obtained by chemical synthesis. Terpenoids possessing lactone moieties are known for their cytotoxic, anti-inflammatory, antimicrobial, anticancer, and antimalarial activities. Moreover, one terpenoid lactone, artemisinin, is used as a drug against malaria. Because of these abilities, there is constant interest in new terpenoid lactones that are both isolated and synthesized, and their biological activities have been verified.

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5

Włoch, Aleksandra, Dominika Stygar, Fouad Bahri та ін. "Antiproliferative, Antimicrobial and Antiviral Activity of β-Aryl-δ-iodo-γ-lactones, Their Effect on Cellular Oxidative Stress Markers and Biological Membranes". Biomolecules 10, № 12 (2020): 1594. http://dx.doi.org/10.3390/biom10121594.

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The aim of this work was the examination of biological activity of three selected racemic cis-β-aryl-δ-iodo-γ-lactones. Tested iodolactones differed in the structure of the aromatic fragment of molecule, bearing isopropyl (1), methyl (2), or no substituent (3) on the para position of the benzene ring. A broad spectrum of biological activity as antimicrobial, antiviral, antitumor, cytotoxic, antioxidant, and hemolytic activity was examined. All iodolactones showed bactericidal activity against Proteus mirabilis, and lactones 1,2 were active against Bacillus cereus. The highest cytotoxic activit

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6

Park, Eun, and Jinwoong Kim. "Cytotoxic Sesquiterpene Lactones fromInula britannica." Planta Medica 64, no. 08 (1998): 752–54. http://dx.doi.org/10.1055/s-2006-957573.

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7

Yang, Yu-Liang, Sue-Ming Chang, Ching-Chung Wu, et al. "Cytotoxic Sesquiterpene Lactones fromPseudoelephantopus spicatus." Journal of Natural Products 70, no. 11 (2007): 1761–65. http://dx.doi.org/10.1021/np070331q.

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8

Yang, N. Y., S. H. Qian, J. A. Duan, P. Li, and L. J. Tian. "Cytotoxic sesquiterpene lactones fromEupatorium lindleyanum." Journal of Asian Natural Products Research 9, no. 4 (2007): 339–45. http://dx.doi.org/10.1080/10286020600727673.

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9

Choi, Sang Zin, Sang Un Choi, and Kang Ro Lee. "Cytotoxic sesquiterpene lactones fromSaussurea calcicola." Archives of Pharmacal Research 28, no. 10 (2005): 1142–46. http://dx.doi.org/10.1007/bf02972976.

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10

Faizullina, Lily Kh, Yulia A. Khalilova, Artur R. Tagirov, et al. "Evaluation of fungicidal, bactericidal and anti-tumor activities of lactones of medium and large sizes of cycles obtained from levoglucosenone." Butlerov Communications 59, no. 9 (2019): 100–105. http://dx.doi.org/10.37952/roi-jbc-01/19-59-9-100.

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Medium and large lactones attract the attention of chemists by the uniqueness of their structure, versatile biological activity and limited availability. Among the secondary metabolites of this group, β-lactones are more common, then γ- and δ-lactones, classical and non-classical macrolides, polyene antibiotics, spiro-macrolides and macrolactones. On the basis of many lactones, important preparations of the most diverse pharmacological action have been obtained. Earlier, we proposed a 3-stage scheme for the synthesis of chiral lactones of medium and large size based on levoglucosenone. The lac

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11

Torrens, Francisco, and Gloria Castellano. "Structure-Activity Relationships of Cytotoxic Lactones as Inhibitors and Mechanisms of Action." Current Drug Discovery Technologies 17, no. 2 (2020): 166–82. http://dx.doi.org/10.2174/1570163816666190101113434.

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Background: Some lactones prevent protein Myb-dependent gene expression. Objective: The object is to calculate inhibitors of Myb-brought genetic manifestation. Methods: Linear quantitative structure–potency relations result expanded, among sesquiterpene lactones of a variety of macrocycles (pseudoguaianolides, guaianolides, eudesmanolides and germacranolides), to establish which part of the molecule constitutes their pharmacophore, and predict their inhibitory potency on Myb-reliant genetic manifestation, which may result helpful as leads for antileukaemic therapies with a new mechanism of act

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12

Quintana, José, and Francisco Estévez. "Recent Advances on Cytotoxic Sesquiterpene Lactones." Current Pharmaceutical Design 24, no. 36 (2019): 4355–61. http://dx.doi.org/10.2174/1381612825666190119114323.

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Sesquiterpene lactones are naturally occurring compounds that have attracted considerable attention because to their vast array of biological activities. These plant-derived compounds contain the α-methylene-γ- butyrolactone functional group, which is the structural requirement for their pharmacological activities. Many of them exhibit cancer cell cytotoxicity and are promising anticancer agents through multiple mechanisms of action. Sesquiterpene lactones are alkylating agents that form covalent adducts in vivo and inhibit enzymes and key proteins. They are also potent apoptotic inducers in s

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13

Li, Lu, Hongchun Liu, Chunping Tang, et al. "Cytotoxic sesquiterpene lactones from Artemisia anomala." Phytochemistry Letters 20 (June 2017): 177–80. http://dx.doi.org/10.1016/j.phytol.2017.04.038.

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14

Zan, Ke, Xiao-Qing Chen, Ming-Bo Zhao, Yong Jiang, and Peng-Fei Tu. "Cytotoxic sesquiterpene lactones from Artemisia myriantha." Phytochemistry Letters 37 (June 2020): 33–36. http://dx.doi.org/10.1016/j.phytol.2020.03.009.

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15

Bloor, Stephen J., and Brian P. J. Molloy. "Cytotoxic Norditerpene Lactones from Ileostylus micranthus." Journal of Natural Products 54, no. 5 (1991): 1326–30. http://dx.doi.org/10.1021/np50077a015.

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16

Lee, JunSung, ByungSun Min, SangMyung Lee, et al. "Cytotoxic Sesquiterpene Lactones from Carpesium abrotanoides." Planta Medica 68, no. 8 (2002): 745–47. http://dx.doi.org/10.1055/s-2002-33789.

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17

Silva, Lúcia, Arlindo C. Gomes, and Jesus M. L. Rodilla. "Diterpene Lactones with Labdane, Halimane and Clerodane Frameworks." Natural Product Communications 6, no. 4 (2011): 1934578X1100600. http://dx.doi.org/10.1177/1934578x1100600410.

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The labdane, halimane and clerodane type diterpenoids are compounds that have been isolated in plants of several families. These molecules and their derivatives with a lactone group on the side chain or on the decaline system, have a great interest because of their biological properties as insect antifeedant, antiviral, cytotoxic and trypanocidal. The scope of this review is lactones diterpenoids with labdane, halimane and clerodane frameworks.

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18

Youssef, Diaa T. A., Mahmoud A. Ramadan, Sabrin R. M. Ibrahim, and Jihan M. Badr. "Cytotoxic Sesquiterpene Lactones of Egyptian Tanacetum santolinoides." Natural Product Communications 2, no. 8 (2007): 1934578X0700200. http://dx.doi.org/10.1177/1934578x0700200801.

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The chloroform soluble fraction of the methanolic extract of the aerial parts of Tanacetum santolinoides afforded six sesquiterpene lactones. Tanacetolide A (1) was isolated for the first time from a natural source, in addition to five known sesquiterpene lactones. The structures were established on the basis of extensive studies of their 1D and 2D (1H-1H COSY, HMQC, HMBC, HOHAHA and NOESY) NMR spectra and FAB mass spectral determinations. The compounds showed good cytotoxic activity when tested using the brine shrimp bioassay.

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19

MALDONADO, Eliana M. "Cytotoxic Sesquiterpene Lactones from Kauna lasiophthalma Griseb." Scientia Pharmaceutica 82, no. 1 (2014): 147–60. http://dx.doi.org/10.3797/scipharm.1310-18.

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20

Aldeco-Pérez, Eugenia, Henri Rudler, Andrée Parlier, et al. "A simple synthesis of cytotoxic endoperoxide lactones." Tetrahedron Letters 47, no. 51 (2006): 9053–56. http://dx.doi.org/10.1016/j.tetlet.2006.10.093.

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21

Kasaian, Jamal, Milad Iranshahy, Milena Masullo, Sonia Piacente, Fatemeh Ebrahimi, and Mehrdad Iranshahi. "Sesquiterpene lactones fromFerula oopodaand their cytotoxic properties." Journal of Asian Natural Products Research 16, no. 3 (2013): 248–53. http://dx.doi.org/10.1080/10286020.2013.866099.

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22

Zaghloul, Ahmed M., Hasan S. Yusufoglu, Mohamad Ayman A. Salkini, and Aftab Alam. "New cytotoxic sesquiterpene lactones from Anthemis scrobicularis." Journal of Asian Natural Products Research 16, no. 9 (2014): 922–29. http://dx.doi.org/10.1080/10286020.2014.931377.

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23

Ngassapa, Olipa D., Djaja D. Soejarto, Chun-Tao Che, John M. Pezzuto, and Norman R. Farnsworth. "New Cytotoxic Lupane Lactones from Kokoona ochracea." Journal of Natural Products 54, no. 5 (1991): 1353–59. http://dx.doi.org/10.1021/np50077a019.

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24

Sun, Chang-Ming, Wan-Jr Syu, Ming-Jaw Don, Jang-Jih Lu, and Gum-Hee Lee. "Cytotoxic Sesquiterpene Lactones from the Root ofSaussurealappa." Journal of Natural Products 66, no. 9 (2003): 1175–80. http://dx.doi.org/10.1021/np030147e.

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25

Kim, Mi Ran, Bang Yeon Hwang, Eun-Sook Jeong, et al. "cytotoxic germacranolide sesquiterpene lactones fromCarpesium triste var.manshuricum." Archives of Pharmacal Research 30, no. 5 (2007): 556–60. http://dx.doi.org/10.1007/bf02977648.

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26

Kamizela, Angelika, Barbara Gawdzik, Mariusz Urbaniak та ін. "New γ-Halo-δ-lactones and δ-Hydroxy-γ-lactones with Strong Cytotoxic Activity". Molecules 24, № 10 (2019): 1875. http://dx.doi.org/10.3390/molecules24101875.

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This paper presents the synthesis of γ -halo- δ -lactones, δ -iodo- γ -lactones and δ -hydroxy- γ -lactones from readily available organic substrates such as trans-crotonaldehyde and aryl bromides. Crystal structure analysis was carried out for lactones that were obtained in crystalline form. All halo- δ -lactones and δ -hydroxy- γ -lactones were highly cytotoxic against gastric cancer AGS cells with I C 50 values in the range of 0.0006–0.0044 mM. Some lactones showed high bactericidal activity against E. coli ATCC 8739 and S. aureus ATCC 65389, which reduced the number of CFU/mL by 70–83% and

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27

Gohari, Ahmad Reza, Mahmoud Mosaddegh, Farzaneh Naghibi, et al. "Cytotoxic sesquiterpene lactones from the aerial parts of Inula aucheriana." Anais da Academia Brasileira de Ciências 87, no. 2 (2015): 777–85. http://dx.doi.org/10.1590/0001-3765201520140063.

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Inula aucheriana DC is a member of the family Asteraceae which is known to produce cytotoxic secondary metabolites noted as sesquiterpene lactones. In the present study, sesquiterpene lactones inuchinenolide B, 6-deoxychamissonolide (stevin) and 14-acetoxy-1β,5α,7αH-4β-hydroxy-guai-9(10),11(13)-dien-12,8α-olide were isolated from I. aucheriana. Inuchinenolide B and 14-acetoxy-1β,5α,7αH-4β-hydroxy-guai-9(10),11(13)-dien-12,8α-olide were further evaluated by the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) assay to demonstrate cytotoxic activity with IC50 values of (56.6,

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28

Xiang, Ping, Xin Guo, Yang-Yang Han, Jin-Ming Gao, and Jiang-Jiang Tang. "Cytotoxic and Pro-apoptotic Activities of Sesquiterpene Lactones from Inula Britannica." Natural Product Communications 11, no. 1 (2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100103.

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In this study, five known sesquiterpene lactones (STL) with an α-methylene-γ-lactone motif, including two eudesmanolides, 1β-hydroxyalantolactone (1) and ivangustin (2), and three 1,10-seco-eudesmanolides, 1- O-acetylbritannilactone (3), 1,6- O, O-diacetylbritannilactone (4), and 6α- O(2-methylbutyryl)britannilactone (5) were isolated from the flower heads of the medicinal plant Inula britannica. Their structures were characterized by spectroscopic methods. X-ray data of 2 is reported for the first time. Among them, eudesmanolides 1 and 2 exhibited remarkable cytotoxicity against HEp2, SGC-790

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29

Babu Mereyala, Hari, and Maju Joe. "Cytotoxic Activity of Styryl Lactones and their Derivatives." Current Medicinal Chemistry-Anti-Cancer Agents 1, no. 3 (2001): 293–300. http://dx.doi.org/10.2174/1568011013354606.

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30

Thi Ngo, Quynh-Mai, Thao Quyen Cao, Mi Hee Woo, and Byung Sun Min. "Cytotoxic Lactones from the Pericarps of Litsea japonica." Natural Product Sciences 25, no. 1 (2019): 23. http://dx.doi.org/10.20307/nps.2019.25.1.23.

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31

LIAO, Shang-Gao, Zhen WANG, Jing LI, et al. "Cytotoxic sesquiterpene lactones from Vernonia bockiana." Chinese Journal of Natural Medicines 10, no. 3 (2012): 230–33. http://dx.doi.org/10.3724/sp.j.1009.2012.00230.

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32

Pereira Cabral, Márcia R., Mariana Cecchetto, João M. Batista, et al. "Cytotoxic sesquiterpene lactones from Campuloclinium macrocephalum (=Eupatorium macrocephalum)." Phytochemistry 179 (November 2020): 112469. http://dx.doi.org/10.1016/j.phytochem.2020.112469.

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33

Triana, Jorge, José Luis Eiroa, Juan José Ortega, et al. "Sesquiterpene Lactones fromGonospermum gomeraeandG. fruticosumand Their Cytotoxic Activities." Journal of Natural Products 71, no. 12 (2008): 2015–20. http://dx.doi.org/10.1021/np800474v.

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34

Chen, Xin, Zha-Jun Zhan, Xiong-Wen Zhang, Jian Ding, and Jian-Min Yue. "Sesquiterpene Lactones with Potent Cytotoxic Activities fromVernonia chinensis." Planta Medica 71, no. 10 (2005): 949–54. http://dx.doi.org/10.1055/s-2005-871212.

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35

Chen, Xin, Zha-Jun Zhan, Xiong-Wen Zhang, Jian Ding, and Jian-Min Yue. "Sesquiterpene Lactones with Potent Cytotoxic Activities fromVernonia chinensis." Planta Medica 71, no. 12 (2005): 1178. http://dx.doi.org/10.1055/s-2005-916265.

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36

Ren, Yulin, Daniel D. Lantvit, Youcai Deng, et al. "Potent Cytotoxic Arylnaphthalene Lignan Lactones from Phyllanthus poilanei." Journal of Natural Products 77, no. 6 (2014): 1494–504. http://dx.doi.org/10.1021/np5002785.

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37

Williams, Russell B., Andrew Norris, Carla Slebodnick, et al. "Cytotoxic Sesquiterpene Lactones fromVernonia pachycladafrom the Madagascar Rainforest1." Journal of Natural Products 68, no. 9 (2005): 1371–74. http://dx.doi.org/10.1021/np050202e.

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38

Saroglou, Vasiliki, Anastasia Karioti, Costas Demetzos, Kostas Dimas, and Helen Skaltsa. "Sesquiterpene Lactones fromCentaureaspinosaand Their Antibacterial and Cytotoxic Activities." Journal of Natural Products 68, no. 9 (2005): 1404–7. http://dx.doi.org/10.1021/np058042u.

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39

Tabopda, Turibio Kuiate, Joseph Ngoupayo, Jiawei Liu, et al. "Further Cytotoxic Sesquiterpene Lactones from Elephantopus mollis KUNTH." CHEMICAL & PHARMACEUTICAL BULLETIN 56, no. 2 (2008): 231–33. http://dx.doi.org/10.1248/cpb.56.231.

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40

Xu, Fengqing, Xiaoxiao Chen, Jiangmiao Hu, et al. "Cytotoxic Picrotoxane-type Sesquiterpenoid Lactones from Dendrobium huoshanense." Records of Natural Products, no. 2 (August 25, 2021): 144–49. http://dx.doi.org/10.25135/rnp.260.21.04.2048.

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41

Mandal, Sudip Kumar, Utsab Debnath, Amresh Kumar, et al. "Natural Sesquiterpene Lactones in the Prevention and Treatment of Inflammatory Disorders and cancer: A Systematic Study of this Emerging Therapeutic Approach based on Chemical and Pharmacological Aspect." Letters in Drug Design & Discovery 17, no. 9 (2020): 1102–16. http://dx.doi.org/10.2174/1570180817999200421144007.

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Background and Introduction: Sesquiterpene lactones are a class of secondary metabolite that contains sesquiterpenoids and lactone ring as pharmacophore moiety. A large group of bioactive secondary metabolites such as phytopharmaceuticals belong to this category. From the Asteraceae family-based medicinal plants, more than 5,000 sesquiterpene lactones have been reported so far. Sesquiterpene lactone-based pharmacophore moieties hold promise for broad-spectrum biological activities against cancer, inflammation, parasitic, bacterial, fungal, viral infection and other functional disorders. Moreov

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42

Kolli, El Hadj, Francisco León, Fadila Benayache, et al. "Cytotoxic sesquiterpene lactones and other constituents of Centaurea omphalotricha." Journal of the Brazilian Chemical Society 23, no. 5 (2012): 977–83. http://dx.doi.org/10.1590/s0103-50532012000500026.

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43

Bruno, Maurizio, Sergio Rosselli, Antonella Maggio, et al. "Cytotoxic Activity of Some Natural and Synthetic Sesquiterpene Lactones." Planta Medica 71, no. 12 (2005): 1176–78. http://dx.doi.org/10.1055/s-2005-873139.

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44

Muhammad, Ilias, Satoshi Takamatsu, Jaber S. Mossa, Farouk S. El-Feraly, Larry A. Walker, and Alice M. Clark. "Cytotoxic sesquiterpene lactones from Centaurothamnus maximus and Vicoa pentanema." Phytotherapy Research 17, no. 2 (2003): 168–73. http://dx.doi.org/10.1002/ptr.1258.

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45

Shen, Ya-Ching, Kuang-Liang Lo, Yao Haur Kuo, and Ashraf Taha Khalil. "Cytotoxic Sesquiterpene Lactones fromEupatoriumkiirunense,a Coastal Plant of Taiwan." Journal of Natural Products 68, no. 5 (2005): 745–50. http://dx.doi.org/10.1021/np040214k.

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46

Wang, Lun, Jing Wang, Fu Li, et al. "Cytotoxic Sesquiterpene Lactones from Aerial Parts of Xanthium sibiricum." Planta Medica 79, no. 08 (2013): 661–65. http://dx.doi.org/10.1055/s-0032-1328482.

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47

Medjroubi, Kamel, Fadila Benayache, and Jaime Bermejo. "Sesquiterpene lactones from Centaurea musimomum. Antiplasmodial and cytotoxic activities." Fitoterapia 76, no. 7-8 (2005): 744–46. http://dx.doi.org/10.1016/j.fitote.2005.08.005.

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48

Adekenov, S. M., and G. A. Atazhanova. "Heteroatom-Containing Natural Sesquiterpene Lactones and Methods for their Obtaining." Eurasian Chemico-Technological Journal 15, no. 3 (2013): 195. http://dx.doi.org/10.18321/ectj223.

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This review shows the data about isolated heteroatom-containing sesquiterpene lactones from various genera of <em>Asteraceae</em> family, natural occurence, isolation methods and their biological activity. Chlorinecontaining sesquiterpene lactones were isolated from genera of<em> Artemisia</em> L., <em>Achillea</em> L., <em>Acroptilon Cass</em>, <em>Centaurea</em> L., <em>Chartolepis Cass</em>, <em>Eupatorium</em> L., <em>Jurinea Cass</em>, <em>Rhaponticum Adams</em>, <em>Saussurea

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49

Bach, Sandra M., Mario A. Fortuna, Rodgoun Attarian, et al. "Antibacterial and Cytotoxic Activities of the Sesquiterpene Lactones Cnicin and Onopordopicrin." Natural Product Communications 6, no. 2 (2011): 1934578X1100600. http://dx.doi.org/10.1177/1934578x1100600202.

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The antimicrobial and cytotoxic activities of chloroform extracts from the weeds Centaurea tweediei and C. diffusa, and the main sesquiterpene lactones isolated from these species, onopordopicrin and cnicin, respectively, were assayed. Results show that the chloroform extracts from both Centaurea species possess antibacterial activities against a panel of Gram-positive and Gram-negative bacteria. Remarkable antibacterial activity against methicillin-resistant Staphylococcus aureus was also measured. Both the extracts and the purified sesquiterpene lactones show high cytotoxicity against human-

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50

Wiart, Christophe. "GoniothalamusSpecies: A Source of Drugs for the Treatment of Cancers and Bacterial Infections?" Evidence-Based Complementary and Alternative Medicine 4, no. 3 (2007): 299–311. http://dx.doi.org/10.1093/ecam/nem009.

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Irrespective of the presence of cytotoxic acetogenins and styryl-lactones in the genusGoniothalamus, only 22 species in the genusGoniothalamus, out of 160 species (13.7%) have so far been investigated. In an effort to promote further research on the genusGoniothalamuswhich could represent a source of drugs for the treatment of cancers and bacterial infections, this work offers a broad analysis of current knowledge onGoniothalamusspecies. Therefore, it includes (i) taxonomy (ii) botanical description (iii) traditional medicinal uses and (iv) phytochemical and pharmacological studies. We discuss

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