title: Antifungal nortriterpene and triterpene glycosides from the sea cucumber Apostichopus japonicus Selenka.
abstract: 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.
authors.affiliation: Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, PR China.
authors.forename: Zenglei
authors.initials: Z
authors.lastname: Wang
authors.affiliation: Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, PR China.
authors.forename: Hongwei
authors.initials: H
authors.lastname: Zhang
authors.affiliation: Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, PR China.
authors.forename: Weihua
authors.initials: W
authors.lastname: Yuan
authors.affiliation: Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, PR China.
authors.forename: Wei
authors.initials: W
authors.lastname: Gong
authors.affiliation: Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, PR China.
authors.forename: Hua
authors.initials: H
authors.lastname: Tang
authors.affiliation: Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, PR China.
authors.forename: Baoshu
authors.initials: B
authors.lastname: Liu
authors.affiliation: Department Chemie, Universität Paderborn, Warburger Strasse 100, 33098 Paderborn, Germany.
authors.forename: Karsten
authors.initials: K
authors.lastname: Krohn
authors.affiliation: Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, PR China.
authors.forename: Ling
authors.initials: L
authors.lastname: Li
authors.affiliation: Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, PR China. Electronic address: yiyanghua@hotmail.com.
authors.forename: Yanghua
authors.initials: Y
authors.lastname: Yi
authors.affiliation: Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, PR China. Electronic address: wenzhang1968@163.com.
authors.forename: Wen
authors.initials: W
authors.lastname: Zhang
mesh_terms: D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry*; D012616:Sea Cucumbers / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry*
chemical_list: D000935:Antifungal Agents; D014315:Triterpenes
keywords: Antifungal activity; Apostichopus japonicas; Nortriterpene glycoside; Sea cucumber; Triterpene glycoside