Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, PR China.
Department Chemie, Universität Paderborn, Warburger Strasse 100, 33098 Paderborn, Germany.
Food Chem. 2012 May 1;132(1):295-300. doi: 10.1016/j.foodchem.2011.10.080. Epub 2011 Oct 31.
A nortriterpene glycoside, 26-nor-25-oxo-holotoxin A1 (1), four triterpene glycosides, including both holostane and non-holostane types analogues, holotoxins D-G (2-5), together with three known triterpene glycosides, holotoxins A1 and B (6, 7), and cladoloside B (8), were isolated from the warty sea cucumber Apostichopus japonicus Selenka, a traditional tonic with high economic value in China. The structures of the new compounds were elucidated by a combination of detailed spectroscopic analysis and chemical methods. This is the first report of a nortriterpene glycoside isolated from sea cucumbers. These compounds showed potent antifungal activities in the in vitro biotest. A preliminary structure-activity analysis suggests that the 18(20) lactone group and the Δ(25) terminal double bond may increase the activity. The component of the carbohydrate chain seems play an important role whereas the double bond transformation from Δ(9(11)) to Δ(7) in the aglycone moiety contributes little to the bioactivity.
从中国传统滋补品疣海参（Apostichopus japonicus Selenka）中分离得到一个新的三萜糖苷，26-去-25-氧化全毒素 A1（1），四个三萜糖苷，包括 holostane 和非 holostane 型类似物，holotoxins D-G（2-5），以及三个已知的三萜糖苷，holotoxins A1 和 B（6,7）和 cladoloside B（8）。通过详细的光谱分析和化学方法相结合，阐明了新化合物的结构。这是首次从海参中分离出三萜糖苷。这些化合物在体外生物测定中表现出很强的抗真菌活性。初步的构效关系分析表明，18（20）内酯基团和 Δ（25）末端双键可能增加了活性。糖链的成分似乎起着重要作用，而糖苷部分的 Δ（9（11））到 Δ（7）双键的转化对生物活性贡献不大。
