Twelve Novel and Diverse 16-Norphragmalin-Type Limonoids from Chukrasia tabularis var. velutina
Twelve Novel and Diverse 16-Norphragmalin-Type Limonoids from Chukrasia tabularis var. velutina
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来自 Chukrasia tabularis var. 的 12 种新颖且多样化的 16-Norphragmalin 型柠檬苦素。
DOI：
10.1248/cpb.60.195
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发表时间：
2012-02-01
影响因子：
1.7
通讯作者：
Kong, Ling-Yi
中科院分区：
文献类型：
--
作者：
Luo, Jun;Li, Yi;Kong, Ling-Yi
从管形柱花草Chukrasia tubularis var.的茎皮中分离得到一系列结构相似的C-15-酰基16-去甲phragmalin型柠檬苦素类化合物chuktabrins C-J（1-8）和chuktabularins U-X（9-12）。天鹅绒。它们的结构是建立在详细的光谱分析的基础上，化合物1的绝对构型是通过使用镜面CuK α辐射的单晶X射线研究确定的。化合物7和8是首次发现的C-15-酰基-16-去甲补骨脂素，其C-15位上带有酮基烷基，化合物4和8是首次发现的柠檬苦素，其特征碳酸酯部分分别在OH-9/OH-8或OH-1/OH-8上酯化。这些柠檬苦素类化合物的生物合成途径是合理的，基于分离的新颖和多样的结构，这提供了一个新的见解的合理的生物合成的C-15-酰基16-norphragmalin型柠檬苦素。主要分离物的抗炎活性被评价为对脂多糖（LPS）诱导的巨噬细胞（RAW 264.7）细胞系中的一氧化氮（NO）产生的抑制活性，IC 50值范围为2.40至16.90 μ m。
A series of novel and structurally related C-15-acyl 16-norphragmalin-type limonoids, chuktabrins C-J (1-8) and chuktabularins U-X (9-12), were isolated from the stem bark of Chukrasia tubularis var. velutina. Their structures were established on the basis of detailed spectroscopic analysis, and the absolute configuration of compound 1 was determined by a single-crystal X-ray study using a mirror CuK alpha radiation. Compounds 7 and 8 were unprecedent C-15-acyl 16-norphragmalins with ketonic alkyl appendage at C-15, and compounds 4 and 8 were first examples of limonoid with a characteristic carbonate moiety esterified at OH-9/OH-8 or OH-1/OH-8 respectively. A biosynthetic pathway of these limonoids was reasonably presumed based on the novel and diverse structures isolated, which provides a new insight into the plausible biosynthesis of C-15-acyl 16-norphragmalin-type limonoids. The anti-inflammatory activity of major isolates were evaluated for inhibitory activity against lipopolysaccharide (LPS) induced nitric oxide (NO) production in macrophage (RAW264.7) cell line, with IC50 value ranging from 2.40 to 16.90 mu m.