Furanoeremophilane derivatives from Senecio flavus

Torres, Pascual; Ayala, Juan H.; Grande, C.; Anaya, Josefa; Grande, M.

doi:10.1016/s0031-9422(99)00325-8

Cited by 42 publications

(31 citation statements)

References 15 publications

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“…After the sequential purification, fischerisin A (1) and fischerisin B (2) were finally obtained from the part of hexane-acetone (10 : 1). 16,17) Hence, compound 1 was supposed to be a derivative of furanoligularenine. The HMBC correlations of H 3 respectively.…”

Section: Resultsmentioning

confidence: 99%

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

Xie

Weng

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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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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Section: Resultsmentioning

confidence: 99%

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

Xie

Weng

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The aerial parts of S. flavus contained the four new furanoeremophilanes 158, 159, 161, and 162, oxidized at C(3), and a new eremophilenone lactam, 245. The rhizomes of the plant contained the new epoxyeremophilanolide 251 [64]. In 1991, the new furanoeremophilane 163 and two pairs of epimeric acetals, 164/165, and 166/167, with an eremophilane skeleton have been isolated from the aerial parts of S. pachyphyllos [67].…”

Section: Pyrrolizidine Alkaloidsmentioning

confidence: 99%

Chemical and Pharmacological Research on Plants from the Genus Senecio

Yang

Zhao

Wang

et al. 2011

Chemistry & Biodiversity

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“…More over the significance of generation and reactions of 1 O 2 with biomolecules in plants and living systems have been recognized . 12 Furanoeremophilanes, a novel class of sesquiterpenes is the constituents of several medicinal plants [13][14][15] and is well known for their medicinal values [16][17][18] e.g. antioxidant and…”

Section: Introductionmentioning

confidence: 99%

Photomediated transformation of eremophilanes-I: Photooxidation of 2ß-angeloyloxy-10ß-H-furanoeremophilane

Iqbal¹,

Gupta²,

Husain³

2006

Arkivoc

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The photochemical oxygenation reaction of 2β-angeloyloxy-10β-H-furanoeremophilane (1), a sesquiterpene, was studied in benzene and methanol. Three photoproducts were isolated and characterized by IR 1 H-NMR, 13 C-NMR and mass spectral studies. Sesquiterpene itself was found to be singlet oxygen ( 1 O 2 ) sensitizer. Addition of rose bengal increased the rate of photooxidation whereas as DABCO was found to decrease the rate of photolysis proving the involvement of 1 O 2 in these photoreactions. 2β-Angeloyloxy-8-hydroxy-10β-Heremophilanolide (4) and 2β-angeloyloxy-7,8-epoxy-10β-H-eremophilanolide (6) were obtained as products in benzene. Photolysis in methanol gave a single product 2β-angeloyloxy-10β-H-8-methoxy-12-hydroperoxy-dihydro-furanoeremophilane (7), which was further transformed into product 4, 8 and 12. Reaction was also carried out by adsorbing compound (1) on silica gel bound rose bengal, which yielded the products 4 and 6 with an increase in the rate of reaction.

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Furanoeremophilane derivatives from Senecio flavus

Cited by 42 publications

References 15 publications

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

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

Chemical and Pharmacological Research on Plants from the Genus Senecio

Photomediated transformation of eremophilanes-I: Photooxidation of 2ß-angeloyloxy-10ß-H-furanoeremophilane

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