Crystal Structure of Tricolorin A: Molecular Rationale for the Biological Properties of Resin Glycosides Found in Some Mexican Herbal Remedies

Rencurosi, Anna; Mitchell, Edward P.; Cioci, Gianluca; Pérez, Serge; Pereda‐Miranda, Rogelio; Imberty, Anne

doi:10.1002/anie.200460327

Cited by 28 publications

(15 citation statements)

References 22 publications

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“…The obtained conformational behavior of ipomotaosides disaccharide units was further compared to previous crystallographic and molecular mechanics (MM3) data of tricolorin A, the only member of this class of oligosaccharides with a published crystal structure [7] for the α-(1→2) linkage. The two main minima are located in similar regions as clearly demonstrated for both works.…”

Section: Resultsmentioning

confidence: 99%

“…Future efforts to develop these compounds through rational design, however, are impaired by the lack of structural information on their complexation to COX. Although there are crystallized glycoconjugates described in the literature [7] due to the high flexibility of glycosidic linkages in carbohydrates [8,9] and acyl chains and the consequent high amount of conformers coexisting in solution, [8,10,11] it is unusual to obtain 3D models for glycoconjugates from crystallographic methods. On the other hand, NMR methods are the main choice for dealing with such flexible compounds, for example, if a reasonable amount of ROESY/NOESY contacts are obtained [8].…”

Section: Introductionmentioning

confidence: 99%

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Conformational Characterization of Ipomotaosides and Their Recognition by COX-1 and 2

et al. 2014

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Abstract:The aerial parts of Ipomoea batatas are described herein to produce four new resin glycosides, designated as ipomotaosides A, B, C, and D. Ipomotaoside A was found to present inhibitory activity on both cyclooxygenases. However, the conformational elucidation of these molecules may be difficult due to their high flexibility. In this context, the current work presents a conformational characterization of ipomotaosides A-D in aqueous and nonaqueous solvents. The employed protocol includes metadynamics evaluation and unrestrained molecular dynamics simulations (MD). The obtained data provided structural models for the ipomotaosides in good agreement with previous ROESY distances measured in pyridine. Accordingly, the most abundant conformation of ipomotaoside A in solution was employed in flexible docking studies, providing a structural basis for the compound's inhibition of COX enzymes. The so-obtained complex supports resin glycosides' role as original scaffolds for future studies, aiming at structural optimization and development of potential new anti-inflammatory agents.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Conformational Characterization of Ipomotaosides and Their Recognition by COX-1 and 2

et al. 2014

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“…[25,34] However, their mode of action is still not well understood. [35] It is also reported that variations in the peripheral oxygenation and acylation pattern alter the cytotoxicity of the compounds. [36] Structures of ipomoeassin A-F (77-82) are shown in Figure 6.…”

Section: Natural Products: Ipomoeassins A-fmentioning

confidence: 99%

Metathesis and Macrocycles with Embedded Carbohydrates

Jarikote

Murphy

2010

Eur J Org Chem

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Macrocycles containing embedded carbohydrates are found in nature. Tricholorin A and G, woodrosin, sophorolipid lactone, cycloviracin B1, glucolipsin A and ipomoeassins A–F are natural products with interesting biological properties. They have inspired synthesis of non‐natural macrocyclic structures which contain embedded carbohydrates. Glycophanes (hybrids of carbohydrates and cyclophanes) were prepared which show potential in host‐guest chemistry and which have been applied as rigid scaffolds for the synthesis of bivalent inhibitors of lectin binding to tumour cells. Macrocyclic neoglycoconjugates have also been prepared. These include macrocyclic neooligoaminodeoxysaccharides which bind to RNA regions containing either asymmetric internal loop or hairpin loop‐stem junctions, and vaccine candidates. Non‐natural macrolides having antibacterial and antifungal activity have been synthesised. Metathesis using Grubbs and Hoyveda‐Grubbs catalysts has been key to the successful generation of these compounds. Herein we review the recent application of metathesis to the synthesis of ipomoeassins A, B and F, glycophanes, neooligoaminodeoxysaccharides,macrolides and other macrocycles with embedded carbohydrates.

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“…Four independent molecules were found in each asymmetric unit (which contains 284 non-hydrogen atoms) in a highly hydrated unit cell (Fig. 4) [12]. …”

Section: Reviewmentioning

confidence: 99%

“…(e) Molecular structure of one, out of the four crystallographically independent molecules in the unit cell. (f) Molecular modelling of the insertion of tricolorin A within a fluid phospholipid bilayer [12]. …”

Section: Reviewmentioning

confidence: 99%

Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

Pérez

Sanctis²

2017

Beilstein J. Org. Chem.

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Synchrotron radiation is the most versatile way to explore biological materials in different states: monocrystalline, polycrystalline, solution, colloids and multiscale architectures. Steady improvements in instrumentation have made synchrotrons the most flexible intense X-ray source. The wide range of applications of synchrotron radiation is commensurate with the structural diversity and complexity of the molecules and macromolecules that form the collection of substrates investigated by glycoscience. The present review illustrates how synchrotron-based experiments have contributed to our understanding in the field of structural glycobiology. Structural characterization of protein–carbohydrate interactions of the families of most glycan-interacting proteins (including glycosyl transferases and hydrolases, lectins, antibodies and GAG-binding proteins) are presented. Examples concerned with glycolipids and colloids are also covered as well as some dealing with the structures and multiscale architectures of polysaccharides. Insights into the kinetics of catalytic events observed in the crystalline state are also presented as well as some aspects of structure determination of protein in solution.

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Crystal Structure of Tricolorin A: Molecular Rationale for the Biological Properties of Resin Glycosides Found in Some Mexican Herbal Remedies

Cited by 28 publications

References 22 publications

Conformational Characterization of Ipomotaosides and Their Recognition by COX-1 and 2

Conformational Characterization of Ipomotaosides and Their Recognition by COX-1 and 2

Metathesis and Macrocycles with Embedded Carbohydrates

Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

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