New acetylated flavone C-glycosides from Iris lactea

被引:8
|
作者
Whaley, Andrei K. [1 ,2 ]
Ebrahim, Weaam [1 ,3 ]
El-Neketi, Mona [3 ]
Ancheeva, Elena U. [1 ,2 ]
Ozkaya, Ferhat Can [1 ]
Pryakhina, Nina I. [2 ]
Sipkina, Nadezhda U. [2 ]
Luzhanin, Vladimir G. [2 ]
Liu, Zhen [1 ]
Proksch, Peter [1 ]
机构
[1] Heinrich Heine Univ Dusseldorf, Inst Pharmaceut Biol & Biotechnol, Univ Str 1, D-40225 Dusseldorf, Germany
[2] St Petersburg State Chem Pharmaceut Acad, St Prof Popova 14, St Petersburg 197376, Russia
[3] Mansoura Univ, Fac Pharm, Dept Pharmacognosy, Mansoura 35516, Egypt
关键词
Flavone C-glycosides; Rotamers; Iris lactea; GLYCOSYLFLAVONES; LEAVES;
D O I
10.1016/j.tetlet.2017.04.080
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chemical investigation of the aerial parts of Iris lactea afforded three new flavone C-glycosides including 4'''-O-acetyl-embinin (1), 2''',4"'-O-diacetyl-embinin (2) and 6 '',4"'-O-diacetyl-embinin (3) along with the known analogue embinin (4). Their structures were elucidated by 1D and 2D NMR spectroscopic analysis as well as by HRESIMS data. The sugars were characterized following acid hydrolysis of the respective glycosides and TLC analysis compared to known standards. Duplicated signals can be observed in the NMR spectra, indicating the presence of rotamers caused by rotational hindrance around the glycosyl-flavone C-C linkage. All isolated compounds were tested for their antimicrobial and cytotoxic activities but found to be inactive. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2171 / 2173
页数:3
相关论文
共 50 条
  • [1] ACYLATED C-GLYCOSIDES OF IRIS-LACTEA
    PRYKHINA, NI
    SHEICHENKO, VI
    BLINOVA, KF
    KHIMIYA PRIRODNYKH SOEDINENII, 1984, (05): : 589 - 595
  • [2] Two New Flavone C-Glycosides from Trollius ledebourii
    Wu, Li-Zhen
    Wu, Hai-Feng
    Xu, Xu-Dong
    Yang, Jun-Shan
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2011, 59 (11) : 1393 - 1395
  • [3] Flavone C-glycosides from Dendrobium gratiosissimum
    Song, Zhijun
    Liu, Jimei
    Li, Changkang
    Sun, Xincheng
    Chen, Dawei
    Chen, Ridao
    Xie, Kebo
    Han, Yaotian
    Dai, Jungui
    PHYTOCHEMISTRY LETTERS, 2023, 54 : 158 - 162
  • [4] Flavone C-glycosides from Anthurium andraeanum
    Clark, Benjamin R.
    Suzuki, Jon Y.
    Bliss, Barbara J.
    Borris, Robert P.
    NATURAL PRODUCT COMMUNICATIONS, 2012, 7 (06) : 747 - 748
  • [5] Flavone C-glycosides from Scleranthus uncinatus
    Yayli, N
    Seymen, H
    Baltaci, C
    PHYTOCHEMISTRY, 2001, 58 (04) : 607 - 610
  • [6] Flavone C-glycosides from Lupinus hartwegii
    Kamel, MS
    PHYTOCHEMISTRY, 2003, 63 (04) : 449 - 452
  • [7] DETERMINATION OF FLAVONE C-GLYCOSIDES IN TEA
    ENGELHARDT, UH
    FINGER, A
    KUHR, S
    ZEITSCHRIFT FUR LEBENSMITTEL-UNTERSUCHUNG UND-FORSCHUNG, 1993, 197 (03): : 239 - 244
  • [8] Flavone C-glycosides from leaves of Oxalis triangularis
    Rayyan, S
    Fossen, T
    Andersen, OM
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (26) : 10057 - 10060
  • [9] FLAVONE C-GLYCOSIDES FROM MOLLUGO-HIRTA
    NAIR, AGR
    GUNASEGARAN, R
    CURRENT SCIENCE, 1983, 52 (06): : 248 - 249
  • [10] Flavone C-glycosides from flowers of Trollius ledebouri
    Zou, JH
    Yang, JS
    Dong, YS
    Zhou, L
    Lin, G
    PHYTOCHEMISTRY, 2005, 66 (10) : 1121 - 1125