Synthesis and anticancer evaluation of complex unsaturated isosteviol-derived triazole conjugates.

Background: For the last two decades, diterpenoid isosteviol and its derivatives have gained significant attention for novel chemical transformation in the drug discovery field.

Results: An efficient way towards the synthesis of structurally diverse isosteviol derivatives was described here employing unsaturated functionalities as attractive templates for further transformation such as epoxidation. These structurally diverse compounds exhibited promising cytotoxic activities on different types of cancer cell lines, leading to drug discovery derived from natural products for the treatment of cancer.

Design and synthesis of isosteviol triazole conjugates for cancer therapy.

One of the keys for successfully developing drugs against the broad spectrum of cancer cell types is structural diversity. In the current study, we focused on a family of isosteviol derivatives as potential novel antitumor agents. Isosteviol is a tetracyclic diterpenoid obtained by acid hydrolysis of steviol glycoside extracts isolated from abundant Stevia rebaudiana plants.

Supramolecular design of biocompatible nanocontainers based on amphiphilic derivatives of a natural compound isosteviol.

Two diterpenoid surfactants with ammonium head groups and bromide (S1) or tosylate (S2) counterions have been synthesized. Exploration of these biomimetic species made it possible to demonstrate that even minor structural changes beyond their chemical nature may dramatically affect their solution behavior. While their aggregation thresholds differ inconsiderably, morphological behavior and affinity to lipid bilayer are strongly dependent on the counterion nature.

Synthesis and antituberculosis activity of novel unfolded and macrocyclic derivatives of ent-kaurane steviol.

New derivatives of steviol 1, the aglycone of the glycosides of Stevia rebaudiana, including a novel class of semisynthetic diterpenoids, namely macrocyclic ent-kauranes were synthesized. These compounds possess antituberculosis activity inhibiting the in vitro growth of Mycobacterium Tuberculosis (H37R(V) strain) with MIC 5-20 μg/ml that is close to MIC 1 μg/ml demonstrated by antituberculosis drug isoniazid in control experiment. For the first time it was found that the change of ent-kaurane geometry (as in steviol 1) of tetracyclic diterpenoid skeleton to ent-beyerane one (as in isosteviol 2) influences on antituberculosis activity.