Mass Spectrometry for Natural Product Discovery

Louie, Katherine; Kosina, Suzanne M.; Hu, Yuntao; Otani, Hiroshi; Raad, Markus de; Kuftin, Andrea; Mouncey, Nigel J.; Bowen, Benjamin P.; Northen, Trent

doi:10.1016/b978-0-12-409547-2.14834-6

Cited by 23 publications

(12 citation statements)

References 319 publications

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“…As depicted in Figure 4, approximately 13 groups of glycosidic compounds may be distinguished based on their aglycone moiety: alcoholic glycosides, anthraquinone glycosides, cardiac glycosides, coumarin glycosides, chromone glycosides, cyanogenic glycosides, flavonoid glycosides, iridoid glycosides, phenolic glycosides, saponin glycosides, steviol glycosides, stilbene glycosides and thioglycosides (Louie et al, 2020). It is beyond the scope of this review to provide a detailed description of each class.…”

Section: Classificationmentioning

confidence: 99%

“…an ether bond), termed an O‐linkage. However, N‐linkages, S‐linkages, P‐linkages and C‐linkages are also possible (Louie et al, 2020). Additionally, α‐glycosides and β‐glycosides can be differentiated based on the location of the glycosidic bond below or above the plane of the glycone at the anomeric carbon.…”

Section: Classification and Properties Of Glycosidesmentioning

confidence: 99%

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Hitting the sweet spot: A systematic review of the bioactivity and health benefits of phenolic glycosides from medicinally used plants

Johnson

Mani

Broszczak

et al. 2021

Phytotherapy Research

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Phenolic acid and flavonoid glycosides form a varied class of naturally occurring compounds, characterised by high polarity-resulting from the glycone moiety-and the presence of multiple phenol functionalities, which often leads to strong antioxidant activity.Phenolic glycosides, and in particular flavonoid glycosides, may possess strong bioactive properties with broad spectrum activity. This systematic literature review provides a detailed overview of 28 studies examining the biological activity of phenolic and flavonoid glycosides from plant sources, highlighting the potential of these compounds as therapeutic agents. The activity of glycosides depends upon the biological activity type, identity of the aglycone and the identity and specific location of the glycone moiety. From studies reporting the activity of both glycosides and their respective aglycones, phenolic glycosides appear to generally be a storage/reserve pool of precursors of more bioactive compounds. The glycosylated compounds are likely to be more bioavailable compared to their aglycone forms, due to the presence of the sugar moieties. Hydrolysis of the glycoside in the in vivo environment would release the free aglycone, potentiating their biological activity. However, further high-quality studies are needed to firmly establish the clinical efficacy of glycosides from many of the plant species studied.

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Section: Classificationmentioning

confidence: 99%

Section: Classification and Properties Of Glycosidesmentioning

confidence: 99%

Hitting the sweet spot: A systematic review of the bioactivity and health benefits of phenolic glycosides from medicinally used plants

Johnson

Mani

Broszczak

et al. 2021

Phytotherapy Research

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“…The development of ecologically relevant media based on analysis of soil and sediment metabolites is an important future direction for increasing the ecological relevance of these microbial interaction studies. Analytical methods for metabolite extraction and detection should be selected to ensure proper coverage of metabolites of interest ( Mushtaq et al, 2014 ; Louie et al, 2020 ).…”

Section: Discussionmentioning

confidence: 99%

Biofilm Interaction Mapping and Analysis (BIMA) of Interspecific Interactions in Pseudomonas Co-culture Biofilms

et al. 2021

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Pseudomonas species are ubiquitous in nature and include numerous medically, agriculturally and technologically beneficial strains of which the interspecific interactions are of great interest for biotechnologies. Specifically, co-cultures containing Pseudomonas stutzeri have been used for bioremediation, biocontrol, aquaculture management and wastewater denitrification. Furthermore, the use of P. stutzeri biofilms, in combination with consortia-based approaches, may offer advantages for these processes. Understanding the interspecific interaction within biofilm co-cultures or consortia provides a means for improvement of current technologies. However, the investigation of biofilm-based consortia has been limited. We present an adaptable and scalable method for the analysis of macroscopic interactions (colony morphology, inhibition, and invasion) between colony-forming bacterial strains using an automated printing method followed by analysis of the genes and metabolites involved in the interactions. Using Biofilm Interaction Mapping and Analysis (BIMA), these interactions were investigated between P. stutzeri strain RCH2, a denitrifier isolated from chromium (VI) contaminated soil, and 13 other species of pseudomonas isolated from non-contaminated soil. One interaction partner, Pseudomonas fluorescens N1B4 was selected for mutant fitness profiling of a DNA-barcoded mutant library; with this approach four genes of importance were identified and the effects on interactions were evaluated with deletion mutants and mass spectrometry based metabolomics.

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“…The ease with which ultrasound may be coupled with other extraction techniques and the ability to operate at room temperature minimizes the problems associated with the oxidation/decomposition of target products, successfully enabling the isolation of phenolic compounds, antioxidants and cyanine [ 145 ], which are important for producing cosmetics, nutraceutics and pharmaceutics [ 66 ]. UAE can be applied on both the microscale and macroscale to extract compounds derived from various forms of life [ 146 ], where the application of UAE is energy/solvent/time efficient, potentially offering high yields of delicate compounds [ 66 , 145 , 147 ]. The mechanical effects of ultrasound have wider implications than extraction alone, and by varying the power and frequencies, it can find applications both upstream and downstream, with a simple and inexpensive commercial integration [ 148 ] and optimisation [ 149 ].…”

Section: Extraction Methods For High-value Chemicalsmentioning

confidence: 99%

Extraction of High-Value Chemicals from Plants for Technical and Medical Applications

Kapadia

Newell

Cunningham³

et al. 2022

IJMS

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Plants produce a variety of high-value chemicals (e.g., secondary metabolites) which have a plethora of biological activities, which may be utilised in many facets of industry (e.g., agrisciences, cosmetics, drugs, neutraceuticals, household products, etc.). Exposure to various different environments, as well as their treatment (e.g., exposure to chemicals), can influence the chemical makeup of these plants and, in turn, which chemicals will be prevalent within them. Essential oils (EOs) usually have complex compositions (>300 organic compounds, e.g., alkaloids, flavonoids, phenolic acids, saponins and terpenes) and are obtained from botanically defined plant raw materials by dry/steam distillation or a suitable mechanical process (without heating). In certain cases, an antioxidant may be added to the EO (EOs are produced by more than 17,500 species of plants, but only ca. 250 EOs are commercially available). The interesting bioactivity of the chemicals produced by plants renders them high in value, motivating investment in their production, extraction and analysis. Traditional methods for effectively extracting plant-derived biomolecules include cold pressing and hydro/steam distillation; newer methods include solvent/Soxhlet extractions and sustainable processes that reduce waste, decrease processing times and deliver competitive yields, examples of which include microwave-assisted extraction (MAE), ultrasound-assisted extraction (UAE), subcritical water extraction (SWE) and supercritical CO2 extraction (scCO2). Once extracted, analytical techniques such as chromatography and mass spectrometry may be used to analyse the contents of the high-value extracts within a given feedstock. The bioactive components, which can be used in a variety of formulations and products (e.g., displaying anti-aging, antibacterial, anticancer, anti-depressive, antifungal, anti-inflammatory, antioxidant, antiparasitic, antiviral and anti-stress properties), are biorenewable high-value chemicals.

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Mass Spectrometry for Natural Product Discovery

Cited by 23 publications

References 319 publications

Hitting the sweet spot: A systematic review of the bioactivity and health benefits of phenolic glycosides from medicinally used plants

Hitting the sweet spot: A systematic review of the bioactivity and health benefits of phenolic glycosides from medicinally used plants

Biofilm Interaction Mapping and Analysis (BIMA) of Interspecific Interactions in Pseudomonas Co-culture Biofilms

Extraction of High-Value Chemicals from Plants for Technical and Medical Applications

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