Review
Chemistry, Medicinal
Nur Zahirah Abd Rani, Yean Kee Lee, Sarfraz Ahmad, Ramu Meesala, Iskandar Abdullah
Summary: Marine natural products containing tricyclic guanidine alkaloids possess diverse and unique structures, contributing to a wide range of bioactivities. However, their synthetic approaches and stereochemical assignments are still limited. Batzelladine and ptilocaulin are of high interest and exhibit different compound types. This review discusses the synthetic approaches to tricyclic guanidine alkaloids, focusing on the batzelladine and ptilocaulin skeletons, and compiles the latest research on their synthesis and bioactivities from the 1980s to 2022.
Article
Chemistry, Medicinal
Liu Zheng, Peng-Ju Guo, Yao Zhu, Chen-Yue Li, Wen-Qiong Wang, Li-Jiang Xuan
Summary: Five undescribed guanidine alkaloids, plumbagines H-K (1-4) and plumbagoside E (5), as well as five known analogues (6-10) were isolated from the roots of Plumbago zeylanica. Their structures were determined through spectroscopic analysis and chemical methods. Furthermore, their anti-inflammatory activities were evaluated by measuring nitric oxide (NO) concentrations in LPS-induced RAW 264.7 cells. However, compounds 1 and 3-5 showed no inhibition of NO secretion but instead significantly increased its secretion. This suggests that compounds 1-10 may have potential as novel immune potentiators.
Article
Plant Sciences
Emmanuel O. Adeyoju, Clement O. Ajayi, Awodayo O. Adepiti, Anthony A. Elujoba
Summary: This study compared the antimalarial activity of methanol and water extracts of MAMA Powder against Plasmodium berghei-infected mice, finding that the water extract exhibited higher efficacy and can be optimized for chloroquine-resistant malaria, aiding in the production of various dosage forms.
JOURNAL OF ETHNOPHARMACOLOGY
(2022)
Review
Biochemistry & Molecular Biology
Yang Hai, Zi-Mu Cai, Peng-Jie Li, Mei-Yan Wei, Chang-Yun Wang, Yu-Cheng Gu, Chang-Lun Shao
Summary: This review provides an overview of the advancements and potential of antimalarial marine lead compounds from 1972 to 2021. By analyzing the structure-activity relationships, molecular mechanisms of targets, and drug-like properties of selected candidate molecules, this study offers insights for future drug development. Moreover, it highlights the potential of natural products as an effective strategy in antimalarial drug research and development.
NATURAL PRODUCT REPORTS
(2022)
Article
Chemistry, Multidisciplinary
Cui Guo, Pei Wang, Xiaoyan Pang, Xiuping Lin, Shengrong Liao, Bin Yang, Xuefeng Zhou, Junfeng Wang, Yonghong Liu
Summary: Study involved isolation and characterization of structurally novel marine natural products. A compound displayed significant antibacterial and cytotoxic activities, indicating potential as a promising drug lead. This finding could attract attention from both chemists and pharmacists in the field.
Review
Biochemistry & Molecular Biology
Shiyang Zhou, Gangliang Huang
Summary: Marine alkaloids exhibit activity in antifungal and antimalarial properties. The discussion covers the optimization process, chemical synthesis, antimalarial activity, and antibacterial activity of various compounds.
CHEMICAL BIOLOGY & DRUG DESIGN
(2021)
Article
Chemistry, Medicinal
Qi Wang, Chunhua Gao, Zhun Wei, Xiaowen Tang, Lixia Ji, Xiangchao Luo, Xiaoping Peng, Gang Li, Hongxiang Lou
Summary: Twelve new and four known alkaloids were isolated from the sponge Stylissa massa collected in the South China Sea, and their structures and activities were studied.
Article
Chemistry, Analytical
Jiranan Chaingam, Thaweesak Juengwatanatrakul, Gorawit Yusakul, Tripetch Kanchanapoom, Waraporn Putalun
Summary: This study developed and validated HPLC methods to analyze bioactive compounds in Eurycoma longifolia (EL) and E. harmandiana (EH). EH exhibited anti-inflammatory activity comparable to EL, with a higher concentration of chaparrinone observed in EH.
JOURNAL OF AOAC INTERNATIONAL
(2021)
Article
Chemistry, Physical
Valentin A. Semenov, Leonid B. Krivdin
Summary: The PBE0 functional combined with a new triple zeta basis set 3z-S was used for benchmark calculations of C-13 NMR chemical shifts in a variety of natural products, showing good accuracy and high cost-effectiveness compared to larger basis sets. This suggests a prospective use of the 3z-S basis set for C-13 NMR calculations in a wide range of natural products.
INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY
(2021)
Article
Chemistry, Physical
Savina Savir, Jonathan Wee Kent Liew, Indra Vythilingam, Yvonne Ai Lian Lim, Chun Hoe Tan, Kae Shin Sim, Vannajan Sanghiran Lee, Mohd Jamil Maah, Kong Wai Tan
Summary: The synthesized Schiff base metal complexes exhibited cytotoxicity against human colorectal carcinoma HCT 116 and antiplasmodial activity. The biological activities were influenced by factors such as the hydrophobicity of the substituent groups and the interaction with DNA base pairs.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Physical
Thong Le Minh Pham, Thanh Khoa Phung, Ho Viet Thang
Summary: Understanding the interaction between five-membered aromatic heterocycles and Fe(1 1 0) surface is crucial for designing novel inhibitors against iron and steel corrosion. In this study, the adsorption properties and bonding mechanisms of pyrrole, furan, and thiophene on Fe(1 1 0) surface were investigated using density functional theory (DFT) calculations. The results showed that the adsorbates lie flat at the hollow site and form covalent bonds with surface Fe atoms. Large adsorption energies and charge transfers from Fe(1 1 0) to the adsorbates indicate chemisorptions.
APPLIED SURFACE SCIENCE
(2022)
Article
Chemistry, Multidisciplinary
Souad Senhaji, Fatima Lamchouri, Taoufik Akabli, Hamid Toufik
Summary: Experimental and computational studies were conducted to investigate the antioxidant activities of several compounds. The results showed that harmine has higher hydrogen peroxide scavenging activity compared to ascorbic acid. Harmalol exhibited the highest antioxidant activity in various tests. Computational analysis revealed that harmalol and harmaline are the most reactive molecules and can interact with the myeloperoxidase receptor.
STRUCTURAL CHEMISTRY
(2022)
Review
Chemistry, Organic
Manoj Kumar, Shalini Verma, Mukul Sharma, Brijesh Poonam, Brijesh Rathi
Summary: This article reviews the metal-catalysed synthesis and applications of benzo-fused five-membered N/O/S heterocyclic compounds, such as indole, benzofuran, and benzothiophene. It discusses the progress made in the past five years and explores unexplored opportunities for future research.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Medicine, Research & Experimental
Mohammed Albashir Abazar Elmamoon Ball Elsheep, Udaya Ratna Kolli, Yousif Osman Salih Saeed, Jithendra Chimakurthy, Ravindra Babu Pingili
Summary: Plant alkaloids are a diverse class of chemical compounds that have been used for medicinal purposes for thousands of years. They can form salts and are generally soluble in water and dilute alcohols. Alkaloids are classified based on their natural origins or chemical composition. This article focuses on the potential of alkaloids for the treatment of neurodegenerative diseases and highlights their various pharmacological activities.
INTERNATIONAL JOURNAL OF AYURVEDIC MEDICINE
(2022)
Proceedings Paper
Materials Science, Multidisciplinary
Jasmine Gupta
Summary: Marine organisms containing guanidine alkaloids with promising biological activities are explored by chemists and biologists, characterized by NMR and mass spectroscopy. This review focuses on comparing the cytotoxic and antimalarial activities of different guanidine alkaloids isolated from Monanchora sp.
MATERIALS TODAY-PROCEEDINGS
(2021)
Article
Plant Sciences
Raymond Muganga, Joanne Bero, Joelle Quetin-Leclercq, Luc Angenot, Monique Tits, Ange Mouithys-Mickalad, Thierry Franck, Michel Frederich
Summary: This study aimed to determine the in vitro antitrypanosomal, antileishmanial, antioxidant, and anti-inflammatory activities of Terminalia mollis root crude extracts. The results showed that the extracts exhibited good growth inhibition on Trypanosoma brucei brucei, but were inactive against Leishmania mexicana mexicana. Additionally, the extracts showed interesting antioxidant and anti-inflammatory activities.
Article
Plant Sciences
Lucy Catteau, Laura Schioppa, Claire Beaufay, Cynthia Girardi, Marie-France Herent, Michel Frederich, Joelle Quetin-Leclercq
Summary: The composition of antiparasitic compounds from the leaves of Vitellaria paradoxa was investigated, with 11 isolated compounds showing varying levels of activity against Plasmodium falciparum, Trypanosoma brucei brucei, and Leishmania mexicana mexicana. A triterpenic ester mixture showed promising antitrypanosomal activity with low cytotoxicity, warranting further studies on its bioavailability and mode of action.
Review
Biochemistry & Molecular Biology
Gilles Degotte, Bernard Pirotte, Pierre Francotte, Michel Frederich
Summary: Malaria, caused mainly by Plasmodium falciparum, remains a major concern in developing regions, with an increase in cases for the third consecutive year. The appearance of resistance to antimalarials, including artemisinin, calls for the urgent need to design new anti-Plasmodium compounds. Studies on natural sources have identified 648 molecules, mostly from plants, with inhibitory effects on Plasmodium falciparum, suggesting these compounds could serve as potential leads for the development of new malaria treatments.
CURRENT MEDICINAL CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Jean Claude Didelot Tomani, Olivier Bonnet, Alain Nyirimigabo, William Deschamps, Alembert Tiabou Tchinda, Olivia Jansen, Allison Ledoux, Marie Jeanne Mukazayire, Luc Vanhamme, Michel Frederich, Raymond Muganga, Jacob Souopgui
Summary: The study tested the in vitro antiplasmodial activity of the crude extract and compounds from Eriosema montanum Baker f. roots against Plasmodium falciparum 3D7 strain, showing significant antiplasmodial activity with selectivity. The bioactivity-guided isolation of major compounds revealed the potential of eucomic acid as a promising candidate for malaria treatment.
Article
Chemistry, Medicinal
Gilles Degotte, Bernard Pirotte, Michel Frederich, Pierre Francotte
Summary: Malaria remains one of the deadliest infectious diseases of 2021, with an increasing number of infections attributed to drug resistance, highlighting the urgent need for new alternatives. Research has shown that derivatives of polyhydroxybenzoic acids, particularly gallic acid derivatives, have demonstrated potential for further development in antiplasmodial effects. This study identified methyl 4-benzoxy-3,5-dihydroxybenzoate as a potential lead compound for future antimalarial drug research due to its marked inhibitory activity against Plasmodium falciparum and significant water solubility.
ARCHIV DER PHARMAZIE
(2021)
Article
Plant Sciences
Allison Ledoux, Daphnee Beriot, Lucia Mamede, Pauline Desdemoustier, Fanny Detroz, Olivia Jansen, Michel Frederich, Erik Maquoi
Summary: Poupartone B, a compound derived from the endemic plant Poupartia borbonica in the Mascarene Islands, was found to exhibit potent inhibitory effects on human cancer cells and induce cell death, but also demonstrated high toxicity on human cells. It induced an array of cellular alterations leading to cell death, highlighting its potential pharmacological interest.
Article
Chemistry, Medicinal
Gilles Degotte, Bernard Pirotte, Michel Frederich, Pierre Francotte
Summary: Malaria, caused by Plasmodium falciparum, is one of the deadliest infectious diseases globally, especially in Africa. Despite the availability of effective drugs, the number of cases has been increasing since 2015, possibly due to parasite and mosquito resistance. Therefore, there is a need to search for new alternative treatments. Polyphenols, specifically small phenolic acids, could serve as a promising starting point for developing new antimalarials.
LETTERS IN DRUG DESIGN & DISCOVERY
(2022)
Article
Plant Sciences
Ramona Paltinean, Irina Ielciu, Daniela Hanganu, Mihaela Niculae, Emoke Pall, Luc Angenot, Monique Tits, Andrei Mocan, Mihai Babota, Oleg Frumuzachi, Mircea Tamas, Gianina Crisan, Michel Frederich
Summary: This study evaluated the alkaloid content of F. schleicheri and assessed its antioxidant, anti-cholinesterase, and cytotoxic potential. The results showed that F. schleicheri has significant medicinal potential and selective cytotoxicity towards tumor cells.
Article
Biochemistry & Molecular Biology
Loic Martinet, Aymeric Naome, Lucas C. D. Rezende, Deborah Tellatin, Bernard Pignon, Jean-Denis Docquier, Filomena Sannio, Dominique Baiwir, Gabriel Mazzucchelli, Michel Frederich, Sebastien Rigali
Summary: Streptomyces lunaelactis strains isolated from moonmilk deposits exhibit significant heterogeneity in the content of biosynthetic gene clusters (BGCs) for specialized metabolite production. Specifically, the cryptic BGC 28a is carried only by a subgroup of S. lunaelactis strains and is predicted to produce nonribosomal peptide antibiotics containing piperazic acid (Piz). Through metabolomics and peptidogenomics analysis, the cyclic hexapeptide lunaemycin A, with a unique amino acid sequence, was identified as the main compound synthesized by BGC 28a. Lunaemycins demonstrated potent bactericidal activity against Gram-positive bacteria, including multi-drug resistant clinical isolates. This study highlights the importance of accurate in silico analysis in elucidating the structure and bioactivity of cryptic BGCs.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Biochemistry & Molecular Biology
Allison Ledoux, Carla Hamann, Olivier Bonnet, Kateline Jullien, Joelle Quetin-Leclercq, Alembert Tchinda, Jacqueline Smadja, Anne Gauvin-Bialecki, Erik Maquoi, Michel Frederich
Summary: Casearia coriacea Vent., a plant endemic to the Mascarene Islands, exhibited potent antiplasmodial activity through the presence of three identified compounds, caseamembrin T (1), corybulosin I (2), and isocaseamembrin E (3), with IC50 values ranging from 0.25 to 0.51 μg/mL. While these compounds also showed antileishmanial and antitrypanosomal properties, they exhibited selectivity towards the malaria parasite with selectivity indices ranging from 6 to 12 and 25 to 100, respectively. Additionally, compounds 1-3 demonstrated promising activity against pancreatic carcinoma cells (IC50 < 1 μg/mL). However, the main compound, caseamembrin T (1), displayed significant toxicity when evaluated on zebrafish embryos.
Article
Biochemistry & Molecular Biology
Jiri Kos, Gilles Degotte, Dominika Pindjakova, Tomas Strharsky, Timotej Jankech, Tomas Gonec, Pierre Francotte, Michel Frederich, Josef Jampilek
Summary: A series of thirty-seven ring-substituted N-arylcinnamanilides prepared by microwave-assisted synthesis were shown to exhibit strong antimalarial activity in primary screening. Some of these compounds demonstrated activity comparable to the standard drug chloroquine and showed no cytotoxic effects, making them promising candidates for further investigation.
Article
Biochemistry & Molecular Biology
Andrzej Bak, Jiri Kos, Gilles Degotte, Aleksandra Swietlicka, Tomas Strharsky, Dominika Pindjakova, Tomas Gonec, Adam Smolinski, Pierre Francotte, Michel Frederich, Violetta Kozik, Josef Jampilek
Summary: A series of 4-chlorocinnamanilides and 3,4-dichlorocinnamanilides were investigated for their antiplasmodial activity, and 23 compounds showed IC50 < 30 μM. The 3,4-dichlorocinnamanilides exhibited a broader range of activity compared to the 4-chlorocinnamanilides. The most effective agent was (2E)-N-[3,5-bis(trifluoromethyl)phenyl]-3-(3,4-dichlorophenyl)prop-2-en-amide with IC50 = 1.6 μM.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Biochemistry & Molecular Biology
Gilles Degotte, Michel Frederich, Pierre Francotte, Thierry Franck, Thomas Colson, Didier Serteyn, Ange Mouithys-Mickalad
Summary: Malaria, caused by a Plasmodium genus parasite, is a widespread infectious disease that poses a serious public health problem, especially in underdeveloped countries due to increased resistance to antimalarial drugs. The study aims to explore new therapeutic approaches, including the redox process in the parasite's development. Ellagic acid and its analogues, known for their antioxidant and parasite-inhibiting properties, show potential as drug candidates. However, their low oral bioavailability has led to the development of new polyphenolic compounds. The research investigates their modulatory effect on the redox activity of neutrophils and myeloperoxidase involved in malaria.
Article
Microbiology
Alexandre Le Loarer, Remy Marcellin-Gros, Laurent Dufosse, Jerome Bignon, Michel Frederich, Allison Ledoux, Emerson Ferreira Queiroz, Jean-Luc Wolfender, Anne Gauvin-Bialecki, Mireille Fouillaud
Summary: Despite advances in medicine and technology, deadly diseases are still a threat to humanity. To find effective treatments, research is focusing on unexplored habitats with unique biodiversity, such as the marine environment. Studies have shown the potential of bioactive compounds from marine organisms in treating diseases.
Article
Biochemistry & Molecular Biology
Elise Gerometta, Gaetan Herbette, Elnur Garayev, Arnaud Marvilliers, Jean-Valere Naubron, Carole Di Giorgio, Pierre-Eric Campos, Patricia Clerc, Allison Ledoux, Michel Frederich, Beatrice Baghdikian, Isabelle Grondin, Anne Gauvin-Bialecki
Summary: A new chromanone compound (1) was isolated from the leaf extract of Calophyllum tacamahaca Willd, a medicinal plant, together with 13 known metabolites belonging to different families. The structure of compound (1) was characterized using various spectroscopic techniques. Compound (1) showed moderate cytotoxicity against HepG2 and HT29 cell lines, while compounds 7, 8, and 10-13 exhibited potent cytotoxic activity. A feature-based molecular networking approach led to the discovery of many xanthones, including analogues of the cytotoxic xanthone pyranojacareubin (10), in the leaf extract.
