Structure of three new terpenoids, spiciformisins a and b, and monocyclosqualene, isolated from the herbs of Ligularia fischeri var. spiciformis and cytotoxicity.
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.
Lee
Kyung-Tae
KT
College of Pharmacy, Kyung-Hee University, Seoul, 130-701 Korea.
Koo
Sung-Ja
SJ
Jung
Seung-Hee
SH
Choi
Jongwon
J
Jung
Hyun-Ju
HJ
Park
Hee-Juhn
HJ
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
D004224:Diterpenes; D010936:Plant Extracts; D013185:Squalene; C019556:squalane