Taglialatela-Scafati, OrazioPollastro, FedericaCicione, LaviniaChianese, GiuseppinaBellido, Maria LuzMunoz, EduardoOzen, Hasan Cetin2024-04-242024-04-2420120163-38641520-6025https://doi.org/10.1021/np2008973https://hdl.handle.net/11468/16406Apart from a large amount (ca. 2.0%) of alpha-bisabolol beta-D-fucopyranoside (2a), the aerial parts of the Mediterranean weed Carthamus glaucus afforded an unusual triglyceride (E-2-crotonyl-1,3-distearolylglycerol, 7), two lipophilic flavonoids (6a,b), and a series of bisabolane fucopyranosides variously acylated on the sugar moiety (2b-e) or oxidized on the terpenoid core (3, 4a,b, 5a,b). The fucopyranoside 2a is more soluble in polar media and more versatile in terms of formulation than its aglycone [(-)-alpha-bisabolol, 1], an anti-inflammatory cosmetic ingredient in current short supply in its natural form. A comparative investigation of the activity of alpha-bisabolol (1a), the fucopyranoside 2a, and its senecioate 2b on transcription factors involved in inflammation and cancer pathways (NF-kappa B and STAT-3) showed only marginal activity on NF-kappa B inhibition for all compounds, while STAT-3 was inhibited potently by the fucoside 2a and, to a lesser extent, also by a-bisabolol. These observations qualify 2a as an easily available compound, both as an apoptotic lead structure and as a potential alternative to natural a-bisabolol (1) for pharmaceutical and/or cosmetic development.eninfo:eu-repo/semantics/closedAccess[No Keyword]Article753453458WOS:0003018107000182-s2.0-848590174592230925010.1021/np2008973Q1Q1