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

doi:10.1002/ange.200460327

Cited by 6 publications

(9 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Intrinsic glycan flexibility limited the use of such strategies. However, recent works showed that short oligosaccharides can adopt stable structures in solution, influencing their binding. − ,, Moreover, especially in plants, many examples of macrocyclic tethered oligosaccharides (e.g., tricolorin and calonyctin A) with interesting biological activities were identified. , As a consequence, artificial constrained oligosaccharides gained popularity (Figure ). Preorganized glycans pay a lower flexibility-induced entropic cost upon binding, resulting in higher affinity constants.…”

Section: Toward Sugar Foldamersmentioning

confidence: 99%

“…[16][17][18][19]94,95 Moreover, especially in plants, many examples of macrocyclic tethered oligosaccharides (e.g., tricolorin and calonyctin A) with interesting biological activities were identified. 96,97 As a consequence, artificial constrained oligosaccharides gained popularity (Figure 10). Preorganized glycans pay a lower flexibility-induced entropic cost upon binding, resulting in higher affinity constants.…”

Section: Conformational Locksmentioning

confidence: 99%

See 1 more Smart Citation

Structural Studies Using Unnatural Oligosaccharides: Toward Sugar Foldamers

et al. 2019

View full text Add to dashboard Cite

Biopolymers, like DNA and proteins, fold in specific conformations in order to exert complex biological functions. Synthetic modifications are commonly used to alter those conformations and create engineered biomaterials. In stark contrast, the chemical complexity and dynamic nature of polysaccharides have hampered a detailed structural characterization and structure−function correlations are still incomplete. Many synthetic strategies have been developed to access complex unnatural oligosaccharides, capable of mimicking or even improving the properties of the natural counterpart. However, the structural features behind these results are often neglected. This perspective highlights the approaches adopted to develop unnatural glycans, with a particular focus on how the insertion of specific modifications results in more flexible or more constrained structures. Synthetic analogues of natural oligosaccharides could shine light on fundamental structural features. The combination of modern synthetic, computational, and analytical methods will result in novel carbohydrate based foldamers, with defined shape and aggregation behavior. Multiple applications in biology, material science, and nanotechnology can be envisioned.

show abstract

Section: Toward Sugar Foldamersmentioning

confidence: 99%

Section: Conformational Locksmentioning

confidence: 99%

Structural Studies Using Unnatural Oligosaccharides: Toward Sugar Foldamers

et al. 2019

View full text Add to dashboard Cite

show abstract

“…[8][9][10] Resin glycosides exhibit a broad spectrum of biological activities, ranging from laxative, purgative, haemolytic, antibacterial, antifungal or plant growth inhibitory properties to significant cytotoxicity. [1][2][3][4] However, the understanding for their mode of action is largely missing, [11] as are systematic studies into structure-activity relationships. The available information, however, suggests that these compounds offer ample opportunity for optimization of their bioactivity profiles.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis and Biological Evaluation of the Cytotoxic Resin Glycosides Ipomoeassin A–F and Analogues

Nagano

Pospíšil

Chollet

et al. 2009

Chemistry A European J

View full text Add to dashboard Cite

A multitasking C-silylation strategy using the readily available compound 26 as a surrogate for cinnamic acid represents the key design element of a total synthesis of all known members of the ipomoeassin family of resin glyosides. This protecting group maneuver allows the unsaturated acids decorating the glucose subunit of the targets to be attached at an early phase of the synthesis, prevents their participation in the ruthenium-catalyzed ring-closing metathesis (RCM) used to form the macrocyclic ring, and protects them against reduction during the hydrogenation of the resulting cycloalkene over Wilkinson's catalyst. As the C-silyl group can be concomitantly removed with the O-TBS substituent using tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) in acetonitrile, no separate protecting group manipulations were necessary in the final stages, thus contributing to a favorable overall "economy of steps". In addition to the naturally occurring ipomoeassins, a small set of synthetic analogues has also been prepared by "diverted total synthesis". The cytotoxicity of these compounds was assayed with two different cancer cell lines. The recorded data confirm previous findings that the acylation- and oxygenation pattern of these amphiphilic glycoconjugates is highly correlated with their biological activity profile. Ipomoeassin F turned out to be the most promising member of the series, showing IC(50) values in the low nanomolar range.

show abstract

“…22 This supports the hypothesis proposed by Pereda− Miranda and colleagues that some biological potential of the resin glycosides may rely on their pore-forming properties to provoke an imbalance in cellular homeostasis. 6,23 ■ EXPERIMENTAL SECTION General Experimental Procedures. Optical rotations were obtained on a JASCO P-1020 polarimeter.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Cytotoxic Resin Glycosides from Ipomoea aquatica and Their Effects on Intracellular Ca²⁺ Concentrations

Fan

et al. 2014

J. Nat. Prod.

View full text Add to dashboard Cite

Eleven new resin glycosides, aquaterins I-XI (1-11), were isolated from the whole plants of Ipomoea aquatica. The structures of 1-11 were elucidated by a combination of spectroscopic and chemical methods. They were found to be partially acylated tetra- or pentasaccharides derived from simonic acid B and operculinic acids A and C. The site of the aglycone macrolactonization was placed at C-2 or C-3 of the second saccharide moiety, while the two acylating residues could be located at C-2 (or C-3) of the second rhamnose unit and at C-4 (or C-3) on the third rhamnose moiety. All compounds were evaluated for cytotoxicity against a small panel of human cancer cell lines. Compound 4 exhibited the most potent activity against HepG2 cells with an IC50 value of 2.4 μM. Cell cycle analysis revealed 4 to inhibit the proliferation of HepG2 cells via G0/G1 arrest and apoptosis induction. In addition, compounds 1-4, 7, 9, and 10 were found to elevate Ca(2+) in HepG2 cells, which might be involved in the regulation of the cytotoxic activities observed.

show abstract

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

Cited by 6 publications

References 22 publications

Structural Studies Using Unnatural Oligosaccharides: Toward Sugar Foldamers

Structural Studies Using Unnatural Oligosaccharides: Toward Sugar Foldamers

Total Synthesis and Biological Evaluation of the Cytotoxic Resin Glycosides Ipomoeassin A–F and Analogues

Cytotoxic Resin Glycosides from Ipomoea aquatica and Their Effects on Intracellular Ca²⁺ Concentrations

Contact Info

Product

Resources

About

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

Cited by 6 publications

References 22 publications

Structural Studies Using Unnatural Oligosaccharides: Toward Sugar Foldamers

Structural Studies Using Unnatural Oligosaccharides: Toward Sugar Foldamers

Total Synthesis and Biological Evaluation of the Cytotoxic Resin Glycosides Ipomoeassin A–F and Analogues

Cytotoxic Resin Glycosides from Ipomoea aquatica and Their Effects on Intracellular Ca2+ Concentrations

Contact Info

Product

Resources

About

Cytotoxic Resin Glycosides from Ipomoea aquatica and Their Effects on Intracellular Ca²⁺ Concentrations