Structural Modification of Stilbenoids from Acanthopanax leucorrhizus and Their Cytotoxic Activity

被引:2
作者
Hu, Hao-Bin [1 ]
Liang, Hai-Peng [2 ]
Li, Hai-Ming [1 ]
Yuan, Ru-Nan [3 ]
Sun, Jiao [3 ]
Wu, Yun [1 ]
Zhang, La-La [1 ]
Han, Ming-Hu [1 ]
机构
[1] Longdong Univ, Coll Chem & Chem Engn, Qingyang 745000, Peoples R China
[2] Qingyang First Peoples Hosp, Dept Oncol, Qingyang 745000, Peoples R China
[3] Gansu Agr Univ, Coll Food Sci & Engn, Lanzhou 730070, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
Acanthopanax leucorrhizus; Stilbenoids; Isolation; Structural modification; Cytotoxic activity; ROOT BARK; LEAVES;
D O I
10.1002/cbdv.201700244
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A new cis-stilbenoid, 1,9-dihydroxy-10-methoxy-6H-dibenzo[b,f]oxocin-6-one (2) was isolated from the AcOEt extract of the stem barks of Acanthopanax leucorrhizus, along with three known stilbenoids, 9-hydroxy-10-methoxy-6H-dibenzo[b,f]oxocin-6-one (1), 5-O-methyl-(E)-resveratrol 3-O--d-glucopyranoside (3), and (E)-resveratrol 3-O--d-xylopyranoside (4). Two derivatives (2a and 2b) were synthesized by the structural modification of compound 2, which exhibited certain cytotoxic activities against HT-29 and HeLa cell lines invitro. All compounds were structurally characterized by comprehensive analysis of their spectroscopic data and comparison with literature information, and evaluated for their cytotoxic activities against three human tumor cell lines (HL-60, HT-29, and HeLa) by the standard MTT assay invitro. The results showed that derivatives 2a and 2b exhibited strong activities than compounds 2 against HT-29 and HeLa cell lines.
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页数:6
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共 21 条
[1]   Plant foods and herbal sources of resveratrol [J].
Burns, J ;
Yokota, T ;
Ashihara, H ;
Lean, MEJ ;
Crozier, A .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2002, 50 (11) :3337-3340
[2]   Stilbenoids from Rheum undulatum Protect Hepatocytes Against Oxidative Stress Through AMPK Activation [J].
Dong, Guang-zhi ;
Lee, Yu-ih ;
Jeong, Ji Hye ;
Zhao, Hui-Yuan ;
Jeon, Raok ;
Lee, Hwa Jin ;
Ryu, Jae-Ha .
PHYTOTHERAPY RESEARCH, 2015, 29 (10) :1605-1609
[3]   A stilbene xyloside from Holodiscus discolor bark [J].
GonzalezLaredo, RF ;
ChaidezGonzalez, J ;
Ahmed, AA ;
Karchesy, JJ .
PHYTOCHEMISTRY, 1997, 46 (01) :175-176
[4]   Trans- and cis-stilbene polyphenols induced rapid perinuclear mitochondrial clustering and p53-independent apoptosis in cancer cells but not normal cells [J].
Gosslau, Alexander ;
Pabbaraja, Srihari ;
Knapp, Spencer ;
Chen, Kuang Yu .
EUROPEAN JOURNAL OF PHARMACOLOGY, 2008, 587 (1-3) :25-34
[5]   Synthesis and evaluation of double bond substituted combretastatins [J].
Hadfield, JA ;
Gaukroger, K ;
Hirst, N ;
Weston, AP ;
Lawrence, NJ ;
McGown, AT .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (06) :529-541
[6]   Sesquiterpenoids from the Root Bark of Acanthopanax leucorrhizus and Their Biological Activities [J].
Hu, Hao-Bin ;
Zhang, Peng-Hui ;
Wu, Yun .
HELVETICA CHIMICA ACTA, 2014, 97 (09) :1283-1288
[7]   Chemical composition, antimicrobial, antioxidant and cytotoxic activity of the essential oil from the leaves of Acanthopanax leucorrhizus (Oilv.) Harms [J].
Hu, Haobin ;
Zheng, Xudong ;
Hu, Huaisheng .
ENVIRONMENTAL TOXICOLOGY AND PHARMACOLOGY, 2012, 34 (02) :618-623
[8]   Five new prenylated stilbenes from the root bark of Lonchocarpus chiricanus [J].
Ioset, JR ;
Marston, A ;
Gupta, MP ;
Hostettmann, K .
JOURNAL OF NATURAL PRODUCTS, 2001, 64 (06) :710-715
[9]   Bioactive cis-stilbenoids from the tubers of Scirpus yagara [J].
Liang, Qiao-Li ;
Lei, Ling-Ling ;
Cui, Xiaodong ;
Zou, Nuo-Shu ;
Duan, Jin-Ao .
FITOTERAPIA, 2013, 84 :170-173
[10]   Syntheses of differentially protected isocoumarins [J].
Lowell, Andrew N. ;
Wall, Philip D. ;
Waters, Stephen P. ;
Kozlowski, Marisa C. .
TETRAHEDRON, 2010, 66 (30) :5573-5582