三种新的四磺化三萜皂苷，chilensosides E (1)、 F (2)和G (3)从远东海参Paracaudina chilensis（Caudinidae，Molpadida）中分离得到。这些结构是基于1D和2D NMR光谱的广泛分析而建立的，并通过HR-ESI-MS数据进行了确认。这些化合物在它们的糖链中有所不同，即在单糖残基的数量（五个或六个）和硫酸盐基的位置上。Chilensosides E (1)和F (2)是带有硫酸盐基的五糖和一个硫酸盐基位于C-3 Glc3上的四磺化葡糖苷。而chilensoside G (3)是四磺化六糖苷。P. chilensis的糖苷生物合成分析揭示了这些结构形成了一个网络，这是由于硫酸盐基附着在几乎所有可能的位置。上半链比下半链早磺酸化。值得注意的是，在化合物1和2的底半链中出现的C-3 Glc3末端单糖残基的硫酸盐基的存在排除了这种糖链的进一步延伸的可能性。可能，糖基化和磺酸化过程是同时进行的生物合成阶段。它们可以相对于彼此移动，这是镶嵌式生物合成的特征特性。测试了化合物1-3对人类红细胞的溶血作用和对五株人类癌细胞系的细胞毒作用。这些化合物表现出适度的溶血活性，但对癌细胞无活性，可能是因为它们的结构特异性，例如四个硫酸盐基的位置组合。

Three new tetrasulfated triterpene glycosides, chilensosides E (1), F (2), and G (3), have been isolated from the Far-Eastern sea cucumber Paracaudina chilensis (Caudinidae, Molpadida). The structures were established based on extensive analysis of 1D and 2D NMR spectra and confirmed by HR-ESI-MS data. The compounds differ in their carbohydrate chains, namely in the number of monosaccharide residues (five or six) and in the positions of sulfate groups. Chilensosides E (1) and F (2) are tetrasulfated pentaosides with the position of one of the sulfate groups at C-3 Glc3, and chilensoside G (3) is a tetrasulfated hexaoside. The biogenetic analysis of the glycosides of P. chilensis has revealed that the structures form a network due to the attachment of sulfate groups to almost all possible positions. The upper semi-chain is sulfated earlier in the biosynthetic process than the lower one. Noticeably, the presence of a sulfate group at C-3 Glc3-a terminal monosaccharide residue in the bottom semi-chain of compounds 1 and 2-excludes the possibility of this sugar chain's further elongation. Presumably, the processes of glycosylation and sulfation are concurrent biosynthetic stages. They can be shifted in time in relation to each other, which is a characteristic feature of the mosaic type of biosynthesis. The hemolytic action of compounds 1-3 against human erythrocytes and cytotoxic activities against five human cancer cell lines were tested. The compounds showed moderate hemolytic activity but were inactive against cancer cells, probably because of their structural peculiarities, such as the combination of positions of four sulfate groups.