Abstract
Twenty-seven naphthoquinones and their derivatives, including four new naphthalenyl glucosides and twenty-three known compounds, were isolated from green walnut husks, which came from Juglans mandshurica Maxim. The structures of four new naphthalenyl glucosides were elucidated based on extensive spectroscopic analyses. All of these compounds were evaluated for their cytotoxic activities against the growth of human cancer cells lines HepG-2 by MTT [3-(4,5-dimethylthiazo l-2-yl)-2,5 diphenyl tetrazolium bromide] assay. The results were shown that most naphthoquinones in an aglycone form exhibited better cytotoxicity in vitro than naphthalenyl glucosides with IC50 values in the range of 7.33–88.23 μM. Meanwhile, preliminary structure-activity relationships for these compounds were discussed.
Highlights
With the increased use of natural product-based cancer chemotherapy, exploring the cytotoxic activity of phytochemicals for anticancer drug design has gained extensive attention worldwide [1].Juglans mandshurica Maxim is a well-known member of the Juglandaceae family which is widely distributed throughout urban and rural areas in northeast China [2,3,4]
The aim of this work was to define the key naphthoquinone structural elements that were required for cytotoxic activity through the determination of the ability of 27 naphthoquinones belonging to main structural subtypes such as naphthoquinone, tetralone, and naphthols
The structures of four new naphthalenyl glucosides were elucidated based on extensive mass and spectroscopic analyses including High resolution-electron spray ionization (HR-ESI)-MS, IR, 1H-NMR, 13C-NMR, distortionless enhancement by polarization transfer (DEPT), HSQC, HMBC, and CD
Summary
Juglans mandshurica Maxim is a well-known member of the Juglandaceae family which is widely distributed throughout urban and rural areas in northeast China [2,3,4]. A few distrubute in Russia, Korea and Japan. It is one of the most important medical plants of which the green husks, leaf, root and bark all can be medically used [5,6,7,8]. Its green husks have been used as a folk medicine for treatment of gastric ulcers, uterine prolapse, leukopenia, diarrhea and dysentery for many years in China [9]. Many studies showed that green walnut husks have obvious advantages in tumor treatment like liver cancer [9,10,11]
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