Natural sesquiterpene quinone/quinols: chemistry, biological activity, and synthesis

Abstract

This review summarizes 196 reports related to 558 new sesquiterpene quinone/quinols spanning the years 2010–2021.

Pathogenesis of Alzheimer’s Disease and Diversity of 1,2,3-Triazole Scaffold in Drug Development: Design Strategies, Structural Insights, and Therapeutic Potential

“…Drimane core, a bicycle sesquiterpene, possesses a wide range of biological activities . There are a number of examples in the literature describing AChE inhibitory activity of the drimane nucleus. , QSAR studies described that for inhibition of AChE and BuChE, some important features must be present in the molecule, i.e., hydrophobic scaffold and electronegative substituents.…”

“…Structure−activity relationship described that substitution of dioxoisoindoline with four-carbon chain was most suitable for amyloid β inhibitory activity, while replacement of dioxoisoindoline with phenyl groups significantly decreased the activity. 117 In the continuation of previous work, Rastegari et al designed and synthesized a series of 1,2,3- 120 There are a number of examples in the literature describing AChE inhibitory activity of the drimane nucleus. 121,122 QSAR studies described that for inhibition of AChE and BuChE, some important features must be present in the molecule, i.e., hydrophobic scaffold and electronegative substituents.…”

Phytochemistry and Pharmacology of Sesquiterpenoids from Atractylodes DC. Genus Rhizomes

“…Sesquiterpenes are significant oily compositions with extensive dispersal in plants, currently gaining recognition due to their wide range of pharmacological effects, including antitumor, anti-inflammatory, antibacterial and antiviral, etc. [ 13 , 14 , 15 ]. According to the diverse skeletal structures of sesquiterpenes in Atractylodes DC., they can be divided into the following five categories: eudesmane-type (such as β -eudesmol, atractylon), guaiane-type (such as atractylmacrol A, atrchiterpene D), spirovetivane-type (such as hinesol, hinesolone), isopterocarpolone-type (such as 14-hydroxy-isopterocarpolone, Atractyloside I), and eremophilane-type [ 10 , 16 , 17 , 18 , 19 , 20 , 21 ].…”

Pseudoceranoids A–J, Sesquiterpene-Based Meroterpenoids with Cytotoxicity from the Sponge Pseudoceratina purpurea

“…Less common are members with a rearranged 4,9-friedodrimane-type framework, including bolinaquinone, 21-dehydroxybolinaquinone, dysidotronic acid, dysidenones A and B, dysidine, dysideamine, and neodactyloquinone . The structural diversity of marine sponge meroterpenoids was also reflected in the various polyketide fragments, presenting phenol or quinone/hydroquinone moieties, a few cyclopentanones, ,− or tetronic acid/lactone moieties. ,,,− More than 300 sesquiterpene-based meroterpenoids have been isolated from marine sponges, many of which show biological activities such as antiviral, antitumor, ,− anti-inflammatory, − and antiangiogenic activities, among others.…”

“…Merosesquiterpenes have been isolated mainly from Dysidea , Dactylospongia , and Spongia sponge species. As part of our ongoing investigations of the bioactive metabolites from Chinese marine invertebrates, a sample of Pseudoceratina purpurea was collected in the South China Sea.…”