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Bailly C. A systematic review of spirostanol saponins and anticancer natural products isolated from Tacca plantaginea (Hance) Drenth. PHYTOCHEMISTRY 2024; 228:114252. [PMID: 39173698 DOI: 10.1016/j.phytochem.2024.114252] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Received: 02/26/2024] [Revised: 08/12/2024] [Accepted: 08/14/2024] [Indexed: 08/24/2024]
Abstract
The plant genus Tacca comprises twenty species including Tacca plantaginea, essentially distributed in the Indo-China region. Medicinal preparations from the rhizomes are used traditionally to treat gastrointestinal ailments, stomach aches and inflammatory disorders. A variety of bioactive molecules have been isolated from T. plantaginea, including potent anticancer steroids such as the taccanolides which interfere with microtubules dynamic. Other efficient anticancer natural products have been isolated from the plant, in particular a series of diosgenin/yamogenin-type sapogenins including taccaoside (monodesmosidic) and taccaoside A (bidesmosidic). Taccaoside A displays marked anticancer properties through two complementary mechanisms: a direct action on cancer stem cells via HRas and Pi3K/Akt signaling and an indirect immunomodulatory action via activation of cytotoxic T cells. A similar mechanism of action has been invoked with a total saponin extract from Schizocapsa plantaginea Hance (synonym to T. plantaginea) and the saponin SSPH 1. This saponin reduced tumor growth in mice through stimulation of cytotoxic T lymphocytes. Other bioactive products have been isolated from T. plantaginea, including withanolide-type steroids (plantagiolides, chantriolides), diarylheptanoids (plantagineosides) and different saponins (diosbulbisides, lieguonins). The discussion centers around the mechanism of action of spirostanol saponins, with the objective to promote their study as immuno-active anticancer agents.
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Affiliation(s)
- Christian Bailly
- University of Lille, CNRS, Inserm, CHU Lille, UMR9020 - UMR1277 - Canther - Cancer Heterogeneity, Plasticity and Resistance to Therapies, 59000, Lille, France; University of Lille, Faculty of Pharmacy, Institut de Chimie Pharmaceutique Albert Lespagnol (ICPAL), 3 rue du Professeur Laguesse, 59000, Lille, France; OncoWitan, Consulting Scientific Office, Lille, (Wasquehal), 59290, France.
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Arrieche D, Olea AF, Jara-Gutiérrez C, Villena J, Pardo-Baeza J, García-Davis S, Viteri R, Taborga L, Carrasco H. Ethanolic Extract from Fruits of Pintoa chilensis, a Chilean Extremophile Plant. Assessment of Antioxidant Activity and In Vitro Cytotoxicity. PLANTS (BASEL, SWITZERLAND) 2024; 13:1409. [PMID: 38794478 PMCID: PMC11125100 DOI: 10.3390/plants13101409] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [Grants] [Track Full Text] [Subscribe] [Scholar Register] [Received: 04/05/2024] [Revised: 05/08/2024] [Accepted: 05/15/2024] [Indexed: 05/26/2024]
Abstract
Pintoa chilensis is a shrub with yellow flowers that reach up to two meters high, endemic of the Atacama Region in Chile. This species grows under special environmental conditions such as low altitude, arid areas, and directly sun-exposed habitats. In the present study, ethanolic extract was obtained from fruits of P. chilensis, and then partitioned in solvents of increasing polarity to obtain five fractions: hexane (HF), dichloromethane (DF), ethyl acetate (AF), and the residual water fraction (QF). The antioxidant activity of extracts was evaluated by using the DPPH, ABTS, and FRAP methods. The results show that the antioxidant capacity of P. chilensis is higher than that reported for other plants growing in similar environments. This effect is attributed to the highest content of flavonoids and total phenols found in P. chilensis. On the other hand, the cell viability of a breast cancer cell line (MCF-7) and a non-tumor cell line (MCF-10A) was assessed in the presence of different extract fractions. The results indicate that the hexane fraction (HF) exhibits the highest cytotoxicity on both cell lines (IC50 values equal to 35 and 45 µg/mL), whereas the dichloromethane fraction (DF) is the most selective one. The GC-MS analysis of the dichloromethane fraction (DF) shows the presence of fatty acids, sugars, and polyols as major components.
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Affiliation(s)
- Dioni Arrieche
- Laboratorio de Productos Naturales, Departamento de Química, Universidad Técnica Federico Santa María, Avenida España 1680, Valparaíso 2340000, Chile;
| | - Andrés F. Olea
- Grupo QBAB, Instituto de Ciencias Aplicadas, Facultad de Ingeniería, Universidad Autónoma de Chile, San Miguel, Santiago 8900000, Chile;
| | - Carlos Jara-Gutiérrez
- Centro Interdisciplinario de Investigación Biomédica e Ingeniería para la Salud (MEDING), Escuela de Kinesiología, Facultad de Medicina, Universidad de Valparaíso, Valparaíso 2362905, Chile; (C.J.-G.); (J.V.)
| | - Joan Villena
- Centro Interdisciplinario de Investigación Biomédica e Ingeniería para la Salud (MEDING), Escuela de Kinesiología, Facultad de Medicina, Universidad de Valparaíso, Valparaíso 2362905, Chile; (C.J.-G.); (J.V.)
| | - Javier Pardo-Baeza
- Programa de Conservación de Flora Nativa del Norte de Chile, Biorestauración Consultores, Copiapó 1530000, Chile;
| | - Sara García-Davis
- Instituto Universitario de Bio—Orgánica “Antonio González” (IUBO-AG), Universidad de La Laguna (ULL), 38200 San Cristóbal de La Laguna, Spain;
| | - Rafael Viteri
- Escuela de Ciencias Ambientales, Universidad Espíritu Santo, Guayaquil 092301, Ecuador;
| | - Lautaro Taborga
- Laboratorio de Productos Naturales, Departamento de Química, Universidad Técnica Federico Santa María, Avenida España 1680, Valparaíso 2340000, Chile;
| | - Héctor Carrasco
- Grupo QBAB, Instituto de Ciencias Aplicadas, Facultad de Ingeniería, Universidad Autónoma de Chile, San Miguel, Santiago 8900000, Chile;
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Yang BJ, Fan SR, Zhang XF, Cai JY, Ruan T, Xiang ZR, Ren J, Hao XJ, Chen DZ. Design, synthesis and structure-activity relationship optimization of phenanthridine derivatives as new anti-vitiligo compounds. Bioorg Chem 2021; 119:105582. [PMID: 34971944 DOI: 10.1016/j.bioorg.2021.105582] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 10/09/2021] [Revised: 12/20/2021] [Accepted: 12/21/2021] [Indexed: 12/29/2022]
Abstract
Humans have been suffering from vitiligo for a long time. Target vitiligo drugs have yet been approved. Activation of Wnt/β-catenin signalling has potential in the therapeutic use of vitiligo, so exploring new drugs that specifically directly activate Wnt is worthwhile to obtain new anti-vitiligo agents. In this work, two portions design and synthesis were put into effect. firstly, 17 phenanthridine derivatives with C-4 substitutes were designed and synthesized, which compounds 4, 6, 12, 13 served as H-acceptor with protein showed enhance melanogenesis activity; Secondly, 7 hybrid new scaffolds of compounds were designed and synthesized, scaffold hopping compound 36 that aromatic benzene was replaced pyrazole on ring C showed enhance melanogenesis and tyrosinase activity; The last and most important, a comprehensive optimization and SARs of compound 36 were carried out, compounds 41 and 43 shared phenolic hydroxyl or 3-methyl-pyridine substitutes at C-7 position remarkably improved the capacity of melanogenesis and tyrosinase activity. Compound 43 were identified as new anti-vitiligo agents that specifically activate the Wnt/β-catenin signalling pathway by targeting Axin. Structure-activity relationship analysis implied that H-acceptor substitutions at the C-4 position and phenolic hydroxyl or pyridine substitutions at the C-7 position would improve the activities of the compounds. These findings reveal a new therapeutic strategy for vitiligo, and compounds 41 and 43 may represent potential compounds for vitiligo treatment.
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Affiliation(s)
- Bi-Juan Yang
- State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission and Ministry of Education, Yunnan Minzu University, Kunming 650031, Yunnan, China
| | - Shi-Rui Fan
- State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; University of Chinese Academy of Sciences, Beijing 100049, China
| | - Xin-Fang Zhang
- State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; School of Life Sciences, Yunnan University, Kunming 650000, China
| | - Jie-Yun Cai
- State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China
| | - Ting Ruan
- State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; University of Chinese Academy of Sciences, Beijing 100049, China
| | - Zheng-Rui Xiang
- State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; University of Chinese Academy of Sciences, Beijing 100049, China
| | - Juan Ren
- State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; School of Life Sciences, Yunnan University, Kunming 650000, China
| | - Xiao-Jiang Hao
- State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China.
| | - Duo-Zhi Chen
- State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China.
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Al-Mekhlafi FA, Abutaha N, Al-Doaiss AA, Ahmed Al-Keridis L, Alsayadi AI, Ali El Hadi Mohamed R, Wadaan MA, Elfaki Ibrahim K, Al-Khalifa MS. Target and non-target effects of Foeniculum vulgare and Matricaria chamomilla combined extract on Culex pipiens mosquitoes. Saudi J Biol Sci 2021; 28:5773-5780. [PMID: 34588890 PMCID: PMC8459038 DOI: 10.1016/j.sjbs.2021.06.024] [Citation(s) in RCA: 2] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 05/05/2021] [Revised: 06/02/2021] [Accepted: 06/08/2021] [Indexed: 12/29/2022] Open
Abstract
The present study focused on extracting green larvicides from extracts of the combination of Foeniculum vulgare and Matricaria chamomilla using different solvents of increasing polarity in a Soxhlet extractor and evaluating their ovicidal, larvicidal, and cytotoxic activities. The most promising among all tested extracts was hexane extract. The ovicidal activity of the hexane PH2 extract resulted in a significant (p < 0.05) decrease in egg hatchability from 95.00 ± 6.16% to 15 ± 9.04% at doses ranging from 62.5 to 500 µg/mL. The larval mortality with the hexane extract ranged from 13.33 ± 3.3% to 93.33 ± 3.3% at doses ranging from 31.25 to 250 µg/mL, respectively. The LC50 and LC90 values of the larvicidal activity of the hexane extract were estimated to be 148.3 and 242.17 µg/mL, respectively, after 24 h of exposure. Similarly, the LC50 values after 48 and 72 h of exposure were 124.93 and 100.3 µg/mL, respectively, against the third instar of Cx. pipiens. PH2 treatment of larvae resulted in histopathological changes such as degenerated epithelial cells and destruction of microvilli on the epithelial cells. The PH2 extract achieved a dose-dependent decrease in the rate of cell survival. The IC50 value of PH2-treated HUVECs was 192.07 µg/mL after 24 h of incubation. The cells showed changes in cellular and nuclear morphology. In conclusion, the hexane extract of PH2 could be used in mosquito management programs.
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Affiliation(s)
- Fahd A Al-Mekhlafi
- Bioproducts Research Chair Department of Zoology, College of Science, King Saud University, Saudi Arabia.,Department of Agricultural Production, College of Agriculture and Veterinary Medicine, Thamar University, Yemen
| | - Nael Abutaha
- Bioproducts Research Chair Department of Zoology, College of Science, King Saud University, Saudi Arabia
| | - Amin A Al-Doaiss
- Department of Biology, College of Science, King Khalid University, Abha, Saudi Arabia.,Department of Histology and Anatomy, Faculty of Medicine, Sana'a University, Sana'a, Yemen
| | - Lamya Ahmed Al-Keridis
- Biology Department, Faculty of Science, Princess Nourah Bint Abdurrahman University, Riyadh, Saudi Arabia
| | - Ahmed I Alsayadi
- Bioproducts Research Chair Department of Zoology, College of Science, King Saud University, Saudi Arabia
| | - Rania Ali El Hadi Mohamed
- Biology Department, Faculty of Science, Princess Nourah Bint Abdurrahman University, Riyadh, Saudi Arabia
| | - Muhammad A Wadaan
- Bioproducts Research Chair Department of Zoology, College of Science, King Saud University, Saudi Arabia
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Neres NBR, Montagnini D, Ferreira DS, Parreira RLT, Orenha RP, Lima TC, Molina EF, Cunha WR, Silva MLA, Esperandim VR. In Vivo and in Silico Trypanocidal Activity Evaluation of (-)-Cubebin Encapsulated in PLGA Microspheres as Potential Treatment in Acute Phase. Chem Biodivers 2021; 18:e2100052. [PMID: 33905595 DOI: 10.1002/cbdv.202100052] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 01/21/2021] [Accepted: 04/08/2021] [Indexed: 11/11/2022]
Abstract
In this study, the trypomastigotes of a Y strain of Trypanosoma cruzi were inoculated intraperitoneally into male BALB/c mice weighing approximately 25 g each, which were divided into groups for evaluation of the trypanocidal activity. For the treatment of experimental groups, encapsulated and unencapsulated (-)-cubebin, Benznidazole, and two groups as negative controls were used. The encapsulated (-)-cubebin showed a 68.1 % encapsulation efficiency. The parasitemia peak of substances remained around the 9th day after the observed reduction in the number of circulating trypomastigotes. The encapsulated (-)-cubebin and (-)-cubebin unloaded showed a decrease of 61.3 % and 58.5 % in the number of parasites as compared to the negative control, respectively. Moreover, animals treated with encapsulated (-)-cubebin had a higher survival time as compared to the other groups. In conclusion, the results obtained were more promising for encapsulated (-)-cubebin as compared to unloaded particles.
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Affiliation(s)
- Nayara B R Neres
- Núcleo de Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, 14404-600, Franca-SP, Brazil
| | - Daniel Montagnini
- Núcleo de Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, 14404-600, Franca-SP, Brazil
| | - Daniele S Ferreira
- Núcleo de Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, 14404-600, Franca-SP, Brazil
| | - Renato L T Parreira
- Núcleo de Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, 14404-600, Franca-SP, Brazil
| | - Renato P Orenha
- Núcleo de Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, 14404-600, Franca-SP, Brazil
| | - Thais C Lima
- Núcleo de Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, 14404-600, Franca-SP, Brazil
| | - Eduardo F Molina
- Núcleo de Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, 14404-600, Franca-SP, Brazil
| | - Wilson R Cunha
- Núcleo de Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, 14404-600, Franca-SP, Brazil
| | - Márcio L A Silva
- Núcleo de Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, 14404-600, Franca-SP, Brazil
| | - Viviane R Esperandim
- Núcleo de Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, 14404-600, Franca-SP, Brazil
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New Eugenol Derivatives with Enhanced Insecticidal Activity. Int J Mol Sci 2020; 21:ijms21239257. [PMID: 33291666 PMCID: PMC7729565 DOI: 10.3390/ijms21239257] [Citation(s) in RCA: 21] [Impact Index Per Article: 4.2] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/02/2020] [Revised: 12/01/2020] [Accepted: 12/01/2020] [Indexed: 02/07/2023] Open
Abstract
Eugenol, the generic name of 4-allyl-2-methoxyphenol, is the major component of clove essential oil, and has demonstrated relevant biological potential with well-known antimicrobial and antioxidant actions. New O-alkylated eugenol derivatives, bearing a propyl chain with terminals like hydrogen, hydroxyl, ester, chlorine, and carboxylic acid, were synthesized in the present work. These compounds were later subjected to epoxidation conditions to give the corresponding oxiranes. All derivatives were evaluated against their effect upon the viability of insect cell line Sf9 (Spodoptera frugiperda), demonstrating that structural changes elicit marked effects in terms of potency. In addition, the most promising molecules were evaluated for their impact in cell morphology, caspase-like activity, and potential toxicity towards human cells. Some molecules stood out in terms of toxicity towards insect cells, with morphological assessment of treated cells showing chromatin condensation and fragmentation, which are compatible with the occurrence of programmed cell death, later confirmed by evaluation of caspase-like activity. These findings point out the potential use of eugenol derivatives as semisynthetic insecticides from plant natural products.
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Iheagwam FN, Rotimi SO. Computer-Aided Analysis of Multiple SARS-CoV-2 Therapeutic Targets: Identification of Potent Molecules from African Medicinal Plants. SCIENTIFICA 2020; 2020:1878410. [PMID: 32963884 PMCID: PMC7492903 DOI: 10.1155/2020/1878410] [Citation(s) in RCA: 6] [Impact Index Per Article: 1.2] [Reference Citation Analysis] [Abstract] [Track Full Text] [Subscribe] [Scholar Register] [Received: 06/24/2020] [Revised: 08/03/2020] [Accepted: 08/13/2020] [Indexed: 05/05/2023]
Abstract
The COVID-19 pandemic, which started in Wuhan, China, has spread rapidly over the world with no known antiviral therapy or vaccine. Interestingly, traditional Chinese medicine helped in flattening the pandemic curve in China. In this study, molecules from African medicinal plants were analysed as potential candidates against multiple SARS-CoV-2 therapeutic targets. Sixty-five molecules from the ZINC database subset (AfroDb Natural Products) were virtually screened with some reported repurposed therapeutics against six SARS-CoV-2 and two human targets. Molecular docking, druglikeness, absorption, distribution, metabolism, excretion, and toxicity (ADMET) of the best hits were further simulated. Of the 65 compounds, only three, namely, 3-galloylcatechin, proanthocyanidin B1, and luteolin 7-galactoside found in almond (Terminalia catappa), grape (Vitis vinifera), and common verbena (Verbena officinalis), were able to bind to all eight targets better than the reported repurposed drugs. The findings suggest these molecules may play a role as therapeutic leads in tackling this pandemic due to their multitarget activity.
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Affiliation(s)
- Franklyn Nonso Iheagwam
- Department of Biochemistry, College of Science and Technology, Covenant University, Canaanland, P.M.B. 1023, Ota, Ogun, Nigeria
- Covenant University Public Health and Wellness Research Cluster (CUPHWERC), College of Science and Technology, Covenant University, Canaanland, P.M.B. 1023, Ota, Ogun, Nigeria
| | - Solomon Oladapo Rotimi
- Department of Biochemistry, College of Science and Technology, Covenant University, Canaanland, P.M.B. 1023, Ota, Ogun, Nigeria
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Sanna G, Madeddu S, Murgia G, Serreli G, Begala M, Caboni P, Incani A, Franci G, Galdiero M, Giliberti G. Potent and Selective Activity against Human Immunodeficiency Virus 1 (HIV-1) of Thymelaea hirsuta Extracts. Viruses 2020; 12:v12060664. [PMID: 32575585 PMCID: PMC7354558 DOI: 10.3390/v12060664] [Citation(s) in RCA: 10] [Impact Index Per Article: 2.0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 05/20/2020] [Revised: 06/09/2020] [Accepted: 06/16/2020] [Indexed: 12/27/2022] Open
Abstract
Historically, natural products have been the most successful source of inspiration for the development of new drugs. Members of the Thymelaeaceae family have been of interest owing to their excellent medicinal value. Given the successful history of natural product-based drug discovery, extracts from the aerial parts of Thymelaea hirsuta were evaluated for their potential anti-human immunodeficiency virus type 1 (HIV-1) activity. Ethyl acetate extracts from leaves (71B) and branches (72B) of Thymelaea hirsuta showed potent and selective activity against HIV-1 wt (EC50 = 0.8 µg/mL) at non-cytotoxic concentrations (CC50 > 100 µg/mL). They proved to be active against HIV-1 variants carrying clinically relevant NNRTI and NRTI mutations at low concentration (0.3–4 µg/mL range) and against the M-tropic strain HIV-1 BaL. The 72B extract, chosen as a lead, was not able to inhibit the RT and protease enzymatic functions. Furthermore, it was not virucidal, since exposure of HIV to high concentration did not affect virus infectivity. The pre-clinical safety profile of this extract showed no adverse effect on the growth of Lactobacilli, and non-toxic concentration of the extract did not influence the Caco-2 epithelial cells monolayer integrity. Additionally, extract 72B prevented syncytia formation at low concentration (0.4 µg/mL). The potent inhibitory effect on the syncytia formation in co-cultures showed that 72B inhibits an early event in the replication cycle of HIV. All of these findings prompt us to carry on new studies on Thymelaea hirsuta extracts.
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Affiliation(s)
- Giuseppina Sanna
- Department of Biomedical Sciences, University of Cagliari, Cittadella Universitaria, Monserrato, 09042 Cagliari, Italy; (S.M.); (G.S.); (A.I.); (G.G.)
- Correspondence:
| | - Silvia Madeddu
- Department of Biomedical Sciences, University of Cagliari, Cittadella Universitaria, Monserrato, 09042 Cagliari, Italy; (S.M.); (G.S.); (A.I.); (G.G.)
| | - Giuseppe Murgia
- Department of Inorganic and Analytical Chemistry, University of Cagliari, Cittadella Universitaria, Monserrato, 09042 Cagliari, Italy;
| | - Gabriele Serreli
- Department of Biomedical Sciences, University of Cagliari, Cittadella Universitaria, Monserrato, 09042 Cagliari, Italy; (S.M.); (G.S.); (A.I.); (G.G.)
| | - Michela Begala
- Department of Life and Environmental Sciences-Unit of Drug Sciences, University of Cagliari, Cittadella Universitaria, Monserrato, 09042 Cagliari, Italy; (M.B.); (P.C.)
| | - Pierluigi Caboni
- Department of Life and Environmental Sciences-Unit of Drug Sciences, University of Cagliari, Cittadella Universitaria, Monserrato, 09042 Cagliari, Italy; (M.B.); (P.C.)
| | - Alessandra Incani
- Department of Biomedical Sciences, University of Cagliari, Cittadella Universitaria, Monserrato, 09042 Cagliari, Italy; (S.M.); (G.S.); (A.I.); (G.G.)
| | - Gianluigi Franci
- Department of Medicine, Surgery and Dentistry “Scuola Medica Salernitana”, University of Salerno, 84081 Baronissi, Italy;
| | - Marilena Galdiero
- Department of Experimental Medicine, University of Study of Campania “Luigi Vanvitelli”, Via Costantinopoli 16, 80138 Napoli, Italy;
| | - Gabriele Giliberti
- Department of Biomedical Sciences, University of Cagliari, Cittadella Universitaria, Monserrato, 09042 Cagliari, Italy; (S.M.); (G.S.); (A.I.); (G.G.)
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Ahmed M, Qin P, Ji M, An R, Guo H, Shafi J. Spinasterol, 22,23-Dihydrospinasterol and Fernenol from Citrullus Colocynthis L. with Aphicidal Activity against Cabbage Aphid Brevicoryne Brassicae L. Molecules 2020; 25:molecules25092184. [PMID: 32392823 PMCID: PMC7249147 DOI: 10.3390/molecules25092184] [Citation(s) in RCA: 12] [Impact Index Per Article: 2.4] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 04/07/2020] [Revised: 04/28/2020] [Accepted: 04/29/2020] [Indexed: 11/16/2022] Open
Abstract
Brevicoryne brassicae is a problematic pest in cabbage and other field crops. Synthetic pesticides are used to control this pest, but they are injurious for human health and the environment. The present study aimed to purify and identify the active compounds from Citrullus colocynthis leaves with an appraisal of their efficacy against B. brassicae. Separation and purification were performed via different chromatographic techniques. Molecular analysis and chemical structures were recognized by mass spectrum (MS) and nuclear magnetic resonance (NMR), respectively. Moreover, in vitro and in vivo aphicidal activity was assessed using various concentrations, i.e., 6.25, 12.5, 25 and 50 µg/mL at 12, 24, 48 and 72 h exposure. The outcome shows that mass spectrum analyses of the purified compounds suggested the molecular formulae are C30H50O and C29H50O, C29H48O. The compounds were characterized as fernenol and a mixture of spinasterol, 22,23-dihydrospinasterol by 1H-NMR and 13C-NMR spectrum analysis. The toxicity results showed that the mixture of spinasterol and 22,23-dihydrospinasterol showed LC50 values of 32.36, 44.49 and 37.50 µg/mL by contact, residual and greenhouse assay at 72 h exposure, respectively. In contrast, fernenol recorded LC50 values as 47.99, 57.46 and 58.67 µg/mL, respectively. On the other hand, spinasterol, 22,23-dihydrospinasterol showed the highest mortality, i.e., 66.67%, 53.33% and 60% while, 30%, 23.33% and 25% mortality was recorded by fernenol after 72 h at 50 µg/mL by contact, residual and greenhouse assay, respectively. This study suggests that spinasterol, 22,23-dihydrospinasterol are more effective against B. brassicae which may be introduced as an effective and suitable substitute of synthetic chemical pesticides.
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Affiliation(s)
- Maqsood Ahmed
- College of Plant Protection, Shenyang Agricultural University, Shenyang 110866, China; (M.A.); (R.A.); (H.G.)
- Department of Agriculture, Pest Warning & Quality Control of Pesticides, Gujrat 50700, Pakistan
| | - Peiwen Qin
- College of Plant Protection, Shenyang Agricultural University, Shenyang 110866, China; (M.A.); (R.A.); (H.G.)
- Correspondence: (P.Q.); (M.J.); Tel.: +86-24-8848-7148 (M.J.); Fax: +86-24-8834-2315 (M.J.)
| | - Mingshan Ji
- College of Plant Protection, Shenyang Agricultural University, Shenyang 110866, China; (M.A.); (R.A.); (H.G.)
- Correspondence: (P.Q.); (M.J.); Tel.: +86-24-8848-7148 (M.J.); Fax: +86-24-8834-2315 (M.J.)
| | - Ran An
- College of Plant Protection, Shenyang Agricultural University, Shenyang 110866, China; (M.A.); (R.A.); (H.G.)
| | - Hongxia Guo
- College of Plant Protection, Shenyang Agricultural University, Shenyang 110866, China; (M.A.); (R.A.); (H.G.)
| | - Jamil Shafi
- Department of Plant Pathology, University of Agriculture Faisalabad, Sub-Campus Depalpur, Okara, Faisalabad 56300, Pakistan;
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Voltammetric and spectroscopic determination of polyphenols and antioxidants in ginger ( Zingiber officinale Roscoe). Heliyon 2019; 5:e01717. [PMID: 31193231 PMCID: PMC6522777 DOI: 10.1016/j.heliyon.2019.e01717] [Citation(s) in RCA: 15] [Impact Index Per Article: 2.5] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/16/2018] [Revised: 03/30/2019] [Accepted: 05/09/2019] [Indexed: 11/23/2022] Open
Abstract
Ginger (Zingiber officinale) is widely consumed as an important spice or a common condiment in food and beverages. This study focuses on the determination of pungent and bioactive components in ginger and their antioxidant activity using voltammetric and spectroscopic methods. Gas chromatography-mass spectroscopy analysis revealed that the major components of the pungent compounds were zingerone, shogaols, gingerols, paradols, wikstromol, and carinol. Using spectroscopic methods, the antioxidant capacity of ginger aqueous extract was found to be 16.0 μmol gallic acid equivalent (GAE) per gram of ginger extract, and the total phenolic and flavonoid content was estimated to be 7.8 mg GAE/g ginger extract and 15.4 mg Quercetin equivalent (QE) per gram of ginger extract, respectively. Electroanalytical quantification estimated the antioxidant capacity of the ginger infusion to be 23.5 μmol GAE/g ginger extract, which is slightly higher than that estimated using chemical assay. The results may provide useful information for the development of ginger processing and utilization as a flavoring agent, and for our understanding of ginger as a source of natural antioxidants.
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Russo D, Miglionico R, Carmosino M, Bisaccia F, Andrade PB, Valentão P, Milella L, Armentano MF. A Comparative Study on Phytochemical Profiles and Biological Activities of Sclerocarya birrea (A.Rich.) Hochst Leaf and Bark Extracts. Int J Mol Sci 2018; 19:E186. [PMID: 29316691 PMCID: PMC5796135 DOI: 10.3390/ijms19010186] [Citation(s) in RCA: 18] [Impact Index Per Article: 2.6] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 12/16/2017] [Revised: 12/29/2017] [Accepted: 01/02/2018] [Indexed: 11/16/2022] Open
Abstract
Sclerocarya birrea (A.Rich.) Hochst (Anacardiaceae) is a savannah tree that has long been used in sub-Saharan Africa as a medicinal remedy for numerous ailments. The purpose of this study was to increase the scientific knowledge about this plant by evaluating the total content of polyphenols, flavonoids, and tannins in the methanol extracts of the leaves and bark (MLE and MBE, respectively), as well as the in vitro antioxidant activity and biological activities of these extracts. Reported results show that MLE is rich in flavonoids (132.7 ± 10.4 mg of quercetin equivalents/g), whereas MBE has the highest content of tannins (949.5 ± 29.7 mg of tannic acid equivalents/g). The antioxidant activity was measured using four different in vitro tests: β-carotene bleaching (BCB), 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), O₂-•, and nitric oxide (NO•) assays. In all cases, MBE was the most active compared to MLE and the standards used (Trolox and ascorbic acid). Furthermore, MBE and MLE were tested to evaluate their activity in HepG2 and fibroblast cell lines. A higher cytotoxic activity of MBE was evidenced and confirmed by more pronounced alterations in cell morphology. MBE induced cell death, triggering the intrinsic apoptotic pathway by reactive oxygen species (ROS) generation, which led to a loss of mitochondrial membrane potential with subsequent cytochrome c release from the mitochondria into the cytosol. Moreover, MBE showed lower cytotoxicity in normal human dermal fibroblasts, suggesting its potential as a selective anticancer agent.
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Affiliation(s)
- Daniela Russo
- University of Basilicata, Department of Science, V.le dell'AteneoLucano, 85100 Potenza, Italy.
| | - Rocchina Miglionico
- University of Basilicata, Department of Science, V.le dell'AteneoLucano, 85100 Potenza, Italy.
| | - Monica Carmosino
- University of Basilicata, Department of Science, V.le dell'AteneoLucano, 85100 Potenza, Italy.
| | - Faustino Bisaccia
- University of Basilicata, Department of Science, V.le dell'AteneoLucano, 85100 Potenza, Italy.
| | - Paula B Andrade
- REQUIMTE/LAQV, Laboratório de Farmacognosia, Departamento de Química, Faculdade de Farmácia, Universidade do Porto, R. Jorge Viterbo Ferreira, nº 228, 4050-313 Porto, Portugal.
| | - Patrícia Valentão
- REQUIMTE/LAQV, Laboratório de Farmacognosia, Departamento de Química, Faculdade de Farmácia, Universidade do Porto, R. Jorge Viterbo Ferreira, nº 228, 4050-313 Porto, Portugal.
| | - Luigi Milella
- University of Basilicata, Department of Science, V.le dell'AteneoLucano, 85100 Potenza, Italy.
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Antiproliferative activity of spinasterol isolated of Stegnosperma halimifolium (Benth, 1844). Saudi Pharm J 2017; 25:1137-1143. [PMID: 30166901 PMCID: PMC6111116 DOI: 10.1016/j.jsps.2017.07.001] [Citation(s) in RCA: 14] [Impact Index Per Article: 1.8] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/22/2016] [Accepted: 07/09/2017] [Indexed: 12/12/2022] Open
Abstract
Cancer is the major cause of death in the world, representing a significant public health problem. Plants have been shown as a great source of secondary metabolites with anticancer activity. The aim of this work was evaluated the antiproliferative activity of the methanolic extracts, chemical fractions and the compound spinasterol isolated of medicinal plant Stegnosperma halimifolium. The methanolic extracts of stem, leaf and stem/leaf was obtained by maceration. The methanolic extract of stem was purified by successive extractions with solvents as n-hexane, ethyl acetate and ethanol. The n-hexane fraction was separated by column chromatographic and monitored by thin layer chromatographic. The compound spinasterol was characterized by 1H NMR, 13C NMR and Mass Spectrometry. Methanolic extracts, chemical, chromatographic fractions and spinasterol was evaluated against RAW 264.7, M12.C3.F6, PC-3, LS-180, A549 and HeLa cancer cell lines by the standardized method MTT for determinate the antiproliferative activity. Methanolic extract of stem shown the better antiproliferative activity against the murine macrophage cancer cell line RAW 264.7. n-Hexane chemical fraction shown antiproliferative activity against human alveolar cancer cell line A549 and RAW 264.7. Was isolated and characterized a compound by NMR 1H and 13C, revealing the presence of sterol spinasterol. Spinasterol shown to have antiproliferative activity against cervical cancer cell line HeLa and RAW 264.7, indicating that spinasterol can be a responsible compound of antiproliferative activity found in the methanolic extract of Stegnosperma halimifolium.
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Shaik MR, Albalawi GH, Khan ST, Khan M, Adil SF, Kuniyil M, Al-Warthan A, Siddiqui MRH, Alkhathlan HZ, Khan M. "Miswak" Based Green Synthesis of Silver Nanoparticles: Evaluation and Comparison of Their Microbicidal Activities with the Chemical Synthesis. Molecules 2016; 21:molecules21111478. [PMID: 27827968 PMCID: PMC6274424 DOI: 10.3390/molecules21111478] [Citation(s) in RCA: 32] [Impact Index Per Article: 3.6] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 08/25/2016] [Revised: 10/24/2016] [Accepted: 10/31/2016] [Indexed: 11/16/2022] Open
Abstract
Microbicidal potential of silver nanoparticles (Ag-NPs) can be drastically improved by improving their solubility or wettability in the aqueous medium. In the present study, we report the synthesis of both green and chemical synthesis of Ag-NPs, and evaluate the effect of the dispersion qualities of as-prepared Ag-NPs from both methods on their antimicrobial activities. The green synthesis of Ag-NPs is carried out by using an aqueous solution of readily available Salvadora persica L. root extract (RE) as a bioreductant. The formation of highly crystalline Ag-NPs was established by various analytical and microscopic techniques. The rich phenolic contents of S. persica L. RE (Miswak) not only promoted the reduction and formation of NPs but they also facilitated the stabilization of the Ag-NPs, which was established by Fourier transform infrared spectroscopy (FT-IR) analysis. Furthermore, the influence of the volume of the RE on the size and the dispersion qualities of the NPs was also evaluated. It was revealed that with increasing the volume of RE the size of the NPs was deteriorated, whereas at lower concentrations of RE smaller size and less aggregated NPs were obtained. During this study, the antimicrobial activities of both chemically and green synthesized Ag-NPs, along with the aqueous RE of S. persica L., were evaluated against various microorganisms. It was observed that the green synthesized Ag-NPs exhibit comparable or slightly higher antibacterial activities than the chemically obtained Ag-NPs.
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Affiliation(s)
- Mohammed Rafi Shaik
- Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
| | - Ghadeer H Albalawi
- Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
- Faculty of Science, University of Tabuk, P.O. Box 741, Tabuk 71491, Saudi Arabia.
| | - Shams Tabrez Khan
- Department of Zoology, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
| | - Merajuddin Khan
- Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
| | - Syed Farooq Adil
- Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
| | - Mufsir Kuniyil
- Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
| | - Abdulrahman Al-Warthan
- Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
| | - Mohammed Rafiq H Siddiqui
- Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
| | - Hamad Z Alkhathlan
- Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
| | - Mujeeb Khan
- Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
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