Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai, 264003, China.
University of Chinese Academy of Sciences, Beijing, 100049, China.
Chem Biodivers. 2024 Jun;21(6):e202400335. doi: 10.1002/cbdv.202400335. Epub 2024 Mar 29.
Sea cucumbers release chemical repellents from their guts when they are in danger from predators or a hostile environment. To investigate the chemical structure of the repellent, we collected and chemically analyzed the viscera of stressed sea cucumbers (Apostichopus japonicus) in the Yellow Sea of China. Two undescribed triterpene glycosides (1 and 2), together with a known cladoloside A (3), were identified and elucidated as 3β-O-{2-O-[β-d-quinovopyranosyl]-4-O-[3-O-methyl-β-d-glucopyranosyl-(1→3)-β-d-glucopyranosyl]-β-d-xylopyranosyl}-holosta-9(11),25(26)-dien-16-one (1), 3β-O-{2-O-[β-d-glucopyranosyl]-4-O-[3-O-methyl-β-d-glucopyranosyl-(1→3)-β-d-glucopyranosyl]-β-d-xylopyranosyl}-holosta-9(11),25(26)-dien-16-one (2), 3β-O-{2-O-[3-O-methyl-β-d-glucopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-β-d-quinovopyranosyl]-β-d-xylopyranosyl}-holosta-9(11),25(26)-dien-16-one (3) by spectroscopic analysis, including HR-ESI-MS and NMR spectra. Compounds 1, 2, and 3 display embryonic toxicity, as indicated by their 96-hour post-fertilization lethal concentration (96 hpf-LC) values of 0.289, 0.536, and 0.091 μM, respectively. Our study discovered a class of triterpene glycoside compounds consisting of an oligosaccharide with four sugar units and a holostane aglycone. These compounds possess embryotoxicity and may serve as chemical defense molecules in marine benthic ecosystems.
当海参受到捕食者或恶劣环境的威胁时，它们会从内脏中释放出化学排斥物。为了研究这种排斥物的化学结构，我们在中国黄海采集并化学分析了处于应激状态的海参（糙海参）的内脏。鉴定并阐明了两种未描述的三萜糖苷（1 和 2），以及一种已知的克拉多皂苷 A（3），分别为 3β-O-{2-O-[β-d-奎诺吡喃糖基]-4-O-[3-O-甲基-β-d-吡喃葡萄糖基-(1→3)-β-d-吡喃葡萄糖基]-β-d-木吡喃糖基}-霍氏甾-9(11），25(26）-二烯-16-酮（1）、3β-O-{2-O-[β-d-吡喃葡萄糖基]-4-O-[3-O-甲基-β-d-吡喃葡萄糖基-(1→3)-β-d-吡喃葡萄糖基]-β-d-木吡喃糖基}-霍氏甾-9(11），25(26）-二烯-16-酮（2）、3β-O-{2-O-[3-O-甲基-β-d-吡喃葡萄糖基-(1→3)-β-d-木吡喃糖基-(1→4)-β-d-奎诺吡喃糖基]-β-d-木吡喃糖基}-霍氏甾-9(11），25(26）-二烯-16-酮（3）通过光谱分析，包括高分辨率电喷雾电离质谱和 NMR 光谱。化合物 1、2 和 3 表现出胚胎毒性，其 96 小时受精后致死浓度（96 hpf-LC）值分别为 0.289、0.536 和 0.091 μM。我们的研究发现了一类三萜糖苷化合物，由一个含有四个糖单位的寡糖和一个霍氏甾烷糖苷组成。这些化合物具有胚胎毒性，可能是海洋底栖生态系统中的化学防御分子。
