Anti-inflammatory of pyrrolizidine alkaloids from Heliotropium digynum

被引:12
作者
Aboelmagd, Mohamed [1 ,2 ]
Elokely, Khaled [3 ,4 ,5 ]
Zaki, Mohamed A. [6 ]
Said, Ataa [2 ]
Haggag, Eman G. [7 ]
Ross, Samir A. [1 ,8 ]
机构
[1] Univ Mississippi, Natl Ctr Nat Prod Res, Sch Pharm, University, MS 38677 USA
[2] Natl Res Ctr, Dept Pharmacognosy, Giza 12622, Egypt
[3] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
[4] Temple Univ, Inst Computat Mol Sci, Philadelphia, PA 19122 USA
[5] Tanta Univ, Dept Pharmaceut Chem, Tanta 31527, Egypt
[6] Beni Suef Univ, Dept Pharmacognosy, Fac Pharm, Bani Suwayf, Egypt
[7] Helwan Univ, Dept Pharmacognosy, Fac Pharm, Cairo 11795, Egypt
[8] Univ Mississippi, Sch Pharm, Pharmacognosy Div, Dept BioMol Sci, University, MS 38677 USA
关键词
Heliotropium digynum; New pyrrolizidine alkaloid; Anti-inflammatory; Docking; ACCURATE DOCKING; PROTEIN; GLIDE; SUBULATUM; FISCH; MEY;
D O I
10.1007/s00044-017-2128-y
中图分类号
R914 [药物化学];
学科分类号
100705 [微生物与生化药学];
摘要
One new and six known pyrrolizidine alkaloids (1-7) were isolated from the 70% ethanol extract of the aerial parts of Heliotropium digynum (Forssk.) C. Chr. The chemical structure of the new compound, 7-Angeloylsincamidine N-Oxide (4) was determined by extensive 1D and 2D NMR spectroscopic analysis and HRESIMS. The absolute configuration of 4 was elucidated by comparing the experimental and electronic circular dichroism spectra. The anti-inflammatory activity of the ethanolic extract and compounds 1, 2, 4, and 6 were evaluated against the Nitric oxide production in lipopolysaccharide induced murine macrophages RAW 264.7 cells. The IC50 values of the tested compounds were 52.4, 85.1, 105.1, and 7.9 A mu M, respectively, while the % inhibition of the ethanolic extract at 25 A mu g/mL was 78.7%. A docking study was conducted to provide more explanation about the activity of the tested compounds.
引用
收藏
页码:1066 / 1073
页数:8
相关论文
共 32 条
[1]
Inflammation and cancer: How hot is the link? [J].
Aggarwal, Bharat B. ;
Shishodia, Shishir ;
Sandur, Santosh K. ;
Pandey, Manoj K. ;
Sethi, Gautam .
BIOCHEMICAL PHARMACOLOGY, 2006, 72 (11) :1605-1621
[2]
Nitric oxide synthases: structure, function and inhibition [J].
Alderton, WK ;
Cooper, CE ;
Knowles, RG .
BIOCHEMICAL JOURNAL, 2001, 357 (03) :593-615
[3]
Alwahibi M., 2013, African Journal of Plant Science, V7, P85
[4]
Aqheel M. A., 2013, Indian Journal of Research in Pharmacy and Biotechnology, V1, P707
[5]
PYRROLIZIDINE ALKALOIDS FROM HELIOTROPIUM-ROTUNDIFOLIUM [J].
ASIBAL, CF ;
GELBAUM, LT ;
ZALKOW, LH .
JOURNAL OF NATURAL PRODUCTS, 1989, 52 (04) :726-731
[6]
ALKALOIDS OF AMSINCKIA SPECIES - A INTERMEDIA FISCH + MEY A HISPIDA (RUIZ + PAV) JOHNST AND A LYCOPSOIDES LEHM [J].
CULVENOR, CC ;
SMITH, LW .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1966, 19 (10) :1955-&
[7]
A REVIEW ON HELIOTROPIUM INDICUM L. (BORAGINACEAE) [J].
Dash, G. K. ;
Abdullah, M. S. .
INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES AND RESEARCH, 2013, 4 (04) :1253-1258
[8]
New pyrrolizidine alkaloids from Heliotropium crassifolium [J].
Farsam, H ;
Yassa, N ;
Sarkhail, P ;
Shafiee, A .
PLANTA MEDICA, 2000, 66 (04) :389-391
[9]
An in vitro comparison of the cytotoxic potential of selected dehydropyrrolizidine alkaloids and some N-oxides [J].
Field, Reuel A. ;
Stegelmeier, Bryan L. ;
Colegate, Steven M. ;
Brown, Ammon W. ;
Green, Benedict T. .
TOXICON, 2015, 97 :36-45
[10]
Structural characterization of nitric oxide synthase isoforms reveals striking active-site conservation [J].
Fischmann, TO ;
Hruza, A ;
Niu, XD ;
Fossetta, JD ;
Lunn, CA ;
Dolphin, E ;
Prongay, AJ ;
Reichert, P ;
Lundell, DJ ;
Narula, SK ;
Weber, PC .
NATURE STRUCTURAL BIOLOGY, 1999, 6 (03) :233-242