Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli Federico II, Via Montesano 49, 80131 Napoli, Italy.
J Nat Prod. 2012 Mar 23;75(3):453-8. doi: 10.1021/np2008973. Epub 2012 Feb 6.
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.
除了大量的α- 红没药醇 β-D- 呋喃果糖苷（2a）（约 2.0%）外，地中海杂草矢车菊的地上部分还提供了一种不寻常的三酰基甘油（E-2- 巴豆酰基-1,3- 二硬脂酰基甘油，7），两种亲脂性类黄酮（6a,b），以及一系列不同糖基酰化的倍半萜呋喃糖苷（2b-e）或萜烯核氧化（3,4a,b,5a,b）。与糖苷配基（-)-α- 红没药醇（1）相比，呋喃糖苷 2a 在极性介质中更具溶解性，在制剂方面更具多功能性，而 1 是当前天然形式下抗炎化妆品成分的短缺。对 α- 红没药醇（1a）、呋喃糖苷 2a 及其菊苣酸盐 2b 对参与炎症和癌症途径的转录因子（NF-κB 和 STAT-3）的活性进行比较研究表明，所有化合物对 NF-κB 抑制的活性都很微弱，而 STAT-3 被呋喃糖苷 2a 强烈抑制，而 α- 红没药醇的抑制作用较弱。这些观察结果表明，2a 作为一种易于获得的化合物，无论是作为凋亡的先导结构，还是作为天然 α- 红没药醇（1）的潜在替代品，都具有用于药物和/或化妆品开发的潜力。
