New coumarin glycosides from endemic Prangos heyniae H. Duman & MF Watson

被引:14
作者
Albayrak, Gokay [1 ,2 ]
Demir, Serdar [2 ]
Kose, Fadime Aydin [3 ]
Baykan, Sura [2 ]
机构
[1] Izmir Katip Celebi Univ, Fac Pharm, Dept Pharmaceut Bot, Izmir, Turkey
[2] Ege Univ, Dept Pharmaceut Bot, Fac Pharm, Izmir, Turkey
[3] Izmir Katip Celebi Univ, Fac Pharm, Dept Biochem, Izmir, Turkey
关键词
Prangos; Apiaceae; coumarin; cytotoxicity; ANTIOXIDANT ACTIVITIES; ESSENTIAL OIL; CONSTITUENTS; PLANT; FURANOCOUMARIN; APIACEAE; FRUITS; IDENTIFICATION; DERIVATIVES; ANATOLIA;
D O I
10.1080/14786419.2021.1961138
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Two new coumarin glycosides, named 7-methoxy isoarnottinin 4'-O-beta-D-glucopyranoside and 7-methoxy isoarnottinin 4'-O-rutinoside (1 and 2) along with six known compounds (3-8) were isolated from the roots of Prangos heyniae, an endemic plant of Turkey. 1-methylethyl 6-O-D-apio-beta-D-furanosyl-beta-D-glucopyranoside (7) and cnidioside A (8) have been obtained from the genus Prangos for the first time. Structures of isolated compounds were established using spectroscopic methods (1D and 2D NMR, HR-MS, UV and IR). Moreover, all extracts and isolated compounds were evaluated for their cytotoxic activity against NIH/3T3, HK-2, A-549, MCF-7, PC-3 and SH-SY5Y cell lines by WST-1 method. One of the new coumarin glycosides, 7-methoxy isoarnottinin 4'-O-beta-D-glucopyranoside (1) exhibited selective cytotoxic activity against SH-SY5Y cells with IC50 value of 31.41 +/- 1.04 mu M. [GRAPHICS]
引用
收藏
页码:227 / 239
页数:13
相关论文
共 53 条
[11]   Lipid Peroxidation and Cyclooxygenase Enzyme Inhibitory Compounds from Prangos haussknechtii [J].
Dissanayake, Amila A. ;
Ameen, Baram A. H. ;
Nair, Muraleedharan G. .
JOURNAL OF NATURAL PRODUCTS, 2017, 80 (09) :2472-2477
[12]  
Duman H., 1999, Edinburgh Journal of Botany, V56, P199
[13]   COUMARINS AND COUMARIN GLUCOSIDES FROM THE FRUITS OF AMMI-MAJUS [J].
ELGAMAL, MHA ;
SHALABY, NMM ;
DUDDECK, H ;
HIEGEMANN, M .
PHYTOCHEMISTRY, 1993, 34 (03) :819-823
[14]   Glycosidic Acids with Unusual Aglycone Units from Convolvulus arvensis [J].
Fan, Bo-Yi ;
He, Ye ;
Lu, Yun ;
Yang, Min ;
Zhu, Qing ;
Chen, Guang-Tong ;
Li, Jian-Lin .
JOURNAL OF NATURAL PRODUCTS, 2019, 82 (06) :1593-1598
[15]   Isolation, Cytotoxicity Evaluation and HPLC-Quantification of the Chemical Constituents from Prangos pabularia [J].
Farooq, Saleem ;
Shakeel-u-Rehman ;
Dangroo, Nisar Ahmad ;
Priya, Dev ;
Banday, Javid Ahmad ;
Sangwan, Pyare Lal ;
Qurishi, Mushtaq Ahmad ;
Koul, Surrinder ;
Saxena, Ajit Kumar .
PLOS ONE, 2014, 9 (10)
[16]   Structural and optical studies of 7-methoxy-8-(3-metrhylbut-2-enyl)-2-chromenone (osthol), a plant based coumarin [J].
Farozi, Alia ;
Shah, Shakeel A. ;
Banday, Javid A. .
OPTIK, 2016, 127 (05) :2802-2805
[17]  
Fujioka T, 1999, CHEM PHARM BULL, V47, P96, DOI 10.1248/cpb.47.96
[18]   An efficient approach for the isolation, identification and evaluation of antimicrobial plant components on an analytical scale, demonstrated by the example of Radix imperatoriae [J].
Goekay, O. ;
Kuehner, D. ;
Los, M. ;
Goetz, F. ;
Bertsche, U. ;
Albert, K. .
ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 2010, 398 (05) :2039-2047
[19]  
Guner A., 2012, Turkiye Bitkileri Listesi (Damarli Bitkiler).
[20]   Ruminococcus gnavus, a member of the human gut microbiome associated with Crohn's disease, produces an inflammatory polysaccharide [J].
Henke, Matthew T. ;
Kenny, Douglas J. ;
Cassilly, Chelsi D. ;
Vlamakis, Hera ;
Xavier, Ramnik J. ;
Clardy, Jon .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2019, 116 (26) :12672-12677