Synthesis and biological evaluation of Pseudostellarin D

The cyclization of peptides and depsipeptides

“…In the synthesis of phakellistatin-2 cyclo (Tyr-Pro-Phe-Pro-Ile-Ile-Pro 7 ), cyclization at the Pro 7 position proceeded in 50%-65% yield using TBTU, BOP-Cl, PyBroP or HOAt, with TBTU giving the consistently highest yield [118]. Pseudostellarin D, cyclo (Gly-Gly-Tyr-Pro-Leu-Ile-Leu) has been synthesized in the solution phase [119] via pnitrophenyl ester which took 10 days to achieve success. In contrast, for the synthesis of stylostatin, cyclo (Ile-Pro-Phe-Asn-EtGly-Leu-Ala), a resin linker attached to the α-nitrogen of a C-terminal residue (Ala in this case), was used to assemble the linear precursor, which was then cyclized on-resin [120].…”

Comparative chemical characters of Pseudostellaria heterophylla from geographical origins of China

“…Literatures have reported that pseudostellarin B was one of the major compounds in P. heterophylla which possesses extensive angiogenesis effects and antibacterial ( Lin, 2019 , Poojary et al, 2001 ). As characteristic components of P. heterophylla , the representative cyclic peptide exhibited a wide range of pharmacologic properties, such as antioxidant, anti-inflammation, antibacterial and anti-cancer ( Himaja et al, 1999 , Hiroshi et al, 1994 , Routhu et al, 2021 , Zhai et al, 2020 ). Apart from these functions, pseudostellarin E also has hypoglycemic effect with high levels in Fujian ( Zhang, Yao, Wang, Wen, & Chen, 2018 ).…”

Recyclable hypervalent-iodine-mediated solid-phase peptide synthesis and cyclic peptide synthesis

“…In addition, the authors reported that pseudostellarin D showed potent tyrosinase inhibitory activities. In 1999, Belagali and co-workers further evaluated the antimicrobial, anti-inflammatory and anthelmintic activities of pseudostellarin D [ 38 ]. As for the synthesis of pseudostellarin D, the existing methods utilized the active ester method to complete the cyclization of the linear peptide precursor with the same amino acid sequence of Gly-Gly-Tyr-Pro-Leu-Ile-Leu as a result of the amide bond between “Gly-Leu” being the cyclization position.…”