β-Carboline Alkaloid Constituents from aThermoactinomyces SP.Strain Isolated from Livingston Island, Antarctica

Bratchkova, Anna; Иванова, В.; Gousterova, A.; Laatsch, Hartmut

doi:10.5504/bbeq.2012.0021

“…The structures of the five compounds (3-7) from fraction 7, and 14 compounds (8-21) from other fractions were determined by comparing their MS, UV, and NMR data with those reported in the literature. The known compounds were β-carboline (3) (Bratchkova et al, 2012), 1-methyl-β-carboline 4) (Bratchkova et al, 2012), sarpagine (5) (Rukachaisirikul et al, 2017), lochnerine (6) (Kam et al, 1999), vellosiminol (7) (Mbeunkui et al, 2012), tetrahydroalstonine (8) (Achenbach et al, 1997), isoreserpiline (9) (Gupta et al, 2012), 10-methoxytetrahydroalstonine (10) (Gupta et al, 2012), carapanaubine (11) (Khatoon et al, 2022), isocarapanaubine (12) (Ahmad et al, 2010), N a -methylrauflorine (13) (Carlos et al, 2016), venoterpine (14) (Rukachaisirikul et al, 2017), mitoridine (15) (Kumara et al, 2019), yohimbine (16) (Zhan et al, 2020b), ajmaline (17) (Lim et al, 2014), vinmajorine D (18) (Zhang et al, 2016), 17-epivinmajorine D (19) (Zhang et al, 2016), peraksine (20) (Gao et al, 2015), and 17-epi-peraksine (21) (Arthur et al, 1968).…”

Section: Isolation and Structural Elucidation Of The Active Compounds...mentioning

confidence: 99%

Identification of chemosensitizing agents of colorectal cancer in Rauvolfia vomitoria using an NMR-based chemometric approach

Cui

¹

,

Guo

²

,

Wang

³

et al. 2023

Front. Chem.

0

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Searching for new adjuvants of conventional chemotherapeutic approaches against colorectal cancer cells is extremely urgent. In current research, a non-targeted analytical approach was established by combining proton nuclear magnetic resonance spectroscopy with a chemometrics data mining tool to identify chemosensitizing agents from Rauvolfia vomitoria. This approach enabled the identification of potential active constituents in the initial fractionation process and provided their structural information. This strategy was validated by its application to Rauvolfia vomitoria extract exhibiting chemosensitizing activity on 5-fluorouracil against colorectal cancer cells. After the workflow, the biochemometrics analysis showed that at least 15 signals (Variable influence on projection (VIP) > 1) could have contributions in the differentiation of various fractions. Through systematic literature and database searches, we found that the most active fraction (fraction 7) exhibited the highest presence of sabazin-type and armaniline-type alkaloids, which were potential chemosensitizers as previously reported. To validate the results of the strategy, the effect of 5-FU and compounds isolated from fraction seven incubation on HCT-8 and LoVo cell vialibilty were evaluated. These results evidenced that compound β-carboline (3), 1-methyl-β-carboline (4), and lochnerine (6) could enhance the cytotoxicity of 5-fluorouracil against to Colorectal cancer cells. Besides, 21 compounds including two new compounds were isolated from Rauvolfia vomitoria. The experimental results verify the reliability of the method, and this approach provides a new and efficient tool to overcome some of the bottlenecks in natural products drug discovery.

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“…Due to the large number of substituents and/or substitution patterns found in β-carbolines, these alkaloids display a large variety of physiological and pharmacological properties. 74 1-Acetyl-β-carboline was first reported in 1977 from the plant Ailanthus malabarica. 75 Since then, it has been reported as a metabolite of a marine sponge, T. ignis, 75 and several marine and soil microorganisms.…”

Section: Investigation Of Anoxybacillus Flavithermus (Wk1)mentioning

confidence: 99%

Validation of a Spectroscopic Screening Method for Secondary Metabolites from New Zealand Extremophilic Microbes

Braganza¹

0

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The existing protocol for the screening of natural products from marine invertebrates and macroalgae has been demonstrated successfully at VUW on multiple occasions. This study describes the evaluation of an adapted version of the protocol to screen liquid microbial cultures. The adapted protocol was carried out using an NMR-guided approach and was used to screen 10 New Zealand extremophilic microbes. Investigation of the bacteria Anoxybacillus flavithermus led to the isolation of the known compound 1-acetyl-β-carboline (25), which was briefly evaluated for its biological activity. A detailed investigation on the marine bacteria Shewanella sp. resulted in the isolation of indole-3-carboxaldehyde (93) and 14 known 2,5-diketopiperazines (36, 38, 41–44, 53, 54, 94–99). Three of the isolated 2,5-DKPs were tested against Saccharomyces cerevisiae to evaluate their antifungal activity, the results of which are also described. Overall, the use of the adapted screening method proved successful to guide the isolation of secondary metabolites from microbial cultures.

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“…79 Many β-carboline compounds function as monoamine oxidase (MAO) inhibitors. 74 MAO is an enzyme responsible for breaking down monoamine neurotransmitters such as dopamine, serotonin, epinephrine, and many more. Inhibitors of this enzyme can thus be used for treatments of psychiatric disorders such as depression and schizophrenia as they prevent the breakdown of these neurotransmitters in the brain.…”

Section: Investigation Of Anoxybacillus Flavithermus (Wk1)mentioning

confidence: 99%

Validation of a Spectroscopic Screening Method for Secondary Metabolites from New Zealand Extremophilic Microbes

Braganza¹

0

View full text Add to dashboard Cite

The existing protocol for the screening of natural products from marine invertebrates and macroalgae has been demonstrated successfully at VUW on multiple occasions. This study describes the evaluation of an adapted version of the protocol to screen liquid microbial cultures. The adapted protocol was carried out using an NMR-guided approach and was used to screen 10 New Zealand extremophilic microbes. Investigation of the bacteria Anoxybacillus flavithermus led to the isolation of the known compound 1-acetyl-β-carboline (25), which was briefly evaluated for its biological activity. A detailed investigation on the marine bacteria Shewanella sp. resulted in the isolation of indole-3-carboxaldehyde (93) and 14 known 2,5-diketopiperazines (36, 38, 41–44, 53, 54, 94–99). Three of the isolated 2,5-DKPs were tested against Saccharomyces cerevisiae to evaluate their antifungal activity, the results of which are also described. Overall, the use of the adapted screening method proved successful to guide the isolation of secondary metabolites from microbial cultures.

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β-Carboline Alkaloid Constituents from aThermoactinomyces SP.Strain Isolated from Livingston Island, Antarctica

Cited by 7 publications

References 20 publications

Identification of chemosensitizing agents of colorectal cancer in Rauvolfia vomitoria using an NMR-based chemometric approach

Identification of chemosensitizing agents of colorectal cancer in Rauvolfia vomitoria using an NMR-based chemometric approach

Validation of a Spectroscopic Screening Method for Secondary Metabolites from New Zealand Extremophilic Microbes

Validation of a Spectroscopic Screening Method for Secondary Metabolites from New Zealand Extremophilic Microbes

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