Wu Hong-Ru, He Xiao-Feng, Jin Xiao-Jie, Pan Hui, Shi Zhuan-Ning, Xu Dong-Dong, Yao Xiao-Jun, Zhu Ying
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China.
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China.
Fitoterapia. 2015 Oct;106:175-83. doi: 10.1016/j.fitote.2015.09.002. Epub 2015 Sep 4.
Five new nor-ursane type triterpenoids, gelse-norursane A-E, together with twenty known compounds, were isolated from the whole plant of Gelsemium elegans. The structures of new compounds were established as (2R,3R,7R,17S,19R)-2,3,7,19-tetrahydroxy-6-oxo-24-norurs-4(23),12-dien-28-oic acid (1), (2R,3R,7R,17S)-2,3,7-trihydroxy-6-oxo-24-norurs-4(23), 12-dien-28-oic acid (2), (2R,3R,7R,17S)-2,3,4-trihydroxy-23-norurs-20(30),12-dien-28-oic acid (3), (2R,3R,30R)-2,3-dihydroxy-24-norurs-4(23),12-dien-30-oic acid (4), and (2R,3R,30R)-2, 3-dihydroxy-24-norurs-4,12-dien-30-oic acid (5), using spectroscopic analysis, including HRESIMS, 1D and 2D NMR. The absolute configurations of 1 and 4 were established through comparison of experimental and calculated ECD spectra. The gelse-norursane A-E are isolated as the 24-nor-ursane type triterpenoids from the family Loganiaceae for the first time. The cytotoxicities of the selected compounds against a panel of four human cancer HL60, Hela, Hep-G2, and Smmc 7221 cell lines were evaluated using the MTT assay in vitro.
从钩吻全草中分离得到5个新的降乌苏烷型三萜化合物，即钩吻降乌苏烷A - E，以及20个已知化合物。通过高分辨电喷雾电离质谱（HRESIMS）、一维和二维核磁共振谱等光谱分析方法，确定新化合物的结构分别为(2R,3R,7R,17S,19R)-2,3,7,19 - 四羟基 - 6 - 氧代 - 24 - 降乌苏 - 4(23),12 - 二烯 - 28 - 酸（1）、(2R,3R,7R,17S)-2,3,7 - 三羟基 - 6 - 氧代 - 24 - 降乌苏 - 4(23),12 - 二烯 - 28 - 酸（2）、(2R,3R,7R,17S)-2,3,4 - 三羟基 - 23 - 降乌苏 - 20(30),12 - 二烯 - 28 - 酸（3）、(2R,3R,30R)-2,3 - 二羟基 - 24 - 降乌苏 - 4(23),12 - 二烯 - 30 - 酸（4）和(2R,3R,30R)-2,3 - 二羟基 - 24 - 降乌苏 - 4,12 - 二烯 - 30 - 酸（5）。通过比较实验和计算的电子圆二色谱（ECD）光谱确定了1和4的绝对构型。钩吻降乌苏烷A - E是首次从马钱科植物中分离得到的24 - 降乌苏烷型三萜化合物。采用MTT法体外评价了所选化合物对人HL60、Hela、Hep - G2和Smmc 7221四种癌细胞系的细胞毒性。
