Carapanolides C-I from the seeds of andiroba (Carapa guianensis, Meliaceae)

被引：23

作者：

Inoue, Takanobu ^{[1
]}

Matsui, Yuuki ^{[1
]}

Kikuchi, Takashi ^{[1
]}

In, Yasuko ^{[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, Dept Organ Chem, Higashiosaka, Osaka 5778502, Japan

来源：

FITOTERAPIA | 2014年 / 96卷

关键词：

Carapanolides C-I; Carapa guianensis; Seed; Meliaceae; Limonoid; LIMONOIDS; CHEMISTRY; AUBLET; FLOWER;

D O I：

10.1016/j.fitote.2014.04.006

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Five new mexicanolide-type limonoids, carapanolides C-G (1-5), together with two new phragmalin-type limonoids, carapanolides H-I (6, 7), were isolated from the oil of Carapa guianasis AUBLET (Meliaceae) seeds. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR spectra and FABMS. Carapanolides C (1), E (3), and I (7) exhibited moderate activity in the P388 (IC50 17.9 mu M in 1, 15.8 mu M in 3) and L1210 cell lines (IC50 13.3 mu M in 1, 18.1 mu M in 3, 16.9 mu M in 7). On the other hand, Carapanolide D (2) exhibited a strong inhibitory effect in the HL-60 cell line (IC50 11.0 mu M), Carapanolides F (4) showed inhibitory activity in the L1210 cell line (IC50 15.9 mu M), and the cytotoxic activity of Carapanolides I (7) was moderate in all cell lines. (C) 2014 Elsevier B.V. All rights reserved.

引用

页码：56 / 64

页数：9

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]

Fang X, 2011, CURR ORG CHEM, V15, P1363

[5]

Ferraris Fausto K., 2011, INT IMMUNOPHARMACOL, V11, P1

[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] Plant Orthoesters [J].

Liao, Shang-Gao ;

Chen, Hua-Dong ;

Yue, Jian-Min .

CHEMICAL REVIEWS, 2009, 109 (03) :1092-1140

[9] Chaetomugilins I-O, new potent cytotoxic metabolites from a marine-fish-derived Chaetomium species. Stereochemistry and biological activities [J].

Muroga, Yasuhide ;

Yamada, Takeshi ;

Numata, Atsushi ;

Tanaka, Reiko .

TETRAHEDRON, 2009, 65 (36) :7580-7586

[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

← 1 2 →