Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor 45363, West Java, Indonesia.
Central Laboratory, Universitas Padjadjaran, Jatinangor 45363, West Java, Indonesia.
Molecules. 2023 Feb 24;28(5):2144. doi: 10.3390/molecules28052144.
Corr. is a member of the Meliaceae family that is widely spread in tropical and subtropical region of Asia and America. Traditionally, the fruit of this plant has been consumed because of its sweet taste. However, the fruit peels and the seeds of this plant have been rarely utilized. The previous chemical investigation of this plant showed the presence of secondary metabolites with many biological activities, including cytotoxic triterpenoid. Triterpenoids is a class of secondary metabolites which contain thirty carbon atoms in the main skeleton. The high modification of this type of compound, including the ring opening, highly oxygenated carbons, and the degradation of its carbon chain to give the nor-triterpenoid structure, is responsible for its cytotoxic activity. In this paper, we isolated and elucidated the chemical structure of two new onoceranoid triterpenes, kokosanolides E () and F (), from the fruit peels of Corr., along with a new tetranortriterpenoid, kokosanolide G (), from the seeds of Corr. The structural determination of compounds was undertaken through FTIR spectroscopic analysis, 1D and 2D NMR, mass spectrometry, as well as through a comparison of the chemical shifts of the partial structures of compounds with the literature data. The cytotoxic properties of compounds were tested against MCF-7 breast cancer cells using the MTT assay. Moderate activity was shown by compounds and , with IC values of 45.90 and 18.41 μg/mL, respectively, while compound showed no activity (IC 168.20 μg/mL). For the onoceranoid-type triterpene, the high symmetrical structure of compound is presumably the reason for its better cytotoxic activity compared with that of compound . Compound showed moderate activity, mainly because of the presence of the furan ring, which, based on the literature, gives better cytotoxic activity in a tetranortriterpenoid-type structure. The findings of three new triterpenoid compounds from indicate the significant value of this plant as a source of new compounds.
诃子是使君子科植物，广泛分布于亚洲和美洲的热带和亚热带地区。传统上，人们食用这种植物的果实，因为其味道甜美。然而，这种植物的果皮和种子却很少被利用。先前对该植物的化学研究表明，它含有许多具有生物活性的次生代谢产物，包括具有细胞毒性的三萜类化合物。三萜类化合物是一类含有三十个碳原子主骨架的次生代谢产物。这类化合物高度修饰，包括环的打开、高度氧化的碳原子，以及其碳链的降解以产生降三萜结构，这是其细胞毒性活性的原因。在本文中，我们从诃子的果皮中分离并阐明了两种新的诃子烷型三萜，诃子醇酸 E（）和 F（），以及一种新的四环三萜，诃子醇酸 G（），其结构来自诃子的种子。化合物的结构测定是通过 FTIR 光谱分析、1D 和 2D NMR、质谱以及通过化合物部分结构的化学位移与文献数据的比较来进行的。采用 MTT 法检测化合物对 MCF-7 乳腺癌细胞的细胞毒性。化合物和显示出中等活性，IC 值分别为 45.90 和 18.41μg/mL，而化合物则没有活性（IC 168.20μg/mL）。对于诃子烷型三萜，化合物的高对称结构可能是其与化合物相比具有更好的细胞毒性活性的原因。化合物显示出中等活性，主要是因为存在呋喃环，根据文献，在四环三萜型结构中具有更好的细胞毒性活性。从诃子中发现的三种新的三萜类化合物表明，这种植物作为新化合物的来源具有重要价值。
