Fmoc-MAP(2)-Alko-PEG Resin

Following the successful introduction of two benign solvents for cleaving protected acid peptide fragments from 2-chlorotrityl chloride (2-CTC) resin, there is a need to green the cleavage process for obtaining protected peptide amide fragments. In this work, p-xylene and toluene are introduced as greener alternates to dichloromethane (DCM) for preparing protected peptide amide fragments from a Sieber amide resin. The N-dealkylation is a demanding chemical reaction, requiring that the cleavage protocol be optimised to ensure complete cleavage from the resin. After a 30 min reaction time, only 66 % of the final peptide product was retrieved even with the conventional dichloromethane solvent. Therefore, 120 min was considered sufficient to fully cleave the peptide from the Sieber amide resin. This work reaffirms the fact that greening strategies are far from detrimental, with green alternatives often outperforming their replaced counterparts.

Frankincense of Boswellia species has long been used in traditional medicines, mainly for its interesting anti-inflammatory and anti-depressant properties of its di- and triterpenes. Boswellic acids (triterpenes) and cembranoids (diterpenes) are the major constituents of frankincense from all reported species which are responsible for the overall biological activity of frankincense. Boswellic acids have been thoroughly investigated for decades but cembranoids have attracted considerable attention only recently, and a good number of publications have highlighted the important role of these 14-membered rings in contributing to the superior anti-inflammatory activity of the sacred resin. Partial and total syntheses of some cembranoids from frankincense have been reported. Their therapeutic potential is not limited to the well proven anti-inflammatory activity but also to their recently reported anti-depressant properties. There is a considerable number of publications in the field of cembranoids of Boswellia species where we feel a review in this topic will be of interest to the readership of Phytochemistry. In this article we have discussed the chemistry (isolation and chemical structures as well as synthetic studies), biogenesis and bioactivity of the reported cembranoids of Boswellia species. The structural discrepancies due to wrongly assigned structures of some cembranoids have been highlighted and corrected. We have covered the related literature up to the end of 2020.