秦岭苦参中苦参碱立体异构体晶体结构研究

Crystal Structure of Stereoisomers of Matrine from Sophora flavescens in the Qin Mountain

从秦岭地区苦参中经过溶剂提取和酸化分离得到一种生物碱盐酸盐结晶1,该晶体不对称单元含有一对新的苦参碱非对映异构体,绝对构型分别是1S,5S,6S,7R,11R,165和1S,5S,6S,7R,11R,16R,命名为顺式新苦参碱(cis-neomatrine)和反式新苦参碱(trans-neomatrine).1的晶体结构(C_(15)H_(24)N_2O·C_(15)H_(24)N_2O·2HCl.5H_2O)属正交晶系,空间群P2_12_12_1,a=0.8053(2)nm,b=1.3464(5)nm,c=3.0971(9)nm,V=3.3580(18)nm^3,Z=4,μ=0.244 mm^(-1),F(000)=1432,R=0.0467,wR=0.1129.顺式新苦参碱和反式新苦参碱的A环、B环和C环为椅式构象,D环为半椅式构象,其中A/B为反式稠合,A/C和B/C为顺式稠合,两种立体异构体的区别是顺式新苦参碱的C/D顺式稠合,反式新苦参碱的C/D反式稠合.

A crystal of chlorohydrate alkaloid (1) was isolated by extraction and acidifying from Sophora flavescens in the Qin mountain. Two new matrines of diastereoisomers exist in the molecular structure of 1, named cis-neomatrine and trans-neomatrine. The absolute configurations of cis-neomatrine and trans-neomatrine are 1S, 5S, 6S, 7R, 11R, 16S, and 1S, 5S, 6S, 7R,11R, 16R, respectively. The crystal of 1 (C15H24N2O.C15H24N2O.2HCl.5H(2)O) crystallized in the Orthorhombic space group P2(1)2(1)2(1) with cell parameters a = 0.8053(2) rim, b = 1.3464 (5) rim, c = 3.0971(9) ran, V = 3.3580 (18) nm(3), Z = 4, mu = 0.244 mm(-1), F(000) = 1432, R = 0.0467, wR = 0.1129. In the structures of cis-neomatrine and trans-neomatrine, rings A, B, C have the chair form and D the half-chair form. Rings A and B, B and C, A and C have the trans type of linkage. Two stereoisomers differ from each other in the type of linkage between rings C and D. The rings C and D of cis-neomatrine have the cis type of linkage and that of trans-neomatrine have the trans type of linkage.