Key Laboratory of Modern Preparation of Traditional Chinese Medicine of Ministry of Education＆ Research Center of Natural Resources of Chinese Medicinal Materials and Ethnic Medicine, Jiangxi University of Traditional Chinese Medicine, Nanchang 330004, PR China.
Key Laboratory of Modern Preparation of Traditional Chinese Medicine of Ministry of Education＆ Research Center of Natural Resources of Chinese Medicinal Materials and Ethnic Medicine, Jiangxi University of Traditional Chinese Medicine, Nanchang 330004, PR China.
Bioorg Chem. 2021 Feb;107:104622. doi: 10.1016/j.bioorg.2020.104622. Epub 2021 Jan 8.
The fruit of Citrus medica L. var. sarcodactylis Swingle is a functional food with rich nutrients and medicinal values because of its content of bioactive compounds. A bioactivity-guided chemical investigation from the fruits of C. medica L. var. sarcodactylis Swingle afforded three new benzodioxane neolignans (1-3), three new phenanthrofuran neolignan glycosides (4-6), two new biphenyl-ketone neolignans (7-8), two new 1',7'-bilignan neolignans (9-10), as well as fourteen known neolignan derivatives (11-24), which were isolated and characterized from the fruits of C. medica L. var. sarcodactylis Swingle for the first time. These neolignan derivatives were determined by extensive and comprehensive analyzing NMR, HR-ESI-MS, UV, IR spectral data and compared with the data described in the literature. Among them, compounds 1-3 and 12-13 exhibited moderate hepatoprotective activities to improve the survival rates of HepG2 cells from 46.26 ± 1.90% (APAP, 10 mM) to 67.23 ± 4.25%, 62.87 ± 4.43%, 60.06 ± 6.34%, 56.75 ± 2.30%, 58.35 ± 6.14%, respectively. Additionally, compounds 7-8 and 21-22 displayed moderate neuroprotective activities to raise the survival rates of PC12 cells from 55.30 ± 2.25% to 66.94 ± 3.37%, 70.98 ± 5.05%, 64.64 ± 1.93%, and 62.81 ± 4.11% at 10 μM, respectively. The plausible biogenetic pathway and preliminary structure-activity relationship of the selected compounds were scientifically summarized and discussed in this paper.
橘红果实是芸香科柑橘属植物橘及其栽培变种的干燥外层果皮，具有丰富的营养成分和药用价值，其生物活性成分含量较高。从橘红果实中进行生物活性导向的化学成分研究，得到了三个新的苯并二氧杂环庚烷型新木脂素（1-3）、三个新的菲呋喃型新木脂素糖苷（4-6）、两个新的联苯酮型新木脂素（7-8）、两个新的 1',7'-联二苯型新木脂素（9-10）以及 14 个已知的新木脂素衍生物（11-24），这些化合物均为首次从橘红果实中分离得到。通过对 NMR、HR-ESI-MS、UV、IR 光谱数据的广泛和综合分析，并与文献中描述的数据进行比较，确定了这些新木脂素衍生物的结构。其中，化合物 1-3 和 12-13 表现出中等的肝保护活性，可将 HepG2 细胞的存活率从 46.26±1.90%（APAP，10mM）提高到 67.23±4.25%、62.87±4.43%、60.06±6.34%、56.75±2.30%和 58.35±6.14%，化合物 7-8 和 21-22 则表现出中等的神经保护活性，可将 PC12 细胞的存活率从 55.30±2.25%提高到 66.94±3.37%、70.98±5.05%、64.64±1.93%和 62.81±4.11%，在 10μM 时。本文对所选化合物的可能生物合成途径和初步结构-活性关系进行了科学总结和讨论。
