Diversity of Ligularia kanaitzensis in sesquiterpenoid composition and neutral DNA sequences

Tori, Motoo; Watanabe, Aki; Matsuo, Sachie; Okamoto, Yasuko; Tachikawa, Kana; Takaoka, Shigeru; Gong, Xun; Kuroda, Chiaki; Hanai, Ryo

doi:10.1016/j.tet.2008.02.036

Cited by 61 publications

(90 citation statements)

References 46 publications

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“…We are interested in biologically active terpenoids from Asteraceae plants and have studied the chemical constituents of Ligularia, [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] Saussurea, 22,23) Cremanthodium, [24][25][26][27] and Eupatorium. [28][29][30][31] In our previous study on E. glehnii growing in Japan, especially in Obihiro (Hokkaido), Fujimi-cho (Nagano), and Tokushima, a large diversity in the chemical constituents was found, while there was no diversity in DNA sequences (atpB-rbcL intergenic region).…”

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confidence: 99%

Germacranolides and Their Diversity of <i>Eupatorium heterophyllum</i> Collected in P. R. China

et al. 2014

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Eight new hydroperoxides and a new enone of germacrane-type sesquiterpenoids were isolated from the aerial parts of eight different samples of Eupatorium heterophyllum DC. (Asteraceae) collected in P. R. China. The structures were determined based on spectroscopic analyses. Seven of the eight samples produced hiyodorilactone A as a major constituent, while one afforded neither hiyodorilactone nor hydroperoxide. The results indicated the presence of diversity within this species.

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confidence: 99%

Germacranolides and Their Diversity of <i>Eupatorium heterophyllum</i> Collected in P. R. China

et al. 2014

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“…[78] (À)-Eremophilene (4) has been isolated from a multitude of plants. [63,[79][80][81] It was also found in extracts of the coral Plexaurella fusifera, [82] and has been synthesized by different chemical methods. [64][65][66] This work proves the existence of pairs of enantiomers of natural products: the (À)-enantiomer in plants and the (+)-enantiomer one in bacterium.…”

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confidence: 99%

Characterization of the Gene Cluster CYP264B1‐geoA from Sorangium cellulosum So ce56: Biosynthesis of (+)‐Eremophilene and Its Hydroxylation

Schifrin

Günnewich

et al. 2014

ChemBioChem

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Terpenoids can be found in almost all forms of life; however, the biosynthesis of bacterial terpenoids has not been intensively studied. This study reports the identification and functional characterization of the gene cluster CYP264B1-geoA from Sorangium cellulosum So ce56. Expression of the enzymes and synthesis of their products for NMR analysis and X-ray diffraction were carried out by employing an Escherichia coli whole-cell conversion system that provides the geoA substrate farnesyl pyrophosphate through simultaneous overexpression of the mevalonate pathway genes. The geoA product was identified as a novel sesquiterpene, and assigned NMR signals unambiguously proved that geoA is an (+)-eremophilene synthase. The very tight binding of (+)-eremophilene (∼0.40 μM), which is also available in S. cellulosum So ce56, and its oxidation by CYP264B1 suggest that the CYP264B1-geoA gene cluster is required for the biosynthesis of (+)-eremophilene derivatives.

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“…Many eremophilane-type compounds possess unique chemical structures and a variety of bioactivities. 16,17 Compounds 2 and 3 showed ABK circumvention activity against MRSA.…”

Section: Discussionmentioning

confidence: 99%

Paraphaeosphaeride D and berkleasmin F, new circumventors of arbekacin resistance in MRSA, produced by Paraphaeosphaeria sp. TR-022

et al. 2016

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Two new compounds, designated paraphaeosphaeride D (1) and berkleasmin F (2) together with a previously known compound, berkleasmin A (3), isolated from a culture broth of the fungus Paraphaeosphaeria sp. TR-022, proved to be new circumventors of arbekacin (ABK) resistance in methicillin-resistant Staphylococcus aureus (MRSA). The structures of 1 and 2 were elucidated by spectroscopic analyses, including various NMR experiments. All compounds showed 10-100 times ABK circumvention activities using the paper disc method and reduced the MIC values of ABK against MRSA from 16 μg ml(-1) to 4 μg ml(-1) (fourfold) using the agar dilution method. These new compounds might be promising lead compounds for developing circumventors of ABK resistance in MRSA.

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Diversity of Ligularia kanaitzensis in sesquiterpenoid composition and neutral DNA sequences

Cited by 61 publications

References 46 publications

Germacranolides and Their Diversity of <i>Eupatorium heterophyllum</i> Collected in P. R. China

Germacranolides and Their Diversity of <i>Eupatorium heterophyllum</i> Collected in P. R. China

Characterization of the Gene Cluster CYP264B1‐geoA from Sorangium cellulosum So ce56: Biosynthesis of (+)‐Eremophilene and Its Hydroxylation

Paraphaeosphaeride D and berkleasmin F, new circumventors of arbekacin resistance in MRSA, produced by Paraphaeosphaeria sp. TR-022

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