Arjunolic acid: A promising new building block for nanochemistry

Bag, Braja Gopal; Maity, Gopal Chandra; Pramanik, Subhash R.

doi:10.1007/bf02704093

Cited by 17 publications

(9 citation statements)

References 8 publications

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“…Over the past decade, they have been widely reported for their prominent biological properties, such as antitumor, anti-inflammatory, antimicrobial, and hepatoprotective activities. − In addition to their therapeutic attributes, increasing attention has been directed toward their other distinctive features, including the rigid skeleton, abundant chiral centers, and multiple reactive groups. These features render triterpenoids as one of the ideal building blocks for creating supramolecular structures by self-assembly. − To date, Bag, − Mezzenga, and our group − have reported a number of supramolecular assemblies based on triterpenoids, especially glycyrrhetinic acid ( GA ), oleanolic acid ( OA ), and arjunolic acid ( AA ). Among them, diverse architectures (e.g., fibers, vesicles, flowers, helices, and spheres) have been achieved under various conditions.…”

Section: Introductionmentioning

confidence: 99%

Solvent-Directed Assembly of a Pyridinium-Tailored Methyl Oleanolate Amphiphile: Stepwise Growth of Microrods and Nanofibers

Gao

Hao

et al. 2016

Langmuir

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Although a few architectures have been fabricated by the self-assembly of natural triterpenoids, the precise control of shape and size is rarely studied. Herein, a methyl oleanolate-bearing amphiphile, 1-[2-(methyl oleanolate)-2-oxoethyl]pyridinium bromide (MOP), has been designed and its assembly behavior was investigated. It was found that the morphologies of MOP assemblies ranged from nanoparticles to rigid microrods and flexible nanofibers in chloroform/p-xylene and methanol/water, respectively. During the assembly process, the systematical variational solvophobic/solvophilic effect resulted in the formation of spherical nanoparticles with opposite dipoles and converse bilayer structures. Moreover, such opposite molecular orientations lead to the inversion of supramolecular chirality and distinct mechanical properties. The driving forces and packing patterns of MOP in each solvent system were clearly demonstrated by the combination of NMR, UV-vis, Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), theoretical computation, and contact angle experiments, which revealed the roles of triterpenoids and pyridinium cations in the assembly process. This work provides a facile strategy to control the supramolecular structures in triterpenoid-based assemblies by adjusting the solvent polarity and composition.

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Section: Introductionmentioning

confidence: 99%

Solvent-Directed Assembly of a Pyridinium-Tailored Methyl Oleanolate Amphiphile: Stepwise Growth of Microrods and Nanofibers

Gao

Hao

et al. 2016

Langmuir

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“…Functional triterpenes having a rigid lypophilic backbone offer a great opportunity for the construction of molecular receptors, supramolecular architectures, and functional nanomaterials. , We have recently reported the first example of a triterpene-based organogelator . Herein, we report the significance of electron donor−acceptor (EDA) interaction on the gelation of organic solvents by an anthrylidene derivative of the triterpenoid , arjunolic acid .…”

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confidence: 97%

Donor−Acceptor Interaction Promoted Gelation: Visual Observation of Color Change

2006

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An anthrylidene derivative of arjunolic acid could immobilize varieties of organic solvents at low concentrations in the presence of an electron-deficient guest. Gelation in the presence of picric acid in organic solvents could be observed visually with concomitant color change. Electron micrographs of the xerogels showed a fibrous structure having fibers of submicron diameters. [structure: see text].

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“…The increase of T gel with increase in gelator concentration (Fig. 1b) indicates stronger intermolecular interactions [12]. Ethanol-CH 2 Cl 2 (6:…”

Section: First Triterpene-based Organogelatormentioning

confidence: 96%

Arjunolic acid: A renewable template in supramolecular chemistry and nanoscience

Bag

Dinda

2007

Pure and Applied Chemistry

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Arjunolic acid, a triterpenoid, renewably resourced from Terminalia arjuna sawdust, has the potential of being used as a structural molecular framework in supramolecular chemistry and nanoscience. The nanosized chiral triterpenoid on derivatization could immobilize varieties of organic solvents at low concentrations. The low-molecular-mass organic compounds self-assembled in organic media to form fibrous network structures having fibers of nano- to micrometer diameters. A dual-component supramolecular gelation has been demonstrated, exhibiting interesting thermochromic property. An arjunolic acid-derived crown ether showed efficient binding to monovalent cations, including a primary ammonium ion paving the way for chiral recognition of amino acids.

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Arjunolic acid: A promising new building block for nanochemistry

Cited by 17 publications

References 8 publications

Solvent-Directed Assembly of a Pyridinium-Tailored Methyl Oleanolate Amphiphile: Stepwise Growth of Microrods and Nanofibers

Solvent-Directed Assembly of a Pyridinium-Tailored Methyl Oleanolate Amphiphile: Stepwise Growth of Microrods and Nanofibers

Donor−Acceptor Interaction Promoted Gelation: Visual Observation of Color Change

Arjunolic acid: A renewable template in supramolecular chemistry and nanoscience

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