Review
Chemistry, Medicinal
Yuqian Zhu, Jinran Zhao, Longbiao Luo, Yang Gao, He Bao, Pengfei Li, Hailong Zhang
Summary: Indole alkaloids play an important role in natural products due to their versatile biological activities, which are a potential source for novel antidiabetic drugs. The synthesized indole derivatives possess properties similar to natural indole alkaloids. In recent years, more and more indole derivatives have been designed and synthesized for exploring their bioactivities.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Kun Fan, Cai-Feng Ding, Shi-Yu Deng, Wen Gao, Bang-Yin Tan, Hao Wu, Ying Guo, Jing-Feng Song, Lan-Chun Zhang, Rong-Ping Zhang, Hao-Fei Yu
Summary: In this study, several alkaloids were isolated from the stem bark of Tabernaemontana corymbosa. These alkaloids showed antimicrobial activity against Staphylococcus aureus and Bacillus subtilis.
Article
Chemistry, Organic
Xiao-Yong Duan, Zhaohui Tian, Binghao Liu, Tao He, Liang-Liang Zhao, Mengdie Dong, Pengna Zhang, Jing Qi
Summary: This work describes the NHC-catalyzed Michael/Mannich/lactamization cascade reaction of enals with either indole-2-carboxaldehyde-derived aldimines or indole-7-carboxaldehyde-derived aldimines, allowing for the rapid assembly of optically active pyrroloindolones and pyrroloquinolinones derivatives under mild conditions with high yields, excellent enantioselectivities, and a broad substrate scope.
Article
Chemistry, Organic
Wei Li, Jie Qiu, Hengyuan Li, Wanli Chen, Cheng Hou, Huaifeng Li
Summary: By utilizing the radical reactivity of neutral diazoacetates, we have developed a method for synthesizing indole compounds, especially valuable [a]-annulated indoles, without the need for transition metals, oxidants, or substrate prefunctionalization. This visible-light-driven transformation is enabled by a single organophotocatalyst, without the use of metals or additives.
Article
Chemistry, Organic
Hao-Feng Zhou, Wen-Yan Li, Li-Yan Peng, Xiao-Nian Li, Zhi-Li Zuo, Qin-Shi Zhao
Summary: Five new indole alkaloids, Rhynchines A-E, with a unique skeleton structure were isolated from Uncaria rhynchophylla. Among them, compounds 1 and 2 showed strong inhibitory activities against the Ca-v 3.1 calcium channel.
Article
Chemistry, Organic
Tape Kouame, Guillaume Bernadat, Victor Turpin, Marc Litaudon, Aboua Timothee Okpekon, Jean-Francois Gallard, Karine Leblanc, Somia Rharrabti, Pierre Champy, Erwan Poupon, Mehdi A. Beniddir, Pierre Le Pogam
Summary: Melonine is a basic monoterpene indole alkaloid (MIA) skeleton from Melodinus philliraeoides, with its structure revised into an unprecedented MIA scaffold. Proposed DFT-validated biosynthetic paths to both this new core and the originally reported form suggest the thermodynamic feasibility of the original structure of melonine, indicating its potential existence as a natural product.
Article
Chemistry, Organic
Eunjoon Park, Cheolwoo Bae, Cheon-Gyu Cho, Cheol-Hong Cheon
Summary: The total syntheses of the antirhine alkaloids were achieved through a series of reactions, including the cyanide-catalyzed imino-Stetter reaction and subsequent C-ring formation to generate the key intermediate. The trans-selective installation of the homoallylic alcohol side-chain at C-15 allowed the successful total syntheses of antirhine and its known epimer.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Francisco Leon, Samuel Obeng, Marco Mottinelli, Yiming Chen, Tamara King, Erin C. Berthold, Shyam H. Kamble, Luis F. Restrepo, Avi Patel, Lea R. Gamez-Jimenez, Carolina Lopera-Londono, Takato Hiranita, Abhisheak Sharma, Aidan J. Hampson, Clinton E. Canal, Lance R. McMahon, Christopher R. McCurdy
Summary: Research showed that kratom alkaloids have effects on serotonin receptors in vitro and in vivo, with paynantheine and speciogynine exhibiting high affinity for 5-HT(1A)Rs and 5-HT(2B)Rs. These alkaloids can produce antinociceptive properties through a mechanism independent of opioid receptors.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Yubo Duan, Shu-Ning Lu, Zuguang Yang, Zhengkai Chen, Xiao-Feng Wu
Summary: An efficient and straightforward strategy for the divergent synthesis of trifluoromethyl-substituted (dihydro)pyrimidoindolones via Rh(iii)-catalyzed C-H activation/annulation of N-carbamoylindoles with CF3-imidoyl sulfoxonium ylides has been achieved. The cascade reaction proceeds through a C-H imidoylmethylation, tautomerization and intramolecular nucleophilic addition sequence, leading to the construction of a wide range of functionalized pyrimidoindolone derivatives in good to excellent yields under redox-neutral conditions.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Jiahang Yan, Yanxia Zhen, Pengyan Wang, Yimeng Han, Huanhuan Zou, Junhan Chen, Weigang He, Weiqing Xie
Summary: In this study, a de novo synthesis of the bisindole alkaloid geissolosimine was accomplished, along with the synthesis of related compounds and the demonstration of an innovative strategy. These findings provide new insights for further research.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Matteo Faltracco, Said Ortega-Rosales, Elwin Janssen, Razvan C. Cioc, Christophe M. L. Vande Velde, Eelco Ruijter
Summary: The unexpected discovery in a seemingly trivial reaction led to the selective formation of a new carbazole product. This reaction, by carefully varying substituents, revealed a complex cascade mechanism with at least 10 elementary steps that could be directed towards different carbazole derivatives.
Article
Biochemistry & Molecular Biology
Qian Zhao, Wen-Tao Zhu, Xiao Ding, Zong-Qing Huo, Paul O. Donkor, Tiwalade A. Adelakun, Xiao-Jiang Hao, Yu Zhang
Summary: Fourteen undescribed monoterpenoid indole alkaloids, voacafrines A-N, along with 7 known monoterpenoid indole alkaloids were isolated from the seeds of Voacanga africana Stapf. The structures and activities of these compounds varied, with some exhibiting acetylcholinesterase inhibitory activity and cytotoxicity against human cancer cell lines.
Article
Multidisciplinary Sciences
Jian-Ping Tan, Kehan Li, Boming Shen, Cheng Zhuang, Zanjiao Liu, Kai Xiao, Peiyuan Yu, Bing Yi, Xiaoyu Ren, Tianli Wang
Summary: This study presents a general method for constructing optically pure pseudo-natural products (PNPs) bearing N-bridged [3.3.1] ring systems through bifunctional phosphonium salt/Lewis acid relay catalysis. The method shows wide compatibility with various substrates and exhibits excellent reactivities and stereoselectivities. The obtained enantioenriched products demonstrate potential anticancer activities. This research opens up new opportunities for the catalytic synthesis of challenging chiral pseudo-natural products and offers prospects for bioactive small-molecule discovery.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Chao Liu, Luc Van Meervelt, Vsevolod A. Peshkov, Erik V. Van der Eycken
Summary: A novel gold-catalyzed hydroarylation/Michael addition process has been developed for the efficient construction of benzazepinoindole polycyclic scaffolds from readily accessible multifunctional Ugi adducts. The developed methodology exhibits a broad substrate scope, excellent functional-group tolerance, and high yields of the target benzazepinoindoles.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Biochemistry & Molecular Biology
Robert M. Hohlman, David H. Sherman
Summary: This article provides an overview of a class of indole alkaloid natural products isolated from cyanobacteria, highlighting their biological activities, general synthetic routes, and surprising biosynthetic processes leading to structurally diverse metabolites from 1984 to the end of 2020.
NATURAL PRODUCT REPORTS
(2021)
Article
Ecology
Esteban Avigliano, Maria Eugenia Rolon, Juan Jose Rosso, Ezequiel Mabragana, Alejandra Vanina Volpedo
ENVIRONMENTAL BIOLOGY OF FISHES
(2018)
Article
Multidisciplinary Sciences
Yamila P. Cardoso, Juan J. Rosso, Ezequiel Mabragana, Mariano Gonzalez-Castro, Matias Delpiani, Esteban Avigliano, Sergio Bogan, Raphael Covain, Nahuel F. Schenone, Juan M. Diaz de Astarloa
Editorial Material
Environmental Sciences
Esteban Avigliano
Article
Environmental Sciences
Esteban Avigliano, Barbara Maichak de Carvalho, Rodrigo Invernizzi, Marcelo Olmedo, Raquel Jasan, Alejandra V. Volpedo
ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH
(2019)
Article
Marine & Freshwater Biology
Esteban Avigliano, Jorge Pisonero, Nerea Bordel, Alejandro Domanico, Alejandra Vanina Volpedo
JOURNAL OF THE MARINE BIOLOGICAL ASSOCIATION OF THE UNITED KINGDOM
(2019)
Article
Environmental Sciences
Paola M. Ondarza, Samuel P. Haddad, Esteban Avigliano, Karina S. B. Miglioranza, Bryan W. Brooks
SCIENCE OF THE TOTAL ENVIRONMENT
(2019)
Article
Ecology
Esteban Avigliano, Barbara Maichak de Carvalho, Nathan Miller, Sofia Cordoba Gironde, Andrea Tombari, Karin Limburg, Alejandra V. Volpedo
MARINE ECOLOGY PROGRESS SERIES
(2019)
Article
Chemistry, Analytical
E. Avigliano, C. Clavijo, P. Scarabotti, S. Sanchez, S. Llamazares Vegh, F. R. del Rosso, J. D. Caffetti, J. F. Facetti, A. Domanico, A. V. Volpedo
MICROCHEMICAL JOURNAL
(2019)
Article
Marine & Freshwater Biology
Fernanda G. Biole, Gustavo A. Thompson, Claudia V. Vargas, Mathieu Leisen, Fernando Barra, Alejandra V. Volpedo, Esteban Avigliano
ESTUARINE COASTAL AND SHELF SCIENCE
(2019)
Article
Environmental Sciences
Esteban Avigliano, Magdalena V. Monferran, Sebastian Sanchez, Daniel A. Wunderlin, Joaquin Gastaminza, Alejandra V. Volpedo
Review
Chemistry, Multidisciplinary
Angelica Escobar, Miriam Perez, Gustavo Romanelli, Guillermo Blustein
ARABIAN JOURNAL OF CHEMISTRY
(2020)
Article
Chemistry, Medicinal
Miriam Perez, Lucia R. Fernandez, E. Elisabet Zambrano, Monica Garcia, Maria L. Uriburu, Marianela Sanchez, Guillermo Blustein, Jorge A. Palermo
Summary: The study confirms the effectiveness of Verbena and Tillandsia extracts in fouling prevention, achieving success in both laboratory and field experiments. The high growth rates of these plants offer a potential solution to sustainability issues with natural antifoulants and present a new possibility for weed management through the technological use of untapped biological resources.
REVISTA BRASILEIRA DE FARMACOGNOSIA-BRAZILIAN JOURNAL OF PHARMACOGNOSY
(2021)
Article
Multidisciplinary Sciences
Esteban Avigliano, Juan Jose Rosso, Dario Lijtmaer, Paola Ondarza, Luis Piacentini, Matias Izquierdo, Adriana Cirigliano, Gonzalo Romano, Ezequiel Nunez Bustos, Andres Porta, Ezequiel Mabragana, Emanuel Grassi, Jorge Palermo, Belen Bukowski, Pablo Tubaro, Nahuel Schenone