Structure and Absolute Configuration of Secondary Metabolites from Two Strains of Streptomyces chartreusis Associated with Attine Ants

Ortega, Humberto E.; Batista, João M.; Melo, Weilan Gomes da Paixão; Paula, Gabriela Toninato de; Pupo, Mônica Tallarico

doi:10.21577/0103-5053.20190194

Cited by 6 publications

(9 citation statements)

References 12 publications

(13 reference statements)

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“…115 Streptomyces chartreusis ICBG377 produced (−)-strepchazolins A (247), and B (248) ( Figure 69) whose AC was unambiguously confirmed as (5S,6S,9R)−247 and (5S,6S,9S)−248 by VCD and DFT calculations, in agreement with X-ray crystallography data and Mosher measurements. 116 The ethanol extract of Pandanus amaryllifolius gave 3 dextrorotatory indolizinones. The AC was determined by VCD and ECD as (8aR)-pandalizine C (249), (8R,8aS)-pandalizine D (250), and (7R,8aR)-pandalizine E (251) (Figure 69).…”

Section: Nitrogenated Compoundsmentioning

confidence: 99%

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Río

Joseph‐Nathan

2021

Natural Product Communications

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Although demonstrated in 1975, vibrational circular dichroism (VCD) finally started to popularize during this century as a reliable tool to determine the absolute configuration (AC) of organic molecules. This research field continues to be a very dynamic one, in particular for the study of natural products which are a unlimited source of chiral molecules. It therefore turns of interest to summarize the accomplishments published in recent years and to comment on some eventual difficulties that emerged in rare cases to complete the AC determination task. Therefore the aim of this review is to update VCD results for the AC assignment of natural products published from 2015 to 2019, a period in which VCD was reported in some 126 publications involving almost 300 molecules. They are organized according the type of studied metabolite allowing an easily search. The molecules correspond to 28 monoterpenes concerning 17 papers, to 42 sesquiterpenes in 14 papers, to 51 diterpenes in 19 publications, to 5 other terpenoids in three papers, to 48 aromatic molecules in 15 reports, to 20 polyketides in 10 publications, to 27 miscellaneous formulas also in 10 papers, and to 76 nitrogen containing compounds, which include alkaloids and their synthetic analogs, in 38 articles. The landscape of reviewed molecules is quite wide as it goes from simple monoterpenes, like borneol or camphor, to very relevant biological molecules like the alkaloid cocaine or tadalafil samples to distinguish genuine and counterfeit Cialis®. In addition, 5 natural products and a simple derivative published outside the reviewed period, were used to illustrate some aspects of density functional theory calculations.

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Section: Nitrogenated Compoundsmentioning

confidence: 99%

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Río

Joseph‐Nathan

2021

Natural Product Communications

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“…The actinobacterium produces the antibiotic streptazolin 7, its E-isomer (8), strepchazolin A (9), strepchazolin B (10), and the inorganic compound cyclooctasulfur (11), the active compound against Escovopsis (▶ Fig. 2) [45]. Compound 11 was also produced by S. chartreusis ICBG323, isolated from the exoskeleton of winged males of Mycocepurus goeldii [45].…”

Section: Natural Products Mediating Microbial Symbiosis Fungus-farminmentioning

confidence: 99%

“…2) [45]. Compound 11 was also produced by S. chartreusis ICBG323, isolated from the exoskeleton of winged males of Mycocepurus goeldii [45].…”

Section: Natural Products Mediating Microbial Symbiosis Fungus-farminmentioning

confidence: 99%

Chemical Ecology in Insect-microbe Interactions in the Neotropics

2020

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Small molecules frequently mediate symbiotic interactions between microorganisms and their hosts. Brazil harbors the highest diversity of insects in the world; however, just recently, efforts have been directed to deciphering the chemical signals involved in the symbioses of microorganisms and social insects. The current scenario of natural products research guided by chemical ecology is discussed in this review. Two groups of social insects have been prioritized in the studies, fungus-farming ants and stingless bees, leading to the identification of natural products involved in defensive and nutritional symbioses. Some of the compounds also present potential pharmaceutical applications as antimicrobials, and this is likely related to their ecological roles. Microbial symbioses in termites and wasps are suggested promising sources of biologically active small molecules. Aspects related to public policies for insect biodiversity preservation are also highlighted.

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“…As the difference in chemical structure between both compounds is a single hydroxyl group, hydroxylation of a piperidine backbone might prove beneficial for therapeutic application. In 2019, the same compounds 1 and 2 were isolated from Streptomyces chartreusis ICBG377, discovered in a fungal garden on the Acromyrmex subterraneus brunneus ant [16]. Though originating from totally different natural habitats, both strains were able to produce the same piperidine alkaloids under laboratory conditions.…”

Section: Piperidinesmentioning

confidence: 95%

Novel Alkaloids from Marine Actinobacteria: Discovery and Characterization

et al. 2021

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The marine environment is an excellent resource for natural products with therapeutic potential. Its microbial inhabitants, often associated with other marine organisms, are specialized in the synthesis of bioactive secondary metabolites. Similar to their terrestrial counterparts, marine Actinobacteria are a prevalent source of these natural products. Here, we discuss 77 newly discovered alkaloids produced by such marine Actinobacteria between 2017 and mid-2021, as well as the strategies employed in their elucidation. While 12 different classes of alkaloids were unraveled, indoles, diketopiperazines, glutarimides, indolizidines, and pyrroles were most dominant. Discoveries were mainly based on experimental approaches where microbial extracts were analyzed in relation to novel compounds. Although such experimental procedures have proven useful in the past, the methodologies need adaptations to limit the chance of compound rediscovery. On the other hand, genome mining provides a different angle for natural product discovery. While the technology is still relatively young compared to experimental screening, significant improvement has been made in recent years. Together with synthetic biology tools, both genome mining and extract screening provide excellent opportunities for continued drug discovery from marine Actinobacteria.

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Structure and Absolute Configuration of Secondary Metabolites from Two Strains of Streptomyces chartreusis Associated with Attine Ants

Cited by 6 publications

References 12 publications

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Vibrational Circular Dichroism Absolute Configuration of Natural Products From 2015 to 2019

Chemical Ecology in Insect-microbe Interactions in the Neotropics

Novel Alkaloids from Marine Actinobacteria: Discovery and Characterization

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