Eremophilane Sesquiterpenes from the Genus <i>Ligularia</i>

Wu, Ling; Liao, Zhi‐Xin; Liu, Chao; Jia, Haiyang; Sun, Jinyue

doi:10.1002/cbdv.201500169

Cited by 36 publications

(16 citation statements)

References 127 publications

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“…The 1 H and 13 CNMR spectra of synthetic 2 were in agreement with the spectra reported in the literature for the isolated material, and both the opened and closed structures of 2 were observed in the 1 [7] do not differ significantly. The 1 H and 13 CNMR spectra of synthetic 2 were in agreement with the spectra reported in the literature for the isolated material, and both the opened and closed structures of 2 were observed in the 1 [7] do not differ significantly.…”

Section: Angewandte Chemiesupporting

confidence: 88%

“…[1] As their constitution cannot be rationalized by Ružičkas Isoprene Rule, [2] thestructural elucidation of the first isolated member, named eremophilone,w as challenging at the time.R obinson unraveled the mystery when he suggested ab iosynthetic pathway from an eudesmane precursor by methyl migration from C10 to C5 to form this new skeleton. [1] As their constitution cannot be rationalized by Ružičkas Isoprene Rule, [2] thestructural elucidation of the first isolated member, named eremophilone,w as challenging at the time.R obinson unraveled the mystery when he suggested ab iosynthetic pathway from an eudesmane precursor by methyl migration from C10 to C5 to form this new skeleton.…”

mentioning

confidence: 99%

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The Furan Shuffling Hypothesis: A Biogenetic Proposal for Eremophilane Sesquiterpenoids

et al. 2019

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Based on the structural similarities of the recently isolated eremophilane-type sesquiterpenoids microsphaeropsisin Ba nd Ca nd the iso-eremophilane periconianone C, ar evised biogenetic hypothesis for C8-C11-connected isoeremophilanes is presented and corroborated by strong experimental evidence.The first enantioselective total syntheses of microsphaeropsisin Ba nd Cw ere achieved starting from ak nowni ntermediate,w hose synthesis was elaborated previously in the total synthesis of periconianone A, and in atotal of 15 steps starting from g-hydroxy carvone.M ild reaction conditions for the subsequent a-ketol rearrangement not only resulted in the herein proposed conversion of microsphaeropsisin Bi nto periconianone C, but also in the conversion of microsphaeropsisin Ci nto 4-epi-periconianone C.

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Section: Angewandte Chemiesupporting

confidence: 88%

mentioning

confidence: 99%

The Furan Shuffling Hypothesis: A Biogenetic Proposal for Eremophilane Sesquiterpenoids

et al. 2019

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“…Eremophilane-type derivatives are structurally irregular and bicyclic natural products belonging to a small sesquiterpene family [ 1 , 2 ]. These eremophilane sesquiterpenes are biogenetically derived from farnesyl diphosphate in association with a methyl migration [ 3 ] and consist of three isoprene subunits [ 4 ].…”

Section: Introductionmentioning

confidence: 99%

Four New Highly Oxygenated Eremophilane Sesquiterpenes from an Endophytic Fungus Boeremia exigua Isolated from Fritillaria hupehensis

Yao

et al. 2022

JoF

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Four new eremophilane-type sesquiterpenes, boeremialanes A–D (1–4) were obtained from solid substrate cultures of Boeremia exigua (Didymellaceae), an endophytic fungus isolated from Fritillaria hupehensis (Liliaceae). Boeremialanes A–C (1–3) are highly oxygenated eremophilanes with a benzoate unit attached at the C-13 position and are rarely found in nature. Their structures and absolute configurations were determined by extensive spectroscopic methods, electronic circular dichroism (ECD), and nuclear magnetic resonance (NMR) calculations with DP4+ analysis. Boeremialane D (4) potently inhibited nitric oxide production in lipopolysaccharide-treated RAW264.7 macrophages with an IC50 of 8.62 μM and was more potent than the positive control, pyrrolidinedithiocarbamate (IC50 = 23.1 μM).

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“…More than 27 Ligularia species have been used as traditional Kazakh and Chinese medicinal herbs for the treatment of fever, pain, inflammation, intoxication, cough phlegm, removing blood stasis, emetic, diuresis, cholagogue and removing jaundice [3][4][5][6][7][8][9][10]. Phytochemical investigations of various Ligularia species showed the presence of monoterpenes, sesquiterpenes, diterpenes, triterpenes, alkaloids, steroids, flavonoids, lignans, and other skeleton type compounds, as well as some of these compounds showed various biological activities such as anticancer, antibacterial, antihepatotoxicity, antioxidant, and antithrombus [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Chemical Constituents of Ligularia Narynensis

Нурлыбекова¹,

Yang²,

Dyusebaeva³

et al. 2019

OF THE ACADEMY OF SCIENCES OF THE REPUBLIC OF KAZAKHSTAN

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Eremophilane Sesquiterpenes from the Genus Ligularia

Cited by 36 publications

References 127 publications

The Furan Shuffling Hypothesis: A Biogenetic Proposal for Eremophilane Sesquiterpenoids

The Furan Shuffling Hypothesis: A Biogenetic Proposal for Eremophilane Sesquiterpenoids

Four New Highly Oxygenated Eremophilane Sesquiterpenes from an Endophytic Fungus Boeremia exigua Isolated from Fritillaria hupehensis

Chemical Constituents of Ligularia Narynensis

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