Pimarane diterpenes: Natural source, stereochemical configuration, and biological activity

Abstract

Plants and fungi are seemingly inexhaustible sources of interesting natural products with remarkable structural and biological diversity. One of the most important groups is the terpenes, ubiquitous natural products that are generated by 2 now well-established biosynthetic pathways: the older mevalonate and the more recently discovered 1-deoxyxylulose-5-phosphate. Among the diterpenes, the pimarane diterpenes are a very representative subgroup with several and interesting biological activities resulting from different functional group modifications. In this review, we outline the method of their structure determination, mainly spectroscopic results, their absolute configuration, and structure-activity relationships, were reported, as well as the mode of action for selected examples from plants, marine organisms, and fungi. The pimarane, isopimarane, and ent-pimarane diterpenes covered in this review have a wide range of biological activities including antimicrobial, antifungal, antiviral, phytotoxic, phytoalexin, cytotoxicity, and antispasmodic and relaxant effects.

Ponicidin as a promising anticancer agent: Its biological and biopharmaceutical profile along with a molecular docking study

“…To date, a number of potential diterpenoids and their synthetic derivatives have been recognized for their important biological activities. Numerous examples on diterpenoids can be found in the literature including cassane and norcassane diterpenes , rosemary diterpenes , phytol , and pimarane .…”

Bioactive Compounds Isolated from Marine-Derived Microbes in China: 2009–2018

“…They exhibited inhibitory activity against some marine phytoplankton species [99]. Pimarane diterpenes are a widely distributed class of terpenes that are produced by a wide variety of organisms, and marine-derived fungi are no exception [100]. In 2012, Sun et al reported the isolations of five new oxygenated pimarane diterpenes, named scopararanes C–G ( 286 – 290 ), from a marine sediment-derived fungus Eutypella scoparia FS26.…”

Sarcosenones A–C, highly oxygenated pimarane diterpenoids from an endolichenic fungus Sarcosomataceae sp.

“…Pimarane diterpenoids have been encountered as secondary metabolites of higher plants, fungi, and marine organisms. 1 This class of diterpenes can be derived from the original core by substitution, hydroxylation, acetylation, rearrangement, bromination, and ring expansion reactions. 2 Since the isolation of pimaric acid, the rst example of this class, in 1839, 3 pimarane diterpenoids have attracted considerable interest due to their remarkable structural diversity and great antimalarial, 4 antibacterial, 5 antifungal, 6 antiviral, 7,8 phytotoxic, 6 cytotoxic, [9][10][11][12] AChE-inhibitory, 13 and anti-inammatory activities.…”