Seven new azacyclo-indoles and phenolics and four known alkaloids were isolated from the flowers of Juglans regia. Spectroscopic and chromatographic data revealed that the structures of the new compounds are 5,6,11,12-tetrahydropyrrolo[1′,2′:1,2]azepino[4,5-b]indole-3-carbaldehyde (1), (±)-5,6,7,11c-tetrahydro-1H-indolizino[7,8-b]indol-3(2H)-one (2), (±)-9-hydroxy-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-2-carboxamide (3), 5-(ethoxymethyl)-1-(4-hydroxyphenethyl)-1H-pyrrole-2-carbaldehyde (4), (±)-5,8-dihydroxy-4-(1H-indol-3-yl)-3,4-dihydronaphthalen-1(2H)-one (5), (±)-4-(6-amino-9H-purin-9-yl)-5,8-dihydroxy-3,4-dihydronaphthalen-1(2H)-one (6), and (±)-4-(6-amino-9H-purin-9-yl)-5-hydroxy-3,4-dihydronaphthalen-1(2H)-one (7). The five pairs of enantiomers were resolved, and the absolute configurations of the enantiomers were assigned via electronic circular dichroism data. Compound 1 exhibited significant in vitro growth inhibition against the HCT-116, HepG2, BGC-823, NCI-H1650, and A2780 cancer cell lines, with IC₅₀ values of 2.87, 1.87, 2.28, 2.86, and 0.96 μM, respectively, and low cytotoxicity toward normal IEC-6 cells, with a 79.6% survival rate at a 10 μM concentration.

中文翻译：

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胡桃木花中的氮杂环吲哚和酚类

从胡桃木的花中分离出七个新的氮杂环吲哚和酚醛树脂以及四个已知的生物碱。光谱和色谱数据表明，新化合物的结构为5,6,11,12-四氢吡咯并[1'，2'：1,2，] azepino [4,5 - b ]吲哚-3-甲醛（1）， （±）-5,6,7,11c-四氢-1 H-吲哚并[7,8- b ]吲哚-3（2 H）-一（2），（±）-9-羟基-5-氧- 2,3,4,5-四氢-1 H-苯并[ b ]氮杂-2-羧酰胺（3），5-（乙氧基甲基）-1-（4-羟基苯乙基）-1 H-吡咯-2-甲醛（4），（±）-5,8-二羟基-4-（1H-吲哚-3-基）-3,4-二氢萘-1（2 H）-一（5），（±）-4-（6-氨基-9 H-嘌呤-9-基）-5,8 -二羟基-3,4-二氢萘-1（2 H）-一（6）和（±）-4-（6-氨基-9 H-嘌呤-9-基）-5-羟基-3,4-二氢萘-1（2 H）-一（7）。解析了五对对映异构体，并通过电子圆二色性数据分配了对映异构体的绝对构型。化合物1对HCT-116，HepG2，BGC-823，NCI-H1650和A2780癌细胞系表现出明显的体外生长抑制作用，IC ₅₀ 分别为2.87、1.87、2.28、2.86和0.96μM，对正常IEC-6细胞的细胞毒性低，在10μM浓度下的存活率为79.6％。