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Antifungal nortriterpene and triterpene glycosides from the sea cucumber Apostichopus japonicus Selenka. 2012

Zenglei Wang, and Hongwei Zhang, and Weihua Yuan, and Wei Gong, and Hua Tang, and Baoshu Liu, and Karsten Krohn, and Ling Li, and Yanghua Yi, and Wen Zhang
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, PR China.

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.

UI MeSH Term Description Entries
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D000935 Antifungal Agents Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. Anti-Fungal Agents,Antifungal Agent,Fungicides, Therapeutic,Antibiotics, Antifungal,Therapeutic Fungicides,Agent, Antifungal,Anti Fungal Agents,Antifungal Antibiotics
D012616 Sea Cucumbers A class of Echinodermata characterized by long, slender bodies. Holothuroidea,Cucumber, Sea,Cucumbers, Sea,Holothuroideas,Sea Cucumber
D014315 Triterpenes A class of terpenes (the general formula C30H48) formed by the condensation of six isoprene units, equivalent to three terpene units. Triterpene,Triterpenoid,Triterpenoids

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