Reyes Carolina P, Núñez Marvin J, Jiménez Ignacio A, Busserolles Jérôme, Alcaraz María J, Bazzocchi Isabel L
Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna and Instituto Canario de Investigación del Cáncer, Tenerife, Canary Islands, Spain.
Bioorg Med Chem. 2006 Mar 1;14(5):1573-9. doi: 10.1016/j.bmc.2005.10.063. Epub 2005 Dec 5.
In the present study, we report that three new lupane triterpenes (1-3), in addition to 16 known ones (4-19), were isolated from the root bark of Maytenus cuzcoina and the leaves of Maytenus chiapensis. Their structures were elucidated by spectral analysis, including homonuclear and heteronuclear correlation NMR experiments (COSY, ROESY, HSQC, and HMBC). The natural compounds and derivatives 6a, 6b, 9a, and 9b have been tested for potential anti-inflammatory activity, and several compounds including 3-epicalenduladiol (2), 11alpha-hydroxy-glochidone (3), rigidenol (6), acetoxy-rigidenol (6a), 11alpha-acetoxy-30-chloro-3-oxo-lup-20(29)-ene (6b), betulin (9), 28-acetoxy-betulin (9a), epibetulin (12), epibetulinic acid (13), and betulonic acid (16) exhibited potent inhibitory effects on NO and prostaglandin E(2) production in mouse macrophages (RAW 264.7) stimulated with bacterial endotoxin. The structure-activity relationship is discussed in detail.
在本研究中，我们报告从库斯科美登木的根皮和恰帕斯美登木的叶中分离出了三种新的羽扇烷型三萜（1 - 3）以及16种已知的三萜（4 - 19）。通过光谱分析，包括同核和异核相关核磁共振实验（COSY、ROESY、HSQC和HMBC）阐明了它们的结构。对天然化合物及其衍生物6a、6b、9a和9b进行了潜在抗炎活性测试，包括3 - 表卡伦二醇（2）、11α - 羟基 - 格氏酮（3）、瑞吉多醇（6）、乙酰氧基瑞吉多醇（6a）、11α - 乙酰氧基 - 30 - 氯 - 3 - 氧代 - 羽扇 - 20(29) - 烯（6b）、桦木醇（9）、28 - 乙酰氧基 - 桦木醇（9a）、表桦木醇（12）、表桦木酸（13）和桦木酮酸（16）在内的几种化合物对细菌内毒素刺激的小鼠巨噬细胞（RAW 264.7）中一氧化氮和前列腺素E₂的产生表现出显著抑制作用。详细讨论了构效关系。
