TY - JOUR
T1 - STAT-3 inhibitory bisabolanes from carthamus glaucus
AU - Taglialatela-Scafati, Orazio
AU - Pollastro, Federica
AU - Cicione, Lavinia
AU - Chianese, Giuseppina
AU - Bellido, Maria Luz
AU - Munoz, Eduardo
AU - Özen, Hasan Çetin
AU - Toker, Zuhal
AU - Appendino, Giovanni
PY - 2012/3/23
Y1 - 2012/3/23
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84859017459&partnerID=8YFLogxK
U2 - 10.1021/np2008973
DO - 10.1021/np2008973
M3 - Article
SN - 0163-3864
VL - 75
SP - 453
EP - 458
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 3
ER -