Büchele Berthold, Zugmaier Waltraud, Estrada Aidee, Genze Felicitas, Syrovets Tatiana, Paetz Christian, Schneider Bernd, Simmet Thomas
Institute of Pharmacology of Natural Products and Clinical Pharmacology, University of Ulm, Ulm, Germany.
Planta Med. 2006 Nov;72(14):1285-9. doi: 10.1055/s-2006-951680. Epub 2006 Oct 4.
3Alpha-acetyl-11-keto-alpha-boswellic acid (3alpha-acetoxy-11-oxo-olean-12-en-24-oic acid, 1) was synthesized by a radical-type reaction using bromine and 3alpha-acetyl-alpha-boswellic acid isolated from the oleo-gum-resin of Boswellia carterii. 1D and 2D NMR (COSY, HMBC, ROESY) at 500 MHz were used for shift assignments and structure verification. The compound investigated is present in a herbal preparation extracted from Boswellia serrata oleo-gum-resin, it inhibits the growth of chemotherapy-resistant human PC-3 prostate cancer cells in vitro and induces apoptosis as shown by activation of caspase 3 and the induction of DNA fragmentation. In addition, compound 1 is active IN VIVO as shown by inhibition of proliferation and induction of apoptosis in PC-3 prostate cancer cells xenotransplanted onto the chick chorioallantoic membrane.
通过自由基型反应，利用从卡氏乳香树的油胶树脂中分离得到的溴和3α-乙酰-α-乳香酸合成了3α-乙酰基-11-酮-α-乳香酸（3α-乙酰氧基-11-氧代-齐墩果-12-烯-24-酸，1）。采用500 MHz的一维和二维核磁共振（COSY、HMBC、ROESY）进行化学位移归属和结构验证。所研究的化合物存在于从锯叶乳香树油胶树脂中提取的草药制剂中，它在体外抑制化疗耐药的人PC-3前列腺癌细胞的生长，并通过激活半胱天冬酶3和诱导DNA片段化诱导细胞凋亡。此外，化合物1在体内也具有活性，这表现为对移植到鸡胚绒毛尿囊膜上的PC-3前列腺癌细胞的增殖抑制和凋亡诱导。
