Natural Products and Their Derivatives with Antibacterial, Antioxidant and Anticancer Activities

A special issue of Antibiotics (ISSN 2079-6382).

Deadline for manuscript submissions: closed (1 July 2020) | Viewed by 83817

Special Issue Editor


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Guest Editor
BioZone, Department of Chemical Engineering and Applied Chemistry, University of Toronto, Toronto, ON, Canada
Interests: bioproducts from lignin and hemicelluloses; phytochemicals; bioprocess; fibers from macroalgae

Special Issue Information

Dear Colleagues,

Natural products and their derivatives have been playing an important role in health as well as in economy. These compounds are significantly contributing to discovery of new drugs and therapeutic agents. To facilitate studies on their health benefits, it is crucial to obtain these compounds at their highest purity, to be able to characterize, and then to scale up them for commercial production. This Special Issue will, therefore, highlight recent advances in production of natural products and their derivatives with antibacterial, antioxidant and anticancer properties. In particular, the issue aims to provide the audience with original research articles and reviews on:

(1) Strategies to extract and identify medical compounds from forest and marine sources

(2) Enzymatic, cultural or synthetic biology technology for production of those compounds and their derivatives

Dr. Thu V. Vuong
Guest Editor

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Keywords

  • Natural products
  • Natural product derivatives
  • Bioprocess
  • Antibacterial activities
  • Antioxidant properties
  • Anticancer activities

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Published Papers (14 papers)

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32 pages, 1607 KiB  
Review
Isolation and Biological Properties of the Natural Flavonoids Pectolinarin and Pectolinarigenin—A Review
by Thamere Cheriet, Balkeis Ben-Bachir, Oumelkhir Thamri, Ramdane Seghiri and Ines Mancini
Antibiotics 2020, 9(7), 417; https://doi.org/10.3390/antibiotics9070417 - 16 Jul 2020
Cited by 50 | Viewed by 6534
Abstract
Flavonoids are metabolites widely distributed in plants and commonly present in foods, such as fruits and vegetables. Pectolinarin, which belongs to the flavone subclass, has attracted considerable attention due to its presence in many medicinal plants. It has turned out to be a [...] Read more.
Flavonoids are metabolites widely distributed in plants and commonly present in foods, such as fruits and vegetables. Pectolinarin, which belongs to the flavone subclass, has attracted considerable attention due to its presence in many medicinal plants. It has turned out to be a good biological agent especially due to its antioxidant, anti-inflammatory, antidiabetic, and antitumor activities, evaluated both in vitro and in vivo. Its aglycone, the metabolite pectolinarigenin, is also known for a series of biological properties including anti-inflammatory and antidiabetic effects. In the first overview on the two metabolites here presented, their collection, isolation and the results of their biological evaluation are reported. Full article
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14 pages, 2249 KiB  
Review
The Desotamide Family of Antibiotics
by Asif Fazal, Michael E. Webb and Ryan F. Seipke
Antibiotics 2020, 9(8), 452; https://doi.org/10.3390/antibiotics9080452 - 27 Jul 2020
Cited by 15 | Viewed by 5392
Abstract
Microbial natural products underpin the majority of antimicrobial compounds in clinical use and the discovery of new effective antibacterial treatments is urgently required to combat growing antimicrobial resistance. Non-ribosomal peptides are a major class of natural products to which many notable antibiotics belong. [...] Read more.
Microbial natural products underpin the majority of antimicrobial compounds in clinical use and the discovery of new effective antibacterial treatments is urgently required to combat growing antimicrobial resistance. Non-ribosomal peptides are a major class of natural products to which many notable antibiotics belong. Recently, a new family of non-ribosomal peptide antibiotics were discovered—the desotamide family. The desotamide family consists of desotamide, wollamide, surugamide, ulleungmycin and noursamycin/curacomycin, which are cyclic peptides ranging in size between six and ten amino acids in length. Their biosynthesis has attracted significant attention because their highly functionalised scaffolds are cyclised by a recently identified standalone cyclase. Here, we provide a concise review of the desotamide family of antibiotics with an emphasis on their biosynthesis. Full article
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30 pages, 4457 KiB  
Review
From Ocean to Medicine: Pharmaceutical Applications of Metabolites from Marine Bacteria
by José Diogo Santos, Inês Vitorino, Fernando Reyes, Francisca Vicente and Olga Maria Lage
Antibiotics 2020, 9(8), 455; https://doi.org/10.3390/antibiotics9080455 - 28 Jul 2020
Cited by 41 | Viewed by 9013
Abstract
Oceans cover seventy percent of the planet’s surface and besides being an immense reservoir of biological life, they serve as vital sources for human sustenance, tourism, transport and commerce. Yet, it is estimated by the National Oceanic and Atmospheric Administration (NOAA) that eighty [...] Read more.
Oceans cover seventy percent of the planet’s surface and besides being an immense reservoir of biological life, they serve as vital sources for human sustenance, tourism, transport and commerce. Yet, it is estimated by the National Oceanic and Atmospheric Administration (NOAA) that eighty percent of the oceans remain unexplored. The untapped biological resources present in oceans may be fundamental in solving several of the world’s public health crises of the 21st century, which span from the rise of antibiotic resistance in bacteria, pathogenic fungi and parasites, to the rise of cancer incidence and viral infection outbreaks. In this review, health risks as well as how marine bacterial derived natural products may be tools to fight them will be discussed. Moreover, an overview will be made of the research pipeline of novel molecules, from identification of bioactive bacterial crude extracts to the isolation and chemical characterization of the molecules within the framework of the One Health approach. This review highlights information that has been published since 2014, showing the current relevance of marine bacteria for the discovery of novel natural products. Full article
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30 pages, 2997 KiB  
Article
HPLC-DAD and UHPLC/QTOF-MS Analysis of Polyphenols in Extracts of the African Species Combretum padoides, C. zeyheri and C. psidioides Related to Their Antimycobacterial Activity
by Pia Fyhrquist, Enass Y. A. Salih, Satu Helenius, Into Laakso and Riitta Julkunen-Tiitto
Antibiotics 2020, 9(8), 459; https://doi.org/10.3390/antibiotics9080459 - 29 Jul 2020
Cited by 11 | Viewed by 3994
Abstract
Combretum padoides Engl. & Diels, C. psidioides Welv. and C. zeyheri Sond. are used for the treatment of infections and tuberculosis related symptoms in African traditional medicine. In order to verify these uses, extracts were screened for their growth inhibitory effects against M. [...] Read more.
Combretum padoides Engl. & Diels, C. psidioides Welv. and C. zeyheri Sond. are used for the treatment of infections and tuberculosis related symptoms in African traditional medicine. In order to verify these uses, extracts were screened for their growth inhibitory effects against M. smegmatis ATCC 14468. Ultra-high pressure liquid chromatography coupled to quadrupole time-of-flight mass spectrometry (UHPLC/QTOF-MS) and GC-MS were used to investigate the polyphenolic composition in the active extracts. The lowest minimum inhibitory concentration (MIC), 625 µg/mL, was shown by a methanol extract of the stem bark of C. psidioides. A butanol extract of C. psidioides gave large inhibition zone diameters (IZD 21 mm) and inhibited 84% of the mycobacterial growth at 312 µg/mL. Combretastatin B-2 and dihydrostilbene derivatives were present in the methanol extract of C. psidioides, whereas the butanol extract of this species contained punicalagin, corilagin, and sanguiin H-4. Methanol and butanol extracts of the stem bark of C. padoides gave large inhibition zone diameters (IZD 26.5 mm) and MIC values of 1250 and 2500 µg/mL, respectively. C. padoides contained an ellagitannin with a mass identical to punicalagin ([M-H] 1083.0587) and a corilagin like derivative ([M-H] 633.0750) as well as ellagic acid arabinoside and methyl ellagic acid xyloside. A butanol extract of the roots of C. zeyheri showed mild antimycobacterial activity and contained a gallotannin at m/z [M-H] 647.0894 as the main compound along with punicalagin and three unknown ellagitannins at m/z [M-H] 763.0788, 765.0566, and 817.4212. Our results indicate that the studied species of Combretum contain phenolic and polyphenolic compounds with possible potential as leads for antimycobacterial drugs or as adjuvants for conventional anti-TB drugs. Full article
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16 pages, 2191 KiB  
Article
Synthesis of Degraded Limonoid Analogs as New Antibacterial Scaffolds against Staphylococcus aureus
by Marta Ferrera-Suanzes, Victoria Prieto, Antonio J. Medina-Olivera, José Manuel Botubol-Ares, Fátima Galán-Sánchez, Manuel A. Rodríguez-Iglesias, Rosario Hernández-Galán and María Jesús Durán-Peña
Antibiotics 2020, 9(8), 488; https://doi.org/10.3390/antibiotics9080488 - 6 Aug 2020
Cited by 6 | Viewed by 3339
Abstract
Staphylococcus aureus and methicillin-resistant Staphylococcus aureus (MRSA) have become serious infections in humans and ruminants. S. aureus strains are showing rapid changes to develop resistance in traditional antibiotic-containing systems. In the continuous fierce fight against the emergent multi-drug resistant bacterial strains, straightforward and [...] Read more.
Staphylococcus aureus and methicillin-resistant Staphylococcus aureus (MRSA) have become serious infections in humans and ruminants. S. aureus strains are showing rapid changes to develop resistance in traditional antibiotic-containing systems. In the continuous fierce fight against the emergent multi-drug resistant bacterial strains, straightforward and scalable synthetic procedures to produce new active molecules are in demand. Analysis of molecular properties points to degraded limonoids as promising candidates. In this article, we report a simple synthetic approach to obtain degraded limonoid analogs as scaffolds for new antibacterial molecules. The minimum inhibitory concentrations against S. aureus were evaluated for the stereoisomer mixtures by the broth microdilution method. Analysis of results showed that the acetylated derivatives were the most active of them all. Full article
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9 pages, 603 KiB  
Communication
Potent Antibacterial Prenylated Acetophenones from the Australian Endemic Plant Acronychia crassipetala
by Trong D. Tran, Malin A. Olsson, David J. McMillan, Jason K. Cullen, Peter G. Parsons, Paul W. Reddell and Steven M. Ogbourne
Antibiotics 2020, 9(8), 487; https://doi.org/10.3390/antibiotics9080487 - 6 Aug 2020
Cited by 14 | Viewed by 3388
Abstract
Acronychia crassipetala is an endemic plant species in Australia. Its phytochemistry and therapeutic properties are underexplored. The hexane extract of the fruit A. crassipetala T. G. Hartley was found to inhibit the growth of the Gram-positive bacteria Staphylococcus aureus. Following bio-activity guided [...] Read more.
Acronychia crassipetala is an endemic plant species in Australia. Its phytochemistry and therapeutic properties are underexplored. The hexane extract of the fruit A. crassipetala T. G. Hartley was found to inhibit the growth of the Gram-positive bacteria Staphylococcus aureus. Following bio-activity guided fractionation, two prenylated acetophenones, crassipetalonol A (1) and crassipetalone A (2), were isolated. Their structures were determined mainly by NMR and MS spectroscopic analyses. This is the first record of the isolation and structural characterisation of secondary metabolites from the species A. crassipetala. Their antibacterial and cytotoxic assessments indicated that the known compound (2) had more potent antibacterial activity than the antibiotic chloramphenicol, while the new compound (1) showed moderate cytotoxicity. Full article
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30 pages, 3202 KiB  
Review
The Ascidian-Derived Metabolites with Antimicrobial Properties
by Marcello Casertano, Marialuisa Menna and Concetta Imperatore
Antibiotics 2020, 9(8), 510; https://doi.org/10.3390/antibiotics9080510 - 13 Aug 2020
Cited by 43 | Viewed by 6232
Abstract
Among the sub-phylum of Tunicate, ascidians represent the most abundant class of marine invertebrates, with 3000 species by heterogeneous habitat, that is, from shallow water to deep sea, already reported. The chemistry of these sessile filter-feeding organisms is an attractive reservoir of varied [...] Read more.
Among the sub-phylum of Tunicate, ascidians represent the most abundant class of marine invertebrates, with 3000 species by heterogeneous habitat, that is, from shallow water to deep sea, already reported. The chemistry of these sessile filter-feeding organisms is an attractive reservoir of varied and peculiar bioactive compounds. Most secondary metabolites isolated from ascidians stand out for their potential as putative therapeutic agents in the treatment of several illnesses like microbial infections. In this review, we present and discuss the antibacterial activity shown by the main groups of ascidian-derived products, such as sulfur-containing compounds, meroterpenes, alkaloids, peptides, furanones, and their derivatives. Moreover, the direct evidence of a symbiotic association between marine ascidians and microorganisms shed light on the real producers of many extremely potent marine natural compounds. Hence, we also report the antibacterial potential, joined to antifungal and antiviral activity, of metabolites isolated from ascidian-associate microorganisms by culture-dependent methods. Full article
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11 pages, 1163 KiB  
Article
Simplicilones A and B Isolated from the Endophytic Fungus Simplicillium subtropicum SPC3
by Elodie Gisèle M. Anoumedem, Bel Youssouf G. Mountessou, Simeon F. Kouam, Abolfazl Narmani and Frank Surup
Antibiotics 2020, 9(11), 753; https://doi.org/10.3390/antibiotics9110753 - 29 Oct 2020
Cited by 14 | Viewed by 2711
Abstract
Two new tetracyclic polyketides with a spirocenter, simplicilones A (1) and B (2) were isolated from the broth-culture of the endophytic fungus Simplicilliumsubtropicum (SPC3) in the course of our screening for new bioactive secondary metabolites. This endophytoic fungus [...] Read more.
Two new tetracyclic polyketides with a spirocenter, simplicilones A (1) and B (2) were isolated from the broth-culture of the endophytic fungus Simplicilliumsubtropicum (SPC3) in the course of our screening for new bioactive secondary metabolites. This endophytoic fungus is naturally harboured in the fresh bark of the Cameroonian medicinal plant Duguetia staudtii (Engl. and Diels) Chatrou. The planar structures of the simplicilones were elucidated by MS and 1D as well as 2D NMR spectroscopic techniques. The relative configuration was assigned by NOESY experiments in conjunction with coupling constants; subsequently, the absolute configurations were assigned by the modified Mosher’s method. The compounds showed weak cytotoxic effects against the cell line KB3.1 (in vitro cytotoxicity (IC50) = 25 µg/mL for 1, 29 µg/mL for 2), but were inactive against the tested Gram-positive and Gram-negative bacteria as well as fungi. Full article
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3 pages, 182 KiB  
Editorial
Natural Products and Their Derivatives with Antibacterial, Antioxidant and Anticancer Activities
by Thu V. Vuong
Antibiotics 2021, 10(1), 70; https://doi.org/10.3390/antibiotics10010070 - 13 Jan 2021
Cited by 20 | Viewed by 3523
Abstract
Natural products and their derivatives have been commonly used in our daily life, as they play important roles in boosting immune systems and fighting diseases [...] Full article
15 pages, 2055 KiB  
Article
Chemotherapeutic Potential of Epimedium brevicornum Extract: The cGMP-Specific PDE5 Inhibitor as Anti-Infertility Agent Following Long-Term Administration of Tramadol in Male Rats
by Ahmed S. Abdelaziz, Mohamed A. Kamel, Amany I. Ahmed, Shimaa I. Shalaby, Salama M. El-darier, Amany Magdy Beshbishy, Gaber El-Saber Batiha, Suliman Y. Alomar and Dina M. Khodeer
Antibiotics 2020, 9(6), 318; https://doi.org/10.3390/antibiotics9060318 - 11 Jun 2020
Cited by 12 | Viewed by 4469
Abstract
Epimedium brevicornum Maxim (EbM) is a well-known Chinese herb that has been widely used for the treatment of several diseases. The main purpose of this study is to examine the role of Epimedium brevicornum extract in certain andrological parameters in rats as a [...] Read more.
Epimedium brevicornum Maxim (EbM) is a well-known Chinese herb that has been widely used for the treatment of several diseases. The main purpose of this study is to examine the role of Epimedium brevicornum extract in certain andrological parameters in rats as a natural modulator for adverse viewpoints associated with chronic administration of tramadol (TAM). Fifty rats were categorized into five groups. Untreated rats were known as Group I, whereas rats in Groups II and III were administered 2.43 g/kg/day of E. brevicornum extract and 50 mg/kg/day of TAM for 130 consecutive days, respectively. Both of Groups IV and V were administered TAM for 65 successive days, followed by concomitant use of both drugs for another 65 days, with the E. brevicornum extract at doses of 0.81 and 2.43 g/kg/day, respectively. TAM showed an injurious effect on sperm attributes, serum hormones, tissue malondialdehyde, superoxide dismutase, and nitric oxide. Elevation of the apoptotic marker Bax and a reduction of Bcl2 were recorded. Histopathological abnormalities have been reported in rat testicles. Rats treated with E. brevicornum extract with TAM showed an improvement in all the parameters tested. It could be presumed that E. brevicornum extract plus TAM exhibits a promising effect on the enhancement of male anti-infertility effects. Full article
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12 pages, 786 KiB  
Article
Nonocarbolines A–E, β-Carboline Antibiotics Produced by the Rare Actinobacterium Nonomuraea sp. from Indonesia
by Gian Primahana, Chandra Risdian, Tjandrawati Mozef, Enge Sudarman, Matthias Köck, Joachim Wink and Marc Stadler
Antibiotics 2020, 9(3), 126; https://doi.org/10.3390/antibiotics9030126 - 17 Mar 2020
Cited by 17 | Viewed by 5066
Abstract
During the course of our ongoing screening for novel biologically active secondary metabolites, the rare Actinobacterium, Nonomuraea sp. 1808210CR was found to produce five unprecedented β-carboline derivatives, nonocarbolines A–E (1–5). Their structures were elucidated from high-resolution mass spectrometry, 1D and [...] Read more.
During the course of our ongoing screening for novel biologically active secondary metabolites, the rare Actinobacterium, Nonomuraea sp. 1808210CR was found to produce five unprecedented β-carboline derivatives, nonocarbolines A–E (1–5). Their structures were elucidated from high-resolution mass spectrometry, 1D and 2D nuclear magnetic resonance spectroscopy, and the absolute configuration of 4 was determined by using the modified Mosher method. Nonocarboline B (2) displayed moderate antifungal activity against Mucor hiemalis, while nonocarboline D (4) exhibited significant cytotoxic activity against the human lung carcinoma cell line A-549 with the IC50 value of 1.7 µM. Full article
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25 pages, 3817 KiB  
Review
Bioactive Compounds, Pharmacological Actions, and Pharmacokinetics of Wormwood (Artemisia absinthium)
by Gaber El-Saber Batiha, Ahmed Olatunde, Amany El-Mleeh, Helal F. Hetta, Salim Al-Rejaie, Saad Alghamdi, Muhammad Zahoor, Amany Magdy Beshbishy, Toshihiro Murata, Adrian Zaragoza-Bastida and Nallely Rivero-Perez
Antibiotics 2020, 9(6), 353; https://doi.org/10.3390/antibiotics9060353 - 23 Jun 2020
Cited by 111 | Viewed by 18847
Abstract
Plants have been used since ancient times to cure certain infectious diseases, and some of them are now standard treatments for several diseases. Due to the side effects and resistance of pathogenic microorganisms to antibiotics and most drugs on the market, a great [...] Read more.
Plants have been used since ancient times to cure certain infectious diseases, and some of them are now standard treatments for several diseases. Due to the side effects and resistance of pathogenic microorganisms to antibiotics and most drugs on the market, a great deal of attention has been paid to extracts and biologically active compounds isolated from plant species used in herbal medicine. Artemisia absinthium is an important perennial shrubby plant that has been widely used for the treatment of several ailments. Traditionally, A. absinthium has always been of pharmaceutical and botanical importance and used to manage several disorders including hepatocyte enlargement, hepatitis, gastritis, jaundice, wound healing, splenomegaly, dyspepsia, indigestion, flatulence, gastric pain, anemia, and anorexia. It has also been documented to possess antioxidant, antifungal, antimicrobial, anthelmintic, anti-ulcer, anticarcinogenic, hepatoprotective, neuroprotective, antidepressant, analgesic, immunomodulatory, and cytotoxic activity. Long-term use of A. absinthium essential oil may cause toxic and mental disorders in humans with clinical manifestations including convulsions, sleeplessness, and hallucinations. Combination chemotherapies of artemisia extract or its isolated active constituents with the currently available antibabesial or anti-malarial drugs are now documented to relieve malaria and piroplasmosis infections. The current review examines the phytoconstituents, toxic and biological activities of A. absinthium. Full article
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40 pages, 7432 KiB  
Review
Stilbenoids: A Natural Arsenal against Bacterial Pathogens
by Luce Micaela Mattio, Giorgia Catinella, Sabrina Dallavalle and Andrea Pinto
Antibiotics 2020, 9(6), 336; https://doi.org/10.3390/antibiotics9060336 - 18 Jun 2020
Cited by 62 | Viewed by 6237
Abstract
The escalating emergence of resistant bacterial strains is one of the most important threats to human health. With the increasing incidence of multi-drugs infections, there is an urgent need to restock our antibiotic arsenal. Natural products are an invaluable source of inspiration in [...] Read more.
The escalating emergence of resistant bacterial strains is one of the most important threats to human health. With the increasing incidence of multi-drugs infections, there is an urgent need to restock our antibiotic arsenal. Natural products are an invaluable source of inspiration in drug design and development. One of the most widely distributed groups of natural products in the plant kingdom is represented by stilbenoids. Stilbenoids are synthesised by plants as means of protection against pathogens, whereby the potential antimicrobial activity of this class of natural compounds has attracted great interest in the last years. The purpose of this review is to provide an overview of recent achievements in the study of stilbenoids as antimicrobial agents, with particular emphasis on the sources, chemical structures, and the mechanism of action of the most promising natural compounds. Attention has been paid to the main structure modifications on the stilbenoid core that have expanded the antimicrobial activity with respect to the parent natural compounds, opening the possibility of their further development. The collected results highlight the therapeutic versatility of natural and synthetic resveratrol derivatives and provide a prospective insight into their potential development as antimicrobial agents. Full article
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13 pages, 1046 KiB  
Article
In Vitro Toxicity, Antioxidant, Anti-Inflammatory, and Antidiabetic Potential of Sphaerostephanos unitus (L.) Holttum
by Marimuthu Alias Antonisamy Johnson, C. Xavier Madona, Ray S. Almeida, Natália Martins and Henrique D. M. Coutinho
Antibiotics 2020, 9(6), 333; https://doi.org/10.3390/antibiotics9060333 - 18 Jun 2020
Cited by 16 | Viewed by 3581
Abstract
Pteridophytes have been widely used in several systems of medicine. Several reports have increasingly assessed their bioactive effects, but for Sphaerostephanos unitus (L.) Holttum, only its antibacterial potential has been assessed. In this sense, the present study was carried out to reveal the [...] Read more.
Pteridophytes have been widely used in several systems of medicine. Several reports have increasingly assessed their bioactive effects, but for Sphaerostephanos unitus (L.) Holttum, only its antibacterial potential has been assessed. In this sense, the present study was carried out to reveal the phytochemical profile and to determine the toxicity, antioxidant, antidiabetic, and anti-inflammatory potential of S. unitus. Brine shrimp lethality, 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, phosphomolybdenum assay, superoxide radical scavenging activity, 2,2-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) assay (ABTS), and in vitro α-amylase inhibitory and membrane stabilization assays were applied. S. unitus extract toxicity showed variable mortality percentages, with LC50 values ranging from 4 to 30 mg/mL. DPPH radical scavenging effects of S. unitus extracts were as follows: methanol > acetone > petroleum ether > chloroform. S. unitus acetone extract displayed the strongest phosphomolybdenum reduction (10 ± 2 mg Ascorbic Acid Equivalent/g). The studied extracts also revealed efficient, superoxide scavenging effects in a dose-dependent manner. In S. unitus, the highest ABTS radical scavenging rate was observed in the chloroform extract (3000 ± 40 µmol/g). The S. unitus anti-inflammatory effect was as follows: petroleum ether > chloroform > methanol > acetone. In S. unitus extract, the highest percentage of α-amylase activity (80%) was observed for the petroleum ether extract (25 µg/mL). Faced with these findings, further studies should be performed to isolate and identify the S. unitus compounds responsible for their antioxidant, antidiabetic and anti-inflammatory effects. Full article
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