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2
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Synthesis and antibacterial activity of racemic paecilocin A and its derivatives against methicillin-sensitive and -resistant Staphylococcus aureus. Tetrahedron Lett 2021. [DOI: 10.1016/j.tetlet.2021.152888] [Citation(s) in RCA: 2] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/30/2023]
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3
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Qin Y, Liu X, Lin J, Huang J, Jiang X, Mo T, Xu Z, Li J, Yang R. Two new phthalide derivatives from the endophytic fungus Penicillium vulpinum isolated from Sophora tonkinensis. Nat Prod Res 2019; 35:421-427. [PMID: 31274005 DOI: 10.1080/14786419.2019.1636237] [Citation(s) in RCA: 8] [Impact Index Per Article: 1.3] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/03/2023]
Abstract
Two new phthalide derivatives, (-)-3-carboxypropyl-7-hydroxyphthalide (1) and (-)-3-carboxypropyl-7-hydroxyphthalide methyl ester (2), were isolated from the endophytic fungus Penicillium vulpinum isolated from the Chinese medicinal plant Sophora tonkinensis. Their structures were elucidated using spectroscopic methods, mainly on 1D and 2D NMR. Compound 1 exhibited medium antibacterial activities against Bacillus subtilis, Shigella dysenteriae and Enterobacter areogenes with MIC values of 12.5-25 μg/mL, and 2 showed a medium inhibition to E. areogenes with MIC value of 12.5 μg/mL.
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Affiliation(s)
- Yuyue Qin
- State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, P. R. China
| | - Xiaobo Liu
- State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, P. R. China
| | - Jing Lin
- State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, P. R. China
| | - Jingying Huang
- State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, P. R. China
| | - Xiaofei Jiang
- State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, P. R. China
| | - Tuxiang Mo
- State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, P. R. China
| | - Zhaolong Xu
- State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, P. R. China
| | - Jun Li
- State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, P. R. China
| | - Ruiyun Yang
- State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, P. R. China
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Endophytic Fungi from Terminalia Species: A Comprehensive Review. J Fungi (Basel) 2019; 5:jof5020043. [PMID: 31137730 PMCID: PMC6616413 DOI: 10.3390/jof5020043] [Citation(s) in RCA: 27] [Impact Index Per Article: 4.5] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 04/22/2019] [Revised: 05/21/2019] [Accepted: 05/23/2019] [Indexed: 12/21/2022] Open
Abstract
Endophytic fungi have proven their usefulness for drug discovery, as suggested by the structural complexity and chemical diversity of their secondary metabolites. The diversity and biological activities of endophytic fungi from the Terminalia species have been reported. Therefore, we set out to discuss the influence of seasons, locations, and even the plant species on the diversity of endophytic fungi, as well as their biological activities and secondary metabolites isolated from potent strains. Our investigation reveals that among the 200-250 Terminalia species reported, only thirteen species have been studied so far for their endophytic fungi content. Overall, more than 47 fungi genera have been reported from the Terminalia species, and metabolites produced by some of these fungi exhibited diverse biological activities including antimicrobial, antioxidant, antimalarial, anti-inflammatory, anti-hypercholesterolemic, anticancer, and biocontrol varieties. Moreover, more than 40 compounds with eighteen newly described secondary metabolites were reported; among these, metabolites are the well-known anticancer drugs, a group that includes taxol, antioxidant compounds, isopestacin, and pestacin. This summary of data illustrates the considerable diversity and biological potential of fungal endophytes of the Terminalia species and gives insight into important findings while paving the way for future investigations.
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5
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Cabrera JM, Tauber J, Krische MJ. Enantioselective Iridium-Catalyzed Phthalide Formation through Internal Redox Allylation of Phthalaldehydes. Angew Chem Int Ed Engl 2018; 57:1390-1393. [PMID: 29240280 DOI: 10.1002/anie.201712015] [Citation(s) in RCA: 22] [Impact Index Per Article: 3.1] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/22/2017] [Indexed: 12/28/2022]
Abstract
An inside job: Enantioselective phthalide synthesis was achieved through internal redox allylation of o-phthalaldehydes. Oxidative esterification is balanced by reductive carbonyl addition to achieve an overall redox-neutral process. This method enabled formal syntheses of ent-spirolaxine methyl ether and CJ-12,954.
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Affiliation(s)
- James M Cabrera
- University of Texas at Austin, Department of Chemistry, 105 E 24th St. (A5300), Austin, TX, 78712-1167, USA
| | - Johannes Tauber
- University of Texas at Austin, Department of Chemistry, 105 E 24th St. (A5300), Austin, TX, 78712-1167, USA
| | - Michael J Krische
- University of Texas at Austin, Department of Chemistry, 105 E 24th St. (A5300), Austin, TX, 78712-1167, USA
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6
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Cabrera JM, Tauber J, Krische MJ. Enantioselective Iridium-Catalyzed Phthalide Formation through Internal Redox Allylation of Phthalaldehydes. Angew Chem Int Ed Engl 2018. [DOI: 10.1002/ange.201712015] [Citation(s) in RCA: 6] [Impact Index Per Article: 0.9] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/25/2023]
Affiliation(s)
- James M. Cabrera
- University of Texas at Austin; Department of Chemistry; 105 E 24th St. (A5300) Austin TX 78712-1167 USA
| | - Johannes Tauber
- University of Texas at Austin; Department of Chemistry; 105 E 24th St. (A5300) Austin TX 78712-1167 USA
| | - Michael J. Krische
- University of Texas at Austin; Department of Chemistry; 105 E 24th St. (A5300) Austin TX 78712-1167 USA
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7
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Gerasimchuk VV, Kucherenko AS, Fakhrutdinov AN, Medvedev MG, Nelyubina YV, Zlotin SG. Towards Sustainable Amino Acid Derived Organocatalysts for Asymmetric syn
-Aldol Reactions. European J Org Chem 2017. [DOI: 10.1002/ejoc.201700166] [Citation(s) in RCA: 6] [Impact Index Per Article: 0.8] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/29/2023]
Affiliation(s)
- Vasiliy V. Gerasimchuk
- Zelinsky Institute of Organic Chemistry; Russian Academy of Sciences; Leninsky Prospect 47 119991 Moscow Russia
| | - Alexandr S. Kucherenko
- Zelinsky Institute of Organic Chemistry; Russian Academy of Sciences; Leninsky Prospect 47 119991 Moscow Russia
| | - Artem N. Fakhrutdinov
- Zelinsky Institute of Organic Chemistry; Russian Academy of Sciences; Leninsky Prospect 47 119991 Moscow Russia
| | - Michael G. Medvedev
- Nesmeyanov Institute of Organoelement Compounds; Russian Academy of Sciences; Vavilov str., 28 119991 Moscow Russia
| | - Yulia V. Nelyubina
- Nesmeyanov Institute of Organoelement Compounds; Russian Academy of Sciences; Vavilov str., 28 119991 Moscow Russia
| | - Sergei G. Zlotin
- Zelinsky Institute of Organic Chemistry; Russian Academy of Sciences; Leninsky Prospect 47 119991 Moscow Russia
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8
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Making Use of Genomic Information to Explore the Biotechnological Potential of Medicinal Mushrooms. MEDICINAL AND AROMATIC PLANTS OF THE WORLD 2017. [DOI: 10.1007/978-981-10-5978-0_13] [Citation(s) in RCA: 4] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 12/15/2022]
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9
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Phthalides: Distribution in Nature, Chemical Reactivity, Synthesis, and Biological Activity. PROGRESS IN THE CHEMISTRY OF ORGANIC NATURAL PRODUCTS 104 2017; 104:127-246. [DOI: 10.1007/978-3-319-45618-8_2] [Citation(s) in RCA: 40] [Impact Index Per Article: 5.0] [Reference Citation Analysis] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 12/12/2022]
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10
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Vásquez-Ocmín P, Haddad M, Gadea A, Jullian V, Castillo D, Paloque L, Cerapio JP, Bourdy G, Sauvain M. A new phthalide derivative from Peperomia nivalis. Nat Prod Res 2016; 31:138-142. [DOI: 10.1080/14786419.2016.1219857] [Citation(s) in RCA: 2] [Impact Index Per Article: 0.2] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/21/2022]
Affiliation(s)
- Pedro Vásquez-Ocmín
- Laboratorios de Investigación y Desarrollo, Facultad de Ciencias y Filosofía, Universidad Peruana Cayetano Heredia, Lima, Peru
| | - Mohamed Haddad
- UMR 152 Pharma Dev, Université de Toulouse, IRD, UPS, Toulouse, France
| | - Alice Gadea
- Laboratorios de Investigación y Desarrollo, Facultad de Ciencias y Filosofía, Universidad Peruana Cayetano Heredia, Lima, Peru
| | - Valérie Jullian
- UMR 152 Pharma Dev, Université de Toulouse, IRD, UPS, Toulouse, France
| | - Denis Castillo
- Laboratorios de Investigación y Desarrollo, Facultad de Ciencias y Filosofía, Universidad Peruana Cayetano Heredia, Lima, Peru
| | - Lucie Paloque
- CNRS, LCC (Laboratoire de Chimie de Coordination) UPR8241, Toulouse, France
- Université de Toulouse, Toulouse, France
| | - Juan Pablo Cerapio
- Laboratorios de Investigación y Desarrollo, Facultad de Ciencias y Filosofía, Universidad Peruana Cayetano Heredia, Lima, Peru
| | - Geneviève Bourdy
- UMR 152 Pharma Dev, Université de Toulouse, IRD, UPS, Toulouse, France
| | - Michel Sauvain
- UMR 152 Pharma Dev, Université de Toulouse, IRD, UPS, Toulouse, France
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11
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Sun L, Wang S, Zhang S, Yu D, Qin Y, Huang H, Wang W, Zhan J. Identification of a type III polyketide synthase involved in the biosynthesis of spirolaxine. Appl Microbiol Biotechnol 2016; 100:7103-13. [DOI: 10.1007/s00253-016-7444-5] [Citation(s) in RCA: 9] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 01/22/2016] [Revised: 02/29/2016] [Accepted: 03/06/2016] [Indexed: 11/30/2022]
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12
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A formal total synthesis of anti - Helicobacter pylori agent (+)-spirolaxine methyl ether. Tetrahedron Lett 2016. [DOI: 10.1016/j.tetlet.2015.11.047] [Citation(s) in RCA: 4] [Impact Index Per Article: 0.4] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/22/2022]
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13
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Yazbek PB, Trindade AB, Chin CM, Dos Santos JL. Challenges to the Treatment and New Perspectives for the Eradication of Helicobacter pylori. Dig Dis Sci 2015; 60:2901-12. [PMID: 25999247 DOI: 10.1007/s10620-015-3712-y] [Citation(s) in RCA: 16] [Impact Index Per Article: 1.6] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Submit a Manuscript] [Subscribe] [Scholar Register] [Received: 02/05/2015] [Accepted: 05/07/2015] [Indexed: 12/13/2022]
Abstract
Helicobacter pylori (H. pylori) is one of the leading causes of gastric diseases such as chronic gastritis, peptic ulcer, and gastric adenocarcinoma. The current treatment of H. pylori infection with antibiotics and proton pump inhibitors has several limitations, including poor adherence and intrinsic patient-related factors, drug resistance, and the absence of adequate treatments. This review summarizes the current therapeutic approaches to eradicating H. pylori, the difficulties associated with its treatment, and several new perspectives aimed at improving existing treatment strategies.
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Affiliation(s)
- Priscila Baptistella Yazbek
- School of Pharmaceutical Science, Drugs and Medicines Department, State University of São Paulo "Júlio de Mesquita Filho", Rodovia Araraquara Jaú Km, 01 s/n, Araraquara, SP, 14801-902, Brazil
| | - Ariane Biolcati Trindade
- School of Pharmaceutical Science, Drugs and Medicines Department, State University of São Paulo "Júlio de Mesquita Filho", Rodovia Araraquara Jaú Km, 01 s/n, Araraquara, SP, 14801-902, Brazil
| | - Chung Man Chin
- School of Pharmaceutical Science, Drugs and Medicines Department, State University of São Paulo "Júlio de Mesquita Filho", Rodovia Araraquara Jaú Km, 01 s/n, Araraquara, SP, 14801-902, Brazil
| | - Jean Leandro Dos Santos
- School of Pharmaceutical Science, Drugs and Medicines Department, State University of São Paulo "Júlio de Mesquita Filho", Rodovia Araraquara Jaú Km, 01 s/n, Araraquara, SP, 14801-902, Brazil.
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14
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Jiang X, Sakthivel S, Kulbitski K, Nisnevich G, Gandelman M. Efficient synthesis of secondary alkyl fluorides via Suzuki cross-coupling reaction of 1-halo-1-fluoroalkanes. J Am Chem Soc 2014; 136:9548-51. [PMID: 24958322 DOI: 10.1021/ja504089y] [Citation(s) in RCA: 88] [Impact Index Per Article: 8.0] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/29/2022]
Abstract
Organofluorine compounds have found extensive applications in various areas of science. Consequently, the development of new efficient and selective methods for their synthesis is an important goal in organic chemistry. Here, we present the first Suzuki cross-coupling reaction which utilizes dihalo compounds for the preparation of secondary alkyl fluorides. Namely, an unprecedented use of simple 1-halo-1-fluoroalkanes as electrophiles in C(sp(3))-C(sp(3)) and C(sp(3))-C(sp(2)) cross-couplings allows for the formal site-selective incorporation of F-group in the alkyl chain with no adjacent activating functional groups. Highly effective approach to the electrophilic substrates, 1-halo-1-fluoroalkanes, via iododecarboxylation of the corresponding α-fluorocarboxylic acids is also presented. The conceptually new route to organofluorides was used for the facile preparation of biomedically valuable compounds. In addition, we demonstrated that an asymmetric version of the developed reaction for the stereoconvergent synthesis of chiral secondary alkyl fluorides is feasible.
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Affiliation(s)
- Xiaojian Jiang
- Schulich Faculty of Chemistry, Technion-Israel Institute of Technology , Technion City, Haifa 32000, Israel
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15
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Shashikumar ND, Krishnamurthy G, Bhojyanaik HS. A Facile Synthesis of Novel Cyclic Esters of γ-Keto Acid Derivatives by Heck Coupling Reaction. J Heterocycl Chem 2014. [DOI: 10.1002/jhet.1898] [Citation(s) in RCA: 3] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/10/2022]
Affiliation(s)
| | - G. Krishnamurthy
- Department of Chemistry; Sahyadri Science College(Autonomous); Shimoga 577203 Karnataka India
| | - Halehatti S. Bhojyanaik
- Department of PG Studies and Research in Industrial Chemistry, School of Chemical Sciences; Kuvempu University; Shankaraghatta 577 451 Shimoga Karnataka India
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16
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Ayala G, Escobedo-Hinojosa WI, Cruz-Herrera CFDL, Romero I. Exploring alternative treatments for Helicobacter pylori infection. World J Gastroenterol 2014; 20:1450-1469. [PMID: 24587621 PMCID: PMC3925854 DOI: 10.3748/wjg.v20.i6.1450] [Citation(s) in RCA: 94] [Impact Index Per Article: 8.5] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Download PDF] [Journal Information] [Submit a Manuscript] [Subscribe] [Scholar Register] [Received: 10/10/2013] [Revised: 12/21/2013] [Accepted: 01/05/2014] [Indexed: 02/06/2023] Open
Abstract
Helicobacter pylori (H. pylori) is a successful pathogen that can persist in the stomach of an infected person for their entire life. It provokes chronic gastric inflammation that leads to the development of serious gastric diseases such as peptic ulcers, gastric cancer and Mucosa associated lymphoid tissue lymphoma. It is known that these ailments can be avoided if the infection by the bacteria can be prevented or eradicated. Currently, numerous antibiotic-based therapies are available. However, these therapies have several inherent problems, including the appearance of resistance to the antibiotics used and associated adverse effects, the risk of re-infection and the high cost of antibiotic therapy. The delay in developing a vaccine to prevent or eradicate the infection has furthered research into new therapeutic approaches. This review summarises the most relevant recent studies on vaccine development and new treatments using natural resources such as plants, probiotics and nutraceuticals. In addition, novel alternatives based on microorganisms, peptides, polysaccharides, and intragastric violet light irradiation are presented. Alternative therapies have not been effective in eradicating the bacteria but have been shown to maintain low bacterial levels. Nevertheless, some of them are useful in preventing the adverse effects of antibiotics, modulating the immune response, gastroprotection, and the general promotion of health. Therefore, those agents can be used as adjuvants of allopathic anti-H. pylori eradication therapy.
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17
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Three new resorcylic acid derivatives from Sporotrichum laxum. Bioorg Med Chem Lett 2013; 23:5806-9. [PMID: 24070784 DOI: 10.1016/j.bmcl.2013.08.109] [Citation(s) in RCA: 8] [Impact Index Per Article: 0.7] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 07/28/2013] [Revised: 08/27/2013] [Accepted: 08/29/2013] [Indexed: 01/18/2023]
Abstract
Sporotrichum laxum ATCC 15155 is the producing strain of the potent anti-Helicobacter pylori natural product spirolaxine (1). Investigation of the secondary metabolites in this fungus led to the isolation of five phthalides (1, 2, 3, 6 and 9) and five resorcylic acid derivatives (4, 5, 7, 8 and 10), among which 5, 7 and 8 are new compounds. The structures were elucidated by spectroscopic analyses, and the absolute configurations of 7 and 8 were determined by Mosher's method. Addition of soy flour into the potato dextrose agar has led to the increased production of 4-10. A biosynthetic pathway consisting of a highly reducing polyketide synthase (PKS), a nonreducing PKS and a series of tailoring enzymes was proposed to produce these fungal natural products. The resorcylic acid derivatives are proposed to result from early hydrolysis of the polyketide chain or incorporation of a longer fatty acyl starter unit.
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18
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Biotransformation of spirolaxine by Absidia cuneospora and Trametes hirsuta: Formation of β-glycosyl and β-xylosyl derivatives. ACTA ACUST UNITED AC 2012. [DOI: 10.1016/j.molcatb.2012.06.006] [Citation(s) in RCA: 3] [Impact Index Per Article: 0.2] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/20/2022]
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19
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Dimitrov I, Furkert DP, Fraser JD, Radcliff FJ, Finch O, Brimble MA. Synthesis and anti-Helicobacter pylori activity of analogues of spirolaxine methyl ether. MEDCHEMCOMM 2012. [DOI: 10.1039/c2md00314g] [Citation(s) in RCA: 8] [Impact Index Per Article: 0.6] [Reference Citation Analysis] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 12/17/2022]
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20
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Yadav JS, Sreenivas M, Srinivas Reddy A, Subba Reddy BV. A Practical Total Synthesis of (+)-Spirolaxine Methyl Ether. J Org Chem 2010; 75:8307-10. [DOI: 10.1021/jo1016647] [Citation(s) in RCA: 18] [Impact Index Per Article: 1.2] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/28/2022]
Affiliation(s)
- J. S. Yadav
- Division of Organic Chemistry, Discovery Laboratory, Indian Institute of Chemical Technology, Hyderabad, India
| | - M. Sreenivas
- Division of Organic Chemistry, Discovery Laboratory, Indian Institute of Chemical Technology, Hyderabad, India
| | - A. Srinivas Reddy
- Division of Organic Chemistry, Discovery Laboratory, Indian Institute of Chemical Technology, Hyderabad, India
| | - B. V. Subba Reddy
- Division of Organic Chemistry, Discovery Laboratory, Indian Institute of Chemical Technology, Hyderabad, India
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Singh M, Argade NP. Chemoselective Coupling Reactions of 5,7-Dimethoxyphthalide with the Remotely Functionalized Alkyl Iodides: Facile Racemic Synthesis of Helicobacter pylori Antibiotics. J Org Chem 2010; 75:3121-4. [DOI: 10.1021/jo100168f] [Citation(s) in RCA: 17] [Impact Index Per Article: 1.1] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/30/2022]
Affiliation(s)
- Mandeep Singh
- Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India
| | - Narshinha P. Argade
- Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India
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22
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Zhou Y, Taylor B, Smith TJ, Liu ZP, Clench M, Davies NW, Rainsford KD. A novel compound from celery seed with a bactericidal effect against Helicobacter pylori. J Pharm Pharmacol 2010. [DOI: 10.1211/jpp.61.08.0011] [Citation(s) in RCA: 9] [Impact Index Per Article: 0.6] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/17/2022]
Abstract
Abstract
Objectives
The aim was to purify and characterise an antimicrobial component from celery (Apium graveolens) seeds, which have been used for centuries as a herbal medicine with reported antibacterial effects.
Methods
A crude alcoholic extract of celery seeds was fractionated by organic solvent extractions, column chromatography and HPLC. Fractions were assayed for antimicrobial activity against the gastric pathogen Helicobacter pylori and other bacteria. The purified antibacterial component was characterised via MS and NMR. Preliminary investigation of its mechanism of action included morphological studies, incorporation of macromolecular precursors, membrane integrity and two-dimensional protein electrophoresis.
Key findings
The purified component, termed ‘compound with anti-Helicobacter activity’ (CAH), had potent bactericidal effects against H. pylori; the minimum inhibitory concentration and minimum bactericidal concentration were 3.15 μg/ml and 6.25–12.5 μg/ml, respectively. CAH (Mr = 384.23; empirical formula C24H32O4) had specific inhibitory effects on H. pylori and was not active against Campylobacter jejuni or Escherichia coli. MS and NMR data were consistent with a dimeric phthalide structure. The results appeared to rule out mechanisms that operated solely by loss of membrane integrity or inhibition of protein or nucleic acid synthesis.
Conclusions
CAH may be suitable for further investigation as a potent agent for treating H. pylori infections.
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Affiliation(s)
- Yong Zhou
- Biomedical Research Centre, Sheffield Hallam University, Sheffield, UK
| | - Brian Taylor
- Department of Chemistry, University of Sheffield, Sheffield, UK
| | - Thomas J Smith
- Biomedical Research Centre, Sheffield Hallam University, Sheffield, UK
| | - Zhong-ping Liu
- Biomedical Research Centre, Sheffield Hallam University, Sheffield, UK
| | - Malcolm Clench
- Biomedical Research Centre, Sheffield Hallam University, Sheffield, UK
| | - Noel W Davies
- Central Science Laboratory, University of Tasmania, Hobart, Tasmania, Australia
| | - K D Rainsford
- Biomedical Research Centre, Sheffield Hallam University, Sheffield, UK
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23
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Zhang H, Zhang S, Liu L, Luo G, Duan W, Wang W. Synthesis of Chiral 3-Substituted Phthalides by a Sequential Organocatalytic Enantioselective Aldol-Lactonization Reaction. Three-Step Synthesis of (S)-(−)-3-Butylphthalide. J Org Chem 2009; 75:368-74. [DOI: 10.1021/jo902118x] [Citation(s) in RCA: 80] [Impact Index Per Article: 5.0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/28/2022]
Affiliation(s)
- Haoyi Zhang
- Department of Pharmaceutical Sciences, School of Pharmacy, East China University of Sciences & Technology, Shanghai 200237, China
| | - Shilei Zhang
- Department of Pharmaceutical Sciences, School of Pharmacy, East China University of Sciences & Technology, Shanghai 200237, China
- Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, New Mexico 87131-0001
| | - Lu Liu
- Department of Pharmaceutical Sciences, School of Pharmacy, East China University of Sciences & Technology, Shanghai 200237, China
| | - Guangshun Luo
- Department of Pharmaceutical Sciences, School of Pharmacy, East China University of Sciences & Technology, Shanghai 200237, China
| | - Wenhu Duan
- Department of Pharmaceutical Sciences, School of Pharmacy, East China University of Sciences & Technology, Shanghai 200237, China
- Shanghai Institute of Materia Medica, Shanghai Institutes of Biological Sciences, Chinese Academy of Sciences, Shanghai 201203, China
| | - Wei Wang
- Department of Pharmaceutical Sciences, School of Pharmacy, East China University of Sciences & Technology, Shanghai 200237, China
- Shanghai Institute of Materia Medica, Shanghai Institutes of Biological Sciences, Chinese Academy of Sciences, Shanghai 201203, China
- Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, New Mexico 87131-0001
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Raju BR, Saikia AK. Asymmetric synthesis of naturally occurring spiroketals. Molecules 2008; 13:1942-2038. [PMID: 18794795 PMCID: PMC6245485 DOI: 10.3390/molecules13081942] [Citation(s) in RCA: 62] [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: 07/21/2008] [Revised: 08/22/2008] [Accepted: 08/22/2008] [Indexed: 12/03/2022] Open
Abstract
Spiroketals are widely found as substructures of many naturally occurring compounds from diverse sources including plants, animals as well as microbes. Naturally occurring spiroketals are biologically active and most of them are chiral molecules. This article aims at reviewing the asymmetric synthesis of biologically active spiroketals for last 10 years (1998-2007).
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Affiliation(s)
| | - Anil K. Saikia
- Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India E-mail:
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Radcliff FJ, Fraser JD, Wilson ZE, Heapy AM, Robinson JE, Bryant CJ, Flowers CL, Brimble MA. Anti-Helicobacter pylori activity of derivatives of the phthalide-containing antibacterial agents spirolaxine methyl ether, CJ-12,954, CJ-13,013, CJ-13,102, CJ-13,104, CJ-13,108 and CJ-13,015. Bioorg Med Chem 2008; 16:6179-85. [DOI: 10.1016/j.bmc.2008.04.037] [Citation(s) in RCA: 19] [Impact Index Per Article: 1.1] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 02/13/2008] [Revised: 04/12/2008] [Accepted: 04/16/2008] [Indexed: 10/22/2022]
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26
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Ding G, Liu S, Guo L, Zhou Y, Che Y. Antifungal metabolites from the plant endophytic fungus Pestalotiopsis foedan. JOURNAL OF NATURAL PRODUCTS 2008; 71:615-618. [PMID: 18288805 DOI: 10.1021/np070590f] [Citation(s) in RCA: 87] [Impact Index Per Article: 5.1] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 05/25/2023]
Abstract
Pestafolide A ( 1), a new reduced spiro azaphilone derivative, and pestaphthalides A ( 2) and B ( 3), two new isobenzofuranones, have been isolated form solid cultures of an isolate of Pestalotiopsis foedan. The structures of these compounds were determined mainly by analysis of their NMR spectroscopic data. The relative configuration of 1- 3 was assigned by analysis of (1)H NMR J-values and NOESY data, and the absolute configuration was determined by application of the CD excitation chirality and modified Mosher method. Compounds 1- 3 showed modest antifungal activity.
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Affiliation(s)
- Gang Ding
- Key Laboratory of Systematic Mycology and Lichenology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100080, China
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Nasini G, Bava A, Fronza G, Giannini G. Microbial Transformation of Spirolaxine, a Bioactive Undecaketide Fungal Metabolite from the BasidiomyceteSporotrichum laxum. Chem Biodivers 2007; 4:2772-9. [DOI: 10.1002/cbdv.200790226] [Citation(s) in RCA: 4] [Impact Index Per Article: 0.2] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/07/2022]
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Trost B, Weiss A. An Alkyne Strategy for the Asymmetric Synthesis of Natural Products: Application to (+)-Spirolaxine Methyl Ether. Angew Chem Int Ed Engl 2007. [DOI: 10.1002/ange.200702637] [Citation(s) in RCA: 19] [Impact Index Per Article: 1.1] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/10/2022]
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Trost BM, Weiss AH. An Alkyne Strategy for the Asymmetric Synthesis of Natural Products: Application to (+)-Spirolaxine Methyl Ether. Angew Chem Int Ed Engl 2007; 46:7664-6. [PMID: 17722127 DOI: 10.1002/anie.200702637] [Citation(s) in RCA: 85] [Impact Index Per Article: 4.7] [Reference Citation Analysis] [MESH Headings] [Grants] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/09/2022]
Affiliation(s)
- Barry M Trost
- Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA.
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Wilson ZE, Heapy AM, Brimble MA. Synthesis of indole analogues of the anti-Helicobacter pylori compounds CJ-13,015, CJ-13,102, CJ-13,104 and CJ-13,108. Tetrahedron 2007. [DOI: 10.1016/j.tet.2007.04.067] [Citation(s) in RCA: 10] [Impact Index Per Article: 0.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/16/2022]
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Robinson JE, Brimble MA. Synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine methyl ether and the unnatural (2″S)-diastereomer. Org Biomol Chem 2007; 5:2572-82. [DOI: 10.1039/b708265g] [Citation(s) in RCA: 23] [Impact Index Per Article: 1.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022]
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32
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Brimble MA, Bryant CJ. Synthesis and assignment of the absolute configuration of the anti-Helicobacter pylori agents CJ-12,954 and CJ-13,014. Org Biomol Chem 2007; 5:2858-66. [PMID: 17700855 DOI: 10.1039/b709932k] [Citation(s) in RCA: 19] [Impact Index Per Article: 1.1] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022]
Abstract
The synthesis of the spiroacetal-containing anti-Helicobacter pylori agents (3S,2''S,5''S,7''S)- (ent-CJ-12,954) and (3S,2''S,5''R,7''S)- (ent-CJ-13,014) has been carried out based on the convergent union of a 1:1 mixture of heterocycle-activated spiroacetal sulfones and with (3S)-phthalide aldehyde . The synthesis of the (3R)-diastereomers (3R,2''S,5''S,7''S)- and (3R,2''S,5''R,7''S)- was also undertaken in a similar manner by union of (3R)-phthalide aldehyde with a 1:1 mixture of spiroacetal sulfones and . Comparison of the (1)H and (13)C NMR data, optical rotations and HPLC retention times of the synthetic compounds (3S,2''S,5''S,7''S)- and (3S,2''S,5''R,7''S)- and the (3R)-diastereomers (3R,2''S,5''S,7''S)- and (3R,2''S,5''R,7''S)-, with the naturally occurring compounds, established that the synthetic isomers and were in fact enantiomeric to the natural products CJ-12,954 and CJ-13,014. The (2S,8S)-stereochemistry in protected dihydroxyketone , the precursor to the mixture of spiroacetal sulfones and was established via union of readily available (S)-acetylene with aldehyde in which the (4S)-stereochemistry was established via asymmetric allylation. Deprotection and cyclization of protected dihydroxyketone afforded an inseparable 1:1 mixture of spiroacetal alcohols and that were converted into a 1:1 inseparable mixture of spiroacetal sulfones and . Phthalide-aldehyde was prepared via intramolecular acylation of bromocarbamate in which the (3S)-stereochemistry was established via asymmetric CBS reduction of ketone .
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Affiliation(s)
- Margaret A Brimble
- Department of Chemistry, University of Auckland, 23 Symonds St., Auckland, New Zealand.
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33
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Bava A, Dallavalle S, Fronza G, Nasini G, Vajna de Pava O. Absolute configuration of sporotricale and structure of 6-hydroxysporotricale. JOURNAL OF NATURAL PRODUCTS 2006; 69:1793-5. [PMID: 17190462 DOI: 10.1021/np060212v] [Citation(s) in RCA: 6] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 05/13/2023]
Abstract
The absolute configuration of the two stereocenters of (+)-sporotricale (2a), a bioactive phthalide secondary metabolite, was determined through circular dichroism and by applying Mosher's method. The structure of 6-hydroxysporotricale (2c), isolated from cultures in vitro of Sporotrichum laxum, was also elucidated.
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Affiliation(s)
- Adriana Bava
- Dipartimento di Chimica, Materiali ed Ingegneria Chimica "Giulio Natta" del Politecnico, CNR-Istituto di Chimica del Riconoscimento Molecolare, Sezione Quilico, via Mancinelli 7, 20131 Milan, Italy
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Nannei R, Dallavalle S, Merlini L, Bava A, Nasini G. Synthesis of (+)-Spirolaxine Methyl Ether. J Org Chem 2006; 71:6277-80. [PMID: 16872220 DOI: 10.1021/jo060839i] [Citation(s) in RCA: 38] [Impact Index Per Article: 2.0] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/29/2022]
Abstract
A short and efficient synthesis of (+)-spirolaxine methyl ether, a metabolite of the fungus Sporotrichum laxum with inhibitory activity against Helicobacter pylori, is described. The synthesis has been carried out by a Prins cyclization, to obtain the [6,5]-spiroketal system, and a Wadsworth-Emmons condensation, applied for the installation of the polymethylene chain on the phthalide moiety.
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Affiliation(s)
- Raffaella Nannei
- Dipartimento di Scienze Molecolari Agroalimentari, Università di Milano, Via Celoria 2, 20133 Milano, Italy
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Brimble MA, Bryant CJ. Synthesis of the spiroacetal-containing anti-Helicobacter pylori agents CJ-12,954 and CJ-13,014. Chem Commun (Camb) 2006:4506-8. [PMID: 17283800 DOI: 10.1039/b612757f] [Citation(s) in RCA: 21] [Impact Index Per Article: 1.1] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022]
Abstract
The first synthesis of the spiroacetal-containing anti-Helicobacter pylori agents ent-CJ-12,954 and ent-CJ-13,014 is reported based on the union of a heterocycle-activated spiroacetal-containing sulfone fragment with a phthalide-containing aldehyde fragment; comparison of the 1H and 13C NMR data, optical rotations and HPLC retention times of the synthetic compounds (3S,2"S,5"S,7"S)-(1a) and (3S,2"S,5"R,7"S)-(2a) and the (3R)-diastereomers (3R,2"S,5"S,7"S)-(1b) and (3R,2"S,5"R,7"S)- (2b) with the naturally occurring compounds established that the synthetic isomers (1a) and (2a) were in fact enantiomeric to the natural products CJ-12,954 and CJ-13,014.
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Affiliation(s)
- Margaret A Brimble
- Department of Chemistry, The University of Auckland, 23 Symonds St., Auckland, New Zealand.
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Brimble MA, Flowers CL, Hutchinson JK, Robinson JE, Sidford M. Synthesis of the phthalide-containing anti-Helicobacter pylori agents CJ-13,015, CJ-13,102, CJ-13,103, CJ-13,104 and CJ-13,108. Tetrahedron 2005. [DOI: 10.1016/j.tet.2005.08.027] [Citation(s) in RCA: 12] [Impact Index Per Article: 0.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/25/2022]
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37
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Bava A, Clericuzio M, Giannini G, Malpezzi L, Valdo Meille S, Nasini G. Absolute Configuration of the Fungal Metabolite Spirolaxine. European J Org Chem 2005. [DOI: 10.1002/ejoc.200400902] [Citation(s) in RCA: 20] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/09/2022]
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38
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Ziegert RE, Toräng J, Knepper K, Bräse S. The Recent Impact of Solid-Phase Synthesis on Medicinally Relevant Benzoannelated Oxygen Heterocycles. ACTA ACUST UNITED AC 2005; 7:147-69. [PMID: 15762741 DOI: 10.1021/cc049879v] [Citation(s) in RCA: 101] [Impact Index Per Article: 5.1] [Reference Citation Analysis] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/30/2022]
Affiliation(s)
- Robert E Ziegert
- Kekulé-Institut für Organische Chemie und Biochemie der Rheinischen Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, D-53121 Bonn, Germany
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Knepper K, Ziegert RE, Bräse S. Solid-phase synthesis of isoindolinones and naturally-occurring benzobutyrolactones (phthalides) using a cyclative-cleavage approach. Tetrahedron 2004. [DOI: 10.1016/j.tet.2004.05.111] [Citation(s) in RCA: 76] [Impact Index Per Article: 3.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/29/2022]
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40
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Mondal M, Argade NP. Synthesis of a new microbial secondary metabolite: anti- Helicobacter pylori CJ-13,015. Tetrahedron Lett 2004. [DOI: 10.1016/j.tetlet.2004.05.086] [Citation(s) in RCA: 13] [Impact Index Per Article: 0.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/29/2022]
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41
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Strobel G, Ford E, Worapong J, Harper JK, Arif AM, Grant DM, Fung PCW, Ming Wah Chau R. Isopestacin, an isobenzofuranone from Pestalotiopsis microspora, possessing antifungal and antioxidant activities. PHYTOCHEMISTRY 2002; 60:179-183. [PMID: 12009322 DOI: 10.1016/s0031-9422(02)00062-6] [Citation(s) in RCA: 182] [Impact Index Per Article: 7.9] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 05/23/2023]
Abstract
Isopestacin is an isobenzofuranone obtained from the endophytic fungus Pestalotiopsis microspora. While a few other isobenzofuranones are known from natural sources, isopestacin is the only one having a substituted benzene ring attached at the C-3 position of the furanone ring. The compound was isolated from culture broths of the fungus and crystallized and its structure was determined by X-ray crystallography. Both proton and carbon NMR spectral assignments are also reported for isopestacin. This compound possesses antifungal activity and, as measured by electron spin resonance specroscopy, it also behaves as an antioxidant scavenging both superoxide and hydroxy free radicals.
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Affiliation(s)
- Gary Strobel
- Department of Plant Sciences, Montana State University, Bozeman, MT 59717, USA.
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42
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Ando R, Kawamura M, Chiba N. 3-(Arylacetylamino)-N-methylbenzamides: a novel class of selective anti-Helicobacter pylori agents. J Med Chem 2001; 44:4468-74. [PMID: 11728192 DOI: 10.1021/jm010307o] [Citation(s) in RCA: 12] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/28/2022]
Abstract
After chemical modification preceded by the random screening of our chemical library, a novel class of selective anti-Helicobacter pylori agents was generated. Consequently, the 3-(arylacetylamino)-N-methylbenzamides, which were quite easy to prepare, showed potent inhibitory activity against Helicobacter pylori but exhibited no inhibitory activity against other sorts of bacteria and fungi, e.g., Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa, Bacteroides fragilis, and Candida albicans. These compounds showed potent anti-H. pylori activity under acidic conditions, whereas amoxicillin and clarithromycin decreased activity. The 3-(3-arylpropionylamino)-N-methylbenzamides, 3-(aryloxyacetylamino)-N-methylbenzamides, and (3-methylcarbamoylphenyl)carbamic acid 1-arylmethyl esters also exhibited potent anti-H. pylori activity. Finally, we selected 7n (BAS-118) as a candidate compound for further evaluation.
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Affiliation(s)
- R Ando
- Research Laboratory, Pharmaceuticals Research Division, Mitsubishi Pharma Corporation, 1000 Kamoshida-cho, Aoba-ku, Yokohama 227-0033, Japan.
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43
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Yoshida Y, Barrett D, Azami H, Morinaga C, Matsumoto Y, Takasugi H. Discovery of a novel benzyloxyisoquinoline derivative with potent anti-Helicobacter pylori activity. Bioorg Med Chem Lett 1998; 8:1897-902. [PMID: 9873455 DOI: 10.1016/s0960-894x(98)00335-7] [Citation(s) in RCA: 3] [Impact Index Per Article: 0.1] [Reference Citation Analysis] [Abstract] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/18/2022]
Abstract
The synthesis and in vitro optimization of the anti-Helicobacter pylori activity of a novel series of benzyloxyisoquinoline derivatives discovered by a random screening process, are described. FR180102 (7f), having a 3-acetamido-2,6-dichlorobenzyl moiety, was found to have extremely potent activity against H. pylori and no effect against a series of common Gram-positive and Gram-negative bacteria.
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Affiliation(s)
- Y Yoshida
- Medicinal Chemistry Research Laboratories, Fujisawa Pharmaceutical Co. Ltd., Osaka, Japan
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