Isocoumarin derivatives and monoterpene glycoside from the seeds of Orychophragmus violaceus

Electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens involving C–S/Se bond formation

“…Iso-coumarins are privileged scaffolds found in bioactive natural products and pharmaceuticals. 55 In 2020, Guo et al reported an efficient continuous electrocatalytic strategy via the difunctionalization of alkynes to synthesise selenium-substituted iso-coumarin derivatives under oxidant-free and metal-free conditions (Scheme 42). 56 a Substrates containing cycloalkane, a thiophene ring, and a naphthalene ring, as well as alkyl substituents attached to alkynes also proved to be well tolerated under optimized conditions, providing the corresponding products in good yields.…”

Recent Advances in the Nutritional Value, Chemical Compositions, Pharmacological Activity, and Application Value of Orychophragmus violaceus: A Comprehensive Review

“…In published studies [ 13 ], three new iso-coumarins and one new dihydroisocoumarin were isolated from the seeds of O. violaceus : orychophramarin A–D.…”

“…Zhang Guangjie et al [ 13 ] used Hela and HCT-116 cells as in vitro tumor models and found that orychophramarin A, orychophramarin B, and orychophramarin C all had the activity of inhibiting the growth and proliferation of tumor cells in vitro. In particular, orychophramarin A showed a significant inhibitory effect on the above two cell lines, whose IC50 values, respectively, were 8.91 and 5.10 μM, which surpassed the efficacy of the positive drug cisplatin.…”

“…It has been established in modern pharmacological studies that the natural active ingredients in O. violaceus have a wide range of pharmacological activities, including antibacterial, antitumor, antiradiation, hepatic protection, and other physiological activities [ 9 , 10 , 11 ]. Based on domestic and foreign research, flavonoids [ 10 ], alkaloids [ 12 ], phenylpropanoids [ 13 ], phenolic acids [ 14 ], and terpenoids [ 15 ] have been identified as the main components of O. violaceus . Despite being present in relatively small amounts, O. violaceus’s steroid, fatty acid, protein, and vitamin content are crucial to the plant’s overall value.…”

Novel 3,4-Dihydroisocoumarins Inhibit Human P-gp and BCRP in Multidrug Resistant Tumors and Demonstrate Substrate Inhibition of Yeast Pdr5

“…To date, several 100 different isocoumarins and dihydroisocoumarins from nature have been identified and derivatives have been synthesized. Owing to their great structural diversity, diverse biological and pharmacological activities of isocoumarins including cytotoxicity and antimetastatic effects against various cancer types including breast, colon, melanoma (Cichewicz et al, 2004; Abid et al, 2012; Guimarães et al, 2016; Zhang et al, 2017), inhibition of inflammation (Liang et al, 2011; Ramanan et al, 2016) or different enzymes including aromatase and kallikrein peptidases as potential cancer targets (Endringer et al, 2008; Teixeira et al, 2011) as well as antibacterial, antifungal and antimalarial activities (Hoepfner et al, 2012; Lai et al, 2016; Simic et al, 2016) could be identified. Several natural or synthetic coumarins were identified as inhibitors of either P-gp, BCRP or both, yet activities were mostly moderate, and compound concentrations between 10 and 100 μM had to be applied for transporter inhibition (Barthomeuf et al, 2005; Raad et al, 2006; Combes et al, 2011; Bisi et al, 2017; Sjöstedt et al, 2017).…”