Institute of Traditional Chinese Medicine & Natural Products, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy , Jinan University , Guangzhou 510632 , People's Republic of China.
Integrated Chinese and Western Medicine Postdoctoral Research Station , Jinan University , Guangzhou 510632 , People's Republic of China.
J Nat Prod. 2018 Oct 26;81(10):2259-2265. doi: 10.1021/acs.jnatprod.8b00576. Epub 2018 Oct 9.
Eight new matrine-type alkaloids, flavesines G-J (1-4), alopecurine B (5), 7,11-dehydro-oxymatrine (6), 10-oxy-5,6-dehydromatrine (7), and 10-oxysophoridine (8), along with nine known analogues (9-17) were isolated from the roots of Sophora flavescens. Compounds 1-3 are the first natural matrine-type alkaloids with an open-loop ring D, while compound 4 represents an unprecedented dimerization pattern constructed from matrine and piperidine, and 5 is the first example of a matrine-type alkaloid with cleavage of the C-5-C-6 bond. The new structures were elucidated by means of spectroscopic data analysis (including NMR, MS, IR, and UV), and the absolute configurations were determined using single-crystal X-ray diffraction and ECD data. The isolated alkaloids were evaluated for their antiviral activity against hepatitis B virus, and compounds 1, 4, 5, 10, and 14 exhibited comparable antiviral potencies to matrine.
从苦参根部分离得到了 8 种新的苦参碱型生物碱，包括 flavesines G-J（1-4）、阿朴苦参碱 B（5）、7,11-去氢氧化苦参碱（6）、10-氧-5,6-去氢苦参碱（7）和 10-氧苦参碱（8），以及 9-17 种已知类似物。化合物 1-3 是具有开环环 D 的第一类天然苦参碱型生物碱，而化合物 4 代表了由苦参碱和哌啶组成的前所未有的二聚化模式，化合物 5 是首例具有 C-5-C-6 键断裂的苦参碱型生物碱。新结构通过光谱数据分析（包括 NMR、MS、IR 和 UV）阐明，绝对构型通过单晶 X 射线衍射和 ECD 数据确定。对分离得到的生物碱进行了抗乙型肝炎病毒活性评价，化合物 1、4、5、10 和 14 表现出与苦参碱相当的抗病毒活性。
