Ent-kaurane diterpenoids and glycosides: Isolation, properties, and chemical transformations

Synthesis of Macroheterocyclic Compounds with a Furan Bridge Possessing Structural Fragments of 1,2,3-Triazoles and Natural Diterpenoids

“…Glycyrrhetinic acidtweezer receptors with excellent selectivity and affinity for Hg 2+ ion, [11] and stable cyclic dimer based on oleanolic acid with remarkable binding ability to F -ion [7] were reported. In the series of macrocyclic diterpenoids from isosteviol [12,13] and steviol, [14] compounds with excellent antituberculosis activity were found. [14] Macrocyclic derivatives of diterpenoid paclitaxel exhibited cytotoxicity against pancreatic cell lines expressing multidrug-resistant genes.…”

Biological Template Based on ent-Kaurane Diterpenoid Glycosides for the Synthesis of Inorganic Porous Materials

“…In particular, the kauranes represent an important group of tetracyclic diterpenes and their structures are constituted by a perhydrophenantrene unit (a, b and c rings) fused with a cyclopentane unit (d ring) formed by a bridge of two carbons between C-8 and C-13 ( Figure 1) [2]. Several criteria are used for the nomenclature of the kaurane diterpenes, the most frequent being the inversion of the conventional description of stereochemistry when the name is preceded by the prefix "ent-" [1,[4][5][6].…”

“…Diterpenoids can be subdivided into acyclic (phytanes), bicyclic (labdanes, clerodanes), tricyclic (pimaranes, abietanes, cassanes, rosanes, vouacapanes, podocarpanes), tetracyclic (trachylobanes, kauranes, aphidicolanes, stemodanes, stemaranes, beyeranes, atisan macrocy-clicditerpernes (taxanes, cembranes, daphnanes, tiglianes, ingenanes) and mixed compounds, in accordance with the number and the cyclization patterns displayed by their skeletal [1,2]. Natural compounds of this class have been found in many plants, fungi, sea organisms and insects [1]. In particular, the kauranes represent an important group of tetracyclic diterpenes and their structures are constituted by a perhydrophenantrene unit (a, b and c rings) fused with a cyclopentane unit (d ring) formed by a bridge of two carbons between C-8 and C-13 ( Figure 1) [2].…”

“…Diterpenoids constitute a class of natural compounds among the richest in terms of chemical structure and highly diverse properties [1][2][3]. Diterpenoids can be subdivided into acyclic (phytanes), bicyclic (labdanes, clerodanes), tricyclic (pimaranes, abietanes, cassanes, rosanes, vouacapanes, podocarpanes), tetracyclic (trachylobanes, kauranes, aphidicolanes, stemodanes, stemaranes, beyeranes, atisan macrocy-clicditerpernes (taxanes, cembranes, daphnanes, tiglianes, ingenanes) and mixed compounds, in accordance with the number and the cyclization patterns displayed by their skeletal [1,2].…”

Synthesis and Anticancer Evaluation of Complex Unsaturated Isosteviol-Derived Triazole Conjugates

“…In particular, since the end of the 1990s, ent-beyrane diterpenoid isosteviol has attracted a great deal of attention from medicinal chemists as a native scaffold for organic chemistry and drug discovery [1][2][3]. With its unique rigid skeletal structure with six stereo centers, isosteviol derivatives have been shown to have numerous biological activities [4][5][6][7][8][9], particularly in the anticancer area [10][11][12][13][14][15].…”