title: Cytotoxic lignans from fruits of Cleistanthus indochinensis: synthesis of cleistantoxin derivatives.
abstract: Two new aryl-tetralin lignans, 1 and 2, were isolated from the fruits of Cleistanthus indochinensis by bioassay-guided purification. Their structures were determined by spectroscopic analysis including MS and 2D NMR. The absolute configurations of 1 and 2 were established from examination of their CD spectra. Compound 1 was cytotoxic against KB cells with an IC(50) value of 0.022 μM, while compound 2 had weaker cytotoxicity, with an IC(50) value of 1.4 μM. When tested against other cancer cell lines (MCF-7, MCF-7R, and HT29), 1 showed an IC(50) of 0.014 against MCF-7R cells and an IC(50) of 0.036 μM against MCF-7 cells. A series of amide derivatives of a new lactone, homoderivatives of 1, were prepared. Of these derivatives, only compound 3 had weak cytotoxicity against KB cells.
authors.affiliation: Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet Road, Cau Giay, Hanoi, Vietnam.
authors.forename: Van Trinh Thi
authors.initials: VT
authors.lastname: Thanh
authors.forename: Van Cuong
authors.initials: VC
authors.lastname: Pham
authors.forename: Huong Doan Thi
authors.initials: HD
authors.lastname: Mai
authors.forename: Marc
authors.initials: M
authors.lastname: Litaudon
authors.forename: Françoise
authors.initials: F
authors.lastname: Guéritte
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.forename: Van Hung
authors.initials: VH
authors.lastname: Nguyen
authors.forename: Van Minh
authors.initials: VM
authors.lastname: Chau
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D019665:Euphorbiaceae / Q000737:chemistry*; D005638:Fruit / Q000737:chemistry; D006801:Humans; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D061986:MCF-7 Cells; D015394:Molecular Structure; D011034:Podophyllotoxin / Q000737:chemistry; D014744:Vietnam
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D017705:Lignans; C577384:cleistantoxin; C577385:neocleistantoxin; D011034:Podophyllotoxin