Center for Biological Sciences and Health, Mackenzie Presbyterian University, São Paulo, Brazil.
Pharm Biol. 2011 Nov;49(11):1173-9. doi: 10.3109/13880209.2011.575793.
Piper aduncum L. (Piperaceae) produces an essential oil (dillapiole) with great exploitative potential and it has proven effects against traditional cultures of phytopathogens, such as fungi, bacteria and mollusks, as well as analgesic action with low levels of toxicity.
This study investigated the in vivo anti-inflammatory activity of dillapiole. Furthermore, in order to elucidate its structure-anti-inflammatory activity relationship (SAR), semisynthetic analogues were proposed by using the molecular simplification strategy.
Dillapiole and safrole were isolated and purified using column chromatography. The semisynthetic analogues were obtained by using simple organic reactions, such as catalytic reduction and isomerization. All the analogues were purified by column chromatography and characterized by (1)H and (13)C NMR. The anti-inflammatory activities of dillapiole and its analogues were studied in carrageenan-induced rat paw edema model.
Dillapiole and di-hydrodillapiole significantly (p<0.05) inhibited rat paw edema. All the other substances tested, including safrole, were less powerful inhibitors with activities inferior to that of indomethacin.
These findings showed that dillapiole and di-hydrodillapiole have moderate anti-phlogistic properties, indicating that they can be used as prototypes for newer anti-inflammatory compounds. Structure-activity relationship studies revealed that the benzodioxole ring is important for biological activity as well as the alkyl groups in the side chain and the methoxy groups in the aromatic ring.
蓬蒿（胡椒科）产生一种具有巨大开发潜力的精油（大根香叶烯醇），它对传统的植物病原体培养物（如真菌、细菌和软体动物）具有明显的抑制作用，同时具有低毒性的镇痛作用。
本研究调查了大根香叶烯醇的体内抗炎活性。此外，为了阐明其结构-抗炎活性关系（SAR），我们提出了使用分子简化策略的半合成类似物。
使用柱层析法从蓬蒿和黄樟中分离和纯化大根香叶烯醇和黄樟素。通过简单的有机反应，如催化还原和异构化，获得半合成类似物。所有的类似物都通过柱层析进行纯化，并通过（1）H 和（13）C NMR 进行表征。在角叉菜胶诱导的大鼠足肿胀模型中研究了大根香叶烯醇及其类似物的抗炎活性。
大根香叶烯醇和二氢大根香叶烯醇显著（p<0.05）抑制大鼠足肿胀。所有其他测试的物质，包括黄樟素，都是较弱的抑制剂，其活性低于吲哚美辛。
这些发现表明，大根香叶烯醇和二氢大根香叶烯醇具有中度抗炎特性，表明它们可用作新型抗炎化合物的原型。构效关系研究表明，苯并二氧杂环丁烷环对于生物活性以及侧链中的烷基和芳环中的甲氧基都很重要。
