Plant metabolites being renewable in nature have tremendous significance for the development of a sustainable society. In this manuscript we show that, terpenoids having nanometric lengths, commonly having several functional groups and several centers of chirality, can be utilized as renewable Molecular Functional Nanos (MFNs). The terpenoids spontaneously self-assembled in liquids yielding different morphologies such as vesicles, tubes, flowers, petals and fibers of nano- to micro-meter dimensions and supramolecular gels. The self-assemblies were utilized for the entrapment and release of fluorophores including anticancer drug, pollutant capture, generation of hybrid materials and catalysis.

Maslinic acid, a naturally occurring dihydroxy triterpenoid having a 6-6-6-6-6 fused pentacyclic structure, is extractable from the fruits of olive (Olea europaea). As part of our ongoing investigations on the self-assembly of natural products, herein, we report the results of our detailed investigation on the self-assembly of maslinic acid in different liquids. The triterpenoid self-assembled in aqueous binary liquid mixtures yielding vesicles of nano to micrometer diameters. Detailed characterization of the self-assemblies was carried out by scanning electron microscopy, high-resolution transmission electron microscopy, atomic force microscopy, optical microscopy, Fourier-transform infrared spectroscopy, and low-angle X-ray diffraction studies. The vesicular self-assemblies were capable of entrapping fluorophores including the chemotherapeutic anticancer drug doxorubicin. Triton X-100-triggered release of the encapsulated drug was also demonstrated via rupture of vesicles.

(C 30 H 50 O 2 ) 1 is a nanosized oleanane-type fused 6-6-6-6-6 pentacyclic triterpeneoid extractable from the dried leaves of olive (Olea europia). One step reduction of oleanolic acid extracted from Lantana camara also yields the same compound. The triterpenoid has one secondary −OH group attached at C3 of the "A" ring and one primary −OH group at C28 present at the junction of the "D" and "E" rings. Here, we report the spontaneous self-assembly of erythrodiol in different neat organic liquids and aqueous-organic liquid mixtures. The nanosized dihydroxy triterpenoid having an oleanane-type lipophilic rigid skeleton self-assembled in liquids, yielding nanosized fibrils, microsized flowers, and grass-like architectures via formation of densely assembled fibrils and petals or 2D sheets. The microstructures of the self-assemblies have been characterized by different techniques like optical microscopy, electron microscopy, atomic force microscopy, FTIR, and wide angle X-ray diffraction studies. The porous self-assemblies having a large surface area obtained from 1 were capable of adsorbing toxic fluorophores like rhodamine-B, rhodamine-6G, methylene blue, and crystal violet (CV). Moreover, removal of the aforementioned toxic pigments has also been demonstrated from their aqueous solutions by using UV−visible spectrophotometry and epifluorescence microscopy.

Terpenoids are a large and structurally group of natural products containing multiple five carbon containing isoprene units. Previously we have reported that irrespective of their acyclic or alicyclic nature, all the triterpenoids containing 30C’s have nano-metric lengths. In the current studies, detailed computations have been carried out with 120 naturally occurring mono- (C10), sesqui- (C15), di- (C20), sester- (C25), sesqua- (C35) and tetra- (C40) terpenoids using Gaussian 09 software with Gauss view 07 and molecular mechanics calculation using Serena software. The heat of formation and the calculated molecular lengths obtained by the two methods were compared. Interestingly, monoterpenoid to tetraterpenoid all the terpenoids (except three monoterpenoid and one sesqui-terpenoid) have molecular lengths above one nanometer making them useful as nano-sized building blocks.

Binol derivatives, obtained by aerobic coupling of two 2-naphthol derivatives having H-bond donor–acceptor groups and appended alkyl chains, spontaneously self-assembled in situ yielding vesicular self-assemblies and gels.