Monção Nayana Bruna Nery, Araújo Bruno Quirino, Silva Jurandy do Nascimento, Lima Daisy Jereissati Barbosa, Ferreira Paulo Michel Pinheiro, Airoldi Flavia Pereira da Silva, Pessoa Cláudia, Citó Antonia Maria das Graças Lopes
Department of Chemistry, Federal University of Piauí, Teresina 64049-550, PI, Brazil.
Postgraduate Program in Pharmaceutical Sciences, Federal University of Piauí, Teresina 64049-550, PI, Brazil.
Molecules. 2015 Mar 5;20(3):4204-24. doi: 10.3390/molecules20034204.
Mimosa caesalpiniifolia is a native plant of the Brazilian northeast, and few studies have investigated its chemical composition and biological significance. This work describes the identification of the first chemical constituents in the ethanolic extract and fractions of M. caesalpiniifolia stem bark based on NMR, GC-qMS and HRMS analyses, as well as an assessment of their cytotoxic activity. GC-qMS analysis showed fatty acid derivatives, triterpenes and steroid substances and confirmed the identity of the chemical compounds isolated from the hexane fraction. Metabolite biodiversity in M. caesalpiniifolia stem bark revealed the differentiated accumulation of pentacyclic triterpenic acids, with a high content of betulinic acid and minor amounts of 3-oxo and 3β-acetoxy derivatives. Bioactive analysis based on total phenolic and flavonoid content showed a high amount of these compounds in the ethanolic extract, and ESI-(-)-LTQ-Orbitrap-MS identified caffeoyl hexose at high intensity, as well as the presence of phenolic acids and flavonoids. Furthermore, the evaluation of the ethanolic extract and fractions, including betulinic acid, against colon (HCT-116), ovarian (OVCAR-8) and glioblastoma (SF-295) tumour cell lines showed that the crude extract, hexane and dichloromethane fractions possessed moderate to high inhibitory activity, which may be related to the abundance of betulinic acid. The phytochemical and biological study of M. caesalpiniifolia stem bark thus revealed a new alternative source of antitumour compounds, possibly made effective by the presence of betulinic acid and by chemical co-synergism with other compounds.
含羞草决明是巴西东北部的本土植物，很少有研究对其化学成分和生物学意义进行调查。这项工作描述了基于核磁共振（NMR）、气相色谱-质谱联用（GC-qMS）和高分辨质谱（HRMS）分析，对含羞草决明茎皮乙醇提取物及其馏分中首批化学成分的鉴定，以及对它们细胞毒性活性的评估。GC-qMS分析显示出脂肪酸衍生物、三萜类化合物和甾体类物质，并确认了从己烷馏分中分离出的化合物的身份。含羞草决明茎皮中的代谢物生物多样性揭示了五环三萜酸的差异积累，其中桦木酸含量高，3-氧代和3β-乙酰氧基衍生物含量少。基于总酚和黄酮含量的生物活性分析表明，乙醇提取物中这些化合物含量很高，电喷雾电离负离子模式线性离子阱-轨道阱质谱（ESI-(-)-LTQ-Orbitrap-MS）高强度鉴定出咖啡酰己糖，以及酚酸和黄酮类化合物的存在。此外，对乙醇提取物及其馏分（包括桦木酸）针对结肠（HCT-116）、卵巢（OVCAR-8）和胶质母细胞瘤（SF-295）肿瘤细胞系的评估表明，粗提取物、己烷和二氯甲烷馏分具有中度至高抑制活性，这可能与桦木酸的丰富含量有关。因此，对含羞草决明茎皮的植物化学和生物学研究揭示了一种新的抗肿瘤化合物替代来源，可能由于桦木酸的存在以及与其他化合物的化学协同作用而发挥作用。
