College of Animal Science and Veterinary Medicine, Jilin University, No. 5333 Xi'an Road, Changchun, Jilin 130062, PR China.
Fitoterapia. 2013 Jan;84:303-7. doi: 10.1016/j.fitote.2012.12.021. Epub 2012 Dec 22.
Ginsenoside Rh2 is one of the most important ginsenosides in ginseng with antitumor, antidiabetic, antiallergic, and anti-inflammatory effects. However, the extremely poor oral bioavailability induced by its low water solubility greatly limits the potency of Rh2 in clinical use. Therefore, in this study we sulfated 20(S)-ginsenoside Rh2 with chlorosulfonic acid and pyridine method, and got two new sulfated derivatives, Rh2-B1 and Rh2-B2, with higher water solubility. Their chemical structures were characterized by spectroscopic methods (IR, MS and NMR). Additionally, Rh2-B1 and Rh2-B2 had the greater anti-inflammatory effects than Rh2 through inhibiting inflammatory cytokines and mediators in LPS-induced mouse RAW264.7 macrophages cells. These results suggested that the sulfated modification of Rh2 improved its water solubility and the sulfated derivatives could be more potential candidates for developing as anti-inflammatory agents.
人参皂苷 Rh2 是人参中最重要的皂苷之一，具有抗肿瘤、抗糖尿病、抗过敏和抗炎作用。然而，其极低的水溶性导致的极差的口服生物利用度极大地限制了 Rh2 在临床应用中的效力。因此，在本研究中，我们采用氯磺酸-吡啶法对 20(S)-人参皂苷 Rh2 进行了硫酸化修饰，得到了两个水溶性更高的新硫酸化衍生物 Rh2-B1 和 Rh2-B2。通过光谱学方法（IR、MS 和 NMR）对其化学结构进行了表征。此外，通过抑制 LPS 诱导的 RAW264.7 巨噬细胞中炎症细胞因子和介质，Rh2-B1 和 Rh2-B2 比 Rh2 具有更强的抗炎作用。这些结果表明，Rh2 的硫酸化修饰提高了其水溶性，硫酸化衍生物可能是开发抗炎药物的更有潜力的候选药物。
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