title: Structure of three new terpenoids, spiciformisins a and b, and monocyclosqualene, isolated from the herbs of Ligularia fischeri var. spiciformis and cytotoxicity.
abstract: The diethylether fraction from the leaves extract of Ligularia fischeri var. spiciformis (Compositae) was subjected to silica gel column chromatography and yielded three new terpenoids named spiciformisin a (1), spiciformisin b (3), and monocyclosqualene (2). Acyclic diterpenes, spiciformisin a and -b, were established as 3,7,11,15-tetramethyl-1,3(20)-hexadecadiene and 3,7,11,15-tetramethyl-1,3,6,10,14-hexadecapentaene (IUPAC), respectively. A monocyclic triterpene, monocyclosqualene, were determined as [3,8,12,16,16-pentamethyl-(3,7,11,15-hexadecatetraenyl)]-3,3,5-trimethyl-1-cyclohexene. The structures were determined on the basis of NMR and MS analysis. Spiciformicin b showed potent cytotoxicity (IC50, <9.7 microg/ml against HL-60) in contrast to no cytotoxicity (IC50, >200 microg/ml against HL-60 cells) of spiciformicin a with a cis-conjugated dienyl diexomethylene.
authors.affiliation: College of Pharmacy, Kyung-Hee University, Seoul, 130-701 Korea.
authors.forename: Kyung-Tae
authors.initials: KT
authors.lastname: Lee
authors.forename: Sung-Ja
authors.initials: SJ
authors.lastname: Koo
authors.forename: Seung-Hee
authors.initials: SH
authors.lastname: Jung
authors.forename: Jongwon
authors.initials: J
authors.lastname: Choi
authors.forename: Hyun-Ju
authors.initials: HJ
authors.lastname: Jung
authors.forename: Hee-Juhn
authors.initials: HJ
authors.lastname: Park
mesh_terms: D019659:Asteraceae / Q000633:toxicity*; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity*; D018922:HL-60 Cells; D006801:Humans; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity; D018515:Plant Leaves; D010946:Plants, Medicinal / Q000737:chemistry / Q000633:toxicity; D013185:Squalene / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity*; D020298:U937 Cells
chemical_list: D004224:Diterpenes; D010936:Plant Extracts; D013185:Squalene; C019556:squalane