Self-assembly of a renewable nano-sized triterpenoid 18β-glycyrrhetinic acid

Bag, Braja Gopal; Majumdar, Rakhi

doi:10.1039/c2ra21051g

Cited by 78 publications

(64 citation statements)

References 36 publications

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“…1 They have attracted immense attention due to their relative low-toxicity and fascinating antivirus, anti-tumor, and anti-inflammatory properties. 3 The skeletons of triterpenoids are lined with readily accessible hydroxyl and carboxyl groups, which allows for the facile introduction of functional units to promote non-covalent interactions and engender supramolecular assemblies. 3 The skeletons of triterpenoids are lined with readily accessible hydroxyl and carboxyl groups, which allows for the facile introduction of functional units to promote non-covalent interactions and engender supramolecular assemblies.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular helical nanofibers assembled from a pyridinium-functionalized methyl glycyrrhetate amphiphile

Gao

Hao

et al. 2015

Nanoscale

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A glycyrrhetate-containing amphiphile, MGP (1-[2-(methyl glycyrrhetate)-2-oxoethyl]pyridinium bromide), has been synthesized, and found to assemble into supramolecular helical nanofibers in chloroform/aromatic solvents, which are primarily driven by π-π stacking, van der Waals forces, and hydrophobic interactions. During the assembly process, MGP stacked into J-aggregates resulting in the sequestration of the hydrophilic pyridinium cation within the interior with the concomitant projection of its hydrophobic skeleton on the outside surface. Ultimately, this protrusion generated a staggered angle due to the steric hindrance between stacked molecules. This staggered angle further led to molecular misalignments and the formation of helical fibrils, which could twist with each other to fabricate larger helical fibers. Consequently, a gel was formed by intertwining these nanofibers into three-dimensional networks. Using this strategy, we found that other triterpenoid-tailored pyridinium amphiphiles are also potential scaffolds for supramolecular helical structures. This work provides a facile approach for the fabrication of supramolecular macroscopic chiral nanostructures that originate from natural products.

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Section: Introductionmentioning

confidence: 99%

Supramolecular helical nanofibers assembled from a pyridinium-functionalized methyl glycyrrhetate amphiphile

Gao

Hao

et al. 2015

Nanoscale

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“…have been utilized for the synthesis of AuNPs. During our investigations on the utilization of triterpenoids (C30s) as renewable functional nanoentities [11][12][13][14], it occurred to us that the medicinally important leaf extract of Acacia nilotica, rich in polyphenolic compounds, can be utilized for the synthesis of AuNPs from HAuCl 4 . Herein, we report a very mild and environmentfriendly method for the synthesis of AuNPs from the leaf extract of A. nilotica at room temperature without any additional capping or stabilizing agents.…”

Section: Introductionmentioning

confidence: 99%

Acacia nilotica (Babool) leaf extract mediated size-controlled rapid synthesis of gold nanoparticles and study of its catalytic activity

Majumdar¹,

Bag

Maity³

2013

Int Nano Lett

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The leaf extract of Acacia nilotica (Babool) is rich in different types of plant secondary metabolites such as flavanoids, tannins, triterpenoids, saponines, etc. We have demonstrated the use of the leaf extract for the synthesis of gold nanoparticles in water at room temperature under very mild conditions. The synthesis of the gold nanoparticles was complete in several minutes, and no extra stabilizing or capping agents were necessary. The size of the nanoparticles could be controlled by varying the concentration of the leaf extract. The gold nanoparticles were characterized by HRTEM, surface plasmon resonance spectroscopy, and X-ray diffraction studies. The synthesized gold nanoparticles have been used as an efficient catalyst for the reduction of 4-nitrophenol to 4-aminophenol in water at room temperature.

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“…Among various supramolecular building blocks from natural resources, the pentacyclic triterpenoid molecules have gained a significant attention of the scientific community in recent years because these nano‐sized chiral triterpenoid molecules possess a rigid backbone along with different functional groups at different positions and orientations . Because of this structural uniqueness of these triterpenoid molecules, they can even self‐assemble without any structural modification yielding diversified self‐assembled structures like fibers,, vesicles,,,,, flowers,, etc. which have been exploited as drug delivery vehicle, dye removing agent, template for the synthesis of organic‐inorganic advanced hybrid material for using it as recyclable heterogeneous catalyst, etc.…”

Section: Introductionmentioning

confidence: 99%

Evolution of Vesicular Self‐Assemblies of the Salts of a Natural Triterpenoid Arjunolic Acid into Superstructured Ambidextrous Gels and Study of Their Entrapment Properties

Majumdar

Bag

2018

ChemistrySelect

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Generation of supramolecular hydrogel from biocompatible supramolecular building blocks has become an area of tremendous research investigation because of it's potential use in biomedical sciences, food industries, cosmetics, etc. In recent years, the biocompatible nano‐sized trieterpenoid molecules have gained significant attention of the scientific community as supramolecular building blocks because of its unique molecular structures. Herein, we report the hierarchical self‐assembly properties of sodium and potassium salts of a naturally ocurring triterpenoid arjunolic acid in water and aliphatic alcohols. An interesting evolution of vesicular self‐assemblies of the molecules at a lower gelator concentration to giant fibrillar assemblies at a higher gelator concentration affording stable gels were obseved. The vesicular self‐assemblies have been utilized for the entrapment and controlled release of various fluorophores including the anticancer drug doxorubicin at physiological pH.

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Self-assembly of a renewable nano-sized triterpenoid 18β-glycyrrhetinic acid

Cited by 78 publications

References 36 publications

Supramolecular helical nanofibers assembled from a pyridinium-functionalized methyl glycyrrhetate amphiphile

Supramolecular helical nanofibers assembled from a pyridinium-functionalized methyl glycyrrhetate amphiphile

Acacia nilotica (Babool) leaf extract mediated size-controlled rapid synthesis of gold nanoparticles and study of its catalytic activity

Evolution of Vesicular Self‐Assemblies of the Salts of a Natural Triterpenoid Arjunolic Acid into Superstructured Ambidextrous Gels and Study of Their Entrapment Properties

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