Structure of three new terpenoids, spiciformisins a andb, and monocyclosqualene, isolated from the herbs ofligularia fischerivar.spiciformisand cytotoxicity

Lee, Kyung-Tae
Koo, Sung-Ja
Jung, Seung-Hee
Choi, Jongwon
Jung, Hyun-Ju
Park, Hee-Juhn

¹College of Pharmacy, Kyung-Hee University, 130-701 Seoul, Korea
²Deaprtment of Food and Nutrition, Kyung-Hee University, 130-701 Seoul, Korea
³College of Pharmacy, Kyungsung University, 608-736 Pusan, Korea
⁴Division of Applied Plant Sciences, Sangji University, 220-702 Wonju, Korea
⁵Division of Applied Plant Science, Sangji University, 660, Woosan-dong, 220-702 Wonju, Korea

(Received September 10, 2002)

Archives of Pharmacal Research 25(6):p 820-823, December 2002. | DOI: 10.1007/BF02976998

The diethyletter fraction from the leaves extract of Ligularia fischeri var. spiciformis (Composi-tae) 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-hexa-decatetraenyl)]-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 μg/ml against HL-60) in contrast to no cytotoxicity (IC₅₀, >200 ng/ml against HL-60 cells) of spiciformicin a with a cis-conjugated dienyl diexomethylene.