Carapanosins DF from the Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production

被引：6

作者：

Inoue, Takanobu ^{[1
]}

Ohmori, Shoko ^{[1
]}

Kikuchi, Takashi ^{[1
]}

Yamada, Takeshi ^{[1
]}

Tanaka, Reiko ^{[1
]}

机构：

[1] Osaka Univ Pharmaceut Sci, Lab Med Chem, 4-20-1 Nasahara, Takatsuki, Osaka 5691094, Japan

来源：

MOLECULES | 2018年 / 23卷 / 07期

关键词：

Carapa guianensis; Meliaceae; andiroba; seeds; limonoids; seco-phragmalin; mexicanolide; carapanosins A-C; NO production; BIOLOGICAL-ACTIVITIES; CARAPANOLIDES; LIMONOIDS; AUBLET; OIL;

D O I：

10.3390/molecules23071778

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 nor-phragmalin-type limonoid, named carapanosin D (1), and two novel mexicanolide-type limonoids, carapanosins E (2) and F (3), were isolated from the seed oil of andiroba (Carapa guianensis A(ublet)), a traditional medicine in Brazil and Latin American countries. Their structures were unambiguously determined on the basis of spectroscopic analyses using one-dimensional (1D) and two-dimensional (2D) NMR techniques and High resolution Fast Atom Bombardment Mass Spectrometry (HRFABMS). Compounds 1-3 were evaluated for their effects on the production of nitric oxide (NO) in Lipopolysaccharide (LPS)-activated mouse peritoneal macrophages. The NO inhibitory assay suggested that compounds 2 and 3 have high potency as inhibitors of macrophage activation.

引用

页数：9

共 20 条

[1] 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

[2] 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

[3] Guianolactones A and B, Two Rearranged Pentacyclic Limonoids from the Seeds of Carapa guianensis [J].

Higuchi, Keiichiro ;

Tani, Yoshimi ;

Kikuchi, Takashi ;

In, Yasuko ;

Yamada, Takeshi ;

Muraoka, Osamu ;

Tanaka, Naonobu ;

Tanaka, Reiko .

CHEMISTRY-AN ASIAN JOURNAL, 2017, 12 (23) :3000-3004

[4] Carapanosins A-C from Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production [J].

Higuchi, Keiichiro ;

Miyake, Teppei ;

Ohmori, Shoko ;

Tani, Yoshimi ;

Minoura, Katsuhiko ;

Kikuchi, Takashi ;

Yamada, Takeshi ;

Tanaka, Reiko .

MOLECULES, 2017, 22 (03)

[5] Carapanolides M-S from seeds of andiroba (Carapa guianensis, Meliaceae) and triglyceride metabolism-promoting activity in high glucose-pretreated HepG2 cells [J].

Inoue, Takanobu ;

Matsui, Yuuki ;

Kikuchi, Takashi ;

Yamada, Takeshi ;

In, Yasuko ;

Muraoka, Osamu ;

Sakai, Chie ;

Ninomiya, Kiyofumi ;

Morikawa, Toshio ;

Tanaka, Reiko .

TETRAHEDRON, 2015, 71 (18) :2753-2760

[6] 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

[7] 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

[8] 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

[9] Plant Orthoesters [J].

Liao, Shang-Gao ;

Chen, Hua-Dong ;

Yue, Jian-Min .

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

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

Matsui, Yuuki ;

Kikuchi, Takashi ;

Inoue, Takanobu ;

Muraoka, Osamu ;

Yamada, Takeshi ;

Tanaka, Reiko .

MOLECULES, 2014, 19 (11) :17130-17140

← 1 2 →