Azacyclo-indoles and Phenolics from the Flowers of Juglans regia

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...

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Published in:Journal of natural products (Washington, D.C.) D.C.), 2017-08, Vol.80 (8), p.2189-2198
Main Authors: Li, Qian, Deng, An-Jun, Li, Li, Wu, Lian-Qiu, Ji, Ming, Zhang, Hai-Jing, Li, Zhi-Hong, Ma, Lin, Zhang, Zhi-Hui, Chen, Xiao-Guang, Qin, Hai-Lin
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Aldehydes - isolation & purification
Aldehydes - pharmacology
Alkaloids - chemistry
Alkaloids - isolation & purification
Alkaloids - pharmacology
Azepines - chemistry
Azepines - isolation & purification
Azepines - pharmacology
Cell Line, Tumor
Circular Dichroism
Flowers - chemistry
Humans
Indoles - chemistry
Indoles - isolation & purification
Indoles - pharmacology
Inhibitory Concentration 50
Juglans - chemistry
Molecular Structure
Phenols - chemistry
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Summary: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.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.6b00887