Self‐assembly of Renewable  Nano‐sized Triterpenoids

Abstract

Studies on plant metabolites have gained renewed interest in recent years because these can serve as renewable chemicals for the development of a sustainable society. Among various plant secondary metabolites, terpenoids constitute the major component and triterpenoids are the 30C subset of it. In recent years, triterpenoids have drawn the attention of scientific community due to many of its potential and realized applications in medicine, drug delivery, thermochromic materials, pollutant capture, catalysis, liquid crystals, etc. In this personal review, we have discussed our computational results carried out on sixty representative naturally occurring triterpenoids demonstrating that all the triterpenoids are renewable functional nano-entities. Study of the self-assembly of several triterpenoids such as betulin, betulinic acid, oleanolic acid, glycyrrhetinic acid and arjunolic acid and their derivatives in different liquids have also been discussed. Moreover, the utilization of the resulting supramolecular architectures such as vesicles, spheres, flowers and fibrillar networks of nano- to micrometer dimensions and gels have also been discussed in the perspective of green, renewable and nanos.

Self assembled arjunolic acid acts as a smart weapon against cancer through TNF- α mediated ROS generation

“…In this purposeto reduce the toxicity Plant products (secondary metabolites) are often considered as safe. Our study showed that the AA is a pentacyclictriterpinoids which was isolated from the bark of Terminaliaarjuna which wasself-assembled and successfully entered into the cancer cell due to self-assemblednano sized structure [33].…”

First in situ vesicular self-assembly of ‘binols’ generated by a two-component aerobic oxidation reaction

“…These studies have helped scientists to improve the understanding of the structure property relationships that resulted in such supramolecular structures in liquid medium. [1][2][3][4][5][6][7][8][9][10] Spontaneous self-assembly of molecules, yielding vesicles, is of special signicance due to its tremendous application in the areas of targeted drug delivery, medical implants, nanoscale reactors, tissue engineering, gene therapy, theranostics, enzyme entrapment, magnetic resonance imaging, etc. [11][12][13][14][15][16][17][18] Literature studies reveal that vesicular self-assemblies have been reported from a wide range of amphiphilic compounds.…”

“…[19][20][21][22][23][24][25][26][27][28][29] Though, the formation of nano-sized spherical assemblies and vesicles in water from long alkyl-chained compounds having different head groups are known, according to our knowledge, aerobic coupling of two components leading to the formation of vesicular self-assemblies and supramolecular nano-architectures in organic media is unprecedented. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] Binols, obtained by coupling reaction of two b-naphthol precursors, have found application in the design of asymmetric catalysts for a wide range of chemical transformations. [30][31][32][33][34][35][36] The demonstration of self-replication on non-enzymatic model systems in its minimal form require: (1) suitable complementary recognition sites in the template molecule to complex the precursor molecules by non-covalent interactions and (2) a suitable chemical reaction for the formation of a chemical bond.…”

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

“…In addition, the low molecular weight hydrogelators derived from the natural products are of particular interest because, most of these supramolecular building blocks are biocompatible which is essential for using it in biomedical science, drug‐delivery or personal care products . 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.…”

“…[20] 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. [21] Because of this structural uniqueness of these triterpenoid molecules, they can even selfassemble without any structural modification yielding diversified self-assembled structures like fibers, [22,23] vesicles, [24,25,26,27,28] flowers, [29,30] 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.…”