Fischelactone: A novel eremophilane dimer from Ligularia fischeri

Zhao, Hong; Weng, Cheng Wu; Tian, Xin; Lai, Peng Xiang; Huang, Jian Jun; Xie, Wei Dong

doi:10.1016/j.cclet.2010.01.008

Cited by 10 publications

(2 citation statements)

References 12 publications

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“…[12][13][14] Recently, we reported the structures of eremophilane dimers and an eremophilane lactam from this plant. 15,16) This paper describes the isolation and structure elucidation of two sesquiterpenoid-geranylhydroquinone hybrids, namely fischerisin A (1) and fischerisin B (2), isolated from the roots of L. fischeri. To the best of our knowledge, these two compounds represent a kind of unprecedented sesquiterpenoid derivative.…”

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Fischerisin A and B, Cytotoxic Sesquiterpenoid-Geranylhydroquinones from Ligularia fischeri

Xie

Weng

et al. 2011

Chem. Pharm. Bull.

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NoteSesquiterpenoids are the characteristic secondary metabolites of the Asteraceae family.1) Some of them showed a wide range of biological and pharmacological properties including insect antifeedant,2) anti-inflammatory activity, 3) antibacterial activity, 4) antimalarial activity, 5) cytotoxicity, 6) and nuclear factor kB (NF-kB) inhibition activity 7) etc. The investigation of the structure diversities, structure-activity relationships and biosynthetic approaches of the sesquiterpenoid constitutes in traditional Chinese medicines to screen for cytotoxic leads to drug has been the principal subject of our researchs. 8,9) Ligularia fischeri (LEDEB.) TURCZ. (Asteraceae) has long been used as a folk medicine in China for the treatment of coughs, inflammations, jaundice, scarlet fever, rheumatoidal arthritis, and hepatic diseases.10) In the mid1970s, Japanese researchers initially isolated furanoeremophilane-type sesquiterpenoids from this plant for the first time.11) Subsequent phytochemical researches of this plant collected in different region have resulted in the isolation of many eremophilane-type lactones and norsesquiterpene derivatives. [12][13][14] Recently, we reported the structures of eremophilane dimers and an eremophilane lactam from this plant. 15,16) This paper describes the isolation and structure elucidation of two sesquiterpenoid-geranylhydroquinone hybrids, namely fischerisin A (1) and fischerisin B (2), isolated from the roots of L. fischeri. To the best of our knowledge, these two compounds represent a kind of unprecedented sesquiterpenoid derivative. In addition, the in vitro cytotoxicity of both compounds against cultured human oral epidermoid carcinoma (KB) and human breast cancer (MCF-7) cell lines was also evaluated. Results and DiscussionThe petroleum ether (60-90°C)-Et 2 O-CH 3 OH (1 : 1 : 1) extract of the root of L. fischeri was chromatographed on a silica gel column with a gradient of hexane-acetone as eluent. After the sequential purification, fischerisin A (1) and fischerisin B (2) were finally obtained from the part of hexane-acetone (10 : 1).Fischerisin A (1) During the course of screening natural sesquiterpenoids for new antitumor agents, two novel compounds, fischerisin A (1) and fischerisin B (2), were isolated from the roots of Ligularia fischeri. Their structures were elucidated by interpretation of their IR, high resolution-mass spectrometry (HR-MS), 1D-and 2D-NMR data. Fischerisin A and B are the first representatives of a novel sesquiterpenoid-geranylhydroquinone hybrid, and both compounds exhibited in vitro cytotoxicity against cultured human oral epidermoid carcinoma (KB) and human breast cancer (MCF-7) cell lines with IC 50 values of 9.7 and 10.2 m mM, and 9.8 and 17.8 m mM, respectively.

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Fischerisin A and B, Cytotoxic Sesquiterpenoid-Geranylhydroquinones from Ligularia fischeri

Xie

Weng

et al. 2011

Chem. Pharm. Bull.

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“…Turcz., three eremophilane dimers, including fischelactone, 9b,9¢a-bis-1,8-dihydroligularenolide and 9b,9¢b-bis-1,8-dihydroligularenolide, have been recently identified by our research group. 7,8 The latter two ones have ever been isolated from Senecio tsoongianus. 9 Subsequent chemical investigation of the roots of L. fischeri afforded another new eremophilane dimer, named as fischelactone B (1) (Fig.…”

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confidence: 99%