Assignment of 1H and 13C NMR signals and the alkene geometry at C-7 in borrelidin.

Kuo, Ming-S. T.; Yurek, David A.; Kloosterman, David A.

doi:10.7164/antibiotics.42.1006

Cited by 23 publications

(10 citation statements)

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“…The absorption at 2213 cm À1 in the IR spectrum suggested the presence of a nitrile group. All of these spectroscopic data agreed with those of the 18-membered macrolide borrelidin, 26) including the optical rotation. 27) Hence the active component was identified as borrelidin, as shown in Fig.…”

Section: Isolation and Identification Of Borrelidin From Culture Brotsupporting

confidence: 76%

Isolation of Borrelidin as a Phytotoxic Compound from a Potato PathogenicStreptomycesStrain

Cao

Khodakaramian

Arakawa

et al. 2012

Bioscience, Biotechnology, and Biochemistry

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Streptomyces species strain GK18, isolated in Iran, induced deep-pitted lesions on potato tubers, lesions different from the raised lesions induced by the usual scab-causing phytotoxin, thaxtomin. In addition, neither thaxtomin production nor hybridization to its biosynthetic probe was detected for strain GK18, suggesting the production of a different phytotoxin. The active component was extracted with ethyl acetate from culture filtrate of strain GK18, purified by gel filtration and silica gel chromatography, and identified as an 18-membered macrolide, borrelidin, by spectroscopic analysis. The purified borrelidin induced necrosis on potato tuber slices and inhibited the growth of shoots and roots of radish seedlings. This is the first report on the phytotoxicity of borrelidin as a possible causative compound of potato scab disease.

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Section: Isolation and Identification Of Borrelidin From Culture Brotsupporting

confidence: 76%

Isolation of Borrelidin as a Phytotoxic Compound from a Potato PathogenicStreptomycesStrain

Cao

Khodakaramian

Arakawa

et al. 2012

Bioscience, Biotechnology, and Biochemistry

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“…Physiological and biochemical index of xenograft nude mice Hz, CH 3 ), 0.74 (3H, d, J ¼ 7.2 Hz, CH 3 ), 0.60 (1H, brt, J ¼ 11.5 Hz); 13 C-NMR (150 MHz, DMSO-d 6 ) d (ppm): 177.6, 171.3, 143.6, 139.2, 127.8, 119.5, 116.8, 75.3, 71.0, 70.6, 48.5, 48.1, 45.9, 43.4, 37.6, 37.4, 35.9, 35.7, 34.8, 31.2, 29.3, 27.3, 26.4, 25.2, 20.8, 18.8, 18.6, 15.4. The spectral properties were identical with those reported in the literature 33,34. …”

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confidence: 86%

Effect of borrelidin on hepatocellular carcinoma cells in vitro and in vivo

et al. 2017

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“…S10, S13-19 and Table S1). [4][5][6][25][26][27] These data confirm that all borrelidin samples (chemoselectively-isolated, traditionally-isolated, and purchased standard) are identical.…”

supporting

confidence: 80%

Chemoselective enrichment as a tool to increase access to bioactive natural products: Case study borrelidin

Trader

Carlson

2015

Bioorganic & Medicinal Chemistry Letters

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Chemoselective purification technologies have seen great success in biomolecule isolation, with a classic example being the genetically-encoded His tag utilized to enrich desired proteins from a crude lysate. We sought to translate this purification tactic into a powerful tool for the isolation of natural products and demonstrate that chemoselective enrichment can reduce the number of purification steps required and increase the yield obtained for important natural products, as compared to the use of traditional chromatography methods alone. To date, we have reported reversible enrichment tags for three functional groups, carboxylic acids and aliphatic or aryl hydroxyls. To illustrate the power of chemoselectivity-mediated purification of natural products, we present here an improved isolation of borrelidin. Application of our carboxylic acid tag yielded pure borrelidin in only two steps and with double the yield acquired with traditional chromatography methods. These results highlight the utility of this orthogonal strategy to facilitate the isolation of natural products, which are often present in minute quantities in their source materials.

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Assignment of 1H and 13C NMR signals and the alkene geometry at C-7 in borrelidin.

Cited by 23 publications

References 0 publications

Isolation of Borrelidin as a Phytotoxic Compound from a Potato PathogenicStreptomycesStrain

Isolation of Borrelidin as a Phytotoxic Compound from a Potato PathogenicStreptomycesStrain

Effect of borrelidin on hepatocellular carcinoma cells in vitro and in vivo

Chemoselective enrichment as a tool to increase access to bioactive natural products: Case study borrelidin

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