Velutabularins A-J, phragmalin-type limonoids with novel cyclic moiety from Chukrasia tabularis var. velutina

被引：31

作者：

Luo, Jun ^{[1
]}

Wang, Jun-Song ^{[1
]}

Luo, Jian-Guang ^{[1
]}

Wang, Xiao-Bing ^{[1
]}

Kong, Ling-Yi ^{[1
]}

机构：

[1] China Pharmaceut Univ, Dept Nat Med Chem, Nanjing 210009, Peoples R China

来源：

TETRAHEDRON | 2011年 / 67卷 / 16期

基金：

中国国家自然科学基金;

关键词：

Tetranortriterpenoids; Phragmalin-type limonoids; 8-oxatricyclo[4,3,1(1,6)]decane; Chukrasia tabularis var. velutina; Anti-inflammatory; 16-NORPHRAGMALIN LIMONOIDS; SWIETENIA-MAHOGANI; LEAVES; ORTHOESTERS; SKELETONS; MELIACEAE; TWIGS; RING;

D O I：

10.1016/j.tet.2011.02.049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Velutabularins A-J, ten novel phragmalin-type limonoids, were isolated from the stem bark of Chukrasia tabularis var. velutina. In structures of 1-6, the tetrahydrofuran ring from dehydration of OH-15 and OH-17, ring C and 13/14/18-cyclopropanyl moiety formed an unprecedented 8-oxatricyclo[4,3,1(1,6)]decane. Compounds 7-10 are derivates of 1-6 opening the tetrahydrofuran ring. All of these compounds possess a novel C-16/C-30 delta-lactone ring, which were reported in phragmalins rarely. The structures of these novel compounds were elucidated based on extensive 1D and 2D spectroscopic analysis. The absolute configuration of 5 and 9 were determined by the calculated electronic circular dichroism (ECD) method. The anti-inflammatory activities of major compounds (2, 4, 5, 9) were evaluated for inhibitory activity against lipopolysaccharide (LPS) induced nitric oxide (NO) production in macrophage (RAW264.7) cell line. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：2942 / 2948

页数：7

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