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Structure of three new terpenoids, spiciformisins a andb, and monocyclosqualene, isolated from the herbs ofligularia fischeri var.spiciformis and cytotoxicity

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Abstract

The diethyletter fraction from the leaves extract ofLigularia fischeri var.spiciformis (Composi-tae) was subjected to silica gel column chromatography and yielded three new terpenoids named spiciformisin a (1), spiciformisinb (3), and monocyclosqualene (2). Acyclic diterpenes, spiciformisina 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 acis-conjugated dienyl diexomethylene.

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Correspondence to Hee -Juhn Park.

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Lee, K.T., Koo, S.J., Jung, S.H. et al. Structure of three new terpenoids, spiciformisins a andb, and monocyclosqualene, isolated from the herbs ofligularia fischeri var.spiciformis and cytotoxicity. Arch Pharm Res 25, 820–823 (2002). https://doi.org/10.1007/BF02976998

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