Orazio Taglialatela-Scafati*†, Federica Pollastro‡, Lavinia Cicione‡, Giuseppina Chianese†, Maria Luz Bellido§, Eduardo Munoz
, Hasan Çetin Özen
, Zuhal Toker, and Giovanni Appendino*‡
, Hasan Çetin Özen, Zuhal Toker, and Giovanni Appendino*‡ † Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli Federico II, Via Montesano 49, 80131 Napoli, Italy
‡ Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università del Piemonte Orientale, Via Bovio 6, 28100, Novara, Italy
§ VivaCell Biotechnology España, Parque Científico Tecnológico de Córdoba Rabanales 21, C/Cecilia Payne - ID 8.1, 14014 Córdoba, Spain
Departamento de Biología Celular, Fisiología e Inmunología, Facultad de Medicina, Universidad de Córdoba, Avenida de Menéndez Pidal s/n, 14004 Córdoba, SpainFen Fakültesi Biyoloji Bölümü, Dicle Üniversitesi, 21280 Diyarbakir, TurkeyJ. Nat. Prod., Article ASAP
DOI: 10.1021/np2008973
Publication Date (Web): February 6, 2012
Apart from a large amount (ca. 2.0%) of α-bisabolol β-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 [(−)-α-bisabolol, 1], an anti-inflammatory cosmetic ingredient in current short supply in its natural form. A comparative investigation of the activity of α-bisabolol (1a), the fucopyranoside 2a, and its senecioate 2b on transcription factors involved in inflammation and cancer pathways (NF-κB and STAT-3) showed only marginal activity on NF-κB inhibition for all compounds, while STAT-3 was inhibited potently by the fucoside 2a and, to a lesser extent, also by α-bisabolol. These observations qualify 2a as an easily available compound, both as an apoptotic lead structure and as a potential alternative to natural α-bisabolol (1) for pharmaceutical and/or cosmetic development.
