Tigliane and daphnane diterpenoids from Thymelaeaceae family: chemistry, biological activity, and potential in drug discovery

Abstract

Tigliane and daphnane diterpenoids are characteristically distributed in plants of the Thymelaeaceae family as well as the Euphorbiaceae family and are structurally diverse due to the presence of polyoxygenated functionalities in the polycyclic skeleton. These diterpenoids are known as toxic components, while they have been shown to exhibit a wide variety of biological activities, such as anti-cancer, anti-HIV, and analgesic activity, and are attracting attention in the field of natural product drug discovery. This review focuses on naturally occurring tigliane and daphnane diterpenoids from plants of the Thymelaeaceae family and provides an overview of their chemical structure, distribution, isolation, structure determination, chemical synthesis, and biological activities, with a prime focus on the recent findings.

Isolation and Identification of 12-Deoxyphorbol Esters from Euphorbia resinifera Berg Latex: Targeted and Biased Non-Targeted Identification of 12-Deoxyphorbol Esters by UHPLC-HRMSE

“…On the other hand, the calculated ECD spectra for 12-deoxyphorbol esters 13 and 14 and for 12,20-dideoxyphorbol ester 15, predict positive, non-overlapped Cotton effects in the 220-240 nm and 240-260 nm ranges, which can be attributed to transitions π → π* [38]. These Cotton effects can be observed in the experimental ECD spectra for diDPB (15) (Figure 11).…”

“…Compounds 1-15 were identified as components in a targeted analysis. Compounds 19-22 were identified as components in a biased non-targeted analysis [38,39].…”

“…Data acquisition and further processing were performed by MassLynx 4.1 software package (Waters, Manchester, UK) in positive-ion mode. Automated peak detection was performed using the "targeted-fragment ion confirmation" algorithm, while the "non-targeted" algorithm was used to carry out a biased non-targeted analysis [38,39]; both algorithms are included in the ChromaLynx XS module within the MassLynx package. Retention time and mass tolerance were adjusted to ±0.2 min and ±10 mDa for targeted analysis.…”

Total Syntheses of Phorbol and 11 Tigliane Diterpenoids and Their Evaluation as HIV Latency-Reversing Agents

“…Tigliane terpenoids are isolated from extracts of Euphorbiaceae and Thymelaeaceae , which are widely used in traditional medicine . To date, more than 250 family members with diverse oxidation states and acylation patterns have been identified and shown to display a broad range of biological functions depending on their decorating substructures (Scheme ).…”

Conversion of Phorbol into Des-D-Ring Tricycle and Crotonianoid B via Peroxidation Reaction

“…Phorbol ( 1 , Scheme ) was structurally revealed in 1967 to possess a 5/7/6/3 tetracyclic ring system (ABCD-ring) with six oxygen functionalities . Compound 1 is a representative example of tigliane diterpenoids, a family comprising more than 250 members …”