Carapanolides J-L from the Seeds of Carapa guianensis (Andiroba) and Their Effects on LPS-Activated NO Production

被引:26
作者
Matsui, Yuuki [1 ]
Kikuchi, Takashi [1 ]
Inoue, Takanobu [1 ]
Muraoka, Osamu [2 ]
Yamada, Takeshi [1 ]
Tanaka, Reiko [1 ]
机构
[1] Osaka Univ Pharmaceut Sci, Med Chem Lab, Takatsuki, Osaka 5691094, Japan
[2] Kinki Univ, Fac Pharmaceut Sci, Higashiosaka, Osaka 5778502, Japan
关键词
Carapa guianensis; andiroba; seeds; gedunin; phragmalin; limonoids; NO production; IN-VITRO; LIMONOIDS; AUBLET;
D O I
10.3390/molecules191117130
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 novel gedunin and two novel phragmalin-type limonoids, named carapanolides J-L (compounds 1-3) as well as a known gedunin-type limonoid 4 were isolated from the seeds of Carapa guianensis (andiroba). Their structures were determined on the basis of 1D and 2D NMR spectroscopy and HRFABMS. Compounds 1-4 were evaluated for their effects on the production of NO in LPS-activated mouse peritoneal macrophages.
引用
收藏
页码:17130 / 17140
页数:11
相关论文
共 17 条
[1]   In vitro antimalarial activity of limonoids from Khaya grandifoliola CDC (Meliaceae) [J].
Bickii, J ;
Njifutie, N ;
Foyere, JA ;
Basco, LK ;
Ringwald, P .
JOURNAL OF ETHNOPHARMACOLOGY, 2000, 69 (01) :27-33
[2]   Antiplasmodial activity of the andiroba (Carapa guianensis Aubl., Meliaceae) oil and its limonoid-rich fraction [J].
Cardoso Miranda Junior, Raimundo Nonato ;
Dolabela, Maria Fani ;
da Silva, Milton Nascimento ;
Povoa, Marinete Marins ;
Maia, Jose Guilherme S. .
JOURNAL OF ETHNOPHARMACOLOGY, 2012, 142 (03) :679-683
[3]   Acute and subacute toxicity of the Carapa guianensis Aublet (Meliaceae) seed oil [J].
Costa-Silva, J. H. ;
Lima, C. R. ;
Silva, E. J. R. ;
Araujo, A. V. ;
Fraga, M. C. C. A. ;
Ribeiro e Ribeiro, A. ;
Arruda, A. C. ;
Lafayette, S. S. L. ;
Wanderley, A. G. .
JOURNAL OF ETHNOPHARMACOLOGY, 2008, 116 (03) :495-500
[4]   Modulation of T lymphocyte and eosinophil functions in vitro by natural tetranortriterpenoids isolated from Carapa guianensis Aublet [J].
Ferraris, Fausto K. ;
Rodrigues, Rodrigo ;
da Silva, Vagner P. ;
Figueiredo, Raquel ;
Penido, Carmen ;
Henriques, Maria das Gracas M. O. .
INTERNATIONAL IMMUNOPHARMACOLOGY, 2011, 11 (01) :1-11
[5]   Carapanolides C-I from the seeds of andiroba (Carapa guianensis, Meliaceae) [J].
Inoue, Takanobu ;
Matsui, Yuuki ;
Kikuchi, Takashi ;
In, Yasuko ;
Muraoka, Osamu ;
Yamada, Takeshi ;
Tanaka, Reiko .
FITOTERAPIA, 2014, 96 :56-64
[6]   Guianolides A and B, New Carbon Skeletal Limonoids from the Seeds of Carapa guianensis [J].
Inoue, Takanobu ;
Matsui, Yuuki ;
Kikuchi, Takashi ;
In, Yasuko ;
Yamada, Takeshi ;
Muraoka, Osamu ;
Matsunaga, Shunyo ;
Tanaka, Reiko .
ORGANIC LETTERS, 2013, 15 (12) :3018-3021
[7]   Carapanolides A and B: unusual 9,10-seco-mexicanolides having a 2R,9S-oxygen bridge from the seeds of Carapa guianensis [J].
Inoue, Takanobu ;
Nagai, Yumi ;
Mitooka, Aya ;
Ujike, Reina ;
Muraoka, Osamu ;
Yamada, Takeshi ;
Tanaka, Reiko .
TETRAHEDRON LETTERS, 2012, 53 (49) :6685-6688
[8]  
Kirkeboen KA, 1999, ACTA ANAESTH SCAND, V43, P275
[9]   Epoxyazadiradione [J].
Malathi, R. ;
Rajan, S. S. ;
Kumar, R. Mohan ;
Narasimhan, S. ;
Ravikumar, K. .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 :O2483-O2485
[10]   Antiinflammatory effects of natural tetranortriterpenoids isolated from Carapa guianensis Aublet on zymosan-induced arthritis in mice [J].
Penido, C. ;
Conte, F. P. ;
Chagas, M. S. S. ;
Rodrigues, C. A. B. ;
Pereira, J. F. G. ;
Henriques, M. G. M. O. .
INFLAMMATION RESEARCH, 2006, 55 (11) :457-464