Jietacins with potent nematocidal activity; efficient isolation of novel analogs and divergent total synthesis of jietacin A, B, C, and D

Sugawara, Akihiro; Kubo, Masahiko; Nakashima, Takuji; Hirose, Tomoyasu; Tsunoda, Noriaki; Yahagi, Kyoichi; Asami, Yukihiro; Yamada, Takeshi; Shiomi, Kazuro; Takahashi, Yōko; Ōmura, Satoshi; Sunazuka, Toshiaki

doi:10.1016/j.tet.2015.02.038

Cited by 14 publications

(21 citation statements)

References 37 publications

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“…The oxygen atom of the azoxy moiety was determined to be on the side of the olefin group by the 1 H chemical shifts adjacent to the azoxy group, 15 and by comparison of spectroscopic data with related azoxy containing natural products reported in the literature (e.g., elaiomycins, Supporting Information Tables S46 and S47), 6 maniwamycins, 7,8 and jietacins. 10 The characteristic UV absorption maximum at 232 nm, which was also observed in similar alkenyl substituted azoxy compounds (maniwamycins and elaiomycins), 6,8 determined the Z-configuration of the azoxy group. 15 In addition, the NOESY spectrum revealed no correlations between H-1′ and H-2 or H3-3, which would be likely observed in an E-configuration.…”

Section: Resultsmentioning

confidence: 72%

“…Interestingly, soil Actinobacteria appear to be producers of the growing number of natural azoxides exemplified by elaiomycins, 6 maniwamycins, 7,8 and others. [9][10][11][12][13] These secondary metabolites exhibit a wide array of biological activity being cytotoxic, or having nematicidal, antifungal, or antibacterial effects. [6][7][8][9][10] Despite the wide spectrum of bioactivity, limited information is available for the impact of structure variations on the biological effects of naturally occurring azoxy compounds.…”

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confidence: 99%

“…[9][10][11][12][13] These secondary metabolites exhibit a wide array of biological activity being cytotoxic, or having nematicidal, antifungal, or antibacterial effects. [6][7][8][9][10] Despite the wide spectrum of bioactivity, limited information is available for the impact of structure variations on the biological effects of naturally occurring azoxy compounds. Moreover, microbial secondary metabolites such as azoxides could play a role as a natural defense against other microbes or animals.…”

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confidence: 99%

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Azodyrecins A–C: Azoxides from a Soil-Derived Streptomyces Species

et al. 2020

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Section: Resultsmentioning

confidence: 72%

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confidence: 99%

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confidence: 99%

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Azodyrecins A–C: Azoxides from a Soil-Derived Streptomyces Species

et al. 2020

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“…Nematocidal antibiotics, jietacins A ( 19 ) and B ( 20 ), isolated from the culture broth of a Streptomyces sp. [ 40 , 41 ], exhibited 10 times higher activities against the pine wood nematode Bursaphelenchus hgnicolus in comparison to avermectin Bla, which is known to have a potent activity against various nematodes and which is used as a nematocidal agent in the veterinary field [ 42 , 43 ].…”

Section: Azo Metabolites Derived From Actinomycetes and Fungal Speciementioning

confidence: 99%

Pharmacological and Predicted Activities of Natural Azo Compounds

Dembitsky

Gloriozova

Poroikov

2017

Nat. Prod. Bioprospect.

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This paper describes research on natural azo compounds isolated from fungi, plant, bacteria, and invertebrates. More than 120 biologically active diazene containing alkaloids demonstrate confirmed pharmacological activity, including antitumor, antimicrobial, and antibacterial effects. The structures, origin, and biological activities of azo compounds are reviewed. Utilizing the computer program PASS, some structure–activity relationship new activities are also predicted, pointing toward possible new applications of these compounds. This article emphasizes the role of natural azo compounds as an important source of drug prototypes and leads for drug discovery.

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“…Compound 31 has moderate in vitro nematicidal activity against M. exigua with an LC 50 value of 171 mg/L, and affeic acid 3- O -methyltransferase homodimer may be its target of action . The LC 50 values of compounds 33 and 34 against C. elegans were 0.42 and 0.27 mg/L, respectively. , Compound 33 has only moderate or low acute toxicity, its LD 50 is >300 mg/kg, and it does not exhibit mutagenic effects. Fatty chains may be the necessary active functional group for nematicidal compounds.…”

Section: Chemical Nematicidal Active Compoundsmentioning

confidence: 97%

Chemical Nematicides: Recent Research Progress and Outlook

Chen

Song

2020

J. Agric. Food Chem.

129

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Plant-parasitic nematodes have caused huge economic losses to agriculture worldwide and seriously threaten the sustainable development of modern agriculture. Chemical nematicides are still the most effective means to manage nematodes. However, the long-term use of organophosphorus and carbamate nematicides has led to a lack of field control efficacy and increased nematode resistance. To meet the huge market demand and slow the growth of resistance, new nematicides are needed to enter the market. The rational design and synthesis of new chemical scaffolds to screen for new nematicides is still a difficult task. We reviewed the latest research progress of nematicidal compounds in the past decade, discussed the structure−activity relationship and mechanism of action, and recommended some nematicidal active fragments. It is hoped that this review can update the recent progress on nematicide discoveries and provide new ideas for the design and mechanism of action studies of nematicides.

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Jietacins with potent nematocidal activity; efficient isolation of novel analogs and divergent total synthesis of jietacin A, B, C, and D

Cited by 14 publications

References 37 publications

Azodyrecins A–C: Azoxides from a Soil-Derived Streptomyces Species

Azodyrecins A–C: Azoxides from a Soil-Derived Streptomyces Species

Pharmacological and Predicted Activities of Natural Azo Compounds

Chemical Nematicides: Recent Research Progress and Outlook

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